Many of my blog posts start as a response to something I see online. I start typing away in a comment box, and I soon realize either:
I’m going to go way over the character limit
I’m going to want to reuse this
Or both. Today, definitely both.
Someone in the LeadDev community recently posted this:
I’m a tech lead / staff engineer (20+ years in the industry). I’m quite technical, I was an engineer… I’m kind of hitting a ceiling and I’m looking at what I could learn next.
This person considered a number of different educational or certificate programs including some technical ones, but added:
but I feel I need to learn leadership skills, or find a blend between technical and leadership. Any idea or inputs for me?
Well. Good to know that there’s demand for the book that I’m just starting to write! But I also can’t write an entire book in response to a question on Slack. “Hang on about a year and a half and I’ll have something for you…”
So let’s boil this down to some concrete steps that worked for me.
Talk to your boss
If you have a supportive manager, that might be a good place to start. Your manager may be able to give you some feedback (knowing your existing skills and strengths) and advice (knowing what opportunities there might be at the company).
Take on a challenge
You might look for a new assignment within your role, or even a new role entirely, that challenges you in new ways. Leverage your existing skills to show why you are ready to take on something that might at first seem to others (or to you!) like something above your level. “My experience creating mid-level strategies will be useful on this project where I would gain additional experience [doing xyz]…”
And don’t sell your current skills short! You don’t need a people-manager title to be a leader.
Look for a mentor
Would it help to have a mentor – someone (who isn’t in your reporting chain) to turn to for advice on leadership challenges, who might help you get more visibility into how leadership works at your organization, who may be able to nudge you in the right direction?
I wrote about some of my experiences finding and working with my mentors here: Choosing a mentor. Note the distinction between “mentor” and “sponsor.”
Provide guidance to others
You could also be a mentor, but there are other ways you can offer guidance to others beyond a formal mentoring relationship:
Responding to requests for help from developers who are stuck
Presenting or doing a Q&A session on a topic you know that others may not (e.g., the architecture of a solution you worked on, or a new technology you’ve tried)
Documenting a tricky process to make it easier for the next person to go through it, or breaking a confusing topic down to make it easier to understand
Study the leaders around you
Whose leadership style do you admire? Why?
Who seems successful as a leader in your organization? Who has the respect of your peers, of their peers?
Who is “leading without authority”? They are clearly a leader, but they don’t have the title or rank perhaps you might expect.
Are any of these people approachable?
Books I recommend
I’ve read a lot of enjoyable books, but here are a few that were not just good reading but which actually changed how I think.
I’m in the process of reading The Staff Engineer’s Path, by Tanya Reilly – but recommending that in LeadDev might be like recommending The Phoenix Project in the DevOps community – something that people have read already!
Formal training?
I’ve looked at a number of academic-type programs in leadership, like certificates from various universities, but I’ve never been able to bring myself to spend the money on them (some are five figures, ouch). I’m more of a fan of getting my training in the work setting, where I can get paid to learn as I go.
One certification I’ve considered is Gary Gruver’s Engineering the Digital Transformation, and I did at one point buy the course material for it… I just haven’t had the chance yet to go through it. I would read Gruver’s book by the same name first, though, which will give you a good idea of what ground the training would cover. (It’s also a great book.)
That’s a start. I can never tell how obvious (or not) some of these things are to others who have been in the field a long time, so I’d love to know if things on this list are helpful to you. I’ll also keep updating this as I think of new items that belong on the list.
Good luck on your career journey! (And do sign up for my mailing list if you’d like updates on the book.)
I’m happiest in a job when I’m learning from someone who knows more than I do.
Last year [this post is originally from August, 2023], I started a new role on a team of engineers who all know boatloads about stuff I don’t. That by itself was a dream come true. Just after I started, we learned that one of my teammates would be going on parental leave in a few months, and it was decided that I would pick up his responsibilities while he was out. So, lots of knowledge transfer was about to happen. Better yet, he’s a great teacher, great to work with, and he works on things I’m interested in.
