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An Executive Coaching Model: The Challenge Exercise

Evaluative comments from Training Participants about the Challenge Exercise:

I must say the best part of the training was the Challenge Exercise. I described my problem to the group. They asked questions. I outlined to them my plan of action. They declared it was wise and thoughtful. I felt validated! - Kathleen of Ashburn, VA.

The Challenge Exercise changed my response to my work situation. I must have been viewing it too narrowly. I received three different perspectives and was able to create a more focused response. - Patricio of Ft. Lauderdale.

How interesting the challenge exercise was! Initially, I did not think I had a problem or issue to share with the group. After I heard my other group members, I realized that yes, I could use some feedback on an issue. Great! - Diane of Baltimore, MD

This may sound odd. I have had a work issue for quite awhile but I had not really taken the time to thoroughly examine and problem solve. The Challenge Exercise did exactly this. Although I appreciated the feedback, I had actually created my own plan of action during the planning for the exercise and when I summarized such. - Mauricio of Texas


Most participants attend my trainings because they have a particular issue or problem. These issues could be with a partner, employee, employer, vendor, etc. They could involve partnership, team, or performance problems.

I teach a wide variety of courses:

- Negotiation

- Mediation

- Conflict Management

- Persuasion and Influence

- Critical Thinking

- Getting Results Without Authority

- Leadership

- Employment Law & Human Resources

Yes, but…Before I instituted the Challenge Exercise, participants in class would, during the class, present their individual problem. Others in the class would then offer ideas and suggestions. Usually for each idea thrown out, the person with the problem would respond:

- Yes, that is a good idea, but it won’t work.

- Yes, that is a good suggestion, but we tried that.

- Yes, that is good advice, but my issue is different.

So, very quickly the person with the problem would dismiss ideas quickly without listening to all feedback and every comment. Overall, this was not helpful and I thought something needs to be created, an exercise, that might persuade the person with the problem to listen, question, and possibly receive some help towards resolution. Thus, I created The Challenge Exercise.

The Challenge Process

A vital part of each class is The Challenge Exercise. This is a random group exercise.

Planning: Usually planning for this is homework in preparation for the next day. Each participant takes some notes on a problem or issue that they want to share with the small group in order to get feedback, advice, ideas, different perspectives, or validation. Directly before the exercise they are given five more planning minutes to review. The large group is then randomly divided into groups of 3-5.

Step #1: Each small group decides who is going to go first, second, etc. Talker #1 goes first. This Talker is given a certain number of minutes (in class, we allow 3). This is the gift of uninterrupted time. The others in the group, the Listeners, simply listen, taking notes and not interrupting.

The buzzer or bell rings.

Step #2: This step is purposefully entitled, Clarification Questions. The title is important. Listeners are asked not to start problem solving, or giving feedback or giving advice. Instead, they are truly asking questions that seek to illuminate the Talker’s story. The Talker is asked not to continue telling the story or elaborating but instead specifically respond to the questions of the Listeners.

Step #3: This step is the real reason this exercise is called “The Challenge.” During this step, the Talker does the listening. The Talker must sit back (for a number of minutes-in class, 3) and listen to the advice and feedback from each Listener. The Talker can only take notes.

During this stage, the Talker is encouraged to actively listen. Not to combat the advice, but instead absorb and think about it.

Step #4: This may be the fun step. It is a time when all group members can speak. The Talker can respond to the suggestions, feedback, and advice. The Listeners can elaborate on their ideas.

Some folks call this the 3-2-3-2 (minutes) exercise.

Questioning Types

Questioning skills is a large component of this exercise.

It is helpful to divide questions into four types: open, focused, closed and leading.

- Open questions usually begin with What or How. What happened?

- Focused questions narrow the issue. What happened last night?

- Direct questions can usually be answered by a one word response: Yes, No.

Did you drive your car last night?

-Leading questions usually have the desired response within the question.

Should you not have left your car at the restaurant and taken a taxi home?

During Step Two, I encourage the Listeners to ask clarifying questions using open and focused questions, plus some direct questions.

Body’s Clock

I usually conduct this exercise, if possible, on a Tuesday around 10:30AM. The reason? Most research shows that in the United States, most people are productive on Tuesdays, rather than Wednesdays, Thursdays, Mondays and last, Fridays. On Fridays, we are going to the mountains, to the beaches, or vacation or time off. Mondays are often consumed by making up for the weekend.

