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How Deadlines influence your Success

👋 Hi Everyone,

for more than four years I‘m participating in many diverse digital product projects at my agency. As we all do, I reflect on more general things from time to time. In recent months I started questioning project management methods.

Last week a thought hit me about how deadlines can improve or destroy the rhythm of a project. First of all, deadlines might be something you really hate or even enjoy. One thing is sure they exist and won‘t leave us alone anytime soon. They can be crucial or holy help. It all depends on the context of the project. That‘s why it‘s so important to align project management, expectations, and delivery dates.

Overall I could identify four different types of deadlines.

Types of Deadlines

They all have their strengths and weaknesses. Let‘s recap.

Deadline Roulette

This comes from a more traditional perspective. A team somehow commits on a date. It‘s more guesswork instead of a realistic timeframe. Probably the deadline will be missed. That‘s why a new one is arranged. Maybe a bit more realistic, maybe not.

Interestingly the cadence is pretty low. A deadline won‘t happen often. But when it occurs stress is inevitable. This kind of guesswork happens in more complex or chaotic structures. In my experience, it doesn’t do anybody a favor and builds up pressure. When guessing a date is part of the process most likely important data for decision making is missing.

Agile Deadline

Scrum, Kanban, and friends established the deadline as something absolutely normal. Every x weeks it‘ll come. And that‘s okay. A lot will be accomplished. Some things might be left on the table. The end of a sprint marks something new instead of expressing confessions. I experience that this rhythm feels somehow natural. An established anchor exists that guides you through the process of creating.

By the way, this is the same how I feel when I have weekly calls with clients. They listen, I report, we plan. Week after week.

Deadly Deadline

This is an interesting approach that is used in the Shape Up methodology established by Basecamp. They see a feature or project as a bet that they place. For each bet, an appetite is defined. That means it‘ll be determined how long a team works on something. Most of the time it‘s six weeks for them. Of course, you have to make sure that your goals are likely to be achievable in that time frame.

Now comes the twist. If you don‘t reach your goals you just leave the work on the table. No more fixing, no more trying to somehow get it done. If it‘s not executed in the given time that‘s fine. Something new is waiting for you.

I‘m using this method from time to time on my side projects. This forces me to prioritize and setting the right focus.

No Deadline

Maybe it‘s a bit of cheating. But the best deadline can be no deadline. If the execution motivates you and you want to make sure it has a high quality why hesitate? Work as long as you like the outcome and it‘s ready to see the world. The hard thing is to decide when the time has come.

This is how I approach long-running topics. Especially when I know that I have to achieve something but the timing doesn‘t really matter.

Conclusion

Choosing the right cadence is undervalued. Every project has to find its own rhythm to accomplish the goals. What I unfortunately see is that there‘s a certain default without questioning things. In software development, it‘s scrum where deadly deadlines could maybe fit better into the process. Especially when a product is young.

Now I‘m curious whether you enjoy the pressure of a deadline or it‘s something that stresses you out. Tell us your point of view in the comments.

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