Key takeaways
- Coaching for owners is about decisions, habits and conversations in the business, measured by what changes in the company.
- A good quarter of coaching has a short list of named changes, a fortnightly session and homework that happens in the real business.
- The coach should have run companies and should be willing to tell you when you are wrong.
- If nothing in the operating numbers or the org chart has moved after a quarter, the coaching is not working.
Many owners avoid leadership coaching because they imagine an hour of talking about feelings with someone who has never met a payroll. That version exists and it is not what we do. Coaching for an owner is about the decisions you keep avoiding, the conversations you keep postponing, the habits that keep you in the weeds and the way you run the people who run the company. It is measured by what changes in the business.
Ali coaches owners across British Columbia alongside the fractional and operating work our team does, and this guide sets out what that looks like so you can judge whether it is for you.
What it works on
Each of these shows up in the operating numbers, the org chart and the team's behaviour, which is how progress is seen. Coaching that cannot point to a changed decision, a held conversation or a number that moved is conversation.
- Decisions you have been circling for months. The underperformer you have not addressed, the price increase you have not made, the partner conversation you keep deferring.
- The habits that keep you in the work. Answering every message, attending every meeting, approving every spend, and the reasons you give yourself for doing so.
- Running your leadership team. How you run the weekly meeting, how you give feedback, how you set and hold standards, how you delegate.
- Your own calendar and energy. What you spend time on, what you avoid, and what the company needs from you in the next year that you are not yet doing.
How a quarter is structured
The quarter starts with a short list of named changes, usually three. For example, hold the performance conversation with the operations lead by the end of month one. Hand the weekly meeting chair to the COO by month two. Stop approving spend under a set amount by month three. Each one is specific enough that both of you will know whether it happened.
Sessions are every two weeks, an hour, by video or in person in Vancouver. Between sessions the homework is real. Have the conversation, change the process, run the meeting differently, and report what happened. The coach's job in the session is to prepare you for the next one, to challenge the story you tell yourself about why it is hard, and to hold you to the list.
What the coach must bring
An owner's coach should have run companies, hired and let people go, made payroll in a hard month and sat across from a buyer or a lender. Ali has founded eight companies since 2007 and leads every engagement personally, which is the standard we hold ourselves to. The coach should also be willing to tell you that you are wrong, that the problem is you, and that the thing you are avoiding is the thing to do this week.
Where a coaching conversation touches employment law, tax or a shareholder dispute, the coach's job is to help you decide and then send you to the employment lawyer, the CPA or the corporate lawyer with the question framed. We work alongside licensed professionals and never stand in for them.
Where coaching ends and support begins
Sometimes what an owner needs is not coaching. Burnout, anxiety, a marriage under strain from the business, grief, or a health problem are real and common among owners, and they need qualified support from a counsellor or a physician, not a business coach. A good coach recognises the difference quickly, says so plainly and helps you find the right person. We hold that line carefully.
How to judge it
At the end of a quarter, look at three things. Did the named changes happen. Has anything moved on the weekly page or the org chart as a result. And are you spending your week differently than you were. If the answer to all three is no, stop the coaching, regardless of how good the sessions felt.
The common mistakes are choosing a coach for their manner rather than their record, treating sessions as a place to vent rather than to decide, and keeping the list vague so that nothing can be judged. Coaching sits inside our advisory retainer band of $8K to $25K per month when combined with operating support, or on its own for owners who want only the fortnightly sessions.