Case studies

Emotional Rollercoaster to a Confident Executive

Addison, VP of Engineering

After Addison cried in front of his company’s founders for the second time, he knew something had to change.

He has been with the company for several years at that point, growing from a founding engineer to a VP of Engineering. He built the engineering organization from scratch, and made numerous contributions across many areas of the company. He had a strong sense of ownership, and he was proud of what he had accomplished.

But as the company kept growing, he felt increasingly stretched beyond his capacity. Yet when founders suggested delegating some of his responsibilities, he felt like they were losing trust in him and his ability to do his job.

When Addison approached me, he was unsure about his future at the company. He believed the founders wanted him out.

At the same time, he was stressed about the lack of clarity about his founders' expectations, and his ability to meet those expectations. He was also worried about his prospects to find a comparable role if he did indeed get fired.

The stress was getting to Addison. On one occasion, he ended up yelling at his manager-one of the founders, and the CTO of the company. On two other occasions, he broke down crying in front of the founders.

Addison was seeing a psychotherapist, but he felt like he needed additional help with:

  • regulating his emotions and dealing with stress at work,
  • communicating with his founders productively,
  • navigating conflicting situations calmly,
  • advocating for himself, and
  • setting healthy boundaries.

Using my training in ACT and MBCT, and my experience as a Mindfulness Coach, I focused on helping Addison to:

  • accept his feelings as appropriate responses to stressful situations and avoid taking things personally,
  • engage with conflicting situations with curiosity, listen mindfully, and prioritize understanding,
  • find activities outside of work to help complete the stress cycle in a healthy manner,
  • set healthy boundaries by focusing on his needs and communicating them non-confrontationally.

The first step was to help Addison stop avoiding and denying his feelings. “I have to learn to suppress my feelings. Crying in front of my manager is not good for my career”, said Addison. To which I responded, “Have you ever noticed how sometimes the harder you’re trying to ignore something, the stronger and more insistently it comes back?”

We also talked about emotional compression and how it almost always leads to depression, and that the way to unravel the emotional compression is to give yourself permission to feel all the feelings again-the happy and the sad ones, equally.

Next, we spent a session talking about completing the stress cycle. How our bodies evolved to deal with life threatening stress in a certain way, like running away from a predator, shivering, and so on. And how in the modern world, even though most of us no longer face life or death situations, our bodies still respond the same way to stress at work. But we no longer complete the stress cycle by running away, shivering, or playing dead. So the stress accumulates and eventually leads to more serious problems. During the same conversation we also brainstormed some ways Addison can cope with stress outside of work and Addison committed to going for a short hike every day.

Towards the end of our engagement, we spent some time discussing nonviolent communication. Both towards ourselves and with others. One of the key concerns for Addison was to learn to communicate with the founders in a more productive way and to set healthy boundaries with them. So we role-played a few scenarios using the principles of nonviolent communication as well as talked about how to communicate your needs to others without making it about them, without judgment, or shame.

After two months of intensive sessions, Addison re-connected with the founders, and they came to a mutual understanding about his role at the company. He found a more sustainable way to work, and delegated some of his old responsibilities to lighten his load. Eventually he was given new responsibilities that allowed him to grow and become an even more competent executive.

Startup Acquisition: From Conflict to Clarity

Blake, VP of Engineering

When Blake’s startup was acquired by a larger company, he found himself facing an impossible choice: stay in a role he no longer found satisfying and fight for his team or look for a better fit elsewhere and abandon his team.

There were significant differences between the modern engineering stack and practices of his team and the legacy practices of the acquiring company. The new leadership was seemingly uninterested in integrating the modern stack into their infrastructure. And instead of working on his team’s roadmap, Blake was stuck in meetings arguing with the new leadership about which database his team should be using.

Worse yet, according to Blake, the new leadership was seemingly operating under a drastically different set of values and he felt like his role was no longer a good fit for him.

Blake reached out to me to help him decide whether to:

  • stay and fight for his team and their more modern engineering practices, or
  • abandon his engineers and find another job that better aligned with his values.

Blake did not believe he could achieve both goals. He felt he had to choose between staying in a role that no longer suited him to support his engineers and abandoning his former employees. He was paralyzed by this difficult choice.

My strategy with Blake was to help him:

  • see whether it was truly an either-or situation,
  • connect with the new leadership and better understand their needs and goals for the acquisition,
  • together with the new leadership, develop a clear and mutually beneficial plan for integrating his team,
  • get more clarity on his values and, if they were truly misaligned, work out a plan for his graceful departure.

The first step was to help Blake explore his either-or thinking, so I said, “I just want to explore something, would you be open to that? What if it was possible to both help your team keep their modern tools and continue using their modern processes AND find a better fitting role for you elsewhere? What might that look like?” And we spent some time brainstorming ideas. In the course of brainstorming we discovered that Blake didn’t necessarily have to prepare the path for his team. There was somebody on his team who was excited about the opportunities the larger company was giving them and they just needed some help with skills that would enable them to support the team after Blake’s departure.

Next, we talked about Nonviolent Communication and how it might help Blake to connect with the new leadership and not only better understand their needs, but also make them feel heard and understood. Which in turn might create more openness on their part towards adopting the more efficient ways of building software that Blake’s team already had a lot of experience with.

This turned out to be the key element. Blake quickly internalized the ideas of nonviolent communication and was able to work out a plan with the new leadership for integrating his team into the large company in a way that was mutually beneficial.

Lastly, using a process I developed, we spent about two weeks exploring and understanding Blake’s core values and whether they are truly misaligned with the new leadership’s values.

In the end Blake decided that he wanted to look for another opportunity. And he felt like his team was well positioned to succeed without him.