What a Difference a Decade Can Make
On practicing connection, one introduction at a time
When I returned to Microsoft in November 2015, I decided I was going to do things differently than I had the first time I worked there.
I didn’t have a full plan. I had a starting point.
Find a mentor.
My manager at the time paired me with a PM. We could not have been more different. She was outgoing in a way that felt almost performative to me. Energized by meeting new people. Curious in public. The kind of person who would walk into a room and leave with three new contacts and a follow up coffee already scheduled.
I am not that person.
Her first goal for me was simple.
Meet one new person every day.
I laughed. Out loud. I told her there was no way I was going to do that.
But I tried it.
Not every day. Some days I skipped. Some days I took the long way back to my desk to avoid it. But on quite a few days, I did introduce myself to someone new. I had a short conversation. I asked a question. I made a connection I would not have otherwise made.
It was a small change.
And then those changes started to grow on each other.
In 2016, I joined the Microsoft Hackathon. That was not something I would have signed up for a year earlier.
My team ended up winning first place for our work with a non profit. We were invited to present at a Satya town hall, and I found myself lobbying to be one of the speakers.
If you had worked with me a few years earlier, this would have been surprising. I would have been the person hoping someone else would volunteer.
Over time, those small behavioral changes continued to compound. A couple of years later I became a team lead. Several years after that I found myself in rooms with directors and VPs, representing my team’s work and answering questions. I was on a path I had not imagined for myself when I started.
I still would not describe myself as a “people person” in the way that mentor was.
But I do appreciate human connection.
This year, I saw an idea from John Benson on LinkedIn about reaching out to colleagues in recognition of Mental Health Awareness Month in May. In the past, I have tried to organize something with my team each year.
This year, I don’t have a team.
So I decided to do something different.
I sent an email on Friday to my skip level manager’s organization offering twenty one‑to‑one conversations in support of Mental Health Awareness Month. The topic can be anything. It doesn’t have to be about mental health. It can just be a chance to make a human connection.
So far, two people have taken me up on the offer.
A third person reached out mostly in shock that I would even suggest it, someone aware of my introverted nature.
And yet I truly believe that the only way we move forward through everything happening in the world right now is by reaching out to the people around us.
If you had asked me twelve years ago whether I would be doing this, or joining leadership meetings, or volunteering to speak at a town hall, I would have asked what you were smoking.
But with enough small steps, taken often enough, the road changes.
We tend to imagine growth as a turning point.
In practice, it is usually a set of small choices that compound until you find yourself doing things that once felt impossible.
Alison + Wiggins

