Deadlines That Are Doomed From The Beginning

Photo credit: William Iven https://unsplash.com/@firmbee

As we get close to the end of the year, we get pulled in a number of directions, both personally and professionally. This can, of course, induce a case of I just don’t wanna.

And we’ve probably committed ourselves to deadlines, only to discover that we probably won’t meet them.

Instead of just coming right out and saying the obvious, “This deadline is unrealistic, and then providing reasons,” we put in longer and longer hours. In some cases. we meet the deadline, and we’re heralded for having superhero-like qualities. But if the deadline slips, well let’s just say someone is subtly blamed…

This is a ridiculous cycle, and I know some people would revolt and say we just need to abolish deadlines. I don’t think that’s the answer because deadlines are important markers that hold us and our teammates accountable.

Instead of jumping to abolishing deadlines, let’s start by understanding why they slip.

Why Deadlines Slip

First, if we’re working for someone else, then we get accustomed to operating on someone else’s timeline and de-prioritize our own time.

Second, whether it’s our own project or someone else’s, we don’t take the time to dive in and understand if we have set reasonable expectations for when things can be delivered. We may be excited to start the project and get it out the door, or just blindly commit because we don’t know any better.

So how can we set a more realistic deadline? We’ll let’s dig into an example. Robert, one of the students in my Ship It Course, recently told me that he wanted to release a mobile app in the next month.

Instead of telling him that it was unrealistic (I figured he might get defensive), I started by asking him some questions, and the conversation went something like this:

Me: “What is your goal in building this mobile app?”

Robert: “Our existing customers don’t want to be stuck using our product on the web, and they have mentioned they would be willing to pay for the convenience of having an app. They want something that fits into their on-the-go lifestyle.”

Me: “Got it.”

Robert: “Yeah we want to give them a positive experience.”

Me: “Have you begun development of the app?”

Robert: “No.”

Me: “When do you plan to begin development?”

Robert: “Once I find an iOS developer.”

Me: “Have you been evaluating developers?”

Robert: “No I’m going to start soon.”

Me: “How long do you think it will take to find a solid developer.”

Robert: “1 week.”

Me: “And have you designed the app?”

Robert: “No.”

Me: “How long will it take for you to design the app?”

Robert: “1 week.”

Me: “And how long does it take to release the app?”

Robert: “2 weeks to get approved.”

Me: “OK. So given that it’s going to take you 1 week to find the developer, 1 week to design it, and 2 weeks to get approved, that gives you a total of 4 weeks.”

Robert: “Yeah so I’ll meet my deadline!”

Me: “Hold on sec… You did say that your goal was to give customers a positive experience right?””

Robert: “Yes, it’s very important.”

Me: “Then there are few things you need to think about. First of all, you haven’t accounted for how long it’s going to take the developer to build the app. Second, given that you want customers to have a positive first-time experience, you want to make sure to test. During the testing there maybe some issues customers discover that the developer will then need to refine.”

Robert: “Oh right, I didn’t realize I’d need to do all those things… I now see that 1 month is unrealistic. But I’m really concerned that our customers will leave!”

Me: “Are they canceling?”

Robert: “No but they’re complaining and want something that is more convenient!”

Me: “And how long have the majority of your customer been using your web product?”

Robert: “1-year.”

Me: “Well if they’ve been using it a year already, then that means they do value it. And yes people will always want something that makes their lives easier. If your goal is to give them a better experience through a native app, then you need to think through the development of it, and make sure that what you launch is of high quality.”

Robert: “Yes, I realize I’m rushing things, and that might have a negative impact on the quality of the product.”

Give People The Benefit Of The Doubt

Given that this was the first time Robert was building an iOS app, I gave him the benefit of the doubt. I didn’t start of by telling him, “Robert you’re being unrealistic!” I started off by understanding what outcome he wanted and why: to provide existing customers a native app. Then walked him through all the pieces he’d need to put in place to make that happen. In the course of doing that he realized that releasing an app in 1 month would be unrealistic. It’s important that people who are the decision-makers on a project come to this conclusion themselves, rather than us just telling them! Robert concluded that 3 months was a more reasonable time frame.

I also helped him understand that if he wanted to avoid additional delays and meet his 3-month deadline, he’d need to make sure that he wasn’t overcommitting and to hire a developer that would be OK with highlighting if something was unreasonable.

When Setting Deadlines Work Backward

The key is to work backward! To summarize, here are the steps you want to think about:

1. Start with the proposed deadline.
2. List out the major things that need to happen.
3. Ask yourself how long each of the steps in #2 will take (assuming the best case)? Also factor in time to learn, research, test, and iterate depending on what you discovering during testing.
4. Get someone else to review your steps, and ask them the question, “What have I overlooked?”
5. Factor in any additional steps from #4.
6. Finally, if things do come up, as they will, ask the question, “Does this impact the outcome we want?” If it does then you’ll need to stretch the deadline, if it doesn’t then put it on the back burner!

I know it probably feels like I’ve only tackled the planning phase, but you can reuse these exact steps for dealing with an existing unrealistic deadline. In that particular situation, you want to understand what is more important the deadline or delivering everything you committed to. Finally realize that no matter how much you plan, or think you’re going to ship a project on time, things will come up and some tasks will just take longer than anticipated to complete.

Now I want to know when was the last time you set and met a deadline? How did you do it, and did you feel good while you were heading towards it, or did it leave you feeling drained?

Let me know in the comments!

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