What to prioritize? This is a very hard question to answer. I’ll try to talk about this in the context of uOttaHack, though much of this applies to all aspects of my life.

The first thing that comes to mind is that a lot of the time - it’s extremely hard to even get the chance to prioritize. I think this comes down to the nature of running an event like a hackathon. Much of what goes on you figure out on a day to day basis, and you sort of just have to tackle what comes to you. Now if we are talking about how to prioritize those tasks, that’s very simple: you do them in the order they are due. This is because you can only really prioritize things if they are not directly impeding. If you are told at 9 something needs to get filled out by 2 - well there’s not much debate what you’re going to be doing.

If I were to roughly quantify it, I’d say this is how I look at things 70% of the time. Of course, not to the same level. The turnaround is not always 3 hours, but it is often the case something needs to get done before others so that takes care of the whole prioritization issue.

Now, the other 30% of the time. This is when there are things are of roughly equal timeline and you have to make a call on what to work on. This is where stuff gets interesting, so let’s explore some different approaches.

One approach is looking at tasks that will have a definite impact. I resisted saying move the needle here. Definite impact means something tangible. If you raise money, that’s tangible. If you ship something, that’s also tangible. Things that are less tangible are having meetings, drafting a memo. This is not to say things aren’t important. It’s just to say it’s harder to measure their value relative to the other items I talked about. Where this falls apart is when everything on your plate is tangible, Which is often the case, since hackathons are high-agency (we move quick at uOttaHack!).

So onto some other approaches. Another possible way is to prioritize things that build excitement. Excitement amongst team members, and the general public. This is a much better approach. This approach requires some of the first one, since people don’t (generally) get excited by sitting in a 3 hour long meeting. And so you probably have to have something that has a definite impact to get people excited. The reason this is a better approach is because people get excited by seeing things. When people are excited, this energy is contagious and makes people more inspired to do amazing stuff. Of note, is that this isn’t the most sustainable way to do things. You won’t always have something that makes people excited, even if you try really hard.

You can beat this issue by this next approach, which is to prioritize what gets done quickly. This is of course an issue in itself, since it’s hard to get things done quickly. An effective approach, though, since whatever get’s done quickly is usually what needed to get done anyway. If you need to get the dishes done, you are probably not gonna stand there for many hours on end doing it - you’d get them done quickly. Another benefit to make note of is that, usually, speed of execution fixes all problems. There is almost nothing to gain by doing things slowly. Even if you move quickly and produce something suboptimal - at least you have something. Moving slowly would have you nothing in twice the amount of time. It’s also better for feedback. It’s hard to give feedback on something you can’t see. So even if what ends up getting produced as a result of moving quickly is not good, it can get good - quicker, because you moved fast in the first place.

The only place this approach fails is when it comes to tasks that move slowly - because of something out of your control. It’s important to use this mindset sparingly, because things are not always was they appear [1]. This aside, it is a possibility that something that moves slowly, and is important - is completely out of your control. In this case my reaction would be to not worry about it and move on to the next thing that can get done quickly. Time fixes most of these issues, and the difference between waiting 1 day while worrying about it versus 1 day while working on something else is huge. Onto the last approach though, which fixes all these issues.

The last approach one that is hard to beat. And you may not be satisfied with this answer because it’s very anti-climatic. The best way to prioritize is to focus on what helps your vision. This seems like a terrible answer - because it sounds like a cop-out. On paper, it is isn’t really an approach - because it relies entirely on there being a good vision. If the vision is good, then the tasks that move it will be clear and useful. If the vision is bad, the opposite will happen.

Here’s a quote to help exemplify what I’m talking about. It’s from Doug Leone, the former Managing Partner at Sequoia Capital.

It starts with product management. What exactly are we building? If truth be known, it starts with vision. But if the vision is wrong, we’re all going home, assuming we’re some place in a ballpark.

If the vision for what you are trying to accomplish is clear - it’s easy to avoid the problems that we talked about before. If everything on your plate is tangible, the thing that allows you to delineate what to work on is what best implements your vision. If something doesn’t build excitement, the next best thing to work on is what moves your vision. And if something is moving slowly - then your vision will either tell you it’s useless to work on it (regardless of how fast it’s moving) or it’ll tell you it’s the most important thing, drop everything and make it happen.

It’s often the case that this “vision” is not grounded in pure metrics as it may come to mind. Often the times the vision is not the fanciest thing in the world. A good vision is to want people to feel like they can ask questions. To feel like they belong and can make mistakes. A good vision is to have an organization where people feel safe and okay with experimenting, and taking risks. Equally a good vision is to create an environment of fun, of engagement where people want to do there best work.

All this isn’t to say that the metrics aren’t important - or that the metrics aren’t what ultimately are the things to work towards. Of course, if you are running a company - you need to make money to keep going. But this really isn’t a worry if you are making something people want. And that’s not really a worry if you create an environment where it’s easy to make something people want.

So hopefully it’s obvious by now, that whatever end goal you are working towards - it start’s with the environment and culture that you create. The outputs will handle themselves if you are able to create a space where people can strive to do their best work. That’s the real vision, and when you focus on prioritizing what help this, things work themselves out. And if you don’t, well - you might be going home.

Notes