000011 — Transition
Some form of “How are you doing?” “Are you okay?” “What’s next?” has been the most common question I’ve answered over the past twenty days since I announced my transition from CEO of Aspect Software back to a strategic board advisor. And when I answer with an honest and full-hearted, “better than I ever have been,” and then I tell the truth, that I’m excited for a season of rest, reset, rediscovery, reintegration, expansive thinking, dropping off and picking Noah and Olivia up from school more often, and sitting out back watching the clouds slowly move across the horizon, my response is met nine times out of ten with the most perplexed facial expressions I think I’ve ever seen in my life.
So I add the second sentence.
No really, I am good. This was intentional. This was part of the process. Part of an assignment scoped years ago.
And it still came with emotion. Relief. Tenderness. A strange kind of quiet grief. Not because something went wrong, but because something mattered.
That’s when I realize I’m not only answering a question about me. I’m confronting an assumption a lot of us carry, and rarely challenge, that transition means something went wrong. That release means loss. That stepping out means stepping down.
And the longer I sit with it, the more I think the opposite is often true.
Healthy systems transition. Families transition. Organizations transition. Nations transition. The only thing consistent is change, and the skill is not avoiding it, the skill is learning to participate in it with clarity, humility, and care. The difference between chaos and growth is rarely whether change happens. The difference is whether we prepared for it, and whether we know how to hand off well.
Side note. I’ve had Yacht Rock on for the last few hours to mentally escape the winter cold and snowy landscape outside my windows. There’s something about that music, lightness without denial, joy without pretending. If you need a quick reading break and want to turn on some Player really loud, I support it.
When I was invited in 2021 by the newly formed board to participate in leading a growth turnaround strategy for Alvaria, Inc., an organization in decline and crisis formed by way of a merger of two pioneering technology brands in the call and contact center space, the seasonal imperative was to stabilize by restoring coherence.
In the subsequent months, after spending time with customers, employees, analysts, and observing macro and local forces, my initial assessment and strategy thesis was anchored in three objectives: return to core product and category competencies and organizational structures, invest heavily in product innovation and culture, and restructure the balance sheet.
The last four years, we worked tirelessly to execute that thesis. It served as a gravitational anchor when there was turbulence. We charted a direction, agreed on that direction, and relentlessly adapted until the thesis was satisfied.
In September 2025, the last objective in the initial thesis was satisfied publicly. We reached an agreement to reduce the company’s debt by more than 75 percent and receive approximately $50 million in new investment. By October 2025, the transaction closed, the roughly $1 billion debt load was reduced to approximately $200 million, and $50 million of new capital was invested in the business.
During this season, I had the privilege of standing in many roles, from board-appointed Strategic Advisor to Chief Strategy Officer, Business Unit GM, and CEO of the restored and reinvigorated Aspect brand, and now back in my role as Strategic Advisor. Some version of this pattern has been true throughout my career: step in with a thesis, act as a change catalyst, ensure stabilization and durability, and then make room for what’s next.
It’s why, in the later innings, (see Michelle, I really am a sports person now haha) I began preparing the organization and the market for the signals of health. It’s why I wrote notes to the folks at Aspect in public posts, holding up a mirror to what they accomplished and where they were headed. It’s why I attended fewer internal and external events, so the next layers of strong leaders, from my directs to L2s, had more presence, more voice, and more authority as we prepared for the next season of growth and leadership.
In time, the reality became plain. The utility of my competency and skill set as a strategist, a turnaround catalyst, and a change agent had been maximized in this chapter. The mission inside the mission was accomplished. And the handoff mattered more than my continued presence.
The transition to the new interim CEO was clean, and I adore and respect Jeff Kupietzky. He is the kind of leader who will continue to pour into culture, product, and process so Aspect can keep becoming more innovative, more effective, and continue delivering unreasonable value for the brands that place their trust in the organization.
I’m also profoundly grateful to the people who carried this with me, especially the team inside Aspect who kept showing up when it would have been easier to check out.
Now for the hinge.
I’m not leaving leadership. I’m changing the form.
This next season is about width and depth. It’s about investing, advising, building, studying, and creating, and doing it with more spacious attention than I could access while carrying the operator seat. Writing is going to be a bigger part of that, not as a performance, but as a practice. Some of that practice will live here when it has become useful enough to share. This site is where I’m going to continue, and more consistently process what I’m seeing and learning in public, through field notes and essays, and through the honest work of making sense of the complexities and nuances around us, around me, without oversimplifying or avoiding.
If you’re wondering what I’m up to, it’s this. I’m investing, advising, studying, and writing. I’m building a body of work that makes complexity clearer, and makes leadership more human.
We’re also stepping into a broader transition as a society. An intelligence economy. Tools that once belonged to specialists are becoming widely available, and capability is going to scale fast. That can be a gift, and it can be a trap. I don’t think the advantage goes to the people with the most tools. I think it goes to the people who can pay attention long enough to use them with discernment, and stay accountable for judgment, meaning, and the human consequences of what we build.
Healthy transitions are not proof that something failed. Sometimes they are proof that something worked long enough to be handed to the next faithful steward.
So I’m good. Really good.
Because this is what health looks like. A clean handoff, a stronger foundation, and the team ready for the next season.
