In Coaching Tool-Kit

As an executive coach for senior executives, during my first meeting with potential clients, I find it’s important to help them assess the best coach for their unique challenges. When evaluating fit, many people make the mistake of choosing someone that they feel most comfortable with. While chemistry and ease of connection is absolutely necessary, it is not a sufficient factor in selecting a coach. You want to get sustained results in your coaching process. Below is a list of questions that will help you assess fit.

Have you coached people in my context? Credibility is one of the most important factors in selecting a coach at the senior levels.  I recommend you make a list of what’s important to you in a coach based on your context and ask for specific examples. For example have they successfully coached leaders at your level, in companies and roles where leaders are faced with change and complexity? Have they worked with leaders who have a mix of different stakeholders including a board of directors or an external ecosystem? Do they have global experience? Do they have experience managing the pressures of a P&L and the politics of influencing at the very top of organizations? In addition to context, you may want to make sure that the coach is certified through a body such as the International Coaches Federation (ICF) so they have skill sets in coaching you rather than just giving you their perspective on how to handle a situation. The latter is essential because it’s the difference between having a coach and having a mentor. Coaches help you create sustained growth within yourself as a leader.

What’s your coaching experience and success rate with leaders who have goals like mine? I recommend you share your coaching goals and ask them about their experience in coaching someone with similar goals. A good way to clarify your coaching goals is to think about what success looks like to you in 12 months. What would have happened for you to feel good about your results and progress? You may also want to check in with your boss and other stakeholders to get input on these goals. You want to listen for confidence but also humility, because no coach can guarantee results. Results depend significantly on your commitment as the leader and the coach partnering with you on influencing the ecosystem.

How do you work with stakeholders? If a coaching process is to be successful, a coach will want to engage with the stakeholder system the leader is part of. This includes getting 360-degree feedback, engaging with your boss to ensure that they are supportive of the process, connecting with HR etc. You want to know what you can expect and also what will be optimal from the coach’s perspective to help you achieve your coaching goals.

How do you handle confidentiality? Trust between the leader being coached and the coach is the foundation of a good coaching process. Confidentiality is part of the code of ethics of the profession, but be sure to ask the coach how confidentiality will be handled. This is especially important as coaches at the senior level will want to interact with your stakeholders in the coaching process. You want to make sure that they discuss with you what they plan to share and get your consent before sharing anything specific.

How do you define and measure success in a coaching engagement? In my view, success should be measured in terms of skills (e.g. influencing others) and behavior change (e.g. better listening) and the impact of that (e.g. demonstrated by getting buy-in to Initiative X). Success should be assessed not just by the individual being coached but by key stakeholders they want to impact. And success should be measured all along the coaching process rather than just at the end.

What kinds of clients have you had most success with? You want to understand what the coach’s sweet spot is. Many coaches focus on transition coaching (helping people be successful in a new assignment). Others focus at certain levels or skill sets.

What is your typical coaching process? This is the nuts and bolts of what you can expect. How much time commitment will this take? Do they recommend certain leadership assessments or 360-degree feedback? How often would you meet or talk? How long does the coaching process last? What happens when its not working? A good coach will customize their process to your coaching goals and will educate you in their experience of what works and what doesn’t.

What happens in a typical coaching session? You want to know what to expect. In most good coaching processes, the coach will want you to drive the agenda of each coaching session, keeping the overall goals of the coaching in mind. They will ask you about what you committed to doing and what you learned from that. They will want to know your successes and challenges and what you’d like to focus on in this session. At the end of a session, they will ask you to step back and share what you learned and what actions you’re committing to.

What kinds of issues can I bring to the table? There is a great Buddhist saying “Wherever you go, there you are”. In my coaching experience, many of the challenges that leaders face at work, they also confront in their personal lives. You may want to talk with your coach whether they welcome your bringing personal issues to the table if this is important to you.

How do you address lack of motivation or resistance to change? Often in a coaching process, if the process is working, you will experience your own resistance to change. Creating sustained changes in behaviors and attitudes is hard, and it’s normal for resistance to come up. A skilled coach will be able to discuss with you how resistance shows up, how they will work with you to address it. This will help you build trust. It will be important to discuss how you want to be held accountable to the actions you’ve committed to.

What would you like to know about me? This is a great question because the coach’s questions give you a sense of their style, their priorities, their values. A good coach will have a clear list of questions that they may ask you to determine whether you’re a good fit for them. They may want to know how coachable you are, and how realistic your goals are.

What else would you like me to know about you? This gives the coach an opportunity to share more about themselves that you may not have asked.

Most important final step. Do a gut-check. What was the felt-experience of spending time with this coach? Were you able to let your guard down and establish trust? Were they insightful in their questions? How did they listen? What did they notice about you? Did you come away with any AHA’s about yourself? Every conversation with a great coach (even a preliminary one) is great if it leaves you feeling more in touch with yourself, empowered, and expanded in some way! You should expect no less from your coach.

My mission is to help you grow into your potential to be transformational leader who is effective in leading in disruption. I hope these sets of questions are useful to you as you select the coach who will best help you meet your coaching goals.

If you are part of an organization that hires executive coaches, reach out to me for the “Tool-Kit for Executive Coaching Impact“. It helps HR leaders optimize the impact of their executive coaching program.


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