A diagnostic talk for founders who sense something’s off with their leadership team and want the right questions to find out what.
The next level of growth won’t come from optimising your product, fundraising, or working longer hours. It’ll come from how you hire, align, and lead the people around you. Most founders underinvest in this, not because they don’t care, but because people problems feel messy, hard to measure, and outside their comfort zone.
You’ll learn how the best CEOs think about people as the beating heart of the business – not cost centres or risks. How can you create a team that moves faster, makes better decisions, and doesn’t rely on you to be everywhere.
A practical playbook for:
- Moving faster by optimising your top team
- Knowing when you are the bottleneck – and fixing it
- Leading with clarity, especially when things get hard
You’ll leave with new mental models, real-world examples, and tools you can apply immediately. Whether you’re hiring your first leadership team or trying to get more out of the one you’ve got, this session shows you how to turn people into your growth engine – not your biggest headache.
Slides
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Transcript
I work with CEOs from early-stage startups through to FTSE-listed businesses. A couple of years ago I was talking to a CEO who told me growth had flatlined. Things were difficult. I asked about her leadership team. “Oh, it’s great,” she said. “We’ve got A players.” She talked me through everybody, and it sounded fantastic, so I asked about the dynamics. “Funny you should ask,” she said. Her salesperson and her product lead hadn’t spoken for two years. They couldn’t be in the same room together. Annabelle came in on Mondays and Tuesdays. John came in on Thursdays and Fridays. Nobody got very much done on Wednesdays.
That’s what happens in a business. You start off with great high hopes about your leadership team, and soon enough you start to tolerate some weird and unusual stuff. What I want to talk about today is how to actively design and intentionally build a leadership team, not just hope one assembles itself.
Why execution beats charisma
This started for me with a book. When I was 14, I found a book on my parents’ shelf called How to Read a Person Like a Book. I was thrilled: I had a school disco coming up and thought I’d finally understand people. It turned out to be one of the most boring business books ever written, but it taught me something real. I wish people were this simple. They’re not.
Since then I’ve spent thousands of hours coaching CEOs, and what’s interesting is that they’re wonderful people, but they all suffer from the same insecurities the rest of us do. After a couple of sessions, they’ll quietly ask me: am I doing this right? There’s no single right way to be a CEO. But there are traits that separate a good leader from a great one.
I interviewed Professor Stephen Kaplan from the Chicago Booth School of Business, who has studied over 5,000 CEO aptitude tests, most of them from Fortune 100 businesses, and correlated the results with performance over time. He narrowed it down to six or seven traits: charisma, IQ, strategy, execution, interpersonal skills, expertise. One of them was the standout predictor of success, by a huge margin. It wasn’t charisma, or IQ, or the ability to run a room. It was execution.
That has a direct implication for how you think about your own role. You’re no longer a manager: managers lead teams. You’re not a functional head either: functional heads lead functions. As CEO, you lead leaders. Even at 20 people, you need leaders under you running each discipline, people who don’t need you telling them what to do all the time. Putting yourself in the position of leading leaders makes your job infinitely easier.
The ten habits of a successful employee
I’ve spent 20 years distilling what separates people who succeed inside an organisation from those who don’t. None of this is original to me. I’ve just collected and collated it from the CEOs I coach. If you do all ten, you’ll do well:
- Get important things done. Have a bias for action.
- Do what you say you will do.
- Only take on what you can complete.
- Always seek to expose truth and reality.
- Build strong working relationships across teams and functions.
- Understand how your company measures value and success.
- Understand how you personally contribute to that success, and do more of it.
- Understand why your company is successful, and do more of that.
- Maintain a positive balance in your value account with the organisation, so when you need flexibility, you’ve earned it.
- Create a portfolio of your personal successes, so you have the evidence when it’s time for a promotion or a raise.
Everything I’m about to walk through is also a guide for pushing your own career forward, whether or not you’re the one running the company.
Great is just being good, repeatedly
The idea I want to leave you with is simple: great is being good, repeatably. Define what good means, then do it again and again. I’ve broken that down into four parts: strategy, outcomes, rhythm, and flywheel.
Strategy: the crisp test
Everybody loves talking strategy. I’ve worked in tech for twenty years, across the world, and the one thing I’ve learned that goes beyond business is this: any movie advertised on the side of a bus is going to be awful. Never go and see a movie advertised on the side of a bus.
I first noticed the pattern around 2010, when I was called in to fix things that weren’t working. I got a call from Best Buy, who were launching into Europe in 2011, advertising heavily on buses. Their website wasn’t converting. I asked about their numbers. Not the number of buses, the numbers on the website. What are you trying to do? What’s the strategy? “We’re going to open 200 stores in the next two years,” they told me. That was it. That was the whole strategy.
Two years later, Best Buy was no longer in Europe. They’d spent about $700 million. “Buying technology in Bristol just got epic,” said the poster. There was nothing in it that told you why you should go. The strategy failed because it never answered why, or how.
