Coaching Tips for Managers - When the Bicycle Moment Occurs



My best boss was also my mentor. He coached me and supported my development, even though it meant I was likely to get promoted. He showed me it is possible for a manager to focus on results and develop their people at the same time.

When eventually I was offered a new position, I confided in him that I wasn’t sure I was ready. His response was,

“Remember – You know everything you need to know. You have everything you need to have. You are everything you need to be.”

This has become the mantra I repeat whenever I’ve taken a stretch assignment or felt unsure of myself.

In my own role as a leader, I share his attitude about development. A lot of people want to hire what they call “winners,” people who are already competent. But my definition of  ‘winner” is someone with the right values and with potential to grow into the job. It’s my job to help them grow. My reward for being a good manager is that the people who report to me move on. I don’t want them to stay out of loyalty. I want them to fulfill their potential – to know what their dreams are and then to reach for them.

Here’s what I’ve learned about coaching as a manager: It’s easy to be a coach when it means providing direction, giving advice and solving problems. Like most leaders, I’m good at it, and I like to do it. Fortunately it’s exactly what people need early on while they’re still learning.

But there comes a point where a shift in the relationship needs to occur – where you let go of actively advising them, and they take the lead. It’s what I call the bicycle moment.

Do you remember learning to ride a bike? Most of us had someone big running next to us, holding onto the fender, supporting us while we peddled. And at some point they let go. If you were like most of us, you continued for awhile and then fell. Where was the big person? Still there, watching from behind. They came to where you were sitting on the ground, praised your accomplishment and encouraged you to get back on the bike. Did they put the training wheels back on? Probably not.

This is a critical point – it is the moment of empowerment. It is the moment of shifting from dependence to independence. And as a leader, if you don’t support their making that shift, your people will remain dependent on you.

How do you recognize that moment – that it is time to let go? I consider these four questions:

  • Do they have the skills and knowledge they need?
  • Have they demonstrated their ability to do this in other settings or similar ways?
  • Do they want to do it?
  • Do they have the resources they need to do the job?

If the answer is yes, it’s time to let go.

This is the most difficult transition because it means a huge shift in your role. Letting go doesn’t mean ending the relationship. It means changing it. Now when there is a problem, instead of telling them what you think, you keep your opinion to yourself and ask them questions like,

“What do you think?”

“What did you learn?”

“Where can you get help?”

It’s a listening and reflecting role.

The point is to help them to become self-reliant problem-solvers.

– To know what they know.

– To know where and how to access help when they need it.

– To develop the confidence they need to move forward independently.

At that point, you watch – but from a distance, like in the bicycle moment. And your gratification now comes from watching them fly instead of from being the wise advisor.


26 comments to Coaching Tips for Managers – When the Bicycle Moment Occurs

  • Nice post Jesse Lyn. Too few coaches know how to let go in my view and move from directive behavior to empowering behavior-largely brought about by asking much more open ended questions and then doubling or trebling the time spent listening (by offering only gentle follow up when necessary such as “tell me more about that” etc.

    • Thank you, Jon. “Tell me more” is an excellent addition to the list of questions.
      I agree that this is a difficult transition to understand. Too often managers continuing to provide direction when it is no longer needed or wanted, and what was once helpful now becomes a problem. Or managers go to the other extreme – they delegate and disappear. Managers need to understand that their role now is to support their direct report in discovering the answer – not leading them to what you believe is the correct answer through “socratic questions” – but by asking open-ended questions, allowing them to discover their own answer.

  • Alicia Lopez

    Jesse Lyn,

    Thank you for your post. Reminds all of us who coach that it’s important to always find ways to empower individuals and teams to lead, grow and share their gifts and talents. Your post came at a perfect time! I’m working with program coordinators from a non-profit organization called “Esperanza.” I worked hard to develop a series of questions that will lead them to the next phase. Thanks for sharing your experiences and your awesome questions!
    You truly are an inspiration to those in search for new ways of leading and inspiring!

  • Tammy Stoner

    Thanks. Great post. Riding a bike reminds me a little bit of me and you. You are a great coach!

  • Lovely post, especially the moment of empowerment insight. I think it’s really important to move the coaching for self-reliance to the self-directed mode at this point. In my coaching work I ask them questions like; ‘Suppose you are successful x months form now, what will you see yourself doing?’ ‘What will others see you doing?” ‘What will you notice about yourself that will tell you that you are doing a good job?’ “What will be the first small signs that you are making progress in the next few weeks?’

  • So true, Jesse. The art of leadership is knowing when to let go – not too soon and not to late. Then it’s knowing the right way to be helpful after you’ve let go. I’m going to send this post to my daughter-in-law who just got a huge promotion.

