Transitioning from Developer to Manager

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Photo by Fabrizio Verrecchia on Unsplash

It’s not uncommon for successful software developers to find themselves in leadership positions. There are many possible leadership trajectories, one of which is management. Moving into management was scary for me, and over the years I’ve talked to a number of people at that point in their careers experiencing a similar dilemma. This is the story of my experience, why I made the decision I did, what I’ve learned along the way, and how it’s turned out.

The pre-management era

Let’s start with a little about my background, eh? I started my career as a junior developer and worked my way into a senior role, eventually becoming an architect. As an architect, I served as the technical lead for my team and worked closely with managers to make various leadership decisions. I wore many hats in order to best address whatever I felt my team needed most at the time.

After nearly 10 years with my first company, I left to join a former co-worker at a startup. At the time, this new company was small enough that we didn’t have much of an organizational hierarchy. We were a group of senior developers that all had decision-making authority with freedom to work on what we felt was most important. We still collaborated, of course, but we weren’t all chipping away at a common product backlog.

The loose structure worked great for us as a small team, but it doesn’t scale. As we added more people to the team and new products to our catalog, we needed more structure. We divided into product-specific teams with narrower focus and dedicated backlogs. That was our no/low-management tipping point, and that’s where my journey into management begins.

My boss was suffering the consequences of our very flat organization, and they needed people willing to take on some of these managerial responsibilities. I felt like I was being forced to commit: did I want to be a manager or not? I wasn’t given an ultimatum; in fact, my boss was very clear that there was no wrong choice, and my career would continue to grow regardless. That was comforting, but I still had the decision to make.

The management path was scary for a variety of reasons. I had a proven track record as a developer. I was good at coding and troubleshooting. I knew how to solve software problems. Managers take on an entirely different set of problems that require a different skills — skills I wasn’t sure I’d have. Managing a team when things are going well didn’t seem so bad, but it’s the whole “dealing with people” thing that had me worried. Did I really want to give up coding — the thing I enjoyed and had built a successful career doing — to be a manager and have to deal with people?

Making the decision

I ended up lingering at this juncture for a while. Depending on the day, I might’ve leaned one way or the other, but for the most part I remained undecided and non-committal. In my free moments, I’d research what made a good manager and read stories like this one to understand other people’s experiences. There were a few nuggets of wisdom that helped me make my choice.

Skills can be learned. It feels obvious to say, but hearing this was reassuring because I always considered “learning new skills” to be one of my strengths. It gave me confidence to know that I could supplement applicable existing skills with new, learned skills. For example, I know how to troubleshoot an application by stepping through code until I find a problem, then come up with a solution and implement it to fix the issue. The same critical thinking can be used to identify problems with a team, but I may need to do research on agile processes or collaboration techniques to come up with the solution.

You can nerd out on management. As a developer, there are always new things to learn and play with: languages and language features, tools, technologies, and techniques. I remember learning about something like Microsoft Azure for the first time and being so excited to have a reason to use it. The same kinds of continuous innovation exist for managers, too, but you need some awareness of manager & team problems in order for the solutions to make sense — just like you need context for those new things in software development. How can you automate team processes to reduce toil? What things cause the most friction or prevent work from getting done? How can you make 1:1s more effective? How can you maximize the team’s impact on company goals? How can you improve individual accountability? These are all super valuable areas to focus on, and they’re ripe for fresh ideas and innovation.

There is no “point of no return.” I was worried I’d go from awesome dev to mediocre manager, be unhappy, lose my edge, and feel trapped. It was reassuring to hear that I could go back and that my development skills wouldn’t disappear after being less active for a bit. I’m less involved in daily development tasks now and there are a lot of pull requests doing thing that I don’t understand, but when I do get back into the code, it all comes back.

As you may have guessed, I decided that moving into a manager role was the right move for me, and I’ve been at it for a few years now. It hasn’t always been fun or easy, but the more I do it, the more proficient I become. This has a cyclical effect, too, because increased proficiency leads to more engagement which brings more enjoyment and satisfaction.

Learning to manage

The most difficult thing about becoming a manager for me was the self doubt. (See imposter syndrome.) I felt like I was less valuable to the team “managing” than if I was a developer focused on getting things done. I wasn’t sure if I was spending my time on the right things, and the things I was spending my time on were different than that of my peers/other managers. I was failing to adequately help team members that weren’t meeting expectations. I was doing the best I could, and my boss was supporting and encouraging me — but I didn’t feel like I was doing a good job. It was tough.

