Human Skills 022: Vulnerability and Leadership
with Jamie Strachan
Jamie Strachan worked his way up through various software roles until he reached Architect, at which point he realized that increasingly his work was made up of people problems instead of software ones, and decided to try management.
In our conversation we talked about that transition, how he had to come up with new ways of thinking about what it means to do a good job, and how to determine what work matters. From there we went deeper into the human aspects of leadership, talking about vulnerability and mental health. Jamie has been open about his struggles with depression, speaking about them both publicly and in more private settings, and we talked about how doing that as a leader can open the door for people that are not in positions of power to talk about and seek care for their own mental health challenges.
Do you have a framework for assessing if you're doing a good job as a manager?
I think the first step of it was to, even for myself, just come to terms with the fact that my contributions were not going to be based in the code that I wrote.
That's what I was used to. And so when I started as a manager, if a problem would come up, I'd sort of be like, "oh, I can fix this". And it was sort of like a learning process to be like... sure, maybe I can fix this, but there are other ways that these can be fixed. It makes opportunities for other developers, giving people a chance to do this.
And Instead of that feeling of" I'm failing because there's a thing that I could do that I'm not doing", feeling like, "oh, this is actually a win in the sense that it's a learning opportunity for somebody else." It's a chance for me to spend time working on something that's higher leverage like communication alignment than fiddling with a PR that a senior dev can do way faster than me.
So part of it was just that mindset shift. I think the other part of it is understanding the time scale of what success looks like. I got into web development mainly because the feedback loop is so fast. I loved being able to write JavaScript or change CSS and immediately see what the impact was on the screen. I'd done back-end before that, and it was less rewarding to work for hours, days, months, and then hopefully data got transferred to the right place or whatever. It was just far less tangible and visible.
So front-end web development, feedback loop is very quick... management less so. So you're thinking in terms of years when it comes to people's growth, learning skills, getting promoted, all those kinds of things. So you also just have to like realize that your day to day activities are really going to be cumulative in terms of like major outcomes as opposed to you finish an eight hour day and you're like, "here are the 10 things that I like took from start to finish" because that just doesn't really happen anymore.
How do you help people know their work matters?
I think there's the easy answer to this, which I don't know if it's the most effective answer. I've worked in companies that are, say B2C for example, where you can point to, here's the feature that you're working on and like, here's a customer that's gonna use it.
And sure, therefore you know this work you're doing is improving their life in some way, which is like not wrong or anything, but. But again, I found that even that feedback loop is longer than you want it to be.
Like by the time a feature gets developed and tested and rolled out and through feature flags and A-B testing or whatever else it takes for it to finally get used. And then hopefully you get actual feedback from a customer saying, "this is a great thing." There's a long time between starting that process and ending that process.
So that may be the most direct line to draw, but it's not as tangible, or as rewarding maybe as developers want. So I think one of the things you can do is look at the people who are much closer to you and how your work impacts them.
Especially working with say, senior developers, mentoring for example or pairing are really nice, quick, tangible ways for you to realize that "okay, yes, sure. I'm helping a customer with this thing they need to do, but also , I'm helping this developer that I sit next to learn this skill or get this PR done or figure out what's wrong with this test, why it's failing."
And so that measurement of value and reward doesn't have to always be drawn all the way to like, the bottom line and ARR and customer satisfaction. There's lots of internal metrics for who it is that you're helping. and what your work is doing to benefit your peers.
How do you think about vulnerability as a leader?
I learned years ago that the more that I'm able to be vulnerable and share things with people, the more it gives them an opportunity to.
And this to me ties in with leadership and management because it almost becomes an obligation to some degree. The power dynamic is such that if I'm a manager and I'm speaking to a direct report, it is riskier for them to tell me certain things, right? They might be concerned about the precariousness of their position or even just basic stuff.
If they're worried that if they talk about struggles they're having they're going to get fired as opposed to supported, that's a very difficult place to have a relationship that is candid and is useful and valuable.
So for me, I look at it as, for me to be vulnerable, for me to talk about challenges I'm having and things like that, it just helps sort of open the door and like helps lead. And basically use the fact that I'm in this power position to be the one to approach it. To make a demonstration that like, "Yes, we can talk about this stuff and I'm willing to go first because, I have theoretically less to lose."
On how public speaking is different than you might think it is
I remember going to conferences and seeing the people presenting up on stage and being just in awe of these like these incredible, brilliant, wonderful people, like these celebrities or whatever it was.
And I remember a number of years ago, I sort of decided that getting into public speaking, presenting at conference was something I wanted to do.
When I got into it, I was like, "oh, I'm just a guy." There's nothing that magical about me getting up on stage and doing this. It's a skill, sure, and it's something you can practice, but it is not the sort of rarefied air that I thought it was, of only the most elite could possibly do this thing.
It's also nice to be able to relate to people on that kind of level, to reduce that gap. I've done speaking before, I coach people on public speaking and have done before because it's a skill you can learn, but also, it's neat.
I like going to conferences and having people come up to me and talk to me about stuff that I'm interested in because I gave a talk about it as opposed to me walking into a room full of strangers and being like, ugh, I have to make small talk.
On mental health and being a leader
I can sort of bring this back to, we were talking before about vulnerability. I have been pretty open with mental health challenges that I've had in the past. I have talked with public speaking, I have gotten up on stage multiple times and talked to people about my depression.
And again, that is something I feel like I can do. But I also feel like doing that, hopefully either opens the door or at least gives other people an opportunity to see someone in my position, being open and vulnerable about that.
It's not like... I don't go around waving a big flag about or carrying a big sign that says how depressed I am, but I mean, it's a humanizing thing.
And so it's both useful in... presenting and in public speaking... but we talked about building relationships in one-on-ones and because it's something that I've been open about and will be open about...
So at work, for example, like there are days where I just need to not be at work. I just can't, and need a day off. And historically that was sort of stigmatized. Like... you take a day off, you sort of have to explain it or whatever it is. And I think it's really valuable to give people an opportunity to take time off and give them the trust that if they need the time off, they should be able to take it without a detailed explanation of what's going on with them.
That being said, I am generally pretty open about the fact that like, if I'm taking a sort of mental health day or whatever, that this is why I'm doing it. And what that means is sometimes in, in one-on-ones and with relationships that I have with reports, they are more willing to talk about their challenges.
And I'm not a therapist, I'm not a doctor, and the point of that is not sort of like, so I can help them with it, but at least I can accommodate more effectively, I think. If they're able to tell me what's going on, again, I have no interest in being sort of intrusive and knowing more than I need to know about people's lives, but it's sometimes useful context to know that this person is dealing with a long-term health condition and they're having a difficult time with it right now, or they're dealing with something at home that is very stressful and it's been affecting their performance at work.
If people aren't willing to talk about that, then I think you can get into situations where, if performance gets impacted, you don't want to make assumptions about, "oh, you know what, this person's just sort of not working out," when in fact they have a real situation at home, it's making it very hard for them to concentrate at work.
So the vulnerability piece for me, is leading or being the one to open that door by talking about some of my own challenges. And... often that leads to people being more open with theirs, which in turn means I can support them better, which is great.