You’re lucky if you find a spot.

Especially on evenings and weekends.

But now, as a family of four, it was finally time to get a car, which we did last month. (Yay!)

Since then, I’ve been thinking about the idea of the ‘perfect spot’ right outside our house, and how it might actually be the wrong thing to aim for.

Yes, it’s close and convenient. But it’s also unpredictable. After wearily arriving home from a long weekend away, I often end up circling, second-guessing whether a spot might come up, before eventually parking a few streets away.

There’s friction in the short walk, yes. But there’s less stress, fewer variables, and more momentum. It’s often quicker to commit to that upfront than waste time chasing the ‘perfect’ outcome.

It’s a small reminder of a broader truth: we often get stronger outcomes when we stop trying to eliminate friction altogether, and instead recognise where it shows up, and design with it in mind.

I. Should designers code?

It depends. What’s your intended outcome?

The ‘should designers code?’ debate pops up again and again. I’ve worked with teams where it’s a hard requirement and others where there’s more flexibility. For me, the better question is: what’s the most effective path to reach your goal?

For most product teams, the outcome is shipping improvements to customers. That often means designers collaborating closely with engineers to get a shared vision into production. And the more fluent everyone is in the shared language of code, the less translation is needed, and the smoother the delivery becomes.

That fluency can take time to build. But it’s often the kind of friction that leads to better outcomes in the long run, clearer handoffs, fewer misunderstandings, and faster iteration.

Questions to consider:

→ What outcome are you optimising for?

→ Where is unnecessary translation slowing you down?

II. Should designers use acronyms?

It depends. Who’s your audience?

Until I worked with Harry—Monzo’s former Head Writer extraordinaire—I rarely thought about acronyms. I had a rough mental model: some are widely understood (PM, UI, OKR), and some are hyper-specific (PSC, SAR, SCA in Fintech).

But when I joined Monzo, and teams with deep banking expertise, my mental model flipped. What was obvious to me wasn’t obvious to them and vice versa.

Acronyms often feel like shortcuts. But they only work when everyone shares the same reference point. Otherwise, they introduce tiny moments of uncertainty. Mini speed bumps that add up.

Taking a little extra time to write something out might feel like unnecessary friction. But if it means your message is clearer, quicker to grasp, and easier to act on, it’s friction worth embracing.

Questions to consider:

→ Who are you communicating with (human or AI)?

→ Will your shortcut actually make things faster?

III. Should designers write prompts?

It depends. What’s your strongest communication tool?

As we enter this AI era, I’ve seen growing attention on ‘how to prompt like a designer’. I’m all for designers using AI—and writing better—but I think the real skill isn’t in crafting magic phrases. It’s in choosing the right communication method for the task, even if that means leaning into more friction up front.

Many designers are naturally strong visual communicators. Whether that’s sketching a quick diagram to explain information architecture or attaching a Figma mockup to clarify intent, these methods are often faster, and with a higher resolution, than words alone.

In other words, ‘good prompting’ is often just a proxy for communicating clearly. And words aren’t the only tool in the box.

Questions to consider:

→ What’s the clearest way to express your intent?

→ Are you defaulting to speed over clarity?

Wrapping up

Not all friction is wasted effort. In the right places, it helps clarify thinking, align teams, and build momentum. And often, it’s that quiet effort early on that sets up everything that follows.

So as you navigate your next project or team decision I’d suggest you pause to consider:

→ What’s your real goal?

→ Where is friction showing up?

→ What kind of effort might actually help you get there faster?

Thanks for reading!

This was inspired by these two fantastic posts

• Taste at Speed — By Carly Ayres

• The Most Valuable Commodity in the World is Friction — By Kyla Scanlon

Today’s newsletter covers a bit more of the why behind it. But first, the LinkedIn post:

✨ Introducing: Hack Weeks Dot Com ✨

Four-day, hands-on AI sprints for non-engineers who want to learn practical AI skills through doing.

AI is everywhere. But for many of us, it still feels a bit abstract. We read the headlines, try a few tools, groan at the hype, and feel the pressure to “get ahead.”

With new models launching constantly, and dystopian futures striking fear into our feeds, it’s hard to know where to start, or the practical steps to build confidence with this new medium.

Hack Weeks give you the space, structure and support to explore how you can get the most from AI tools, in an immersive, grounded and creative way.

You’ll spend four focused days experimenting with real tools to ‘ship a thing’, alongside a small group to share learnings and reflections with, led by Jonny Burch and me. We’re experienced product and design leaders who’ve built our careers around helping individuals and teams grow at companies like Monzo Bank and Deliveroo.

Whether you’re in Design, PM, Marketing, People, Ops, Leadership (or another role entirely!) we invite you to join our first open hack week on June 2nd, or bring us in to run a bespoke sprint for your team. No coding experience needed.

👉 Hack weeks dot com 👈

Why AI? Why now?

While not always framed explicitly as ‘AI’, this theme seems to have woven itself into the fabric of most conversations happening across my coaching and consulting practice. Whether it’s helping folks figure out what their future roles look like, the skills they need to hire for or the near-term tactics that could just help them unlock more of their own capacity.

And for me to! As an independent person, AI has been an invaluable tool and thought partner in shaping my own practice and amplifying my capacity.

But the AI hype is real. And depending on your disposition, equal parts terrifying and exciting. Your eyes may have already glazed over before reaching this bit!

But really, all of this came down to a simple feeling I couldn’t shake. One that hit me during a holiday last month. I kept feeling drawn to read more, learn more, and build. Not from FOMO, but from a deep curiosity. Something about this space keeps tugging at me.

Why Jonny and me?

We’re not AI gurus.

We’re not leet vibecoding experts.

We’re (hopefully) not vacuous hype merchants.

But we are curious makers and care about creating the conditions for people to thrive.

If the world really is accelerating toward an AI-first future, more people will need help making sense of what that means, and how to use it to be more creative, compassionate, and capable in their work and lives. And that’s something we’re both super passionate to help enable.

While working through this process, Jonny and I mapped out how we think work is changing, where things might be heading, and what kind of future we want to help shape. You might find the exercise useful too. But the bigger question we asked ourselves was: what role can we play? What value can we add?

For me, the answer lies in unlocking more of people’s creative human potential, and giving them the confidence to actually use it in their daily work. And I believe AI holds a lot of potential to help with this, whether it’s freeing up people’s time, or helping push and challenge their creative muscle to unlock new heights.

Why Hack Weeks?

You could take a course or read a guide, there’s no shortage of them! But with things moving so fast, theory only takes you so far. Until you get hands-on and experiment, it’s hard to grasp how these tools can meaningfully impact your day-to-day work beyond that first (often underwhelming) impression. Doing it alongside peers only accelerates the learning. At least, that was my big takeaway from the prototype we ran in April.

And then there’s the concept of the Jagged Frontier. Coined by Wharton Professor, Ethan Mollick, in his excellent book: Co-Intelligence:

“AI is weird. No one actually knows the full range of capabilities of the most advanced Large Language Models, like GPT-4. No one really knows the best ways to use them, or the conditions under which they fail. There is no instruction manual. On some tasks AI is immensely powerful, and on others it fails completely or subtly. And, unless you use AI a lot, you won’t know which is which.”

Which, to me, says this: the only real way to learn how to use AI tools is through regular, messy, hands-on experimentation. And I believe the fastest way to do this is through clear structure, accountability, peer-to-peer learning and guides who’ve been where you are before.

Of course, Hack Weeks isn’t the only way to do this, but we’ve designed it to be one of the most energising, grounded, and collaborative ways to start. So if you’re curious to see what AI can do for you, we’d love for you to consider joining us.

Check out hackweeks.com, or drop us a line at hello@hackweeks.com if you have any questions.

Lastly, a quick editorial note: this newsletter isn’t going anywhere. Hack Weeks will run alongside my coaching and consulting work, and this will remain a space for sharing ideas to help design leaders level up. That said, you can probably expect a few more AI-flavoured posts in the mix.

