But are we really late?

For the past couple of weeks I've been interviewing for a new role. It's a fun exercise that has me take a look at my career, comb through the things I've done and people I've interacted with. As I'm looking through the projects I've been involved with, I see a pattern with deadlines.

There weren't many things that have a strict internal deadline. There are external deadlines, like regulatory due dates (remember GDPR?), major changes in the vendors that are too big to adjust for us, and software deprecation issues.

In the cases when the deadline is internal , it's there to coordinate: "We discussed with marketing that they need this for the campaign three months from now" or "We're showcasing our milestone at our conference".  There's a special case for deadlines to be "as fast as possible" because of a market opportunity, but that's not a specific deadline.

This doesn't discredit deadlines — on the contrary, it lets us examine them for what they are. Since there's no implicit due date, an internal deadline is a tool that is applied to simplify coordination. It's a level of indirection that creates a bias for action and helps us ship things.

Where does that put the word "late"? What does it mean for an effort to be late?

Similarly to underperformance, "being late" means that the expectations don't match the reality anymore. The expectation was set in a context in the past, where it took the form of a date and some success metrics. Over time, the context has changed, and the date wasn't updated to the expectations.

When we're late and the deadline is internal, we have two options.

We can evaluate the cost of changing the date versus the cost of changing the success metrics , a cost of delay. For example, we can look at whether pushing the release by a month will mean that marketing has to prepare the campaign again.

Another option is reexamining the success metrics. If there are things that depend on the release and, considering that we have a lot more context about the scope of the work, we can take a more careful look at the metrics and check if all of the efforts contribute to the metrics. For example, if we're showcasing the new product at our conference, we don't necessarily have to release it to the general public at that moment. We can start testing with a group of users and get their feedback. The product can still be showcased.

If there's no coordination attached to the deadline, and it's not external, then it's probably made up. That doesn't dismiss the deadline, but it calls for a good conversation about expectations — why was this date picked? What is the cost of delay? And what was the need that drove someone to pick a date? All these are great questions for a retrospective.