Identifying Teachable Moments

Turn challenges into opportunities through non-confrontational ways.

Perhaps it is the parent or teacher in me. I always seek to help other improve and reach their goals. If this strikes a chord with you, perhaps we are looking through the same lens. There are opportunities to help others see the horizon, go to the horizon again and still see further. There are many that struggle with challenges or failure, even small ones. Looking for ways to encourage and show compassionate guidance may be the only light seen in the midst of turmoil.

Identifying teachable moments

There are many opportunities to share when obvious things come up like a failed assessment or a poor suggestion is espoused. This could occur in the academic or corporate environment or even in social settings. Remembering time in Boy Scout leadership, there were no shortage of these opportunities. It is important to note here, being active and direct subverts being tactful where safety is involved.

Non-confrontational sharing

When the chance to coach someone through a situation arise, try storytelling as a way to wrap velvet around the situation and diffuse it. The use of anecdotal information could soften the isolation felt by the failure. Aesop, Mark Twain, and Walt Disney were great storytellers. Their memorable tales usually pointed back to a character flaw that was somehow changed by the experience. Perhaps your shared story will have a similar impact.

1. Notice body language

There are several tell-tale signals indicating potholes on the road to success. Facial expressions and body language are key indicators of inner struggle. But what if it isn’t so obvious. Don’t be too quick to dismiss the “I’m fine” or “Nothing’s wrong” response. Recalling the Train the Trainer class at Walt Disney World, we were encouraged to always ask three times in a gentle way. The first response could come out of embarrassment, the second may open the door to sharing and the third response would usually be genuine if the requester showed sincerity.

3. Responding even when you don’t know

Here’s a situation that comes up more often than one would like. Let’s face it, no one knows everything, and it would be arrogant to assume one does. While some people know a lot about something, there are still gaps. While this may occur from a subordinate to a leader, instead of being red-faced and caught blindsided, try (and be prepared for) a different approach. Instead of flatly saying “I don’t know,” which is still a perfectly truthful and positive answer, suggest that you find the answer together. This comes across softer as a learning opportunity rather than pointing out a perceived weakness.

4. Understand the differences

One consideration frequently overlooked is how the other person processes information. With that being said, note some people are “visual” learners while other learn better absorb better by doing (so-called “tactile” learners). While this may be preaching to the choir for the teachers in the audience, others may be completely unaware of the impact here. Evaluate why the other person had a challenge, perhaps the situation didn’t present itself in a way where their best use of their skills could be used. For example, someone is great at analyzing data. Then they struggle through a labored presentation due to a fear with public speaking. Offering help or guidance with shorter talks could be a confidence builder.

5. Share personal experiences

It has been said we are all on the same ring, just at different points. Sharing personal challenges in the same situation and how you overcame them becomes relevant and builds bonds. Look for ways like this to not only help but instill an esprit de corps having longer-term benefits. Perhaps you have been on the job longer and found a faster way to do things you figured out on your own. Sharing this with the “new guy” may go a long way for morale and setting yourself up as the expert. While the person getting coached gets the benefit, management may take notice as well.

5. Notice emotions

While body language and facial expressions are a key indicator, some people are less expressive physically. Look for signs like being withdrawn or reticent to participate. This may point out someone being at risk of withdrawing to the point of non-participation. It should be a coaching opportunity to share team collaboration and participation is paramount to everyone’s success. Coaxing is far from coercion and yields better outcomes. An opportunity here would be to ask questions the other person would certainly know, bolstering confidence back into the group.


The most important fact here is we want to help others improve. This builds confidence and everyone benefits. It doesn’t matter if it involves the youngest Cub Scout or corporate executive, what matters here that approachable coaching without being demeaning or confrontational gives the other person room to process and absorb feedback given as a gift and not as a correction.

To Your Success,
William R. Wheeler

Bill Wheeler Headshot

Hi! I’m Bill Wheeler

Master writer, storyteller and remote workstyle expert, I have worked remotely for over 17 years now. I can honestly say it is absolutely possible to work anywhere, anytime. It is my passion and mission to help others learn new skills and be more fulfilled and productive.

Our clients trust us, why shouldn't you?

These are just a few of the companies that have trusted us to get them world-class results. We’ve worked long and hard to gain the trust of companies like these, let us show how hard we work for you and your goals. Call (904) 468-7659 today.

William R. Wheeler is a business consultant, storyteller, writer and training expert. He has decades of experience with helping individuals and businesses clarifying and reaching their goals. He has written books, courses for colleges, universities and businesses and countless articles. Follow him on Facebook, Instagram, LinkedIn or through his website at

To schedule a no-obligation needs assessment, book an appointment here or call (904) 468-7659 today.

    Leave a Reply