How Insatiable Questioning Disrupts Stagnant Systems and Sparks Breakthroughs

Medium - Requires some preparation Recommended

An Israeli tech firm faced declining productivity and growing customer complaints, yet middle managers hesitated to change a rigid, decade-old project tracking system. Enter Tamar, a 23-year-old recent hire, who noticed that hours were wasted on double entry. In the weekly review, rather than staying silent, Tamar publicly questioned if the current model was truly the best fit or just inherited habit. She outlined an alternative using a cloud-based tool, provided supporting stats from similar companies, and acknowledged that switching would involve growing pains.

At first, her candor unsettled her boss, who wasn’t used to such directness from someone so new. But soon, other staff joined the debate—some half-defending the old way, others riffing on Tamar’s improvements. What began as contention grew into a shared problem-solving session, ending with a pilot test of both systems. Within two months, the team found a substantial drop in wasted time, and a survey showed staff felt more empowered to speak up.

That small act of 'chutzpah,' or bold questioning, proved crucial. In Israel, this phenomenon is not limited to tech firms. The same assertiveness shows up in classrooms, military units, even city government. Repeated studies have shown that complex systems—organizations with flexibility and channels for questioning—adapt faster and outperform those that value rigid compliance over creative dissent.

Commit to making your next challenge a spark for good trouble. Pick one process that you honestly believe could work better, and gather real evidence or workable alternatives for your suggestion. Don't keep it to yourself: bring it into the open—in a group, a message, or even a hallway chat. If you're nervous, remember that real breakthroughs start with discomfort. Ask for sincere feedback, listen for counterarguments, and let the discussion shape better solutions. Give it a go this week, and let questions, not silence, drive your next step.

What You'll Achieve

You’ll strengthen your self-confidence and foster a more dynamic, engaged team. Teams that cultivate purposeful dissent surface valuable insights, avoid groupthink, and boost their odds of breakthrough solutions.

Challenge Authority with Purpose in Your Next Meeting

1

Pick a rule or method in your workplace or classroom you genuinely disagree with.

Identify a policy or process that seems arbitrary, outdated, or less effective than it could be.

2

Develop at least one alternative, supported by evidence.

Clarify your proposal using specific facts: maybe a friend's success, a case study, or a relevant experiment. Anticipate counterarguments.

3

Voice your position clearly at the next opportunity.

Speak up in a group or to a decision-maker in a constructive, confident tone. If it’s tough to do in real time, write an email or a short memo.

4

Invite feedback and encourage others to weigh in.

Don’t just present your idea—ask for questions and criticism. Treat dissent as a signal you’re doing it right.

Reflection Questions

  • What worries or anxieties do I have when it comes to challenging authority?
  • How can I frame my dissent so it invites real discussion rather than conflict?
  • What environment helps me feel safe to raise bold questions?
  • How would my group be different if everyone contributed one challenge a month?

Personalization Tips

  • If your family always follows the same vacation routines, propose a new travel plan and defend your reasoning at dinner.
  • During team meetings, question whether a long-standing task really adds value, and suggest a more efficient process.
Start-up Nation: The Story of Israel's Economic Miracle
← Back to Book

Start-up Nation: The Story of Israel's Economic Miracle

Dan Senor
Insight 2 of 8

Ready to Take Action?

Get the Mentorist app and turn insights like these into daily habits.