Great business mentors are one of the most valuable assets a startup Founder can have. They can shave years off of your startup journey simply by avoiding costly newbie mistakes. They can make life changing introductions to investors, customers and key executives. They can accelerate your ability to grow your startup by orders of magnitude.
But they can’t do any of that unless you know exactly how to use them.
On it’s surface, it sounds easy enough – find someone who seems to be an expert and ask them lots of questions. Yet if you’ve ever sat in the business mentor seat as I and thousands of others have done, you know that the value you get is directly tied to exactly how you manage the mentor relationship.
If you have a business mentor, or even if you are a mentor, I’d love for you to read this through. Even if you skip to the examples or key questions – that’s OK. What’s important is that more Founders are engaging their mentors in a structured way that requires less time, less friction, and more outcomes.
If you’re going to take up your mentor’s valuable time, stating your purpose early on is critical.
Imagine you had a chance to meet Albert Einstein in the flesh. Or perhaps artificially intelligent, virtual reality Einstein. Either way, let’s say you could get a mentor session with Al for 30 minutes. Here he is, one of the foremost geniuses in history and he’s all yours.
What would you ask him?
Let me tell you what you probably shouldn’t do. You shouldn’t bullshit with him for 15 minutes with senseless small talk, pose some amorphous questions that may or may not relate to your concerns, and in the end thank him for his time.
Instead, you should be very specific about what you want to get out of those 30 minutes. It starts from the moment you set up the meeting.
You need to state your purpose clearly. Don’t by shy.
“Al, I need to spend 30 minutes with you to understand the consequences of breaking the Theory of Relativity.”
In all fairness, it may go past 30 minutes. But the point isn’t the time block, it’s setting Al up to know exactly what you’re trying to achieve. Make the outcome and focus extremely clear so that both of you know—going in—what you’re looking to get out of it.
A few interesting things happen when you’re clear about your purpose. First, it may just so happen that your mentor can respond with “I don’t know the answer but my friend does,” which saves both of you a bunch of valuable time.
Second, it gives the mentor some time to noodle on the question ahead of time. Think about it—when is the last time you had a better answer being put on the spot versus being given time to prepare for the question? Never. Your mentor is no different. If she knows what the outcome is before going into the meeting she can prepare properly, which gives both of you a much better outcome.
Lastly, stating your purpose keeps the conversation on track. When neither party knows what you’re really aiming for, it’s really hard to get two people aligned in a short period of time. A clear purpose lets everyone get a running start.
Once you’ve set the purpose of the meeting, you then need to prepare what your “asks” are going to be.
Your asks are the requests you make of the mentor. These are most often specific questions you need answers to, a request for them to help you in some way or introductions you’d like them to make. Maybe all three.
If you take all of five minutes to brainstorm these and write them down, you’ll buy yourself a much better outcome with your mentor. Also, you don’t need to hide these questions like some game show host with the answer to the contestant’s challenge. They aren’t a secret. Share them with your mentor ahead of time, so once again she can prepare properly.
Often times the asks come as a result of the meeting. You know that you are working toward a business development strategy but it’s not until the mentor provides more color around whom you should target that you know what introductions she could make for you.
In that case just be prepared for the follow-on questions at a high level. If you know the stated purpose is to “determine our business development strategy” then just write out a few bullet points to remind you to drive the conversation properly.
Your notes should look something like this:
Purpose: Determine our BD Strategy
Q1: What’s the most efficient path toward landing our first customers?
Q2: Can you (mentor) help us define the profile of our ideal customer?
Q3: Would you introduce us to someone who would fit that profile?
With just three questions around the purpose you’re honing in on asks around the mentor’s expertise and introductions. By providing an overview of specific questions, you can make sure the conversation stays on task and you’ll be better prepared to ask for specific requests that can drive your startup forward.
One of the most common takeaways from a business mentor meetup is the request for an introduction to someone—an investor, customer, partner or job candidate.
I’ve seen this request for an intro go wrong pretty much 99% of the time. The reason is because the person requesting the intro often doesn’t understand how introductions should be made properly.
To understand how to properly ask for an introduction, you need to first understand what an awful intro request looks like:
“Hey Wil, was great meeting with you today. You mentioned you know the Super Mario Brothers. Would love to meet Mario and Luigi.”
The request itself is clear—you want to meet Nintendo’s most famous plumbers. The problem is that you’ve overlooked three critical questions:
Let’s unpack all three, because this is an important topic.
Often introductions are lopsided transactions. You want to meet someone who has a lot of value (an investor perhaps) but you may not have a lot of value yourself. If you can’t provide a compelling reason for them to meet with you, why would you expect your mentor to make that introduction? It’s up to you to build a business case for why the meeting is important to them.