Looking back, I think there were two key mistakes I made as a new manager. The first was not being direct with people. I was trying to focus on positive behaviors and encouragement and not being explicit about areas that needed improvement. The second mistake was that I didn’t think about the strengths and weaknesses of individuals on the team and strategize how to use them most effectively. (More on that, here!) You can imagine how these two mistakes can create problems: praise for strengths versus less feedback & higher expectations for weaknesses. It’s no surprise that situations didn’t improve!

The single most important advice I have for new managers is to lead with empathy. Get to know your team, and treat them like people. Give them positive and negative feedback. You’d want your boss to tell you if did something wrong, right? But, it would start to feel bad if they only talked to you about the things you did poorly, too. Learn details about their lives outside of work. It would get annoying if you had to re-explain every week why you had to be late to the same meeting for same reason. The better you can understand your team — professionally and personally — the more effectively you can manage.

The best way to get to know your team is through one-on-ones. One-on-ones are a pretty common “most important thing” for new managers, but the thing it took me a while to learn was how to prepare for one-on-ones. This is very hand-in-hand with leading with empathy. Being prepared for these intimate meetings is the best way to demonstrate that you care. Come up with questions and topics that are specific to the person you’re talking to. What do they like or not like about their job? What are their goals, and are there things you can do to help ensure they’re progressing toward them? What are things they did well or poorly? What do they think they did well or poorly? It’s also a chance to solicit feedback from them about you. Be sure to take notes! They’ll help ensure you don’t miss important follow-ups and make preparing for the next meeting easier.

The next steps

Managing with empathy and preparing for & conducting one-on-ones are things you can implement immediately regardless of experience. The next steps take some time and depend on your team. The most important things will be to establish behaviors that will maximize effectiveness and define a clear vision and purpose. These are no easy feats, though. They require thoughtfulness, focus, strategy, and persistence & dedication. You must monitor progress and be wary of regression, and advocate for the right amount of change to keep things trending positively. And, you need to do all this in addition to whatever your team needs to keep things going operationally!

This is a good summary of what my day-to-day looks like now. I’ve got meetings and operational concerns, and then extra time goes into reflection and solutioning for these bigger, longer-term items. There are still ups & downs; still days where I feel like I’m doing a bad job; and still days where I wish I could just write some code. It’s been a rewarding experience, though. It’s been amazing to watch the team adapt & succeed and to help people grow. I love when we can take on an ambitious goal and achieve it.

Making the transition to manager was a scary decision. I had to learn new skills to solve new types of problems, and I had to battle through some self-doubt. I don’t regret my choice, though. I’m not perfect, I make mistakes & bad decisions, and I’m still learning as I go. But, I love my teams, and I love the problem space that I get to live in.

Have you made this transition yourself? What things have helped you succeed? Are you faced with the decision now — what worries you? I’d love to hear from you!


Originally published at The Innovation on November 7, 2020.

Do One-on-Ones, Like a Boss

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Photo by Brooke Lark on Unsplash

There are millions of articles and books about the importance of one-on-ones for managers and leaders. When I was a new manager, it’s something I read about and put a lot of effort into. I didn’t feel like I was good at them, and I didn’t look forward to them.

But — like many things — the more you do them, the better you get. This is the story of things I’ve learned with time and experience.

Make Time to Prepare

This is the piece of the puzzle that I was missing for too long. The secret to good one-on-ones is preparation. Make it part of your morning routine to prepare for each one-on-on you have that day. Eliminate distractions and dedicate focus to each person you’re meeting with.

The secret to good one-on-ones is preparation.

How do you prepare for these meetings, though? It’s a combination of looking back and looking forward. Review notes from the previous meeting, reflect on interactions and contributions, and think about the person’s life outside of work.

First, you need to make sure you’ve dealt with anything you signed-up for last time to demonstrate accountability and build trust. If you missed something, that’s okay — there’s still value in bringing it up as something you couldn’t get to, provided that you don’t lose track of things and deliver more times than you don’t.

Next, think about the person and how they’ve been since you last met. Have they completed important work? Has there been conflict? Have they raised complaints? Have they been engaged? Have they been visible? As part of your preparation, identify positive and negative things to call out. These can be individual or team items, too.