Luck is not a strategy
Let me clarify before we continue: I’m not telling you to get a mentor by changing jobs to one where everyone could be your mentor and the person who would be the best match from among them just happens to be going on leave half a year later. Nice work if you can get it, but that’s not a strategy, that’s mad luck. And it’s just the preamble to the story I want to tell you.
The downside to this magical plan of knowledge transfer galore became painfully obvious about 5 months later when joyful news of the baby’s arrival meant my new work BFF was suddenly not available.
Side note: it was less than 24 hours before we had a question that only he could answer. 😂😭
I was too busy adjusting at first to notice, but it wasn’t long before I could see I was adrift. I needed a new mentor. But who?
Start with the obvious
First question I asked myself was an obvious one: “who do you know who might be a good mentor?” A worthwhile question, but for me it only generated some names who didn’t seem like good matches. People whose focus was different from mine (including most of my team). People who were probably too busy. People whose skills were too much like mine.
Photo by Desola Lanre-Ologun on Unsplash
I suspect this is where some people get derailed. I can’t think of anyone, or I don’t dare ask because I doubt anyone has time for, or interest in, working with me. And what would I ask them about anyway if we did work together?? The “who do I know” question was getting me nowhere, but it’s worth a shot, maybe someone leaps to mind for you.
Decide what you want
I thought about asking my manager, but then I realized he would probably ask: “what do you hope to get out of mentoring?” Huh, I hadn’t thought of that, beyond “someone to learn from.”
There’s an important distinction here between “mentor” and “sponsor.” A mentor is a guide who can teach you, advise you, help you get unstuck. A sponsor is someone who can advocate for you in rooms you aren’t in, look out for opportunities for you, help you make connections. Identifying a potential sponsor is a whole other post. In this case, I wanted a mentor.
I was looking for someone knowledgeable in topics I was interested in, someone who could answer questions or offer advice I had when I got stuck on those subjects. Someone who could give me a perspective from a vantage point different from my own.
The next question that arose from this was: “what are you interested in?” Again, I hadn’t really given that much thought. I was immersed in this world of NodeJS and Kubernetes and cloud migration, but was that something I wanted to keep focusing on?
I thought about the things I had been learning about recently, and DevOps came to mind. I know that term means different things to different people, so a few examples would be useful here. I had recently read The Phoenix Project by Gene Kim, Kevin Behr, and George Spafford (great book!). I had read some writing my new-dad colleague did on the mindset shifts needed for a devops transformation. I’d read a few items from our Enterprise Architecture (EA) team about it, and I’d been to a few architecture “community of practice” meetings where one of my EA colleagues had presented about that. That same person had written the “getting started with DevOps” article that recommended The Phoenix Project.
As you might be guessing, this gave me an idea for who I might ask.
You might also be thinking: great, Leaf, that you thought of someone. What if nobody had come to mind? That’s where I would have reached out to my manager. Having decided what I was looking for, I could start to tap my manager, or other people who have been at the company a while, to see who they knew who might be a good match.
Deal with the doubts
I had a name that seemed like a potential good match to me, but I still had doubts. Would he have time? Interest? Could I even set this up? He was in a completely different part of our tech org. And what would I say?
I decided to deal with most of those doubts by ignoring them. Why cancel an opportunity before you even try for it? There was no way to know what would work unless I asked. I happened to have a 1:1 meeting with my boss’s boss around the time I was thinking about all of this, and I realized he might have the insight into whether this cross-org match would work. I brought it up.
Sure enough, his first question was about what I was looking for from mentoring, so I was glad I had an answer ready. He offered to talk with my potential-mentor’s manager about it, and a few days later, I got the go-ahead.
We scheduled our first chat. That left me faced with the question of what to actually say.
