Publish date: Dec 19, 2019
When I started managing, I knew I was learning a craft. I was willing to suck at it. I was willing to put in the work every day for years to someday be great at it. I accepted that there were no shortcuts or hacks to becoming a great manager overnight. And I laughed my ass off a few years later, when I noticed there was one thing that did truly make me a better manager almost instantly: reporting to Charity Majors.
I don’t say any of this to suggest that Charity is a flawless manager or person. She gets powdered apple cider mix all over the water dispenser and the Keurig, and that is only her most trivial flaw — there are others, they matter. The things she says on Twitter often make me 😍 but sometimes they also make me 😬 😶 🙃 🤐. And nearly everyone who tries to emulate Charity’s management style wholesale will flame out in grand style — she is better than anyone I know at compensating for her weaknesses with her strengths, and her strengths are far to the right of the bell curve.
I don’t profess to be a flawless manager either. When I say “made me a better manager,” I mean that I became a person demonstrably more able to hire a great team, make that team happy and successful, and help that team quickly ship, maintain, and improve great products. But I have a laundry list of things I continue to work on or hope to change in the future — I was not wrong that managing well is a craft you dedicate yourself to working at continually for many years.
The seven things
These are the top things Charity does that 1. are relatively rare among engineering managers I know and 2. gave her a tremendous amount of leverage to make me more successful as a line manager:
Communicate more — way more. I remember when I first started at Honeycomb, I spent a fair amount of time wondering, “Why is she talking to me about this???” Charity would sometimes DM me with seemingly random observations a few times a week about the product or team. In 1:1s she’d give me updates on her thinking about aspects of the business or product that sometimes seemed above my pay grade or outside of my domain. She’d also ask for my opinion on team issues, even when she didn’t really need my buy-in to move forward. I thrive on a huge amount of context, so I liked it, but I couldn’t help but feel like I’d lucked out and received a gift in the mail intended for someone else.
Now I look back and see that those conversations were the foundation of our working relationship. I joined Honeycomb as an IC at first, and I think in the beginning I was very quiet and cautious and a little hesitant about everything. Those early conversations with Charity gave me the context I needed to understand where I could be most useful, but they also conveyed trust. They suggested that my thoughts and my voice mattered (one of my most consistent flaws is that I guess wrong about when it does matter and when it doesn’t all the time). We figured out how to talk to each other. We figured out how to make sharing the easy stuff truly easy, so that only the hard stuff needed to be hard. We established that baseline of what normal sounded like, so we could tell when things got off track.
Stand for something, tell people about it. Charity gave a keynote at Velocity 2016 called A young lady’s illustrated primer on technical decision making. It’s full of great pointers on making technical decisions, but the underlying worldview — that technology and engineering teams exist to serve the business, and that all too often we fail to consider the business’s best interests when we make decisions — felt both 100% correct and refreshingly honest. Charity has opinions, she picks a side, she lets people know what side she’s on.
This matters for a couple of reasons. One, founders and execs have opinions; they all have sides they’re on. When you know where your founders stand on potentially controversial things, it frees you up to act with less friction and less worry. For example, I know Charity generally shares my distaste for credential-based gatekeeping — and I know because she’s said things about it in public, more than once, not just to me in a 1:1. Everyone who is going to question my decisions heard the same thing. And that makes it safer for me to go to bat to, for example, interview a candidate that seems promising but doesn’t have brand name companies or schools on their resume. Clearly stated, public values free up employees to aggressively act on them instead of having to slowly pen-test the organization looking for resistance.
Two, Honeycomb is a startup. I work hard to make the company successful, sometimes in the evening, occasionally on weekends. If the company is wildly successful, the founders will make a lot of money, much more than I will. That reality only feels sustainable to me when I trust that my founders will be the kind of wealthy people who will make the world better, not worse.
Don’t try to be perfect. I used to be deathly afraid of making any kind of mistake as a manager. Making a mistake as an engineer seemed bad but less catastrophic (you could probably ship a patch to fix it, and all you had to do was live in shame for a week or two), but as a manager, people’s livelihoods and feelings were on the line. It seemed important to take as few risks as possible.
But working at a growing startup should mean experimenting regularly and often trying things that don’t work (as a manager, as a team, as product creators). So much better to focus on building up trust and good feelings, so you can quickly fix things when they go wrong.
Just like you build resilient systems that can survive a bad release or two, you should build resilient relationships. The prior positive interactions you’ve had with someone help make it possible to survive and debug saying the wrong thing or taking the wrong management tack down the line.
Charity is the master of this. She accomplishes many, many things and it is not through always saying the right thing or never making a mistake — she uses her strengths to build up a lot of good will with people so she can dive into it from great heights when things go wrong.
Charity has always said, “Hire people for their strengths and not their lack of weaknesses.” I had heard similar assertions before, but I’d never really internalized what they meant until Honeycomb. We really believe that team of people with a diverse set of extraordinary abilities and a few known flaws will perform better than a team of people who’ve all cleared the same minimum bar in the same few skill areas. It sounds obvious in theory but in practice, almost nobody hires like that — all our interview processes are focused on weeding out weakness. We should still try to find out where candidates are strong and where they are weak, but we should ask ourselves, can we adequately support this person in using their strengths, and do their strengths match up to where we need to grow? and not, can we find any weaknesses in this person?
