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5 Ways to Never Miss a Deadline The good news is you won a big contract. The bad news is you committed to do the impossible.

By Steve Tobak

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Opinions expressed by Entrepreneur contributors are their own.

The good news is you won a big contract. The bad news is you committed to do the impossible.

Deadlines trip up most entrepreneurs. They're the direct cause of quite a bit of lost repeat business, not to mention a ridiculous amount of stress. The problem is that time and money are always intertwined because nobody gets paid until somebody delivers the goods. That goes for both you and the customer, if it's B2B.

Nothing teaches you how to deal with crazy deadlines better than putting your butt on the line as a top executive in a publicly traded company. That's what I did for more years than I care to think about and, while the pressure was enormous, entrepreneurial life seems like a walk in the park by comparison.

Whatever business you're in, meeting deadlines always comes down to estimating two data points: 1) When does the customer really need it, and 2) How long does it really take for you to deliver the goods. This is how to make those guestimates as accurately as possible and communicate with the customer along the way.

Know how long it takes to do your job.

I know that seems obvious, but few entrepreneurs understand the importance of that competency. Just remember you live in the real world where there's just one of you, one of each worker involved, and a finite number of working hours in a week. Don't laugh; you'd be amazed how many people screw that up.

At the end of every project, make sure you assess the accuracy of your initial forecast to improve future quotes. In time, you'll get very good at it.

Related: 7 Signs of a Future Success Story

Determine the customer's real plans.

When customers tell you to jump, your initial reaction will always be to say, "How high?" You need to resist that urge and learn to ask questions and find out as much as you can before providing any answers.

To be specific, when customers ask, "When can you deliver?" your reply should be something along the lines of, "When do you need it?" or "Can you tell me more about your project?" Always get information before you give it. Sometimes you have to do a little digging but that's how you build buffers into your schedule without risking the business or your credibility.

Also remember that things change. Even after you've committed to a schedule, it's a good idea to stay up to date and see if you've acquired any wiggle room – without setting off any alarms, of course

Always be honest … with yourself.

While you need to know how well you're tracking to your forecast, it's equally important to be smart about what you tell customers. Never communicate more than you have to. Remember, not every schedule slip or milestone miss is critical and it may do far more harm than good to share too much information.

Always develop an aggressive internal schedule and have the discipline to stick to it religiously. Why? Things will go wrong. They always do. And when they do, you don't want it to impact the schedule you committed to, which you've hopefully had the foresight to pad as much as possible.

Related: The Only Good Reasons to Start a Business

It's OK to commit to the impossible.

You will be asked to commit to the impossible. That can't be helped. In fact, it's not necessarily a bad thing. The biggest, most successful companies on earth always ask the world of their vendors – and they usually get it because everyone wants their business.

Just do one thing before you sign on the dotted line: Tell the customer something along the lines of how important their business is to you, that it's going to be a real challenge, but they're your top priority and you'll move heaven and earth to meet their schedule. Then do it.

What to do when you screw-up … and you will.

If you miss a deadline, and you probably will, don't beat yourself up. Well-managed companies usually build in some padding just in case. In the unfortunate event that your miss legitimately harms the customer's business, you can still recover and perhaps even create an opportunity to build a stronger relationship. It just depends on how you handle it.

Granted, it's a tenuous situation, but once you know you've passed the point of no return, you want to come clean and tell them exactly how you're going to do everything in your power to make it right. If you perform well when your butt's on the line, that should actually improve your credibility and their trust in you.

Nothing builds a stronger customer relationship than going through hell together.

Related: 10 Things Successful People Do Differently

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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