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Confessions of an Aspiring Coach

by Cheryl Jekiel
August 22, 2018

Confessions of an Aspiring Coach

by Cheryl Jekiel
August 22, 2018 | Comments (8)

After teaching teams about coaching skills for many years, it still surprises me how challenging it is to build better coaching habits.The other day, I was in a conversation with someone in the lean community whom I deeply respect. He remarked to me, that asking effective questions is still the hardest thing for him to do, which really surprised me.

We both agreed that our knee jerk response to give people the answers is really hard to overcome.


We’d have to stop being the problem solvers for those around us.

We’ve become used to seeing our roles as leaders as the ones who fix things for people.  Even harder, it can be difficult to draw the line between removing barriers for our teams and solving issues they need to solve for themselves.

Yet, it’s critical we figure out a way.  Coaching is the role of a leader in today’s organization.

We also both agreed that if we find it that difficult, consider the challenge for the hundreds of managers within our organizations! While the need for better coaching is clear, especially in a lean enterprise, we have yet to truly face what building these habits may require.

What's changed for me over the last several years is realizing that leadership skills require building new habits, which is a slow and painstaking process. In addition, I find that most of us have little experience creating goals around creating habits. We’re used to creating SMART goals around things that pertain to specific work initiatives or key metrics.

Years ago, I was part of a leadership development class that became close with each other as part of our learning process.  After we finished the formal class, we were encouraged to stay connected by email as a way to share our difficult conversations, including the victories and defeats. This experience helped me realize how important it was to find a place to be vulnerable with others about the challenges of leadership.

Since then, I’ve always tried to create a work environment that allows managers to look to each other for support and ideas for how to redirect their patterns of behavior. After all, the greatest way to accomplish any goal is to get enough help to achieve it.

Fundamentally, my leadership development experiences have included three ways to work on goals that support creating new habits: 1) curriculum for information; 2) community support for guidance and encouragement; and 3) reminders to keep new behaviors top of mind. Following are some examples of the kinds of actions that help build habits.

  1. Read or listen to one (or all) of the following books:
    • The Coaching Habit by Michael Bungay Stanier
    • Humble Inquiry by Edgar Schein
    • Helping by Edgar Schein
  2. Community support. Some ways to develop community support are:
    • Find a mentor to regularly discuss your progress
    • Ask your team for support in building the coaching habit
    • Reach out to a peer and discussion your progress
  3. Reminders to keep the habit building top of mind. Try using one or more of the following to remind you to develop your coaching habit:
    • Put a reminder on your daily work journal to listen and ask open ended questions
    • Put great open ended questions to ask on a laminated card in your planner
    • Put reminders in your calendar to ensure you refrain from telling your people what to do

What are your struggles with developing a coaching habit? Comment below and share.

The views expressed in this post do not necessarily represent the views or policies of The Lean Enterprise Institute.
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Mark Reich August 22, 2018
1 Person AGREES with this comment

Hi Cheryl,

Great Post. I was fortunate enough to have many good mentors that wouldn’t just hand me the answer. But to this day, I find it an ongoing challenge not to go there. Your hints and guidance are quite helpful.

I also feel there are learned behaviors on how to be a good “coachee”. Something we don’t emphasize this enough. Early in my career in Toyota, I CRAVED for the answer and sometimes was vocal when I didn’t get it.  For the coachee, this “not giving the answer” can be frustrating.  It requires a huge amount of trust. And a desire for learning.  This is also a critical mentoring point of the coach. 


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Cheryl M Jekiel August 22, 2018


Speaking of CRAVING the answer...I've found it interesing  leaders are often concerned with how people feel about not being given the answer.  

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Mike Orzen August 22, 2018
1 Person AGREES with this comment

Wonderful post! To make new habits requires that we break old ones. Habits define who we are and how we react (especially when the pressure is on). Most leaders and managers specialize in the habit of “telling” and not asking.

It’s no wonder managers find it so difficult to change. Applying lean thinking one might ask, “what systems do we have in place to foster effective coaching behaviors?” I often find the response is, “we read books on coaching, have a coaching workshop, and assign a mentor.” While these steps are well intended and necessary, they are often lacking in creating enterprise-level change in how people coach and lead others. The result is often a few managers who effectively coach and many managers who struggle and often do more damage than help.

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Tracy ORourke August 22, 2018

Great article and advice Cheryl, I wholeheartedly agree. It seems that more organizations are recognizing that their leaders need help on being a better coach. If one of the primary roles of a leader is to build the employee's problem-solving muscles, then a whole new set of skills is required and building better skills including the Socratic method, becomes a priority. 

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Carl Watt August 22, 2018

Really appreciated the reading list.

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Ken Eakin August 23, 2018

great post. i agree that most of the time we should, as you say, listen and ask open questions— aka coach them. That is hard to do and we must constantly work on getting better at it.

That said, i feel there can be times where it is appropriate to suggest or tell.  When someone you are coaching is at a total loss for what to do and is asking for your advice, it is entirely reasonable to say, “why don’t you try ____ ?” (E.g. “... to go observe area X to see if you can spot areas for improvement?” when you know there are obvious problems in area X). And then, if they agree to try it, you agree with coachee when you can follow up and ask them how it went.  Their reflection and learning after the fact is what’s crucial in these cases, and can make up for your having robbed them of the opportunity to think initially.

while it might be ideal in theory to set the terms up front with coachee, having them agree that you’ll never tell or suggest, in reality coaches IMO do best when they are able to build trusting relationships by constantly dancing between what the client needs and what the client wants.  And they certainly don’t want to have to think deeply and differently all the time! Until there is deep trust, it’s hard (and unadvisable) to force them to do so, regardless of what they previously agreed to.

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Katie Anderson August 23, 2018

Cheryl - great post! As you know, "getting out of the habit of telling" has been a personal challenge for me too, as I shared in my Lean Talk at the LEI Summit in March and have written about in the Lean Post. I'm challenged each and every day to follow through on my intention to ask more questions.

The books you recommend are tops on my list too and I highly recommend them to anyone wanting to be a better leader, parent or person generally!

One process that I have found helpful personally, as well as for those whom I coach, to get feedback on the quality of questions asked is to have someone write down verbatium what comes out of your mouth. There is nothing like immediate, concrete evidence to help shape the development of new habits. 

Another process that can be helpful too is to use A3 thinking (such as the Personal Improvement A3 process) to more deeply understand one's current condition (eg. current habit of telling vs asking) and develop an action plan for practice. Bringing greater intention to one's practice and breaking it into steps can be useful in getting better. 

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Cheryl M Jekiel August 23, 2018

Katie - Good to hear from you.  Like your ideas.  Thanks for sharing them.  Cheryl

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