Managing the First Year

Thoughts on being a new data science manager.

I became a manager for the first time by surprise.

I had been hired to be a “data scientist” for the first time, after years of doing data science work with different titles. During my first week, I spoke to my manager only once on the phone, as she was out of work with a sprained ankle. So I spent the week getting to know the team, thinking I was coming in as a senior data scientist.

It was only in my second week, as I spoke with my manager more that I understood that no, I’d been hired to replace her as the team’s manager.

During the 18 months I stayed in that role, I learned a ton about management. I read thousands of pages on management and made some really big, stupid, mistakes – including one that literally interrupted my honeymoon on the beaches of Croatia.

I started this writing project just after I left my management role, when I moved back into individual contributor (IC) work when I came to RStudio. As of this writing in early March 2021, I find myself in the early stages of moving back into management at RStudio.

So it’s worth saying up front – I’m not an expert on management and putting this out into the world is a little petrifying. I’m sure I more big, stupid mistakes to write about 18 months from now. That said, my first year managing taught me many lessons that I’m sure will help, and maybe others will find a few of the things I learned useful on their own management journey.

Managing the first year

I was on my honeymoon in the old town of Split, Croatia, known for its old-world charm and stunning azure waters. My new wife and I were staying in a tiny walk-up flat. The most remarkable feature of this single-room apartment was the bathroom, which was enclosed solely with a glass wall, privacy provided solely by gauzy purple curtain.

And though we were close enough to the beach to hear the seagulls caw-ing out the window, I was hunched over in the unlit stairwell of the building, listening to my voicemails and reading emails about the managerial crisis that was unfolding back at home.

One of my direct reports had made some fairly substantial mistakes in a set of charts that had gone to a client. Mistakes that reflected that we, the supposed data experts, had no idea what was actually going on in the data.

At the time, I was around 9 months into my tenure as a new manager, managing a team that had grown from 3 to 6 analysts and data scientists, providing analytics and data science support to a large federal contract at our consulting firm.

As soon as I’d realized that I was going to be thrust into the world of management, I’d started trying to figure out how to learn. I knew that leading a data science team was going to be very different from doing data science, demanding new kinds of work and new skills of me.

But, I wasn’t sure how to learn to manage…or even what management really was…or how to learn.

I’d had a few good managers over the years (and some bad ones), but didn’t have a clear mental model of what management was or how I could get good at it. Certainly nobody was knocking down my door to mentor me in management skills, and no one was going to hire a Trillion Dollar Coach for a first year junior manager.

So I did what I do best — I turned to books. I read management books, biographies of managers, deep dives on companies that seemed to have figured something great out.

Most of those books were bad (or at least over-long by half), but some were good. I developed a reasonably coherent mental model of what managing is.

And yet – I was still crouched in a stairway, on my honeymoon, seagulls beckoning, listening to voicemails about data values being too big by half and categories not making sense.

I write all this to share that having a theory of good management has been important to me, but it was wildly insufficient. Management is a craft more than an art or science – and like any craft the trick is in the doing.

So, I hope you’ll get some helpful mental models out of this (partially finished) essay – but even the best mental models are only modest protection against ending up in a dark stairway, listening the seagulls, wishing the line plots would just go away.

What is “management”?

As best I can explain it:

Good management is a flywheel generator — it clears obstacles to achievement of individual contributors (ICs), creates an environment of safety and growth, finds and aggregates resources the team needs, and ensures that everyone understands what the team is doing.

Reading this clever and finely-worded definition fills me with the warm glow of a concept well-encapsulated. But let’s be honest, you — reader — are reading in hopes of being a better manager, or maybe even more likely, understanding why your manager is so bad.

If you’re looking to change the circumstances of your management or managing, this definition is maddeningly vague. That’s largely because the term management covers such a broad range of activities that it’s somewhat meaningless.

My experience was at the most junior level of management – directly managing a team of 4-8 data scientists.^[Sometimes called “line” management for…reasons…] I’m sure that my day-to-day work shared some activities with the CEO of the company, some 7 levels in the hierarchy up from me, but I bet not a lot.

