Why the Messiest Career Transition Is the One Nobody Prepares You For

An Interview with Ashley Fina, Co-CEO of the Top-Rated Management Training Solution Oxygen

Career pivots, layoffs, industry changes: those are the transitions people talk about openly. But there is one career shift that quietly derails more professionals than almost any other, and it rarely gets the attention it deserves: becoming a manager for the first time.

To dig into this, we spoke with Ashley Fina, Co-CEO of Oxygen and a longtime executive coach and business leader (leadwithoxygen.com). Ashley co-leads Oxygen, the top-rated management training solution that equips high performers with the skills, tools, and structured support to become highly effective managers. Oxygen works with growing companies to help them build stronger teams through practical, cohort-based manager development programs.

In this interview, Ashley shares why the leap from individual contributor to manager is one of the most disorienting professional experiences people face, and what companies can do to stop leaving new managers to figure it out alone.

Interview

The Messy Parts: Most career transitions get a lot of airtime: changing industries, starting a business, getting laid off. Why does the move into management fly under the radar?

Ashley Fina: Because from the outside, it looks like a promotion. It looks like good news.

Nobody thinks of becoming a manager as a crisis moment. But for the person living it, the shift can be enormous. One day you are the top performer on your team. The next day your job is to make other people successful, and the skills that got you there do not transfer automatically.

The reason it does not get talked about is that it does not look messy. But it is one of the messiest transitions in a professional career.

The Messy Parts: What makes it so difficult?

Ashley: The identity shift is the hardest part.

As an individual contributor, your value is clear. You are the one producing results, solving problems, delivering work. When you become a manager, your success is no longer about your own output. It is about your team's output. That is a fundamentally different skill set.

Most new managers do not struggle because they lack talent. They struggle because nobody has taught them how to give constructive feedback, hold people accountable, or have difficult conversations. These are skills that need to be practiced, not just understood in theory.

That is exactly the gap that programs like Oxygen's Management Essentials training are designed to fill. Managers need structured practice with real-world tools, not just a one-day workshop and a handbook.

The Messy Parts: You mentioned accountability and difficult conversations. Why do those trip up new managers so consistently?

Ashley: Because they are uncomfortable, and most people have never been asked to do them before.

New managers often avoid giving direct feedback because they want to preserve relationships. They worry that holding someone accountable will damage the trust they built as a peer. So they stay quiet, and small issues become patterns.

The irony is that avoiding those conversations is what actually damages trust. Teams want clarity. They want to know where they stand. When managers learn to have those conversations with confidence and care, relationships get stronger, not weaker.

We see this shift happen consistently in our cohort-based programs. When managers practice feedback and accountability in a structured environment, they stop avoiding those moments and start leading through them.

The Messy Parts: How does stronger management change the trajectory of a company?

Ashley: When managers have the right tools and frameworks, the entire organization becomes more stable.

Fewer problems escalate to senior leadership. Decisions happen faster. Teams understand what success looks like and how their work contributes to the bigger picture.

The companies that invest in building management capability tend to scale more effectively than those that expect people to figure it out on their own. At Oxygen, we have seen this transformation repeatedly. Our programs help managers build the skills to lead high-performing teams, improve communication, and drive accountability across the organization.

You can see some of those outcomes in our client results.

The Takeaway

The career transitions that get the most attention are the dramatic ones: the pivots, the layoffs, the reinventions. But the transition from individual contributor to manager is one of the most common and most consequential shifts a professional can face.

Organizations that treat management as a skill that can be taught and practiced tend to build stronger, more resilient teams than those that leave new managers to learn on the job alone.

As Ashley explains, the transition into management does not have to be a quiet struggle. With the right training and support, it becomes the foundation for both personal growth and organizational performance.

Companies interested in building stronger managers can learn more about Oxygen's approach to cohort-based management training.

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 leaders scale their teams effectively.

Learn more at leadwithoxygen.com