Notes on Technology Leadership Lessons Learned

On one hand I have had the good fortune of growing small technology teams but at the same time – on my other hand – I’ve had the bad fortune of making some critical mistakes (or take risks) that have made the whole process of growing and maintaining a high performing team extremely difficult.

Therefore, I was keenly listening when Bohdan – a Serial CTO, Advisor, and Entrepreneur – was giving a talk on lessons he learned as a technology leader. His reflections came from his decade long experience as a technology leader helping build some of the most successful Canadian startup companies – Kik,, Fixmo (acquired by google).

Thanks to him, I was able to validate an update some of my learnings about building technology teams which I will share below under the categories of Hiring & Culture, Establishing & Evolving Processes, and Tools to Use.

His notes are simple and are relevant for any leader responsible for growing and managing a team.

Notes on Hiring & Culture

  • Know Who NOT to Hire – Many people know the ideal profile of the candidate they want to hire but rarely are alert on the kind of person they don’t want on the team. “Never, never hire the brilliant @$$hole”, is something he kept emphasizing.
    • Example: Donald Trump – We all knew what kind of presidential candidate we DO want but rarely realized who we DON’T want. Hence, we somehow let him be “hired” into the public limelight.
    • Why Not hire brilliant “@$$hole”? They do more harm than damage. They are not team players, ignore processes, work on their own and eventually start working on side projects of their own.

  • Skills and Personality are virtually irrelevant. Focus on culture aptitude and cognitive ability.
  • Look for people who ask questions, listen and act.

Notes on Establishing & Evolving Processes

  • Be very careful with this double edged sword
  • Use them but always question them. They tend to become rituals with absence of thought and rationale behind doing them.
  • Example: A company had the culture of laying out requirements on paper on the wall as well as on JIRA. As time went on, the company continued to maintain both the copies – electronic and digital which caused a lot of pain. Surely, the team members did not intend to do this but it just happened as a byproduct of their established processes.

Notes on Tools and Technologies for Teams

  • Provide all the tools that the teams need to perform (within rational reason)
  • Avoid Shiny Objects or Unproven Tools

If you would like to dig deeper in each of the points above, you can watch his talk for TechTo and slidedeck of CTO Leadership Lessons Learned. Also do checkout his company, Fortay, which focuses on solving these critical problems of Talent, Culture, and Team building for companies. Lastly, if you are live in Toronto and a technology executive of a specific sized company, I encourage you to checkout his Toronto CTO Meetup Group.

Steps Going Forward

With time and experience, I hope to build on top of the notes and reflections above. However, as Bohdan would emphasize;

“Leadership usually comes down to a few fundamentals and practicing them well.” – Bohdan Zabawskyj


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