Change Management at the Highest Difficulty Setting
Reading the room is the best predictor of success
I was once tasked with rolling out company-wide project portfolio governance at a late-stage startup, right after a round of layoffs. A key part of this was to find a way to keep track of all in-flight projects: current state, estimated ship date, risks, etc, then share a summary on a regular cadence.
My Approach
First and foremost, I read the room. In my experience, projects fail most often due to human reasons (e.g., inability to communicate, insecurity, or competition), not because of broken processes or unrealistic plans.
What I Had Going For Me
There wasn’t pushback on the need to report on the work - given the complexity and high project costs, this was widely seen as reasonable
Ditto the above re: scheduling regular status meetings
I knew and had good relationships with many of the people leading the projects
I started at the company as a program manager and had a strong record of cross-functional collaboration
What Wasn’t Working in My Favor
The company had gone through an extreme amount of change in a very short time:
A couple rounds of layoffs, including one that coincided with this new portfolio strategy
Intense levels of startup chaos in a very fast-paced, growing company
Siloed teams with different collaboration practices
The overall vibe was a combination of change fatigue and job security angst, plus typical startup disdain for rigid process. Success would mean careful calibration between meeting leadership expectations vs. alienating my colleagues.
The Strategy
I chose to lead from a place of empathy. My newly reorg-ed team had a mandate to build out enterprise-grade structure, and the company’s leadership had a very specific idea of what that should look like. The expectation was that my team would expand the project oversight practices we’d been using across a smaller portion of the company.
Mandate or no, I wasn’t comfortable with simply telling my teammates “ok, now we’re going to do things our way.”
I framed my rollout plan around two assumptions:
“Our way” wasn’t necessarily the best way
My colleagues would respond better to the opportunity to co-create the solution
How It Played Out
This might have been straightforward at a more stable company: most people would pick a template, socialize it with leadership, and roll it out with a comms plan. However, given the change fatigue, imposing yet another operational mandate felt dicey, so I chose a different path.
For the first few status meetings, I told everyone:
Come as you are. Report in whatever format you’ve been using, so we can learn from each other.
Each week, I copied all the formats as-is into a combined written doc, then added a summary page and a note that we were exploring a standard template.
The executive report looked chaotic. Leaders generally expect crisp, consistent reporting, and this company was no exception. I cringed at publishing something so unpolished. However, we were getting the baseline information we needed. The only “problem” was whether it looked pretty.
I made a deliberate choice to let this go on until one of two things happened: the group self-selected a new reporting standard, or asked for direction. The latter happened (fortunately, around the time I was pressing my luck with the exec team), and I supplied the format I’d been using. There was zero pushback.
The Outcome
Within two months, we aligned on a standard reporting format, and the entire company had a clear (and well-formatted) view into the portfolio.
What I Incorporated From Crisis Counseling
Trauma-informed leadership relies on safety, trustworthiness, transparency, and empowerment. People experiencing trauma (e.g., job insecurity) can’t do their best work without psychological safety.
A top-down approach of “do it my way” — the polar opposite of empowerment — can trigger resentment, anxiety, and fear of being the next person to be let go. Even something as simple as a template can become symbolic and impact workplace relationships.
This isn’t the way I want to treat other humans. Moreover, on a pragmatic level, even if you don’t care about people’s feelings, this approach won’t produce quality work or a committed team.
The Lesson
The best-laid plan may look great in a slide deck, but it won’t work without real commitment. Resist the need for control: meeting a state of chaos where it is can be a surprisingly effective choice. Let people breathe, and they will often gravitate toward alignment.