AINsight: Retention Starts with the Right Match

Every hiring match begins with hope. Employers hope to find the right person who will strengthen their team. Candidates hope to find a place where they can grow and belong. Yet too often, that shared hope turns transactional instead of personal.

After nearly 25 years as a career “matchmaker,” I’ve learned that hiring isn’t about résumés or job titles. It’s about alignment between values, communication, and expectations. When that alignment is missing, even the most qualified hire won’t stay long.

That belief shaped a recent conversation I co-led with my colleague, Jennifer Pickerel, at NBAA-BACE 2025 titled “Navigating Careers & Culture.” We were joined by two respected aviation directors from Part 91 flight departments: Jay Orwin and Steve Saflin. Both are hiring managers who have also been job seekers within the past five years. Their dual perspectives brought candor and balance.

Together, we explored how every stage of the hiring process—from defining a role to onboarding—shapes retention. As we told the audience, “Retention starts at the very beginning.” It begins with clarity about what you want, what you offer, and how you show up in the process.

Of course, there’s no one-size-fits-all approach to hiring or retention. Each organization’s process looks different depending on its size, structure, and resources. Some have dedicated HR teams, while others rely on department leaders, peers, or outside recruiters. Whatever the scale, the goal remains the same: to create an authentic match that lasts.

Know Why You’re Looking

Every search begins with a story. For an employer, the first question should be simple: why does this opening exist now? Is it retirement, promotion, or something more concerning? If turnover or misalignment caused the vacancy, address those issues before posting. Otherwise, the cycle will repeat.

For candidates, self-awareness matters just as much. Jennifer reminded us, “An astute candidate will always ask, ‘Why is there an opening?’” She encouraged professionals to be equally intentional. Why are you looking? Is it stability, a shift in priorities, or a desire for growth?

Jay added that departures are rarely about aircraft or type ratings. “Nine times out of 10, someone is leaving because they’re not meshing well with your company culture,” he said.

Steve agreed: “It’s all about the fit. When you’re assessing whether you belong somewhere, look at everything that matters to you—the equipment, the schedule, the compensation, and the stability of the company. At the same time, make sure the company aligns with your own ideals, just as they’re evaluating whether you fit theirs. When those things come together, you’re off to a pretty good start.”

Whether you’re leading a department or exploring your next step, it helps to pause and reflect before acting. Reflection keeps that initial hope grounded in reality and sets the stage for success.

Be Intentional

Once you understand why you’re hiring or searching, define what you need. “Each and every job search that you do should be intentional,” I told the audience. Resist the temptation to recycle an old job description. Departments evolve, teams shift, and strategies change. Take time to refresh your requirements before posting.

Candidates should do the same. Motivations evolve throughout a career. Jennifer explained, “We ask every candidate to identify and rank four motivating factors.” As she put it, “If you don’t know where you’re going, any road will do.” That exercise helps clarify what matters most—whether it’s advancement, stability, balance, or culture.

Steve added, “What suited you at one point in life may change. There’s always a right fit for a company and a right fit for a person.”

It takes honesty to revisit your goals and courage to admit they’ve changed. Once both sides understand their motivations, the next challenge is communicating those priorities clearly—to the market and to each other.

Control the Message

An organization’s external message shapes how candidates perceive its culture. The same principle applies to individuals seeking their next opportunity. In business aviation, reputation travels fast—and often farther than you think.

For some companies, especially smaller flight departments, every hire feels personal. For others with dedicated recruiting teams, the process may be more formal. Either way, perception matters.

I reminded the audience that once a job posting appears online, it can take on a life of its own. “If your reputation needs repair, take time to address it before posting, or consider not posting at all,” I said. “It will go to a chat room. And we all know of places where organizations have been vilified on social media—whether they don’t pay enough, there’s no time off, or people say the culture isn’t great. Even if it’s not true, that can do terrible damage in attracting talent.”

Jennifer agreed: “We know this is a small industry, and sadly, human nature tells us that bad news travels quicker than good news. As a candidate, I might look at a hiring organization and think, ‘They’ve had a lot of turnover’ or ‘They’ve had that job posted for a long time.’”

Her advice to employers is simple: be intentional about why you have an open position. And if something has gone awry with your public image, acknowledge it and show what’s changed.

