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Put Me In, Coach!

Recently, I attended a week-long yoga / meditation / group therapy retreat. No, we didn’t wear red,* but we did spend a lot of time discussing our fears, what holds us back in life, and what our ideal state of being in this world is. When someone stood up to discuss his life situation in front of the rest of the group, the retreat leader / guru / multi-millionaire / yogi-to-the-stars would always ask the following questions:

  • What do you fear about this situation?

  • What is preventing you from taking action?

  • What’s your ideal outcome in this situation?

Encouraging someone to thoughtfully answer these questions was incredibly powerful: The individual gained clarity and objectivity about the situation at hand AND devised his own path forward to approach the situation. The retreat leader / guru / multi-millionaire / yogi-to-the-stars guided the individual to come to his own conclusions.

After the haze of the week subsided and I returned to civilian life, I realized that the approach we were using was almost identical to how we coach our teams and employees. As I’m sure many of you have experienced, the term “coaching” is thrown around quite a bit: Companies claim to want “player-coaches” to fill their management ranks; executive coaches are hired as a panacea for upskilling leaders; and Oprah swears that her life coach has transformed her in magical ways**. But, what often isn’t discussed is what exactly a coach does - how they work their magic - and, more importantly, how any manager can utilize the tool of coaching as a way to support and develop his / her team.

Coaching is a technique used to help guide someone towards greater self-awareness, clarity on decisions and choices, and reflection of past behaviors. Unlike a mentoring or feedback conversation, a coaching conversation doesn’t involve the coach immediately telling the coachee what to do or what he would do if in the same boat; rather, the coach guides the coachee through a set of questions and prompts, helping the coachee explore different outcomes and build the decision-making muscle.

In short - I love coaching. It’s a powerful tool to have in your toolbox as a manager. And, I think all managers - regardless of level or seniority - can build this coaching capability. Being a great manager involves coaching your team members. A great manager coaches her team members as a way to help them build more self-awareness and confidence, and build the muscle of decision-making.

Before we get to the how of being a great coach, let’s briefly talk about why coaching is so powerful.

1. First, the best employees are those who are proactive, come to you with ideas and solutions, and those that have opinions on decisions. But, this is a capability that needs to be built. Coaching helps to build that capability in your employees by training them to evaluate decisions, be reflective, and develop their own opinions about things (versus always looking to you, the manager, for “the answer”).

2. Second, coaching empowers the employee to develop his / her own course of action to address a situation or a challenge. When an individual has input or is the primary decision-maker for a decision, they are far more likely to take ownership over that decision, be committed to executing on that course of action, and be supportive. In essence, folks are more likely to do something when they make the decision themselves to do it! (remember, we talked about this in the context of goal-setting!)

3. Lastly, as a coach, you ask a set of questions to uncover assumptions, biases, and discover alternative options or paths. Asking thoughtful questions with the person you are managing (and actively listening to the answers) adds a new, deeper dimension to the boss - employee relationship. When you are being truly listened to you are able to show vulnerability, you are able to be more open, and in turn, you build trust with the person who is doing the active listening. When you coach, you are giving your managees the chance to open up in a safe and vulnerable way - thus, building greater trust in the relationship. (Remember, vulnerability -> trust -> lots and lots of good things.)

Okay - you’re convinced why coaching is powerful. Next step is how you can start coaching! Most important thing is to start asking thoughtful questions. Next time you are about to suggest a solution, perhaps ask a clarifying or probing question first that allows your employee to reflect or consider other options. Here are some other tips on your way to becoming a great coach!

How to Be a Great Coach

  • Ask open questions that require more than a “yes” or “no” response

  • Ask questions one at a time; early on, we have a tendency to pile on questions, especially as we look to get context and information.

  • Approach the conversations with true curiosity, as opposed to fishing for an answer. (Example is: Why didn’t you do this? (fishing) vs. What prompted you to choose that path? (curiosity).

  • Embrace the silence (even when it’s awkward!) Let silence linger - don’t try to fill the silence with comments; give your coachee the space to think and process.

  • Repeat back what you’ve heard to show that you’re listening and importantly, test that you’re understanding the conversation accurately. Often when something is played back to us, it allows us to reflect on what we said from a different perspective.

And, wanna know a little secret? When you first start practicing your coaching skills, start by asking the few simple questions from the beginning of this post. Ask “What concerns you about this situation?” Ask “What do you fear about having the discussion?” Ask “What’s your ideal outcome?” And, ask “What would be an alternative way to approach this?” You’ll be amazed at what happens when you ask these simple questions!

Want more powerful questions? Check out this incredible list of coaching questions. Hint - I like to have a printed copy of this doc on my desk!


  • Coaching is a technique that allows a coachee to build the muscle around decision-making and evaluate behaviors and options.

  • You don’t need to be a professional coach to deploy this technique with your team members - anyone can be a coach and it’s a great tool to help your employees develop.

  • Part of why coaching is so powerful is because it empowers individuals to come to their own conclusions; it also helps individuals build the capability of being proactive and solution-oriented.

  • To start coaching, just start asking questions! Thoughtful questions coupled with active listening are all you need to start your journey to be a great coach.

*Friends and family have kindly pointed out that this yoga retreat slightly resembled the structure and commitment recently seen in Wild Wild Country. I wholeheartedly disagree with this comparison, especially because the Rajneeshee were not expected to pay vast sums of their own money to take part in the community.

**To be fair, Oprah’s life coach, Martha Beck, seems like an incredible bad a$$.


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