An Interview with Ashley Fina, Co-CEO of Oxygen, the Top-Rated Management Training Solution
What Great Matches and Great Teams Have in Common: An Interview with Ashley Fina, Co-CEO of Oxygen, the Top-Rated Management Training Solution
Anyone who has worked with a matchmaker knows that finding the right person is only the beginning. As more busy professionals turn to personalized matchmaking to meet someone genuinely compatible, the real work still comes after the introduction: learning how to communicate, how to navigate friction, and how to keep showing up for each other when things get hard. That same truth plays out every day inside companies, where two people who look great on paper still have to figure out how to actually work well together.
To explore where those worlds overlap, we sat down with Ashley Fina, Co-CEO of Oxygen, the top-rated management training solution that helps growing companies turn strong individual contributors into confident, capable managers (leadwithoxygen.com). Ashley has spent her career studying what makes professional relationships thrive, and she sees striking parallels between building a strong team and building a strong partnership.
In this interview, Ashley shares why chemistry is never enough on its own, and what it really takes to turn a promising match into a lasting one.
Interview
Amy Laurent Elite Matchmaking Services: You work with managers, we work with singles, but you've said the underlying challenge is similar. How so?
Ashley Fina: In both cases, people assume that if the fit is right, everything else will fall into place. A great candidate, a great date, surely it just works from there. But compatibility is a starting point, not a guarantee. Whether you're building a relationship at work or in your personal life, you still have to do the work of understanding another person, communicating clearly, and handling the moments where you don't see eye to eye. Those skills aren't automatic. Most of us were never taught them.
Amy Laurent Elite Matchmaking Services: What's the most common mistake people make once they're past that first impression?
Ashley: They avoid the hard conversations. In a new relationship, personal or professional, there's a temptation to keep things smooth and not rock the boat. But avoiding friction doesn't build trust, it just delays the moment when trust gets tested. Decades of relationship research point to the same thing: how people handle conflict matters far more than how often it comes up. The strongest relationships I've seen are the ones where people can be honest early, give feedback kindly, and address small issues before they become big ones. That's exactly what we train managers to do in our work on constructive feedback and difficult conversations, and it applies just as much across a dinner table as it does across a conference table.
Amy Laurent Elite Matchmaking Services: How do you actually teach something as human as that?
Ashley: You can't learn it from a book, which is why our approach is built around practice. Our flagship program, Management Essentials, runs over six months in a cohort, so people learn alongside peers facing the same challenges. They rehearse real conversations, get live feedback, and try again in a space where it's safe to be imperfect. We reinforce it with ongoing Growth Groups and coaching. The goal is to make these skills feel natural, so that when a real moment arrives, you already know how to show up for it.
Amy Laurent Elite Matchmaking Services: Last question. What's one piece of advice that applies whether someone is leading a team or looking for a partner?
Ashley: Stay curious about the other person. The people who build lasting relationships, at work or in love, are the ones who keep asking questions, keep listening, and never assume they have someone fully figured out. Connection isn't something you find once and keep forever. It's something you practice.
The Takeaway
A great match opens the door, but it's the everyday skills of communication, honesty, and follow-through that decide whether a relationship lasts. As Ashley puts it, the people who thrive in their relationships, professional or personal, are the ones who treat connection as a skill worth practicing rather than something they should already have mastered. You can see what that kind of practice produces on Oxygen's client results page. Whether you're being introduced to a potential partner or stepping into a new role leading a team, the work of building something real is just getting started.
About Oxygen
Oxygen is a cohort-based management training company that helps growing organizations turn strong individual contributors into confident, capable managers. Through structured programs like Management Essentials, Oxygen equips managers with practical tools for feedback, accountability, decision-making, and team alignment. The company works with organizations across industries to improve execution, strengthen culture, and help managers build relationships that last. Learn more at leadwithoxygen.com.