Research also demonstrates that mid-morning for most folks is the most productive.

- Early mornings: Time for light exercise and eating.

- Late mornings: Problem solving, critical thinking.

- Early afternoons: taking a nap.

- Early evening: exercise.

Lessons from the Challenge Exercise including “The Gift”

There are many:

Consider how to respond when a person says that they want to talk with you.

When a person says that they want to talk with me, I want to know the purpose.

If a person says, I want to share information or I want to vent, then I am ready. Instead, if a person says "I want your advice or counseling or feedback," I would not be ready. I would ask them to give me a summary first and then we shall schedule a meeting. In this way, I can give meaningful and planned feedback, advice and counsel.

Value of Summarization

In Step One of the Exercise, the Talker must summarize a complex issue or situation in a short amount of time, such as, 3 minutes.

Skill of questioning. Step Two focuses on clarifying questions.

Different perspectives

So, often people get stuck in problem solving because they are viewing the situation through one lens. Sometimes, they need various perspectives to set the stage for creativity. They need “a fresh set of eyes.”

Often it is helpful to have a fresh set of eyes within the organization and outside the organization.

One of the best ways to envision this is to think of a piece of art. Ask eight people to title this art and tell you what they see. It is often amazing, and yet expected, that one person sees a daffodil; another, sunrise; another, a conflict situation, etc.

This, is exactly what happens during the Challenge Exercise.

Encouraging Critical Thinking and Brainstorming

Because the Challenge Exercise is so organized, the stage is set for critical thinking and brainstorming instead of jumping to conclusions or making assumptions.


Sometimes, in a conflict situation you envision what could be a good solution; that is, one that meets the interests of all involved. But you are a bit unsure. In this exercise, you bounce off the idea to others. These others may validate some or all of it. So, you leave feeling confident that you are on the right track.

Active listening works!

Most professionals have taken some classes or had some exposure to “active listening.” In class, it often seems or feels silly. In real life, it works! In active listening, you are present. You are not thinking of a response or the next thing you must say or do. Instead, you are WITH the talker.

What is active listening? It is,

- Summarizing

- Asking questions

- Being engaged

- Echoing key words or phrases

- Withholding value judgments

- Pay attention

- Listen for accuracy, for empathy

- Listen with the whole body

In addition, take notes, remove distractions, and find the right setting.

Listening - The Gift

All of us have a gift that we can offer. That gift is total, being-present listening. People are begging for such. You often hear:

- "May I finish this sentence?"

- "May I finish this thought before your wisdom can be conveyed?"

- Necessity of planning even for this exercise.


Often a person will have an issue or problem. This problem might fester for awhile. They often have not sat down to really summarize this issue, think through the options, and do problem solving. This exercise gives them this opportunity.

Grading "The Challenge" Exercise

Just for fun, I often ask the participants post exercise to self-grade according to the following matrix:

- 20 points: During the exercise, did you give an effective summary?

- 20 points: During the time when others were describing their situation, did you actually listen or did you start giving advice?

- 20 points: When your group partners were giving you advice, did you listen or were you protesting it, either vocally or in your mind?

- 20 points: During the stage of clarifying questions, were your questions clarifying or were they leading?

- 20 points: During the last stage of free-flowing discussion, did you actually discuss or continue to elaborate on your problem or issue?

Goal=100 points.


So often in classes or trainings, participants bring up a problem or describe a situation, wondering what they can do. Other participants may make suggestions, but the one with the problem is often dismissive and mostly, does not listen.

Thus, I created The Challenge Exercise which is a logical communication process that is most likely to lead to a resolution or at least ideas for problem solving.


See Recommended Books under “Blogs” drop down menu. Clicking on any book will lead one to the discounted Amazon site.

Roy J. Lewicki is the author of 'Essentials of Negotiation', published 2015 under ISBN 9780077862466 and ISBN 0077862465. Publisher: McGraw Hill Higher Education

The Conflict Resolution Training Program, Leader’s Manual, ISBN: 0-7879-6077-2. Prudence Bowman Kestner and Larry Ray

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