From Individual Contributor to Leadership

I’ve gotten a lot of pokes the last few years to discuss how I transitioned from an individual contributor (Developer/Architect) to Manager/People Leader. It’s sort of a windy road for me personally, but one that I’ve grown more and more rewarded by.

There I was, a Lead Architect/Developer — coding, speaking, working to inspire and drive change, not just at work and on technical things but with people. We were in the middle of yet another re-org, and as I was sitting there looking at our little team and the fact that we were suddenly, well, leaderless after the re-org.

I went to my boss’ boss — or basically to the highest-ranking person that was attached to our little team — and I said (in more words), “We don’t have a leader setting the big, scary mission and fighting for us, and this is terrible. It’s terrible for the people who have been here fighting a hard fight for year; it’s terrible because we now have no representation in financial/HR discussions. Pretty much, it’s disengaging, bad leadership, and something needs to change. The people in this org don’t deserve that.”

I was asked, “It sounds like you’re volunteering. Do you really really want to be a manger?”

My only response was “I want to do the right thing for the people. I don’t care what it involves.”

“We don’t think you can manage/lead people.”

“If I fail, you can fire me and salt the earth.”

You do that, bill.

So that’s the super succinct version of how it went down. I mean, in reality I was already doing leadership activities, just not the manager activities (you know, like reviews, budgets, headcount forecasting, firing people, etc).

Fast forward a few years, many miles, and a lot of introspection and thought later, and I can see that this was the path I had already been on for a long time. For as long as I can remember, this has always been a cornerstone for me:

“Do the right thing for the people. I don’t care what it involves”

I said in my boundaries post:

“I’ve always been the ‘go with it’ person. Whether in personal, professional, open source, community work, etc. I took pleasure in the fact I pictured myself as going through life like as a monkey with a blindfold strapped onto a four-stage rocket. “Fuck it, it’ll work out.”

Even in my community/open-source roles, I’ve always been focused on the people/empathy portion of tech and work. I’m insanely passionate about user experience & design, and I’m constantly on people about communications, empathy, belief and inspiration.

Strengths

For those of you unfamiliar with the Gallup “Strengths” test (all Rackspace employees take it), it’s basically a set of questions you have to answer “in the moment” to roughly suss out what your top 5–10 strengths are. This doesn’t slot you into a particular role or anything.

It’s more of a set of words/language/terminology for you to say “Ah, so I’m an Activator. This gives me a term for how to describe my instinctual response to stimuli being GOGOGOGO.” If you read a bit more into the individual strengths, it also gives you insight into what sets work best in what scenario, and what are the pros/cons of each (for example, my positivity sometimes drives people nuts).

Pinkie pie and me are tight, fools

The reason I’m mentioning this is that it’s fairly normal to see the same top five strengths for many people in a given type of role, especially developers. What’s interesting is that as I went through some leadership training, I discovered that while, yeah, I had some of the core ones for “bro write code k,” many of them were actually people-leader ones I hadn’t fully explored.

Also, it’s handy ‘short hand’ to be able to see how you might react to a given person or situation, or — in the care of leadership — know where your gaps may be. Part of being a people leader is a requirement that you be very self aware. You’re no longer just managing your own life, but the lives of others. And if, for example, you are a person (like me) who has “harmony” dead last in their strengths list, there’s a real chance you can bulldoze people who are conflict avoidant.

Having this shorthand available and widely shared gives you and the people you lead shared context. Shared context is really important.

So here’s my top 10, and a short description of each (oh yeah, the strengths stuff is copyright 2000, 2006–2012 Gallup, Inc. All rights reserved.):

• Futuristic: People who are especially talented in the Futuristic theme are inspired by the future and what could be. They inspire others with their visions of the future.
• Strategic: People who are especially talented in the Strategic theme create alternative ways to proceed. Faced with any given scenario, they can quickly spot the relevant patterns and issues.
• Activator: People who are especially talented in the Activator theme can make things happen by turning thoughts into action. They are often impatient.
• Ideation: People who are especially talented in the Ideation theme are fascinated by ideas. They are able to find connections between seemingly disparate phenomena.
• Developer: People who are especially talented in the Developer theme recognize and cultivate the potential in others. They spot the signs of each small improvement and derive satisfaction from these improvements.
• Positivity: People who are especially talented in the Positivity theme have an enthusiasm that is contagious. They are upbeat and can get others excited about what they are going to do.
• Communication: People who are especially talented in the Communication theme generally find it easy to put their thoughts into words. They are good conversationalists and presenters.
• Restorative: People who are especially talented in the Restorative theme are adept at dealing with problems. They are good at figuring out what is wrong and resolving it.
• Empathy: People who are especially talented in the Empathy theme can sense the feelings of other people by imagining themselves in others’ lives or others’ situations.
• Belief: People who are especially talented in the Belief theme have certain core values that are unchanging. Out of these values emerges a defined purpose for their life.