After seeing hundreds of strategies, from huge businesses to tiny ones, I can usually tell a good one from a bad one by asking a simple question: is there a crisp definition of what, why, how, and when? Crisp, as the Oxford English Dictionary defines it: briskly decisive and matter-of-fact, without hesitation or unnecessary detail. Best Buy only ever nailed the when. The what and the why were missing entirely.
Get this right, and you can explain your strategy simply to anyone in the business. Companies with a crisp strategy are roughly twice as likely to succeed. It doesn’t need to be a 500-page document.
Outcomes: truth versus survival
The next question is: what are the outcomes that show strategic success? Opening 200 stores isn’t success. It’s not necessarily failure either, but it doesn’t define what success looks like, and it certainly didn’t work out for Best Buy.
I once worked with the CEO of an on-demand funeral business. Seasonal, for obvious reasons: more people die in winter. He called me after a huge argument with his chair, who wanted a workshop on stimulating demand off-season. Effectively, figuring out how to get more people to die outside of winter. You have to accept some seasonality is just how a business works. The chair’s anxiety about it came from somewhere else.
Here’s the question underneath that: have humans evolved for truth, or for survival? Survival, obviously. Emotions exist to help us survive, not to help us find the truth. I sense a tiger behind that tree, I run. That’s the warning system working as designed. When someone you work with, an investor, a leader, is operating in survival mode, they are not going to behave logically. That’s true of PE-backed businesses with a lot of money on the line, and it’s true inside your own leadership team.
You see this most clearly in sales. Take two salespeople, Mark and Alex. Mark was the consummate performer: golf, a yacht, clients entertained in style, proposal after proposal going out, a huge pipeline. Alex spent far more time on each individual prospect, and had a pipeline half the size of Mark’s. Alex closed twice as much business. Mark was optimising for survival, for looking successful. Alex was optimising for truth. Anybody can send out a hundred proposals. Whether a hundred were actually received on the other end is a different question.
Ask two things of every leader on your team, and of yourself: do they value truth over survival or comfort? Do they value outcomes over effort? The best leaders reward outcomes, not hours worked. They don’t pay people for a 60-hour week. They pay them for what that week produced. And the best leaders can explain outcomes crisply, so every member of their team knows exactly what their role contributes to the company’s success. It doesn’t matter whether you use OKRs or something else. What matters is having a crisp, numeric definition of what success looks like, one that’s easy to explain.
The inner game: why leaders clash
After a few sessions, CEOs will often tell me what the job actually feels like. Pushing a car uphill. Spinning plates. A hamster wheel. Everyone looking to you for the answer. One CEO I worked with found the plate-spinning metaphor exhausting, so we looked for a different one. He landed on air traffic controller: sitting with his coffee, nudging planes, telling them where to land. A completely different feeling from constantly managing crises. The way you see the world shapes the world you build. I worked with a CEO who kept the plate-spinning metaphor, and when he ran out of plates to spin, he started sabotaging parts of the business to create more.
Underneath that metaphor is what I call the inner game: your beliefs, your values, your capabilities. I believe hard work gets results. I have these capabilities, I’m the smartest person in the room, I’m the best coder here. All of that folds up into your identity. The trouble starts when that identity gets challenged. Attack someone’s belief, or their values, and it feels personal, because it is personal. The inner game dictates the outer game, our actual behaviour, and the only way to get better at the outer game is to question your own beliefs, values, and capabilities, and to understand the same in the people around you.
That’s exactly what was happening with Annabelle and John, the salesperson and the product lead from the start of this talk. Neither one understood the other’s inner game. Each assumed the other operated from the same beliefs and values they did, and those two sets of beliefs were not compatible.
The part of the brain doing most of the work here is the amygdala, which drives fight, flight, or fawn. When someone’s identity is threatened, you’ll see one of the three: they fight (outbursts, refusing to speak to someone again), they flee (going quiet, avoiding the room), or they fawn (excessive niceness that masks what’s actually going on).
Here’s the single question that gets to the root of most of what’s wrong in a struggling leadership team: are there regular one-to-ones between leadership team members, not just with you, but with each other? If two leaders only ever meet in your Monday team meeting and never one-on-one, that’s a trust problem. I worked with a CEO whose salesperson and product lead weren’t getting on at all. He ran a Friday workshop, then kicked them both out of the building with one task: go write next year’s strategy for sales and product together. They weren’t allowed back until it was done. Walking the city together, with a common enemy in the CEO to complain about, was enough to get them talking.
Rhythm: the fastest fix
Rhythm is the cheapest, quickest thing to fix in a broken leadership team, and it’s usually the first place to look. How often does the team meet, and what happens when they do? If your team meetings are just a download session, everyone reporting what they did last week, nothing is actually happening in that room. Ask whether deadlines and initiatives are drifting. That drift is usually a rhythm problem before it’s anything else.
Flywheel: knowing your own bias
The fourth piece is flywheel. A lot of the founders I coach come from a specialism: engineering, finance, product. I was working with a former engineer, now CEO of a business doing around $4 million in revenue, growing fast, just closed a Series A. Things were stressful. Frustrated that a feature wasn’t shipping, he spent the weekend vibe coding it himself, and came in on Monday expecting the team to be thrilled. They were furious. He couldn’t understand why.
