Coaching executives and other leaders has some different aspects to it than coaching middle managers, let alone individual contributors.

Context: company growth ahead of experience growth

These notes are in the Midstage Manual because most midstage companies have grown rapidly from an early stage-startup just a few years ago.

As a result, founders who “yesterday” were managing only themselves, are now expected to coach executives. Most often these are people who are vastly more experienced than the founder(s), and sometimes of a different generation too.

These notes are intended to help both founders and (new) executives navigate this particular situation.

Founder challenges: learning to scale through people

Founders hire experienced executives because they would like to delegate big parts of the business to somebody experienced.

This means that challenges in coaching executives are:

  1. Setting (and verifying understanding of) clear outcome expectations
  2. Letting go of doing things yourself
  3. Instituting regular follow-up
  4. Giving people room to do things their way, even if you would have done them differently
  5. Giving people objective yardsticks to measure their own performance

Setting clear outcome expectations

If you want an experienced executive to perform well, it is best to start from clear (and written) expectations.

These give both parties an objective standard by which to evaluate performance, and they empower the executive to apply all their experience and creativity in reaching the goal.

Clear expectations should be aligned to KPI and OKR standards:

  • an inspiring outcome
  • clear metrics and deadlines (bring metric x from y to z by dd)
  • the fewer the better. five KPIs and OKRs (combined) is common for executives.

Letting go of doing things yourself

Good executives insist on proper delegation. They will “scream at their coach” if the coach tries to get involved in how they are reaching their target.

As a coach of an executive, remember that the executive is the athlete on the field. You are the coach off the field. Your job is not to play the game yourself. It is to make the executive win.

Instituting regular follow-up

Giving people room to do things their way

Giving people objective yardsticks

About Midstage Institute

We focus our practice on midstage startup companies that need to remain agile, and where what used to work for the smaller startup just isn’t as effective anymore.


We ensure founders and leadership teams win, with our over 40 years experience in venture-backed tech startups. We are Silicon Valley veterans with the scars and wins to prove it. We don’t use an inflexible off-the shelf methodology, we adapt best practices to you, your market, your company, and your leadership team.


We always:

  • Focus on right sized best practices to get to the next level
  • Focus on the 20% of effort that will yield you 80% of the benefits
  • Teach Perfection is the enemy, better is your partner and ally
  • Align with your business needs so you can thrive