Lessons From An Angry Uber All-Hands Meeting

The hardest test of leadership isn't giving — it's taking away

May 09, 2025

👋 Howdy! Claire here, Founder & CEO of Canopy. I’m coming off a busy week of facilitation (I ran executive session in Palo Alto, and a few manager trainings remotely), and eager to get back to writing. Lots of ideas are simmering, I look forward to sharing in coming weeks ✨

This week, I’m reacting to something I read the other day — would love to hear what you think in the comments, too. And, do consider sharing this piece with a friend or colleague who you think might find the piece interesting as well…

The other week, Uber employees exploded in anger at their CEO during an all-hands meeting. But what caught my attention wasn’t the pile on Uber — it was the painful reminder of a lesson many leaders, myself included, inevitably face:

The hardest test of leadership isn’t giving — it’s taking away.

Uber’s senior leadership team recently announced they were rolling back certain employee benefits, notably increasing mandatory in-office days and raising eligibility for their popular month-long sabbatical from five years to eight. Employees nearing their five-year mark weren't grandfathered in, leaving many feeling betrayed. One employee's comment particularly resonated with others:

“How is five years of service not a tenured employee? Especially when burnout is rampant in the org.”

The anger spilled into the press, turning a private internal dispute into a public spectacle.

Reading this story, I felt deeply for the employees worn thin. This sabbatical felt like a rare recognition of their hard work — only to have it abruptly deferred, seemingly arbitrarily.

I also imagined that senior leaders likely didn’t enjoy making this decision. Driven by challenging realities of market conditions and financial pressures, these are arduous decisions, stressful if not haunting. And usually, they’re chosen as the best option from grim alternatives.

Yet I do believe Uber's situation didn't have to spiral into such backlash. If you feel like you have to take something away from your team, there are worse and better ways to do it.

A few notes on a better way…

Be transparent about what’s truly at stake.

Why now? Why not before? There's a reason why Uber’s leadership team decided that now, not say two years ago, was the time to change the company's benefits. Uber’s CEO shared how the company needs to go from being “good” to “great”...

But what does “good” to “great” actually mean? What’s really at stake? For example:

Is it about financial stability?
Avoiding layoffs?
Positioning for long-term growth?

Transparency about the gravity of the situation doesn't scare employees — it respects their intelligence. Without context, tough decisions feel arbitrary and unfair.

Communicate what's being gained — not just what's lost.

When you take something away, it's going to cost you. But you do it because you feel like there's something to gain.

In Uber's case, it was clear what the cost was. But what was the gain? Senior leadership could have clarified what they were hoping to achieve:

Will reduced benefits mean greater job security?
More resources for critical projects?
Enhanced long-term opportunities?

Based on the reaction shared publicly, from the employee perspective, it felt like all pure cost to them — and nothing to be gained. They were given no other reason to feel differently.

Offer a sliver of choice, even when some choice is being taken away

Resentment builds not when you’re just taking something away — it’s when you’re removing a sense of autonomy that people have. And that removal of a sense of autonomy, a sense of control, can in fact be sometimes more infuriating than the loss of the thing itself.

Offering choice — even the smallest sliver you can imagine — is most helpful in these situations. Even when you’re faced with the tightest of constraints, there is often some small semblance of optionality or flexibility you can provide. For example, specific to Uber’s sabbatical benefit in question, you could:

Grandfather in people within a certain time range of meeting the five-year requirement.
Allow alternatives, like choosing between benefit options (e.g., opt-in for the eight-year sabbatical redemption mark or a pay raise or a leveling or growth opportunity)
Provide some flexibility for those eligible for the sabbatical to rotate on timing, so not everyone takes it all at the same time

Even the most minimal of optionality can inject some sense of agency.

Plain old heart ‘n empathy.

Take a moment to put yourself in the shoes of the Uber employee who’d already booked their sabbatical:

“I’ve worked so hard. Felt like I’ve given the company my best. This sabbatical was a few weeks out. The trip was booked, I’ve made plans with my family. And then, all of a sudden, it’s torn out from under me and I’m told I need to wait a few more years.”

My sense is that this was not a scenario the leadership team had internalized. They likely had not embodied what it might actually feel like to have something taken away from them. It’s easier to think: “Well I've never taken a sabbatical, but here I am not complaining. We're lucky to even have this as an option. People are entitled if they want to complain...”

This is of course my own projection — I'm not in the heads of the Uber senior leadership team. But I did notice the CEO's reaction to the angry employee: “it is what it is.”

When I hear that phrase, I can almost see his shoulders shrugging, arms held up.

“It is what it is, it's not my problem...”

That's apathy — as we all know, the antithesis to empathy.

This is what employees reacted to. This is why employees were so angry. This is why someone leaked audio and memos around the meeting with CNBC: They felt this lack of empathy. They felt they weren’t being treated as people anymore.

Now of course, there are other factors beyond what I listed above that dictate how well your team receives you taking something away. For example, if you regularly are not treating your employees with respect, than no amount of giving choice is going to help.

Yet, Uber’s unfolding highlights an important reminder for all of us:

How we implement difficult changes matters as much as the changes themselves.

When leaders have to make painful decisions, the effort to minimize harm isn’t optional — it is the essence of leadership, itself. We must re-root in the humanity of our decisions as much as possible, and remember as leaders the degree of direct impact we have on the quality of other people’s lives.

Sure, we all want to avoid the negative PR that Uber is bearing. But, above all, I hope what we want most is to make sure we’re not causing undue harm to others.

Even when we have to take something away, we can still honor the humanity of the people we work alongside.

-Claire

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