I recently found out I was a finalist for Mentor of the Year for the Moxie Awards, a big Chicago tech event hosted by Built in Chicago. It’s an honor to say the least, having my name alongside the founders of companies like Jellyvision and Opentable.
It also can serve as a case study for anyone looking to increase their influence in their respective communities or become a mentor themselves.
Perhaps you think you’re too young, or that you haven’t accomplished enough in your life. Perhaps you fear that you’d say something stupid, and the person or people you’re talking to would think you’re an idiot.
Join the club.
4 years ago I didn’t really know many people, much less advise them. I felt many of the things you might be thinking now.
Today I’m a professor of marketing at Northwestern and have at least a small reputation in Chicago as someone to talk to about product strategy and digital marketing.
That transition had a lot to do with dumb luck. But it also had a lot to do with good people helping me realize I have something useful to offer, and a lot to do with certain activities I engaged in once I made the decision to become useful to others.
Below is an attempt to outline how that happened. Hopefully there’s something in the story that will prove helpful to you.
Have a Good Mentor Yourself
The first key to becoming a useful mentor is to have one already. A good mentor shows you how to be a good mentor.
A good mentor will tell you the truth about yourself (good and bad), will have already done what you want to do yourself, and will encourage you to stretch and grow.
I’ve had many in my life, the most recent of which has been my partner Joe Dwyer. I got to know him when he was the CEO of a startup where I led product, and the relationship grew from there.
At the time I would have laughed at the idea of being a mentor. Even though I had been a part of a successful exit as the creative director of a higher ed marketing company and was managing product development in this new role, I didn’t consider myself someone who had any useful advice to offer.
I also had a huge fear of putting myself out there, worried I’d be exposed as an impostor who didn’t really know what he was doing.
Joe was the guy who pushed me out the door. He was able to help me see beyond my insecurities, and realize that there was plenty I could offer others.
I also was able to watch him model what a mentor looked like, both in working with me and with various founders around town. I was able to see how he listened, how he asked questions, how he challenged, how he built up. In many ways my nomination is a nomination for him, since he was the catalyst for all of it in the first place.
Finding someone to be your mentor isn’t easy – they have to know who you are, what makes you tick, and enjoy being around you to commit to something more involved. But finding someone who wants to get coffee isn’t. You’d be surprised how willing folks are to help out as long as you’re friendly, respect their time, and are specific about what you want help with. Some suggestions:
- Have a warm introduction – makes a huge difference if someone they trust recommends meeting with you.
- Don’t fake the introduction – don’t reach out to someone 2 degrees away pretending your mutual connection introduced you. You’d be surprised.
- Be specific about what you’d like advice with. They might not be the most equipped to help you, and you won’t waste their time. They also might suggest someone more appropriate and facilitate the introduction.
- Be flexible about time, and meet close to them. Make it easy for them.
- Respect their time once you’re there – if you say 20 minutes, make it 20 minutes.
- Plan your questions in advance. Demonstrate clarity of thought and a willingness to get to the point.
- You don’t always need to meet. I’ve developed plenty of relationships with people simply over email. If you have a very specific question, ask the question and save the meeting. Do this a few times over a year and when the time comes when a meeting is warranted the likelihood goes way up.
- Always ask if there’s anyone else you should talk to to grease the wheels for future introductions.
- Always thank them. Ideally with a paper card. No one sends them anymore, and it’s memorable. You can use a service like MailLift to automate this.
- Keep a personal CRM of some kind – can be as simple as Evernote for note taking and a calendar reminder to follow up, or you can use more advanced tools like Contactually.
As you’re meeting with people, pay attention to how they listen, what kinds of questions they ask, how they respond to you, when they offer advice, etc.
A true mentor-mentee relationship often can grow organically by simply following the process above. You’ll develop relationships that have a huge impact on your life and career, and learn how to become a useful mentor yourself.
How to be useful
In order to be truly useful to someone in a mentorship capacity, you have to provide something they don’t already have.
Experience is the obvious one. The reason most mentors are older is simply because they’ve been around the block and have experienced many of the things their mentees are going through.
