Finding a Mentor or Coach
Where to find good advice when you're the boss and there's no one above you.
Notes from Randall Harper. Thirty years working alongside owner-operators, executives and boards — companies of all types and sizes — across entertainment & media, hospitality, service based business, lifestyle businesses, financial services, retail and not-for-profit, in Australia, Asia, the United Kingdom and the United States. What follows is the thinking I keep returning to.
The loneliness of being the decision-maker
Owner-operators sit in a particular kind of professional loneliness. There is no boss to escalate to, no peer at the same level inside the business, and often no one in the immediate circle who genuinely understands what it is like to carry the business in your head. A mentor or coach is not a luxury; for most owners, it is the single highest-leverage relationship available outside the business itself.
Mentor versus coach
- Mentor — someone further along the same path, sharing what they learned, usually informally and unpaid.
- Coach — a professional whose role is to ask the questions you are not asking yourself, usually paid and structured.
- Both are valuable; many owners benefit from one of each.
Where to find them
Industry associations, chambers of commerce, formal mentor programs (state-government-funded options exist in most states), peer groups like TEC or Entrepreneurs' Organization, and personal networks. The right mentor is rarely the most senior or famous one available; it is the one whose experience genuinely maps to your situation, and who has the time and inclination to engage.
What to expect, what to bring
The relationship works when you turn up prepared. Bring specific questions, current numbers, real decisions you are facing. Don't ask 'how should I grow my business' — ask 'I'm considering hiring my first employee in six months, here's the cash position, what would you stress-test in my plan?' Good mentors and coaches give better answers to better questions; specificity respects their time and produces more useful advice.
Pay for the value, not for the time
Coaches charge by the hour, and the best ones are usually expensive. The relevant question is not whether you can afford it but whether the decisions it improves are worth more than it costs. For most owners making meaningful decisions monthly, even a modest improvement in decision quality returns the coaching fee many times over within a year. The owners who can't afford it are usually the ones who most need it.
Want this as a PDF?
Tell us where to send it and we'll email you a copy to keep.
The contents of this paper are the opinion of Clear Point Advisory only. Readers should rely on their own judgement and obtain professional advice appropriate to their circumstances.