How to Pick the Right Executive Coach


Executives make or break companies. The right coaching, in turn, helps to make executives.

So, choosing the right executive coach matters. But it’s not easy. There are many coaching styles and different approaches that work toward different outcomes. Not every approach will work for every executive in every situation.

The trick is to find the best one for your context.

Here are the questions to ask when selecting an executive coach.

Is the coaching approach structured or organic?

A highly structured approach focuses on accomplishing specified objectives. It’s a hardline choice that can get results, but it limits possible outcomes and growth. Sticking too rigidly to structure can kill the chances of discovery happening along the way.

A purely organic approach, on the other hand, sets no objectives (or it only sets vague, feel-good objectives like “growth” or “improvement”). Engagements are conducted with a huge amount of room for conversation and changing context. Consequently, there’s often a lot of discovery that seems helpful, but few concrete results to point to.

We find the best approach to be the middle ground. Goals are essential. So is the ability to adapt to changing contexts.

That’s why we start executive coaching engagements with an upfront, 360 degree assessment, accumulating insight and data from a broad range of stakeholders. Doing so allows us to identify strengths and performance gaps, and it serves as a structured foundation for goals and strategy. But it doesn’t confine us. We also leave room for organic input, in two ways:

  • Contextual conversations. We incorporate current situations (an upcoming board meeting, a major project, etc.) into discussion, often as entry points into deeper issues.

  • Continual feedback. We hold ongoing alignment meetings with direct managers or sponsors to ensure progress is being made in the right directions. Feedback is relayed back to the learner.

Is the coaching style militaristic or encouraging?

There’s a place for the drill sergeant – the direct communicator whose only job is to elicit the right behaviors. On this far end of the spectrum, encouragement and support don’t exist. The coach provides a prescription for how to act and lets the executive know where they fall short.

Some executives prefer these kinds of straight-shooters.

On the other side of the coin, there’s also a place for the coaches who specialize in support and encouragement. Working with these people is like a dose of Chicken Soup for the Soul. They’ll make executives feel good. But they might not get them to change.  

Most coaches fall somewhere in between the two extremes but do lean toward one or the other. There’s value to both approaches. For our part, we offer direct feedback, but we also seek to build rapport so that support can be given with it. 

A quick tip: to get a feel for a prospective coach’s style, schedule time upfront. Plan to meet the coach, develop rapport, and confirm personality fit before committing to the engagement.

Does the coach have experience in similar engagements?

Finally, choosing a coach with relevant experience can go a long way toward ensuring a successful engagement. Experience can take a few forms: 

  • Experience in desired objectives. This is important. If a coach has never worked with an executive to implement a cultural turnaround, they’re probably not the best selection in a turnaround context. If they’ve never helped a new executive assimilate, they’re likely not the best choice for a new executive. A coach’s past experience should align with current goals.

  • Experience coaching similar roles. This is also important. If a coach hasn’t worked with a certain role (say a VP, or a CEO, or a CFO), they may not be the best selection to work with an individual in that position.

  • Experience coaching in an industry. Industry experience is helpful, but it’s nowhere near as important as the preceding experience qualifiers. The characteristics of leadership are consistent across industries. People are people.

Choose a Proven Approach

If you want to set up a successful executive coaching engagement, these three questions are a great place to start. Weigh them in the context of your organization, and don’t hesitate to ask for clarification from prospective coaches as you consider service.

 The best approaches, though, succeed more often than others. We’ve spent years honing ours in contexts across Fortune 100 companies and industry-shifting startups – and we have a success rate of virtually 100%.

 It’s due to a data-driven approach that walks the line between organic and structured, balances directness with support, and is proven in VP through C-Suite engagements.

 Choosing the right executive coach matters.

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