The top five really aren’t surprising for a developer/programmer/etc type. Where it gets interesting is the last five combined into the mix means I’m actually less of a command-and-control type and more of a lead/inspire/long-view person, and that’s actually a pretty good set to have stepping into a people leadership role.

I share this because it dovetails into the things I’ve had to learn/adapt/change while becoming a leader. When you have a set of things you are “good at,” they are contextual. For example, when you are an individual contributor, being an activator is kind of a good thing. Your default is Go. Do it. Do it now! As a leader? You gotta dial that shit back and reset it to be focused less on problems (break/fix/bug) and more on strategy and “managing up.” Always being in ready-shoot-aim will burn out your team.

Early Pitfalls and Anti-Patterns

So swapping into a leadership role isn’t something you should take lightly. You should also immediately stop and read two books:

• The First 90 Days
• What got you here won’t get you there
• Go and seriously read everything Rands has written. His essays on 1:1s and leadership in general are worth every single minute of reading.

My mistake was skipping the first book. Given I was moving into the role in the middle of a massive shift/change in the business, I was stepping into a bonfire. So my activator took over, and I immediately went into break/fix mode instead of listen/observe mode. This is a major pitfall new leaders fall into. Part of it is that your instinct tells you to fix things, and second is you’re in a new role, so you have to prove yourself as rapidly as you can. Bad. Idea.

My first leadership meeting

I also didn’t take the time to think about boundaries. I was used to the high-activator, always-on, always-available model that had driven me my entire career. I would call directs randomly, off hours to check in with them, to see how they were doing. I would send emails late into the night and ping people on chat. You need to reset your damn boundaries and clearly communicate expectations to your directs/organization.

If you (like me) are a manager of managers, you also need to realize that you can’t just jump into something or discuss something with individual contributors without letting their actual manager know! Christ, the number of times I accidentally went around my managers to their directs (with the best of intentions) was astounding. It’s demoralizing to your leaders, and it actually confuses the hell out of individual contributors on the team. “My boss said this, but my bosses boss said this, and he trumps my boss so…” You just gelded your manager, congrats.

Listen. Actively Listen.

You need, I guarantee it, to work on your listening skills. Stop what you’re doing and read up and practice Active Listening. You need to be able to play back what people are saying, sort through the things that are ideas, suggestions, and actions. If you don’t do this, it’s super easy to be sitting in a leadership meeting and be like, “Shit, I think the SVP wants me to go light a car on fire and I should go do that.” In reality, they probably don’t want that. It’s not an action, and they were just thinking out loud.

This also improves how you communicate in general. You have to become self aware of words you may use, like “should, can’t, impossible, never,” and the fact that your job is now to, frankly, avoid those types of absolutes. Well, not avoid — use sparingly. Your job is to make the impossible possible, take a long view, and nothing pisses VPs off more than a passionate director (me) blasting out “No, we can’t do that. It’s impossible and a terrible idea.”

Now, the statement might be true; however; back up: Does everyone have your same context? Do they have the same view on the problem domain? Is it really a terrible idea, or one that needs to be sussed out and explored before you kill it with fire? Ask yourself: Do you know everything, or are you reacting in the moment on a lizard-brain level?

On the flip side, too much avoidance of absolutes and concrete statements/decision making basically means you spend time in meetings talking in circles and avoiding the elephant in the room and walking away wondering what the fuck just happened to the last two hours. But the art is in the delivery and communicating in a way that doesn’t piss people off or make them shut down.

Also, correct!

This is somewhat interestingly where my “belief” strength betrays me the most. I’m passionate, vocal, and I believe to my core in what I am saying. This means I have a lifetime of black and white absolute and blunt communications style defaults. You gotta unlearn that. Belief and passion good. Verbally punching someone in the throat is a dick move, and also undermines you and the people that report to you.

Fluidity: So, I can be pretty fluid, almost mercurial in my ideation/thinking/planning. Guess what, though? That’s fine to an extent, but what your people deserve is stability and clarity. If you’re brainstorming and thinking clearly, communicate that’s what is happening and for people to participate in the process but don’t take it as things are changing, etc. You make people nervous/scared that you’re going to pull the rug out from under them.

