The Best Managers Are A Little Paranoid
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Wow! Almost a year since my last post! Life has been full, but nearly 1,000 of you are still here (and counting). Thank you. My goal is to publish at least once a month from now on so the ride feels worth your time.
Now, back to business.
One of my favourite business books is Andy Grove’s classic “Only the Paranoid Survive”. The title is quoted so often in the corporate world it risks sounding like a motivational poster at this point, but Grove wasn’t trying to be cute. In the mid‑1980s, complacency almost wiped out Intel’s original business of memory chips. Facing brutal Japanese competition, Grove ignited a culture of productive paranoia that forced his team to ask, “If we were kicked out and the board hired a new CEO tomorrow, what would they do?”
That question led to the pivot into microprocessors that still defines Intel today. And while Intel is a much different company with an ever growing list of challenges, I always admired Grove’s initial viewpoint and it has stuck with me throughout my career. At its core, healthy paranoia swaps fear for a focused, disciplined alertness.
Many operators miss that memo, or maybe never were aware of it in the first place. Too often, I see project leads with unearned confidence run head first into avoidable errors, communication hiccups, and (worst of all) lost chances to improve. Fast‑moving markets, cross‑functional teams and AI‑accelerated competitors have only amplified Grove’s warning. Those that are ill-prepared to lead a landscape that’s constantly changing will be replaced with those that are.
After 15 years leading transformation programs, I’ve learned that the managers who outperform in turbulent environments share one common trait: they are constructively paranoid. They aren’t an overly anxious bunch or take pleasure in micromanagement. Instead they’ve built a disciplined habit of questioning received wisdom, including their own. Below are the five questions they ask most often. Apply them to any initiative you’re running today, and watch your odds of success climb.
1 . They Question “Best Practices”
Companies that are well run love codifying success with playbooks, SOPs and “centre of excellence” wikis. And while I’m a massive advocate for all of this, I know better than to take this information at face value. Especially in every situation. Every playbook is written at a moment in time, by people solving yesterday’s constraints with yesterday’s tool set.
Constructively paranoid managers interrogate that gap between current and optimal. They start by asking (with examples):
“Does this practice still solve the problem it was designed for?” A quarterly sprint ritual born in a waterfall era may strangle a team now shipping micro‑services weekly.
“Whose context generated this practice?” Tactics borrowed from a hyper‑growth SaaS firm can misfire in an asset‑heavy retailer.
“What happens if we invert the principle?” If a process assumes scarcity in generating an output, what would we do if those inputs became abundant?
Asking these questions often surfaces hidden costs such as delays, process variance, and other drags on real performance. Healthy paranoia turns those discoveries into measurable velocity.
2. They Question Themselves
Self‑doubt gets a bad rap in leadership literature, but private self‑interrogation builds public credibility. In an HBR study on high‑performing CEOs, researchers labeled this reflex productive paranoia—an ability to stay “hyper‑vigilant about what could hit and damage the business.”
Paranoid managers run an internal audit on three fronts:
Bias check. “Am I clinging to a decision because I made it?”
Capability check. “Am I truly the best person, by expertise alone, to lead this project, or should I empower someone with deeper mastery/experience?”
Rearview Mirror check. “Am I defaulting to an approach just because it worked for me before, or is it still the right fit for today’s context?”
Paranoid managers are comfortable questioning themselves, their past work and their direction before committing. More often than not, they come out well ahead of their over confident, under prepared counterparts.
3. They Question Historical Data
Dashboards that contain mostly lagging indicators offer a sense of comfort that the landscape has been identified and insights are ready to be uncovered. However, even the cleanest dataset is an outdated record of past conditions. Paranoid managers treat metrics as hypotheses, not absolutes:
Past vs Future. Revenue shows what already happened; early churn warnings show what’s coming next.
Missing Lessons. Tossing out “failed” experiments erases the clues that could save you later.
Data Goes Stale Fast. A sales forecast built on three‑year‑old, pre AI data can be wrong in just six months.
I’m ruthless with my own dashboards, rebuilding their structure at least once a month to be sure the story matches reality. When gaps appear, I redraw the picture.
Because when historical data collides with current reality, great managers side with reality first. Then fix the tool so it stays fit for purpose.
4. They Question Others (Respectfully)
Paranoia without empathy can be seen as pretty harsh. With empathy, however, it becomes due diligence. Elite managers scrutinize sources as carefully as statements. Here are some examples for you:
Incentives. A supplier praising “unprecedented lead‑time reduction” could be masking quality trade‑offs.
Expertise. A celebrated data‑scientist outside of his domain may wow the room with algorithms, yet miss critical criteria of the initiative, such as regulatory constraints. Reason being because they’ve never shipped a live product in that industry before.
Groupthink. The louder the consensus, the more they dig for disconfirming evidence.
Bill Gates famously kept a “could kill Microsoft” list in the 1990s, meeting weekly with small teams to stress‑test strategic threats. That ritual institutionalized skepticism without personalizing it.
By separating interrogation of ideas from judgment of people, managers build a culture where rigorous debate feels safe.
5. They Question Success Itself
Perhaps the most counter‑intuitive form of paranoia is scrutinizing your wins. Grove warned that “business success contains the seeds of its own destruction.” Paranoid managers take this to heart, treating every milestone as a snapshot and not the false sense of status. Some examples of wins that would have served a leader well to question:
Regression to the Mean. Yesterday’s record‑high sales could just be a one‑off spike; numbers usually slide back toward the average soon after.
Complacency Drift. A big win can make teams cling to the old playbook instead of upgrading it for the next challenge.
Competitor Magnetism. As soon as one product starts earning serious money, rivals rush in with look‑alikes to grab a slice of the pie.
A company I once worked with built a “Product Decay Review” into every post‑mortem. The team asked one blunt question: “If we shipped nothing new for 12 months, how would competitors chip away at this advantage?” That exercise exposed weak spots and led to additional investments in analytics UX optimizations. These moves helped them stay on top of an ever competitive industry.
Putting Paranoid Principles to Work
Healthy paranoia is both a mindset and a mechanism. Here’s how to put it to work in four quick habits:
Daily Doubt Check: Start each stand‑up with a 60‑second lightning round where everyone names one thing “we might be wrong about.” Capture every doubt, turn it into an assumption test, and park the outcome in the documentation of relevance (scope document, action log, risk register, etc.)
Two Source Rule: Pause before any material decision and verify the argument with at least two independent sources (data, experts, experiments, etc.) before you pull the trigger.
Deliberate Over Communication: Broadcast changes in scope, next steps, and likely impacts early and often. A flood of updates may annoy stakeholders, but silence can sink a project.
Mid Project Retros: Schedule a halfway checkpoint to interrogate early wins, expose emerging risks, and spot where reality is drifting from plan while there’s still time to “course correct”.
These micro‑rituals, once operationalized, help surface hidden risks fast, weave vigilance into routine, and keep your initiatives one step ahead of complacency.
The Payoff
I hope I’ve made a convincing case that constructively paranoid managers are the ones you want steering your most complex transformations in an endlessly disrupted world. Grove’s philosophy endures because it captures a powerful paradox: true confidence in leadership is anchored in the humility to doubt. The best managers channel that tension into relentless velocity. Constantly scanning, recalibrating, and staying one move ahead.
So the next time your team congratulates itself on a banner win, do what great managers do: smile, open a fresh page in your notebook, and write three words at the top:
“What could break?”
Then get to work.