Why Every Strong Team Needs A Challenger
The Invisible Tension within High Performing Teams
Episode 2 in the Dear First Born Son Series
Transcript
05-21-26
Dear Son,
I remember helping you make Scrappy the Robot when you were in Pre-K. Because I wasn’t about to buy store-bought supplies, I grabbed the baby, and you oldest kiddos headed to the garage with me to sort through the junk drawers.
You were skeptical about building a school project with discarded household items. In typical fashion, you were steps ahead in your questioning, challenging me with questions like, “what will happen if this . . . ” or “we gotta make sure of this, or else this . . “
Your mind was heading to the end of the project. You were building with the end in mind by identifying potential roadblocks during project planning. Just as you questioned me when I told you we were using scraps, I see that same instinct in you today.
As you head off to higher education and the corporate world, you will soon realize something important:
The people asking the hardest questions in the room are often the ones trying hardest to protect the future of the project.
I’ve seen it many times in my work, and have always appreciated the person bold enough (or maybe it’s brave enough) to speak up and question things.
For example, in complex website development and systems architecture projects, there is almost always an invisible tension inside the team dynamic.
Some people have the responsibility to make sure deadlines and budgets are met – all good things. They naturally take on the role of the protagonist—rallying the group, maintaining momentum, and pushing the project over the finish line.
Others on the team instinctively become the challenger.
The Challengers personality questions assumptions, seeking to identify risks, slow decisions down, and ask whether the current path actually solves the long-term problem.
In high-performing technical environments—especially those involving engineers, developers, data scientists, search visibility experts, content architects, finance experts, etc.—that role is often adopted by the most analytically minded people in the room.
Not because they enjoy conflict.
Because they understand the consequences.
But analytical thinkers are sometimes shut down and told to “stay aligned” with the project plan they have been handed, even when they can clearly see future risks forming.
When I was in college, we learned about this as “groupthink” — the tendency for groups to adopt ideas as true simply because the majority agrees with them. We were cautioned against accepting consensus without critical evaluation.
That lesson has stayed with me.
Strong teams need alignment, but they also need people willing to thoughtfully challenge assumptions before flawed decisions become expensive realities.
Challengers are usually the people asking uncomfortable questions that others really should not ignore for example, one might ask:
“What happens when this expands?”
“How will this affect crawl pathways?”
“Will this structure still work with 5,000 pages?”
“Are we solving the symptom or the system problem?”
“What technical debt are we creating?”
“What are we not considering yet?”
To fast-moving teams, this can feel like resistance. But in reality, these individuals are often performing preventative systems analysis in real time. They are identifying future operational failures before they become more costly.
That is not obstruction, it’s risk management.
Why Healthy Teams Need Both Personalities
The older I get, the more I realize healthy organizations need both personalities. They need people who create momentum, and people willing to challenge assumptions before momentum carries the team in the wrong direction.
The key is two-fold. First, we must learn how to hear the analytical challenger without mistaking thoughtful friction for negativity. Second, we must actually listen to the feedback and create a plan of action—either addressing the root cause or intentionally adjusting priorities while continuing to move the project forward. This can be difficult when everyone is scheduled for full steam ahead. That, though, is a topic for another day.
For now, understand that strong systems are rarely built by people who only ask how fast something can launch.
They are built by people willing to ask what happens next.
I encourage you to ponder the passage from Colossians 3:23 which says, “Whatever you do, work at it with all your heart, as working for the Lord, not for human masters.”
Wishing you the best today,
Love Mom
