Want to turn a role model into a mentor? Just be cool

This is the second part of my series on mentorship, which I started a few months ago here with the post, “Want a mentor? Stop asking for one.”

A few months ago, I wrote about how the kiss of death when it comes to seeking out adult mentorship in your life is often the very act of asking for a mentor. Furthermore, I pointed out (and still really believe) that this misconception around mentorship is all a bit over-played. At the end of the day, most of us don’t need someone to meet with us every couple of weeks and guide our every action in our careers. Chances are, you’re just looking for some good advice now — and maybe again in a few months.

There are a lot of tactics I shared about how you can go about securing an initial coffee meeting or phone call with someone you’d like to learn from. In this post, I’d like to talk about something much more nuanced — how to stay connected with that person over time without being a creep about it.

This is how my cat meets new people:

1. New person walks into the house. Cat gets intrigued, comes to the door. New person finds this cute.

2. New person sits on couch. Cat approaches slowly, starts smelling their shoes. Maybe rubs her face on their shoes. New person finds this adorable. They feel flattered and loved. They put out their hand to say, “Here, here, kitty.” Cat is overjoyed.

3. Cat jumps on lap of new person and aggressively rubs her face against their face until they develop a cat allergy. Cat rolls over on their lap so much that they have accumulated enough cat hair on their pants to fill up a vacuum cleaner. And, worst of all, if this guest is spending the night, cat forces herself on their face all night long until they simply grow tired of pushing her aside. They barely get any sleep. In the end, war-torn and weary, our friends leave saying something like, “Well, your cat is cute. But DAMN is she an aggressive cuddler.” They don’t ask to stay here again.

She’s doing it wrong, of course. I’ve tried to tell her. You can’t go from meeting a new person to “best cat-human friends forever” in a matter of 30 seconds. And no matter how much someone loves cats and cuddles, it’s likely still not enough for them to be willing to forfeit a good night of sleep just so you can sleep on their face.

This is the same problem I see among humans who are looking for mentors. Let’s be real: Nobody goes from one coffee date to full-on mentorship overnight.

Even if you think you had the best, most amazing conversation — even if you both bonded over multiple relatable personal matters or happened to be from the very same small town when you grew up — even if they leave the meeting and say to you, “I had a really great time, let’s do this again.” — that still doesn’t give you permission to act like my cat.

I once had someone who, after meeting me once at a networking event, sent me a page-long email one week later proclaiming how “lucky” I was that she selected me to be one of her top 10 “life mentors.” I’ve chosen you, she wrote, because I think you can help me on my path more than anyone else. All I’m asking is for you to review my annual goals with me, meet up every month or so, and hold me accountable for career goals that I’m pursuing. Please reply back with your availability this month so we can schedule our first session together. Won’t this be fun??

That was the closest I’ve ever come to throwing my computer across the room.

Please don’t do that. When it comes to developing long-term relationships with people you admire, it’s imperative that you’re cool about it. Here are a few tricks you might try.

This is probably the easiest way to stay connected with someone over time. If you had a great conversation about engineering tools that your team uses, for instance, the next time you try out a new tool that you love — whether it’s 1–3 months later — drop them a quick line. “Hey, I just wanted to let you know that I’ve been using Code Climate with my engineering team for the last few weeks, and it really seems to be helping with transparency and internal velocity. Just wanted to pass along the link in case you’re interested to check it out, too. Hope all is well!”

Here’s the best part about writing a note like this: There’s no response required from them. You’re not asking for anything. You’re not trying to sell them something. You’re just passing along a helpful tidbit that you thought they might enjoy.

Crossing the Line: Please don’t do this every week. You’ll quickly blow right through the perception of “periodically helpful” and move into “downright annoying” before you know it. Use your best judgment here. Ask the question: “How much would I want a new person to email me?” Use that as your guideline.

