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Five Questions to Ask Yourself Before Starting Executive Coaching


Before their first coaching session with me, many clients ask me if there is anything they should do to prepare. Generally, I tell them to come with an open heart and mind (and to sign the coaching agreement I emailed them when we confirmed the engagement, please).  


You see, before we even agreed there would be a coaching relationship, I asked a number of seemingly benign questions (insert sinister laugh here) to get a sense of where the person is positioned in their leadership journey. Hopefully these questions also help the potential client unpack why they are seeking coaching, whether coaching is what they are looking for, and whether I might be a good fit for them.  


Often these calls are instigated by issues that feel urgent when the potential client starts pursuing coaches (“I’m looking for a coach. Can you talk tomorrow morning?!”). These good folks need help NOW – not next week or the week after – NOW. 


  • The last board meeting was what could only be described as an uprising.  

  • The staff meeting the day after that made the board meeting look tame. 

  • The leadership team meeting had the vibe of a high school detention room.  

  • The significant other, kids, dog – all of them – are whimpering for attention outside the door of your home office.  


Many times, the immediate pressure releases, and we don’t connect again for weeks or months, if ever.  


That moment of intense pressure can be like getting a health scare and then joining a gym you never go to or starting a strategic plan during an organizational crisis. The intention is laudable, and the activating event understandable, but the particulars of the situation may give you a sense of false urgency or undermine the long-term success of the process.  


You see, executive coaching can relieve pressure during those moments of great disruption, but ultimately it is a trusting relationship that develops over time and where the coaching client identifies where they want or need to be more effective. The coach provides tools, encouragement, direct feedback, and a LOT of probing questions to support the process.  


Coaching can help you figure out why those moments are so intense and reduce the pressure you feel through developing more effective ways to manage your time, attention, and relationships with the groups that demand that time and attention.  


Ultimately, you are in the driver’s seat in the coaching relationship. Your coach helps you stay focused on the destination while helping you navigate the speed bumps, green lights, and yield signs of your day.  


Crisis moments offer many lessons, but they can be hard to unpack without a stronger foundation of work to build on. In most coaching relationships, there is an aspect of advice giving, sparingly, during an engagement. That being said, if the relationship starts more like consulting than coaching, it can be difficult to ever bring it back on track.  


When you can find a few minutes to clear your head, there are questions you can ask yourself to make sure you are ready to start coaching, not just purchase a sympathetic ear for an hour or two.  


These questions can also help build your motivation to make the commitment to the coaching process. If you’re not sure how to answer one or two of these, they may be great questions to raise with prospective coaches.  


What outcome am I hoping to achieve? 


If your motivation for beginning coaching starts with, “I just need someone who understands my role to talk to,” I suggest building your network of nonprofit colleagues. A monthly breakfast, lunch, or coffee with trusted colleagues (which you should be doing anyway) is cheaper than coaching.  


If instead, you want to create lasting change in your leadership, before you call prospective coaches, imagine what success might look like for you. What would make you look back in six months or a year of starting coaching and feel that you had improved your practice (that it was worth the expense)?  


Reflect on what areas of your performance continue to nag at you. Are you buried in work that could be done by someone with less experience? Do you feel like your job is an unending game of whack a mole? Does your anxiety prevent you from making clearheaded decisions (or any decision at all)?  


Having some sense of this is probably the surest way to find the right coach for you – the person who will support you in making that vision a reality.  


If the vision of success is somewhat patchy, raise that with your prospective coach. Find out how they help others hone that vision.  


Am I willing to be uncomfortable?  


Accepting that the way you work has led to success until now but may not in the future is what I reference when I recommend an open mind and heart to my clients. Growth through coaching begins with looking at the current moment as a challenge that will require new leadership and managerial strategies and a new definition of success.  


And it requires listening to those you work with closely – whether through a 360 process or some other assessment. There is always feedback that nags you throughout your career. Showing up bravely to make headway in addressing that feedback can deepen our satisfaction in leadership and set a tone that personal growth is something you value. When I perform 360 interviews, so many interviewees mention how heartening it is to know that their leader values personal growth enough to take part in the process.  


Will I give this process the time and energy it takes for it to work?  


Coaching and the learning that can come from it is a change process – it will take time to see results. Just like a stunning new physique, a hand-crocheted patchwork blanket, or a blog post about questions to ask yourself before starting executive coaching, nothing happens without your showing up and putting in the work. 


I know you’re busy, but I don’t want you to look back on your executive coaching with buyer’s remorse. Make sure to make time for this process.  


Am I ready to take action and hold myself accountable? 


The gains we hope to achieve through coaching require us to try new behaviors, reflect, refine, and try again. My coaching clients and I end each session by collecting reflections and then deciding on action steps they will take before our next session – exercises to do, articles to read, new techniques to try out. And they can each trust that there will be a friendly (and I’m guessing sometimes annoying) reminder from me on those goals between sessions.  


Does industry knowledge matter?  


This is a hard question for many prospective coaching clients and a good discussion to have with any potential coach. Industry knowledge can help you feel like you are fast-tracking the coaching process by avoiding explanations of your day-to-day (galas, funder meetings, nonprofit resources constraints). At the same time, it is easy to get lost venting about that day-to-day with someone who understands. Once you identify the issues you are hoping to address through coaching, you may determine that someone “who won’t’ go there with you” is the stronger choice. Or you may want a coach with a very specific niche – public speaking, board management, communicating vision, or managing a leadership team.  


Ultimately, your coach’s job is to help you maintain your focus, whether your job encourages or discourages that focus.  




Your coach will be your guide on a journey of self-discovery, a partner in strategy, emotional support, and an accountability buddy. Finding the person who can fit the bill (fit all those bills) for you is a first critical step in your development.

 

Spending time focusing on these five questions can help you ensure the coaches you meet (and you should meet three during your discovery process) are ready to play these roles effectively in your partnership.  


If you want to learn more about my approach to executive coaching or any other aspect of my work, you can follow me on LinkedIn, Facebook, or schedule a discovery call HERE.

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