The more projects you’ve worked on, the more at-bats you get, the more you learn and the more useful you are. One more reason why working for free can be advantageous early in your career.
My time in New York was unusual in that my team was responsible for designing over 300 sites per year. It was an insane pace, one that led to the creation of some bad habits (like conflating the sketching, wireframing and visual design steps into a single sprint in Photoshop).
What it gave me though was over 1500 projects, 1500 sets of deadlines, 1500 creative briefs and 1500 presentations to clients. Simply put, I got more at-bats on real projects with real constraints in a compressed timeframe than most people get to do.
But experience isn’t the only resource you can provide. While not everyone has an opportunity to work on real projects, everyone can learn from them. Millions of projects, and more importantly the experience gained from them, are available at your local Barnes & Noble for twenty bucks.
Books are a huge force multiplier. Like hundreds of portable mentors, waiting to share their wisdom to anyone willing to turn off Game of Thrones and open them.
So much of what I’ve done in my career was in response to a book by someone way smarter than me. You can save thousands of dollars and months of your life grabbing every book you can about a topic and devouring it in a month vs. trying to learn just by doing.
My buddy Emerson Spartz has a story about wanting to learn negotiation skills. He read every book he could find. He took tons of notes. He consolidated those notes into a single page framework of the best ideas and tactics. He set himself reminders to review the material – one day later, one week, one month, every six months. He crafted thought exercises to “practice” the material in his head, working through different scenarios and effectively negotiating with himself.
Most people I tell that story to think it sounds crazy or elaborate. But when they find out what Emerson has managed to accomplish in his young life, and when they find out that he directly attributes that training to millions of dollars in successful negotiations, their ears perk up.
Emerson could have been an amazing mentor on negotiation (or dozens of other topics – he’s truly a polymath) simply from the process he went through to learn. The actual experiences certainly enrich that knowledge, but he probably knew more than 99% of the population simply from the study.
There’s plenty of value even in things you don’t get a chance to implement. Students in my class love the stories of how Uber or Dropbox or Udemy or Paypal grew more than the stories from my small successes. For my students, those stories aren’t a crutch to make up for my lack of experience – they’re why they take the course. If I only drew from my own experiences, the value I could provide would be considerably less. The same will be true for you.
Read a book a week starting today, for the rest of your life. Implement what you can. Take great notes regardless. Review them regularly. Here’s 52 of my favorites to get you started.
Do it for the right reasons
Seth Godin talks often about the power of gifts – that giving someone something valuable is immensely powerful.
I’m not a great artist, or musician. I’m not super funny. I’m not a particularly gifted writer. And I’m not a billionaire.
But I’ve found a gift I can give, one conversation at a time.
The thing about a gift though is that you don’t expect to get paid back. Otherwise it ceases to be a gift – it becomes a transaction.
I have no agenda with mentoring. Occasionally a meeting turns into something more – one of my favorite hires started over coffee, and a few clients began that way as well. But 99% of the time we just stay in touch and I get the joy of watching them succeed and trying to cheer them on.
Don’t get me wrong – there are plenty of great things that can happen. The Kellogg gig never would have happened otherwise, and obviously the award nomination wouldn’t have either. But none of that was expected, and certainly wasn’t the motive. Those kinds of opportunities are very rare, often happen years later, and come from very unexpected places.
If you don’t enjoy simply listening to other people’s stories and sharing ideas with them, without fanfare or any expectation of being paid back, you’ll be sorely disappointed and quit before any of those amazing opportunities appear.
Just Get Started
You’re ready to be a mentor to someone.
Maybe you just graduated college. You can mentor people navigating college life.
Maybe you’re 4 years into your career. You can mentor people who are just getting started.
Maybe you’re a founder who succeeded. Maybe you’re a founder who failed. Either way, you can be valuable to someone.
Regardless of the season of life you find yourself in, you have the ability to built into other’s lives. And the gratification it can bring you is tough to beat.
Start looking for a mentor of your own so you can learn how to be a good one. Start looking for ways to get more experience more quickly. Start reading everything you can, whenever you can. Start going to coffee with people.
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