When Dave Girouard hired me at Google, he told me my job was to get all the schools in the country using Gmail for their email. I asked him how he wanted me to do that. He said, “That’s what I hired you to figure out.”

I’ve been lucky to work for bosses who trusted me with autonomy I hadn’t yet earned. Dave was the most important — and not just at Google. He’d hire me again years later to help build Upstart, and the same pattern played out there. Looking back, the trust he extended is the single thing that made the biggest difference in my career.

It’s also the framework I find most useful for thinking about how careers actually progress. Not title, not comp, not team size — those are the trappings of seniority. The real measure is trust. Specifically: how much does your organization trust you to operate autonomously? And that trust comes from one thing — demonstrated judgment.

There’s a spectrum of autonomy I think captures how careers actually progress. I’ll break it into five levels for the sake of explanation, but think of it as a continuum — the transitions between levels matter more than the labels.

The spectrum

Level 1: You can complete a task with guidance. Someone tells you what to do, and with some help along the way, you get it done. This is where everyone starts. The task is defined for you and the path is mostly laid out.

Level 2: You can complete a task without guidance. Same situation — someone hands you a project — but you can run with it. You don’t need check-ins or hand-holding. You hit a wall, you figure it out.

This is where a lot of career frameworks stop. They focus on increasing the complexity of the tasks you can handle at level 2. Can you do a harder project? A bigger project? A more ambiguous one? That progression is real, but I think the most important transitions happen next — and they’re a fundamentally different kind of growth.

Level 3: You can identify what needs to be done. This is the first big shift — from execution to identification. Instead of waiting for someone to hand you a project, you’re the one surfacing problems, opportunities, things that aren’t working. You come to your boss and say, “Hey, I noticed this issue. What should we do about it?”

Level 4: You identify the problem and propose a solution. Now you’re not just bringing problems — you’re bringing plans. “I noticed this issue, and here’s what I think we should do about it.” The conversation with your manager shifts from “what should I do?” to “here’s what I’m thinking — does that seem right?” You’re doing the thinking. They’re sanity-checking.

Level 5: You identify the problem, develop the plan, and start executing. You come to your boss and say, “I found this challenge, here’s the approach I’m taking, and I’ve already started.” Sometimes they just see the results. At this level, you’ve internalized what matters to the organization well enough to move without waiting for direction.

Context and judgment

The jump from level 2 to level 3 is where careers really break open, and it’s worth understanding why. Levels 1 and 2 are about execution skill — getting better at doing the work. Level 3 and beyond are about something different: understanding the broader context of the organization well enough to know where the important work is.

That’s what I mean by judgment. It’s not just “I spotted a problem” — it’s “I spotted the right problem.” The one that actually matters to the business, the team, the customers. The one that’s high leverage. Anyone can generate a list of things that could be improved. The hard part — the part that earns trust — is knowing which ones are worth spending time on.

I had a moment like this early at Upstart. I’d been hired to build out university partnerships — that was the strategy when I joined. After a few months in the role, I’d become convinced that university partnerships weren’t going to be a winning channel for us. I went to Dave to tell him, half-expecting I’d just talked myself out of a job. Instead, he said, “Well, your job is to figure out what we need to do instead.”

That’s the thing about high-judgment people. They don’t just do what they were hired to do — they figure out what actually needs to be done, even when that means changing the plan entirely. And the bosses who hire that way know the most valuable thing they’re paying for isn’t the execution of a strategy. It’s the judgment to recognize when the strategy needs to change.

The communication part

Here’s the part I had to learn the hard way: autonomy without communication isn’t really autonomy — it’s just operating in the dark.

Earning the trust to run on your own doesn’t mean disappearing. The opposite, actually. The people who get more autonomy over time are the ones who keep the people around them well-informed about what they’re seeing, what they’re doing, and where they’re heading. Not as a check-in or an approval-seeking exercise — just as a normal part of how the work happens. That’s how trust compounds. Your boss doesn’t get blindsided. Your peers stay aligned. People learn to trust your direction because they’ve been watching your judgment in action all along.

This is also where the best mentoring and collaboration actually happen — not in scheduled coffees or formal programs, but as a byproduct of communicating about the work itself.

If I had a career do-over, this is the thing I’d push myself to do better. I’ve always been more comfortable putting my head down and operating than narrating what I’m doing. But the more I look at the people who’ve successfully built careers around real autonomy, the more I notice that they over-communicate, not under-communicate. The trust to run comes from the people around you having clear visibility into where you’re running.

What to do with this

If you’re trying to grow, stop thinking about career progression as “doing harder things.” Think about it as earning more autonomy. And be honest with yourself about where you actually are on the spectrum.

Moving up isn’t just about being more proactive, though. It’s about investing in context. Learn how the business works beyond your team. Understand what your boss cares about, what their boss cares about, what the organization is actually optimizing for. The better you understand that broader landscape, the better your judgment gets about where to focus.

And then communicate as you go. The people who earn the most autonomy are the ones who make it easy for everyone around them to trust where they’re heading.

That’s what seniority actually is. Not a title on a leveling rubric — it’s your organization trusting you enough to let you run, because you’ve shown the judgment to run in the right direction, and the discipline to keep everyone else in the loop while you do.

Dave didn’t hand me a job description at Google. He handed me trust. Almost everything I’ve learned about careers since then has been about how to earn that, over and over.