
TUESDAY, SEPTEMBER 08, 2026 · ISSUE #07
THE OPEN
Good morning.
If you’ve made it this far with us, thank you. Seriously.
We’ve already had a few readers write back saying they’re enjoying Still Monday, which means either we’re doing something right or everyone is avoiding actual work at the same time.
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And if there’s someone at work who would enjoy this, send it to them. We’d very much like more coworkers around here.
Now.
Yesterday we celebrated workers.
Today we're discussing management.
HR assures us the timing is completely coincidental.
Let’s get to work.
BIG STORY
Your company may have too many bosses
Uber is eliminating roughly 3,300 jobs, about 10% of its workforce.
Normally that headline would lead directly into the usual corporate story about cost cutting.
This one is more interesting.
Uber says part of the problem is the way the company itself has been organized.
Too many layers.
Too much coordination.
Too many small teams.
Too many people managing very few people.
CEO Dara Khosrowshahi said Uber is removing management layers, consolidating teams and simplifying its structure. The company is also reportedly reducing the number of managers by about 20% and cutting the number of tiny “micro-teams” roughly in half.
Which raises an uncomfortable corporate question:
How many bosses does a company actually need?
For decades, the career ladder has worked something like this.
You’re good at your job.
You become senior.
Then lead.
Then manager.
Then senior manager.
Then director.
Then senior director.
Eventually somebody gives you a budget and invites you to meetings called things like:
Strategic Alignment Leadership Forum.
Nobody planned for the organization to become complicated.
It just happened one promotion at a time.
And every new layer creates work of its own.
An employee needs approval from a manager.
The manager needs alignment with a director.
The director wants visibility from a VP.
The VP needs a deck.
The deck needs another version because someone changed the font on slide 18.
Meanwhile, the customer is still waiting.
Uber’s argument is essentially that years of growth produced too much complexity.
That complexity created more coordination, more fragmented ownership, and slower decisions.
There is something very attractive about the solution.
Fewer layers.
Larger teams.
Clearer ownership.
Faster decisions.
But there’s also a catch.
Good managers do useful things.
They teach.
They prioritize.
They remove obstacles.
They help younger employees improve.
They prevent somebody above you from introducing a “quick initiative” on Friday at 4:47 PM.
So the problem isn’t management itself.
The problem starts when management becomes the default reward for being good at something else.
The excellent engineer becomes an engineering manager.
The great salesperson becomes a sales manager.
The brilliant designer becomes a design manager.
And suddenly the company has rewarded someone for being exceptional at their job by making sure they spend less time doing it.
That’s how org charts grow.
Eventually you get someone managing two people who each manage three people who all spend Wednesday preparing updates for each other.
Uber has apparently looked at some of those boxes and decided:
Maybe we can delete a few.
There’s a lesson in there for almost every company.
Not every promotion needs direct reports.
Not every team needs its own manager.
And not every box on the org chart needs another box above it.
Sometimes the fastest workflow improvement is somebody asking:
Why is this approval here?

WORTH KNOWING
01 / Uber is shrinking more than headcount
The restructuring isn't just about eliminating jobs. Uber says it wants fewer organizational layers and larger managerial spans, while reducing tiny teams with just one or two members. The company says the goal is clearer ownership and faster decision-making.
Corporate translation:
Fewer people whose primary job is forwarding something to somebody else.
02 / Changing jobs still pays more
ADP’s newest compensation data shows median base pay rose 3.0% year over year for employees who stayed with their employer.
For people who changed jobs:
4.7%.
When bonuses, commissions, tips and other earnings are included, gross pay rose 4.4% for stayers and 7.3% for job changers.
Loyalty still has value.
The payroll department has simply chosen not to quantify all of it.
03 / Managers may be managing more people
Uber’s changes fit a broader management idea that has been getting more attention: fewer managers supervising larger teams instead of many managers overseeing very small groups.
That could reduce bureaucracy.
It could also mean your manager now has 17 direct reports.
Please schedule your emotional needs accordingly.
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WORK SMARTER
Before adding a meeting, ask one question
Before creating a recurring meeting, write this down:
What decision will this meeting make?
Not:
What will we discuss?
What will we review?
What will everyone update us on?
What decision will actually be made?
If you can’t answer that, try sending the information instead.
If there is a decision, invite the people required to make it.
Not everyone who has ever been copied on the project.
This won’t eliminate meetings.
But reducing eight attendees to four still gives four human beings their lives back.
MONEY
The promotion trap nobody warns you about
Imagine you're making $95,000/year.
You’re good at your job.
Your company offers you a management role at $110,000.
That sounds like progress. Maybe it is.
But now you manage eight people.
Your calendar expands.
Performance reviews arrive.
Hiring arrives.
Budget questions arrive.
Conflict arrives.
Someone named Kyle would like 45 minutes to discuss team dynamics.
Before accepting the promotion, ask something more useful than:
How much is the raise?
Ask:
How many people will I manage?
How much authority comes with the responsibility?
How will my performance be measured?
How much of my current job am I still expected to do?
What is the next compensation level?
And what happens if management turns out to be something I don't enjoy?
A 15% raise can be excellent.
A 15% raise attached to a completely different job deserves a little more math.
STILL MONDAY
BEFORE | AFTER |
|---|---|
Employee | Employee |
EMPLOYEE: Who approves this now?
VP: Great question.
ONE MORE THING
There are really two career ladders hiding inside many companies.
One rewards you for becoming exceptional at your craft.
The other rewards you for becoming responsible for other humans.
Those are not the same skill.
Someone can be an extraordinary engineer, salesperson, designer, analyst or marketer and have absolutely no desire to manage anyone.
Companies that build strong individual-contributor career paths don't have to turn every talented employee into somebody's boss.
That might also prevent a few future meetings.
Everybody wins.
Before you go...
Did you like today’s issue?
Vote below. Or reply and tell us what you liked, hated or want us to cover.
And if you know someone who spends an unreasonable amount of time inside an org chart, forward this issue to them and tell them to subscribe.
Still Monday gets considerably more fun when the office gets crowded.
Technically Tuesday. Emotionally Monday.
— The Still Monday Desk

