Is There a Reason You May Not Have Any Mentors?
For the past decade or two, I’ve been fortunate to have an unusual number of mentors who have poured into my life. I’ve written about it more than once, including in an October 2014 post called What Is a Mentor?
Over the years, working with executives and leadership teams of every size and across industries, I’ve also noticed something else: many executives I meet have very few, if any, mentors at all.
So, being me, I concluded I was just a “lucky guy.”
Not long ago, I was sharing this with a group of executives, discussing how grateful I am and how sad I feel for leaders who go it alone. One of them, a longtime friend who happens to be a clinical psychologist, stopped me and asked:
“Did you ever consider that you have so many mentors
because you’re open to and actively solicit input from others?”
Believe it or not, I had never thought of it that way.
That single comment reframed the whole topic for me. Maybe there were things I had done, without even knowing it, that had brought these mentors into my life.
Having a mentor is so valuable that I think every executive should cultivate one. It isn’t magic or luck, so I want to break down for you what I did so you can do it too.
The first part is the hardest because it’s so counterintuitive: you have to ask people you respect for help.
Leadership Is Not a Solo Sport
Many executives quietly assume that once they reach a certain level, they’re supposed to have the answers. Asking for help can feel like weakness.
But over time, that mindset creates a lonely reality:
No one will tell you the truth when you’re about to make a mistake.
No safe place to process big decisions.
No one regularly asks you, “How are you doing, really?”
I can’t tell you how many successful leaders I’ve met who are surrounded by people all day long and still feel alone at the top.
They don’t necessarily lack smart people; they lack trusted voices who are both for them and honest with them.
That doesn’t make you stronger; it makes things more precarious.
Why Some Leaders Have Mentors and Others Don’t
Looking back, I don’t think I attracted mentors because I was especially impressive. In many cases, it was exactly the opposite! I was clearly not remarkable yet.
What I did do, as a leader fairly consistently, was:
Ask questions. “How would you approach this?” “What am I not seeing?”
Invite critique. “Tell me what I could have done differently in that meeting.”
Follow through. When someone suggested a book, I read it. When they gave advice, I tried it. Then I circled back and told them what happened. (Don’t ignore this step! The circling back is key.)
Express gratitude. I made a point to thank people for their time, their honesty, and their investment.
When you engage in that way, people notice. It’s rewarding to invest in someone hungry to grow and who actually uses what you share.
In other words, mentors didn’t just “show up” in my life. I made a habit of being: curious, coachable, and willing to act.
You can do the same.
Related Read: Slow Down to Speed Up
Photo by Vlada Karpovich: https://www.pexels.com/photo/a-man-and-a-woman-looking-at-papers-7433827/
In An Ideal World, Mentorship Looks Like
There is no secret formula for a thriving mentorship dynamic, but in my experience, the best relationships tend to have a few things in common:
Time together. You cannot microwave trust. Good mentoring requires regular, unhurried conversations over a period of time—often years.
Real questions, not staged updates. “Here’s what I’m wrestling with…” is a more productive starting point than “Here’s everything that’s going great.”
Pushback, not just encouragement. Encouragement is wonderful, but growth usually comes from the moments when someone you respect says, “I disagree,” or “Have you thought about it this way?”
Mutual respect. It’s not a lecture. It’s a conversation between two adults who respect each other. The best mentors don’t try to clone themselves; they help you become the best version of yourself.
Where Executive Coaching Fits In For Leaders and Their Teams
Sometimes the word “mentor” makes people think of something vague, informal, and occasional—coffee once a quarter, a phone call here and there. That can be valuable, but many leaders need something more intentional and structured:
A consistent space to step back from the whirlwind and think.
A seasoned outsider who isn’t entangled in office politics.
Someone who will ask the hard questions you might avoid asking yourself.
A partner who helps you turn good intentions into concrete plans and follow-through.
It isn’t always possible to find someone with the time to provide that.
That’s where executive coaching comes in. In many ways, it’s a formalized version of mentoring. You get the benefit of a trusted advisor, plus:
A rhythm of regular meetings
Clear goals and measures of progress
Tools and frameworks tailored to your leadership and your company
Honest feedback in a confidential setting
In our work with executives, we often function as that combination of mentor, coach, and thinking partner. We don’t tell you how to run your business; we help you see it more clearly, make better decisions, and become the kind of leader others want to follow.
Related Read: We've Got It Handled: The Value of an Outside Perspective
A Few Practical Next Steps
If you’re reading this and thinking, “I could really use someone like that in my life,” here are a few starting points:
Take inventory. Who are three people you respect—inside or outside your company—whose judgment you trust? Write their names down.
Initiate one conversation. Reach out to one of them and say something like: “I really respect the way you lead and think. Would you be open to meeting once or twice so I can ask your perspective on a few things I’m wrestling with?”
Be transparent. Show up ready to talk honestly about your real challenges—not just your highlight reel.
Ask for feedback. At the end of the conversation, try: “Is there anything you see in how I’m thinking about this that I should reconsider?”
Circle back. Express gratitude for their time immediately after your meeting, but then later, be sure to circle back. Read the book they suggested. Try their suggestion and let them know how it went.
Decide if you need more structure. After a few of these conversations, ask yourself:
Do I have the support I need?
Or would a professional coaching relationship help me move further, faster?
If you find yourself in that second camp, that’s where a formal executive coaching engagement can be a powerful next step.
We’d be happy to discuss what executive coaching could look like for you.