I used to have two rules of thumb for my career:

• Follow the conversations you wish could continue, and the roles that enable them.

• Leave jobs after two years, plus or minus a year. Because after this point your rate of learning hits diminishing returns and you’ll grow overly familiar with a single environment, making it harder to adjust to others.

Since striking out on my own I’ve found myself re-visiting and expanding these to build a set of tactics that make sense for where my world is today and the clients and projects I take on tomorrow.

While I initially leant heavily on data to make the ‘right’ decisions, I’ve increasingly found myself drawn to intuition and gut feel on my biggest moves. And it’s liberating.

‘Vibe coding’ has drawn both fans and skeptics. But to me, the underlying idea is about leaning into intuition as a way to move forward at pace, in a world increasingly caught up in change. The most authentic path, is one that’s liberatingly human: just follow the vibe.

I figure at this point one of two things will be true:

• Your eyes have glazed over and you’re about to open another tab OR

• You’re curious to read about some of the tactics I’m trying

Let’s get tactical. If you’re weighing up a career decision, here are prompts I’ve found useful.

Where does your mind wander on holiday?

When you’re away from your day-to-day, where does your brain go to recharge its creative juices?

I’ll admit, I’m terrible at beach reads. Many years ago, as I laid on a picturesque beach in Portual, I found myself pulling out ‘Design is a job’ by Mike Monteiro. A book on design ethics and moral frameworks for design leaders. Of course, my wife laughed at me. But at the time I had recently transitioned into people management and felt deeply inspired by soaking up as much of the literature in this space as I could. This was energising for me.

I wouldn’t recommend business books on holiday, but if you reach for one anyway, ask yourself: Why this? What’s it nourishing in you?

Lean into what expands you vs contracts you

You’re probably familiar with the idea of reviewing your calendar for what activities bring you energy or drain you. If not, here’s a great overview from Carly. I’d highly recommend trying it. But depending on the amount of reflection you have space for, there’s a risk of focusing too heavily on the surface-level, short-term feeling, rather than long-term sustainability.

For comparison, let’s consider going to the gym for the first time. That first day probably feels extremely draining and unfun, but give it enough time and momentum and there’s a good chance you’ll be on track for it to feel energising for you. In other words, how comfortable you already are with the activity has a large impact on how energising it can feel afterwards.

A clearer model for personal growth: Which activities expand you, and which ones contract you? Going to the gym for the first time might still feel draining, but approaching the activity with a gentle, growth-oriented mindset can help position this experience as ‘expanding’ your future growth.

Where possible de-couple your current environment from your next move

Beyond the job itself, context matters. Your environment—ways of working, team support, org culture—shapes how work feels.

In other words, an activity you find energising or draining in one context can be the opposite in another.

I’ve seen this in folks who jumped from big tech to startups but miscalculated the lack of support they’ll get in hiring or growing their team; or from founders joining scaling companies who miss the total autonomy they didn’t realise they craved.

Another layer is the influence your calendar plays. Back-to-back meetings make it hard to know what’s truly rewarding, and what just offers momentary relief from stress.

It’s great to try new roles of course, but if there’s even a hint that you could be over-correcting, it’s worth leaning into that feeling as part of deciding your next step.

Type 1 vs Type 2 fun

On a recent podcast Monzo CEO, TS Anil explained how he thinks about Type 1 vs Type 2 fun. I’ve only respect and admiration for TS, and his analogy really resonates on this theme.

Essentially, Type 1 fun is something immediately and obviously fun, like laying on the beach or eating a delicious snack. Type 2 fun can feel more challenging in the moment but leads to longer-term ‘fun’ in the future and a richer life story. For instance, skipping that Netflix show to train for a marathon or staying inside to write another chapter of your novel while missing the beautiful sunshine outside.

Both types of fun matter. But Type 2 fun is often most nourishing for the future you want.

Decide with your body

“If you find yourself caught up in your head, get into your body”

This wisdom comes from Vuokko, my pal and former partner-in-crime (so to speak) at Monzo. It’s a mantra I increasingly find myself reaching for when there’s a big decision to work through. Whether it’s long walks through the forest or a speedy 5K before the kids wake up. I find that getting my body into a state where my intuition can flourish makes decision making infinitely easier. Decisions I’ve been weighing heavily quickly come into focus and start to ‘snap to grid’. Another Vuokko-ism for when the boundaries around a decision becoming clearer and more aligned (or misaligned) to the larger system you’re making sense of.

Interview yourself

Of course, there’s always a way to incorporate AI. Especially when it comes to vibes.

The tactic I’ve found most helpful in working through big decisions is having it interview me in voice mode. I’ll explain the decision I’m looking to make, as much context as I can, and then have it ask one question at a time to help me work through and unpack which path feels most intuitive.

I find voice mode much better at activating intuition because it encourages your immediate stream of consciousness, not a blank page with your inner editor popping out from behind your shoulder to sense check every word.

Don’t expect AI to give you the answer. Use it as a mirror to hear yourself more clearly. Of course, you can also do this with an actual human too, but AI is often the quickest path to getting unstuck and building forward momentum.

Key takeaways

To recap, here are six tactics to try the next time you’re making a big career decision:

1. Tune into your intuition during downtime

   1. Ask yourself: Where does your mind wander when you’re on holiday?

   2. Reflect on the books, ideas, or topics you gravitate toward when you’re not “supposed” to be thinking about work, they might reveal where your deeper interests lie.

2. Map what expands you vs. contracts you

   1. Try this exercise: Review your calendar and activities to assess which ones feel expansive (growth-promoting) vs. contracting (limiting).

   2. Distinguish between what drains you now but expands you long-term (like going to the gym) and what drains you full stop.

3. Separate the work from the workplace

   1. Ask yourself: Is this activity inherently draining, or is it just this context?

   2. Consider whether the environment—culture, support systems, calendars—is skewing your experience of the actual work.

4. Reflect on your personal “fun” mix

   1. Ask yourself: Am I investing enough in Type 2 fun, the kind that leads to longer-term fulfilment?

   2. Make conscious trade-offs between short-term comfort and long-term reward in your career and side projects.

5. Make decisions with your whole body

   1. Try this practice: Go for a walk, run, or movement session to help decisions ‘snap to grid.’

   2. If a choice feels like a ‘whole body yes,’ it’s probably worth paying attention to.

6. Use voice to bypass your inner editor

   1. Try this prompt with AI or a friend: “Can you ask me one question at a time to help me work through this decision?”

   2. Talking out loud (especially in voice mode) helps bypass overthinking and lets your intuition surface more naturally.

You made it to the end! I appreciate you! Until next time,

— Tom

What began as a way to create a little structure, direction and accountability rapidly unfurled into a group expedition for six AI-curious product makers. Design friends who I’d been increasingly chatting with about AI’s tremendous possibilities and terrifying potential pitfalls.

The brief was simple: Ship a project. On your own. In 4 days.

We’d meet every day to check in on progress, plans and reflections. We’d share our demos and learnings at the end.

Essentially, a hack week, themed around using AI to help us all gain a more immediate understanding of how these tools will change and accelerate how we work.

AI is everywhere

We can read the hot takes and chase every new tool, but nothing helps you understand this stuff better than building something yourself.

Yes, there’s Ghiblification and action figure characters, and that former coworker who vibe-coded that impressive project, but how does this really impact your own process?

As the week unfolded, I quickly realised two truths:

1. AI isn’t quite there yet. I lost hours caught in loops just trying to name folders in Xcode. All the hype I’d seen online suddenly felt very far away.

2. But when it works, it really amplifies existing skills. With a clear idea of what you want to build, and a bit of persistence, it can massively accelerate your workflow.

The key to all of this is having a clear vision of where you’re trying to get to and consistent trial and error to iterate toward the future, spotting the endless loops as they emerge and unblocking yourself to move past them.

