An impossible choice—until it wasn't.
Blake — VP of Engineering
When Blake's startup was acquired, his job changed overnight. Instead of running his team's roadmap, he was stuck in meetings arguing with the new leadership about which database his team should use. The acquiring company ran on legacy practices and, as far as Blake could tell, a fundamentally different set of values. His role no longer fit—and he was frozen between two bad options: stay in a role he'd outgrown to protect his engineers, or leave for something aligned and abandon them.
He'd collapsed a complicated situation into a binary. Either/or thinking is what paralysis is made of—and it's especially common in sharp, analytical leaders who can model every downside in vivid detail. The work wasn't to help him pick a side. It was to test whether the two goals were actually in conflict at all.
So I asked him one question: "What if you could both help your team keep their modern practices and find a better-fitting role for yourself? What would that look like?" From there:
- We found Blake didn't have to be the one who paved the way. Someone on his team was genuinely energized by the acquisition and just needed the skills to lead the integration after he left.
- We worked on how Blake could understand what the new leadership actually wanted—and make them feel understood enough to open up to his team's more efficient practices. That turned out to be the hinge.
- Using a process I developed, we spent two weeks getting clear on Blake's core values, and whether they were genuinely misaligned with the new leadership's—or just different.
Blake worked out a plan with the new leadership to integrate his team in a way that served both sides. And with that resolved, he made his own decision cleanly: he chose to look for a better-fitting role, leaving behind a team he now knew was set up to succeed without him. Not a reaction to being stuck—a choice he could stand behind.
This is the work. If it's yours too: