The following is a list of things that I personally learned. Work in progress.
One on ones. It’s very important to have regular 1-1 meetings with people you interface with, and to treat these meetings with a lot of respect. This is obviously true between a person and their manager, but it’s also true for any important relationship. I think spouses should have 1-1s with one another, and parents should have 1-1s with their kids. The point is to get in sync with one another, to be aligned on your shared interests and goals, to be sure that you’re seeing things the same way, to address disagreements outside of the context of an actual disagreement (which can get heated), and so on. Read: Ben Horowitz’s A Good Place To Work and One on One.
Figure out behaviors in advance. On my first day in office, my boss told me that he had a meeting. Turns out that the meeting was a one-on-one with his co-founder. At the time I thought that was a little odd, considering that they pretty much sat next to each other and were talking to one another all the time. But over the years I’ve realized that that’s exactly what you should do. If you start out without such rituals and practices, it’ll be a lot harder to implement them later on when you need them. Similarly, we started having all-hands meetings a little bit earlier than it seemed necessary (when the company was at about maybe 8-12 people), but that made having all-hands much more natural when we grew in size.
Carve out personal time for intense work. Early on I was really excited to have access to the company’s internal chat, to see what people were talking about at any given point in time. I was very eager to contribute in any way possible, and so I’d pay attention to any alert to see if there was something I could do to help someone else. On hindsight, it’s clear that the biggest contribution I could make to the team would be to do a better job at… my job. Deliver on what you promised first, and be someone that people can count on to get things done. Multi-tasking is pretty much a myth. Do one thing at a time and do it well. Fulfill your fundamental obligations first as well as you can, then you can have fun with the peripheral stuff. Batch your emails and IMs in between sessions of work.
Show your work, early. When I first joined, I was intimidated by how smart my colleagues were. So I was very perfectionist and wanted to work on things in isolation for as long as possible. This was my ego keeping me from doing what was best for myself and for my team. Sharing prototypes allows you to get valuable feedback early, and correct things earlier in the stage of production– which is cheaper. (Andrew Grove has a chapter on this in High Output Management.)
Train and motivate yourself. To do something, you need to be both willing and able to do it. So if you’re failing to do something, it’s either because you can’t do it (unable), or you don’t want to do it (unmotivated). If you lack ability, you’re either going to have to train up (set aside time to learn the skills necessary, do a course, get a coach or mentor, etc) or delegate it to somebody else
Be as clear and precise as possible in your communications and thinking. A tragically hilarious amount of time can be wasted because you didn’t clearly answer the question “what does DONE mean?” If you’re not precise about what you want, then you’re either not going to get it, or you’re going to waste a lot of energy delivering a lot more than what is actually required. Be especially precise about the steps and sub-steps involved in a given task, the amount of time you’re going to take to achieve those tasks, and your expected results for those tasks. Making those predictions allows you to better understand your own output and plan your time better.
Write down your processes – what exactly do you do every day, and why? I wish I learned this earlier, and I still don’t think I do this well enough. There’s always a more pressing task to be done. But this is the meta-task that helps you do everything else better. This is something worth reflecting on and updating on the weekends, or in an end-of-the-week review, stuff like that. A good way of thinking about it is– how would you explain to your successor what you do, what needs to be done, and so on? Why do you do things the way you do? This achieves several things – one, if you’re going to suddenly have to disappear, you’ll be able to literally pass this document on to your successor.
Stave off burnout; carve out time for yourself. Again, being a rookie I felt like I had to put in long hours. Nobody asked me to do this, but I was generally inefficient anyway – I would spend excessive time over-researching things.
Take care of your health. Some people have this stuff figured out great, but I wasn’t one of them. I was smoking, eating unhealthily (skipping breakfast was probably my biggest sin), sleeping late, not exercising at all. Your health is typically the #1 influencer of your mental state, and your mental state is typically the #1 influencer of the quality of your work. Ergo, if you want to do good work, take care of your health. (It coincidentally makes you feel less shitty about life in general, which is quite a benefit.)
Figure out email labels and keyboard shortcuts. You’ll save so much time, it’s totally worth it. Actually, figure out the keyboard shortcuts for everything that you do– your browser, your OS, everything. I use a tool called Spectacle that allows me to move stuff around really fast.
Get a second monitor. The more you can see on your screen, the better. You don’t necessarily need to fill it all up with stuff, but it’s nice to have a “workspace”, and an “off-workspace” where you can keep your IMs, or calendar, or email. In my fantasy setup, I’d have a separate monitor for each of those things. I mean hey, we’re visual creatures and we’re wired to be able to take in tonnes of visual info. We’re supposed to be good at hunting on the savanna. Why are we staring at relatively tiny screens? I anticipate that AR/VR is going to change this in a huge way.
Get a good mouse and mousepad. It never really occurred me to get a good mouse, and I went years without a mousepad because I thought hey, no big deal. And fine, it’s not a HUGE deal, but if you’re going to be scrolling and clicking day after week after month after year, it makes sense to have something that feels good. Maybe it’s partially psychological. Who cares? It’s a tiny investment and it feels great.
Reach out to other people doing similar things as you, and build relationships with them. In my case that means – people who do content marketing, people who manage freelance writers, people who do marketing for B2B SaaS firms, and so on. Find people who’ve done what you’ve done before, and buy them coffee and ask them about their experiences. I wish I did this sooner.
Talk to people in other teams in your organization. I was lucky with this one – I joined the company when we had about 6 people, so I got to know each new person as they joined, and I got a pretty decent understanding of how different functional roles come together as a cohesive whole. A company with teams that understand each other’s roles and challenges well can have a big advantage over a competitor that doesn’t. Lunch is a great time to do this. Ask other people what they’re working on, what they’re struggling with. Sometimes some of the best insights happen this way.
Update: Also check out The Instructions I Wish I Was Given As A Newbie Startup Markter