Scope and iteration

The project I chose was an app to deepen the connection between a parent and their children through a series of short prompts that are randomly chosen when you open the app.

Because it was simple I thought this a good case study to try making an iOS and Apple Watch app.

I’m no software engineer but I’ve written code in the past and am comfortable getting my hands a little dirty.

But I’d never even opened Xcode before.

I figured if AI tools really were the magical superpower I hoped they were, this would just be a small bump in the road. But after spending most of the first two days running into frustration after frustration in Xcode, I hit a wall. That was when I turned back to the group, and their tools, shortcuts and suggestions helped me gain fresh perspective and change my direction. Switching to a simpler web stack wasn’t just a technical change. It was a shift in mindset, sparked by hearing how others were working through their own roadblocks.

From here my progress accelerated massively. Replit was my tool of choice, enabling me to write as much JavaScript in 30 minutes as would have taken me a day or two before. I loaded in a CSV, selected a random row, loaded the data, added basic animations etc. Nothing super complex, but I understood it all.

The hare and the tortoise

AI’s promise encouraged me to start with large ambition and nothing more than a prompt. As I pecked away at the keyboard, sharpening my prompt as the real-time feedback wasn’t getting me exactly what I wanted, I started to realise the missing building blocks weren’t actually words after all. They were things like:

• A simple colour palette and typography system.

• A wireframe or diagram to show how different parts of the experience should fit together.

• A simple illustration for style and placement.

While AI can do remarkable things with a simple natural language prompt, the real value is in finding the fastest route to clearly communicating your ideas. As someone with a design background, this is often far quicker by drawing or making something in Figma that AI could then help bring to life.

In our group reflections I kept coming back to the old fable of the hare and the tortoise. While I’d entered this week expecting to be the hare, sprinting straight to the finish line, I actually found most progress when I approached problems as the tortoise, taking the time to clarify simple design artefacts before AI could rapidly accelerate things from there. Perhaps a tortoise with a jetpack is a better analogy.

Learning together, as we went

The accountability and structure were wonderful. I created far more space to explore AI tools than I ever would have done on my own. But the real value came when I got stuck. Seeing how others pushed through their challenges, whether by changing tools, rethinking their prompts or simply talking through the problem, helped me look at my own blocks differently. I stopped seeing them as dead ends, but as inspiration to explore new avenues.

My favourite two:

• Speech-to-text. Tom inspired us all to try speaking to our computers as a method of accelerating typing speed, and getting more into the flow of truly ‘vibe-coding’. While this took a little getting used to there, I can definitely see the potential. But not in the way I expected. AI works best when it has a ton of context, beyond the specific request you’re making. So being able to regularly brain dump everything on your mind in relation to an instruction you’re about to give seemed to significantly improve the chance of this leading to the sort of outcome you had in mind, even if it feels quite haphazard in giving this direction.

• Just use Replit. Noam suggested using Replit. Others agreed. On the spectrum of vibe-coding tools it’s toward the more accessible end, but it was incredibly quick to get something live at a URL I could share with people. At this point, since I was building a website, it was also very easy to step in and make manual edits when I needed to. The complexity hadn’t been abstracted away too much.

But overall, there was the feeling of figuring this out together, poking holes and pushing AI into unfamiliar territory with others who’d gain from that experimentation too.

What we built

And of course, here are the projects we built.

• Digestible News Web App. Chris built a web app that pulls articles from the NY Times and Guardian APIs, summarising them into digestible bullet-point cards using AI.

• Tiny Sparks. I built a web app for encouraging thoughtful conversations between parents and children, with AI-generated prompts and character illustrations. Replit Link.

• Pocket-to-Podcast Chrome Extension. Tom built a Chrome extension that saves articles, uses OpenAI to generate a podcast script, and Eleven Labs to create an audio version, hosted via Buzzsprout. Chrome store link

• Mighty Veg. Noam built a mobile-optimised Veggie Recipe Converter web app that takes photos of meat-based recipes and suggests vegetarian substitutions, complete with AI-generated ingredient illustrations.

• React Native Birthday App. Jonny built a React Native app that connects to an API to store birthdays, notifies users, and features tab navigation and styling with AI-assisted token design.

• HealthApp Screenshot Library. Liam built a FlutterFlow-based web app to upload, categorise, and tag mobile app screenshots with AI-generated descriptions and filters.

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What’s next?

Will AI change everything? Probably. But the only way to find out what that means for you is to roll up your sleeves and try.

Don’t wait for the perfect tool or the perfect moment. Pick an idea. Set a timer. Gather your crew. See what you can ship in a week.

You’ll be surprised how much further you go when you’re not going it alone.

Big shout out to Gary Chou’s Gather Your People, which has long inspired me to try a group format like this.

One day, someone’s celebrated with a fancy new title, and from the outside, it can seem like it just… happened. Like it was decided on a whim, that day, by an enthusiastic manager.

But in growing companies, that’s rarely the case. Promotions aren’t spontaneous. They’re built over time, win by win.

This post is for ICs and Managers who want to take more ownership of that process, especially in environments where their manager is spread thin, or just juggling too much right now. And in 2025, let’s be honest: where isn’t that the case?

It’s most relevant for companies operating at scale and larger tech orgs where levels, frameworks, and formal processes exist, and where promotion cases require clear evidence and coordination. That said, it’s likely useful earlier than you think, especially as teams mature and expectations rise.

Disclaimer: I’d suggest reading How to Grow Your Career Without Chasing Titles first, because a promotion might not get you what you’re looking for anyway. But assuming you’ve read that, let’s get to it…

A few truths about getting promoted

Let’s start by anchoring on a few key realities:

• Promotion cases need evidence of impact: They’re not given for effort or tenure, but for consistent performance that maps to the next level. That evidence needs to be shown.

• Your manager needs conviction: Even the most supportive managers need to build and champion a strong case. Often to senior leaders or committees who don’t work with you directly.

• It’s a long game: Promotions should never be surprises. They’re the result of consistent performance and regular manager check-ins to shape a coherent story together, often over a 6–12 month period.

And a couple of expectations to set:

• For many, reaching ‘senior’ is a natural and fulfilling landing point. There’s huge value in a strong team of seniors. Not everyone needs to go beyond this, and that’s totally ok!

• The time between promotions grows with seniority. While it might be reasonable to expect to go from associate to mid-level in a year or two, going from Senior Manager to Director will take much longer, often involving a far more nuanced picture of what this looks like for you and your organisation.

A 5-step process to build your case

Sure, the best time to start was six months ago. But today works too.

Whether you’re a manager supporting someone or an individual owning your growth, this is the lightweight process I’ve found most effective for building clarity, structure, and momentum over time.

It’s gone through many iterations. It started out almost entirely focused on goal setting, but over time, I’ve learned that lasting change comes from something deeper: strengthening the muscles around ongoing alignment, and building evidence together.

1. Set a 6-month growth plan

Start with a dedicated 1:1 to talk about longer-term goals and career development.

Managers: this is your opportunity to ask an important question to open the door and start aligning on expectations:

“Is a promotion something you’re hoping for or expecting over the next 6–12 months?”

If you’re the managee driving the conversation, you might like to follow that up with something like, although bear in mind this will likely require some thoughtful consideration from your manager before getting back with a clear answer:

“What would it take for us to feel confident submitting a case in six months?”

From there, define 2–3 focus areas that:

• Reflect attributes expected at the next level in your progression framework

• Close any current gaps or signal clear readiness

This gives both sides a shared understanding of what success looks like and creates a foundation for regular reflection.

2. Keep a weekly win log

A running brag doc that captures evidence of outcomes, output and key milestones throughout your work provides the backbone of this approach.

• Take 5 minutes at the end of each week to jot down wins

• Map them to the focus areas you agreed on in your growth plan

This becomes your source of truth over time and makes it easier to write your case later. And since you’re the one updating it, it positions you to drive the conversation with your manager.

