Mentorship with an Expiration Date: Why Great Leaders Recalibrate

In a recent Harvard Business Review study aimed at identifying the qualities that set apart the most effective corporate executives from their peers, 75% of interviewees credited their success largely to the support and guidance of mentors. Wealth management entrepreneurs certainly possess intelligence and ambition. What they often lack, however, is the perspective of someone who has traveled further down the path. The right mentor at the right moment can help accelerate your thinking, open new avenues, and challenge you in ways that no book or podcast ever could.

But here’s another reality that most leaders overlook: not all mentors are meant to remain with you forever. Some relationships shift and evolve over time. Others, however, simply fulfill their purpose or reach their conclusion. Therefore, the important question you need to ponder and carefully evaluate is: 

Do your current mentors align with your vision for where you want to go, or are they holdovers from where you've already been? 

THE ROLE OF A LEADERSHIP MENTOR

Entrepreneurs, particularly those who have expanded their firms beyond $1 billion in AUM, often see mentorship as something they give rather than something they require. 

However, that assumption is misguided.

The most successful leaders continue to learn. They seek out those who have successfully overcome the obstacles and challenges they now face—those who have navigated transitions, scaled operations, or let go when it was time. Mentors aren’t just about support; they’re business accelerants. However, among the overwhelming majority in the HBR study who believe mentoring is crucial, fewer than 40% actively maintain a mentoring relationship.

Let’s be clear: mentors aren’t life coaches. They’re not emotional support animals. And they’re not celebrities you follow on LinkedIn. A true mentor does three things:

1. Brings pattern recognition from direct experience
2. Asks more insightful questions than you’re asking yourself
3. Shares lessons from failure as well as success

This isn't about asking Jim Collins what he’d do. It's about finding someone who has been where you’re trying to go and who will tell you the truth (not just give you a pep talk and cheer you on).

Mentors are not business coaches either. Both are valuable, but they are not interchangeable.

• Mentors provide personal experience and situational insight.
• Coaches are trained to assist you in uncovering your own thoughts and changing behaviors.

You bring varying expectations, diverse structures, and distinct requests to each. Your coach reflects your image. Your mentor guides your direction.

CHOOSE THE RIGHT MENTOR & STRUCTURE THE RELATIONSHIP

Not every mentor is suitable for every season, and there are strategies you can use to choose more thoughtfully and intentionally:

1. Begin by identifying your current learning gap. What are you focusing on—succession? Scaling? Stepping back? Professionalizing your organization?
2. Seek out someone with relevant scars and victories. They’ve made the tough decisions. They’ve occupied the position you’re in now and skillfully navigated through turbulent waters.
3. Test for alignment. Is the individual willing to engage fully and challenge your assumptions? Do they ask questions that make you pause and reflect?
4. Be clear about why you’re choosing them. Don’t just say, “I admire your success.” Instead, try saying something like, “You’ve built a multi-generational firm with a strong culture. I’m wrestling with how to do that now, and I’d really value setting up a couple of short conversations this year so that I can learn from your experience.” 

What should a mentoring relationship look like? This is where people often miss the mark—assuming that the quality of the relationship is measured by the frequency of meetings or the time spent together. It’s not; instead, it is measured by relevance and readiness. A powerful mentoring relationship might consist of:

• Two 30-minute conversations per year
• A quarterly article accompanied by a thoughtful question
• A particular dilemma where their insights assist you in navigating complexity.

Remember that clarity earns respect, while vagueness often gets overlooked. Therefore, be direct in explaining what you wish to achieve and aim to structure the relationship this way:

• Be direct in your request. What specific insights are you asking for their help with?
• Arrive ready. Avoid wasting your mentor’s time with unnecessary updates. Focus on the main challenges and questions you’re facing.
• Follow up. Inform your mentor about how you incorporated their advice into your decision, even if you took a different path.

This final point is important. Mentorship does not involve blind obedience; it offers perspective. While you aren't obligated to take action, you are required to reflect.

PREPARE & EVALUATE

Before reaching out to a potential mentor, take the time to thoughtfully reflect on the following questions:

• What specifically am I trying to learn or solve?
• Why do I believe this particular individual will be equipped to help me?
• Am I ready to act on their input, or will I collect it and do nothing?

Then, during your initial ‘feeling out’ conversation, be sure to ask them:

• Have you ever mentored another professional in a comparable situation?
• What is the best way to engage with you while respecting your time?
• Would this be something you’d be open to participating in a few times each year?

Keep in mind that most successful people want to share what they’ve learned – but only when it’s clear you’ll actually do something with it. Therefore, be disciplined (unlike most leaders being mentored) and make it a point each year to review and consider:

• Which mentors do you currently have a relationship with?
• Whether those mentors are still aligned with the growth you’re pursuing or not.
• New challenges and areas where you require fresh input or a new perspective.

Some mentors will stay with you for decades, while others will serve a powerful purpose for a season or two. Honor both, but don’t confuse history with relevance. Be willing to recalibrate. Your business evolves, and your leadership challenges change; your support system should, too.

Lastly, remember that you don’t always have to agree with your mentor. It’s guidance, not gospel. You’re not seeking someone to make your decisions for you; you want someone who sharpens your thinking. If a mentor’s input prompts you to pause, reconsider, or adjust course – or strengthens your conviction in the path you’ve already chosen – that’s a win. Communicate when their guidance is helpful and demonstrate the impact. That’s how you build the kind of relationship that earns you the right to return with a new challenge in the future.

As an entrepreneurial leader, you don’t just need a business plan; you need a learning plan. Mentorship isn’t a favor – it’s a strategy. So, ask yourself whether your current mentor(s) are still relevant to the leader you’re becoming. If not, maybe it’s time to recalibrate.

Coaching Questions From This Article

1. Which area of your leadership development (i.e., strategy, people, capital, or scale) requires the most external perspective at this moment?
2. Who in the industry do you know who has successfully walked that path and might be willing to serve as a mentor?
3. Which of your current mentoring relationships needs the most refreshing, repurposing, or releasing to create space for the guidance you need next?

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