It’s not quite as common, but if you happen to discover in your first coffee meeting that your wannabe-mentor has a current painpoint in their life that you might be able to help with, by all means, dive right in! Keep in mind that because this person is probably more senior than you, it’s not always likely that they’ll come right out and share what’s bugging them or stressing them out. So listen for clues. Here a some to be on the lookout for:

• You hear: “We’re growing the headcount a ton this year, so my schedule has been a little crazy.”
   You might offer: “What roles are you looking for? I wonder if any of my friends / colleagues would be a good fit.”

• You hear: “I’ve been doing a lot of research for my new book on organizational design.”
   You might offer: “Oh! You probably read this already, but did you see that great piece in the last Harvard Business Review article about how conducting company-wide reorgs elicits a similar feeling as when people clean up their homes, Marie Kondo style?”

• You hear: “We’re gearing up for a family trip to Tokyo this fall.”
   You might offer: “Oh yeah? I visited the best ramen place in the world when I was there. Do you like ramen? I’ll email you the info.”

What’s great about these examples is that they are all very small, specific instances where you can demonstrate small added value and also find a reason to keep the conversation going after you both walk out of the coffee shop.

Crossing the Line: Don’t fish for ways to show off just to find a reason to send a follow-up email. Chances are, this person you’re interacting with is smart enough to figure out when you’re just fishing. I’m not suggesting that you jump in as the “rescue ranger” for every single one of their own issues. This option is best used only in unique circumstances where you might actually have something valuable to contribute. If not, then you’re better off skipping it.

This is probably my favorite trick in the book. If I meet someone really great, I’ll rack my brain during our early meetings and try to find an excuse for us to work together in some way — any way. Of course, this requires some quick thinking and a clear mutual benefit or opportunity to be gained on both sides. It also requires the most work on your part. But if you get this right, you not only have a potentially fun partnership opportunity but also a fantastic personal learning and growth experience to look forward to.

Here are a few examples of partnerships or projects I’ve established recently:

• Teaming up with a great management training company to co-design a program for new managers across the USV Network

• Subscribing to a new piece of software and having periodic calls sharing feedback and product roadmap updates with each other

• Inviting someone super senior in their domain area to speak at an event we hosted for companies in our portfolio network

These are all external examples, which can be great if you can pull it off, but I’m also in a lucky position in that I have resources at my disposal — like, a network of people in startups, a space to host an event, and a budget to pay for software. However, I also love to use this trick internally as well. If there’s a team you want to work more closely with, or a person who you’d like to learn from, look for ways to get creative and find a project that they are passionate about where you can add your expertise.

Crossing the Line: You can’t force this stuff. And, keep in mind that the stakes are highest here. So don’t offer your expertise or a partnership unless you’re willing to commit to the work on your end. After all, if you convince someone to partner with you on a project, but then fail to hold your own end of the deal, you’ve potentially burned a bridge rather than strengthened it.

Unfortunately, there’s no magic formula that will help convert a role model figure in your life into a mentor. In fact, there’s an unlimited number of ways that you can poke and prod and nudge the relationship along. These are just three that have worked for me. Maybe they’ll work for you, too. Maybe not.

But before we close, I did want to leave a short life of things to AVOID in continuing relationships with wannabe mentors:

1. Writing overly flattering notes (It’s okay to say something nice, but if you gush too much, you’ll potentially wreck an opportunity for them to see you as a peer)

2. Sending too many emails (There’s an implied statute of limitations when it comes to how often you’re allowed to email a person. And by the way, if they haven’t responded to your last 2–3 emails, you may want to cool your jets.)

3. Asking them to dole out sage life advice in long-winded emails (I’ve made this mistake more than once, but you have to resist the urge to lay out every personal detail via email. Very few people have time to read and respond to a rambling, confused list of questions.)

4. Expecting a regular cadence of meetings (Look to them to help you set the schedule or cadence that makes sense for you. Maybe in reality, it’s once or twice a year that they have time for you on their calendars. Go with this. This is still a win.)

5. Using the word “mentor” in any of your conversations (Seriously. Just… be cool.)

My cat just needs to learn how to be more chill.

Want more? See part one in this series, “Want a mentor? Stop asking for one.”

Originally published at Dry Erase.