The best advice I ever received from a leader


A few years back, I had the opportunity to join 30 leaders at CEB in a learning session led by Tom Monahan who had served as CEO for over a decade. Tom was known for possessing this brilliant balance of awesome, yet simple insight flavored by cult movie classic references.

In one particular learning session he told us, “As CEO, my job is to look for unfair fights.”

Some of us in the room chuckled. We knew where he was going, but hearing it put so simply really captured our attention.

“I look for unfair fights that we can always win so we can shift more resources toward those fights,” he continued.

As he unpacked this advice, I realized how impactful it would be to me then and even today. Organizations tend to get stuck emotionally on what they want to accomplish—they become dogmatic about going down a pre-determined road instead of stopping to critically evaluate what they’re the very best at. At the heart of Tom’s advice was this core tenant: in order to be successful, we must remain objective in how we make decisions.

Good advice leaves a trail of success

Have you ever had someone give you advice that follows you everywhere you go?

Tom isn’t the only person who’s spoken into my life in this way, but I wanted to share his advice because it illustrates for me the very best in what a leader should be offering someone they advise. First, he knew his audience well: there were 30 of us in the room who all had some direct responsibility for preparing the ground for these unfair fights he’s on the lookout for. He also had tenure in some of our roles, giving him direct insight into what we needed to hear to be inspired and successful.

Perhaps you’ve never met someone who can speak so plainly to where you are today. Drawing from personal experience, I think that whatever our goals in life may be—whether we aspire to be good parents, to grow spiritually, to grow a company—being able to leverage someone else’s insights and wisdom isn’t optional. By learning to take their successes and failures and then apply them to our own lives, we have the opportunity to accelerate our learning and maturity.

When we’re asking for advice from too many sources

It’s also possible that you’re asking for advice all the time, from too many people, and find yourself in a place where you’re overwhelmed by all the potential options. If so, I propose re-setting how to approach general advice vs. mission-critical insight for high-impact decisions. When either approach is misapplied, the results can be devastating.

Finding a person with whom you have confidence is often one of the most important things a CEO/Founder can do—whether that person is someone like Tom, a leader I had exposure to occasionally, or a person with whom you meet regularly for intentional mentoring and coaching. Regardless of the nature of the relationship, when someone is offering advice that directly impacts you personally or professionally, ask yourself a few things:

  • Does this person understand me/my company’s vision?

  • Does s/he offer advice and insight that resonates as being fresh (aka not cliché or copy-and-pasted from a manual)?

  • Does his/her advice feel like it reflects a deep understanding of me personally and professionally?

  • Does the advice seem to only mirror the choices they have made in their own life?

Above all, we should be on the lookout for someone who’s known for applying wisdom judiciously in his or her own life. A coach or mentor doesn’t have to be perfect or only make good decisions—but they should have the humility to say when they don’t know the answer to something.

What advice has changed your life?

Advice comes in all shapes and sizes, which is why in the coming weeks I’m looking forward to sharing more insight and advice from people within professional circles and also within my personal life. I hope you’ll stay tuned.

In the meantime, if you have a few minutes, would you share with me the best advice you ever received from a mentor? I’m eager to hear what you’ve learned along your own journey.

* Photo by Nik MacMillan on Unsplash