Step 1: Force clarity on what the company actually cares about 🎯 

Before you can prioritize anything, you need to force clarity from your leadership team.

I learned this the hard way: most executives don't actually know what their real priorities are. They think they do, but when push comes to shove, they're just as reactive as everyone else.

Every time I prioritize my time, I ask myself: what are the things my exec wants to achieve? To help me understand what I should be spending my time on, I frequently reference the goals they have set.

I created a Goal Tracker and reference it constantly. My friend Jeff Bargmann calls me the "Project Manager to Matt Mochary's life." I like that, actually.

By defining my exec's goals, I can now figure out what would make them feel like a superhuman by tracking all my actions back to their goals. As a Chief of Staff, my exec's goals are my goals.

Force the choice. Make them pick.

Step 2: T-shirt size everything by impact and effort 👕 

Now that you know what the company actually cares about, you need to assess your own work using what I call operator t-shirt sizing.

For every project or request that comes your way, ask two questions:

• How big is the impact? (XS, S, M, L, XL)

• How big is the lift? (XS, S, M, L, XL)

Always choose big impact, low lift first. Then big impact, higher lift.

But here's where most operators mess up: they don't know how to assess "impact" when they don't own a single domain.

To know impact, you have to know what the company cares about and what will make a measurable difference.

Here's my t-shirt sizing guide:

Impact Sizing

• XL: Directly moves the needle on company priorities, visible to board/CEO

• L: Significantly advances department goals, clear measurable outcome

• M: Meaningful improvement to team/process, some measurable impact

• S: Nice to have, minor efficiency gain

• XS: Busy work, no clear connection to company goals

Effort Sizing

• XS: < 2 hours, can do today

• S: 2-8 hours, can finish this week

• M: 1-2 weeks of focused work

• L: 2-4 weeks, might need help from others

• XL: 1+ months, major cross-functional effort

Step 3: Master the art of strategic "no" 🙅 

Here's where operators get into trouble: they think saying no to leadership will hurt their career.

Wrong. Saying yes to everything will hurt your career. You'll become known as the person who's always overwhelmed and never quite delivers excellence.

But saying no doesn't always have to sound like a no. Here are the scripts I use:

• Iceboxing it: "Not now. Let me put this on our roadmap for next quarter."

• This, then that: "Once we're done with X, I can tackle this. For Y to happen, we need to finish X first."

• Seeking clarity: "Help me understand where this fits with our top 3 priorities. What am I missing that makes this more important than [current priority]?"

• Delegating: "Actually, [name] would be better suited for this. They have more context on this area than I do."

Notice none of these sound like rejections. They sound like someone who's thinking strategically about resource allocation.

Real example: I once was asked by a boss to create a coworking space. Like, buy a building and make a place for people to come cowork. No, we weren’t running a coworking company. 😂

I delayed responding by a day because I knew it wasn't important. When I asked the next day, "By the way, did you still want this?" my boss had completely forgotten they had even asked. That was the icebox in action.

Step 4: Delegate everything you're not great at 🐝 

This is where most operators fail when they try to implement this framework.

They feel like they have to hold on to control of everything. They can't let go.

If you're able to delegate all the things you're not good at or that you don't enjoy doing and focus on the things you really enjoy, you'll become a better operator for it.

There's also a lot of work being done right now that's pretty meaningless. It would be better for everyone involved if we let go of the meaningless work and focus on what is actually moving the needle forward.

When Matt completed his Energy Audit, I understood the tasks that absolutely drained him: operations, admin tasks, ordering things, and pretty much anything that doesn't involve creating meaningful connection with other human beings.

Knowing this, I could take those tasks off Matt's plate and either outsource admin tasks to my EA, outsource tasks to other members on the team who were frankly better at them and enjoyed them more than Matt, or handle them myself.

Step 5: Review and course-correct weekly 🗺️ 

Most operators are terrible at auditing their own time. They think they're working on strategic stuff, but they're actually just responding to whoever pings them most recently.

You need a weekly review process.

I recommend using project-based syncs on a weekly or bi-weekly basis. Update on what's on track, what's in danger, and what's fallen behind. Include a "Things I Need" section to get people to give you what you need to move forward.

But more importantly: use your managerial 1-1s to solicit feedback on whether you're working on the right things.

Most operators expect their managers to run their 1-1s. Wrong move. You should manage up by having an agenda. That agenda should include: "Review my projects and tell me whether I'm working on the highest leverage stuff."

Want more operational content?

Check out Coaching Founder for downloadable Notion templates and write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner, daughter, and dog, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.