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An Unexpected Career Journey

February 23, 2022

A wise leader once told me that it’s nearly impossible to plan out a career path. There are simply too many possibilities, evolving interests, and unknown opportunities that might come along. This insight has proven true for me. I often notice this same thing when speaking with others about their own experiences as well. 

Something that I suppose is somewhat unique, has happened to me twice so far in my professional journey. In both instances I was happily working as a developer and some form of team lead, when over a short period of time my role in the organization changed significantly and I faced serious challenges in learning completely new ways of working. 

In both of these cases the changes were so drastic that it was impossible to continue working in a familiar fashion. I was no longer an expert. In one situation it was all about a brand new platform with new hardware and software in a stack not familiar to me and new teams that hadn’t worked together before. In the second experience the size change was even more significant and introduced a new complexity by having teams at different locations on three different continents. In either case I couldn’t direct people on what to do. I couldn’t review all the code or be in on every discussion and decision. Any effort to be that deep in the details would result in me being a huge bottleneck. 

These situations caused me to deeply explore and try out various approaches to leadership, organization design, and teamwork. What is a hands-on coder to do if that’s no longer an option? What models or philosophies would you embrace? Like all of us, mine is a journey of continued learning. Here are some key takeaways so far. 

Act like a gardner

Despite my last name and a grandfather who was great at gardening, I’m not very good at growing a garden myself. However I know for sure that walking out to the backyard and commanding the tomatoes to grow faster will yield no results, except maybe some serious concerns and funny looks from neighbors and family members. Instead of commanding and directing, look to nurture and enable. 

Nurturing like a gardener is the realm of environment and culture.  

It’s easy to create an environment that’s difficult for plants to grow in. Peopleware is a book full of insights about how companies hire smart people to do a job, and then proceed to get squarely in the way of those same employees completing the jobs they were hired for in the first place. We want to avoid this. We want an environment where people and teams can thrive. 

To that end please consider carefully:

Psychological safety - is it truly safe for people to speak up, openly question, disagree, and fail? 

Empower and co-create - instead of telling everyone what to do, help them to discover what to do. Encourage experiments, learning quickly, and freely sharing ideas. 

Shared understanding - Or as a good friend would say, is there clear and common understanding? If not, fix that first. Encourage more transparency, information sharing, clear communication, and focus on fewer things. 

Be invested in the success of others - The growth of others is the main success measure for leaders. Be sure to make this clear to those you work with. They need to know you’re committed to helping them succeed. Remember empathy and apply WISE compassion. 

Behavior matters greatly - Recognize that tolerating bad behavior is far, far worse for the environment than tolerating low performance. Nobody wants to work with brilliant jerks. Especially any that hold positions of power or authority. 

Teamwork is a huge competitive advantage - focus on creating strong teams. Strong teams are much more powerful than strong leaders. Unlock the collective intelligence of all involved. That’s what draws me to scrum. Product development teams aren’t about ultra-efficiency. They’re certainly not about keeping everyone busy either. Teams need to innovate and deliver value. That requires collaboration. It requires focus. It requires being more aware of the goals and the context.

Teamwork as scale is incredibly hard - It’s common to find orgs with strong individual teams, but silos between teams. It will take serious consideration of the whole environment and intentional effort to create a thriving organization. 

Be an enabler and a multiplier - Push decision making down and out to where the information is while also coaching and guiding those that need to make the decisions. In one of my experiences the leader I replaced moved on to an even more technical role. He had many more years experience with the organization and the technology than I had. He was also an amazing leader, someone I’d be happy to work for again. When I was serving in his place, I wasn’t able to lead the same way. It wasn’t possible. I didn’t have the same knowledge and skills. Instead the focus became about enabling all the people and teams to thrive. Thankfully we were able to elevate significantly as a group. Believe in people and give them room to learn and grow. 

Be very humble - Product development is very hard, there are unknown unknowns. Don’t believe that you have all the answers. Recognize that what did work well for you in the past might not apply to different situations. Understand it’s always a bumpy, messy endeavor and there's always more to discover and improve. 

Become a great listener - Listen to understand, not respond. Don’t make snap decisions based on a sliver of information.


Our modern world is very complex. Product development is inherently complex on its own. Wherever possible strive to simplify. This seems obvious, yet it feels like human nature to make things ever more complicated. It should not take superhuman effort to navigate your organization, know what to focus on, understand your code, backlog, deployment systems, or anything else. 

Regularly reflect on how you are operating. What can be simplified? 

In some of life’s endeavors it’s good to make things intentionally difficult. Military instructors and sports coaches do this all the time as part of training for combat or competition. In product development there’s no need for any of this. Are you trying to prove the people you’ve already hired are good enough? Or are you making things easier so you can all succeed together? 

Don’t underestimate the role of gardener

These things may sound simple, you might not think they will take a lot of time and energy. However don’t underestimate either the power nor the difficulty of creating and nurturing a great environment. To be a successful gardener you will need to leave behind other modes of working and incompatible mindsets. 

In the modern world we sometimes talk about hard skills and soft skills. I believe the soft skills, the human skills as I prefer to call them, are much more important and much more difficult to master. 

Waterfall Garden













"If there is no gardener, there is no garden." - Stephen R. Covey

In short, I’ve learned leadership is really hard. There are many examples and models all around us. Some useful and applicable today, many others that should be discarded. It takes serious effort to learn a better way. Continue to learn and experiment. It will be worth the effort. 

If you find yourself on an unexpected career path I hope it will be a journey of growth, exploration, and learning. 


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