The Chief Technology Officer leaned back in his chair with corporate confidence. “Our technology is actually in great shape,” he said.
From my seat across his glass-topped desk, I pulled up his company’s public-facing documentation — last updated in 2019, full of broken links and outdated processes.
I slid my tablet toward him. His confident smile faded.
This kind of honesty in interviews had become my retirement gift to myself — and, perhaps, to an industry in desperate need of a reality check.
Why I did this
In two months, I’m retiring after 30 years in corporate technology. I’ve saved enough to walk away. But before I go, I need to confirm something: is it just my current company making me want to leave, or is it corporate America entirely?
I suspect I already know the answer.
At my company, millions are spent on consultants who create polished PowerPoints about “digital transformation,” while our critical systems still run on aging, outdated software.
Leadership ignores warnings that our infrastructure is fragile. Middle managers are more focused on protecting their turf than actually collaborating.
I needed to know if this dysfunction was everywhere. And what better way to test it than by interviewing at different companies? With retirement weeks away, I had nothing to lose.
No more diplomatic answers. No more playing the game. Just raw, unfiltered truth.
Breaking the rules
My first candid interview was with a direct competitor. The meeting room’s floor-to-ceiling windows offered a sweeping view of downtown — a fitting backdrop for corporate theater.
When the recruiter asked why I wanted to leave my position, I ditched the usual “looking for new challenges” script.
“I’m frustrated by how leadership decisions impact long-term success,” I said. “The people actually doing the work raise concerns, but leadership prioritizes short-term wins. I’m curious whether this is just my company or if it’s common everywhere.”
The recruiter’s pen hovered mid-scrawl. His polished, friendly expression faltered.
After a beat, he redirected to my experience. When he described their technology as “cutting-edge,” I casually pointed out that their job listings were still asking for experience with a programming language that peaked in the 1980s.
“There’s nothing wrong with older systems,” I said. “But pretending they don’t exist? That’s where companies get into trouble.”
To my surprise, he nodded. “Fair point.”
Maybe honesty wasn’t a career death sentence after all.
The corporate buzzword machine
In my next interviews, I kept up the experiment.
Sitting in a sterile conference room decorated with motivational posters about “teamwork,” an executive asked about my leadership style.
“I don’t believe in corporate buzzwords,” I said. “You hear phrases like ‘servant leadership’ or ‘agility,’ but they often disguise the fact that decision-makers don’t actually understand the day-to-day work. Projects fail when people at the top make big decisions without real-world insight.”
The executive interviewing me leaned back in his chair. When I suggested we sketch out a system design together, he laughed.
Then he admitted that he hadn’t been hands-on with the work in over a decade. That led to an interesting discussion about the challenge of staying informed as a leader.
Later, in a dimly lit panel interview, someone asked about my biggest professional failure.
“We ignored system maintenance for years until everything crashed, costing us millions in lost revenue,” I said. “I flagged the risks, but leadership wanted to focus on new features instead. I’m curious — how does your company balance maintenance with innovation?”
Several panel members exchanged knowing glances. That was answer enough.
Salary transparency (or lack thereof)
Then came the compensation discussions — where my honesty experiment got really interesting.
In a bright corner office with Seattle’s rain-streaked skyline behind me, I asked a recruiter:
“What’s the actual salary range for this role? Not the initial offer range — the real ceiling?”
She hesitated, then set down her coffee cup. “Our listed range is $130,000 to $170,000, but we can go up to $190,000 for the right candidate.”
Amazing what happens when you ask directly.
I also pushed on pay equity. One company had recently completed a salary audit and admitted to a 12% gender pay gap they were working to fix. Another admitted they had never looked at the issue — but, after our conversation, they planned to.
“Creating leadership paths matters as much as pay equity,” I said. The VP of Engineering nodded and shared that they’d recently promoted two women to senior technical roles.
It wasn’t a fix, but at least they were aware.
What I Learned
By the time I wrapped up my last round of interviews, one thing was abundantly clear: the dysfunction that made me want to leave wasn’t unique. It was everywhere.
Even in the companies that seemed promising — the ones with real plans to modernize, or leadership that acknowledged their weaknesses — the same fundamental tensions existed.
The pressure to chase short-term wins at the expense of long-term health. The endless meetings where problems were talked about rather than solved. The reluctance to admit what wasn’t working until it was too late.
I realized that my entire career had been spent not just solving problems, but navigating corporate nonsense. The careful phrasing, the managing-up, the political games — these had taken as much energy as the actual work.
But what stood out the most? The relief I felt when I stopped pretending. For the first time, I spoke freely. I asked direct questions. I pointed out flaws without sugarcoating them. I challenged assumptions.
And instead of being dismissed, I was respected.
Three companies invited me for final rounds. A CEO spent two hours brainstorming governance improvements with me. A director of engineering admitted my questions about pay equity had inspired them to take action.
But despite the positive responses, I knew one thing for certain: I was done. Not just with my current company. Not just with interviewing.
I was done with corporate America.
The decision
My final interview took place in a modern office with panoramic mountain views. When asked about my five-year plan, I smiled.
“I’ll be retired — hiking those peaks instead of talking about them in interviews.”
The interviewer looked surprised, then thoughtful. “I envy your honesty,” she said quietly.
As I walked out of the building and into the crisp afternoon air, I let that truth settle over me. For years, I had convinced myself that my frustration came from specific leadership failures or poor decision-making. But the reality was bigger than that. The system itself — the endless meetings, the empty corporate jargon, the performative “transformation” efforts — wasn’t something I could fix.
And for the first time in my life, I didn’t want to fix it. As I reached my car, an unexpected feeling washed over me: freedom.
I sat there for a moment, watching other tech workers hurry into their glass towers, carrying their own unspoken truths. Perhaps my small experiment in radical honesty had planted some seeds of change.
Or perhaps not. But I knew one thing: my next challenge wouldn’t be climbing another corporate ladder — it would be climbing those distant peaks.
I had my answer.