3. Do monthly check-ins

Once a month, review the win log with your manager as part of your regular 1:1s. This helps:

• Stay aligned on the promotion trajectory and likelihood

• Surface wins or impact that might otherwise go unnoticed

• Avoid last-minute scrambling or misaligned expectations further down the line

It turns the process into an ongoing conversation, rather than a single point-in-time decision.

4. Build the promo case early

After a few monthly check-ins, assuming things are on a positive trajectory, start pulling together a draft promotion pack. Most companies at scale will have a template for this, but if not, here are some areas to include:

• Outcomes: consistent evidence of the positive impact you’ve driven on the business or customers in ways that reflect the level of depth or breadth required of the level you’re looking for promotion to.

• Outputs: consistent evidence of delivering at the pace and quality expected from the next level.

• Influence: evidence that you’ve built trust and support from some cross-functional stakeholders and senior leaders, who’d back your promotion decision.

If you’re the managee, you can offer to write a first draft for your manager to react to. Not as a demand, but as a thoughtful step to save time, build clarity and alignment.

5. Submit the case (manager)

Ultimately, your manager owns this step. But by laying the groundwork together, they’re better equipped to confidently and effectively advocate for you.

To recap—

Using AI as your case-building assistant

AI won’t get you promoted, but it can support you in doing the thinking work required to get there.

Here’s how to make it a true partner in your promotion journey:

Translate your growth plan into examples

Feed your progression framework into a prompt like:

“What kinds of work or impact would show I’m operating at this level?”

While this is always worth clarifying with your manager, this can help you define the kinds of evidence to collect each week.

Summarise your win log for check-ins

Each month, paste in your notes and ask:

“Summarise these wins into a clear impact report, grouped by the three growth areas.”

This helps focus check-ins on the evidence, positioning you and your manager as partners in spotting gaps and building up your case together over time.

Draft or stress-test your promotion case

Prompt it with:

“You’re on a promotion committee. Based on this evidence, what’s missing or unclear?”

or

“Write a concise, persuasive summary of this promotion case, focused on business impact, influence, and consistency.”

You can refine it later, but this helps get unstuck and spot weaknesses early.

Reducing the manager bottleneck

It’s worth saying: your manager might deeply want to support you, but many senior leaders juggle a huge range of responsibilities and may not have the capacity to make this their number one priority right now.

That’s why proactively building the case with them is one of the most powerful things you can do. It’s not about forcing their hand, it’s about partnering together to build a case you both feel aligned around.

You can help by:

• Keeping your growth plan and win log up to date

• Offering context on behind-the-scenes influence or cross-functional wins

• Drafting a first version of the case to make review easier

• Bringing questions and reflection to your check-ins, not just updates

Also, your manager may be thinking about the broader implications of your promotion, like:

• How will this person’s role or responsibilities evolve at the new level?

• What work will they step away from—and how will that be covered?

• How does this affect team structure? And can we actually accommodate a promotion to this level?

You don’t need all the answers, but offering some early thoughts shows maturity and forward-thinking.

Final thoughts: Build the case before you need it

Promotions aren’t granted. They’re earned, and clearly articulated. And that articulation doesn’t happen overnight.

By setting direction, logging wins, and creating regular space for feedback, you build the conditions for a strong case. And with AI as a tool, you can sharpen your story, stay organised, and reduce the friction in a process that often gets left too late.

This isn’t about going around your manager. It’s about meeting each other halfway, and building momentum together.

You’ve got more control than you might think.

But when it comes to leading teams, especially at scale, there’s nuance in how to channel this impulse—and some counter-intuitive wisdom—to add the most value to your team overall.

Let’s dive in.

When someone is underperforming, it’s obvious. Maybe they miss deadlines, struggle in critiques, or they’re just visibly stuck. It can be tempting to jump in 1:1 and coach them through their challenge. But there’s a hidden cost. Every hour spent here is an hour not spent helping your strongest contributors thrive.

By definition, your strongest performers are often independent leaders who don’t need your attention. They create great work that drives important business outcomes without you. Think about it—when was the last time you put real effort into making your highest performers even better? Do they get your best coaching, or do you mostly just get out of their way?

I was reminded of this during a recent 9-box talent mapping exercise with a client. Which, if you’ve not come across it before, is a useful tool for assessing performance and potential across a team, although it’s key to work through with an HR partner or experienced colleague to make sure you’re checking for unconscious bias throughout. This post isn’t about the tool itself—it’s about what comes next following any sort of talent review.

Leverage and Opportunity Cost

A recent coffee with a friend reminded me of a parallel in business.

Let’s say you invest £1M in two companies.

Company A is struggling. It’s clear they need help, and you’re able to deliver exactly what they need. If you focus your attention here, you’ll get them to a reasonable level, enabling them to reach a £10M exit.

Company B is excelling. They’re hitting all their goals. They don’t need your help, but you can always find ways to add value. They’re on track to reach £50M, but your help could help them unlock a £100M exit.

Which would you choose to focus on?

While there might be other reasons to choose company A, the economic upside is clearly much stronger in company B.

The same principle applies to teams: we tend to pour energy into the areas that feel like fires to put out, but the biggest unlocks often come from fine-tuning what’s already working. This may feel counter-intuitive at times, but is often where your greatest leverage lies.

What Top Performers Actually Need

You might assume your top performers don’t need much. They deliver great work, hit their goals, and don’t ask for much support. But in practice, they still have untapped potential, and your involvement could make a bigger difference than you think.

Here are a few ways to unlock more from them:

• Clarity and direction – Even the best people need an outside perspective. Perhaps there’s simply too much ambiguity slowing them down, or they’re a little removed from the bigger picture and how their work connects to it. If they’re moving fast and delivering, it’s worth asking: are they spending their time on the highest-value work? A tiny course correction could unlock an even bigger impact.

• Personalised recognition – High performers may not ask for much, but understanding how to recognise their contributions in ways that resonate for them will make a huge difference in how they feel seen and valued. This could be as simple as regular shout outs, but if they’re consistently exceeding expectations why wait for the next performance cycle to update their pay or titling to reflect the value they add?

• Growth opportunities — Just because someone’s great at 0 → 1 discovery work, doesn’t mean they want to spend all their time doing these sorts of projects. Understanding the type of work they’re most excited by and where that intersects with what your team needs can be a powerful combination for creating fresh and exciting new challenges for your best people.

• Fewer distractions – While there’s a natural instinct to give these folks more. More responsibilities, projects or tasks. It’s essential to remove from their plate too. Taking away non-essential commitments can reduce the risk of burnout and maximise the value delivered to your top priorities. It can also be a great opportunity to level up those around your top performers through delegation.

Of course, not every high performer needs all of these things. But your job is to listen and understand what drives and motivates everyone across the team, especially your best people. Don’t just assume they’re fine because they’re doing well or not raising frustrations directly with you.

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How to Help Folks Who Are Struggling, Without Letting It Consume You

Struggling team members need help too of course. And all good leaders should absolutely find the best ways to support them. But there’s an opportunity to be intentional in how you do this, so that you don’t become the bottleneck.

Instead of defaulting to more 1:1 time, consider the following structural changes:

• Change the project. Are they on a project that plays to their strengths? It could be the type or stage of the work. If not, could a project change unlock better results or build their confidence?

• Change the team. Are they working well with their peers or would changing this up unlock new perspectives or growth?

• Targeted training or coaching. Is this a skill gap or misaligned expectations? Some gaps are coachable or could be closed through targeted training, others might indicate a more fundamental mismatch.

• Senior mentorship. Are they overwhelmed by ambiguity, complexity or a new domain? Pairing them with a seasoned IC might be more effective than doubling down on manager check-ins.

• Reset expectations. Are they clear on their priorities and responsibilities? Resetting expectations together can help clarify the path forward, especially when they’re included as an active part of the process.

