Hiring · Management

What are the questions to ask potential executive coaches?

Lucas Jaz

September 18th, 2015

We just raised an A and I'm the market for an executive coach.  It's not a "hire" I've ever made and they are not cheap. Aside from "what's your approach" i'm interested in hearing what questions I should be asking these coaches.  

John Berg Privately Held Semiconductor Company

September 18th, 2015


As a computer science grad, you are probably self-aware of have four states of knowing:

You know what you think know: hire employees to execute these tasks.
You know what you don't think you know: hire employees or consultants to figure this out and hire employees to execute it. 
You don't know what you think you know: hire an executive coach to identify these blind spots and hire subject matter consultant to solve this class of problems.            
You don't know what you don't know: hire an executive coach that pushes you to be extremely uncomfortable with your assumptions and your biases.

Average executive coaches transform the individual from a state of not knowing to a state of knowing. (Yes, average).

Although that transformation is important, it is not the most important transformation. The next level of transformation is from a state of knowing to a state of being. Knowing and being are different states. 

The client transformation from lower states of being to higher states of being is where great coaches excel. It is worth the money.

Paul Field Agile Leadership Coach - Helping you focus on business value, collaboration and innovative solutions

September 18th, 2015

All the above are good questions you could ask a potential coach. And another option you have is to let them coach you for a session (many coaches will do a free "strategy session", which will be a coaching-based meeting) - you'll get a feel for the chemistry with that coach, whether their style works for you and whether you get value from the session. So, I'd suggest shortlisting based on the questions other people have suggested and then trying out your 3 favourites. And one good test is that you ought to be a lot clearer on what you want from coaching and your vision/objectives for yourself/your company after that session.

Kelly Hadous

September 18th, 2015

As an executive coach I think a few important questions clients can ask me is:

How will you help me reach my goals?
How have you helped other people who have the same objective as I do?
What areas do you coach in? 
What have been some of your coaching success stories? 

Hope this helps! 


David Intrator Smarter Storytelling

September 19th, 2015

The story goes something like this:

A young trumpet player was working in the mid 80s as a cab driver in New York City. 

One bitterly cold winter evening he picked up none other than the great Miles Davis. 

Realizing the opportunity of a lifetime, he asked the Master:  "I want to be a great musician. What should I practice?" 

After a moment of awkward silence, Miles answered in his inimitable hoarse whisper of a voice: "Ask yourself, why do you play." 

Zohar Hirshfeld Sr. Director Business Operations, Product Globalization and Chief of Staff for Central Engineering

September 27th, 2015

My answer was going to be very similar to Christopher's answer. I would rely much more on references rather than ask the coach questions. Past successes/failures are the best answers you can find. People can give you great answers, but it might all be in theory, you want to find real examples instead.

Julie Reinganum Board Director | Mentor & Coach to CEOs & Sr Execs who want to enhance their global business knowledge & drive profits

September 18th, 2015

Hi Lucas,

Lots of good ideas above.  As to the questions to ask a potential coach, I would add:

1.  How will you hold me accountable for my commitments?
2.  How will I know I am gaining value from coaching?
3.  What makes a successful coaching relationship?


Patrick Malone Interim President & CEO at Blairsville Union County Chamber of Commerce

September 18th, 2015

Don't worry about the question you should ask. The right executive coach will ask you questions about what you want to achieve, how you want to go about that etc. You might need a couple of questions at the end but you will know what those are based the the questions the executive coach candidate has already asked you.

Joe Welfeld President; The Welfeld Group, LLC

September 18th, 2015

The role is not just as coach but mentor as well. In my past experiences, leaders need to feel that they have a advisor who they can talk to and trust implicitly.

Peter Johnston Businesses are composed of pixels, bytes & atoms. All 3 change constantly. I make that change +ve.

September 19th, 2015

Ask them one simple question - "how has digital affected the concept of leadership?".

In the 19th century you scaled a company by adding people. Companies grew into massive organisations of tens of thousands and leaders couldn't hope to know each person individually, so they applied broad concepts. 

The 20th century brought in machinery to replace human muscle. Many of the remainder were book-keepers and clerks, but in the latter part of the century these disappeared too and companies shrank to a core of knowledge workers.

But we were still living in a physical world. Making changes in physical infrastructure is expensive and systems were created to deliberately slow the decision process down and make sure it had buy-in at the highest levels. This slowed progress to a crawl and the static company became normal, with change as an exceptional event. Managing this slow change process became the core skill for executives.

These are the skills most coaches teach. How to survive in 1960s companies where facts were hard to obtain and thus opinions held sway. How to prepare reports which bludgeon change ideas through and manage all the attempts to derail this change. And how to "lead" remotely through edict.

Compare this with the digital world. Here, like a 24 hour newsfeed, things can change continually. There is a constant feed of data to work from. Small teams of experts, often geographically remote, are the way to make things happen and the timescale to do so is measured in minutes, not months. Change is default and static - even for a moment - means falling behind.

Leadership in this digital world is about enabling and co-ordinating teams to release their potential, not bullying them into doing what you have decreed is right. It is about championing them to other stakeholders to ensure they have the resources and backing they need. Keeping everyone up to speed with continuous changing of procedures, capabilities and possibilities. Sifting a deluge of knowledge to ensure what is truly relevant reaches right person at right time.

In this world, "need to know" information, management by memo and setting fixed policies - all key planks of old fashioned leadership - will hold you back. 

If your coach has experience in a large 20th century company, his/her problem will be unlearning this. They may have some nuggets to impart, but the general flow will be in the wrong direction. They can seriously damage your company.

Heather Hollick Executive, Professional, Career, and Life Coach

September 19th, 2015

Coaching is a partnership in a thought-provoking and creative process. The efficacy of this process is rarely revealed in an 'interview,' regardless of how good your questions might be.

Try before you buy. Most coaches will do one or more exploratory sessions to help both of you decide if (and how) you might be able to work together. During these sessions determine the right coach for you not by the answers to the questions you ask, but by the questions they ask you.