If You Want to Get Better at Something, Ask Yourself These Two Questions

It was the last race of the ski season. My son Daniel, 10 years old, was at the starting gate in his speed suit, helmet and goggles, waiting for the signal.

“3… 2… 1…” The gate keeper called out and he was gone in a flash, pushing off his ski poles to gain momentum. One by one, each gate smacked to the ground when he brushed by. As he neared the end, he crouched into an aerodynamic tuck to shave a few milliseconds from his time. He crossed the finish line —48.37 seconds after the start — breathing hard. We cheered and gave him hugs.

But he wasn’t smiling.

48.37 seconds put him solidly in the middle of the pack.

I had coaching ideas. Ways I could help him get faster. While I am an executive and leadership coach, I coach skiing on the weekends and I was a ski racer myself at his age. But I held back my feedback, hugged him again and told him I loved him. That’s what he needed in that moment.

Later though, I asked him how he felt about the race.

“I never get in the top 10.”

This is delicate terrain — coaching your own kids — and I chose my words carefully.

“I have two questions for you,” I said. “One: Do you want to do better?”

If the answer is “no,” then to attempt to coach would be a fool’s errand (a mistake I have made in the past).

“Yeah” he said.

“Here’s my second question: Are you willing to feel the discomfort of putting in more effort and trying new things that will feel weird and different and won’t work right away?”

He was silent for a while and I let the silence just hang there. Silence is good. It’s the sound of thinking. And this was an important question for Daniel to think about.

I believe — and my experience coaching hundreds of leaders in hundreds of different circumstances proves — that anyone can get better at anything. But in order to get better — and in order to be coached productively — you need to honestly answer “yes” to both those questions.

Maybe you want to be a more inspiring leader. Or connect more with others. Maybe you want to be more productive or more influential. Maybe you want to be a better communicator, a more impactful presenter, or a better listener. Maybe you want to lead more effectively, take more risks, or become a stronger manager.

Whatever it is, you can become better at it. But here’s the thing I know just as clearly as I know you can get better at anything: you will not get better if 1) you don’t want to and 2) you aren’t willing to feel the discomfort of doing things differently.

One senior leader I worked with became defensive when people gave him feedback or criticized his decisions. He wanted to get better, he told me, and he was willing to feel the discomfort. So I gave him very specific instructions (learned from my friend Marshall Goldsmith): Meet with each member of your team and acknowledge that you have struggled with accepting feedback and tell them that you are committed to getting better. Then ask for feedback — especially ways you can be a better leader — and take notes. Don’t say anything other than “Thank you.”

“It took every restraint muscle in my body not to get into a conversation about their comments,” he told me afterwards. “Especially because I felt they misunderstood me at times. It was beyond uncomfortable. And I messed up a few times and had to apologize. But I did it — and they haven’t stopped talking about what a welcome change it’s been.”

Learning anything new is, by its nature, uncomfortable. You will need to act in ways that are unfamiliar. Take risks that are new. Try things that, in may cases, will be initially frustrating because they won’t work the first time. You are guaranteed to feel awkward. You will make mistakes. You may be embarrassed or even feel shame, especially if you are used to succeeding a lot —and all my clients are used to succeeding a lot.

If you remain committed through all of that, you’ll get better.

I now ask those two questions before committing to coach any CEO or senior leader. It’s a prerequisite to growth.

I sat silently with Daniel for long enough that I thought he might have forgotten my question. Sitting in the discomfort of that moment, I realized that this was a new behavior for me too. I’m used to jumping in and trying to help him. Now, I was sincerely asking him whether he wanted my help. I was honestly OK with whatever answer he gave me — and it felt a little weird. But the more I settled into the silence, the more comfortable I got with just sitting with him — which I found I loved doing.

Finally, he spoke up.

“I think so” he said, “but it’s the end of the season. Can we talk about it at the beginning of next season?”

“Sure,” I said, “I’ll ask you again then.”