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How Clarity Can Help Retention

Career Path
Company Culture
Managing Expectations

30 August, 2020

Brad Henrickson, CTO at Scoop, explains how an added level of clarity on processes and roles helped him retain one of his highest performing engineers.


In a previous company I joined, we hired a person with a very strong track record on the technical contribution side; a smart and successful individual passionate about infrastructure and scalability. He was very excited about what we were doing and was eager to deal with some concrete problems and strategic matters that had to be addressed. Two months into his role, he pulled me aside and told me that this was not working for him. He laid down his reasons and confessed he felt like not being the right fit.

Due to his exceptional competencies, I wanted to retain him; but, I was also open to the idea that he was not the right fit.

Actions taken

We had a very open conversation about what he identified as key challenges within the organization and I too shared my vision where we wanted to go and where I see him in that constellation of developments. It was a very transparent discussion about his career aspirations and how he could contribute to where we were heading towards. What I’ve learned through that conversation was that he liked what we were doing and the overall culture but that he felt there was too much ambiguity and he was not able to get much of a traction. He was particularly concerned about how we made technical decisions, what was the role of product, how we measured success of the business, etc. and felt there were too many unknowns that were hindering his performance.

This initiated a series of conversations over the course of several months during which we were engaged in a candid exchange of views and opinions about what were the main challenges, how we should approach them, how he could contribute to that, etc. We both were transparent and showed vulnerability that allowed our conversations to be frank and inspiring.

He soon was able to make a decisive contribution and became one of the highest performers on the team. He made a significant impact with his distinct approach to architecture and moved from being consumed by the technical problems to being able to drive, influence, and take ownership of the key problems and challenges.

During all of our conversations, I was trying to carefully listen to him, empathize with his perspective, appreciate him having divergent opinions from mine, and encourage him to express his views. We created a loop of interactive exchange and charted together the path forward that resulted in co-authoring a number of important documents that altered the way we did things and the environment we operated in. Shifting from the reactive to the proactive role was an intrinsically rewarding experience for him.

Lessons learned

  • Don’t write people off who don’t feel like being the right fit. Instead of taking for granted their assumption, you should try to dig deep and understand where a person is coming from and what their values and aspirations are.
  • Don’t underestimate the power of vulnerability and transparency. When it comes to building relationships and forging a path forward, collaboration and co-authoring should make those relationships stronger. If you are on a receiving end of a decision you often can feel disempowered and collaborative activities and shared ownership can be incredibly empowering.
  • One of the challenges this person identified resonated with other people in the organization, but he was the first to bring it under my attention. If someone is troubled by a particular challenge it might be that it is something troubling other people as well.

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