I’m proud of the work the team did during the 18 months I managed them. We produced a lot of valuable data analysis, and moved a lot of work into R and Python (yay reproducibility!) that had been done in Excel and Tableau.

One curious aspect of that time is the the inverse relationship between my level of pride and my level of personal involvement in the output. The weeks after the honeymoon interruption, when I tried to do the work of the whole team have a dark cloud above them, while the time I talked to a direct report who had consulted a colleague and solved a thorny visualization problem while I was busy doing other things glows in my memory.

Roles of a manager

I have no direct experience with anything other than the most junior levels of management, so I’m going to stick to what I actually know. As a first-level (line) manager, my work mostly fell into five mostly disjoint roles:

For me, resources management was the hardest. As an IC, the amount of work is more-or-less fixed, and the choice variable is how hard you work/on what. As a manager, the work content, amount, level of burn the team is under, are all choice variables.

As the people you manage get more senior, the first of these to drop away is the project management. With more senior people, you just help guide people and trust them to do more of their own direct project management.

One thing that was entirely apparent was that my prowess as an IC mattered only to the extent it made me credible at these other things.

If you’re a highly skilled IC, you’ll probably be better than others at understanding what has to happen in terms of collecting requirements and setting schedules, and you might be better at mentoring and coaching if you’re doing direct teaching.

Some people believe the opposite to be true — being too good at IC work makes you less able to coach people who aren’t such naturals. I’m somewhat skeptical of this claim. I’ve seen too many people who are both amazing ICs and teachers and coaches (particularly in martial arts) to believe this is true.

I do believe there is one big distinguishing feature between people who excel in a management role and those who struggle — they have a theory for why people (usually based on their own experience — as an example or counter-example) are good at their job. They might not use that language — but they’ve thought about why they’re good at what they do.

This thinking is the raw material of good managing. Turning it into actual good management requires intentionally, willpower, and a lot of generosity. What it does not require is any sort of “natural inclination” — beyond the desire to do those things.

I should also say there are occasionally amazing leaders who are great leaders simply because they are so personally astounding and don’t do any of the things I describe here. I am not one of those people and you probably aren’t either. If you are, I’m shocked you started reading this. Either way, kudos and stop reading — you do you.

Managing is all about feelings

As a manager, you’ll spend a good bit of time managing your direct reports’ feelings and concerns. But first, it’s really important to address your own.

Being a manager will bring out and magnify all your insecurities, fears, and misguided thoughts. You’ll get shockingly little feedback from anyone on how you’re doing. And worst of all, this will all be visited on your direct reports.

I can’t remember where, but I once heard that “organizations magnify the worst traits of their leaders”.^[I think it might’ve been this episode of the excellent Start Up Podcast.] I have seen nothing that makes me think this is anything less than 100% true.

So my only piece of truly directive advice for managers:

Every manager should do therapy/counseling.

We all have traits and quirks that are maladaptive in a management role. Therapy won’t fix them, but it can increase awareness of them, and reduce the likelihood you’ll unwittingly perpetuate them upon your team.

Respect the power you’ve got

How does it feel to get a message saying “can we talk?” with no context from your manager?

[Undeveloped notes for future work/random bits that don’t fit in yet below this point.]

So why would you want to do this if you really excel at IC work? To me, the most compelling reason is to gain leverage. Leverage is the ability to get a lot from a little. In Silicon Valley, they love to throw around the idea of a 10x developer — that is a developer so genius and prolific they are literally 10 times as productive as most others. Let’s take this idea seriously just for a second. Let’s say you’re a 10x developer, then you could plausibly replace 10 people with yourself. So if you manage 11 people, you’ve now exceeded your own personal output, and let’s be real — you’re not a 10x developer (because they don’t exist).

Mentorship and Coaching

Mentorship and coaching can be a big part of managing, and one of the most rewarding.

