He'd built the whole org. Then his own brain started running the room.
Addison — VP of Engineering
Addison had cried in front of his company's founders. Twice. On another occasion he'd yelled at his own manager—a founder, and the company's CTO. He was sure they wanted him out.
He wasn't struggling because he was behind. He'd grown from founding engineer to VP of Engineering, built the engineering organization from scratch, and carried a deep sense of ownership over everything he'd made. But as the company scaled, he felt stretched past his capacity—and when the founders suggested he delegate, he didn't hear relief. He heard: they've stopped trusting me.
The problem was never Addison's competence, and it wasn't his workload. It was the two-second window between what happened and what he did about it. Under enough stress, his reactions were arriving before his judgment could—and at his level, a reaction in the wrong room doesn't cost a task. It costs the trust of the people who decide your future.
Addison was already seeing a therapist; what he needed alongside it was leadership-specific. We worked on a handful of things:
- letting a feeling be information instead of a threat—so a hard moment didn't have to become a breakdown or a blowup;
- finding ways to discharge stress outside of work—he committed to a short daily hike—so it stopped compounding into the next meeting;
- naming his needs to the founders without making it about them, and setting boundaries that actually held.
Early on he told me, "I have to learn to suppress my feelings. Crying in front of my manager is bad for my career." We went the other way. Suppression was the thing compounding on him; the way out wasn't to feel less—it was to stop fighting the feeling and start choosing the response.
After two months of intensive work, Addison reconnected with the founders and they reached a real, mutual understanding about his role. He found a sustainable way to work, delegated what had been crushing him—and was eventually handed bigger responsibilities and grew into a stronger executive. He didn't cope his way out. He changed the situation.
This is the work. If it's yours too: