The Toughest Cultural Shift We Ever Made and Why It Changed Everything

Jul 31
5 min read

We didn't rewrite a manual. We rewrote what we believed a “good month” looked like.

Let me ask you something before we get into it: have you ever built a business that was working (genuinely profitable, genuinely growing) and still had this nagging feeling that something underneath it wasn't right?

That was us. And it took an outsider holding up a mirror before we could even see what it was.

In 1990, there was a sudden end to the scheduled non-stop air service between Alaska and Hawaii. The scheduled air carrier that had been flying that route decided to drop it that spring. So John and I did something a little insane: we chartered our own jets. Not little private planes. Our first charter was with a DC8, operating about once a week, in the summer. The success of that first charter led to chartering wide-body jets like 767s and L-1011s. Our business was transformed from a small company selling package vacations to Hawaii to being a scheduled charter airline, carrying thousands of people a year between Anchorage and Honolulu. We operated much like a scheduled airline, but we were selling seats on chartered planes, which meant we paid the full cost of every flight, whether it flew full or empty. This was a huge risk!

But it worked. We were profitable. We were growing. But underneath that growth, we had unintentionally built a culture around squeezing every dollar we could out of each seat. Nobody sat down and chose that. It's just what happens when survival is the only goal anyone's asked to care about.

Our travel agents, our primary customers, started telling us they weren't happy with the level of service. Our employee turnover was higher than it should have been, which only made the service problems worse. Something had to give, and it wasn't going to be fixed by reorganizing an org chart.

Around that time, I went back to college (I'd dropped out at nineteen) to finish my degree at Alaska Pacific University, studying Organizational Management. Our business became my guinea pig. Everything I learned in class, I brought back to the office the next morning. Our managers used to visibly brace themselves whenever I walked in, because they knew exactly what was coming: “Guess what I learned last night?” And then we'd start implementing it. Immediately. No pilot program, no committee.

That's how Total Quality Management came to Hawaiian Vacations. The definition that stuck with me: integrating a quality-driven, customer-focused culture through continuous improvement and employee empowerment. I got so deep into it that I wrote my senior thesis on implementing a Total Quality Management program at our own company. This wasn't a corporate initiative handed down from someone else's playbook. It was personal.

Culture isn't something you find lying around your business. You build it, one decision at a time.

Here's the part that was genuinely hard: the old culture wasn't broken, exactly. It was working, by the only measure we'd ever used: revenue. Letting go of “maximize short-term profit, no matter the impression it leaves” and replacing it with a long-term, relationship-first view felt, honestly, a little reckless. We had to become customer-sensitive and responsive, quality-obsessed, and far more participative in how we managed people, instead of just telling them what to do.

That's the toughest cultural shift we ever made, not because the new values were complicated, but because it meant admitting the old ones, unspoken as they were, had been running the show the whole time.

Once we knew what kind of company we wanted to be, we had to name it: out loud, in writing, so nobody had to guess. We called ours the WERQ Ethic, an acronym my husband created.

Win-Win came first. Every relationship (team, guests, vendors, community) ran on the assumption that if the company won, everyone attached to it won too. And we didn't just believe it quietly. We celebrated every win. Loudly.

Efficiency meant real investment, not lip service. We spent two full years building a ground-breaking online reservations system, at a time when bookings still came in over the phone to an agent typing it into our in-house system by hand.

Responsibility looked like this: we trusted our people to act responsibly without someone standing over them, and responsibility also meant owning our mistakes out loud, apologizing, and fixing them, as a company and as individuals. That included taking our financial obligations to our employees, our guests, and our vendors seriously, every time.

And Quality had a definition so specific I can still recite it: a tan, happy guest stepping off the plane back in Anchorage, already looking forward to going back to Hawaii again, with Hawaiian Vacations. That was our Valuable Final Product (VFP). Not a number on a spreadsheet. A person's face.

None of this mattered as words on a poster. It only became real once we hired for it, rewarded it, and made decisions by it, even the uncomfortable ones. Leaders shape culture through what they reward, what they tolerate, and what they model, whether they mean to or not. We simply decided to do that on purpose instead of by accident.

Your business will get bought because you've built something that works

without you standing in the middle of it. Culture is what makes that possible.

When we look back at Hawaiian Vacations, which we owned for 25 years, the thing we're proudest of isn't the thousands of passengers flown on our chartered jets, or the balance sheet. It's the culture we intentionally nurtured. I'm convinced that if we hadn't poured that much attention into it, we never would have attracted the people who fueled our growth. We also never would have been in a position that made Alaska Airlines want to buy us.

Your Turn

Think of a company or team culture you genuinely admire. What specifically stands out about how people act there?
Write down three words for how you want people to feel the moment they walk into your business.
Be honest: what have you tolerated lately that quietly contradicts those three words?
Pick one guiding principle to anchor this quarter, and name one decision this week that proves you mean it.

Podcast Spotlight

All Things Retreat Podcast

I had the pleasure of joining Holly Porter on the All Things Retreat Podcast to talk about why retreats can be one of the most valuable investments a business owner makes.

We discuss what makes a retreat truly transformational, the common mistakes to avoid, and why creating space to step away from your business often helps you move it forward.

🎙️ Listen Here: Transformational Retreats: A Guide for Entrepreneurs

Final Thoughts

I still think about how uncomfortable it was to admit that a profitable, growing company could be running on a culture we'd never actually chosen. But that discomfort is exactly the signal. If you can't name the values steering your business right now, another set already is.

Ral West

Livin' the Dream