One of the biggest mistakes I’ve made as a leader was losing the ability to hear honest feedback under the pressure of high stakes deadline.
I somehow assumed that when external expectations were tight, the team must prioritize relentless efficiency above everything else.
I’ll give you an example.
In early 2020 I was tasked with building a new analytics department from scratch. The company was investing a lot of money in data and analytics resources in order to support a major initiative. Our new, small team was still trying to find its footing when the pandemic hit. The external pressure to deliver the promised results was already high, and the sudden shift to remote work just compounded it.
The shortcut I made was to save on social interaction, cut down on communication to “just the facts”, skip team-building, and focus strictly on hitting deliverables.
The result? We launched the product on time.
But there was a bunch of information that got left out of the internal review.
The team was worn out, key specialists were looking at quitting, and, as I later discovered, several critical bugs were swept under the rug because nobody felt safe enough to admit they existed.
The project itself wasn’t a failure. It was just incomplete.
To be clear, hitting the deadline is essential! But ignoring the people infrastructure required to do it is a massive lapse of judgment.
Seeking comfort in control
When you read social media or online articles, you often get the impression that high stakes require leaders to be extremely prescriptive and direct. It’s all about the tough talk:
"I am setting a zero-tolerance policy for errors!"
"We need 12-hour days until this is done!"
"You should only bring me solutions, not problems!"
"We can talk about feelings next quarter!"
I can admit, not everything is wrong with that. Sometimes, a firm hand and clear direction is necessary.
But behind a lot of these high-pressure, “successful” deliveries are hidden costs: key staff turnover that kills institutional memory, technical debt that cripples the next iteration, and a pervasive culture of fear that ensures errors are hidden, instead of being solved.
I’m not suggesting these leaders are evil or intentionally malicious. My instinct is to always assume they simply believe they are pushing the team to greatness.
But the narrative doesn’t account for all of the projects that were delivered on time, only to crumble six months later because the internal structure was fundamentally broken.
The real cost
Selective attention creates an incomplete picture of how delivery really happens.
And for every leader who drove the team hard, demanded impossible hours, and delivered the product - there are hundreds who did the same thing, and ended up with a toxic team that imploded before the next project started.
But of course, those stories don’t make it into the Linkedin post or case studies. Those people don’t get to speak at conferences about their “incredible” project management skills.
When I started managing high-pressure projects, I almost fell for the selective focus. I started modeling my behavior after the "tough CEO" until I learned the full story: those results were delivered by teams that had been together for a decade, had established internal language, and possessed an unspoken level of trust built over years.
That doesn’t mean the CEO was wrong. He was (and still is) an excellent leader. But his style wasn't right for my new, fragmented team under immediate pressure.
High-stakes delivery requires more safety, not less. The more I study this, the more I realize that treating psychological safety as a luxury you save on in crunch time is a very bad idea.
What works for me
Instead of trying to copy other people’s “pressure tactics,” here’s what works better for me when the deadline is breathing down my neck: I focus on increasing internal safety, not forcing sacrifice.
When the margin for error shrinks, the requirement for honest, immediate feedback goes up exponentially. Now, I always try to find ways to create small moments of safety.
And don’t forget to pay attention to silence! When people fail to flag risks, that’s important information too. It means there’s more to the story than what the project charts are showing.
What works for a stable team with five years of history might fail completely for a lean, newly assembled group trying to hit a milestone. Your team’s history matters and you should always be cognizant of that.
Now, the intention of this lesson isn’t to get you to treat every project as a hand-holding exercise. Leadership in crunch time is hard, even when you have high trust.
But leaders who choose to preserve internal clarity and honest dialogue when the external pressure mounts are the ones who build durable systems. Trust is a critical input for high performance, not a side benefit.
So, the next time you feel the clock ticking down, I hope you’ll remember that your job isn't to force speed, but it's to ensure the communication lines stay open enough to catch the problems before they become catastrophes.
I hope this resonated.
See you next Tuesday.