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Why you feel like the babysitter on the leadership team
Are operators destined to babysit the leadership team forever?
Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.
💡 Hi, Operator! Before we jump in, I have a question for you -
Since launching Force Multipliers, there have been an insane number of people with very impressive backgrounds who have subscribed: Chiefs of Staff and COOs at startups worth billions, operational machines at Google and Salesforce, consultant wizards at McKinsey, Bain, and BCG.
You all probably have your own operational questions and wish you could ask a coach and operator who’s seen it all.
So if I open up “Dear Regina” submissions from all of you, would you write in with your questions?
If the answer is yes, would you please reply to this email and tell me? This will give me a good gauge on how much interest there is. I would keep everything anonymized the same way I do for current Dear Regina entries, giving only your title, stage of company, company size, and approximate amount raised.
OK, let’s get into this issue! xx
Preface
A few months ago, I was part of an invite-only forum for high-performing operators. In it were COOs of companies worth billions, and the purpose was to have transparent conversations to facilitate both decision-making and camaraderie.
During one of the earliest discussions, one of the members in the group asked: “For your next role, would you do the COO role again?”
Unequivocally, every person said no.
Some of the reasons given:
The scope of my role is so ambiguous. I feel like a catch-all for everything the CEO doesn’t want to do.
The work feels thankless. No one really cares unless something is on fire.
Most of the problems I am involved with are people problems, that stem from people with huge egos.
I feel like a babysitter on the team. It’s like I’m the only responsible person on the team - my work feels like chasing after toddlers.
Even if you’re not a COO (yet!), perhaps you feel this way too. I wouldn’t be surprised. Even through a quick online search for JDs of operator roles, here were some of the results:
JD #1

JD #2

See those JDs above? Here’s how most excellent operators ACTUALLY read these statements:
Original JD | How it translates for operators |
---|---|
“Support [the CEO] in ad-hoc tasks, organize and dispatch work in case of business emergencies.” | “Babysit the CEO - because inevitably, they won’t want to do something I tell them they should do. And when consequences come, I’ll be the one putting out the fire last-minute.” |
“Ensure the execution of the most immediate & critical priorities.” | “Babysit everyone and make sure they’re doing what they’re supposed to be doing.” |
“Oversee daily operations, ensuring efficiency and effectiveness across all functions.” | “Babysit everyone and be the bad cop when things aren’t done quickly or perfectly.” |
“Collaborate closely with the executive team to accelerate organizational growth.” | “Babysit the executive team by riding their butts every day and juggling their priorities for them.” |
These kinds of JDs can be frustrating to read. The more senior you are, the more likely you feel like your role sometimes reduces down to babysitting adults.
Let’s talk about how to get out of the babysitting mentality today.
Dear Regina,
Even though I’m a Chief of Staff on paper, I feel like I spend way too much time cleaning up messes that usually come from the leadership team (1) not being organized enough, (2) letting their egos get in the way of good collaboration, or (3) jumping into half-baked initiatives my CEO jumps into before forgetting and moving on.
Just last week alone, I felt like I was herding cats. We have a really big product launch coming up, and it requires a ton of cross-functional collaboration. I found myself spending hours:
Chasing down the Head of Engineering for an update on whether the team is on track with technical deliverables for our launch date
Wrangling the VP of Sales to send me the messaging they’re sharing with the AEs to convert customers so I can make sure it doesn’t introduce scope creep to the eng team
Messaging an IC on the marketing team to share the new copy for our top of funnel, because they completely forgot about the deadline they promised me
Everyone was super slow to reply too, which was so frustrating. And all of this is on top of my regular day-to-day responsibilities as a CoS - my CEO also has work they have to get done, but they have shiny object syndrome and get distracted easily, so I spend more significant effort getting them to focus.
I want to be seen as a strategic leader, not just the person who picks up after everyone. How do I shift out of this dynamic without everything falling apart?
(Chief of Staff, Series A company, ~50 people, $23M raised)
Dear Operator,
The babysitting mentality is real. You’re not alone, and this is a systemic issue that largely comes from the fact that no one really knows how to define an operator role.
Oftentimes, operators get stuck in a cycle of cleaning up after leadership teams, because we don’t take time from the very beginning to define who we are as operators and what our Areas of Responsibilities (AORs) are.
Also, this is a problem I’ve seen more often when operators are hyper-competent: the more organized you are, the more likely you fall into the babysitting role.
Why? Because no one on the team - and I mean this sincerely, no one - will ensure things are done as thoroughly as you will.
The best operators give a shit. And because you give more shits, this makes you good at your job! But this is ironically also what produces your biggest headache: chasing after people. And that is one hell of a paradox.
I discussed in Issue #1 of Force Multipliers the importance of doing work around the work, because the more often you prevent chaos from happening, the less visible your contributions become. So today, we’re going to continue that discussion: let’s talk about how to move from being an enforcer into being an architect.
Case Study: Tony Xu, DoorDash CEO
One of the most inspiring stories I’ve read of an operator saying NO to the babysitter role is about DoorDash’s CEO, Tony Xu.

