The Leader Mindset #47

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Why Mentoring Often Fails and What Great Mentors Do Differently

Learn what it takes to be a great mentor in just 5 minutes

For most of my career, I’ve been against mentoring.

Not because I don’t believe in learning from others. I do. My skepticism came from how mentoring usually plays out inside organizations. Frequent meetings with long conversations. Very little clarity about what the conversation is actually meant to accomplish.

Too often, mentoring turns into a game of “who you know.”  A way for a small group of people to get closer to senior leaders. I’ve watched leaders with questionable readiness use “mentoring” to curry favor, landing stretch assignments, exposure, and promotions that felt premature. At the same time, I’ve seen high-potential leaders paired with disengaged mentors who barely showed up, quietly stalling their development.

That never sat right with me.

As someone who cares deeply about leadership development, mentoring felt thin. No skill building. Little practice. No accountability. And when the conversations ended, it was hard to say whether anyone was actually better as leaders than when they started.

So, I wrote off mentoring as ineffective at best. At worst, a political waste of time.

Looking back, that view was probably too extreme.

Here’s what forced me to reconsider.

Roughly 97 percent of Fortune 500 companies use mentoring in some form. That’s near-universal adoption. Are all of those organizations ill-informed? Probably not.

When you look at the evidence, a clear pattern emerges. Mentoring is associated with higher retention, stronger engagement, more internal movement, and deeper commitment to the organization. The impact is not dramatic (from a statistical perspective), but it shows up consistently.

Where Does Mentoring Fall Down

That’s when it hit me.

My frustration wasn’t with mentoring itself. It was with how unstructured it often is.

That informality puts the burden on the mentor. They have to know how to guide the conversation, create value, and avoid drifting into pleasant but pointless dialogue. The problem is that most mentors are never taught how to effectively do this.

That’s disappointing, especially because most mentors care, show up, and genuinely want to help. But few are educated on what makes a mentoring relationship effective rather than simply an enjoyable conversation.

I know many of you want to be great mentors, not just a well-meaning one, a few intentional shifts can change how you show up for your mentees.

Luckily, they don’t take much effort.

What Actually Makes Mentoring Effective

Effective mentoring doesn’t need a formal program or strict structure. What it does require is intention and discipline from the mentor.

Here’s what that looks like in practice.

Be deliberate about fit.
Before you agree to mentor someone, ask what they want help with and where they are in their career. Compare that with your experience. If it doesn’t feel like a good fit, say so. It’s better to be honest upfront than to spend a year in unproductive meetings. And make sure the mentee knows they have an out as well.

Define the relationship early.
In the opening meeting, be explicit about:

1. What the mentee wants help with right now

2. How often you’ll meet, for how long, and how to reschedule

3. What confidentiality means in practice

4. What role do you play (sounding board, advisor, connector, perspective)

5. Expectations for both parties

Don’t assume alignment. Define it and revisit it as the relationship evolves.

Set a clear focus before every meeting.
Ask the mentee to send one topic ahead of time. Not an update, but a question, decision, or situation they want to think through. If nothing comes in advance, start the meeting by agreeing on the focus before anything else. This process is a non-negotiable and the responsibility of the mentee

Share your reasoning, not your résumé.
A great mentor helps a mentee sharpen thinking, judgment, and decision-making. One way to do this is to share a situation you’ve faced, then ask how the mentee would approach it. After that, explain what tradeoffs you considered and what you would do differently now. Avoid stories that don’t directly connect to the mentee’s situation.

Alternatively, spend less time on background and more time on:

• What decision are they facing

• What options do they see?

• What they’re uncertain about

• What assumptions are they making

If the conversation turns into a status update, redirect it.

Practice your coaching skills.
Ask questions that challenge the mentee’s assumptions and thinking:

• “What are you optimizing for here?”

• “What’s the risk you’re underestimating?”

• “What happens if you do nothing?”

• “Who else has to live with this decision?”

 Encourage additional mentors early.
Let them know you’re not the only voice they should rely on. Suggest others who can offer different views. Remind them that long-term development comes from a network, not from a single relationship.

Close every meeting with clarity.
Before ending, ask:

• “What stood out to you?”

• “What are you going to think differently about now?”

• “What do you want to pay attention to before we talk again?”

 Recontract the relationship periodically.
Every few months, check whether the mentoring is still useful and whether the focus should shift. If it’s time to move on, say so and end the relationship well.

Where I’ve Landed

I can’t ignore the research. When done well, mentoring creates real value for both the mentor and the mentee. That said, I see mentoring as a supplement to broader development efforts, not a replacement for them.

With that said, mentoring only works when mentors have the skills and structure to guide conversations that actually create value.

I’ve been intentionally vulnerable in this article about how my thinking on mentoring has evolved. Now I’m curious about yours. Have you found mentoring valuable? What do great mentors do differently? Have you ever had a bad mentoring experience?

I’d love to hear your perspective.

Andy Noon, PhD

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Thanks for reading and look forward to seeing you again next week.

Andy