Challenger Selling and Power Questions: How Big Problems Actually Get Solved
If you’re trying to solve small problems, you can be polite and agreeable and still win.
If you’re trying to solve big problems—behavior change, systemic inefficiency, billion-dollar health outcomes—agreement isn’t enough. Big problems require new thinking, and new thinking requires tension.
That’s why The Challenger Sale and Power Questions resonated with me. It’s not about being a jerk. It’s about being useful enough to challenge the status quo.
The trap: surface-level conversations
Most discovery calls and leadership meetings stay shallow:
“What are your goals?”
“What’s your budget?”
“What are your challenges?”
Fine, but it’s the stuff people say on autopilot.
Big change happens when you ask questions that force clarity and dive deep below the surface.
Power questions that create movement
Here are five categories I lean on:
1) Status quo disruptors
“What happens if you change nothing?”
“What’s the cost of staying exactly like this for 12 more months?”
2) Root-cause questions
“Why is that happening?”
“What have you tried already—and what did you learn?”
3) Tradeoff questions
“What are you willing to stop doing to make room for this?” Start, Stop, Continue
“Which metric are we willing to sacrifice to win the one that matters most?”
4) Decision-clarity questions
“What would need to be true for you to move forward?”
“Who has to believe this for it to stick?”
5) Ownership questions
“What part of this is on you?”
“What’s the first commitment you’re willing to make?”
These questions aren’t comfortable. That’s why they work.
Why this matters in startups
Startups live and die by learning speed.
If you can’t challenge assumptions, you can’t learn.
If you can’t learn, you can’t adapt.
If you can’t adapt, you lose.
This approach helped shape how I think about solving huge problems—from education outcomes and higher ed career services to tackling root-cause health and the obesity crisis.
A simple Challenger structure you can steal
Lead with an insight (something true they haven’t fully internalized)
Ask a question that creates tension
Offer a path forward (clear next step)
Example:
Insight: “Most new programs don’t fail because people don’t care. They fail because behavior change isn’t designed.”
Tension question: “If your process stays the same, what changes… really?”
Path: “Let’s pick one lever, measure it weekly, and redesign around adherence.”
If your messaging is polite but not persuasive, you probably need better questions—because better questions create better thinking.
