An inquiry into the shifting practice of leadership

When I was a young leader, our company followed a rhythm you could set your watch by. 

We would hold a strategic planning meeting in the spring to review our core purpose and values, progress on our BHAG, and update the five-year plan. Over the summer, we turned that plan into a budget that we’d fight over for most of the fall. That budget locked in the specific initiatives we would work on for the following year.

Can you imagine that? We were setting priorities in the spring of one year and delivering on them 9 to 18 months later.

Today, the only people I know who are still doing a “five-year plan” are at non-profits—and they’re usually just using it for fundraising.

We created those artifacts—the BHAGs, the core purposes, the long-term roadmaps—to align our teams around a shared vision. It was a way to coordinate the efforts of a diverse set of smart people without having to negotiate between them every single day.

But I’m noticing a shift.

Instead of those long planning cycles, I mostly see quarterly “rocks.” Priorities are set in much shorter sprints. It’s rare that I see annual budgets used to meaningfully allocate capital and effort anymore. Initiatives pop up organically throughout the year, sometimes lasting only a few weeks or months.

It makes sense. Change is occurring more rapidly than it used to. Geopolitical shifts, technological leaps, and social movements arrive in waves. We barely get our feet under us before the next wave of uncertainty hits. A plan made six months ago can feel irrelevant to the current reality.

But this flexibility also has a downside.

Without those planning artifacts, it’s harder to align our teams to flow together in a common direction. There’s more negotiation; these debates rise to the CEO level more frequently, and the decisions aren’t obvious!

An invitation to inquiry

I find I have more questions than answers here, and I’m curious about your experience. How has your practice of leadership changed in response to this?

How are you aligning your smart, creative people around a shared set of objectives when those objectives might shift every 90 days? How do you decide when to put more money behind one experiment and take resources away from another? How do you evaluate those “one-way doors” that could make or break your company’s future?

I’m in the lab working on some ideas around what leadership looks like in 2026, and I’d value your perspective. Would you hit reply and share whatever thoughts come to mind?

I’d appreciate the chance to learn from what you’re seeing in your own leadership.