Coaching on the Fly

Creating Coaching Encounters Wherever You Go

by Tony Stoltzfus

A lot of coaching happens for me on the fly—in the aisles at church, on airplanes, during phone calls with relatives, with casual business acquaintances, you name it. It's a great way to change people's lives, and if you are in business as a coach, it will also get you clients. I want to share some tips about how you can use your coaching skills to change people’s lives every day—on the fly!

For instance, this past Sunday I had a significant coaching encounter with a guy at church between our two services. I asked about his business, since I knew he'd had a tough year with it, and as I focused on listening deeply to him, he began to share freely about it. A few questions helped him readjust his perspective toward God's activity in what had happened. He went away encouraged and more ready to face his week—all in about 5 minutes of coaching.

A Coaching Encounter is a short, one-time coaching session that usually happens on the spur of the moment. There are two things I look for when I’m deciding whether to move an everyday conversation into a coaching encounter:

  1. A Challenge
    We need to be talking about a significant challenge the person faces. You can’t coach someone when you are talking about the weather or the playoffs. And why bother to coach someone on something they don’t care that much about?
  2. Receptivity
    The person is open to change or to receiving a new approach. They are looking for something to help them meet their challenge. For instance, I got into another significant conversation at my son’s soccer game the other day. We talked about marketing and sports and various other things for a while, then the conversation moved into my new friend's career future and where he wanted to go in life. He was obviously searching for answers, so it was easy to slip into a coaching mode and start asking life purpose questions. Before I did so, though, I took an important step: I mentioned that I was a coach, and asked if it would be OK if I asked him some coaching questions. If you just dive right in and start asking people incise, personal questions with no warning, it can be a little disconcerting! (You come off like you are prying.) Get permission to have a coaching encounter before you just start asking 20 questions.

Here are some tips to help you generate more coaching situations in your everyday life:

  1. Believe in Yourself
    If you’ve been trained as a coach, you have some valuable skills that people all around you need. Believe that you have something significant to offer, so you don’t shy away when opportunity presents itself.
  2. Ask Deeply
    Cultivate the discipline of asking significant questions in every conversation. Books like Asking to Win or Leadership Coaching have great lists of conversation starters you can learn to use daily. It is much easier to generate coaching encounters when you are asking about people’s dreams or challenges than if you are discussing that horrible call last night in the Bears game.
  3. Show Genuine Interest
    Most people rarely have anyone really listen to their heart. So often in life, people listen to us only to hear the things that pertain to them (level one listening, as described in Co-Active Coaching), or they are just waiting for us to pause so they can start talking about themselves. People who are really interested in us, in who we are and what is going on in our lives, are pretty rare. Don’t lose sight of how transformational it is to just listen!
  4. Demonstrate, Don't Tell
    If the conversation does get around to coaching and the person is interested in what it is, I like to offer a coaching encounter: “Well, I could tell you what coaching is, but you’ll get a much better picture if I show you. Would you like to be coached for a few minutes so you can experience first-hand what it is like?” If they agree, I ask them to share a challenge they are facing and we are off and running!
  5. Network Significantly
    Depending on what you do, you may meet a lot of people in the course of your work or life that you network with. Learn to network at a significant level. If you have 10 minutes to get to know someone, cultivate the skill of getting to know who they really are instead of just what they do. I like to start those conversations by saying, “If you were going to give me a picture of who you are in 3 or 4 minutes, what would you say?” Then I answer the question first (so that I am the one taking the risk to open up) by talking about an event or two that really shaped who I am.
  6. Reframe
    Changing perspective is a technique that you can do in a few minutes. You can help people switch over to a growth perspective with a question like this: “Let’s say for the sake of argument that God custom designed this situation for your growth—that this is exactly the challenge you need to move to the next level. If that were true, what would you say God is doing through this?” A number of similar reframing techniques are demonstrated on the Powerful Questions: Changing Perspective CD.

Coaching encounters are a great way to get more practice as a coach and to introduce coaching to those around you. And I think you'll find that doing this is a lot of fun, too!


Tony Stoltzfus is a long-time coach, author of 11 coaching books and founder of the Leadership MetaFormation Institute, a innovative training school that teaches coaching the heart.