The Case For Co-Mentoring

Two entrepreneurs share what they’ve learned from creating a non-traditional mentoring relationship.

The Case For Co-Mentoring
[Photo: Flickr user star5112]

We’ve all heard how important a mentor is to career development, but many of us don’t have the benefit of structured corporate mentorship programs.


But entrepreneurs and freelancers don’t have to manage their career development alone. We’ve developed a practice we call co-mentoring. It’s changed the way we think about our work and careers.

We started with a shared work experience right out of college as associates in a large consulting firm. Eventually, each of our careers moved in a different direction. We maintained occasional but–not regular–contact.

Flash forward 15 years. While we were both in New York, we decided to meet up for a walk in Central Park. It was our first true co-mentoring session.

After three years, we’ve learned that when you take something informal and infuse it with a modest amount of structure and discipline, you create an incredibly powerful tool for professional growth and success. We’ve assembled seven of our most valuable lessons to help you get started and get the most out of the co-mentoring relationship.

1. Ask For Help

During that first walk in the park, Dawn explained that, after time off to have kids, she wanted help from Sara (who had continued to work outside the home): “I’m ready to go back to work but I don’t know where to begin.”


Even though Dawn hadn’t been in regular touch with former colleagues, Sara encouraged her to call them first: “They know you and know your work. But be clear about what you want from them–an introduction, a project, or an answer to a specific question. You don’t want to make it their job to figure out how to best help you.”

2. Establish Accountability

When you know that someone is going to check in with you, the goals, commitments, or tasks you set for yourself feel more real. On each call, we give each other an update on both near and long-term goals. Though every conversation doesn’t have to focus on long-term goals, when you initiate your relationship, take the time to establish an initial baseline for each person’s work life. If you don’t, it’s hard to have quid pro quo.

These exchanges solidify your commitment to your goals and lay the framework for a continuous dialogue. The next time you talk, you’re prepared when your co-mentor asks you how the pitch went or what you’ve done with your Kickstarter idea. Don’t discount the power of external eyes on your work. It’s a huge motivator and keeps you focused towards long-term goals.

3. Keep To A Schedule

Set a schedule and stick to it. This sounds like a simple lesson but it will make or break your co-mentoring relationship. We meet by phone approximately every three weeks at 12 p.m. for 30 minutes. We put an appointment in our calendars and honor that time as a regular work commitment.

If you connect only occasionally or let a check-in drift too long, you’ll require a lengthy catch-up at the start of a meeting and little time for targeted conversation.


4. Find A Secret Keeper

Establish up front that you’ll keep confidential all aspects of each other’s feelings and businesses. The relationship won’t work well if you hold back the good stuff. Someone who is not a relative, friend, or coworker but has a deep understanding of what you do and where you want to go, can help you negotiate a tough deal or financial situation.

A co-mentor knows how much business you have locked into one particular client and can steer you towards your perfect gig. You can be honest with them and, even more, they force you to be honest with yourself.

5. A Sounding Board Is Not A Cheerleader

Your co-mentor is not a cheerleader; critical support and advice are not just dashed reassurances of success. Instead, a co-mentor offers perspective, specific suggestions, and a total kick-in-the-ass when appropriate. If you work outside a company, in whatever capacity, you’ll periodically wonder what it is you do and where you are going. Regular care and attention to “The Brand Called You,” to borrow from Tom Peters, should be a vital part of your professional development.

Co-mentors push each other to try new things. Dawn encouraged Sara to tap her network at Stanford Business School and teach a seminar or workshop. On our next call, Dawn followed up on that idea and gauged Sara’s progress. Similarly, Sara encouraged Dawn to write about her Kickstarter experiences and develop a long-term perspective on her industry.

6. Don’t Choose A Colleague Or Competitor

One reason our relationship works well is we are not competitors. We don’t discount the power of networking; it’s just hard to be honest and not feel competitive with someone in your industry. Further, you can benefit from “the strength of weak ties,” or loose connections to people outside your industry and typical networks. You’ll find new opportunities when you continuously refine your narrative and expand your audience.


Choose a co-mentor who is a peer. Unlike a traditional mentor/mentee relationship, this is a co-mentor experiment. A wide disparity in experience or knowledge between co-mentors won’t feel balanced and will, ultimately, be only mildly successful.

7. Seek Out Complementary Skills And Experiences

When Dawn’s company, IAmElemental, went live on Kickstarter, Sara asked Dawn for the Twitter handle. At that moment, Dawn realized she’d overlooked critical social-media promotion. Sara walked Dawn through a quick Twitter tutorial and within an hour, IAmElemental had amassed followers. In fact, Twitter was a major feeder for the Kickstarter campaign and an important tool in the brand’s growth.

A co-mentor can be the ultimate inside-outsider. Sometimes, as in our Twitter case, a co-mentor makes a last-minute endzone catch. Other times, you reap the benefit of another smart pair of eyes, looking at the same thing as you but in a new way.

When you work outside a traditional organizational structure, you may lose sight of your surroundings and destination. In fact, as digital footprints abound, every individual must own and thoughtfully craft her story. A long-term co-mentor keeps track of your narrative as you do–and helps unravel it when you get tied into knots.

Co-mentors are helpful for people who work independently but, ultimately, they’re valuable to individuals who work in any size corporations. Who can’t benefit from someone who reminds you of your accomplishments and encourages you to face–not turn away from–challenges? You owe it to your career and dedication to invest in a relationship that is defined by you for you.


Sara Gaviser Leslie is a strategic translator and the founder of In Other Words, a Silicon Valley consultancy that provides content strategy for executive communications, fundraising, lead generation, content marketing, and sales enablement. She’s the co-author of the New York Times bestseller, Transform: How Leading Companies Are Winning With Disruptive Social Technology.

Dawn Wells Nadeau co-launched IAmElemental, the first line of female action figures that Time magazine voted one of the 25 best inventions of 2014. She’s currently focused on a line of games that straddle the intersection of on and offline play.