Is Mentorship Like a Game of Chess?

Today our Batch 8 startups will begin to meet with mentors, a process that will take around a month. They’ll have nearly 100 45 minute meetings with mentors from diverse industries and specialized backgrounds.

So how do we prepare startup founders for getting the most out of this crazy rush of meetings? Simple: we give them tools, and training on how to use them. Pro tip: start with David Cohen’s Mentorship Manifesto.

The First Best Tool: Positioning

The thing we focus on first with our startups is “Product Positioning,” which we’ve also written about extensively on the blog. In short, it’s the art of framing your work in a context that others will immediately understand, accept, and sympathize with. A position statement details the target customer, what their problem is, how you solve their problem, what their alternatives are (your competition), and how you’re different.

We strongly believe that starting mentorship sessions with a positioning statement is key to getting the maximum possible value out of mentors. It sets the ground rules for a conversation at the outset: helping a mentor to understand what your basic assumptions are about the world and what you’re doing, and letting them know what you’re working on, and what you know about the business you’re in.

Mentorship as Chess

Mentorship can be thought of as like a game of chess. There are two players, they are equally matched, but one must move first. Both know the rules, but neither understands the thinking or tendencies of another before the game begins. The game is limited to the pieces on the board. Slowly, by making their moves, the two players reveal to each other what is important to them. Every move has an answer, and you don’t stop until one of you is out of moves (or time is up).

Of course, mentorship isn’t a competition, but then in some ways, neither is chess. It’s an exercise in controlled, directed communication. That is what good mentorship is: a focused, stripped down form of conversation that teaches two people about each other.

In this light, mentorship can be seen as a process you can optimize and perfect. You can get better at it over time.

Here are some steps to do that:

Step 1: Setting the Board


Rather than sit down across a table from a mentor with nothing to say, and no plan for how the conversation should play out, the founder must “set the table,” often with a pitch, or a positioning statement.

Setting the conversational agenda is a vital step, and there are many ways of screwing it up. One of the ways founders fail at setting the agenda is by refusing to lead. Rather than come out and state what they do, and what they want to talk about, they will bite around the edges. They will delay, and distract, rather than getting to the point.

And this happens because of fear: fear of failure, or of looking stupid. That fear leads founders to try and push the focus of the conversation away from themselves. Sometimes they try to start with “literature” such as an executive summary or a pitch deck or video, as a way of easing the pressure on themselves. But this is usually a mistake, because the opening of a conversation is about “setting the board,” and bringing a mentor’s attention to the topic you want to discuss. While a pitch deck or a video might be interesting, but it’s also impersonal. It isn’t you. This would be sort of like inviting someone to play chess, and then asking them to critique your outfit. You are a living mind, not a pitch deck.

If the first thing you show someone is a presentation, then more often than not, the whole conversation becomes *about* the presentation, or video, or whatever it is. Rather than engaging with ideas, a mentor reacts to things they are shown: they react to what they see, rather than what they are asked to imagine. This limits the conversation, and usually wastes time and energy.

Like in chess, getting the focus of the other player to the center of the board (and away from your side of the board), is critical to controlling the game. If you start out offering your work to a mentor for a critique, then the rest of the “game” is played on your side of the board. This is how mentoring sessions turn defensive and counterproductive.

Step 2: Following a Strategy


As conversations have many layers, so too does chess. There are tactics, such as using combinations of pieces or positions on the board to accomplish tasks, and there is strategy- the way you pursue your overall goals by using certain tactics instead of others. Just as in a conversation, the tactics you use are superficial: a certain combination of words or a way of speaking. Jokes are a conversational tactic. So is eye contact. But these are not strategy.

Often we confuse tactics for strategy. We talk about the superficial aspects of conversation: how to talk to people, and how to please them. But ingratiating yourself is one thing, and getting what you need from a mentor is something else.

Your strategy is more premeditated, and it requires planning. How will I win this person to my way of thinking? How will I talk to them in a way they will understand and sympathize this? We do not achieve very effective conversations by relying on charm and wit alone – those are only tactical elements. Really good mentoring only happens when the founder plans ahead, thinking carefully about what they want from the mentor, and about how they are likely to get it.

Having a good strategy means gathering intelligence about the mentor you’re talking to, having an outcome for your conversation in mind (the thing you want the mentor to give you or do for you), and understanding what it is the mentor wants from you. Why are they mentoring you? What do they stand to gain from you?

All these questions can be asked before hand, but often are not. Some founders never engage in a clear strategy, and so they simply chat with mentors, never really getting anywhere. They try to be liked, rather than to earn respect and attention. Don’t make that mistake: having a “nice” conversation, and really getting something out of a mentorship session are not the same thing.

Step 3: The Endgame


Chess also has an end. Or rather, it reaches a point at which there is nowhere to go. That is the nature of the game, and to some degree, it is also the nature of a productive mentorship session. Knowing when you should stop is as important as knowing how to start. But often founders begin to repeat themselves, or to delay the end of the interaction, either to try and make a good impression, or just because they don’t know how to cut themselves off.

Sometimes too, mentors like to talk. I am guilty of that as a mentor, and I rarely end a conversation myself. If the person I’m talking to is very interesting, then I don’t always want to end it. But then that is about what I want as a mentor, not about what the founder needs. Thus, I do notice when founders are unable to break away and close the discussion. If the conversation takes on an air of inevitability, then don’t drag it out. Don’t get repetitive.

By having clear goals in advance, you’ll be more able to decide when and if those goals have been achieved, at which point you can conclude the conversation, and move on to other things.

As in starting a conversation, there are tactics for ending them. For example, you can shift gears by summing up your talk, and then clarifying the next step both parties are going to take. You can also frame this as a kind of question: “So, we’ve talked about the challenges in selling my product, and you’ve given me some great advice. Now I’m going to be implementing that advice, and I’ll let you know the results about 2 weeks from now. As you mentioned, you’re going to connect me with your contact at company XYZ. Shall I email you a reminder tomorrow morning?”

Then it is only for the mentor to either add something, or agree with the summary and plan. The conversation has been effectively closed, or pushed nearer to finishing.

Know too, the signs of a mentor who is done talking to you. If they begin to summarize your meeting before you do, follow along, and either confirm what they say, or add what you need them to remember. Always agree on what happens next, even if what happens next is “I’ll see you around.” You won’t need to follow up with every mentor, but make a habit of stating what your intention is. If it is not to stay in contact, don’t tell them you will. If you plan to contact them soon, then tell them this too.