Learn conciseness. My writing style is very close to my speaking style. Guess what: not really concise (sorry, not sorry). Your job as a leader is to learn how to speak and communicate in a concise, empathetic way. Not randomly jabber and bury your lede. Sure, sharing is caring and context is king, but too much sharing, too much context, and people shut down/tune out/browse Reddit.

Don’t undermine your leadership. I tripped on this early on. Someone would say, “Yeah, manager/director/VP is a dummy,” and I’d nod or agree or something. Guess what? This may build rapport with that person, but it will build a culture where people are super connected to you and rapidly dismissive of those above/around you. So when you’re all in a meeting about changes or shifts or something else, people think it’s OK to hop on the backchannel and lob bombs at the person you’ve unwittingly undermined.

Don’t vent down. If you’re a manager, or director, or VP? Guess what, you don’t get to join the #bitching channel in slack or at least participate. You can watch, you can maybe help defuse, but you don’t get to join in. You don’t get to vent down the chain of command. Why? You undermine yourself, your team, and your peers and leadership. You can vent up all day long to your boss. Never down (and never, ever while drinking… that shit shows up on YouTube).

Avoid, at all costs, wading into the fray of a project, meaning even if you could code it, review the code or weigh in on design decisions, you probably shouldn’t. You have a title and a role, and that carries Authority with it. More junior team members aren’t equipped to understand that if you’re commenting on a code review or submitting a patch you’re not invoking “do it my way, now”. You disempower them and unconsciously overrule them.

So with all the mistakes I made, don’t make the same ones. I have a tendency to learn things the hard way. I’m the type of person who, when confronted with a brick wall, will beat his head against it until it crumbles. This means I’m tenacious, but I sometimes miss that there was a better approach through the damn wall.

You’re going to lead people, inspire them and grow them. Your job is now to change not who you are, but how you approach, think, solve, collaborate, and communicate.

No seriously who farted?

Managers vs Leaders

You should take a moment and read this stunning interview on “Impactful Engineering Leadership” with Jessica McKellar, someone I really look up to. It makes some really amazing points that I think tie into my opinion that there is a significant difference between management and leadership.

Here’s the two bullet point version:

• Management is a set of skills and duties that can be learned / taught. There is generally low variance in the sets of skills and duties — for example, budgeting, forecasting, hiring, firing, one on ones, etc.
• Leadership is much more about things that can’t be taught or learned on its face. It’s highly variable, and not all managers are good leaders. Leadership is about inspiring people, charisma, vision, values, and humility.

The two are frequently conflated. By default, we refer to Managers, Directors, and Vice Presidents as leaders/leadership, because they are the ones making strategic decisions and providing directional guidance. However, having that title doesn’t make you a true leader.

All of the leaders I’ve worked with in my career have a set of common traits:

• They have, or can rapidly create, a vision. They look to the future and can see the micro and macro trends/influences within an industry or organization.
• They can inspire. In order to do this, they know how to craft and deliver a message that is tailored to the audience receiving it. For example, a good leader knows that what may make sales people excited and rally to a thing is not the same that excites and rallies engineers. They know when to water it down (mixed audience) and when not to.
• They have charisma and empathy. They may not be an extrovert. Heck, they may not be the life of the party. But when they’re talking to you, you feel like the center of the world. They understand emotions and what drives people and can dig into personal motivations and incentives.
• They can dive in and “go deep” into a domain, but maintain the higher-level mental chessboard, so they can connect the two.
• They can articulate and contextualize a vision, mission, and set of values.
• They are humble. Humility and vulnerability come hand in hand, and the best leaders I know are humble. They know that they are not measured by their work, but by the work of those they lead. They can be vulnerable and open up about their fears and failures and learn from them.

The key here is that management is more of a clearly defined, learnable “thing,” while what I’ve listed above for a leader are more about the qualities of the person in the role. I have met more managers who do not fit any of the six things I listed above, but are still perfectly capable and skilled managers!

On the flip side, I would not look to those managers to inspire me or to drive me. They’re more of a mechanical gating system: You know what you’re going to get, and they’re typically very consistent. Weirdly, they also know more about the mechanics and politics within a given organization and can unlock things you find baffling.

I have met leaders with absolutely zero management skills, and the same set of thinking applies there. I am not going to go to those leaders to cut through bureaucratic mud pits filled with the howling dead or to negotiate for a raise, but I might bring them in to advocate for me or cut through the bullshido.

