The single best improvement to my workday has been a daily sitdown that me and my marketing team (writers + designers) do every evening, a short while before we head home. We started out simply just discussing what we did that day. We talked about what we had done, what we got stuck with, what we needed help with, and what we planned to do the next day.
Initially, we found each other’s feedback invaluable for getting unstuck– we were often missing simple things that other people could catch. We also found that talking about getting stuck at a daily level allowed us to move faster– previously we would only get unstuck at weekly meetings or so, and things were moving too slowly to be meaningful.
After a while, we found that we got stuck less and less. I think this was because our daily commitment to chatting about what we’re stuck with actually jogs our subconscious into picking things that we’re less likely to get stuck with. We anticipate the “what are you stuck with?” question and we start applying it ourselves, before anybody else. We frame our problems and challenges more precisely, so that failure is less likely.
After a while, we realized that we could keep track of the stuff we were talking about, and use it to plan future tasks, to assign other tasks. (We tied this up with Asana, which we tried earlier to use as a collaborative task-management system, but we would often fall short on it because things would happen and not get checked off, and it wouldn’t be the most accurate representation of reality… so we would all have multiple versions of reality, and end up having to ask each other over IM or email).
But since having daily sync-ups, we’d just double-check on all our tasks, update and/or delete old ones, reassign things, update things, so on and so forth.
I then thought that merely talking about status updates was getting a little bit boring and stale (in a good way– like a boring news day because there’s no drama), and that we could get more out of each other if we used the opportunity to also tackle interesting questions and challenges outside of the scope of our daily work. I decided that we’d have a “question of the day” to think about and to answer– things that would make our work more interesting, things that would help us get to know each other better, things that would make things better on any dimension. Questions we started out with were- what are you curious about? What do you want to get better at? What can we do to make our environment more fun? Things like that. And then we create and assign tasks, and then we get things done.
These daily sync-ups have become the highlight of my day. I feel more connected with my team members. I feel like I understand them and their interests better. I feel like I know better what they want to do, what they want to learn, and I have more context for how I can serve them, both through my work and through things outside of work. Talking to other people about the work I’m doing– and committing in advance to the process– helps me make sense of why my work is important. Prior, I would just pick tasks at random– and more often than not pick things that were simple or easy rather than things that were important. It’s not like I’m the most systematic man around right now– I’m still really random and inefficient, but just being accountable to other people has made me make much better decisions.
I’m thinking now about smoking as well– how I’m pretty sure my work environment played a huge factor in helping me quit smoking, because I cared about what my colleagues thought of me. And while I’m sure none of them thought horribly of me just because I was a smoker, I enjoy having quit smoking in their company. I want to do other things that make them happy and proud, because they’re great people.
I think I first got this idea after doing 1-1s with my boss. (When I asked him where he got the idea– because I’m not particularly well versed in this sort of management thinking– he pointed me to Ben Horowitz. This is an especially powerful read.) I met another one of my colleagues for a 1-1 a couple of days ago over lunch before we headed to work, and he told me that he was starting to apply such thinking to the rest of his life as well. I relate. I’ve started thinking about applying 1-1 thinking to my other relationships with people that I care about.
It’s not so much about “being businessy” or “corporate” or any of that stodgy stuff. It’s about prioritization. About focusing on what is important, and about encouraging communication. You can meet somebody every day and talk to them about all kinds of junk and yet feel like you didn’t learn anything about each other, like you didn’t actually connect. You were going in circles, but you never got to the things that actually matter. You avoid the elephants in the room, you have safe and boring conversation. There is value in that for sure, but I think there’s a lot more value in addressing the difficult things.
Of course, if this applies in conversational space then it doubly applies in every other kind of space, too. Which is something very worth thinking about. Just as I wouldn’t want to play poker with fake money, I wouldn’t really want to have small-talk conversations without any real stakes. Not because I dislike small-talk, but because I should prioritize things that have real influence, real significance.
It’s possible to have fun and be of significance at the same time, so. Some people will misunderstand this, and some people will get it. And to demonstrate that fun+significant+focus principle in action, in a meta way– it makes zero sense for me to engage with the people who deliberately misunderstand it. Only with the people who ask genuine questions, borne out of curiosity.
Anyway… so I want to get more out of all of this. I want to do regular sync-ups with myself. Writing helps me do that. But I can afford to be more deliberate still.
 This also makes me think about how my “work” writing has bled into the way I think about doing my “casual” writing. It’s not particularly a deliberate choice. I started out trying to separate my work and personal writing, thinking that they were two separate things that shouldn’t mix. My work writing was supposed to be more scientific, and by extension I thought it would be more cold, less fun, so on. But it turns out that being scientific in your thinking is a hell of a drug– because it’s about identifying what matters. You end up focusing on whatever is most important. And this is a skill that translates well to any sort of pursuit. You start looking for the most important and counter-intuitive things everywhere you go. And if you learned this while trying to write serious things, you’ll find that it also makes your jokes funnier– because you seek out whatever is most funny about something. And so it goes.