A quarterly diagnostic for founders who want to see their business clearly
Self-reflection is a big part of any coach’s journey, and one of the skills worth honing is the ability to step outside yourself and observe objectively.
A few years ago, on a coaching course, I started thinking about what that same discipline might look like for founders of scaling businesses – and about the questions I found myself discussing over and over again in my work with them.
Most of the founders I’ve worked with will be familiar with some version of the ten questions that follow. I offer them here not as a clever framework but as a reusable diagnostic: a set of prompts that reliably surface the next problem worth solving.
Taking a few minutes out to answer these honestly pays back every time.
The answers point to the next thing to work on. I’d recommend coming back to them every quarter – ideally not in a meeting, but somewhere you can think. The questions are the ones I most often use as the opening agenda for a first conversation with a new advisory client.
“Simon has a unique ability to bring the best out of the people around him. He is extremely knowledgeable, and exudes a calm and measured confidence in any situation. I have always been impressed by Simon’s ability to hold a room and bring people together, with a perfect balance of knowledge and curiosity.”
Sarah Harris, Managing Director at The Wellbeing Project
The ten questions
1. What’s the single sentence that describes your strategy – and why it’s differentiated?
If you can’t get it into one sentence, nobody else in your business has a chance. And if the sentence doesn’t contain the reason you’re different from the obvious alternatives, you’re describing what you do, not why it matters. Most founders I work with can’t answer this cleanly in the first attempt, which is usually the start of a useful conversation rather than a reassuring one.
2. What problems are you solving and for whom?
Not abstract problems. Specific ones. For specific people. The best answers to this question sound concrete – the particular pain, the particular buyer, the particular moment when they’re most open to solving it. The worst answers sound like a marketing deck.
3. How are you actively shaping the culture of the company you need to build?
Culture is the thing founders most often assume is happening by itself and most often find is going in a direction they didn’t intend. “Shaping” is the operative word – culture is the sum of the signals you send, the behaviour you tolerate, and the examples you set, not the values poster on the wall. What are you actively doing this quarter to shape it?
4. Can everyone in the business name their own goals, the company’s goals, and how they’re tracking against both?
Walk through your team and ask them. The answer is almost always more patchy than the founder expects. Clear, visible, individually-owned goals are the operating scaffolding that makes scaling businesses scale. Their absence is one of the most common structural gaps I see, and it’s almost always the thing beneath “we have an accountability problem”.
5. What are the five simple metrics you and your leadership team look at regularly?
Not 25. Not a dashboard. Five. If your business can’t name the five numbers that matter most right now, you’re running blind – and so is your leadership team. The act of choosing the five forces the clarity that most scale-ups avoid. The wrong answer isn’t “we have seven.” It’s “we don’t really track anything meaningful regularly”.
6. As a founder, are you playing on the pitch or coaching from the sidelines?
Early-stage founders have to be on the pitch. Scaling-stage founders have to learn to coach from the sideline. If you’re still playing every position six years in, you’ve become the bottleneck without realising it. If you’ve stepped back too quickly and the team is floundering, you’ve over-corrected. Where are you right now, and where should you be for the stage your business is at?
7. How systemised is your approach to selling, and how predictable are the results?
A business where sales comes from the founder’s personal relationships and ad-hoc hustle is a business with a fragile revenue engine. A business with a documented sales motion – clear positioning, a defined qualification process, a repeatable outbound rhythm, known conversion rates – is a business with something predictable to scale. Where are you on that spectrum?
8. What’s your cadence of leadership team meetings and 1-to-1s that give the business strategic and tactical rhythm?
Not whether you have meetings. Whether the meetings constitute a cadence – weekly, monthly, quarterly – each with a clear purpose, and whether the whole rhythm is running consistently or slipping because the founder’s calendar is chaotic. The cadence is the operating heartbeat of the business. If it’s irregular, so is everything downstream.
9. Are all the roles in the company clearly defined, with the right people in the right seats for this stage?
Role clarity is one of the cheapest, highest-impact interventions in a scaling business – and one of the most avoided. Unclear roles are a hidden cost every business pays but rarely measures. Plus “for this stage” is critical. A great hire at £3m might be the wrong shape at £10m.
10. Are you hiring for today or for tomorrow?
Both are valid answers in context – but the answer should be deliberate. Hiring for today too long means you end up with a team that can’t lead you into the next phase. Hiring for tomorrow too early means you’re paying for capability the business can’t yet use, and the hires disengage. The best founders I know are explicit about which one they’re doing and why.
How to use the ten questions
I’d suggest three uses.
First, the quarterly self-check in – run through them once, honestly, alone.
Second, the leadership offsite – work through them with your leadership team and see where answers diverge. That divergence is valuable data.
Third, the advisor conversation – bring them to a structured external conversation and use them to locate the next piece of work. The answers often surface the single most productive thing you could be working on in the next quarter, which is usually more valuable than a detailed strategic plan.
The point of the questions isn’t the answers. It’s the thinking the questions force.
Founders who build a habit of asking themselves a version of these regularly tend to make better decisions, see their businesses more clearly, and waste less time on problems that are symptoms of deeper gaps.
The hardest part is sitting with the uncomfortable answer long enough to act on it.
“I have a good Venn Diagram with Simon! We are both passionate about clear governance and structure in organisations and while we both help companies to achieve that often in similar ways, we each see the problem with a slightly different lens. This makes the bit in the middle, when we collaborate, very powerful. Simon is a great collaborator and teammate; working with him is a complete pleasure. He brings a diligence, pragmatism and focus rarely seen, he matches this with an open mind to change, which means we can adapt plans at pace, often required in the fast changing world of a SME.”
Jess Gregson, Founder & CEO, Extra Brain global advisory & consulting collective
Next step. Pick the question above whose answer you find hardest to give cleanly. That’s almost certainly the one worth starting with. If you want a second pair of eyes on your answers – or the honest external perspective that makes the uncomfortable answers easier to act on – that’s exactly what advisory work is for.