  • I love the bicycle analogy! That moment is truly magical. When you both let go and the other person takes control. Think of the encouragement you give your little one at that moment- “You got it- you can do it”! Interestingly, I just wrote a post on the importance of answering the “why” questions in career growth. Much easier for managers to answer the “what” and move on- but the “why” is where “self-reliant problem-solvers” are made. I also love your question- “Do they want to do it?” I think this important truth can get lost in the mechanics of training. Tough to succeed without inner motivation! Thanks for sharing Jesse!

    • “The ‘why’ is where ‘self-reliant problem-solvers are made.” – beautifully said, Joe. The ‘why’ question is the basis of most of our decisions and without the answer, it is impossible to be deeply connected to what you really desire. I enjoyed your post The Why Theory. I included the link here to make it easy for readers to access it.

  • Indeed! What a lovely way to describe it. What I like about it the most is the idea of letting go to pursue something greater – for unselfish reasons. Leaders are easily corrupted by power, money and sometimes, attention, that they forget their ulterior role – to lead, and this to serve.

    Thank you for sharing Ms. Stoner! More power to you!

  • I love the bicycle analogy Jesse. I do enjoy your blogs, they are clear and simple and encourage reflection. True employee empowerment occurs when leaders at all levels of the business take time to develop people. Work place leaders who have been developed and empowered themselves are more likely to do the same for those they lead.

    • Thanks for your kind words, Jenny and for sharing your thoughts on development and empowerment. Your point is well-taken. In workplaces where leaders have been supported in their own development it is more likely they will support the development of those they lead. Part of the reason is because they had good role models who showed them how (like I did) and also because these are organizations where learning and empowerment is embedded in the culture. However, anyone can decide they want to support the development of their people, and it is to these courageous leaders that I dedicate my posts.

  • Dave Howe

    This puts into words what I try to do as a Battalion Chief in our Fire Department. I think it is also a useful way to look at raising teenagers!

    • Excellent point, Dave. This is useful for anyone who supports another’s development, no matter what the context is – as a parent, a teacher, a coach, a mentor, and even a friend. Unfortunately, too many managers don’t understand that it is their responsibility to support the development of their people. And even when they do see it as their responsibility, they don’t always know how to do it – especially to make this difficult transition. It is encouraging to hear this is your approach as a leadership at your fire department. Thanks for sharing your thoughts, Dave. I hold an especially high regard for your profession as my son is a volunteer fire fighter.

  • I love this post, Jesse–everything about it. Thank you for continuing to share your wisdom in an engaging and memorable way.

  • Robert Drescher

    Hi Jesse

    The bicycle analogy is right, but having gone through it not that many years ago, I realized that it is very similar to how I built people under me.

    The first time you let go they usually fail, but that isn’t a bad thing, it teaches them two very important lessons. One that to succeed you have to keep trying. Two you can recover from mistakes even if you get bruised occasionally.

    An older executive once told me that “a managers role is to utilize those people under him to the best of their ability, and you can only improve their ability by allowing them to try new things. You just have to be ready to come to their aid when they fall(make a mistake), pick them up dusty them off (step in provide advice and help them analyze what went wrong), and let them try again.”

    • Hi Robert, It is gratifying to see that one’s instincts were on target. Falling is part of learning. It is hard for a mentor, boss, teacher or parent to watch them fall, but when you are certain they know what to do, the best thing you can do is be there to cheer them on, but hold off on the advice. They must discover that they already know the answer and learn to trust their judgment. This nuance makes this transition point especially difficult for many people to understand because their natural inclination is to provide advice, rather than helping them find their own answer. Thanks for sharing your experience.

  • Hi Jesse I agree with you generally when I give advice it is never one directional, I honestly have never believed the line there is only one way to do anything. That being said the big thing I always liked doing first is actually helping them figure out what went wrong, 99% of the time by the time we go through what happened they have already generated good ideas to solve it. Most of my advice is often been in just helping regain their courage to try again, sometimes it helps when you can show them that they weren’t totally wrong just outside factors caused the failure, so all they really need to do is adjust for them.

    One of my biggest worries though is that to often we sweep mistakes away without taking the needed time to learn what really went wrong, and then making sure everyone else in the organization knows what happened so you avoid repeating the error. Edison had the right attitude, you learn more from failures than you do from successes, and the reality is they happen far more often than we like to admit. Hell some failures have actually proven more valuable than the success would have been juust ask 3M PostIt Note glue was a failed attempt to make a super glue, yet it market is hundreds or even thousands of times the size of that for super glues.

    • You make some excellent points, Robert. The “bicycle moment” is all about helping people regain (or maintain) their courage. By helping them examine their mistakes in a non-judgmental way, they can learn from them, rather than keep repeating them. You offer some excellent examples to illustrate this. Thanks for sharing your own experience and wisdom.

  • Hello Jesse, your blog post is very inspiring. My boss is also my mentor. He often teaches me a lot of things regarding our business pros and cons. It’s very comfortable for me to become a great employee in his company because of my boss friendly mentoring. Jesse I hope you’ll learn more from your mentor and share the story with us.

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