Arrive prepared…ish
I already have a rough framework for how I introduce myself to someone. It’s kind of a mix-and-match set of phrases about me that I tailor for my audience, omitting things they already know and focusing in on what’s relevant. I’ve been a developer for 20 years, I became a tech lead in 2020, I got to help an application grow from empty repository to serving users in production… that sort of thing. It situates me in time (how long I’ve been doing what), space (in the org chart sense), and experience (dev-turned-architect, learning devops). Pausing to invite the other person to share anything from their background or current interests is probably a good idea here, although I don’t think I actually did that, oops.
I also had some ideas of how I was hoping this mentoring thing would go. Maybe meet once a month for half an hour, I’d batch up any questions I had about things I was learning. It was almost a “hey, let’s try this and see if it’s useful.”
Other than that, though, I didn’t arrive to our first meeting with an agenda other than introducing ourselves and setting a cadence. I think that’s fine. I mean, if you have questions to bring already, bring them, you never know… but the first meeting doesn’t have to be a teaching session. It can just be an introduction, especially if you have not actually talked with this person before (I hadn’t).
Bonus points (“wow, I wasn’t expecting that”)
Let me just say that I had no idea what I was getting into with my new mentor. In a good way.
Photo by Marcel Smits on Unsplash. That’s not me, but I did have curly hair like that as a kid.
First? He was actively listening, even taking a few notes as I talked. It was clear that he didn’t want to interrupt me, but he was noting items he wanted to circle back to when I was done. Okay, I haven’t even finished introducing myself yet, and I’m already learning. Win.
Second, I didn’t realize just how experienced a colleague I had picked. Checking someone’s LinkedIn profile first might be a good idea, no? I did not. In this case, my error was only in my favor, as I picked someone with decades of experience working with developers. He’s an astute advisor not just about devops and the tech we work with, but also about interactions with others. I’ve brought him some interpersonal work dilemmas and he’s had helpful insight.
The biggest surprise for me was that this mentoring relationship turned out to be way more of a “two-way street” than I expected. What could I have to offer him, given that he has no particular need to troubleshoot a Jenkins build problem or learn how to use kubectl? Well, I’ve been a developer, a tech lead, and an architect, both doing the work and helping other devs do the work. That gives me a lot of visibility into and perspective on how dev teams in my area operate. And he’s outside of that area, so this is valuable to him. (Don’t fret if you don’t have that kind of experience, though – the perspective of a newer person is more valuable than you may realize.) We’re also working in partnership with each other, because with two different management chains, we have different sources of information, spheres of influence, and organizational contacts. We’re working out ways our teams can support each other’s efforts, and we’re introducing each other to people who can help.
Ask, ask, ask
Start by asking yourself the questions to determine what you are looking for from a mentor and how you imagine mentoring might look. Ask around to find a potential match, and ask for an introduction – if they don’t have time or interest, you’ll find out, and no harm has been done by asking. Keep an eye open for what you might be able to provide for your mentor in return (like sharing an interesting article or introducing your mentor to a colleague). You could ask your mentor outright if you can be of service in some way. Curiosity about yourself and others will serve you well on this quest.
Many thanks to both of my mentors, I can’t imagine the last year and a half without you. Thanks to our management for making the connections (and for being great mentors in their own right). And thanks to “baby G” for disrupting the status quo and opening up doors for me in the process – happy first birthday.
It is now April 2025, and I am fortunate to continue to have both mentors as friends. I have also stumbled my way into a few other mentoring relationships as well. I wasn’t looking. I’ve simply crossed paths with a few more people whose knowledge and perspective have made them great teachers, whether or not they realize it.
I’ve come to treasure those professional relationships where we can have a once monthly half-hour meeting on the calendar, with no prepared agenda, and we’ll invariably find more than half an hour of useful stuff to discuss. “Hey, I wanted to get your opinion on this…” or “so here’s the dilemma I’m facing…” or “do you have any advice for how I might approach…” or even “is it just me, or have you also noticed that…”
I’ve also been able to be a mentor myself for a few others, folks who have sought me out directly or through their management. But whether I’m someone’s formal mentor or not, I see it as a key part of my role to just listen and be present with others, and to offer anything from my experience that might be useful in response.
