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Five Signs that a Coach is a Good Investment – and Five Warning Signs It’s Not

I am a coach. I have a team of coaches. We offer coaching programs to a variety of organizations. I also invest in coaching for myself and my business.

As a result, I have learned a thing or two over the past ten years. Many leaders we coach make leaps, solve what appear to be intractable problems, and develop keen personal insights that enable them to be more effective personally and professionally. The coaches I’ve engaged have helped me overcome thinking small and enabled me to see ways to handle significant challenges. I am stronger, more able, and better because I leaned into a coach at critical times.

Coaching can be a highly focused, truly individualized performance accelerator, much more effective than courses, books, or personal reflections on lived experience.

However, after having hundreds of leaders in our coaching programs, I know that coaching is not always the perfect panacea.

There are clear signals that coaching will be a transformative experience for someone and other signals that it will be a painful path to a dead end. I’ve set a goal to help my clients discern when coaching is a wise investment of someone’s time, energy, or money and when it is NOT. Today I’d like to share our criteria on when having a coach is helpful and when you should defer.

Five Success Factors

  1. Complex, fast-paced, changing environments provide fertile ground for coaching. Leading in these environments seldom provides leaders the time and space to step out of the busyness and above the hustle. Coaches provide a safe space to pause for a moment, make sense of things, and more clearly see a path forward.
  2. Self-limiting behaviors. We all have them, even leaders. Although they get in our way, we often can’t see them ourselves. Coaches are skilled in spotting the things you are doing to trip yourself up. Even better, their job is to bring your attention to it, help you see it, and find alternative approaches.
  3. Being stuck. People get stuck in lots of places. They get stuck in messy situations, dysfunctional relationships, career choices, and toxic workplaces. By its definition, being stuck is the inability to move forward. Coaches can help you find (and try) different approaches to making progress. Sometimes all you need is someone who enables you to see possible options and then a little nudge to get unstuck.
  4. Big leaps and new responsibilities. New jobs and assignments are fertile ground for growth and learning (on the plus side) and overwhelm/missteps (on the negative side). Transitions from technical expert to people leader, from manager to VP, or from VP to CEO are unfamiliar and disorienting. Having someone by your side and on your side to help you understand the role and responsibilities gives you an advantage and a fast start.
  5. Transparency, honesty (to yourself and your coach), and a desire to make a change. A person’s willingness to make changes differentiates exceptional coaching outcomes from mediocre ones. Transformative and positive change only happens when one is commit to doing something different outside of the coaching conversation. For as wonderful as that session might be, the true sign of success is what happens afterward. Great conversations do not make great coaching outcomes. Action afterward does.

Five Warning Signs

  1. Seeing coaching as punitive. This is a pitfall when the organization offers coaching only in specific situations rather than the norm. Often it is a promotion, a new role, and a challenging and important goal. When not explained as an investment in this person’s potential, leaders can feel that others see them as incapable, needing support, or failing.
  2. Not willing to open up. Despite being a safe, confidential space with another person who is not going to judge you, coaching outcomes are diminished when people are guarded, evasive, or fail to be honest with themselves or their coach. Of course, what is shared and the depth to which it is shared is totally up to the person, but skimming the surface yields superficial results.
  3. Unwilling to try new behaviors or approaches. The coaching conversation alone can be a wonderful place – a respite from demanding workplaces, a space where you are listened to and heard, and you can get things off your chest and talk through challenges. However, the compelling question is what is different in you and your behaviors AFTER the session. If you are all talk and no action, please just take a friend out for a cup of coffee and a good conversation.
  4. Being too busy to make the time for coaching. We often hear this objection when leaders are considering coaching. It also surfaces during a coaching program when sessions get increasingly difficult to schedule. The irony is that the busier you are, the more you need what coaching can offer. A place to gain perspective. A space to clear your head and chart clear direction. An opportunity to examine ways to be more effective and efficient. Being too busy is a call for coaching, not a reason to avoid it.
  5. Externalizing challenges and looking for easy answers outside of yourself. Coaching is not a place to vent and blame. It is not a place to find strategies to “fix” those other people or justify your own opinions, beliefs, and actions. Good coaches will listen and reflect back (the good and the ugly). They will challenge your thinking and approaches. They will keep you focused on personal accountability. They may allow you to wallow in self-pity for a bit, but not for long.


If you or others in your organization would be good fits and benefit from coaching, I’d love to share our proven coaching approach. You can learn more about it here or schedule a time to talk with me here.

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Evergreen Leadership