Executive coaching is one of the most over-hyped and under-explained services in the startup ecosystem. Done well, a great coach is a multiplier on the founder's judgment and stamina. Done badly, it becomes an expensive weekly therapy session with no output.
1. The company crosses roughly 30 employees and the founder is spending more time managing than building. 2. The board has started asking whether the founder can scale into a CEO role at 100+ people. 3. The founder is making the same class of mistake repeatedly (avoiding conflict, over-hiring, under-delegating) and self-awareness alone is not fixing it.
Before those signals, a peer group or a mentor is usually a better fit. Coaching is expensive and requires more self-awareness than most first-time founders have in year one.
The coaching industry has almost no quality control. Anyone can print a business card. Filter on:
Prior operating experience. A coach who has been a CEO or C-level at a real company will give you sharper advice than a pure-play coach with no line experience.
Founder-CEO references. Ask for three founders they have coached to Series B or beyond. Actually call them.
Their own coach. Every serious executive coach has one. If they cannot name theirs, walk.
Chemistry over pedigree. You will tell this person things you have not told your co-founder. If the vibe is off in the intake call, it will not fix itself.
Most coaches charge $2K to $10K per month for two sessions of 60 to 90 minutes. Some charge annual retainers of $50K to $150K.
A stated goal. "Grow into the CEO seat by Series B" is a goal. "Get better at leadership" is not.
Access between sessions. Text or short calls for real-time decisions. Not unlimited, but not zero.
Occasional shadowing. The best coaches sit in on board meetings, exec staff meetings, or hard 1:1s a few times a year. That is where real behavior lives.
Come with an agenda. The most common failure mode is showing up empty-handed and letting the session drift into whatever is on top of mind. Great coaching clients arrive with two or three specific situations they are wrestling with and use the coach as a thinking partner on each.
Take notes. Not the coach — you. Review them before the next session.
Coaching relationships have a half-life. Most productive engagements run 12 to 24 months. After that, the marginal insight declines and the relationship risks becoming a comfortable weekly habit rather than a growth tool. It is fine — and healthy — to say "I have gotten what I needed, let's wrap up." A great coach will not resist. A bad one will try to sell you another year.
At the end of every session, you should be able to name one thing you will do differently this week that you would not have done otherwise. If that is not true for three sessions in a row, the engagement is not working. End it and try someone else, or drop coaching entirely for a while. Either is fine. Paying $8K a month for pleasant conversation is not.
