1:1s - Your Core Leadership Operating System
Don’t listen to the naysayers. Eliminating 1:1s is one of the most dangerous ideas in startup/founder mode culture. The advice is coming from people who don’t know how to run them properly.
The 1:1 Is the Leadership Operating System
Why eliminating 1:1s is one of the most dangerous ideas in startup culture and how to run them at the highest level
There is a new narrative spreading across startups:
“1:1s are a waste of time.”
Sometimes it’s framed more elegantly:
“In founder mode, you don’t need 1:1s.”
This is not founder mode. This is leadership malpractice.
The Real Problem Isn’t 1:1s
Bad 1:1s are everywhere.
Unprepared
Status-driven
Manager-dominated
No decisions
No follow-through
The obvious conclusion? “Let’s just eliminate them.”
WRONG!
The issue isn’t the meeting.
The 1:1 issue is the lack of operating system behind it.
What Breaks When You Remove 1:1s
When you stop consistent 1:1s, five things quietly degrade:
Trust
Context
Feedback
Risk
Alignment
If you don’t want or need these 5 attributes in your company’s culture… then YES, you don’t need 1:1s.
You are shuddering at the thought of not having these core cultural elements? GOOD.
I’m a big fan of Raw Signal - Melissa Shapiro and Jonathan Nightingale’s newsletter. We are fellow Mozillians. They write way better than I do… so take it from them!
“I Really Don’t Have Anything This Week”
The single biggest predictor of high-performing, psychologically safe teams is... wait for it... whether employees have regular check-ins with their managers. This seems ridiculous. Like, surely it's got to be more complicated than that. But if you think about it, it makes sense. If you never talk to your own boss, you're left to guess and assume and flail. Sometimes you'll guess right. Sometimes you won't. But you know what you sure as shit won't do? Stick your neck out. Take a big swing. Or say anything even marginally unpopular in a meeting.
If you work at a job or in an industry that doesn't believe in 1:1s, you're not alone. We talk to a lot of folks who have spent time in orgs like that. They tell us it's hard to know what's important. Tricky to figure out if they are working on the right things. That they are frequently surprised to the downside. And that they struggle to get the feedback they need and desperately want.
The word that comes up more than any other is disconnected.
There is no shortcut to the long game. Raw Signal goes on to say:
We've been part of a lot of failed 1:1 cultures. We've worked in organizations with no 1:1s, or with 1:1s so infrequent that seeing one scheduled caused immediate panic. We've worked for bosses so bad at running them that HR would sit in to make sure that they happened, and then apologize to us afterwards for how poorly they went.
We've also been the bosses who have cancelled 1:1s. Been the bosses who showed up excited and prepared for some of them, and avoidant or irritated for others.
Bill Campbell Also Weighs In:
He didn’t over-engineer it. He simplified it.
5 words on a whiteboard. For every 1:1. Simple.
Both people come prepared
Each writes down the 5 things that matter
Overlap becomes the agenda
Conversation goes deep
No templates. No theater. Just signal.
There is no one right way to run a 1:1.
But you must have them! Hard stop.
Real operators know:
1:1s must flex based on:
the function
the role
the maturity of the employee
the pressure of the business
So, as I try to do, I’m going to try to compile everything I’ve ever practiced, read, learned into an operating system.
The Cook’s PlayBooks 1:1 Operating System
Axis 1: Who Leads?
Report-Led (Default for Most Teams)
Used by:
Product
Engineering
Marketing
Ops
People
Why it works:
surfaces real issues
empowers ownership
builds leadership capacity
enables upward feedback
Principle:
👉 The 1:1 exists for the report, not the manager
Manager-Led (When Performance Is Measured Precisely)
Used by:
Finance
Sales
Customer Success
Recruiting
People Ops
Why it works:
tight alignment to targets
faster course correction
clear performance expectations
Principle:
👉 The 1:1 is a performance acceleration tool
Axis 2: Structure Level
Unstructured (Exploration Mode)
Best for:
senior talent
creative functions
early-stage ambiguity
Unstructured does NOT mean unprepared.
Agendas create safety.
Especially for:
introverts
new hires
underrepresented team members
Structured (Execution Mode)
Best for:
quota-driven teams
scaling orgs
high-accountability environments
But structure must include:
space for concerns
space for development
space for feedback
Otherwise it becomes mechanical.
The Design Insight
Most companies or people teams try to force one model. Don’t do that.
Great teams and companies flex across all four quadrants:
Unstructured vs Structured
Report-Led vs Manager-Led
So, there’s your design starting point.
Your Questions Are Your Leverage Point
This is where most 1:1s fail. Not scheduling. Not structure.
Questions.
Specifically, bad questions:
“How’s everything going?”
“Any updates?”
“Anything I can help with?”
These produce:
Nothing-burger answers
No data
Zero Insight
Time wasted
Powerful 1:1 Questions?
For Product Teams:
What decision were you unsure about this week?
What question did you get that you couldn’t answer?
What do you need from me before next week?
For Marketing Teams:
What’s stressing you out right now?
What’s blocking progress?
What feedback do you have for me?
For Engineering Teams:
What’s on your agenda?
What haven’t we talked about?
What would make your job easier?
For Sales Teams:
What are you doing well?
What do you want to improve?
What patterns are you seeing?
For Finance Teams
What systems are working well?
Have you explored AI Agents since we last talked?
What have you learned?
How is the “Product” you are delivering going?
How does your “Customer” like your “Product”?
Never Cancel Your 1:1s
Back to Melissa and Jonathan (RawSignal) - “I really don’t have anything this week.”
DON’T THINK THIS. DON’T DO THIS.
Canceling 1:1s sends a signal:
“You are not a priority.”
Consistency builds trust.
Inconsistency destroys it.
Two More Rules Worth Highlighting
1. Ask These Every Time
“Is there anything you need me to communicate to the rest of the organization?”
“Is there a risk in the company you are seeing that isn’t being addressed?
“Are there any negative cultural issues that you are hearing?”
2. Double Up on New Hires
Meet 2x per week for the first month.
Why?
Alignment is built
Culture is learned
Expectations are set and bad habits are prevented
The Cook’s 1:1 Operating System (Final Form)
Every great 1:1 does five things:
Builds trust
Transfers context
Surfaces risk
Develops judgment
Aligns execution
If it’s not doing these five things…
👉 It’s broken.
The CFO / COO Insight
1:1s are not just leadership tools.
They are: Early warning systems
Before issues show up in:
forecasts
dashboards
board decks
They show up in:
Culture
Execution
Confidence
Cook’s PlayBooks Bottom Line
If you believe 1:1s are a waste of time:
You don’t have a time problem.
You have a leadership design problem.
The 1:1 is not a meeting.
It’s the single most important leadership alignment tool for companies.
Five words.
One real conversation.
Every week.
