Be The Mentor You Wish You’d Had

(alice mollon/Getty Images)

This past Fall, l I took a leap of faith in myself and my career to attend the Chairman Mom Flee ( I joined a retreat for 100 women (mostly moms) and found myself inspired while surrounded by other women like me: all type-A investors, founders, and CEOs. I, like so many others, stressed about whether or not I even deserve to be there — imposter syndrome is real, ladies. Add to that the fear of mean-girls, posturing, and mom guilt…the doubt and anxiety are enough to make anyone take pause. But I took a breath, booked the flight and off I went. I learned so much about myself and the struggles we women face each day. I wanted to share two transformational takeaways from the retreat.

  1. Connection vs. Transaction (and both are ok!)

The second night of the Flee a conversation with a small group started over a bottle (or three) of wine at dinner, personal stories were flowing and past interactions were fair game. One woman shared a story about a time in her career when she was asked to edit a book of another high-powered woman. This is where the story could end, transactionally. Instead, my friend realized she was being lured into a feeling of connection that wasn’t real. Once the project was over, the “connection” abruptly ended. No phone calls, no invites. She realized the whole thing was inauthentic. She would have done the work if simply asked — transactionally. The work and the acknowledgment were great, but the connection was fake. And it felt awful.

When creating our tribe, we should look for a connection with those who are not only different than us but also that there may be those at other stages in life than us. This can include people we may not even agree with. Allowing room for these connections allows us to be lifted and possibly at the same time lift up. To see another woman and celebrating her accomplishments doesn’t lessen our own accomplishments. And it shouldn’t lessen our self-confidence.

There is nothing wrong with being transactional at times. The key to a successful transactional relationship is that it’s based on honesty. When done right, this transaction serves both women well. But, when women take sisterhood and use it as a weapon, it does harm to the whole idea itself. It’s an ugly experience and even worse feeling when you feel taken advantage of. We owe it to each other to be a safe, trusting space.

Several weeks later, it came up again with a group discussion about mentors. A woman shared she has been looking for a mentor, but was discouraged after reading an article that said, “Don’t ask someone directly to be a mentor. Let it happen organically.“ What does that even mean?

Why as women is it frowned upon to just ask?

The beauty of the Flee was that women were offering and asking for mentorship. It wasn’t something to shy away from and there was no pressure to fake connection. I read a tweet quoting Arlan Hamilton (Arlan), where she said, “Share your privilege. Everyone we know has a privilege, if all work together and share that, things can definitely change for the better.” And it’s true. We are better when we lean into each other, lift each other up, and band together.

It’s not pie, where more for you is less for me.

Being transactional doesn’t lessen our connections. In reality, it could enhance your connections and the depth of your relationships. Being direct and honest with intention while still connecting personally is where you can gain the most value. The opportunity to be transparent could lead to that deeper connection. I’m not suggesting that with every connection you will find that “ride or die” friend, but you never know! Connection and transaction don’t have to be either/or.

2. Access

It took a trip to a secluded town of only women to realize my own need for access to other strong women. Women at other stages in their career. Access is powerful when given and access allows for that potential of connection. You can’t have one without the other. We need to set boundaries of course, but we also need to be more accessible. Think about this while you are posting on social media, available during office hours or simply attending more career-focused events. I used to find networking incredibly draining but I realized those events could also be about finding connection with other women at different stages.

For me, when starting a business or taking on a new project, I need access to women who have been there before. Call it a mentor or call it a support system, having access to women who were dealing with similar struggles is powerful. We’re all aware of the statistics highlighting the need for more diversity and more women in leadership roles in business. For example, First Round Capital took a look at 300 of its portfolio companies and almost 600 founders and found that the teams with at least one female founder did 63% better than the all-male founder teams when looking at how much the company values have changed since the firm’s invested in them. And Women-led companies had higher returns than the S&P 500. Yet, only 4.8% of CEOs at Fortune 500 companies are women; and that is down from 6.4% in 2017.

If we have any shot of that seat at the table, a higher role, or chasing our dreams, we must not rely on the majority (that is, men) to take the lead on this opportunity. For women, we need to consider mentorship as an “all hands on deck” situation and help out however we can.

I learned a tremendous amount from the women I encountered on this short journey. Not just from workshops and soundbites, but from observing what can happen when women find a safe space and the layers of “stuff” disappear. What could have easily been transaction became an actual connection.

So, Ignore the fear of Queen Bees. Dive head first for the chance to find connection and a hand at your back pushing towards something great. Here is your homework for today:

  1. If you haven’t found that connection yet, or settled in with a tribe — Connect with me on Twitter. I love interacting with brilliant minds and sharing stories @jillianbwalker. Never underestimate the power of your Twitter-ships.
  2. Write about your imposter syndrome. Fear, as you may know, is a liar. The best way to overcome your fears is to dive into them. Share your reflections with a friend or mentor.
  3. Speaking of mentors, ask someone you admire out to coffee. Ask for their advice on a work or personal project. Don’t worry about forcing the relationship or concept of a mentor — just make the ask (transaction) and see how your relationship evolves (connection). Sometimes, the best relationships form when we have an open mind and no strict guidelines to build upon.