mentor relationship

Finding a Mentor Isn’t Enough. You Need to Build a Relationship.

Mentors. Everyone wants one and few have a good one. At a recent TechCrunch conference in Boston, I led a discussion on mentorship. And I managed a mentoring program at The Capital Network, a Boston-based non-profit that educates founders and investors. Based on these experiences, here are my thoughts on how founders can create a successful mentor relationship.

Mentorship works best when the mentee leads

Counterintuitively, though the mentor usually has more experience, the mentee benefits most by taking the lead. When you’re looking for a mentor, ask them to work with you and make your asks specific.

When mentor/mentee relationships falter, it’s often because neither side is getting what they want. Mentees will say, “When I’ve met a potential mentor, it invariably becomes a one-sided discussion: I do a lot of head-nodding and the mentor does lots of talking.” And from the mentor side, “We agreed to deliverables and she didn’t follow through. I don’t know how serious she is about her business.”

What’s really going on? In the first case, the mentee thinks she needs to be deferential. Why not interrupt and redirect the conversation to focus on what really matters to you as a founder?

In the second, the mentee may have disagreed with the mentor’s advice but didn’t speak up for fear of offending. Better to look at it this way: your mentor is volunteering her time. It’s your job to make that easy for her. Being crystal clear about what you want will save you both time and ensure the mentor knows she’s contributing.

One mentor/mentee pair I worked with had a slow start. It took weeks to set up the first meeting. When the two finally connected, the mentee hoped for introductions to the mentor’s network. The mentor had no idea that was the objective. Finally, the relationship fizzled. The mentee could have simply said what she wanted, and, when it was clear the mentor wasn’t able to provide useful intros, put the interaction on pause. Instead, they continued to meet, generating more frustration than results.

By contrast, another pair met weekly for several months with the mentee arriving with specific asks that drew on the mentor’s experience. The founder followed through, focusing discussions on growing her business and making it fundable. Not only did the mentor join the company’s advisory board, but she also referred a candidate who got the COO role.

Are you asking for advice or for money?

Taking the lead isn’t just about who’s driving next steps. It’s about establishing ground rules for the conversation itself. Are you seeking advice or money? Mentees can get confused and waste time if they think they’re on a path to raising money when the mentor is there to get to know them and to give advice.

Some find that money is a touchy topic, but it doesn’t have to be. I’m not advocating that in the first five minutes, the mentee says, “When are you going to write a check?” But if things stall, and are having multiple meetings that lead nowhere, maybe it’s because your goal is funding and you haven’t made that clear. Don’t assume that just because you’re talking to an investor, she is considering writing a check or even knows you want one. Be explicit.

It’s also okay for mentors to say no, whether you’re asking for guidance or cash. That’s good preparation for what will happen when you pitch to potential funders or customers, where you’ll likely get more no’s than yes’s. 

The power dynamic is inescapable

Many mentees wonder what they have to offer a mentor. It turns out to be a lot, including the opportunity for mentors to learn about new companies, apply their knowledge and experience, reengage with early-stage work, and, if the mentor ultimately decides to invest, the chance of a financial return. As one founder said, “I have to remind myself that I’m providing an opportunity, I’m not a supplicant.”

Founders may know intellectually that they and their mentors are equals, but most struggle to believe it. Here’s what you can do about that:

  • Ask the mentor what she wants out of the interaction and check in along the way to find out how she thinks it’s going.
  • Show that you’re open to feedback, but that you also have your own agenda and views. It’s fine to disagree.
  • Remember that mentors are just people. Do your homework to find out about their backgrounds and interests. Make clear that you’re not coming to them just because of their title or because they’re an investor, but because there’s something in their personal story you want to learn from.

These steps can go a long way toward shifting the power dynamic.

The imbalance isn’t just about funding. One mentor I worked with doubted a founder’s commitment because, in addition to working on her startup, she had a full-time job. Founders, the mentor said, should focus all their time on their companies. That’s fine for someone with savings or family money. But most don’t have that luxury when they’re running a pre-revenue business.

Mentors are important. Good relationships with mentors don’t just happen. You need to invest time and effort to create them. But you’ll get the support you need if you approach them knowing what you want, making specific asks, and driving the interaction.

Lisa Frusztajer Headshot 1 1 Lisa Frusztajer

About the author

Lisa Frusztajer spent most of her career in technology, contributing to building products and organizations. Frusztajer is a certified coach who works with female founders and executives to help them become effective leaders. She advocates for a more equitable distribution of capital and opportunity.

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