When things get stressful, leaders retreat to their superpower, the thing that got them this far. If you were an engineer, you code. If you were in sales, you sell. If finance, you build a spreadsheet. You’ll hear leaders say “I’m an engineer at heart” or “I’m a product person at heart.” That’s fine, until it becomes a bias that skews the whole organisation toward one function. Look at who most technical founders hire first: another engineer, almost every time. That’s the bias showing up in the org chart. Five or ten years in, most founders wish that first hire had been commercial.
Ask yourself where your bias is getting in the way, and ask the same of your leaders. I used to work with product teams who assumed every CEO wanted to talk roadmap constantly. In practice, I’ve had almost no conversations with CEOs about product roadmaps. The bias exists in some functions far more than the CEO’s actual attention does.
I saw this play out at eBay, where I worked on and off between 2008 and 2012. Every year had a theme: the year of the buyer, then the year of the seller, flip-flopping back and forth, alienating whichever side wasn’t the current focus. Leadership’s philosophy was balance: keep buyer and seller experience even. That metaphor was wrong for a marketplace. While eBay chased balance, Amazon built a flywheel: logistics, next-day delivery, a payment system, an existing customer base, each piece reinforcing the next. Amazon wasn’t balanced. It was compounding. That flywheel ate eBay’s lunch.
The strongest metaphor I’ve found for running a business isn’t balance, it’s flywheel: does what one leader is doing strengthen what another leader is doing? Is value spinning up, or is it static? You only get a flywheel if leaders are meeting one-to-one regularly, and if the strategy has a crisp what, why, how, and when. Everything from the earlier parts of this talk has to be in place before the flywheel can work.
Everything should be a ten out of ten
I’ve put strategy, outcomes, rhythm, and flywheel together into a leadership team canvas: a way to assess your strategy and rhythm as a team, and then each individual leader on truth versus survival, and outcomes versus effort. I’d love your feedback on it.
What most speakers do from this stage is give you answers. I’ve deliberately not done that today. These are questions, and only you can answer them for your business and your leaders.
One last idea. Seven out of ten. The genuinely bad stuff in a business, the twos and threes, gets dealt with. If a feature doesn’t work, you kill it. If someone is dreadful at their job, you deal with it, you don’t tolerate a two out of ten. The real danger is the seven out of ten: the product and sales leads who don’t speak, the salesperson optimising for pipeline over results, the strategy that’s almost but not quite crisp. None of that looks like a two. It looks like a seven, and sevens are where mediocrity quietly takes hold. There’s no time for mediocrity. Everything should be a ten out of ten.
Q&A
Dominick Reed: At the start, you talked about outcome versus effort, and in my head that translates to outcome equals truth equals engineering, versus effort as the other side. Is the real question what I, as CEO, value more? Or is it about how I deal with different people in the organisation?
Joe Leech: Good question. Think about reward, not just outcome versus effort in the abstract. A lot of organisations reward effort over outcome. John worked 60 hours last week to ship a feature. Great, but that alone doesn’t earn him a promotion if it didn’t move the business forward. If you’re rewarding effort over outcome, you’re mistaking progress for activity, and they’re not the same thing. Reward the outcome, not the hours. If you’re an employee working hard and not getting recognised, that’s usually a sign something in those ten habits I mentioned earlier is out of alignment, not that hard work doesn’t matter.
Dominick Reed: Following on from the engineering example: a lot of people genuinely believe the 60-hour build is the outcome. How do I explain that if it doesn’t move the top line, doesn’t bring in clients, doesn’t help the ARR, it’s effort and activity, not outcome?
Joe Leech: If your strategic what, why, how, and when is crisp, and shared across the organisation, people should be able to see how their own role feeds into it. If they can’t, either they’re in the wrong role, or you haven’t helped them see it. You should be able to walk up to anyone in the business and ask how what they do feeds into the strategy, and they should be able to answer comfortably. If they can’t, that tells you the strategy isn’t filtering down, even if it’s clear at the top.
Bruce McCarthy: Adding to that: it’s on every functional leader to explain not just what they want from their team, but why. Not “build this for me,” but “we’re trying to solve this problem for the customer, which we believe will solve this problem for the business.” Debate the ideas on the table, and figure out which ones actually solve for both variables. That’s what I want from a CEO, and what I want from a product leader asking engineering for roadmap items.
Joe Leech: And watch for whether that’s actually happening. Are your leaders talking to their teams about the what, the why, the how, and the when? Watching for it is often as useful as asking about it directly.
Mr Joe Leech
Founder, Mr Joe
Joe is a trusted adviser and coach to CEOs of start-ups, high growth tech and Fortune / FTSE 100 companies.
A recovering neuroscientist, then a spell as an elementary school teacher, from UX research, to design, to product management then to product and business strategy.
Joe is also the author of a book on psychology, and has has a background in Neuroscience and Psychology. Joe brings 15 years in tech, $20b in revenue, experience with 30+ startups & FTSE / Fortune 100 giants.
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