The most important thing I learned is that soldiers watch what their leaders do. You can give them classes and lecture them forever, but it is your personal example they will follow.” – Colin Powell

After nearly a decade of teaching in higher education, I often tell students that my courses are a semester of performance coaching disguised as a class. While the knowledge transfer typical of teaching is a constant and ongoing process, there’s a strong coaching component that exists just below the surface. Every assignment is selected deliberately to impart new ideas, but also to spur critical analysis and self-reflection. Between those assignments, I pose carefully selected questions that they respond to in journals, allowing me to personalize their learning experience while helping them navigate the world around them.

Oddly enough, the teaching-coaching-mentoring spectrum that served me so well in uniform continues to pay benefits long after I threw my boots over the wire. It’s never enough to simply teach. We have a commitment to the long-term growth and development of our people. Some of that happens through mentoring, but most of it comes with coaching. The best leaders commit early on to building the bench, to growing the next generation. And those habits—ingrained over years of leading others—are ingrained in who we are.


When it comes to personal coaching, there are few better resources than Michael Bungay Stanier’s, The Coaching Habit. The underlying philosophy behind his approach is simple: “coaching others helps you.” A good coaching habit allows your efforts to have more impact in the workplace. First, it helps your team become “more self-sufficient by increasing their autonomy and sense of mastery.” Second, it helps you to regain and maintain focus, so you and your team are directing your time, energy, and resources where they have the most impact. Third, it helps you and your team to build a deep connection to work that infuses meaning into your efforts.

Stainer approaches coaching through seven essential questions that help to elevate performance in a transformational sense. The questions prompt open dialog while emphasizing deep listening—“Ask just one question [and then be quiet].” Effective coaching begins with the Kickstart Question: “What’s on your mind?” This helps to break the ice and spur a conversation. “One of the reasons [leaders] don’t coach more often,” Stainer offers, “is that they don’t know where to start.” A good opening question makes all the difference. This is followed with the “AWE” Question: “And what else?” Stainer notes that the AWE Question “has magical properties.” With a single question, you open a portal out of thin air to “more wisdom, more insights, and more possibilities.” In turn, those help you make better decisions, refocus your efforts, and buy time to extend the conversation.

The allows you to push the dialog to the Focus Question: “What’s the real challenge here for you?” We tend to be really good at solving problems. Unfortunately, we’re not quite as good at identifying the right problem to solve. The Focus Question cuts to the chase, identifying the root problem, specific to the individual and situation. This leads to the Foundation Question: “What do you [really] want?” Stainer also calls this the Goldfish Question, because it often elicits a bug-eyed, gape-mouthed response. We often don’t know what we actually want,  but this question compels us to define success for ourselves—what “right” looks like. The next query, The Lazy Question, asks simple: “How can I help?” This helps to reinforce roles and boundaries while clearly ensuring the other person takes ownership of the solution. You’re here to help, not solve their problem for them.

This ultimately leads to the Strategic Question: “If you are saying yes to this, what are you saying no to?” As Stainer remarks, this question “brings the commitment out of the shadows … a yes is nothing without the no that gives it boundaries and form.” Assuming that your team is already working at maximum bandwidth, when someone agrees to take on more, it comes at a cost. Something else has to give. The Strategic Question helps to define that in blunt terms. Finally, no coaching session has true value without the Learning Question: “What was most useful to you?” Coaching is about learning moments. Those learning moments don’t come full circle without the Learning Question, which offers an opportunity to reflect on what someone has learned and how they’ll put that lesson to use in the future.


There’s an easy trap to fall into with coaching: providing the answers instead of asking the questions that help someone find their own answers. If you truly want to help your team grow, you can’t limit their autonomy through “helicopter leadership.” That doesn’t mean you can’t—or shouldn’t—offer advice. But rather than lead with that advice or prompt it with a fake question—“Have you ever thought of…?” or “What about…?”—offer it as an option after an impactful coaching discussion.

After decades of coaching people in a variety of leadership positions, recognizable patterns emerge. It’s often said that history doesn’t repeat itself, it echoes across the generations. The same can be said with the challenges people face: life tends to ebb and flow in a way that presents the same general circumstances. When those moments come, I try to offer some useful, if not friendly advice. We still have the same conversations outlined by Stainer, but this allows me to set some early boundaries for later consideration.

1. Make every moment count.

Our loved ones are aging, and we never get as much time with them as we should. Don’t grow old regretting that you missed out.

2. Never stop learning.

Your brain is a muscle and needs to be exercised regularly. Read a good book. Listen to a podcast. Watch a documentary.

3. Get comfortable being uncomfortable.

Don’t limit yourself to things that make you feel safe, or activities that you’re good at. Push your boundaries and expand your horizons.

4. Be the best version of yourself that you can be.

Don’t try to be someone else. Don’t make comparisons. Challenge yourself to be better each and every day.

5. Never leave anything to luck.

You create your own luck through hard work and commitment.

6. Picture the end.

When choosing a career path, look hard at the person at the end of that road. Make sure that’s someone you want to be and a lifestyle you want to lead.

7. Collect experiences, not things.

On the surface, it might seem like I violate this one habitually. But the mementos I surround myself with all come with a story (sometimes, an epic one). Unique experiences will make your life much richer and more rewarding.

8. Control your responses.

Life can be a rocky road at times. You can’t choose what happens, but you can choose how to react.

9. Work hard.

Your work ethic is your best negotiating tool. If your hard work isn’t earning you what you think you deserve, take your efforts elsewhere.

10. Build good habits.

Who you are in 10 years or 20 years is a direct result of the good habits you build, the learning you do, and the obstacles you overcome. Choose wisely. Make them count.


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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a senior fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and former board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.