Deadlines are a good thing.

Leeor Engel
5 min readJan 5, 2020
Photo by NeONBRAND on Unsplash

In a previous post, I talked about what makes a good goal. Once you’ve done the hard work of setting the right goal, it’s time to start thinking about execution.

A goal without a completion date is a wish [1].

Now if you want to actually accomplish that goal, you are going to need a deadline.

In the context of a goal, a deadline creates a forcing function. A behaviour-shaping constraint. Constraints are great; they breed creativity and resourcefulness. They force necessary trade-offs to be made. Trade-offs present themselves frequently during projects. With every passing day or week, we are presented with choices to make on how to proceed.

Is task A still more important than task B? Is task C still important right now? Task D now blocks task E: What are we doing about that? What is the largest unknown right now? What is the highest risk right now? Do we really need this meeting today or can we stay focused?

Without deadlines, we can easily miss the opportunities to notice, evaluate and act on these trade-offs. And there is always an implicit trade-off; the opportunity cost of other work you aren’t doing.

But deadlines get a bad rap. Most people have had at least one bad experience with a deadline in their careers. The word deadline has baggage.

This is unfortunate. Deadlines are actually a fundamental tool to have in your execution toolbox. I believe that if used properly, and in the right context, deadlines are a critical ingredient to successful project delivery.

What deadlines are really all about

Deadlines are about keeping you focused on what’s most important. That’s it.

Deadlines are about keeping you focused on what’s most important. That’s it.

Deadlines are not about getting people to work harder, or longer. Deadlines are not about getting everything done. Using deadlines for these purposes is misguided at best, and abusive at worst.

Deadlines should actually help you work smarter, not harder. It’s easy for hours in the day to evaporate due to meetings, distractions, or focus in the wrong areas. Deadlines help you maintain that awareness. Deadlines help you focus.

What does success look like?

So what does it actually mean to successfully meet a deadline? It means accomplishing your goal. That’s it.

So what does it actually mean to successfully meet a deadline? It means accomplishing your goal. That’s it.

It doesn’t mean getting all the tasks completed you originally planned to.

Making progress on a project almost always reveals new information and understanding of your problem. Integration of this learning can often lead you to save time; creating opportunities to delay or cut unnecessary scope or discover missing or unnecessary requirements. You make hard choices along the way, while always keeping your larger goal in mind. Remember: plans are for planning. No plan survives contact with reality.

An execution recipe

I’m a big believer in the 4DX model. I think it’s a fantastic framework for executing on your goals within a time-frame. It’s not too prescriptive about deadlines, but it lays out all the other important ingredients:

An important goal.

You need an important goal. A deadline is meaningless without a clear and important goal. If you don’t have an important goal you are working towards, you have no business setting a deadline. Goals come before boundaries, not the other way around.

Setting a deadline means pulling out the machinery of the execution process (see below). You do this for the truly important stuff. Hopefully there is a lot of that, but not all goals are created equal, and balance is important. I don’t think deadlines are necessary for everything. The nature of work tends to ebb and flow. There’s always in-between periods between projects. Use deadlines for the important stuff.

Keep a scoreboard

People play differently when you’re keeping score. Having a scoreboard that tracks your lead measures is critical for tactical awareness. It’s your best tool for recognizing the need for course-corrections in your plan. It also provides an important feedback loop for re-prioritization.

A cadence of accountability

Accountability is super important. I like a weekly cadence. A weekly team or staff meeting is a great place to do this. You can pull up your scoreboard and have a frank team discussion of where things are at. If things are going well, what has be done to maintain progress? If things are not going well, how do we course-correct and get back on track?

Pitfalls & Anti-patterns

Distant deadlines

People have a tendency to procrastinate on deadlines that are far away. If you have a large project, break it down into smaller milestones, and have each milestone have a deadline. Treat each and every one of those milestones as a firm deadline. Don’t allow the milestone deadlines to be soft deadlines. Don’t let them slip. If one of them slips, every other subsequent milestone slips too. You need to have strong discipline to do this. This is one reason why many long projects fail. Leaders lack the resolve to hold firm on those intermediate dates, because they naively believe it can be made up later.

Missing deadlines

If you miss a deadline, quickly establish a new one. It’s all too easy to fall into the trap of a nebulous post-deadline limbo state where progress stalls. When setting a new target, make sure that it’s actually doable. You will likely have a lot more information at that point to make a more accurate projection of how much extra time you will need. Be honest with yourself about how much additional time is really needed. You don’t want to miss it again.


In my experience, teams that ship on time are happier teams. Projects that drag on and on are demoralizing, and make people feel like their work doesn’t matter. Remember: shipping is a feature.

Deadlines are a fundamental and necessary aspect of great execution. When used in conjunction with a good goal, they incentivize the right behaviours and help you stay focused on what’s most important to accomplish that goal, significantly raising your chances of success.

Thanks to Sean Steacy & Arup Chakrabarti for reviewing the first draft of this post.


Originally published at on January 5, 2020.