The Flip Side of Delegation

If you're just joining us, it might help to read last week's issue, where I talked about why too often we end up muttering:

"Never mind. I’ll just do it."

Delegation doesn’t fall apart because people are lazy or bad at their jobs. It fails when no one really owns the outcome.

That’s the flip side of delegation: ownership.

When I started at Freshworks, the CEO asked me to put together a 30/60/90 plan for my new role.

Sounds reasonable—except the role didn’t exist yet. No template. No onboarding. No playbook. Just me, a vague title (I was actually told I could make up any title, just not CEO), and a wide-open runway.

So I did what needed to be done. I figured out what outcomes made sense. I mapped how I’d get there. I found collaborators. I explained why any of it mattered.

In other words, I wrote the business plan for my own job.

The CEO didn’t tell me what to do. But he did give me what I needed: context.

That was the mission. Everything else? My job to figure out.

When I interviewed candidates in those early days at Freshworks, I’d always say, “You need a high tolerance for uncertainty to succeed here.” What I really meant was: you need to take ownership of the context you’re handed.

That’s how stuff gets done. That’s ownership.

Last week I wrote about how at Freshworks we used to say “Be the CEO of your job.”

This week is about what happens after you accept that. When there’s no playbook—just context and a blank page—that’s when ownership kicks in.

The Chaos Factor

I speak with startup founders all the time. A common refrain? Startups are chaotic. There’s uncertainty everywhere—in what you’re doing and how you’ll know if it’s working.

Most people think that means you need more control. More structure. More checklists.

That's not it.

You need to give people the bigger picture. The why. The outcome that matters. That’s what gives them the ability to make smart decisions and adapt as they go.

Will everything they try work? No. But you’ll never scale if you don’t let people try—and sometimes fail.

Early on at Freshworks, we hired someone to build out professional services. Big résumé. Had done implementations for a global systems integrator for one of our biggest competitors. But he couldn’t get past the fact that we didn’t have formal processes or documentation yet. He got frustrated and left.

The next hire? Jumped in and got to work. Built what was missing. Took ownership of the outcome—successful implementations—and filled in the gaps along the way.

That’s the difference between expecting someone to hand you a perfect setup… and owning the result.

Task Management ≠ Delegation

Here’s a trap I see all the time:

You hand someone a task. You tell them exactly how to do it. You check in constantly.

That’s not delegation. That’s task management. Delegation means giving someone the outcome and trusting them to figure out the path.

One of my favorite questions when starting a project is: “How will we measure success?” That’s the handoff. Even if the target is a little fuzzy, you’re at least aligned on direction. Back in People Like Bad Pizza, I wrote about how success isn’t a fixed thing—it’s contextual.

Delegation works the same way. If you don’t align on what success actually means—for them, not just for you—you’re just assigning tasks. Not outcomes.

That one sentence—“Raise awareness in North America,”  was enough. It gave me the context I needed to make decisions and prioritize. If the CEO had said “go build community” and walked away, I might’ve gone in ten different directions that didn’t matter.

Context gives you direction. Ownership gets you there.

I’ve said before that cognitive overload usually isn’t about how much you’re doing—it’s about not knowing what matters.

Clarity fixes overload—but without ownership, it just sits there.

It’s ownership that turns direction into momentum.

You Don’t Need a Title to Take Ownership

Ownership isn’t about a title. Every role has outcomes. Every job impacts someone.

You don’t need to be a founder—or have “lead” in your title—to act like your work matters. Because it does.

When people do that, a few things happen:

• Leaders stop micromanaging

• Teams move faster

• Trust gets built

• Work gets better

And the people who step up? They’re the ones who grow.

Who Owns the Outcome?

Everyone wants to scale. Everyone wants clarity.

But clarity alone won't get you anywhere. Someone still has to take the wheel.

So here’s the question I always come back to:

If it’s you—own it. Ask questions. Get clear. Make it yours.
If it’s someone else—don’t just assign it. Set them up to own it.

Delegation and ownership go hand in hand. You don’t get one without the other.

If you’re leading, your job isn’t just to offload tasks—it’s to make space for others to step in and take the wheel. And if you’re on the receiving end, don’t wait for someone to spell it out. Own it.

Because clarity without ownership is just a nice idea. And ownership without clarity is just chaos.

But when you’ve got both?

That’s when “Never mind, I’ll just do it” becomes: “I’ve got this.”

This Applies Everywhere

I see this show up outside work too:

• You ask your teenager to plan a family trip… and then second-guess all their choices.

• You volunteer for the school fundraiser… and keep jumping in with “how it should be done.”

• Your partner offers to get the car serviced… and you hand over a bullet-point checklist and tell them what time to schedule it.

In all of those, you’re getting the task done. But you’re not building trust. And you’re definitely not making space for someone else’s thinking.

The hard part isn’t delegation. It’s staying out of the way after you delegate.

Berkson’s Bits

Want to spot where things are breaking down? 

Don’t just ask what’s missing. Ask what people are doing to work around it.

Are they building spreadsheets to patch broken processes?
Skipping tools that are too clunky to use?
Leaning on one person to cover for a missing skill?

Workarounds are signals.
They show you where clarity is lacking, ownership is overloaded—or your systems just aren’t working.

What I’m Watching...

I don't normally share quotes from celebrities. Still, many of you know I'm a NY Mets fan and I love this clip from Francisco Lindor's response when asked what keeps him motivated throughout the season. "I'm not motivated. I'm disciplined..."

The next time someone hands you something—or you're about to hand something off—pause and ask:

“Who owns the outcome?”

If you can’t answer that, you’re not ready to delegate.
And if you’re on the receiving end, don’t just take the task. Take ownership.

That’s how you turn “I’ll just do it myself” into “I’ve got this.”

Looking forward to continuing the conversation...

Alan