• Help feedback land. Do they take feedback well? If not, dig in and really understand how to help feedback land for them, because without this it’s much harder to enable progress.

But my favourite question to consider in situations like these is:

What action would you take if you were about to head out on a 3-month sabbatical?

I like this because it forces you to adjust the environment and support structure surrounding an individual, and removes the dependency on you as a requirement to making this work, along with the risk of becoming a micromanager.

While you can always help 1:1, freeing up your commitments positions you to adapt as needs change, ensuring you’re consistently able to drive the greatest impact for your team. Because you’re the only one who really knows where the biggest opportunities are to drive improvement.

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How to Allocate Attention to Your Team

The instinct to help where things are breaking is understandable. But if you want to maximise your impact, ask yourself:

• Where do my strengths have the greatest leverage?

• Where is my involvement unlocking the most value?

• Am I spending time where my team is already delivering great work, or only where things feel broken?

• How can I be proactive about enabling my highest performers, rather than assuming they’ll figure it out on their own?

And one last thing: be kind to yourself. It’s easy to finish any talent mapping exercise and feel like you’ve failed some of your team. If someone isn’t thriving, it must be because you didn’t set them up for success. Maybe. But leadership is complex, and you can’t control everything. Instead of dwelling on what you should have done, ask yourself: what have I learned that I can apply next time?

Further reading

• Katie Dill’s post on Recognition Languages. A fantastic framework for how to understand what drives folks on your team, inspired by the classic Five Love Languages book.

• Claire Lew’s recent post: The Hidden Ways Leaders Unintentionally Punish Their Top Performers. A deeper dive into this theme.

• Pros & Cons of the 9-box talent mapping exercise by CultureAmp

“How do I reach lead/staff/director level?”

It’s a question I was often asked as a manager too.

My answer?

Unfortunately, there’s no silver bullet. What I can offer are a few prompts to help you reframe the question and work through what growth looks like for you, and a thought partner to explore each avenue that opens up.

Let’s unpack three elements:

1. Remove the Job Title

“Wait, didn’t I just say I want to reach ‘lead/staff/director’ level?”

Job titles are just shorthand. They don’t translate directly between companies, and they don’t guarantee higher pay, more influence, or fulfilling work. While early in your career, a ‘senior’ prefix can be a useful horizon to aim for, but at higher levels, growth becomes more nuanced.

Instead of focusing exclusively on a title, unpack what meaningful growth looks like for you. The title might follow, but it’s an outcome, usually beyond your control, not the goal itself.

2. Stack Rank What Matters Most

A tool I often use in early promotion discussions is a variation of Katie Dill’s recognition languages. I ask folks to take some time on their own to re-order the following list based on the question: If I could change 1–3 things for you right now, which would be most important?

• Higher salary

• More equity

• Increased responsibility

• Greater influence or status

• More business impact

• More autonomy

• New skills or experiences

• Different projects or teams

• (A more senior job title)

When we meet to discuss I’ll often ask questions to understand why and what meaningful improvement would look like in each high-priority area. This helps both sides clarify what’s really driving an individual’s growth ambitions, and often leads to a number of practical steps an individual can take to move in this direction. And sometimes, the best next step isn’t a new title at all.

While this is a valuable management exercise, I’ve found it even more valuable for the individual. Many folks have rarely thought about their career growth in this way, but going through the process can bring a stronger sense of control and ownership for a path forward that feels more tailored and personally meaningful.

3. Are You in a Season to Broaden or Deepen?

Early in your career, the goal is breadth. You’re building a strong foundation across various skills. But beyond ‘senior’ growth often shifts toward depth, going deeper into your strengths, to raise the bar or level up those around you.

Understanding whether you’re in a season of broadening or deepening helps you focus your energy. If you don’t define this, your growth may end up shaped by what your company needs rather than what’s energising or meaningful to you.

Throughout your career, you’ll move between these modes. At each inflection point, ask yourself: “What got me here won’t get me there—so what do I need to change?”

Hey, I’m not saying promotions are bad. If it happens, fantastic. But advancing your career isn’t just about a linear series of titles, it’s about defining what meaningful growth looks like for you. By shifting your focus from job titles to what’s personally meaningful, you’ll gain clarity, control, and a stronger sense of conviction in the direction you’re taking.

Plus, different companies value different things, especially at their most senior levels, so spending years reaching the next level at company X may not translate directly to company Y or Z.

Whether you’re in a season of broadening or deepening, the key is to be intentional. Stack rank your priorities, identify where you want to grow, and align your next steps accordingly. The title may come, but more importantly, you’ll be shaping a career that’s fulfilling on your terms.

And if you’d like a thought partner to help you work through what your next step could look like, I’m always happy to chat :)

A quick note to say that February is almost over! And so are my limited low-cost, high-impact coaching and advising slots.

So if there’s a thorny challenge you’d like help working through together, sign up now. As of writing, I have 3 slots left. All next Thursday.

“You sound like a robot”

I remember this feedback vividly. It was 2016. I was sat in BuzzFeed’s New York office. Long before failing Bluetooth headphones literally made me sound like a robot, and before AI was part of our everyday lives.

The feedback was expertly delivered by Cap and Sabrina, about a first draft of a post I’d written to share our design process with the world. It hit hard because it resonated so deeply. A blind spot immediately illuminated as my brain reached the end of the sentence.

As David’s excellent podcast has since taught me, business writing sits at the intersection of clarity & character. While the BuzzFeed post was clear, the lack of character made it a slog to read and sucked all the joy from the work that went into the project behind it. And ultimately, although I’d written them, the words on the page didn’t sound like me.

Perhaps this is the designerly tendency to hone an artefact to its simplest form? Or a fear of exposing my own vulnerabilities and distracting from the purity of the ideas I’m trying to communicate?

Either way, over time I’ve learned to push back on these instincts, building confidence in sharing my ideas in writing. Whether that’s in weekly team updates shared on Slack, the rallying call to action on a new project, or a challenging milestone the team is up against.

As AI becomes increasingly infused in our daily interactions, I’ve been reflecting on how it fits into my writing process—and how it impacts the way we communicate as design leaders. Our impact isn’t just measured by the work our teams ship, it’s shaped by how well we communicate our ideas, influence stakeholders, and rally teams around a vision. Writing is one of the highest-leverage tools for this. But as AI changes how we write, how do we ensure our words maintain clarity and character?

While clarity, and AI’s role in simplifying, reducing, and summarising is evident, what’s AI’s impact on character? Because averaging out the entirety of human thought ever published on the internet has a tendency to, well, remove character.

What is character? Here’s how I see it—

In the context of writing, character makes words feel human. And in a world that’s increasingly mediated through or written by AI, humanity is the unique strength we bring to the table. That’s how our best ideas land, how we build trust, and how we deeply connect with others.

So how might we use AI to enhance character in our writing? Rather than remove it? While nothing replaces the thinking process, I’ve found these four tactics increasingly useful at enhancing or unblocking my writing process.

1. AI as Autotune

Ben recently shared a neat analogy: writing with AI is like Nike releasing a new pair of trainers that make most people better runners. The thing is, now everyone runs the same speed, finishing at the same time. No one stands out. I like where this is heading, but there’s some nuance that I think suits a more musical analogy: Autotune.

Antares released autotune in 1997 and since then, most pop records include some amount of it. It’s not always obvious, or front and centre, but it’s a tool producers can inject at key places to improve the flow of a song.

Used sparingly, it can recover bum notes from otherwise great vocal takes. Highlighting artists at their best by lifting the weakest parts of their original recordings.

And yes, it can also be used overtly, throughout entire tracks as a feature, but there are few artists who are able to pull it off, so unless you’re Cher or T-Pain, this might not be the best move.

Takeaway: Where are the points in your drafts that you’re least confident, where targeted AI improvements could raise the floor, better showcasing your voice or perspective?