Here’s an example:
“We’d love to meet up with Mario to discuss the challenges he’s having in the later levels of Super Mario Brothers and how the solution we’ve developed to vanquish Koopa Troopas could be really valuable.”
Now we’re talking. Those blasted Koopa Troopas are a huge PITA for Mario and Luigi, so if they hear of a new method for avoiding their threat, that’s a compelling reason to meet up.
Let’s just short cut this explanation now—no one cares about your term paper length business mission but you.
What you need in this case are two sentences that nail the value of your business specifically to the person reading that email. The purpose is to make it compelling to them specifically, so this isn’t a cut/paste job from your “About Us” page.
Here’s an example:
“At TurboTime we’ve developed a solution to allow 8-bit plumbers in platform games to run three times faster, creating longer jumps across treacherous canyons and easily avoiding deadly villains.”
Think about how Mario and Luigi are reading this. When they get this intro they are thinking “Awesome! I would love to run faster and not get pummeled by bad guys.” That’s it. Focus on their lives, their problems and tailor your description accordingly. Less is more.
I could write an entire essay on social capital, but instead I’ll give you the TL;DR version. All of a mentor’s relationships are based on history and trust, built on the reputation of the mentor. An introduction is like letting you borrow a mentor’s reputation or “social capital.”
If I worked really hard to meet the head of a major venture capital firm, and I’m going to send him two emails per year to make introductions, they better be the most valuable introductions I can possibly make.
The moment I send a low-value introduction just because someone asked me to, my social capital with that individual goes down. If I send two in a row, it may go to zero. I lose that relationship and can’t use it anymore because I abused and spent my social capital.
You gain social capital by providing value to others. You lose it by taking it away. It’s that simple.
With that in mind, you really have to ask yourself, “will this ask likely add or reduce the social capital of the mentor?” You can add value if you do a really good job thinking about the answers to the first two questions.
The more you can do to make the mentor look like a hero, the more likely you are to get that introduction.
I have a general rule that after a meeting with a startup I’m mentoring I never send the first follow-up. It’s not because I’m 22 years old and I’m waiting to see if the girl texts me before I text her.
I’m doing it because—if you can believe it—many people never follow up. And if you’re not going to follow up then why would I spend time doing your bidding?
If you’re going to invest all of the time to set up a meeting and draw value from your business mentors, it seems obvious to me that you’d spend as much time with a follow-up to advance the conversation.
The best time to send a follow-up is within an hour of the meeting being completed. Don’t worry about “looking too desperate.” Again, this isn’t a post-Tinder moment. I think about it in terms of “I like to get shit done,” and I personally love it when other Founders feel the same.
The follow-up should be short and highly specific (you see a theme forming here?).
“Wil, it was great meeting with you today to go over our business development strategy. I liked your thought about focusing on up-and-coming heroes in platform-based side-scrolling games. If you have some time I’d really appreciate your help on:
Remember that the shorter this email is, the more likely you’ll get a response. Every sentence you add creates more friction for the mentor, which means less chance you’ll get what you’re asking for.
Beyond the meeting and follow-up, it’s great to keep your business mentors apprised of your progress. Once again, there are better and worse ways to do this.
The best updates are short, punchy and sometimes include a specific ask of the specific recipient.
The worst updates are long, amorphous and make general asks to a weird BCC list of recipients.
Updates are generally a good thing. Mass-marketed updates that look like they are going to a mailing list are generally a bad thing unless everyone needs exactly that intel.
Your mentors are always looking for ways to help, so don’t waste your cycles with them sending generic updates.
“Hey Wil, I wanted to let you know about three wins we’ve had since we last spoke and ask you for one specific favor.
1. We just landed the Sega Genesis account which will 3x our business.
2. We’ve added Zelda to our Board who has helped us get intros to a host of important heroes.
3. We just released a new feature we called “UP, UP, DOWN, DOWN, LEFT, RIGHT, LEFT, RIGHT, B, A, START” that will allow for 30 extra lives in certain games.
On point number 3, would you be able to introduce us to the guys over at the game “Contra?” I think they would be super interested in the 30 life extension.”
Instead of wasting your updates with self aggrandizing updates no one cares about, think of them as another way to extract specific value from people who genuinely want to help you.
When it comes to getting 10x more out of your business mentors, less is more. You want to focus substantially more effort at fewer asks. It’s not about asking as many questions as possible, it’s about asking the most important questions and giving your mentor the best ability to do something to help you.
If you can stick closely to this mantra you’ll find yourself spending less time making requests and more time benefiting from those asks!
Wil Schroter is the Founder + CEO @ Startups.com, a startup platform that includes Bizplan, Clarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.