Many of the leaders I’ve met and worked with are also baffled by the mechanics, politics, and biases of an organization. I think some part of this is the focus on the future and connecting with people. I’ve been in meetings where a leader I respect is frustrated by something that, when we dig into it, we find that there’s an institutional bias or political force blocking it. Meanwhile, a manager in the room is smiling like a cheshire cat.

Me? I aspire to be a leader, not just a manager. I want to be the person creating a vision, a mission, and rallying people to that thing. I want to be (and stay) humble and to be able to — after, say, a failed project — stand up and have the courage to openly admit that I made a mistake.

And truth be told, I really love the management bits, reviews, one on ones, guiding and building people, negotiating with other teams and managers, managing “up”, setting strategy and vision. I feel just as — if not more rewarded see the fruits of their work and raising it up as I did building it myself.

My view is this: As a leader, if there is a success it is the team’s success, not my own. I simply empower them to get it done. I stay out of their way, focusing on their careers, listening to them about their lives, and finding things that may block them (or get them budget for headcount).

If, however, there is a failure, it is mine, not the team’s. I and I alone am responsible for a failure. Sure! There could be a million different contributing factors, but at the end of the day, it’s on me.

Sorry Vader, I’m the one that *hurgh*

When I signed up to be a leader, I signed up to be a leader. It was a bit terrifying. After all, it’s a completely new job with completely new skills (as Rands would say). It’s night and day as compared to what you were doing before. Adapt.

A good leader is people and team first, company second. As I said in Everything Dies:

I would add that my job is to ensure their future outside of the current work they’re doing or the company that pays them. I’m working with people and those people deserve a future that doesn’t include me, the company, the business unit or backlog.

This is career growth, not position growth, if they grow and they leave, mission accomplished.

The worst leaders and managers? The ones that prize the company, tenure, and other things above the fundamental needs of their people.

Reading & Learning

In addition to what I’ve already linked to in terms of reading and learning which I’ll re-link here, here’s some additional color and training:

• Impactful Engineering Leadership (article)
• The First 90 days (book)
• What got you here won’t get you there (book)
• Rands in Repose His essays on 1:1s and leadership in general are worth every single minute of reading.
• Situational Leadership (training, books) — Trust me, you want this. It gives you more of a vocabulary and a set of triaging mental tools to be able to calibrate conversations you have and identify risks / motivations / skills.
• Crucial Conversations (books, training) — basically, how to communicate better, how to make a “safe place” for conversations and more. Do it.
• Precision Q&A (books, training) — You need this for “managing up”. As you move higher into an organization, or find yourself in meetings you’re going to want to hone your ability to quickly triage what’s going on, how to be concise when answers the actual question being asked, etc.
• The hard things about hard things (book) — Mandatory reading for leaders in tech. Lots of great learnings about shared context, calling a thing what it is, and making hard choices and failing.
• Every book by Brene Brown. Not joking, she changed a lot of how I act / communicate.
• Protip: Go to any management/leadership training your work provides. Not only do you learn, you actually end up networking and building relationships.
• Get speaker training. If you’re not already an experienced public speaker you should try out a toastmasters or get one on one/group training. Your job as a leader is to communicate. That means knowing how to present and craft a presentation.
• Try a program like Landmark or their peers. You have to build new muscles in communications, empathy, professionalism, presenting yourself.
• Take a class, or read a book on sociology and psychology. You can’t lead people if you don’t understand how they work.
• Learn emotional intelligence. You jerk.
• Get a therapist — not because you’re sick, just someone you can talk to and bounce ideas and thoughts and feelings off of.
• Learn and practice Active Listening. Right now.
• Study mental models, OODA loops, etc. This help frame problems and speed up your ability to root cause and triage.

Thanks, Obama!

Finally

Keep your sense of humor. Your job as a leader and manager is hard. The people who work for you have hard jobs, too. You are in literal control of human lives. This means it’s easy for you to Get Really Serious Ice Man, or it means you can get depressed if you let things bother you.

You have to keep your chin up and learn from failure, and you have to keep a sense of humor. What good is being a leader over five, ten, a hundred people if you can’t all share a laugh. What’s the point if your director can’t dial into a video call wearing a rubber horse or batman mask to discuss quarterly earnings?

Don’t lose you.

All in all; becoming a leader and the pains and the changes and the growth has been one of the most rewarding things I’ve ever done in my life.

PS: I’m saving “Politics, culture, and authority” for another post. It’s probably another 3000 words, to be honest.

Todays standup attire