Spread the good gossip. When I say “good,” I don’t mean the juicy stuff. I mean that stuff that warms everyone’s heart like the last 10 minutes of a Hallmark movie. I know, and I’m sorry.
If someone else anywhere in the company (or outside of it!) says anything good about my work, Charity is the first person to repeat it to me, with great enthusiasm (and sometimes a little embellishment). This is the only thing on this list that is a “one easy trick” tip, and I encourage you to steal it immediately with great zeal and vigor if you don’t do it already.
It’s easy, it’s gratifying, it makes people feel good, it makes you look like you as a manager are doing your job brilliantly and it sneakily takes way less work than manufacturing your own positive feedback, it encourages more giving of positive feedback in the future, and it binds the two other people involved together in a happy secret that will make them ever so slightly more pleased to work together the next time they cross paths.
It can be tempting to skip this if you feel like the feedback is obvious or it’s been heard before. Err on the side of repeating it anyway. The majority of employees I’ve worked with spend most of their time secretly worried they are bad at everything and everyone hates them, and a little repetition of positive feedback either helps or at least doesn’t hurt.
Give to and accept help from your network. Charity has one of the most amazing professional networks I have ever seen. If you got every engineer who believed themselves to be a real life or internet friend of Charity’s under one roof, the room would probably have more engineering talent in it than the main Google campus in Mountain View. From Charity’s network, I’ve hired amazing engineers, I’ve met brilliant managers who have shared their advice and stories with me, and I’ve been invited to speak at conferences half way across the country and half way across the world.
I truly have no idea how she has the patience or ability to turn random people she’s had arguments with on Twitter into friends and allies and don’t expect to ever figure that out, but I have learned a lot from her about how to work with people in your network. Cherish them, introduce them to the people in your network they’d benefit from meeting, put in more than you expect to get back, and don’t be afraid to ask them for help. Most people actually love to be asked for help when 1. they generally like you, 2. they feel like you’re recognizing their specific expertise in a flattering way, and 3. you make it low-hassle for them to do and are considerate about their time. It’s life-changing.
Be hungry for new information and willing to do something with it. One of the hardest things about being in a leadership role is that, the higher you go, the less information gets back to you about the actual work being done and the actual human interactions on the team.
To compensate for this, you have to aggressively seek new information and feedback. You have to hang on to the information you hear and file it away somewhere even when it doesn’t match the reality you see in front of you. You aren’t always in a place to fix the thing you hear about, whether it’s a suboptimal tool choice that you’re locked into for another three months for cost reasons, or a bad management habit that is getting in the way of your team working as autonomously as they could be. Not every broken thing can be fixed at once, sometimes you focus on the most important ones first.
But if you listen with a curious and open mind and commit to trying your best to actually do something with the information, you open the door to receiving more information like it in the future. And this is one of the only possible ways to avoid progressively spiraling down into being an out-of-touch dictator who does more harm than good.
Charity and I used to work together on product planning and the product roadmap regularly, and I always felt both awe and a little concern at how often she’d dig for my thoughts and opinions about product work, even when we didn’t see eye to eye, and even when my opinion was that we’d been Doing It All Wrong.™ We eventually ended up with something that worked, that got us over the chasm between having the entire company shout at each other in a room for a week and having a well-organized process that produced reasonable results and required minimal drain on everyone’s schedules. It wouldn’t have happened without Charity being willing to dig for more information and be fearless about trying new things out.
Believe in people, support them, and then give them space. Leave gaps for other people to jump into.
Charity once described the role of founders in the company as like lightning bolts — lots of power when they’re focused on a particular thing, but often gone in an instant. I used to feel frustrated that Charity would disappear sometimes in the middle of something that felt important, but I’d notice later: the outcome was almost always fine. The reality was that my other coworkers and I had the situation under control, and often having to jump in to fill a gap I’d imagined Charity would own was actually something that helped me grow.
I know so. much. more today about how to run an entire high-functioning engineering organization than I did when I first showed up at Honeycomb, and it’s almost never because Charity held my hand each step of the way. It’s because she saw the areas where I could do more and she got out of the way. I’m decent at juggling a lot of things at work, and I know it’s a useful skill, but I also know without careful management, it becomes a bad thing for my team — if I don’t hand off responsibilities as my team grows, I don’t leave a ladder behind me for others to climb up.
It’s easy enough to list these out as bullet points, and incredibly hard to do them all in practice. I’ve now had other managers report to me, and I still feel like I’m working every day to try to do these things for them with some consistency. On bad days, I remind myself that, while all of these were useful, there was one piece that mattered most: trust. Charity is an inconsistent presence in my day-to-day reality — she often has to travel for speaking arrangements, she has the weirdest sleep schedule I’ve ever heard of, and sometimes as a founder she just has top priority things that jump in front of all other responsibilities (hi, fundraising) — so many of the things on this list happen sometimes, here and there in waves. The one constant that has made all the difference has been feeling trusted. Trust has let me act with autonomy, it has let me be fearless in sharing my suggestions and concerns, even when they’ve been wrong, and it has helped us both forge ahead during hard times knowing we could mend most of the collateral damage at the end. I can’t always support my reports in all the ways I’d like to, but I can at least try to let them know the ways in which they are trusted and get out of the way.