A Tale of 3 “Workdates” with Female Mentors

Kids have playdates, why can't moms have workdates? Here's a brief account of 3 very different meetings with female mentors, and what I learned from each.

You know how we orchestrate all those playdates for our kids to hang out with their friends? To help them create and nurture peer relationships, build social skills, enrich their interpersonal development … all that good stuff?

Well, I decided recently to schedule my own adult version of playdates to help me with my working-mom life/career. You might call them “workdates.” The idea was simply to meet with different women who seemed like great female mentors, role models, or sounding boards for me.

Over the last couple of weeks, I had three workdates with three different women—each highly successful and accomplished in her own right, and willing to spend a little of her time with me. Here’s a brief account of how each workdate played out.

Workdate #1: Coffee with the top female tech exec

Kids have playdates, why can't moms have workdates? Here's a brief account of 3 very different meetings with female mentors, and what I learned from each.

I’d been eagerly anticipating my morning coffee workdate with a woman who’s run a large tech company. Let’s refer to her as “Sheryl.” I had to book the appointment with Sheryl weeks in advance, having been referred by a colleague, so I had plenty of time to think about what I wanted to discuss and ask when I met her.

When the day finally arrived, I left my office with enough time to drive across town, park, grab coffee for us both, and show up at her office on time. (Which is kind of awesome, for me, the chronically late person.)

Her assistant came over to let me know she was held up in another meeting. I could see Sheryl through the glass conference room doors, and waited patiently outside at an open desk.

Thirty minutes passed.

Sheryl didn’t acknowledge my presence, nor did she come out of the room. The feeling was not unlike being stood up by a blind date. I finally told her assistant politely that I had to leave and walked out, dumping Sheryl’s now cold, full cup of coffee into the trash and heading back to where I’d parked my car to drive back to work.

Later that day, Sheryl’s assistant emailed me with three possible timeslots to reschedule. No apology or explanation from Sheryl, though. I decided I had learned all I needed from this first workdate, so rescheduling was unnecessary.

Workdate #2: Lunch with my business-savvy mom friend

Kids have playdates, why can't moms have workdates? Here's a brief account of 3 very different meetings with female mentors, and what I learned from each.

I am lucky to call some really amazing, super-smart women my friends. As you might expect, we don’t get to see each other often enough due to constantly full schedules. My solution? Recurring lunch dates that could be part workdate, part playdate, and part therapy session (when needed).

The first of these new recurring workdates happened to be with a woman I consider to be my most professionally successful friend. I’ll call her “Hillary.” She has the Ivy League MBA, the resume to impress people who wear nice suits to work, and just really has her stuff together.

We met near her office at a casual place with a pretty sophisticated menu (her suggestion). I arrived on time, Hillary came in a minute or two later from a meeting that ran over (she texted me to let me know). As usually happens when we get together, the conversation flowed naturally, and we each shared some recent personal and professional challenges and victories. I left this workdate feeling very grateful to have such an awesome working-mom friend in my life, and later received the most eloquent, uplifting follow-up email from her:

The theme phrase from the girls’ weekend I had a few weeks ago was “doing the best that she can.”

We were all talking about how hard it was—parenting, working, being a wife, taking care of our selves, being a good friend, etc.—and how we all felt like we were failing in one, if not multiple, dimensions. It was interesting because we we ALL felt that way and felt it very strongly. As we talked more about it, we realized a few things:

  • The feeling was universal—even the people who we thought had it perfect had it really tough in some areas of their life and were really struggling
  • The feeling is bullsh**. We are all “doing the best we can” and doing it quite brilliantly. Life is hard and if you show up every day, that IS winning.
  • We need to cut ourselves and each other (the crabby waitress, the surly co-worker, our crazy kid) some SERIOUS slack. Everyone is doing the best they can and, likely, beating themselves up needlessly for not being “better.”

Reflecting on our lunch today, I want to let you know how I think you are doing amazing things—far more than “the best you can.” You are taking incredibly active steps to improve multiple facets of your life, your kids, your husband’s—steps that many people, myself included, won’t take. It was almost funny to hear you say how hard it all is because, yes, of course its hard. You are doing more than showing up each day—you are scheduling multiple doctor appointments, and planning elaborate date nights, and finding babysitters, and getting down on the floor to play Legos, and scheduling recurring lunches with friends, and decluttering your house AND working, paying bills, getting dressed in the morning, etc. That’s hard work. 🙂

Well said, Hillary. And thank you.

Workdate #3: Breakfast with the uber-wise C-Suite mom

This early-morning breakfast workdate strayed from my usual lunch/coffee M.O., but I was willing to make an exception. Sure, it threw off our family routine a bit (I’m the morning school dropper-offer, Hubs is the afternoon picker-upper). But I’d been wanting to meet this older, wiser working mom from the C-suite of a large publicly traded company for ages. (As I later learned, she prefers breakfast meetings because she can really be present before the day gets away from her. I can dig it.)

“Nancy” has spent her entire adult life working, learning, and developing a remarkable career. Along the way, she raised three kids with her husband, who chose to stayed home with the kids way before being a “stay-at-home dad” was a thing. Now, Nancy’s at the top of her game, an executive who runs the show at the office and tries to make the world a better place through meaningful volunteer work. Her children have all turned out to be pretty terrific adults (I happen to know one of them personally), and she’s got her working-mom philosophy down to a zen-like art.

While we shared our respective backgrounds and stories, she started sketching on a scrap piece of paper a graph method she’s used to evaluate each job or work situation. Then she explained what each section meant, and how she used this simple four-quadrant graph to steer big life/work choices.

Kids have playdates, why can't moms have workdates? Here's a brief account of 3 very different meetings with female mentors, and what I learned from each.

Depending on where she was at any given time, one quandrant might carry more weight than the others. And that’s OK. At some points, she opted for a lateral move to learn new skills and prepare for the next big leap. At others, a more flexible company/culture rose to the top of her priorities, trumping opportunities that might have been more lucrative financially but also more costly in her family/personal realm.

Beyond her killer chart and birds-eye view perspective, what I took away from my breakfast with Nancy was that you can be a baller in the boardroom and a really good, authentic person/mother. She radiates kindness, thoughtfulness, and strength at work, at home … everywhere. I can also tell she’s a shrewd business woman with an intuitive sense of how to manage and lead people, and enough self-confidence to stretch beyond her comfort zone to take on big, meaty challenges.

Even though she’s reached a point where she could comfortably retire and lounge around at her lake house, Nancy isn’t done with meaty career challenges just yet. Her next one? Get herself seated on the corporate board of a large public company—no easy feat when you consider that 80.8 percent of board seats at S&P 500 companies are held by men. (Despite the fact that increasing the percentage of women on a board of directors has been linked to improved financial performance, corporate social responsibility, and an increased number of women in other high-level positions.) I, for one, am rooting for her to achieve her goal (and really, I have no doubt she will).

With these three enlightening workdates under my belt, I plan to continue orchestrating more of these personal/professional conversations with female mentors. How about you? Think there might be an inspirational workdate in your future?

Kids have playdates, why can't moms have workdates? Here's a brief account of 3 very different meetings with female mentors, and what I learned from each.

3 thoughts on “A Tale of 3 “Workdates” with Female Mentors

  1. Great article! I think it is important to make time to reflect on our business and not just be working in our businesses.

  2. Cherylanne says:

    Loved this – and I’m looking forward to our “workdate!” I’m a big proponent of this model but have never thought to coin a term for it!

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