In this series I’ll be writing about some of the challenges of transitioning to being a leader within the team you are in. In this article, I’ll discuss some of the difficulty in changing how you make decisions.

When you first transition to go from member of the team to leading that same team, usually it is because you demonstrated some sort of expertise. Some sort of “leadership quality“, maybe. Others see it. Whatever it is, people see that you have “it“. Now they want you to take this on.

Then your teammates start calling you “boss”.

In this article, the challenge I want to talk about is making decisions on things that are not always clear choices. I needed to accept that maybe I didn’t have all the answers. But as a member on the team, I was used to being the expert about something. And also I really enjoy being right! I have been in conversations where I have argued well past the point of being constructive just so I could be right.

When I was part of the team, my opinions on a subject were only a part of what leadership was taking into account. Usually, any decisions I made personally were only going to impact me, and then I’m on the hook to have to fix it if it goes wrong, so I’m the only one affected. When someone would ask “Is this hill the one you really want to die on?” my answer would usually be along the lines of “Yes I want to fight on every hill!”. I was completely willing to lean on my opinions, and what I believe in, every time.

I found it difficult to take that kind of very self-directed decision making model over to a leadership position. Now my decisions affected somebody else. Now I could affect company strategy. But I had a hard time accepting that maybe I was wrong about something. Looking back, there are probably a lot of times I tried to play all the odds to make sure I could always be right. But sometimes I was just being very rigid, sticking to what I knew.

On lacking flexibility

Being inflexible was definitely a problem early on (and some might mention that I sometimes still have this issue today as well!). Back in the day, I remember sitting in some boardroom talking about a product release with some other managers, as managers like to do, and somebody drew a cliff and they were implying we were going to be going over a cliff. I don’t know why the cliff was there… what I remember was that I didn’t care. I didn’t care about what the customers felt. I didn’t care about what other people’s opinions were about the situation.

What I cared about was the software release process. My team had flagged that the release candidate was not ready and that there were issues that needed to be resolved. I was going to fight that we had to make sure that this release was solid, that it did not matter what the customers needed or what deadlines they had. At the time, it never occurred to me to even consider that I might be wrong. I was thinking about software delivery as a software developer, a practitioner. I was looking at the situation as someone that wanted to fight for the right to do software delivery the way I believe it should be done.

But I wasn’t being flexible. I wasn’t willing to take input from other sides, from the business, and admit that I might be wrong or that there might be another way.

Making the right hiring decision is tough

Another side of trying to make decisions where you don’t have all the answers is in the hiring process. A long time ago, in another company far far away, I was involved in the hiring process for a new employee. They were not going to be reporting to me directly, but I was involved in the hiring decision, I was going to be mentoring them, so ultimately I was responsible for their success.  After reviewing several candidates in the process, I recommended we hire Chad.

(Their name was not actually Chad, but for the purpose of the article we will use the name Chad).

Chad was extremely good in the interview, great communication skills, good sense of humour, and generally really matched with the culture vibe of our team. I thought we could work together. They had a good set of matching skills to the job requirements, and we felt that we could train up a few of the more senior skills that would be needed for this role later on.

The first project we worked on together was a massive disaster. Even our most experienced people on the team were struggling. This was not the best intro! But Chad seemed to be struggling a little bit more. I chalked it up to maybe learning new skills, being new, and this not the best first project to take on. 

I ignored some red flags. I only saw them later. Things like:

  1. Chad wasn’t learning from mistakes, the same issues were popping up again and again.
  2. Chad didn’t seem to absorb information easily, you’d often have to explain the same concepts over again.
  3. Chad was ignoring the details, trying to get things done fast rather than focusing on doing it correctly.

I wanted to keep investing. It definitely couldn’t be that I was wrong about this person, right? There must be something that I’m doing, that I have not put this person into the right position yet, for them to succeed.

But the project failures continued, project after project. Eventually we had to admit this was not working out.

I was wrong. 

And I can say that, now, with conviction. But at the time? It was really hard to admit that I had made a mistake in how I chose someone to join our team.

What did I learn?

Well, I learned I needed adapt my thinking. I needed to accept that I’m not always right, I didn’t always have all of the information. I had to be flexible and, as the management buzzword handbooks always say, “Think of the bigger picture”. It wasn’t that I should ignore my instincts, or ignore the expertise I had built up, but I needed to bring all of the parts of the solution together and take everything into account. Everything that was available to me was part of the final solution that would work. It didn’t all just have to come for me.

When looking at decision making at a more strategic level, the answers are not going to be clear and easy. You will get things wrong, and the key is to assume that you are likely going to be wrong and find a way to adjust and adapt as needed to minimize the risk and fallout of the times you are wrong.

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