Finally, look ahead to the future. What short and long-term goals does the person have, and are there things you can do to help them make progress? Some examples would be to follow-up on a commitment they made last time, give feedback on a instance where they exhibited a specific positive or negative behavior, or provide advice or reference materials that could help them.

The one-on-one is also your time to solicit feedback from them. How do they feel about recent changes the team has made? How is the current project going? What do they think about the direction of the team? You can — and should — also ask them about you. What could you do to help them or the team? What would make you more effective as a leader or manager?

Preparation checklist:

  • Did you take care of action items from last time?
  • Are there positive or negative things to call out?
  • How can you help with their goals?
  • What feedback do you want to solicit?

Be Persistent and Dedicated

Preparation is critical for effectiveness, but the most important thing is to actually have the meeting. Sometimes the biggest hurdle is just getting the meeting on your calendar. I’m an introvert, and one-on-ones are mentally and physically exhausting. The thought of another recurring meeting on my already-busy calendar was demoralizing. Don’t procrastinate. You know you need to do it, so just get it on there!

Making the appointment is nothing without keeping it. It’s important to put forth your best effort to make sure they happen. Don’t treat them as your lowest priority. Things will inevitably come up, and you’ll need to reschedule your one-on-ones sometimes. When that happens, favor rescheduling over canceling, and reschedule sooner than later; not showing or canceling at the last second sends the message that you don’t care.

It’s not always easy, but force yourself to have the one-on-ones. Arguably, the harder it is to have the meeting, the more important it is. Relationships that are most strained are ones that stand to benefit most.

Take Notes

If you’re anything like me, you’ve got a lot of meetings with a lot of people. It’s impossible to remember all the commitments and action items in my head. Take notes! Taking notes has multiple benefits beyond simply having something to refer back to, more so if you write by hand. It forces you to listen and be engaged which helps demonstrate to the other person that you care and makes distractions less… distracting. Research has shown that writing things down helps you remember, so you’ll naturally retain more of the conversation. And, lastly, taking notes gives you the obvious benefit of having something to refer back to. Taking notes is immensely valuable even if you never look back at your notes.

If you want to be a next-level note-taker, take handwritten notes during your meetings, then immediately re-organize them into a digital format that you can refer back to during future preparation and that can also represent a running history. Make sure to flag action items or mark things for follow-up, too. Depending on how you work and organize, you may want to add items to your calendar or task lists. The “secret sauce” here is that you’ve now written it twice — so you’re less likely to forget it, anyway — and you’ve got some fail-safes in place to make double-extra sure that nothing slips through the cracks.

Set the Agenda

I’ve covered preparation, scheduling & commitment, and note-taking during the meeting, but what about the conversation itself? Here are some things to keep in mind as you conduct your one-on-ones.

Let them go first. This is the standard one-on-one format: they get 15 minutes then you get 15 minutes. Their part is your chance to listen, take notes, and understand what’s happening with them as a person. If people aren’t opening up, try asking questions like, “How are things outside of work?” or give them a choice of where to focus like, “How’s life, at work or away from work?”

Prioritize topics. Treat them like people first. If last time you spoke to them, you learned they had sick family, don’t jump right into grilling them about the reports they’ve been working on.

Be direct. If somebody isn’t meeting your expectations, say, “You aren’t meeting expectations,” and explain your expectations and why they aren’t being met. If you don’t address problems, they won’t improve. If you only focus on positive things to encourage good behaviors, it’s going to be received as, “[you] didn’t have anything bad to say!”

Highlight positives and negatives. It’s easy to worry about negative feedback and improving performance so much that you forget to celebrate the good things. It can be a drag to only hear about what you do poorly, so be sure to shine a lot on positive behavior, personal growth, and team victories.

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Image by Free-Photos from Pixabay

Whether you’re a new leader or you’ve been at it for years, one-on-ones are an effective way to build trust, gain influence, and promote team & individual growth. It doesn’t come free, though. You need to do your part to ensure the effectiveness of these meetings, and that means more than just showing up.

Prepare. Commit. Take notes. Set the agenda with empathy. Do these things, and you’re sure to maximize the value of your one-on-ones!

I’d love to hear from you! What tips am I missing that make your one-on-ones most effective? What differentiates an okay one-on-one from a great one, or what things have you seen from the best leaders in your career?


Originally published at https://adamprescott.medium.com on November 13, 2020.