Who am I? There are many different identities that you’ll have to manage between yourself and your direct reports. I always found that I struggled to convey expectations as high as I have for myself to my direct reports. I excused slow work and responded kindly to weak excuses for poor outcomes.

I definitely fell victim to trying to be too much of a friend and not enough of a coach. Meanwhile, there is also the role of managing tasks vs career mentorship. There are many times where the demands of the immediate task is in conflict with the career wishes of the direct reports. For example, we had projects that really needed to get done — my direct reports wanted to learn the technology we were using, but what we really needed was for them to just get it done. How do you balance the time they need to develop new skills with the requirement that they do the actual work ahead.

(Care personally vs challenge directly)

What is a direct report? How does the langauge matter?

Managing New Workers/Interns

Extra challenges

Balancing Autonomy For Direct Reports

Still hard, harder for younger workers.

Whose interests do I represent?

This is a surprisingly difficult question. As a manager, you have two ways to look — up, and down. Looking up, you have responsibilities to the company, your bosses, the rules and regulations (and potentially laws) that govern the way you work. But you also have to look down to your responsibilities to the people you manage.

Unlike looking up, where the entities involved are somewhat amorphous and impersonal, looking down to the people you manage involves their real concerns. For example, I was on a consulting project that required a Public Trust — the lowest level of clearance possible in the federal clearance process. However, one of my colleagues was as dual citizen, and was forced to give up her other passport in order to get her Public Trust. Unfortunately that meant that she couldn’t go home to visit her parents, as her home country required that dual citizens travel there only with their passport.

These issues become intensely personal.

Be aware of the fact that if you’re mentoring younger people in particular, they probably don’t understand the dynamic of a workplace and that they have to protect themselves from their employer. As a high school food service employee, I once purchased and brought home a pizza on which I’d messed up the order, because I thought I had to — and I have a severe dairy allergy.

In very real terms of power and privilege, the people who work for you almost certainly need more protecting from the company than the company needs protecting from them.

Additionally, people know when your number one priority is looking out for them and they will respond in kind.

Extractive vs growth organizations

Limitations on what you can do as a junior managers

Meetings

Are really useful. They’re your primary tool as a manager.

DIsdain for meetings in is toxic.

They can get out of hand, but just be mindful. Do a meeting Marie Kondo periodically.

1:1s

Are essential How to do them well?

Team Meetings

Also essential

Easier to push on barbell than broomstick (group brainstorming = :vomit:)

About Setting and Communicating Goals and Priorities

Book Recommendations

I’ve read many, many books on management. I think most are not terribly useful – often providing 3 pages of insight in 150 pages of text, or providing a mix of theory and practice that ends up being insufficiently useful on both dimensions.1

I’m not going to badmouth any particular books, but I’ve read most of the currently-popular management books. So if it’s not on this list, I’ve probably read it and don’t think it was worth the time.

Your mileage may vary.

Theory

These books strongly shaped the way I think about what management is and what a manager is doing.

You’ll notice that I lean towards older books on theory – both of these recommendations were written before I was born! While the computer, internet, and emote work have changed the practice of management, I don’t think the underlying theory has changed at all.

I strongly believe that the core messages of these books are still fresh and important, but I will note that some of the commentary and assumptions, especially around gender, have not aged well.

High Output Management (1983)

Andy Groves’ classic on what management is and how to measure a manager. Light on practical advice, amazing for forming a mental model of management.

Mythical Man Month (1975)

Fred Brooks’ tome on communicating across large groups and software complexity. Not strictly about management, but deeply impacted the way I think about the optimal size of working groups and how to help people be productive.

Practice

This book helped me figure out what to do every day as a manager, providing concrete advice on how to do onboarding with people you’re newly managing, conduct 1:1s, and more.

Radical Candor (2017)

Kim Scott’s book on how to provide direct and meaningful feedback to direct reports across a wide range of topics and venues. As a new manager, providing feedback was one of the strangest and hardest things to learn.


  1. I am keenly aware of the danger of speaking ill of others writing, given my own limitations as a writer. But if it can be useful to you, maybe it’s worth it.↩︎

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