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:

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