2. AI as Audience

A tip that’s helped me write with greater honesty and personality, is to imagine writing an email, to a specific person, answering a specific question they’ve asked me.

AI tools can help scale this. What are the characteristics of the people you’re writing for? What sorts of questions will they ask?

Whether it’s a custom GPT or part of your prompt, you can use AI to share writing drafts and ask questions from the perspective of your reader. Rather than automatically correcting it for you, this helps reveal opportunities for you to take action.

Here’s an example prompt:

You’re Head of Design at a growth-stage product company with a small but high-performing team, mostly made up of product designers. While you’re getting great feedback from the exec team, you lack confidence in your ability to scale yourself and design’s strategic impact across the organisation. You've been playing around with AI and are exploring ways to use it to level up you and your team’s visibility.

- How valuable do you find the following post on a scale of 1–10?
- If you had 30 seconds to read before your next meeting, what’s your top takeaway?
- What's one question you'd ask that this post didn't answer?

<copy and paste your writing>

If you don’t have a specific audience in mind, AI can help brainstorm the kinds of questions different folks might ask. For instance, the commercially-oriented general manager who needs to see expected impact on core business metrics before considering anything else about a new product suggestion.

Takeaway: How can AI feedback help you address your audience more precisely, and build confidence that what you’re sharing will add value? Whether that’s for your team’s weekly meeting, internal stakeholders in Slack, or publicly in building your employer brand.

3. AI as Interviewer

A simple trick: talk it out.

Know roughly what you’d like to write about but struggle with where to start? Have AI interview you. Here’s an example prompt:

You're a podcast host who specialises in A, with an audience made up of folks like B & C. You've invited me on to talk about D. You'll ask me 5–10 specific questions, plus any follow up question based on my answers. Ask one question at a time and pause while you wait for a response.

Take this up a level by using voice mode, but plain old text works too. The key is using specificity (and low stakes) to make it easy to get the ball rolling. And lean on the AI interviewer to take the session in a way that aligns with the direction your audience’s thoughts are likely to drift.

By the end you won’t have a full post ready to go, but you’ll have fleshed out a bunch of ideas, giving you a draft of nuggets to pull from.

A simpler form of this is transcribing a humble voice note. Most days after lunch I’ll take a short walk to collect my thoughts and make a plan for the afternoon. Sometimes this takes the form of outlining a piece of communication I need to write, whether a blog post, a follow up message or a proposal. This method can feel like a more natural starting point, especially when sitting in front of your laptop can feel like a distraction magnet.

Takeaway: When a blank screen doesn’t work, talk it out. Whether sat in front of your computer or outside, walking. Experiment with specific prompts to reach more authentic depths in your own thinking.

4. AI as Average

I think most people would agree that AI knows average-quality writing. But by asking it write for us, are we missing the bigger opportunity? Knowing average-quality writing is an invaluable tool at helping us understand where our writing is average-quality, and where we can inject humanity and character to bring our words to life.

Let’s return to our formula, and write another AI prompt:

Character = Personality + Perspective + Vulnerability (+ Taste)

You're an online design publication editor. Your most successful articles are determined by the human connection they build, not just the information they convey. Give the following piece a score out of ten and the following feedback:

- Personality: what facts or personality traits do you know about the author from this piece alone?
- Perspective: where does their insight or point of view differ from the general consensus on this topic? 
- Vulnerability: aside from writing ability, where are this person's flaws that reveal their humanity?

<copy and paste your writing>

You may have noticed the word ‘taste’ snuck in here. While it sits alongside these qualities, it’s perhaps the hardest thing for AI to replicate. As many have talked about, it’s increasingly becoming one of the most rare, valuable, and innately human qualities we bring in an AI-oriented world.

And it underpins all four of these tactics too. While I recommend giving these a whirl, at the end of the day whatever you write needs to feel natural to you. And while AI can open up valuable avenues to explore, it’s ultimately down to you to choose what you put your name to.

Takeaway: Flip generative AI’s mediocre writing knowledge into its superpower, by helping you see where to add more humanity in your writing.

In conclusion

Why am I writing a design leadership piece about writing? There’s an old meme—which I can’t seem to find—about the tools designers used at various stages of seniority throughout their careers; from production-oriented tasks (photoshop, illustrator, indesign) → strategy-oriented tasks (all the tools) → leadership-oriented tasks (powerpoint)

While the tools and way of working have changed massively since then, the core idea of the highest-value, highest-leverage impact often happening through communicating ideas, is as strong today as it’s ever been. So whether it’s a thoughtful Slack message to the whole company, a persuasive strategy one-pager in Notion, or you’re just looking to build stronger psychological safety with your team through sharing your full self, with vulnerability and empathy. AI is not necessarily the answer, but nor is it the enemy. And used well, it can a valuable tool in strengthening your ideas and enhancing how they land, in ways that feel authentic and true to you.

What are some AI writing tricks you’ve found useful to you and your team? Is there any feedback you’ve consistently been given about your own writing that you’ve used AI to help with? I’d love to hear your thoughts.

Now that I’ve had a moment to reflect, I wanted to share a few lessons that stuck with me. The ideas and principles I’ll carry forward. I hope these might be useful to others navigating the ups and downs of scaling products and teams too.

1. Execution creates momentum

I learned many things from Mike. One of the simplest was perhaps the most profound: shipping is your heartbeat. On the surface, this means regularly shipping updates to customers, learning from feedback, and iterating on the product. But on a deeper level, it’s about creating rhythm and momentum—moving forward in ways that align, energise, and build confidence across an entire organisation.

Shipping isn’t just about getting things done; it’s about making progress visible. A humble weekly update can build excitement and alignment. Product reviews can be levers to elevate both quality and pace. And for product designers, the work isn’t finished when something looks great in Figma—it’s finished when it’s live to customers, and we’re learning how it works in the real world.

Building momentum across this loop—from idea to execution to learning—builds a natural bias toward impact on customers and the business. It encourages teams to focus on outcomes, not just outputs—on the change they’re driving, not the meetings they’re in, or the artefacts they’re creating.

And execution isn’t just about shipping products, it’s about shipping clarity. As a leader, sometimes the most important thing you can ship is words: a decision, a reframed question, a narrative that brings focus to a team.

Questions to consider: Where is the friction in decision-making loops in your organisation? Which areas would clarity or prioritisation enable faster-moving teams? Where could leadership model a ’shipping’ mindset by making their decisions more visible?

2. Visualising progress is Design’s superpower

Design’s greatest strength isn’t just imagining the future—it’s making it tangible. Strong design work doesn’t just sit in Figma or live in a polished 3-year vision; it shows up in the everyday artefacts that help teams move forward.

It could be rough ideas from a discovery sprint, a nicely visualised diagram that clarifies a major decision, or a quick UI sketch that aligns two adjacent teams. These small, tangible moments make complex ideas easier to grasp and help connect the dots across disciplines. When design is visible and accessible, it has the power to galvanise teams—bringing people together around shared ideas and driving collective progress.

This doesn’t necessarily mean turning design into an internal roadshow, but finding the right format to share work in progress that non-designers can engage with. Whether it’s the designs themselves or the principles behind them. This not only deepens non-designers’ engagement with design but also strengthens its influence on company direction.

At Monzo, Vuokko is masterful at this, curating and sharing the right design tidbits and insights each week to inspire and align people across the business, regardless of their role. The impact isn’t just in the work, but in how it shapes thinking across the company.

Some of the most complex or technical areas of a product rarely see the light of day—but designers can make them clear, exciting, and meaningful. Financial crime, payments infrastructure, operational workflows, these are just some of the product areas I saw engagement spike once designers were added to teams and set up to flourish.

Questions to consider: Is your team set up to influence or just execute? What’s the last design artefact that unblocked a major decision? What qualities made it effective? How might you and your team distill tactics from these examples and bake them into your ways of working across the team?

