Lead Well Part 3: Leading the Work Well, like an Octopus

A few weeks ago, I sat down and did something I'd been avoiding: I tried to get it all out of my head and onto a page.

Just a raw brain dump of every open loop, every stalled project, every person I hadn't gotten back to, every idea sitting on the back burner, every task with no clear home. I put it all in a spreadsheet. It was more than fifty lines.

Too many projects in motion, things left undone and opportunities I hadn't had the bandwidth to pursue. Team members waiting on me to move something forward. And looking at it all laid out like that, my first feeling wasn't panic.

It was vindication.

Yes. This is real. This is more than I can accomplish in a day, a week, or even a month. And yet every single line felt important. Every one of them had gotten there for a reason.

I knew I had a team who wanted to help. I just hadn't done the work of figuring out how to hand things off in a way that actually worked. So instead, I'd been carrying it. All of it. In my head, all the time.

A lot of leaders do this. We wear the mental load like it's part of the job description. And maybe for a season, it is. But we intuitively know it’s not sustainable, and it keeps us from being able to lead the work well.

Later in the week, I came across an article in Harvard Business Review by Jana Wehner and Phil Le-Brun about what they call the Octopus Organization. And it genuinely shifted something for me.

In the article, they describe the subtle but important difference between complicated and complex.

A complicated problem has a lot of moving parts, but it has a clear path from A to B. Think of building a new client onboarding workflow. There are steps, dependencies, people involved, tools to set up. It's a lot, but if you map it carefully and execute well, you get a predictable result. Complicated, yes. But solvable.

Complex is different. Complex is what it actually feels like to run a business right now. Think of trying to build a long-term communications strategy for a client in a rapidly shifting political and economic landscape. There's no clear roadmap. The environment keeps changing. New information arrives, reframing what you thought you knew. The "right" answer isn't waiting at the end of a checklist — it has to be discovered, tested, and adapted in real time.

As Wehner and Le-Brun describe, most of us have been trying to run complex organizations like complicated machines. We build systems and protocols designed to produce consistent, controllable outputs. And then we're confused when the unpredictability of real life keeps breaking the machine.

An octopus, by contrast, doesn't fight the complexity of the ocean. It moves within it. In their words, an octopus “adapts to thrive in a complex environment. Its intelligence is distributed — each arm can sense and act independently, yet all eight arms can coordinate and work in harmony. Now imagine an organization like that: fluid, curious, constantly learning everywhere. Priorities are clear. Ideas shared freely. Meetings flow, and there's no room for jargon. The goal isn't to present, it's to discover. That's an octopus organization. Smart, adaptive, self-aware, nimble, and built to thrive in uncertainty.” 

I want to lead my organization more like an octopus.

What does that actually look like in practice? I'm still figuring it out, honestly. But here's where I'm focused.

Embedding curiosity into the process. When challenges arise, my first instinct is often to fix, to control, to find the fastest path to resolution. I'm working on replacing that with a beat of genuine curiosity. What's actually going on here? What are we assuming, and what haven't we tried? Design thinking has been a useful framework for this: lead with empathy, experiment, and be willing to pivot toward the right direction rather than locking in the predetermined one.

Empowering my team to make decisions. The spreadsheet highlighted something I already knew: I am a bottleneck. Not because my team isn't capable, but because I've held ownership of too many decisions that don't need to be mine. I'm working on giving my team a few clear guiding principles instead of waiting for my input at every turn: What will serve the client best and be good for the company? How does this align with our values of being intentional and effective? That kind of guidance travels farther than a task assignment ever could.

Shifting from delegating tasks to owning outcomes. This one is the hardest. I see it in myself and in the leaders I work with: we want to hand things off, but we struggle to actually let go. I’ll delegate tasks, but struggle to hand off the bigger picture context — which means I haven't really delegated anything. I'm working on front-loading projects with clarity: here's what done looks like, and give my team permission to own the process. My role is to play the supporting character, get roadblocks out of the way, and help foster their own creativity and problem-solving.

Ten years into running this business, I know the tension never fully resolves. There will always be more than I can hold. The environment will always be more complex than my systems can contain. That's not a problem to solve, but the water we swim in.

But leading the work well means building an organization that can move within that complexity, not one that keeps trying to control it. It means trusting my team more fully, staying curious longer, and loosening my grip on outcomes without losing sight of what matters.

The mental tab overload I felt staring at that spreadsheet? That doesn't have to be my normal state. It's just a signal — the same kind my intuition has been sending all along — that something needs to shift.

If any of this resonates with where you are in your own leadership, I'd love to connect. Sometimes an outside perspective is the clearest path to getting unstuck. You're welcome to reach out and schedule a conversation — I'd be glad to think through it with you.

---

This is the third post in a series on the three pillars I'm building my business around: leading myself well, leading my team well, and leading the work well. They're deeply interconnected — and this third one is where the first two show up most visibly. Read the first two posts in this series: Leading Myself Well and Leading My Team Well