“Never mind. I’ll just do it.”

When I joined Freshworks, the CEO didn’t hand me a 90-day plan. He didn’t ask for weekly reports or track me through a task board.

He told me something that roughly paraphrases as:

“I hired you because you’re smart. Go do what you do best. Let me know if you need help.”

That was it. And it worked. Because what he was really giving me wasn’t just autonomy—it was trust.

Later on, that spirit turned into a mantra we lived by: “Be the CEO of your job.”

It was more than a motivational poster. It was a culture of ownership. Not just in job titles, but in the way people showed up—how they asked questions, made decisions, and took initiative. No one was waiting to be told what to do. They just… did it. And when you build a system that supports that kind of ownership, delegation isn’t hard. It’s natural.

But let’s be honest. That kind of system is rare.

In most organizations, delegation looks more like a long explanation, a few nervous check-ins, and then—when things start feeling shaky—that familiar line:

“It’ll just be easier if I do it myself.”

You’ve said it. I’ve said it. Sometimes it’s even true. But most of the time? It’s a sign that the clarity never scaled.

The Real Goal of Delegation is Clarity Scaling

The biggest lie we tell ourselves is that delegation saves time.

It doesn’t—at first. Delegating well takes more effort than just doing the thing yourself. You have to explain, align, sometimes undo. You have to resist the urge to jump in and “just fix it.” And all of that feels inefficient—especially for high performers who pride themselves on speed, quality, and knowing how to get stuff done.

But here’s the reality:

Because if the only person who can make the right decisions is you, then nothing actually grows. The system stays dependent on your brain, your judgment, your bandwidth.

That’s why clarity matters so much. 

Not just what to do—but what success looks like. Why it matters. Where it fits.

In Cognitive Load Is Real, I wrote that overwhelm isn’t always about volume—it’s often about not knowing what matters. Without context, we don’t move with confidence—we tread water, unsure if we’re solving the right problem.

The real goal of delegation is clarity scaling—the process of transferring not just tasks, but context and intent. So someone else can make a good decision without needing you to explain it again.

That’s when delegation pays off. 

Not when the task gets done—but when the thinking behind it gets shared. 

That’s the difference between handing off work and building real capacity.

Why Most Delegation Breaks Down

Let’s name the reasons delegation so often fails (or backfires):

• You handed off a task without the context. No one told them what success looks like, so they guessed—and guessed wrong.

• You gave the what, but not the why. They completed the checklist but missed the bigger opportunity (or landmine).

• You thought autonomy meant walking away. It doesn’t. Autonomy is earned—by both sides. It takes narrative scaffolding and repeated calibration.

• You confused fast output with forward motion. Work got done. But nothing scaled.

This is where systems fall apart—not because people are incompetent, but because there was no clarity to scale in the first place.

In People Like Bad Pizza, I talked about how without clarity on what your customer wants, you may be optimizing for the wrong thing.

Delegation works the same way. Without clarity on what you want, the people you delegate to may be optimizing for the wrong thing as well.

The Deadline Trap

One of the biggest challenges with delegation isn’t mindset—it’s time.

You’re under pressure. There’s a deadline. So you do what you’ve always done: handle it yourself. Maybe you think, "Next time I’ll loop someone in sooner." But “next time” looks a lot like this time. And the cycle continues.

It’s a trap:

Clarity scaling only works when you do it before the moment of need. Before the launch. Before the fire drill. Before the decision has to be made in a hallway.

It's an investment.

It’s a system you build in the calm—so it can function in the chaos.

What Does Good Delegation Actually Look Like?

Here’s the simple test:

If not, you're not delegating—you’re distributing tasks.

Good delegation looks like:

• Sharing the narrative frame, not just the to-do list

• Offering a definition of success, not just deliverables

• Creating feedback loops that reinforce ownership, not dependency

• Checking for shared language, not just shared goals

This is why the internal clarity you create—the one I emphasized in Who Are Your Sensemakers?—isn’t optional. In that issue, I asked: Who’s helping you interpret what matters and what doesn’t? Without sensemakers, even well-meaning teams drift out of alignment.

In other words, delegation works when your story scales. 

That’s what clarity scaling enables.

Clarity Scaling at Home

This isn’t just about teams or startups.

You see this dynamic play out every day in your personal life—especially in families, partnerships, or caregiving roles.

We’ve all had that moment. You ask for help, and halfway through explaining it, you hear the voice in your head: 

“You know what? Never mind. I’ll just do it.”

That’s not a character flaw. It’s a clarity gap.

Want your kid to take out the trash without being reminded? 
Want your partner to handle the party planning without a checklist? 
Want your roommate to grocery shop without texting five times?

That’s all clarity scaling.

And just like at work, it takes effort up front. You have to:

• Create a shared, explicit view about what “done” looks like

• Share your mental model (not just the rule)

• Let go of perfection in favor of ownership

• Create space for learning curves without leaping in to rescue

The goal isn’t perfection—it’s progress. 

And the reward isn’t just getting things done. It’s having people around you who can act with care and confidence, without relying on you to translate everything all the time.

Berkson's Bits

The Workaround Is the Message

People don’t always complain when something isn’t working. They adapt. They patch. They rig up a workaround and keep going.

That’s not just true in software—it’s true in every system: processes, policies, products, even relationships.

If you're trying to improve something—whether it’s an app, a hiring flow, or a team ritual—don’t just ask what’s broken. Ask what they’ve hacked together to make it usable.

The workaround tells you where the friction is. 
The workaround tells you what matters most. 
The workaround tells you what you missed.

Ignore it, and you’ll think everything’s fine. 
Listen to it, and you might find the real opportunity.

What I'm Watching...

A bit of shameless promotion this week. If you happen to be in NYC July 24th or 26th, come see a new musical, WILDERNESS!, composed by my daughter Olivia and directed/produced by my daughter Amanda. It will be part of the SheNYC Arts Summer Festival and you can get tickets here. And here's a sneak peek of them rehearsing the song "My Best Try."

We all operate under constraints: limited time, limited resources. When it comes down to it, clarity scaling is the real work. Delegation isn’t a shortcut.

It’s not about getting more off your plate. It’s about putting in the work now so you can build a system that runs without you at the center. That’s what clarity scaling is all about.

Whether you’re leading a team, raising a family, or just trying to get through the week without carrying everything yourself—scaling clarity is how you unlock real ownership, shared trust, and a little breathing room.

It’s not supposed to feel effortless. 

But it is worth it.

Looking forward to continuing the conversation...

Alan