3. Customer-centricity is a strategy, not just a value

At Monzo, customer obsession is embedded into everything. From the product teams making improvements, to what’s celebrated at company-wide all hands, to feedback in performance reviews. It’s core to Monzo’s mission of making money for everyone, and has been a big factor in hiring some of the most customer-centred engineers I’ve ever worked with.

But the magic really happened shortly after TS took over as CEO. He led the charge in establishing business metrics that concretely coupled customer success with business success, encouraging a win-win outcome-oriented mindset across the company. We win when customers win.

Customer and business success are often framed as a trade-off. Teams feel pressured to prioritise one over the other. You might have X number of teams working on business initiatives with Y teams working on feature improvements for customers, with a ratio driven by how strong the business’ current trajectory is looking. But this win-win mindset empowers many teams with broader ownership over directly driving improvements for customers and the business.

Of course, not every company has a mission that aligns so cleanly with customer success, or the wide-range of potential business models that would enable this possibility. But this is still a useful gut check: when business metrics and customer experience feel at odds, how does this influence the work culture? And what incentives does this reinforce?

Questions to consider: What metrics does your company internally celebrate success and progress with? If customer-centric measures aren’t prominent, what could a customer-centric version be? If there’s tension between these two, where might you have influence to shift this balance?

4. Use time-horizons to make difficult, intentional trade-offs

During the pandemic I was grappling with a seemingly impossible trade-off. I cared deeply about setting the team up for long-term success, but optimising for this in every decision would’ve led to disruption in the short-term, at a time of peak anxiety across the team and the world. A conversation with Sarah led to the insight that it’s ok to bend your own principles if you’re intentional about the time horizon you’re making them over.

One of the key challenges of leadership at a growing company is constantly needing to scale yourself. Some balls will always need to drop. The challenge is identifying which ones will bounce back and which ones will shatter when they hit the floor. But most importantly, which ones unlock your greatest leverage if you prioritise them?

Identifying which is which isn’t always easy. Especially during turbulent times. It’s important to recognise your default biases too. This can help you figure out which areas are worth leaning into and which are worth letting go of to get around the short-term challenge you’re facing.

Questions to consider: Are you struggling to prioritise between two important areas? Write them down. Then zoom out to one month from now, six months from now, one year from now, writing down where you think each will be if you do/don’t give it the attention right now. Viewed through these future selves, which trade-off starts to feel like the better investment?

5. The imperfect art of staffing while scaling—always be learning

“We need another designer. Can they start next week?”

Hiring in a fast-growing company is rarely straightforward. Between recruiting lead times, budget approvals, and shifting priorities, getting the right people at the right time is a constant challenge. And then you actually need to find them.

While having a clear strategy helps increase your chances of getting lucky, the best approach I’ve found is to treat the whole process as a learning opportunity. Key strategies to improve long-term hiring outcomes include:

• Build trust with key stakeholders – Whether it’s a GM or product director, involving them early, setting clear expectations, and delivering consistently helps avoid last-minute surprises.

• Onboard teams together by aligning across functions – Where possible, sync hiring priorities with engineering and product partners to onboard full teams together rather than individuals in isolation. This smooths out overall ramp up time and avoids the more acute pain of “everyone else is ready to go, but we’re blocked without a designer”

• Experiment with flexible staffing – Test models where designers support multiple teams with scoped delivery needs, rather than embedding exclusively within a full-stack squad. It won’t be perfect, but collecting evidence on what works builds long-term adaptability.

If you happen to have the ideal team in place at the perfect time, it’s typically more down to luck—and it won’t last long. Instead of chasing perfection, embrace the discomfort. Capacity constraints force clarity—lean into them, learn from them, and use them to build a more resilient, adaptable team.

Questions to consider: Think back to your top three staffing headaches. Do they share common patterns? Those pain points often signal areas worth tackling to improve your hiring approach.

6. Apply systems thinking to hiring—but keep empathy at the core

Recruiting is hard—not just because great candidates are difficult to find, but because, as a hiring manager, it can consume as much time as you allow.

During my years hiring product designers at Monzo, I learned to approach recruiting as a system. I had the rare opportunity to redesign product design’s hiring process from the ground up before a major hiring spree. Alongside an incredible recruiting partner, Natalie, this foundation allowed us to systematically refine and accelerate hiring, while continuously raising the bar for quality and our candidate experience.

At first, I was involved in nearly every portfolio walkthrough, our first interview step post-screening. But as we strengthened our quality bar and onboarded more interviewers, I moved later in the funnel. Eventually, I was only in hiring debriefs, helping managers challenge assumptions, refine decision-making, and ensure every hire strengthened the team. By that stage, the question wasn’t whether a candidate was strong—I trusted they were. Instead, it was about making hiring decisions with open eyes: How will this candidate shape the team around them?

Strong hiring isn’t just about finding great candidates—it’s about learning as you go. A high-functioning process gathers both qualitative and quantitative data from interviewers and candidates, iterating toward a faster, fairer, and more consistent approach to hiring with conviction. But my true measure of success was the candidates who didn’t end up joining us—could we make their experience strong enough that they’d tell a friend or come back to interview again in the future?

And then there’s performance management and progression frameworks—but that’s a topic for another post.

Questions to consider: Rate your current hiring process from 1–5 (1 = slow, painful for candidates; 5 = fast, fair, and enjoyable). Which interview step adds the least signal to the hiring decision you ultimately make? What impact would removing or improving that step have on your score?

7. Fit is a moving target

Companies evolve. Teams change. What made someone a great fit at one stage might not hold true forever—and that’s totally ok.

Spend long enough in a growing business, and you’ll notice different waves of people joining and leaving; early scrappy builders, growth-oriented scalers, big-tech operators. Each suits a different phase but each brings trade-offs. There’s no perfect team structure—only what works well right now.

The same applies to individuals. The role you loved two years ago might not energise you today. The processes that worked six months ago might feel stale. Some things naturally need periodic resets (design critiques, for instance, often benefit from a fresh approach every 6–12 months). But some shifts run deeper. Recognising when you—or your team—need to adapt is a core leadership skill.

The best role model I had for this was Flora, who resisted the urge to follow the default career ladder for the sake of climbing, instead narrowing her focus and doing what she does best, but better. A reminder that progression isn’t just about moving up—it’s about aligning your energy with what adds most value to the world, and following your instincts.

Above all, this requires self-reflection, kindness and humanity. I don’t see designers as objectively ‘good’ or ‘bad’—only how well they fit (or don’t) the needs of the team at this moment. And when those needs shift, the best leaders help people navigate any transitions with empathy and humility.

Questions to consider: What parts of your role energise you? What drains you? If you stepped back and looked at your team objectively, where do you see misalignment? What conversations could help clarify the best next step for you or your team?

To recap

1. Execution creates momentum – The best teams focus on outcomes, not outputs, and use shipping to drive clarity and alignment.

2. Visualising progress is Design’s superpower – Making work tangible helps teams connect the dots, galvanise momentum, and shape strategy.

3. Customer-centricity is a strategy, not just a value – The strongest businesses align customer success with business success to positively impact both.

4. Use time horizons to make difficult, intentional trade-offs – Know where your leverage lies, and use it to balance quick wins with long-term investments.

5. The imperfect art of staffing while scaling—always be learning – Hiring at scale is never perfect, but embracing constraints can help build stronger teams.

6. Apply systems thinking to hiring—but keep empathy at the core – Great hiring processes evolve over time, balancing efficiency with a strong candidate experience.

7. Fit is a moving target – Companies evolve, teams change, and the best leaders help people adapt with clarity and empathy.

These lessons aren’t definitive answers—just reflections from five years of figuring things out alongside an inspiring group of people. Every team and company evolves differently, but the core challenge remains the same: how to build momentum, make better decisions, and help people thrive as things scale.

