Not all business coaching is equal. Neither is your stage of growth. You have survived the startup. Now you are scaling. The coach or mentor you choose could save you years of expensive mistakes — or add to them.
Anyone can call themselves a business coach. Here are eleven tips to help you to choose well.
Running an adolescent business is a specific challenge. You are beyond the adrenaline of the startup, but a long way short of the systems, structure and scale of a mature organisation. The entrepreneurial energy that got you here is no longer enough on its own.
At this stage, a good coach or mentor can make a material difference. So too can lots of other people in a variety of relationships. Whatever the role, a poor choice can waste your time, blur your thinking and cost you money. The problem is that the market is crowded. Anyone can call themselves a business coach, an adviser, a mentor or whatever they choose.
So how do you choose well? Here are eleven things worth considering.
1. Understand what you are actually buying
Coach, mentor, advisor, consultant, non-executive: these words get used interchangeably, but they describe different relationships.
- A coach asks great questions to help you reach your own conclusions.
- A mentor has been where you are and shares experience.
- An advisor brings specialist knowledge in a particular field.
- A consultant manages a process to move you from A to B.
- A non-executive director (NED or NXD) is a board director with fiduciary duties.
See this article for an explanation of the differences between them in more detail.
So before you talk to anyone, be clear about what you actually need. Role clarity matters more than job title. A coach mentor — someone who combines the questioning discipline of a coach with the lived experience of a mentor — is often the most useful combination for a scaling CEO. So read on for some specific thoughts on the specific role of coach mentor.
2. Check that they have actually run a business
This matters more than any qualification. Plenty of coaches are trained in questioning technique without ever having held P&L responsibility, dealt with a cash crisis, managed a difficult redundancy, or navigated a growth plateau.
When a mentor has been there themselves, the conversation is different. They understand the specific loneliness of the top job. They know the difference between the theory of delegation and the reality of letting go when the business depends on the outcome. Look for evidence of real operational leadership, not just proximity to it.
3. Look for experience of your stage of growth, not just your sector
Sector experience is useful but often overrated. What matters far more is whether your coach understands the specific dynamics of an adolescent, scaling business. The challenges you face — building a management layer, delegating without losing control, maintaining culture through growth, managing cash whilst investing — are almost universal at your stage.
Someone who has led six businesses of different sizes, across different sectors, and has sat in hundreds of rooms with scaling CEOs talking candidly about their real challenges, will likely serve you better than a sector specialist who has only seen one part of the picture.
4. Expect to be challenged, not just supported
Honest feedback is scarce at the top. Most people around you have an interest in keeping you comfortable. A good coach or mentor will say the difficult thing when it needs to be said — clearly, calmly and without ego.
Pay attention to how a prospective coach responds when you present a confident view in an early conversation. Do they probe how you arrived at it, or do they accept it at face value? One description of a good coach mentor style is “gentle but persistent — directly questioning whilst sowing seeds for my consideration.” That balance is worth looking for.
If your first few conversations feel entirely reassuring, consider whether you are talking to the right person.
5. Watch how well they listen before they speak
The quality of a coaching conversation depends more on listening than on talking. In a first conversation with a prospective coach, notice how much they ask versus how much they tell. Do their questions build on what you have said, or do they default to generic frameworks that could apply to almost anyone?
The best coaches slow your thinking down. A session that leaves you with two or three things to genuinely reconsider is more valuable than one full of advice you already half-knew. If they rush to solutions before they understand your situation, take note.
6. Beware the single formula
Some coaches and mentors become very confident in their own formula for success. If it worked once — or even several times — they can apply it regardless of context. This is one of the more common traps in business mentoring.
No two businesses are the same. No two CEOs are the same. You need someone whose experience is broad enough to explore and address the differences between situations, not someone who starts every engagement with the same answer. If a coach is too certain too quickly, that is a warning sign.
7. Look for practical thinking, not theoretical models
As a scaling CEO, you need tools that work in your business on Monday morning. You need thoughts, tips and approaches you can apply quickly, test, and adjust. You do not need complex academic frameworks, lengthy strategy documents, or dense methodology.
A good coach for your stage of business keeps it simple. They help you cut through complexity, not add to it. Ask prospective coaches for concrete examples of how they have helped someone in a situation similar to yours. Listen for specifics, not slogans.
8. Assess whether you can trust them with the real stuff
The conversations that matter most in coaching are the ones you cannot have anywhere else. Strategic uncertainty you cannot share with your board. Interpersonal tensions you cannot discuss with your team. Decisions where you are not yet sure of the right answer.
Trust is not built in a first meeting, but you can sense integrity early. Is this person discreet? Do they focus on your development rather than their own opinions or visibility? Are they consistent? If you do not feel safe enough to speak freely, the relationship will stay shallow, and so will the value.
9. Distinguish between advice and dependency
A good coach mentor helps you develop your own thinking. The goal is not that you keep coming back for answers — it is that you become a better decision-maker yourself. One long-standing client described working with their coach this way: “He allows me to develop my own ideas, even though when I look back, a lot of my conclusions are utilising his deep experience of business.”
That is the right outcome. Be cautious of any coach who positions themselves as indispensable or who gives advice freely without helping you understand the reasoning behind it.
10. Check their track record with evidence, not marketing
Any coach can describe themselves in compelling terms. What you want is evidence of outcomes. Ask to speak with people they have worked with. Read testimonials carefully — are they from leaders at your level, in your type of business? Do they describe specific results, or generic satisfaction?
LinkedIn recommendations accumulated over decades of leadership across multiple businesses, boards and sectors give you a more reliable picture than a polished website. Experience that shows up in how someone thinks and engages is worth more than credentials they list.
11. Make sure the fit is right, not just the quality
Even a highly credible coach with all the right experience will not be effective if the fit is wrong. The right coach for you aligns with your goals, your context, your values and the specific challenges you face right now. That fit matters as much as their CV.
Use an initial conversation as a genuine test. Notice how you feel afterwards. Do you think more clearly? Have you reconsidered something you were certain about? Did the conversation leave you with something useful to act on? If yes, that is a good sign. If you felt mostly validated and comfortable, keep looking.
Five red flags worth knowing
Before you commit, watch out for these:
- They offer solutions before they understand your situation.
- Everything they say sounds generic — applicable to any leader, in any business.
- They avoid difficult conversations and stick to reassurance.
- Their approach is rigid — the same model regardless of your context.
- They over-promise outcomes or speak in guarantees.
One final thought
Leadership is a learning journey. None of us is the finished article. The best leaders I have met and worked with over 40 years kept looking for ways to improve, even when they were already succeeding. Many of the most capable ones sought out support early rather than waiting until they were in difficulty.
The right coach mentor will not tell you what to do. They will ask the questions that help you see your situation more clearly, challenge you when your thinking needs it, and share experience from situations similar to yours when it is genuinely useful. The result, done well, is that you become a more decisive, more effective leader — with less stress.
Use these eleven tips as a practical filter when you evaluate your options. Take your time. Ask the right questions. And do not mistake confidence or polish for depth.