How I Decide What to Work on Next

A prioritized list of web projects are typically sorted in order of importance, from most to least. So to decide what to work on next, it should be simple enough to follow prioritization ordering, right? In theory, this is exactly what one should do. But in practice, it unfortunately isn’t that simple. What if the next most important project is about 4 weeks of work and can’t be launched for 6 months? Or what if it requires a huge lift on a resource that is currently heads down on work that is more critical than the next one?

If you can’t decide what to work on next by simply taking the first item at the top of a priority list, then how do you decide? The way I do it is by taking a number of key factors into consideration and ultimately, making the decision by relying on my intuition and experience to guide me.

The Key Factors

Much of the time, you’ll be able to look at a prioritized list and as a general rule, work off of that. But as with most decisions, the variables are multi-factor and it’s important to weigh them all. In addition to priority, here are some other factors that I consider when deciding what to work on next:

Timing

Not the most exciting dimension by any means, but I always look at the when for the what. A less impactful project might get worked on first, if time allows for the more important project to be picked up on later. For example, in direct-to-consumer ecommerce, Black Friday / Cyber Monday (BFCM) is one of the most important shopping periods of the year, but we’re not going to work on creative for it in February. We’ll work on something else instead at that time, even if it’s of lower overall importance.

Resource Availability

Any time that I’m dealing with a prioritized project backlog of a decent size (let’s be honest, that’s every time), I will inevitably run into a situation where consecutive projects are dependent on a resource of which I have a limited number. Additionally, there are times when resources are out, whether for PTO or other reasons. If the next most important project has a dependency on resources that simply aren’t available, I just have to work around that and find something else for us to work on next.

Internal Needs

This refers to situations in which others within the company need or want something, often unexpectedly. Sometimes, this can be a one-off request from a HiPPO (Highest Paid Person’s Opinion), but it could also involve situations where teams simply need your help. In a previous role, our customer support team was manually loading SKUs to provide individual product support, and due to cuts, just couldn’t keep up with the volume. Since our web team was already doing that work for the marketing site, we were able to help them by providing access to a product feed that they could ingest for the support site. This project wasn’t anywhere near the top of our priority list, but I felt that given the cuts, and the importance of customer service, it was in the company’s best interests that I get it into our work pipeline. It was a completely arbitrary decision, but in my view, a necessary one.

Morale

Over a significant enough amount of time, situations will inevitably arise where the team needs a pick-me-up. Whether it’s the come down after the completion of a major initiative, or a sustained period of working on projects of a similar type, it is sometimes necessary to force a context shift in order to keep the team engaged and producing at their best. At 37signals, the company behind the project management product Basecamp, they utilize a 2-week cooldown period where team members can work on whatever they want. In a similar fashion, when I’m trying to figure out what to work on next, I always have a pulse on the team, and if it feels like we’re going through the motions a bit, I know it’s time to look at projects that are more fun to work on and require us to think a little differently. If the opportunity and need is there, I will find a way to get them in front of us so that the team has fresher minds and stronger energy for the prioritized items down the line.

Conclusion

I wish there were a simple, single path framework for making decisions on what to work on next. But whether we like it or not, reality is unpredictable and having the flexibility to make arbitrary decisions in that regard pays off in the long run. Plus, having a hand in what you’re doing just makes the work more enjoyable and rewarding to do. I’ve also found that looking at everything in front of you, actually having to think about them, and going through the mental exercise of figuring out what should go where and when, makes the work feel more tangible and less conceptual. It’s like the difference between holding a $100 bill in your hand, and seeing a $100 credit on your bank statement. In the end, working solely off a priority list can probably get you around 75% of the way there. But to go all the way, it is critical to weigh all factors, including maintaining strong situational awareness of your team, company, and partners.