Context: this was my first time entering a traditional org that never had product before.
I had no idea just how hard it would be as an outsider.
My boss and I were both new, and everyone we worked with had been there for some time.
Ok, let's dive in.
❌ Making changes too soon without context
We thought the team was too large and wanted to split it to two teams, putting more emphasis on certain areas and less on others.
We failed to communicate the benefits we saw along with where we wanted to take the team.
The team didn’t want to be split and rebelled!
They escalated to the highest stakeholders. There was backlash.
It became much harder thereafter to have much influence on the team. It was easier for them to push back and much harder for me to deliver impact.
Ouch.
This one still hurts when I think about it and is so obvious in hindsight.
People mistakes are the worst mistakes.
✅ I should’ve spent more time learning what was working and what wasn’t, creating strategic context, and bringing the team along, amongst other things.
❌ Working independently for too long
When I was asked to work on an important project, I did so independently in an org that valued collaboration and consensus.
When I tried to gain buy-in for ideas, I was already too far along and couldn’t seem to get others to where I was.
✅Over time, I learned to work with people early and often to bring them along for the journey.
Product success/impact is directly correlated to how much trust you’ve built, not how many frameworks you know.
Take it from someone who learned this the hard way.
❌ Failing to proactively deliver value
I had ideas but didn’t have the evidence to back them up. Because of my early mistakes, I felt immobile and lacked confidence.
I fell into bad habits. I wasn't delivering value.
But, there was hope. Not everything was terrible! I had other wins - it was just a mixed bag.
So, after taking a vacation and reflecting, and some lucky environmental changes, I decided to stick it out.
I treated my situation as a problem to be solved vs. an immovable obstacle.
Then, opportunity struck: A new initiative needed me.
✅ I committed to better habits and practices. I did proper discovery, brought people along, shared context.
I built a team. We executed. We had positive results. We shared them broadly.
I gained allies and influence.
By the way, this thread talks about how I do discovery and bring people along: