Tamara – The CTO Buried in Busywork

From bottleneck to strategic leader

The Pain

Tamara was the chief technology officer of her third startup. She was sharp, driven, and deeply committed to her team. But her days were swallowed by urgent, unimportant tasks. Administrative work and constant interruptions left her drained. She couldn’t focus on strategy. She couldn’t breathe. Her team depended on her for everything, and she had no time left for herself—or them.

She felt like a bottleneck. Every decision waited on her. Every meeting pulled her in. Her calendar was a battlefield, and she was losing. She missed dinners. She missed sleep. She missed the joy of building something great.

The Approach

Tamara’s initial Deep Dive Diagnostic indicated two hotspots, which we tackled in parallel:

Sustaining her movement. We used tools like Scatterplots of Now and Fantastic Facets to define her preferences: what energized her, what drained her, and what she needed to thrive, and then to custom-build rituals to nurture her well-being and protect her time.
Managing her impact. We built a Change Map depicting every blocker to her strategic focus. Then, we used tools like Tiny Experiments and The One Thing to tackle each one, from delegation gaps to unclear priorities. We custom-built systems that helped her step back and delegate with confidence that things wouldn’t fall apart. And guardrails to protect her and her team, just in case they did.

As we progressed through these, the performance hotspot started moving from Tamara to her team. We created a Change Map to explore what might best resolve the issue. That led to a series of “town hall” meetings wherein Tamara explained the issues she had been experiencing and the steps she was taking to resolve them. She also acknowledged the impact this was having on them and asked how they would like her to help them through this change. The near-universal answer was that her people wanted the same resiliency and adaptability Tamara was finding. This led to:

Coaching the coaches. Alongside my weekly sessions with Tamara, I added sessions with her key staff. As I guided them through the Uncommon Teams System, I also coached them on how to do this for their teams.
Open “office hours”. Tamara and I scheduled regular blocks of time where anyone could come and ask questions. While these were originally meant to answer questions that cropped up as people worked through the Uncommon Teams System, they quickly turned into Ask Me Anything sessions about all aspects of the business.

The Transformation

Tamara reclaimed her time. She started her days with clarity. Her team made decisions without her. Strategy moved forward. She felt present, powerful, and proud. Her company didn’t just grow—it matured.

Burnout Leadership Capacity

Burnout risk fell from 83% to 12%
Uncommon Index self-assessment rose from 63 to 116 (out of 124)
Administrative work was reduced from three hours a day to three hours a week
98% of interruptions corralled into daily “office hours”

Team Performance

3 projects halted, saving 15 engineering months of work
Escaped customer defects reduced by 35%

The Time Frame

Six months of mostly weekly one-on-ones with Tamara, followed by another six months working with Tamara and her key staff.

The Sustainability

Eighteen months later, I checked back in with Tamara and her team. She had continued to reassess her Uncommon Index every month, and, as is normal, it had some downs as well as many ups. Nevertheless, she was sustaining her change. “You gave me back my life—and my team,” Tamara told me.

The team was sustaining their changes, too. Tamara’s principal architect summed it up like this: “Tamara empowered us to make even the biggest decisions and stood behind us whatever the outcome. Everyone felt more engaged, excited, and invested.”