Chicago-based friends! I’m traveling to speak at ProductTank Chicago on June 12th. It would be fun to meet in person. I believe the event is free.
Here's a pattern that has always fascinated me.
In 1:1 conversations, front-line teams say they're overwhelmed and juggling too many balls.
Eventually, a leader will at least entertain the idea that teams are trying to do too many things. They might even say, "It seems like we're trying to do too much. Are we?"
They ask middle or upper-middle managers: "So what can you cut?"
In response, those managers say, "Nothing. We don't need to cut anything."
It can go around in circles like this for a long time. The leader gets more and more confused. What's real? Every time they leave the door open for more focus, no one wants to walk through it. Meanwhile, other channels (like engagement surveys, informal discussions, etc.) tell a different story.
A couple of explanations come to mind.
Trick Question
Often, leaders are out of touch with the incentive structure they've fostered in the company. The upper-middle managers are weary. History tells a story that doesn't fit with the newfound desire to focus. A director friend explained recently, "It feels like a trick question—because if I mention we should pause something, I worry we'll just go back to trying to figure out how to do everything. Or worse, they'll ask me why we need our current headcount."
No Clear Winners
The next potential culprit is the "no clear winner" problem. Sometimes, there aren't any obvious winners (just a handful of uncertain bets). And you still need to keep the cash cow going. So, instead of narrowing focus, you try to keep the existing thing alive and explore every possible option that might eventually take its place.
Upper-middle managers are stuck in the same trap as everyone else. Their incentives, goals, and perceived safety are all tied to keeping everything in motion. If no one at the top backs a pause (or truly absorbs the risk of focus), it's no surprise that nothing changes.
Nothing You Can Drop
Sometimes, the problem isn't too many formal priorities. On paper, the list might look reasonable. But in the real world, teams are navigating years of accumulated debt. Unless someone says, "This is it! We're working down that debt. We're truly doubling down on platform work," there's no room to maneuver. There's nothing you can just "drop."
Escalation Games
The final scenario is this: the upper-middle manager is experiencing the same thing with their reports. They hear complaints about too much work in progress. They ask about it. The managers say it's fine. And the cycle repeats—for all the same reasons listed above.
With all this in mind, what can you do?
You must ensure your team understands it is not a trick question and that you are not fishing.
Trust the front lines, and give your managers a break. The front-line folks are likely telling it like it is. We have just walked through all the weird dynamics in the messy middle.
Look closely at whether you are dealing with a "no clear winner" problem. You must make hard choices if you are unwilling to burn resources on endless ball juggling. That might mean laser-focusing on one future bet at a time instead of trying them all.
And if you think, "I am giving feedback, but my managers act like it is not a real issue," know that there is probably more at play. Focus on what it feels like to get work done, not just broad statements about priorities.
Some fun things you might be interested in:
…and a talk I did at the Swarmia conference on your operating system as a design problem.
This isn’t misalignment. It’s a networking flywheel of dysfunction:
- Teams scream overload
- Middle says “we’re good”
- Execs ask what to cut
- Everyone panics, says nothing
- New dashboard launched to track the silence
It’s alignment theater. With jazz hands.
Something I've done successfully with a "managing up" approach is that when my superiors tell me that everything is all equally Urgent, Important, and Top Priority, I take a look at all of it myself, and report to them, in a document, the priorities that I will be working.
If they will not set the priorities, I will.
Usually, at that point, they do actually talk with me about their actual priorities.
I've heard from others who do this and *deliberately* say they'll pursue an *obviously bad* priority order. I wouldn't, as (1) I don't want to appear incompetent, and (2) they might just (either blindly or maliciously) approve the bad priorities, and then I'd have to live (and die) with them!
Also, when they crash in with emergencies, I update the priorities to put that on top, showing how everything else has moved down. They object, of course. But unless they have something more to say than, "You can't do that! We have to have it all, now, equally!!!" then I'm not listening.