This interview with DoorDash’s former Director of Operations is just one example of DoorDash’s operational carrots and sticks (edited slightly for brevity):
[Tony] is maniacal about measuring … You're in a weekly business review and he's asking crazy questions like, "What's driver retention in Minneapolis four months ago, where we have 20 markets live?" And someone says, "I don't know." And he says…"If you want to be at this company, that's what you need to know."
I've seen him ask someone the same question like four or five times in a row, and I'm like, "This is uncomfortable." but those meetings were like the Holy Grail. I would study the night before, I would study the morning of. I had to know my numbers and I had to have a plan, because it was going to get just really uncomfortable.
DoorDash has a culture of excellence. Everyone wants a culture of excellence.
I can already hear the voices: “Regina, this is only possible because Tony is the CEO, and he can instill the fear of God into the rest of his team. I can’t do that! No one listens to me!”
You don’t have to be the CEO to do this. Whatever your sphere of influence is at your current company - whether you are an Operations Manager, or a Chief of Staff, or even a junior Operations Associate - you can develop a culture of excellence exactly where you are.
See the Playbook on Architecting below.
The Playbook on Architecting
(instead of Babysitting)
Step 1: Shift your mentality 🧠
It shouldn’t be a surprise to you that the first shift you’ll have to make is a mental one.
A good operator is someone who says, “I will make sure everything gets done by enforcing through chasing.” (Read: “Things will get done when I am an overbearing, resentful babysitter.”)
A great operator is someone who says, “I will make sure everything gets done by enforcing through systems.” (Read: “Things will get done when I set up visible structures of carrots and sticks.”)
I recommend taking a post-it and putting on your laptop: “I AM NOT A BABYSITTER.”
Or, for fun, you can download this photo and set it as your desktop background 🙂

Make no mistake: if you are in a babysitting role, you put yourself there. And so long as you’re always in the weeds, you will never be seen as a strategic partner. It stings to hear, but when you complain about being a babysitter, you have put yourself into a state of Victimhood in The Drama Triangle.
Younger operators might protest and say, “That’s not true! I was forced into working this way! If I didn’t babysit, nothing would ever get done!”
Wrong. Your solution to the problem of people not getting their work done was chasing them down. This was a reaction, not a response.
And so through your actions, you have taught everyone subliminally: If I don’t get my work done, the Chief of Staff will just chase me down and remind me to get it done. In other words, there are no consequences - you have created yourself a babysitting job.
But there is good news! If you created your own problem, you can fix it, too.
The proper solution here is to stop thinking like a fixer, and start thinking like a systems designer. How can you set up a system so everyone is incentivized to do what they say they’re going to do?
Step 2: Set up your carrot using Slack threads 🥕
Using Slack as your carrot is the best for a number of reasons:
First, most companies already have a #shoutouts channel or something equivalent to recognize great work.
If yours doesn’t, set it up. Don’t wait for permission - create it and say, “We all work hard and want to celebrate creating a culture of excellence. So I’ve made this channel so we can recognize people for their deliverables, especially when they’re above and beyond.”
Second, putting 🥕s in Slack makes it easy for people to emoji react, which is the equivalent of dopamine hits for many people. Everyone loves being celebrated, and non-assholes especially love celebrating others. This breeds positive sum thinking in your company.

