The Night the Tire Blew:
There’s a strange clarity that hits you on the shoulder of an interstate at night.
Headlights streak past, the air vibrates with passing trucks, and you’re suddenly aware of how little control you really have.
Recently, a large metal object on the road punctured my tire. One second everything was normal; the next, I was coasting to the shoulder with hazard lights blinking. I wasn’t expecting an emergency. But I was prepared for one.
And as I worked through the steps — jack, spare, flashlight, calm — I realized something that applies far beyond the highway:
Disasters don’t arrive on our schedule.
But our ability to respond does.
That distinction is at the heart of one of the biggest leadership blind spots in technology today: confirmation bias — the tendency to believe that because something hasn’t failed yet, it won’t fail in the future.
We Prepare for What We Expect — Not What’s Likely
No one drives thinking, “Tonight’s the night my tire blows.”
We simply assume the drive will go fine because it always has.
That assumption is comfortable. It’s familiar. And it’s dangerous.
When my tire blew, I didn’t panic. Why? Not because I predicted it, but because I had already built the plan for it.
Preparation isn’t prediction. Preparation is the expectation of uncertainty. In business, especially in technology leadership, this distinction determines whether an organization weathers a crisis or becomes the next cautionary tale.
The Boardroom Version of a Highway Blowout
Every week, I meet with decision-makers who unknowingly run their organizations with that same “it probably won’t happen” mindset.
Most leaders don’t say it aloud, but they think:
- “We’ve used this system for years — it’s fine.”
- “Our antivirus has always worked.”
- “We’ve never been hacked.”
- “We’ll patch it later.”
- “Upgrades aren’t urgent.”
These statements feel rational because nothing bad has happened yet. But that’s the trap. Past success is not evidence of future safety. It’s merely the absence of an incident — so far.
Confirmation Bias: The Quiet Risk
Confirmation bias doesn’t announce itself. It hides behind experience, familiarity, and comfort. It whispers:
- “If it were a risk, something would’ve gone wrong already.”
- “We’ve always done it this way.”
- “It’s probably good enough.”
But this bias blinds leaders to risks that are already accumulating:
- End-of-life systems that are one failure away from catastrophe
- Unpatched servers exposed to known vulnerabilities
- Outdated antivirus that no longer catches modern attacks
- Backups that haven’t been tested in years
- Firewalls running software from a decade ago
Each of these can create an “interstate moment” — abrupt, costly, and entirely avoidable.
Why Smart People Fall Into This Trap
Intelligent leaders aren’t careless. They’re human. And humans are wired to misjudge risk in predictable ways:
- Familiar systems feel safe — even when they aren’t. Comfort becomes a substitute for evidence.
- No incidents equals perceived security. But “nothing happened” often just means, “nothing happened… yet.”
- Upgrades feel discretionary until disaster hits. Then they instantly become mandatory — and far more expensive.
- Low-probability, high-impact events are hard to emotionally visualize. So leaders under-prepare for them.
This is exactly why confirmation bias is so dangerous: it gives leaders the illusion of safety while vulnerabilities quietly grow beneath the surface.
Challenging Assumptions the Right Way
At Electronic Office, our role is not to sell technology. It’s to help organizations confront the uncomfortable truths that confirmation bias hides. We operate as Trusted Technology Advisors, which means we prioritize:
Understanding the business: The pressures, the people, the mission, the regulatory environment.
Building relationships: So we can tell you the truth — even when it’s inconvenient.
Delivering predictable outcomes: Because consistency is the antidote to blind spots.
Questioning assumptions with data: Not fear. Not pressure. Not guesswork. Evidence. The real work isn’t installing tools. It’s using expertise, process, and accountability to ensure the tools achieve the outcomes leaders expect.
Tools matter.
Processes matter.
People matter more.
Because a firewall isn’t valuable if no one is managing it. A backup isn’t valuable if no one is testing it. A monitoring system isn’t valuable if no one is responding to alerts. Preparation is not something you buy. It’s something you build — with the right partner.
Hope Is Not a Strategy
Too many organizations quietly operate on hope:
- “I hope we never get hit by ransomware.”
- “I hope our old server holds on another year.”
- “I hope nobody clicks the wrong email.”
- “I hope our backups work if we need them.”
Hope feels good. Until it’s replaced by regret. Preparation isn’t about predicting threats. It’s about ensuring resilience regardless of the threat. When the blowout happens — and eventually, something always does — the question is simple: Are you surprised? Or are you ready?
A Leader’s Blind Spots Cannot Be Self-Identified
This is the hardest truth for executives: You cannot see your own blind spots. By definition.
That’s why the most resilient organizations invest in outside perspective — not to replace their internal teams, but to strengthen them. A good advisor doesn’t just point out risks. They help design:
- Modern tools aligned to real threats
- Operational processes that prevent drift
- Governance standards that ensure consistency
- Monitoring and response plans that actually work
- Roadmaps that prevent the “surprise emergency” every organization fears
When a leader embraces this, resilience becomes predictable.
What Decision-Makers Should Ask Themselves Today
Here are the questions that challenge confirmation bias head-on:
- What outdated system are we tolerating simply because it hasn’t failed yet?
- What assumptions are we treating as facts?
- Where are we underestimating risk because we haven’t experienced pain?
- If our most critical system failed tonight, what would we wish we had done differently?
- Who is helping us see what we cannot see ourselves?
If even one of these questions stings, it’s a signal — not a problem.
The Real Lesson From the Interstate
Standing on the shoulder of the road, tightening the last lug nut, I wasn’t thinking about the metal that tore my tire. I was thinking about preparation — the quiet discipline that transforms a crisis into a manageable inconvenience.
I avoided disaster not because I was lucky. I avoided it because I was ready. Your organization deserves that same confidence. Not confidence in luck. Not confidence in the past. Confidence in preparation.
Because the unexpected will happen:
- A system will fail
- A cyberattack will strike
- A staff member will click something they shouldn’t
- A backup will be needed
- A critical component will reach end-of-life
- A new threat will bypass outdated defenses
The question isn’t if. It’s when — and how prepared you’ll be when it happens. At Electronic Office, this is why we exist:
- To help leaders challenge their biases.
- To help teams see their blind spots.
- To build processes that hold up under stress.
- To ensure that when the unexpected comes — and it always does — your organization stays on the road and moving forward.
Preparation isn’t a tire-changing kit. It’s a mindset. And the organizations who embrace it will not only survive uncertainty — they’ll thrive in it.