What do you think? I’d love to hear from others—what lessons have stuck with you as you’ve navigated leadership in fast-growing teams?

On Monday, I launched February’s low-cost, high-impact Deep Dives. Within days, 15 of the 22 slots were booked. (As of today, there are still 6 left if you’d like to try one.)

The first sessions happened on Thursday. And I loved running them. They feel like a cross between a great product review, an interview, and a coaching conversation—deep listening, structured facilitation, and then serving as a tour guide through the different paths each challenge presents. It’s been a long time since I left a workday feeling this energised. These sessions have been a strong reminder that I’m on the right path.

They’ve also been a great way to learn what people want to work through. 60 minutes is plenty of time when there’s a clear outcome in mind. And if there isn’t, shaping that together at the start increases the quality of takeaways and actions an individual is able to leave the session with.

Refining My Positioning

Through these Deep Dives and ongoing initial calls, I’ve been reflecting on who I’m best set up to serve and how I position myself to meet those needs. Previously, I thought of my work in a binary way—coaching for individuals OR advising for companies. But I’m realising that these lines are often blurry. In reality, both individuals and teams want elements of both.

I’m now exploring a more team-oriented positioning, focused on the outcomes I drive rather than strict role definitions. This means blending leadership coaching with strategic advisory work in a way that adapts as an organisation and its leaders evolve.

I’m also sharpening my view of the companies and leaders I’m the strongest fit for: growth-stage product companies that have found strong product-market fit and are now scaling product lines and teams. It’s not easy. But I’ve spent a lot of time at this inflection point and love the challenges it brings.

Three Learnings From the Process

• Granola is an excellent tool for writing strong follow-ups, but nothing replaces leading with my own synthesis and top 2–3 key takeaways.

• Two weeks’ notice seems to be the sweet spot for announcing and booking these sessions. Thursday, Feb 13th was the first to fully book, within 24 hours of opening on Feb 3rd.

• Good sleep, exercise, and nutrition are essential to sustaining a full day of deep conversations. A helpful reminder to pace myself to ensure the best outcomes for every session.

Emotional Themes From the Week

I asked ChatGPT to pull 10 emotional themes from my journals throughout the week: Excitement, Self-Doubt, Clarity, Gratitude, Tension, Validation, Frustration, Empowerment, Satisfaction, and Confidence. That pretty much sums it up.

Until next time ✌️

No matter how many times I’ve done this, I’m always surprised by how quickly you learn once your ideas are in front of real people. It’s not always conscious feedback—it’s in the context of inbound call bookings or the questions those calls spark. And these questions are gold. They’ve already given me a deeper understanding of my target audience for each offering and the common themes and challenges they face.

Most validating of all has been the number of inbound requests that perfectly match the challenges, people, and organisations I’ve dreamed of working with. Whether or not these become long-term partnerships, I’m increasingly confident the audience and their challenges are real. And I’m genuinely excited about the prospect of working on them together.

Beyond the steady flow of calls and deep-dive sessions, the rest of my week was filled with writing—a craft I’ve grown to love. Not just for my initial Substack posts, but to explore the big topics that have been swirling in my head for months: leadership lessons from my time at Monzo, the impact of AI on leading design teams, and the evolving role of ‘design managers’ in today’s layoff-prone, profit-driven business climate.

Lastly, Monday mornings feel like the most natural time to write these notes. The weekend serves as a natural pause—a chance to reflect, shifting from practical tasks to broader reflection. Not because I spend weekends writing—quite the opposite. Time away from the laptop helps me refine my thinking.

And with that, I’m just happy to be here. I’m glad you are too.

Until next time!

But before we dive in, I want to say thank you. You signed up for this mailing list with little more than a vague promise of “design leadership coaching and advising” and no actual proof to back it up. Yet, for 100 of you, that was enough. I’m humbled and grateful for your support. Thank you.

Alright, back to it.

Introducing: Intentional Partners ✨

🔗 http://intentional.partners

If this is your first time hearing the name—don’t worry, it’s still just me. I created this separate identity to house my coaching and advising work. I chose to name it Intentional Partners because that’s how I work best.

“Coach” and “advisor” can mean a lot of things. What matters most to me is building long-term, purposeful relationships—meeting you where you’re at and evolving our partnership as you grow.

As a coach, I partner with emerging and established design leaders. Whether you’re early in your management journey, leading an entire organisation, or a senior IC figuring out what’s next, I’ll help you navigate leadership challenges and unlock growth—for yourself, your team, and your product.

As an advisor, I help leaders elevate great design within their companies. If you’re a Head of Design looking to amplify your team, a product leader building one from scratch, or need a partner to tackle key organisational challenges, I’ll help you chart and execute a clear path forward.

If any of this resonates, hit reply or book a call. I’d love to chat.

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How I Got Here & What to Expect

The past few months have been a deep dive into self-reflection—reconnecting with friends (many of whom are design leaders themselves), journaling, and refining what’s next in my professional world. My goal was simple: to align the work that energises me with the value I’m uniquely suited to bring. Intentional Partners feels like the natural intersection of those two, so I’m excited to see where this leads.

I’m passionate about supporting the design community. While coaching and advising is the most direct way I can do that, I also want to help those without the time or means to work with me 1:1. That’s where writing comes in.

This newsletter will be a space for thoughtful, longer-form reflections on design leadership today—a mix of big ideas, practical tactics, and maybe a little bit of humour along the way. I intend to write these once a month, but only when inspiration strikes and capacity allows.

I’ve also added a Weeknotes section on Substack. I didn’t auto-subscribe you (or new subscribers) to it, but it’s there if you’re curious. Weeknotes are my way of building a habit of writing in public—small wins, personal reflections, and insight into how this independent path is unfolding. Expect short updates, most weeks. Here’s last week’s. I’ve long admired the practice, so I’m excited to have the right opportunity to try this out.

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That’s it for now. My first longer-form piece is in the works, and I’ll aim to send it next week—keep an eye out.

Thank you for being here. Your support means a lot. 🙏

Tom

I wrapped up a lightweight visual identity centred around a lovely modern 70s-inspired typeface called Nutgame and experimented with Framer for the first time to build a simple website. Wow. It’s like Dreamweaver took a Time Machine into the future. I totally see why it’s so popular—it’s powerful, intuitive, and makes web design feel easy. Until I needed to tweak that one thing, which would take a single line of code in CSS that I no longer have access to. I digress...

The website content is nearly complete. I’m lucky to have wonderful friends who wrote glowing testimonials, and a friend’s video walkthrough helped me see my copy through the lens of the 99% of people who won’t read every word. A great reminder: less is more, and authenticity beats ‘professional’ wording that’s easier to gloss over.

Pricing was mostly locked in, but a trusted coaching pal gave me a fresh perspective, reinforcing what my gut was already telling me. It also helped me to consider a new tier for more established leaders dealing with greater complexity in their organisations. This insight aligned with feedback from an initial call earlier this week—where I learned my rates were ‘significantly less’ than this lovely potential client’s previous coach. Noted.

I’ve been wrestling a little with what to call myself. ‘Coach’ is broad and context-dependent, while ‘Advisor’ feels more directly aligned with my recent full-time role. But I’ve realised a single label matters less than making my approach clear: I aim to be a strong partner to leaders who care about great design. That clarity matters more than the title.

Oh, and I tried using ChatGPT to write these week notes. I fed it a bullet point outline and my journal entries from the week—it was… okay. But week notes like this thrive on vulnerability and authenticity, which ChatGPT struggled to distill. So I scrapped it and wrote everything here from scratch. A fun experiment, at least.

Right now, everything is theoretical. The conversations I’ve had are promising, and I feel conviction in my path, but until I launch, I won’t know how the world will respond. I hope next week goes smoothly, but I’m embracing the idea that uncertainty is the price of entry for forging an independent path aligned with my values.

I can’t wait to see what happens.

Until next time!