Want to get the Most Out of Mentoring? Don’t be a Pushover

One of the joys of being at the current stage of my career comes from the fact that I’ve amassed a reasonably-sized collection of experiences that seem to be helpful to founders. Sharing those experiences with up-and-coming founders is one of my favorite things to do. Whether it’s in one-on-one meetings with portfolio companies, online sessions with founders across Canada and the UK, through structured programs like Creative Destruction Lab, or as part of university programs, it’s always an honor and a privilege to speak with ambitious entrepreneurs.

But many founders don’t maximize the opportunities presented by mentorship. And a big reason is that they get caught up in the “honor” of speaking with the mentors.

It seems silly, but it’s absolutely true — I certainly did it when I was a founder!

I’m not talking about getting caught up in a mentor’s “celebrity” or fawning over them like a fanboy/girl. I’m referring to the very common scenario in which a founder eagerly comes to a mentorship meeting and the mentor — caught up in “trying to be helpful” — absolutely steamrolls over them and monologues for an hour.

…and the mentee walks away with none of their actual problems solved.

The solution? Don’t be a pushover!

Here are 5 steps to ensuring that you get the most out of mentorship (without being steamrolled by an overzealous mentor):

1. Have an elevator pitch designed for mentors

A standard startup elevator pitch is a precursor to a sales pitch — whether for customers, investors or potential employees. But mentorship is something different. You’re trying to solicit information and advice, not sell them something. As such, if you use your standard elevator pitch to kick off a mentor session, you’re likely to be pulled into the wrong types of conversations and questions.

To get the most out of a mentorship session, kick things off with a purpose-built elevator pitch that gives mentors the context they need about your company while telegraphiing the topics you’d like to discuss:

• Start with a high-level company description

• Provide a summary of the current status (sales, funding, etc.)

• What are the things that are going well?

• What are the things that are challenging?

• What are 1-3 specific topics you would like to focus on?

Here’s an example:

“Acme.ai has created the world’s first AI-driven LEGO brick sorter to help LEGO enthusiasts quickly find the piece they’re looking for from a large inventory of bricks. More than 5 trillion hours each year are wasted by LEGO enthusiasts looking for specific bricks at a cost of $500 billion to the global economy.

In less than 6 months, our team has:

- Built a working prototype that can identify specific LEGO bricks within collections of up to 10,000 pieces

- Signed 20 paid pilots worth $100,000 with some of the world’s leading LEGO clubs

- Built a waiting list of more than 20,000 LEGO enthusiasts

We recently closed a $750K Pre-Seed round, which gives us 18 months of runway.

We feel like we’ve definitely tapped into a latent interest amongst LEGO enthusiasts, which is manifesting in our waiting lists and top-of-funnel engagement. However, we’re struggling with converting the paid pilots into long-term contracts. The pilot users generally like the prototype system and find value in it, but it’s not translating into commercial agreements.

If it’s okay with you, I’d like to spend our time reviewing the feedback and results from our first few pilots and walking you through our sales process, to see what we’re missing.”

2. Come armed with questions

Beyond just a topic of focus for the conversation, come armed with a selection of specific questions that you’d like the mentor’s perspective on. This will demonstrate to the investor that you’ve already given the topic thought, while ensuring you don’t revisit aspects of the topic that you’ve already thought through.

For example:

“Here are some specific things I would like to dig into:

- Why are our pilot companies willing to spend thousands of dollars on a pilot but don’t seem to have budget for a larger agreement?

- The subjective feedback from pilot users seems to be all over the place. It would be really helpful to see if you can discern any patterns that we’re missing.

- Are there any obvious flaws in our pilot process that might be preventing or delaying users from getting to the “a ha!” moment that could lead to a deal?”

3. Don’t be afraid to interrupt

Ever been in a situation where a mentor starts talking and you can’t seem to get a word in edgewise?

It happens all the time. Sometimes, it’s good ol’ fashioned mansplaining. Other times, the well-meaning mentor gets so caught up in the emotion of recounting an experience they previously had that they lose track of time.

Either way, don’t be afraid to interrupt them! It can feel awkward to do so (particularly if the mentor is someone that you look up to), but I promise they won’t be offended. Just charge right in if/when the conversation goes off-track or the short story turns into a novel:

Sorry to interrupt, but given how little time we have left, I’d love to refocus on X.

4. Be honest and vulnerable

This is the hardest one for most founders, particularly if the mentorship opportunity is in a group setting or the mentor is also a potential investor. But the more honest and vulnerable you are with a mentor, the more likely they’ll be able to help you with your real problem.

I can’t tell you how many mentorship sessions I’ve been in where it’s utterly apparent that the founder’s “up-and-to-the-right” narrative of how perfectly everything is going has no basis in reality. The founder spends the entire time trying to convince the mentor(s) how awesome things are, completely missing the opportunity for help.

Don’t do this.

It may be hard to admit when things aren’t going perfectly — especially when so much of your time is spent putting on a brave face for those around you — but that’s exactly why most mentors want to help. We’ve been there. We’ve seen that. We’ve ridden the startup rollercoaster. And we genuinely understand and empathize with what you’re going through.

We want to help…but we can only do so if you’ll let us in.

5. Remember that these are one person’s opinions based on limited information

Remember that no matter how convincing or confident the mentor is, their advice is just that: the advice and opinions of a single person.

It can be tempting to jump right into following the recommendations of a mentor, but it’s essential that you view their advice through the lens of their lived experience (which may or may not be the same as yours).

The best mentors bookend their advice with a disclaimer, but even if they don’t, just add the phrase “in my experience,” “in my opinion,” or “ymmv” (your mileage may vary) to each and every piece of advice.

Check out this post for more thoughts on how to make the most of mentors.