How Issuing Challenges in Your Coaching Business Can Have a Life-Changing Impact

What life goals are you trying to achieve this year? Are they focused solely on business or do they focus on both your personal and business performance?

Allow me to tell you a story about a challenge I issued a client around fear and the power of overcoming it.

There once was a Financial Advisor I was working with, he was preparing for his upcoming wedding while also trying to grow a thriving business. He struggled with rejection and took some time to bounce back when it occurred. During our coaching calls, we would talk about the conversations he would have with his potential clients and what he might like to try differently. We were building on his strengths and he was seeing headway. Fast forward, 1 week before his upcoming wedding and I get a call from him.

“She left me!” he said.

The wedding was off.

To support his forward movement, we had a lot of work ahead of us. He could’ve chosen to let this define him. He sounded as though he was ready to, early 30’s and he said he was done. Ready to quit his job because he was afraid he would fail at that too and also give up on finding the right person.

As a coach, what was I to do?

After a few months, we had another call scheduled. I could have been primarily focused on his business results. However, I chose a different approach. As his coach, I was responsible for creating the coaching environment, one where he trusted me and knew that I had his best interest at heart.

A challenge is an idea you (the coach) come up with that you suggest to your client. During our conversation, I sought his permission and invited an assignment, a challenge if you will.

Go to the mall, and ask 5 beautiful women out for coffee. “What?” he said. The fear, we were trying to get over was rejection. So the objective was to build up his resistance to rejection. He should have asked and gotten rejected over and over again. Just as you will encounter when you are offering your financial services to people.

He went to the mall the next day, went into the first store and saw a beautiful. After a few minutes of talking with asked her if she wanted to grab a cup of coffee. To this day, many dates and 4+ years later, they are happily married. He also has a professional practice that is thriving and that he is proud of.

I get a wonderful call from him every now and then and hear in his happiness, thank you! If he wasn’t challenged, how long would he have struggled with that fear of rejection? What if he didn’t take action to overcome the fear?

Imagine if I used only words rather than inspire him into action? His life would look different. What I saw in him, was that he was capable, he was good at what he did and he had it in him to succeed. The achievement of his goals were all in his mindset and willingness to try.

As coaches, we listen, we use words, we inspire action, we invite strategies and shifts to help people live their best life.

Here are 6 tips to help you issue challenges to your clients that can be life-altering:

  1. Keep it simple, less is more.  Do not issue challenged frequently, save them for critical shifts.
  2. Look for stretch opportunities that compliment what your client is already doing.
  3. Be flexible. Let your client know that you are issuing them a challenge and set the rules, allow for yes, no and yes with a modification.
  4. It is not a command. The more trust you have built with your client, the more they know you have their back and challenges take trust.
  5. Make it easy. The focus is always on them, you do not want to overcomplicate things and divert the attention to yourself. Keep the challenge short and focused on pulling out their strengths.
  6. Congratulate a NO. If you issue a challenge and your client declines, encourage them for being clear on what they want. Your ego is not in play here, their success is.

Helping change lives is a privilege. The transformational coaching I offer includes not only the discipline of coaching, but it also includes change management and the science of well-being.

His fear of rejection was solved by coaching.

What we think is possible is just the beginning. Maintain momentum and make it a great day!


Jennifer Jimbere
Jennifer Jimbere
Jennifer Jimbere is an entrepreneur, International best-selling co-author of the Dream Boldly I Dare You series, World Class Coach and Business Consultant. A recognized authority on change management, profitability, and organizational turnaround, she has served as an advisor to thousands of individuals and organizations around the world for more than 20 years. Her work can be found on Jimbere Coaching & Consulting and Radical Joy Seeking Women's Club. Jennifer has also been named Influence Magazine 100 Authority and recognized as Coach of the Month, April 2019 by Strategic Learning Alliance.

SOLD OUT! JOIN OUR WAITING LIST! It's not a virtual event. It's not a conference. It's not a seminar, a meeting, or a symposium. It's not about attracting a big crowd. It's not about making a profit, but rather about making a real difference. LEARN MORE HERE



  1. Thank you Jennifer… Yes we must face our fears. Rejection itself is manifesting many fears without one realizing it. This is something to get through when you know you have had a big let down. I understand, and have lived it before. Thank you for this!

  2. As coaches we know our responsibility is to assist clients with discovering the right answers for themselves, yet so many times we go into ‘telling mode’ – we tell them what we think they should do. This is an excellent example of what we as coaches need to strive to do always. Appreciated how this simple challenge helped to bring about a transformation in the life of your client. Thanks for sharing.