Business Strategy Coaching: The Best Questions to Ask before Hiring an Executive Coach

By Alan Gehringer

Business Strategy Coaching: The Best Questions to Ask before Hiring an Executive Coach

Take this quick quiz to determine if you are ready to engage with an executive coach and take your game to the next level.  An executive coach can help you better define your long-term and short-term strategy, align, motivate, and engage your teams and allow you to be a more effective leader.  Great leadership increases your entire return on payroll.

executive coaching

The most successful people in sports and business all take advantage of coaches to bring their skills to the next level. In many cases, these coaches are not as visionary, talented, or skilled as the people they coach, but what they bring is experience, successful patterns, an unbiased outside perspective, and a desire to help the individual grow and improve their performance and effectiveness to be the best version of themselves they can be.

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Great questions you can ask yourself to determine if you are ready for a business coach:

  • Are you highly motivated to change?
  • Do you want to improve your performance?
  • Do you want to improve your effectiveness as a leader?
  • Do you want to improve how well you drive execution?
  • Do you feel like there are behaviors that are holding you back?
  • Did you enter a new role and are not yet comfortable?
  • Do you need someone to confide in that is safe?
  • Do you need a sounding board?
  • Do you need help developing your strategy?
  • Do you need to improve the results you are achieving?
  • Do you need to reduce your stress level at work and improve your health?
  • Do you need to improve the relationships with the people you work with?
  • Are you holding the business back from reaching its full potential?
  • Do you need help getting the maximum potential from your staff?
  • Have you developed a good bench of next-level leaders for your company?
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If you answered "yes" to a few of the questions above, it may be time to act and begin your journey to greatness with a coaching engagement. Here are traits you should look for to hire a great business coach:
  • Experience growing people, businesses and doing this work with other leaders
  • The ability to hold you accountable to work on the necessary things to move you forward
  • The strength and fortitude to stand up to you and challenge when necessary
  • They practice what they preach and continually learn and receive coaching from others so that they can bring their best to you
  • They are excellent listeners while being strong communicators
  • They can ask the right questions
  • They will help you set realistic and achievable goals
  • They will help you improve your leadership skillset
  • They work with you to develop (and hold you accountable to) action plans


I recommend you carefully interview your potential coach to determine if they will help you meet your future goals. The chemistry needs to be right, and you should feel completely open and can be yourself with the coach and answer the challenging questions honestly. This does not happen overnight and requires some faith and trust on both sides. I suggest committing to at least a quarter to determine if the fit is right (unless you are meeting more frequently than monthly or bi-monthly, in which case you will know sooner).

I have had the privilege to coach many business owners the past 30 years or so while also engaging coaches to work with me to bring my “A” game to the situation. If you have not worked with a coach in past and answered "yes" to a few of the questions above, I suggest you act and begin looking for the right coach. 2021 just might be your best year to date if you do.

Good luck and please let me know your thoughts. Alan

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If you enjoyed this post on leadership coaching, here are some others you may like:

How CEOs Grow Accountable Leaders & Teams [Video]

5 Coaching Insights You'll Gain from the Best Executive Coaches

A Leader's Template: 6 Questions to Ask in Your Next One-on-One Meeting

Employee KPI Examples: How to Measure What You Want to Move

The Five C's of Team Accountability

Strategic vs. Tactical Leaders: Which Are You? [Video]

Classic BHAG Examples

4 Easy Steps to Fix Your Weekly Staff Meetings [Video]

Photo Credit: iStock Getty Images

Rhythm Systems is based in Charlotte, NC, and provides executive coaching in Charlotte, NC and across the United States with our team of experts that have worked with hundreds of clients, many backed by private equity.

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