Six Months of Managing

Hey! Thanks for reading! Just a reminder that I wrote this some years ago, and may have much more complicated feelings about this topic than I did when I wrote it. Happy to elaborate, feel free to reach out to me! 😄

It's been a pretty momentous few months for me at Reonomy. Like I mentioned in my 2015 in Review post, it's been the most professionally fulfilling job I've had, and looks on track to be the gig I've kept the longest (currently Adobe, where I was for about 2 years).

On that note, in February, I got promoted to Engineering Lead, and started work with direct reports. In July, I got promoted again to Director of Engineering, and now manage most of the engineers. The move from software engineer who spends most of their days "in the weeds" to one who mostly manages people is one of the more culturally loaded narratives in our profession, so here's some reflections/thoughts having been in this now for about 6 months.

I like it. A lot.

This wasn't a certainty, so I'm happy to report, I do!

More like Theater than Engineering

When asked about the gig, this is what I lead with: the actual, day-to-day work of running the teams has more do to with my theater background than anything I did when I was designing and writing software. Obviously I need the technical context to understand, assist, and communicate the needs of my team, but getting a group of smart people with various strengths and weaknesses, preferences, and communication styles to Voltron-sword a problem is exactly what theater productions are, too!

One of my favorite things in theater was seeing tacit fights over the role of a director. They get marquee status, their name is right there under the author's on the cover of the program. They get the glory, and are treated as the people "responsible" for the production in question.

In my experience, some theater directors really see their role as being "the vision" of the piece. They need to make sure their vision gets enacted! They tell actors how to act, designers what they're looking for in their designs, and otherwise make everyone's contributions fit their vision.

My favorite directors couldn't be described in this way. They recognized that everyone there is smart, capable, and will add to the production in ways they couldn't anticipate. If you wanted absolute control over every element, you should have become an animator. At the end of the day, it's the actors and designers whose work will stand there, why not incorporate their feedback? Provide backbone and leadership when applicable, but remember that the show belongs to everyone.

I approach tech teams similarly. None of my experience choosing software stacks or designing resilient systems is as applicable as my experience working with actors to achieve consensus on the meaning of a scene and how we could best convey it. Unsurprisingly, most of the best ideas came from the very people creating and embodying the characters, and most of those ideas came out at a myriad of points in the rehearsal process. I always felt the best directors accepted none of the credit and all of the blame, I try to approach this the same way.

A corollary to this is I don't think people who don't care about or enjoy "managing" should manage engineers. Lord knows I'm into technical geekery. I'd be happy writing software for most of my professional life. But the reason I'm enjoying (and hopefully succeeding) in this role is because I also happen to love of working with people.

Remember who does the work

I've been accurately accused of caring more about the people reporting to me than my laterals and/or the executives and investors above me. I understand the arguments for making your lateral or upper team your "first team," but I still don't entirely buy it.

One of the posts I most refer to is this one from jwz, with the very poignant line "one and only youth." The fact is, many of the people working for you are spending most of their waking hours in their one life making people up the chain disproportionately wealthy, often doing a high-skill thing they themselves couldn't do (very obvious in the case of tech workers). Apparently it's a thing to not know anything about a craft (e.g. computers), bark at people who've dedicated years of study, crack whip behind them demanding underspecified output (remember: you don't know their problem domain like they do), then feeling entitled to orders of magnitude from the wealth that work creates. I… just can't understand that mentality. You're managing people. They trust you. Keep them safe, guide them to fulfilling work, try to make them happy. What's the point of having any power in a structure if you're not going to make it great for the people most impacted by your actions?

Related: Where do great work environments come from? Who makes great places to work? There's an old Daily Show segment when Apple, accused of dodging taxes, went to testify to Congress and told them, essentially, "fuck you and your too-complex tax code! If you care about Americans, you'd simplify the tax code! Isn't that the real problem!?" To which the Daily Show writers asked: who lobbied to make the tax code complicated? It wasn't poor people.

So who makes a great environment? While everyone contributes, the person with firing power has a whole hell of a lot more influence on it. Use it responsibly, and you can make this job someone's best job.

Resources I Consumed

I've been reading a lot of management-ey books during these last few months to get a sense of how I can improve. I haven't read any that I'd call useless yet; I largely suspect that this is because I'm starting with people's recommendations and favorites. It's still a… process, to chew through them. Camille Fournier wrote a great post in defense of the "boring business book."

Here are some that I've read, reactions to them:

[The First 90 Days][10] — Michael Watkins

This was suggested by my CTO, Chris, and also where the word salad in the link above came from. There were a few valuable things I got out of this:

• Entering a new position might tempt you to burrow into what you're used to and already good at, but this can be dangerous. Embrace your new circumstances and quickly see what you need to do to be the most valuable. When I first hit Tech Lead, I decided the Good Meaty Features should go to team members, but I'd still have a hand in implementing secondary features.
  
  …but, I struggled to keep on top of even menial tasks. Furthermore, my PRs were coming back with a lot more comments of trivial things I'd missed. It was clear that I was both paddling harder and swallowing sea water. I immediately stepped back, reviewed PRs, and did out-of-band tasks (update the marketing site, analytics queries) and left the product development to the team. Turned out they were plenty fast without me, and liked having the codebase be property theirs.

• STARS Framework was an interesting way of modeling phases of a company.

• Appreciate the emphasis on securing early wins, understanding alliances, and the importance of doing a bit of recon before committing to any plan of action. All common sense, but defended/articulated well here.

