The Accidental Coach

I became an executive coach by accident while having coffee with a friend who needed to talk about an issue with his business partner.

I often had these conversations. They grew out of my mid-career decision to leave a large law firm to become a business executive. That transition led to a steady stream of people asking me out for coffee to explain how I managed to “leave the law.” Then, we’d turn to their work issues.

I enjoyed these meetings. I’d sip my coffee, listen and provide a sounding board for solving sticky wickets. I revel in strategy and brainstorming. What I ignored, however, was the most important factor that helped me to lead change in my professional life.

At this particular coffee meeting, I had just emerged from four years of “working hard, having fun and making history” at Amazon during its early adolescence. Everything there was new and unknown. As a result, we constantly had to invent new approaches to new problems. The place was one vast, scary experiment. I spent my Amazon days directing our team to climb yet another hill without knowing what lay on the other side. They’d tell me no. Then, we’d talk about what would change their minds and where to go from there.

During the coffee meeting with my friend, I realized what my focus on strategy had overlooked. He described how his partner had upset him, because he not only disagreed with a proposed new direction but refused to discuss it. We talked about possible causes of his partner’s avoidance, what he might want and conversation openers.

Then, he said, “This has been helpful. Let’s do this again.”

I suggested another coffee meeting.

“You’re not hearing me,” he replied impatiently. “I want to pay you.”

“Oh … OK,” I said. Monetize what I enjoyed doing? Now, there was a concept.

“Great!” he responded. “Now, would you please go deal with my partner?”

Uh-oh. That wasn’t how things were supposed to go.

Drawing from my Amazon experience, I realized what I’d missed: the visceral piece of leading change — the emotional edge that appears when you embark on the road to something new without knowing the outcome. It’s scary, but facing it is critical. Strategy alone will not produce change.

The Opportunity for Coaches

Coaches work with leaders to see possibilities, figure out where resistance might appear and find ways to overcome it. In this way, coaches can play an essential role in leading change.

To make change happen, everyone has to confront its scariness — leaders, followers and coaches. The key is to treat that scariness as an asset, not a liability, by learning about the people who would benefit from the change. That process can lead to discomfort, because it involves difficult conversations, but those conversations are vital to uncovering what people want.

As an executive, I had my eye on the strategic prize. However, to convince my team and stakeholders to enter unfamiliar places, I had to learn what motivated them. Coaching is no different. It just means that you facilitate change for another leader rather than for yourself.

The Coaching Challenge: Three Guiding Principles

Working many years in entrepreneurial environments taught me a lot. One of my biggest lessons was the depth of resistance to new ideas. It’s a risky business. To help leaders succeed, everyone involved must deal with opposition to change, including coaches.

Coaching is not a spectator sport. To win, you have to enter the playing field.

Three principles have guided me when working with others to help make change happen.

1. Make Steering Your Client Through the Scariness of the Unknown a Priority

Coaches must be willing to have awkward conversations to arrive at ideas that will make things better. To chart a new direction, you might bump into many uncomfortable issues for your client, including being out of control, conflict, low self-esteem, fear of failure and fear of rejection. In short, you have to contend with human messiness.

In the American business culture where I have spent my working life, talking about emotions is viewed as a soft approach. “Real” leaders talk about strategy … until they arrive at the coach’s office and close the office door. Then, they out pour their fears and doubts. Holding conversations that have no scripts is challenging, but it opens up new horizons.

For coaches, this process involves asking questions that explore strategic possibilities and what lies beneath for the leader and his or her stakeholders:

• What do you feel is the source of your alarm?
• If somebody else said that, would you have reacted the same way?
• What might be causing the other person’s hostility to your idea?
• What are you afraid will happen if you say out loud what your gut is telling you?

My coffee friend had no problem arguing tricky development deals. There are only so many ways to extract money from others and limit liability. The rest is choreography. But a conversation with his business partner on firm direction was a different game, and it came loaded with uncomfortable questions. What does the partner really need? What could he give up in order to accommodate that need? Why does the thought of doing so make him uncomfortable?

The outcome of such conversations is unknown, but therein lies the opportunity.

2. Take the Time to Deepen Understanding

In the fast, hyperconnected 21st century, we are losing the ability to slow down, breathe and realistically evaluate our situations to make good decisions. Reactivity to an environment of constant change has led to many uninformed decisions. Thinking is out of style, and it takes too long to separate facts from fiction. Further, once decisions are made, people might complain, failures could result and criticism will abound.

Coaches must help leaders navigate this reality. Slowing down the speeding trains of reactivity will help them find smart new ideas to fit their situations.

3. Embrace Your Own Discomfort With the Unknown

Few people love awkwardness. It’s even worse when you are the one causing it — which is your role as a coach. Pay attention to the possibility that you might be avoiding certain conversations, particularly when you sense your clients don’t want to have them. Watch out for:

• Unintentionally enabling their avoidance.
• Being deceived by their overconfidence.
• Ducking bullying behavior because of your own history.
• Being unwilling to put the relationship at risk by offering candid feedback.

These reactions are normal and could be conscious or subconscious. Either way, it is important to apply a healthy dose of self-awareness to avoid your own reactivity.

The Gift Coaches Offer

Coaching is an honor and opportunity. Never have people needed more support to explore the uncomfortable places where new ideas reside. Summoning up the courage to enter with your clients the scary world of new ideas, and the awkward conversations needed to achieve them, can make all the difference.