I’m scheduled to conclude my COO role in December, so I’ve been writing my transition memo. I started early so I could add ideas slowly, but once I outlined the sections, the content came quickly.
What I didn’t expect was that writing the transition memo would prompt some of the best strategic thinking I’ve done in the role because it forced me to take a different angle. My normal planning routines are oriented more to action—what projects to start and stop based on the current state. The thinking is inherently biased toward the quarter ahead and constrained by assumptions about my team’s current resources and capabilities.
The transition memo, on the other hand, helped me ask more fundamental questions. What’s really going on here? What would be possible if we got rid of the constraints? That thinking pushed me two or three levels deeper in the root cause analysis and helped me focus on organizational culture, team mindsets, and infrastructure—the kinds of things that take several quarters, or even years, to solve.
Once I started having those new insights, I thought to myself, “I should have ‘left’ a long time ago.”
Training my sights on my departure also prompted investments in making the team more resilient. We worked on our shared drive to ensure none of us held access to information individually. Wherever I was the only administrator for software tools, we added a second. And we moved several projects that had been assigned to the COO on a “temporary” basis to their proper owners on the team.
When I step back, these are basic practices we should have put in place long ago.
I also asked myself, “Why did it take a transition memo to get me asking different strategy questions?”
The straightforward answer is that I had told my co-COO that I was a housesitter. I would try to improve the house where I could, but wouldn’t make major renovations, like new large projects or personnel changes. Making that promise led me to approach strategy through a short-term lens.
There’s nothing wrong with creating a plan that accounts for current resources and constraints, but it can become a cop-out for sloppy thinking. My mistake was quietly dismissing those multi-year, potentially foundational initiatives, rather than explicitly including a section in the strategy document titled, “Projects If We Had Unlimited Time and Resources,” and thinking deeply about what it would take to pursue them.
There’s also no reason I couldn’t have pushed the team to ask in our planning processes, “If X is an awesome outcome we want to achieve, what seeds should we plant today?”
That approach—always planting seeds—is useful because it's the middle ground between realism about how much time and attention we have today and the big outcomes we want tomorrow. It can shift us from “what we are” to “what we want to be.”
Short-term planning can include long-term thinking.