Building a People-Centric CTO Domain at a $1b Startup

August 9, 2022

Mathias Gran

One year ago, I accepted the role of “TBD” to help a rocketing startup outgrow itself. Under the leadership and partnership of CTO, JK Slyby, we realized the ideals of two core practices I developed for enterprises and adapted for this organization.

The first opportunity was delivery.

The very-recent startup intensity demanded a “build fast, build now, make it work” approach. It was wearing on the team, as they felt obligated to endlessly run on adrenaline. Nobody had ever structured work in a way that was measurable, nor had teams been given a chance to negotiate scope, sequence, or timeline.

The “Predictability First” approach I developed for Agile Data Science LLC was an essential first delivery. We don’t celebrate heroics. We celebrate balance. And we achieve balance by first identifying a reasonable capacity for each team and individual.

We started by visualizing team plans and driving conversations about setting realistic expectations. We repeatedly communicated that we should anticipate change and make room in our plan. We urged the teams to stop being victims of change. And we provided the data and narrative for each team to know where they stand each day and helped determine a reasonable amount of risk to assume.

In many organizations, I have seen that teams just need to be given a chance. The overconfidence that convinces teams to over-fill their buckets also makes them think they can catch up when they’re a day behind. With a little structure and a little permission to be great, I have seen deeply entrenched teams take off. When we empower teams with both advocacy and data, we create opportunity for teams to take ownership of their experience.

The teams thrived, almost immediately. Within six weeks, most teams were choosing an achievable amount of work. And for six consecutive months almost every team delivered at or above stated capacity sprint-over-sprint. It was the most substantial and rapid Agile Transformation I have ever led.

The second opportunity was leadership development under the CTO.

I often tell people I became an Agilist because I was convinced that great process makes great teams. However, process is firmly seated in the sidecar. PEOPLE who feel safe, supported, and engaged, make great teams. Hands down, the experience of each person is what drives the outcome. And, yet, we universally struggle to place experientially-minded people in supervisory roles.

I had been curating the foundations of Work With Feelings for some time. As an organizational change agent, I had been modeling some fairly progressive leadership behaviors at this startup. I trusted my skills and knowledge of leading high-performing teams, but I had never tried to package it for others. Then, JK gifted me a set of technology leads who were simultaneously smart, curious, and humble.

The leads wanted to be successful first-time managers and worried they would succumb to mimicking the defeating supervisory behaviors they tolerated throughout their careers. They knew something better was possible and they wanted to prove it. Just like their teams, they needed a little structure, a little permission to be great, and a skilled facilitator (if I can assign myself that label).

So, we launched a series of weekly leadership development sessions that is now the core offering of Work With Feelings. I invited them to follow me on a series of introspections to create conviction and clarity around what was deeply true and non-negotiable for each of them.

  • We discussed strengths-based leadership.
  • We overhauled the review process, capturing frequent and specific examples of greatness, making room for each person to shine in their own way.
  • We named our fears and apprehensions as emerging leaders.
  • We prepped for difficult conversations, insisting upon “more compassion, more compassion.”
  • We practiced celebrating individuals.
  • We collaborated to find powerful narratives to share with our teams.

We brought feelings to work and the leads immediately understood how psychological safety and supportive supervisors are leading indicators of success. I have never been offered such a warm room for this work. It was a magical experience for me to be with these leaders as a peer and guide.

We did this (and more) in just over six months.

If you can imagine how this might help you or your organization, please start a conversation.

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