Deadlines – good, bad and ugly

On a recent project, I got to experience the power of deadlines and their consequences – both good and bad. I don’t know if I have a general thesis here. This is mostly just me thinking out loud to help process the events of the last few weeks. So I am structuring these as just collection of random thoughts with some learnings along the way.

1. Increased focus

On this project, we had set a deadline based on initial scope which was not accurate. As a result, we ended up in a situation where we had to accomplish a lot of ambiguous tasks in a very short period of time. By ambiguous, I mean tasks that required a fair amount of research or trial and error. I think having a deadline helped us be ruthless about finding solutions that worked. I can totally see an alternate world where if we had more time, we would have spent more time finding solutions (see Parkinson’s law).

In other words, tasks take less time to do if you are sufficiently motivated to do them and this motivation can be intrinsic (this is fun!) or extrinsic (deadline). Of course, we never factor this in when planning out projects since it’s hard to account for. But there is some implicit acknowledgement of this when there is an effort to match people to the right projects. At the end of it all, I realized how much a deadline really helps with focus and mental clarity in getting something done quickly.

2. Added stress

The updated project deadlines created a lot of stress for me. But deadlines are not new for me, I’ve had them on every project I’ve worked on. So why did this stress me out? I suspect this happened because there was a lot of ambiguity in the tasks and hence I didn’t have as much confidence in meeting the deadline. The way to normally handle uncertain situations like this is to allocate more buffer and push the deadline to a more reasonable date. But due to some special circumstances, that wasn’t really an option here. I worked a lot of hours – more than I ever have in a single week – to be able to meet the deadline. Overall, I think the stress came from a lack of control/predictability over achieving outcomes in the given timeframe (On a related note, I have written about mental energy here).

3. Effect on decision making

My decision making ability suffered immensely in this very stressful period that lasted 1-2 weeks. It seems really easy to identify this in hindsight but I am not quite sure how to be more aware when this happens again. Maybe writing about it will help reinforce this idea. For example, I had to implement 3 different solutions since each of them had some downside that wasn’t obvious to me before building it. Thankfully, it didn’t take too long and I had some help from peers to give suggestions to guide me on the right path.

I could have mitigated some of this if I had taken some time to formulate a plan before starting. But the solution that I had started on was agreed upon as the most promising at that time. So maybe there is some hindsight bias here. Overall, I don’t think I was in the right mental space to step back and make the best decision. Something to work on for the future when I am in a similar situation.

4. Bad incentives

Due to the deadline stress, I reached a point where I no longer cared about getting all the details right. I just wanted to be done with it. As a result, I made some mistakes like not sanity checking things which resulted in a poor user experience. There were other issues that I noticed but I let it slide since we were short on time and I didn’t want to delay things further. In other words, my incentives were not aligned with what was the right thing for users.

Unfortunately, this happens a lot and this frank admission will surprise people in leadership positions. It’s easy to pass judgement in situations like this – I’ve done this myself. It’s a lot harder to dig into systemic issues and address root causes since that takes time and effort. If everyone cared about every single thing that they did, it seems like a good outcome but it does have costs. The right incentives promote the desired behavior and ensure the right trade-offs are made. My big takeaway is that I should take more ownership since the consequences of not doing that are too high.


This whole experience taught me that there is so much I can learn about myself through these situations. Who I am and how I act changes a lot depending on the context. Being aware of these differences is a good first-step. Feel free to share your own stories of dealing with deadlines in the comments section. Thanks for reading!

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