The Pragmatic Cheerleader
Leading with Grounded Enthusiasm
My parents owned, operated and worked in their hair salon from the time I was two. It was a window into the world of business as most kids walked home from school, I walked to the "shop" as we called it. My parents had their own styles of leadership that created a good balance. This was starkly evident after a pretty significant catastrophe.
In the tumultuous weather of the area, we had experienced a long period of sleet and rain. The ground became cold enough that a slush formed and clung to any surface the combination struck. So, heavier than snow and less likely to run off than plain rain. That concoction formed on the roof of my parents shop. And then we experienced a microburst.
A microburst is a short, intense downdraft. It's like all the air punches down at once. And it did so above my parents' business with devastating effects. We stood in the shop in coats around midnight looking up through the whole with water still pouring in and compounding the damage around us. Walls were ripped apart. Dryers, sinks and chairs bent beyond repair.
My dad went into his usual mode, pragmatism. I had a notepad writing down what he was seeing our next steps were. The short version is we'd have to completely rebuild and find another place to rent, cutting into profit while we're worked. And in this backdrop, my mother said, "Well good, this will give us the chance to redecorate."
What followed was incredulity, with a good bit of emotion. My takeaway, cheerleading is good but it needs the right conditions and context to be effective.
If you're a product owner, you are the team's "mini CEO", translator, tester and cheerleader. But to be successful, you need to ascend to being The Pragmatic Cheerleader. Let's discuss both aspects just in case it's not immediately apparent why the balance is key
Why "Cheerleader"?
At its core, cheerleading is about advocacy and visibility. A Product Owner must be the loudest advocate for the team’s wins, no matter how small.
Internal Advocacy: Ensuring the developers know why their work matters and celebrating the "invisible" victories, like a particularly elegant refactor or a successful bug squash.
External Advocacy: Defending the team’s capacity to stakeholders and highlighting the value delivered in every increment.
However, unlike a mascot who smiles regardless of the score, a pragmatic cheerleader’s enthusiasm is earned. It’s rooted in the belief that the team is capable of solving the problem, even if the current situation is difficult.
Why Pragmatic Enthusiasm
When you lead with sincerity rather than "corporate spin," you build three critical pillars of a healthy product culture:
Psychological Safety: Teams thrive when they know they won't be penalized for bringing up bad news. A pragmatic leader acknowledges the "suck" of a difficult sprint, which actually makes the subsequent praise feel authentic.
Sustainable Momentum: Toxic positivity leads to burnout because it asks people to pretend they aren't tired. Pragmatic cheerleading validates the effort, which helps sustain long-term energy.
Stakeholder Trust: When you are honest about risks and failures, your enthusiasm for a new feature or a successful launch carries ten times more weight. They believe you because you’ve proven you don't lie to make things look better.
Ways to be The Pragmatic Cheerleader
To adopt this mindset, consider these three tactical shifts:
Validate the Struggle, Then Plan Victory: Instead of saying, "Don't worry, we'll hit the deadline!", try: "This API integration is clearly more complex than we anticipated, and I know it's frustrating. Let's break down our best steps."
Celebrate "Smart Failures": If a feature didn't move the needle on your KPIs, don't ignore it. Cheer for the fact that the team built it efficiently and that you now have the data to pivot. The "win" is the knowledge gained.
The "Receipts-Based" Praise: Avoid vague compliments like "Good job, everyone." Instead, be specific: "This web site update lays the ground work for all our future improvements. It was hard fought but will be a game changer."
The Bottom Line: Smart, self-aware people reject toxic positivity. They want the truth. Think of Phoebe from Friends singing the "brutal truth" to kids—it’s refreshing because it’s real while focusing on action.
Some responses after a crashed sprint or project:
Toxic Positivity: "It’s no problem, just an opportunity!"
Cynicism: "Same story, different day."
Pragmatic Cheerleading: "This isn’t what we hoped for, but we have a path back to green. Let’s get to work."
Which one are you bringing to the team?
