Eleven Pivotal Questions Every Team Should Discuss
Ask these to make you & your team shine

Katrine Tjoelsen
March 07, 2023

Hey, fellow learner — today’s about a crucial skill:
Asking the right question at the right time.
What use is your effort, or your team’s effort, if it’s focused on the wrong thing?
Most others operate within the status quo. They assume that implicit goals and assumptions are valid. They’re afraid of asking dumb questions.
But if you master the art of questions, both you and your team will shine.
Try these in your next meeting:
Pivotal Questions
🎯 Focus on the right goal
We can sprint from point A to point B, but it doesn’t matter if we should be going to point C. Ask:
“What is our ultimate objective?” If the initial answer is a task or a near-term stepping stone, ask: “Toward what end?”
“Which criteria are we using?” We talk past each other when debating what to do without the same criteria in mind.
“What are we optimizing for?” Optimizing for customer retention is different than optimizing for new sales.

🖐️ Generate enough alternatives
Our decisions fail if we’re considering the wrong set of alternatives. Ask:
“Can we come up with just 3 more ideas?” To have great ideas, we need many ideas.
“What if we did the opposite?” A question from Tim Ferris that helps us get out of our status quo bias.
“Can we fire bullets instead of cannonballs?” We falsely believe we must choose between huge bets. Often, we can run cheap experiments to learn more.
First, you fire bullets (low-cost, low-risk, low-distraction experiments) to figure out what will work—calibrating your line of sight by taking small shots. Then, once you have empirical validation, you fire a cannonball (concentrating resources into a big bet) on the calibrated line of sight. Calibrated cannonballs correlate with outsized results; uncalibrated cannonballs correlate with disaster. The ability to turn small proven ideas (bullets) into huge hits (cannonballs) counts more than the sheer amount of pure innovation.
🔬 Assess and gather evidence
Too often we act as if we have more evidence than we actually do. Ask:
“What are facts and what are assumptions?” Try drawing a line on the whiteboard and work with your team to put facts on one side, assumptions on the other.
“Which data would make you change your mind?” If data can’t change someone’s mind, they’re dogmatic rather than scientific. The same goes for you ;)
“What have we tested?” Often this reveals that we haven’t tested enough. And sometimes we realize the evidence is in front of us.
🚀 Change the game
When we’re stuck, it helps to see things differently. Ask:
“What is the worst thing that can happen?” Check if you’re held back by fear. Assess how real that fear is.
“Who could help us?” A 10-minute conversation can unlock more progress than 10 hours of meetings.
“What one thing would make everything else easy?” For a startup, perhaps it’s that one reference customer? Or that one key hire?
What else?
A book I’m reading: Ideaflow by Jeremy Utley and Perry Klebahn. This book, and a startup accelerator I participated in ran by Jeremy and Perry, prompted many of the ideas in this newsletter.
More questions: Check out these powerful questions from the Co-Active Training Institute.
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