Good Morfternight, this is Paolo with the 107th issue of our newsletter on Product Management, Distributed Leadership, and the Edge of Tech. Over 8,500 people read it every week. I hope you’ll join us for today’s read.
The Delicate Question
What should you do when the CEO asks you to do something?
That’s the delicate question.
For most people, this is a no-brainer. The CEO asks, you get your team together, and you execute.
Yes, but let’s consider common scenarios where:
The request is not on the roadmap.
The request does not align with the current strategy.
The team morale would be hurt by a last-minute change of plans.
The team is at max capacity and will have to drop something to execute.
Now you can see how the question becomes, indeed, quite delicate.
Over time, I have developed a set of principles to manage this type of situation.
I’m happy to share them, of course, but first, let me tell you a personal anecdote to make it even more tangible.
Many Moons Ago…
I was leading a team developing a “social login” functionality. At the time, it was quite a new thing, and we were excited to ship it.
We did extensive research and discovered that Facebook wasn’t just the most popular social network, but their users broadly overlapped with our service. Naturally, my team and I decided to prioritize the “Sign in with Facebook” functionality over other options.
Just as we were about to start working on it, I got a ping from my boss.
“You need to start with Google.” No other explanation.
A five-minute conversation that completely overturned the work done by my team and the decisions we had agreed on.
At this point in my career, it wasn’t the first time something like this had happened to me. Although no specific reason was mentioned, I had a hunch the change in priority might serve some partnership discussion I had no context about.
In my early days, I would have just gone to the team and said, “Our CEO told us to change X. I know it sucks, but we have to get it done. OK?”
After all, what’s the problem? A company’s CEO can surely make such decisions.
But doing this impactsteam morale, and their perception of me, not as their leader, but as a conduit carrying orders from the top.
So I decided to do something different.
I embraced the idea of starting with Google instead of Facebook as my own. I studied the merits of the idea with a neutral mind, found the benefits we had previously overlooked, and built a compelling case for the team.
In presenting my conclusions, I never mentioned the CEO’s input, but I highlighted all the things I learned by adopting the idea as my own:
Facebook users were less likely to use any other sharing platforms.
Facebook users didn’t get any benefit beyond an easy login.
Google users, on the other hand, were more likely to use multiple platforms.
Google suite of products had other integrations with ours that connecting accounts enabled.
I convinced the team and got their support for the change of plans.
Team? Happy. Boss? Satisfied.
And my reputation as a team lead grew stronger.
Principle
If you can’t sell it as your own, it’s time to manage up and push against your boss.
When your boss asks you to do something that doesn’t seem to fit your roadmap, you should adopt the idea as your own, find all the relevant merits, and pitch it to your team without ever mentioning the origin of the request.
If you can’t present the idea to your team with a straight face because there are no observable merits to it, then that’s your signal to go back to the CEO and push back.
Adopting an idea as your own is the best way to test its quality.
FAQ
Why can’t I disagree and commit?
“Disagree and commit” is a principle, originally popularized by Jeff Bezos at Amazon, following which, while peers are encouraged to passionately debate which direction to take without holding back, once a decision is made, it is imperative that everyone in the room commits to its success, regardless of whether they originally agreed with it or not.
It implies that if I disagree and commit to a decision, I will not broadcast my disagreement to my teams, as that would most likely jeopardize my chances to get them behind the idea or project.
It also implies that there has been a debate about the idea where all sides of the argument have been presented, which is a different situation than the type of direct order I am referring to.
If my CEO told me to do something, how can I push back?
There is an asymmetry—we tend to consider any decision coming from the top as absolute. By not thinking about it critically, you may end up causing giant problems down the road. You will be amazed at how many “five-minute requests” from CEOs have created 20 months of useless work for their teams. You are paid to think clearly, spot concerns, and communicate them to your boss.
Isn’t this like stealing someone’s idea?
I don’t think so. Optimizing for efficiency in a company implies that ideas can come from anywhere, and at the end of the day, credit goes to the teams executing, not to the people leading them or whoever expressed the idea first.
In addition, work starts with an idea that is progressively refined and polished through feedback, testing, and iteration. Ideally, by the time it’s shipped, everyone has contributed something and the ownership of the original ideas is barely traceable.
Meanwhile in San Vito lo Capo…
When I’m not product managing, I enjoy black and white photography.
Here is a picture I took recently in San Vito lo Capo during a weekend with friends.
That’s it for today. Thank you for being a Morfternighter. If someone forwarded this to you, I also write and publish my photos on paolo.blog.
Cheers,
P.S.: If you enjoyed reading this, please don’t hesitate to share it.
Good Morfternight, this is Paolo with the 107th issue of our newsletter on Product Management, Distributed Leadership, and the Edge of Tech.
The Delicate Question
Many Moons Ago…
Principle
Meanwhile in San Vito lo Capo…