It's pretty clear they're writing this book for Tactical Action People: virtually every chapter has three "fill in the squares of this table" exercises.

[The Hard Thing About Hard Things][11] — Ben Horowitz

This is probably the one I'm most conflicted about. This suggestion came from my COO, Brooks. This had the most "screencaps because I'm fucking retching here."

That said, his chapter defending 1:1 meetings was exceptional; it had some great examples of prompting questions, why they are valuable, and how to run them. I also thought "Good Program Manager, Bad Program Manager" should be read by more people in software to get a sense of what that role even is. Same with "Peacetime CEO, Wartime CEO."

Of all the ones I read, this is the most specific to tech and tech businesses. More than trusting or believing his accounts of how it all went down, watching how he frames those events and the characters involved does a lot to illuminate how the VC class thinks of themselves, the industry, and its history. You can think a church is worshipping clearly false idols but still find value in reading their holy texts, especially if you don't have much of a choice but to have to deal with them.

[Getting to Yes][12] — Roger Fisher and William Ury

If there's one book of these that I can recommend to anybody, for any reason, it'd be this one. I learned about it from a post I link in my Engineering page as a favorite, Don't Call Yourself a Programmer, And Other Career Advice by Patrick Kalzumeus. Fabulous post, fabulous book (you should also see Patrick's article on salary negotiation, which helped me increase my comp by nearly double since I moved to NYC.

But yeah, this book has advice you already instinctively know and know to work, and helps you get to better outcomes, faster. It's good for virtually every stalemate or conflict you find yourself involved in, responsible for, or mediating. It's a great reminder to focus on needs being met (rather than positions held) in any conflict.

*extremely actor voice*: "what is my motivation?"

[Five Dysfunctions of a Team][16] — Patrick Lencioni and Kensuke Okabayashi

Also a recommendation from COO Brookie. I enjoyed this, even though I didn't always agree with it. I got the Manga Edition because it's more fun, and lets be real: most of these books can be fit into 30% the size, and get puffed up to Book Size for saleability.

The five listed dysfunctions are a great articulation of team failure you've already witnessed, and many of the suggestions to break out of them are helpful. I disagree strongly with the notion (mentioned above) that your highest-level team should be your "first team." Obviously don't put a single team's goals above collective interests of the organization, but how the hell will you effectively and honestly lead people if you view the ones who trust you with their careers as second to a group of fancy people?

I think a more daring version would be sure to dive further on what is meant by "embracing healthy conflict" by investigating and/or categorizing the various ways that conflict can be navigated to properly facilitate meaningful outcomes. There are a ton of people who don't fit the Aggressive Metaphor land of sharks and wolves and all that crap who aren't afraid of conflict, have tons to add to a discussion, but are put off by people playing Debate club and who relish being argumentative and taking up space. Lord knows there are meetings I sit out not because I have nothing to say, but because I can't get a word in with 6 usually-White usually-Guys who love to hear themselves talk so damn much.

A really daring version of this would then follow up with how this intersects with people's biases. WaPo did a great piece called Famous quotes, the way a woman would have to say them during a meeting that illustrates the very studied fact that women are frequently called abrasive or told to step back for merely expressing opinions. This is deep and intersectional, and there's no way Lencioni is touching this with a 10-foot pole (either because he doesn't know, doesn't care, or most likely because he thinks it's too hot a topic to include in what he hopes to make a widely-appealing bestseller) but I feel telling people "you should hash things out!" but not demonstrating any knowledge of this is setting up non-assholes (so, not me) to fail.

On the docket to be read next:

Turn This Ship Around! — L. David Marquet

Mentioned in the Camille Fournier post I linked above, and recommended by a co-worker.

High Output Management — Andrew Grove

Mentioned on my Twitter feed and seconded by COO. Started it, so far so good.

A book on Appreciative Inquiry

My mom did her Master's Thesis in Organizational Development on this, so I'll probably be reading a book or two on it (I asked her to pull out her thesis, but this was the early aughts and it's surprisingly hard to find a copy!).

Also love that the acronym for this is AI.

Common themes to all of them:

• This has been a Cultural Experience. There are a million narratives about Executives and Founders being these special creatures with the Great Gift of risk-taking and for this they deserve to rule over the typical, Unspecial masses ("they should be grateful to us for giving them jobs!"). Most of these books are massaging the hell out of these people's very delicate, oversized egos, and like anything else that isn't made for you, you learn a lot from surrounding yourself with it.

• Most of these are written at the 8th grade level. If you believe my understanding of the above, most of the folks who read this like gospel aren't nearly as smart as they think they are.*

• Per the above, an even larger number are complete wannabes. But they're wannabe's who can spend $14! So they're written for them too.

* = FTR: I don't mean to imply that not being smart means many of them don't deserve their business success, or are bad people or anything (many are, but not because of their tiny intellects). Wasn't Dave Thomas a High School dropout? Seems like a decent enough guy, and Lord knows I love my Wendy's. I'm just saying success in business does not necessarily correlate to these Atlas-like images most of these people have for themselves.

Overall

I've still got a lot to learn. I'm blessed with two fantastic teams, and a supportive boss. I don't know what work life after this company looks like: continue management and/or director-level duties? Go back to the technical side? Found my own company!? But I can say that I'm grateful as anything for this experience.

If I make it to 6 more months, that gives me 2 years at Reonomy, making it surpass Adobe as the longest gig I'd have had. Here's hoping it continues to be such a journey.