Missing Deadlines? 5 Reasons Why (and How to Fix Them)

Identify why you’re not delivering on deadline and figure out what to do about it

This post was first published on my Medium blog—follow me there for the most up-to-date entries!

As business owners, we have missed more deadlines than we want to admit. Missing deadlines as an employee is one thing; an owner missing deadlines can bring an entire operation to a halt! But how can we fix that? One of the first ways is to figure out what’s slowing us down. True, it’s “procrastination,” but is there something deeper to address? Read on to identify the real reason you’re not delivering on deadline.

You didn’t set a hard deadline

Business owners don’t have a boss to answer to. Without a need to be accountable to someone else, it’s easy to set multiple soft deadlines, and then invent a ton of reasons why it’s so important to delay.

First fix: Join a weekly accountability mastermind group. Research studies have shown that going public with goals helps us to deliver.

You don’t have a team

At least in the beginning, we’re tempted to do it all. However, having a team means you can delegate some tasks to a teammate. That will help you to do what you do best and to move along more swiftly.

And technically, although you don’t need to “answer” to your team, you do need to be a good role model, so there’s a higher likelihood that you’ll deliver on time.

First fix: See if you can delegate something to someone who is qualified to do the task.

You don’t know how you’re wired

As you know, I’m a big fan of self-awareness. If you understand how you’re wired, you’ll be more likely to identify the real reason you’re not delivering on deadline.

I’ve learned so much about myself by doing psychological inventories and assessments. Here are the ones I’ve completed (sometimes, more than once):

Myers Briggs Type Inventory
Kolbe A Index
Enneagram
Gallup Strengths
Executive Skills Questionnaire (Dawson and Guare)

I’ve been certified in the Myers Briggs Type Inventory, but I’ve found all of these tools helpful to one extent or another. They help to explain why I do what I do (or don’t do), including my behaviors to meet or not meet deadlines.

When I completed the Enneagram assessment, I realized that I’m a number Three. That means that I’m a “performer.” I push myself to revise and revise and revise. (Do you hear procrastination there?) While the other assessments and inventories are very helpful, the Enneagram stresses that it’s not just the behavior or the preference; it’s the motivation for doing what we do. Hence, as a “Performer” I’ll keep revising for fear of losing approval from other people.

On the Kolbe A Index, consider the Fact Finder scale. I’m a seven. That’s 7 out of 10, which means that I might get lost in collecting more facts before I move on. (Do you hear procrastination there?) To get moving, I remind myself that Jeff Bezos, CEO of Amazon, says that every day, he makes decisions with only 70% of the information he needs. Knowing my tendency to keep gathering facts, I remind myself that if I have 70% of the facts, it’s okay to move on.

When I understand the reason I’ve been slowing down, I’m more able to just pick up and move on!

First fix: Take at least one of these inventories or assessments and consider how you might accommodate your processes.

You’re making decisions too slowly

Be honest. Are you just plain slow at making decisions? Or is there something else about decision-making that’s holding you up? This might be a prime reason you’re not delivering on deadline.

I found a lot of freedom when I encountered Annie Duke’s book Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts. She gives a framework for making H.O.T. decisions. Duke says we must ask ourselves:

H. Will it make me happy?
O. Is there only one option?
T. Is there a two-way door?

Start with “happy.” Florence Scovel Shinn says that the “square of life” consists of only four aspects: Health, wealth, love, and self-expression. Ponder that for a moment.

Next, “Is there only one option?” I’d argue that we have more options than we might immediately recognize. There’s seldom just black or just white. There are almost always shades of gray, so try not to get hung up choosing between only A or B.

Finally, the “two-way door.” Tell me: How many one-way doors have you walked through in your life? Few, I’m guessing — most doors you enter, you can exit again. So don’t spend a lot of time and energy worrying about walking through the “wrong” door. I view getting married as the only decision I have ever made that was a one-way door. And for the record, it was the best decision I ever made!

First fix: Ask yourself these H.O.T. questions if you’re slow with decision-making: Will it make you happy? Is there only one option? Is there a two-way door?

You haven’t allowed yourself to create a Minimum Viable Product

Perfectionism is another name for procrastination, and a huge potential reason you’re not delivering on deadline. I understand — you want your product to be as good as it can possibly be before anyone else sees it, let alone pays for it. But if you’re missing deadlines, it’s time to think about your Minimum Viable Product.

What’s a Minimum Viable Product (MVP)?

Well, it’s pretty much what it sounds like. It’s a product. It can go live. It’s minimally acceptable. In their book Born to Build, Jim Clifton and Sangreeta Badal talk about how to create the MVP.

You could think of it as a beta version of what you hope to create later. Or, as author Michael Hyatt calls it, “wet cement.” It will be solid someday, but not now.

Here’s my definition: It’s a product that’s good enough that I can release it into the outside world without feeling embarrassed. I accept the fact that it isn’t the best version of what I’m capable of, and I remember that I can improve it down the line.

Here’s a real-life example. In 2004, I created a 2-day course that was about the weakest MVP I’ve ever created. People paid me for it. They loved it. What’s more important, though, is that based on their feedback, I’ve revised that course about 50 times in the last two decades. (No joke!) Getting it “out there” has a great benefit that can’t happen unless you just go for it.

First fix: Commit to creating an MVP. Accept that, by definition, it’s not the best version of what you could create.

Take your deadlines seriously every day

Deadlines are hard when you’re self-employed or own your own business. When you’re not answering to anyone — when the buck stops with you — it can be easy to let your deadlines float past. But with a little self-knowledge and a whole lot of discipline, you can meet your targets and move toward your goals!

If you had to name only one reason you’re not delivering on deadline, what would it be? Let me know in the comments below!