One of my first managers in tech was amused at the long team shoutouts I would write in the celebrations channel on Slack, and compared the length of my shoutouts to a CVS receipt. I doubt he believes I’ve kept this certificate after all these years. If you’re reading this…hi Brandon!
And lastly, Slack gives it some recorded posterity: you can recognize when people do great work, and they can look back at it and think, “Yeah, I did do good work.” Even the most stoic of technical engineers usually feels pretty good when someone recognizes them for their quiet efforts, especially in the background.
When someone does what you want, make sure you celebrate them. An astonishingly small number of people remember to celebrate and appreciate the people around them - it feels especially weird sometimes to celebrate someone more senior than you, too.
Do it anyway. This will get you more of your desired behavior.
Step 3: Set up your carrot-stick combo using weekly memos 📝
💡 QUICK NOTE ON NOTION HUBS:
Before we talk about weekly memos, we have to talk hubs! If you don’t have a hub set up on Notion for whatever projects you’re working on, you’re missing out and creating babysitting work for yourself.
Every project should have its own dedicated page, with relevant people tagged in as DRIs, relevant links for easy access, a section for weekly memos, and an Actions Task Board. If you don’t, of course you’ll be chasing people down for work.
👉 It’s easy to set a hub up - download my free Notion templates here to get started:
Meeting agendas that don’t suck template
Master Task Board template
Now, let’s talk about the weekly memo. The most important four bits for any memo are:
💡 TLDR | Summary of what is happening in the project, highlighting whether it overall is on track or behind, and tagging the people that still have outstanding projects. |
✅ On Track | Each DRI fills out what things are still on track according to the actions they’ve committed to. |
🚧 Needs Attention | Each DRI shares where they are lagging. |
⛔ Blocked / In Danger | This is the part where people highlight where they need someone to unblock them. |
Here’s an example of a project-based memo that forces accountability:

When you have a weekly memo set up, you get to highlight exactly who is doing what and where.
Then, the only person that you really have to force to read through and comment is the DRI’s manager. It seems devious…but it works.
For example, if the CEO reads this memo every week and comments on it saying, “Why has this been behind for two weeks already?” it serves as a great stick 🏏 to get people to get their work done.
Everyone wants their managers to know when they’re doing great work, and no one wants to be caught by their manager lagging on deliverables - it’s like getting caught with your pants down.
Want a Notion template for these Memos?
Step 4: Set up your stick: accountability action boards ✔️
Action boards are the easiest way to create a stick that doesn’t feel like a stick. This is because no one can fault you for wanting to keep track of who is doing what. So use it!
I recorded an extensive tutorial here that will teach you to make an Accountability Action Board on Asana. I recommend watching this one at 1.5x speed:
Accountability boards are incredible because it makes it abundantly clear who owes you what.
You can build a system that automatically notifies someone when their action is almost due or past due.
You can get the board to babysit for you.
And best of all, you can simply take a screenshot of everything red and stick it in your weekly memo. This creates visibility, so follow-ups aren’t your direct responsibility.
What kind of parent operator are you?

Are you a helicopter operator, an absent operator, or an involved operator?
Writing about operational babysitters reminds me a lot about parenting. There are a few stereotypes of parents: the helicopter parent, the hands-off parent, and the involved parent.
See if you can identify the kind of “operating parent” you are below:
Helicopter parents monitor their child’s every move - they hover and yell, expecting excellence at all times and allowing very little leeway for errors. They usually mean well, but they use brute force to get their way, often thinking of themselves as martyrs to their families. Children who have this kind of parent tend to grow up nervous and anxious, and usually want nothing to do with their parents the second they’re old enough to be self-sufficient.
Hands-off parents expect their kids to manage themselves - they offer little to no support when it comes to the child’s responsibilities at school or at home. These parents see themselves more as friends to their children, rather than as trusted adult figures. Without proper guidance and boundaries, these children usually have a hard time adjusting to the real world, coddled by an upbringing with zero consequences.
Involved parents ensure a relationship of respect with their children, but remember children need guidance and routine to do well. Instead of helicoptering their way to excellence, they set up systems that encourage their children to be self-sufficient, rewarding good behavior and letting their children deal with real-world consequences when they choose to misbehave. This is obviously the preferred type of parent.
Most of us who fall into the babysitting category are probably helicopter operators. We’ve stayed this way for so long because we care. We also tend to get very judgmental towards the hands-off operator, who is scatterbrained and largely ineffective.
But there is the third choice: the cleverest of operators knows they can be involved by setting up systems of carrots and sticks, and allowing people to fail if they need to fail to learn their lessons.
Ultimately, it’s great news that you can get yourself out of the babysitting role. If you do all of the above and still think you’re a babysitter, ask yourself: where are you still helicoptering? How can you either let go of this responsibility, or create a system that incentivizes the desired behavior?
Until next time,

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About Regina Gerbeaux
![]() | Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale). 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 Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.
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