From the candidate’s side, she added, “You have to turn your light on.” That might mean quietly letting a trusted circle know you’re open to new opportunities rather than announcing it publicly. In an industry built on discretion and trust, subtle signals often speak the loudest.

Interview with Intention

Whether you’re evaluating 10 applicants or two finalists, structure helps level the playing field. “Put together a scorecard and rank each of the candidates,” I advised. List the traits and skills you need, weight them by importance, and score objectively. It helps eliminate bias and keeps everyone focused on what matters most.

Jennifer suggested that candidates mirror the same process. “When both parties evaluate fit against their priorities instead of gut instinct, alignment improves and mismatches shrink,” she said.

The prescreening stage often exposes a gap between HR and aviation. Not every flight department has a recruiter who speaks aviation, and that’s okay. What matters is closing the communication gap early.

Jennifer told candidates, “Don’t let that rebuff you. Instead, use that conversation to learn how aviation fits within the enterprise.”

Jay agreed that employers can do better. “Having a strong relationship with your internal recruiting team is a necessity,” he said. If HR doesn’t understand the operation, bridge that gap. The first impression between company and candidate should reflect professionalism, not confusion.

As for interviews, I always want to know why a candidate wants the job. “I want to know why you think you’ll be a good fit for me,” I said. Intent matters. One aviation director summed it up best: he wants people “running to” the role, not “running away” from something else.

The best interviews reveal both competence and culture fit. When both sides are transparent about what they need, the conversation becomes a partnership, not an evaluation.

Seek Clarity and Build Trust

Few moments define an employment relationship like the offer. Surprises here damage trust. “The first thing we do for an employee is make them an offer letter, and we don’t want them to be disappointed,” Steve said. “If that’s where we start, we’ve failed.”

Jennifer encouraged candidates to advocate professionally. “You need to be able to explain and articulate your value with data,” she said. A thoughtful counter supported by facts feels collaborative, not confrontational.

Every department will handle the offer process differently. Some have formal compensation bands, while others are more flexible. Either way, clarity reduces frustration and builds confidence.

Jay explained that his company’s offer process is simple. “We don’t have bonuses, stock awards, or a vacation policy,” he said. “There’s not a lot of negotiation, so we try to get it right the first time.” Regardless of structure, transparency builds trust.

Make It Stick

Hiring doesn’t end when an offer is accepted; it begins again. “Onboarding must be a critical part of the recruitment life cycle,” I said during the session. Onboarding isn’t just technology setup or HR paperwork. It’s expectation alignment, early feedback, and cultural connection.

For smaller companies without HR teams, onboarding may be less formal, but it can still be deeply effective. A check-in call, a mentor, or clear 30-, 60-, and 90-day milestones go a long way toward building confidence.

One small business owner in the audience described a simple but powerful approach. They set expectations upfront, outline a 90-day plan, and hold check-ins every few weeks. That’s a wonderful model because it creates accountability and builds belonging.

The first 100 days are when promises turn into proof. Clear expectations, mentoring, and two-way feedback help new hires feel both seen and supported. This early structure becomes the glue that builds long-term loyalty—and turns hope into trust.

Change and Timing

Even with thoughtful hiring and onboarding, careers evolve. Sometimes change is the healthiest next step for both sides.

We asked Jay and Steve what prompted their own career changes. Steve said leadership transitions often drive reflection. “The tone is set by the leader of the organization,” he said. “When that shifts, I assess whether our paths still align.”

Jay’s story was more personal. After a near-shutdown at a previous department, he couldn’t shake the uncertainty. “I was never comfortable again,” he said. “I needed a change.” A new leadership opportunity appeared—the right fit at the right time.

Both stories reinforced the same lesson: timing and self-awareness guide every career move.

The Shared Goal

Jennifer summed up our message best. “Our hope is to create awareness and understanding for both parties so that each side understands the experiences and expectations of the other,” she said.

In the end, employers and candidates want the same thing—to work in a place where they can succeed and belong. When both bring honesty, structure, and empathy to the process, hiring becomes less about filling a seat and more about making the right match.

Hope may start the hiring journey, but intention, communication, and care are what make that match last. Because at its heart, every hiring decision in business aviation is a hopeful one. When we hire with purpose and lead with empathy, we not only retain talent—we strengthen our culture.

The opinions expressed in this column are those of the author and are not necessarily endorsed by AIN Media Group.