Diary of the Lady Boss
Lessons learned from the first For the Women Retreat
I’ve been staring at the blank screen for two weeks now, trying to capture the myriad of things that happened during the first official FTW Retreat. What makes the experience so difficult to write about? The answer, as I’ve come to conclude, is that words aren’t always enough to capture experience.
Words are building blocks to describe a succession of events — using them to express feelings resulting from a shared experience is a far more complicated task. Because that is what needs to be done here — the FTW retreat certainly follows some expected customs, such as having a loose schedule for the day or planned meals. The most important part of this weekend, however, was the internal alignment the women experienced together, in a safe space surrounded by supporters.
Joan Erikson once said that we ought to keep some things secret so they have a chance to become part of ourselves. The magic of the retreat experience is one of those secrets. While the magic is settling and internalizing, here are some facts that words are equipped to express.
Work for diversity
This group of 10 women bosses in tech are experts in a variety of fields: design, engineering, product, finance, and sales. We have different lifestyles and vary in age and years of experience, from first-time managers to VPs at established brands. We were brought up in varying family dynamics and under cultural influences from Asia, Africa, and the Americas.
We couldn’t be more different from each other. Conversations on childbearing, mistakes made in our careers, and salary negotiation were broad and deep. Fresh perspectives enriched what we know, and inspired better questions about what we have yet to discover.
I reflected on my own US green card process and was pained by the weight of ageism in the Canadian counterpart casted upon truly talented women. I recognized that talking about the story of my painless IUD insertion experience during the retreat was not enough. I need to share my experience with more women more broadly so others who undergo the same choice can have a clearer expectation. I am inspired to sponsor more women and ask to be sponsored.
Recruiting a diverse group of women for the retreat was a choice, and it took more poking and cold-emailing than I was comfortable with. But it was so worth it. For the next retreat, I aim to gather an even more diverse group.
Build and seek your community
As we grow as leaders, we have the responsibility to build and seek out our community because we continue to face firsts. As the firsts get tougher and the stakes higher: manage up, say no to the reorg, execute the reorg, manage underperforming reports, lay someone off.
To navigate through complex challenges, we need a trusted circle to vent in, gut check, and share dos and don’ts, so we can come up with well-investigated answers. And they in turn build our confidence and make us better leaders.
Building and seeking out our community is a virtuous cycle, no matter how small the community is. I felt a renewed sense of confidence and belonging after the retreat, thanks to the collective wisdom of the group who are navigating similar challenges.
In confusing and disorienting times, we need fewer solitary geniuses and many more connected minds. Who are in your trusted circle?
Optimize for depth
The question has many layers. It implies action, intention, presence, and the ever-changing nature of life. What you will optimize for in the next hour might be different from what you are optimizing for now.
One of my meditation teachers once says that his KPI (Key Performance Indicator) is the number of his students who become teachers themselves in the future. For him, depth is far more important than breath.
That resonated with me. FTW Retreat is optimizing for depth. A deep sense of connection amongst women leaders in tech, so that the group will be there for each other far beyond the weekend. It means that having more women in a single retreat isn’t an option, and fewer days aren’t going to work. It means that my measure of retreat success is the number of coffees, dinners and Zoom sessions amongst the group over the next 12 months. It means that my work doesn’t end after a retreat.
In tech, we often talk about scale. Can we tilt our head and investigate the concept vertically? Our group thread is already 21 emails strong with new questions and insights, so I’m hopeful.
When the plane took off from Montréal on Monday, I felt a rich fulfillment, as if I had just finished a delicious meal. I tried hard to cement the flavors of new kinship and ideas in my mind, and only to be reminded of the powerlessness of my attempt.
Just like trying to use words to utter magic.
Details for the next FTW Retreat will be announced soon. Sign up on the website to be in the know.