How to Be Agile with Deadlines

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November 2014
by Taffy Williams
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deadlineI am an evangelist for entrepreneurial agility because of what I’ve observed and what I’ve experienced. I know the huge contributions small business pioneers have made in every industry, and I know they were able to make these contributions because they adapted quickly to changing environments and they were open-minded about new approaches and willing to test various options to see what worked.

Today, the need for agility is greater than ever before, but many entrepreneurs commit the sin of rigidity when dealing with deadlines.

Some dates, such as those set by governmental regulatory agencies, must be adhered to. Others, such as schedules for getting products to market, may require some flexibility to accommodate unexpected problems. Agile entrepreneurs can differentiate between these two types of schedules and between external and internal deadlines, those imposed by individuals and organizations outside the company, and those that the entrepreneurs impose upon themselves.

Perhaps most important of all, agile entrepreneurs are able to speed up or slow down as situations dictate.

Wiggle Room Possibilities

To differentiate between deadlines that are absolute and ones that only appear that way, you need to test your deadlines with “what-ifs.”

  • What if I miss the deadline? What’s the worst thing that can happen?
  • What if I find a way to expand my time frame? How much would it cost me in dollars and effort?
  • What if the deadline is mostly in my head?

Some deadlines have more give in them than is apparent. This is especially true for regulatory deadlines, investor-related dates, and loan repayment dates. Regulatory agencies may be willing to extend deadlines for filings and payments if you agree to pay a penalty, a penalty that might be easier for the business to tolerate than adhering to an impossible deadline. Similarly, investors may talk tough about time frames but they too are often willing to extend deadlines if entrepreneurs make convincing arguments.

Also, there is more than one way to meet a deadline. You can partially meet a deadline or milestone and buy yourself more time. For instance, you may be able to ship half of a customer’s order on the delivery date and send the other half a week later. Not every customer will accept this arrangement, but some will be fine with it, especially if you sweeten the new deal by providing a discount for the next order.

Agility in dealing with deadlines also involves dealing with the ways other people approach them.

Most entrepreneurs charge toward deadlines like bulls toward red capes, and they become impatient and frustrated when others slow their charge. Verbalizing frustrations and pushing people too hard can alienate them and/or lead them to make mistakes in a rush to get a project done.

Of course, some entrepreneurs view due dates with indifference or disdain, preferring to work at their own pace. Their attitude can also frustrate the people they work with, especially important people such as investors and partners.

If you know you’re going to be working with an investor who is a stickler for meeting dates, then you need to have a conversation at the very start of the relationship about attitudes toward delivery dates, and about how you’re going to handle situations when you can’t deliver on time. Perhaps you can agree on resetting the deadline immediately after it’s missed, maybe via a conference call.

Setting Dates

Out of necessity, entrepreneurs tend to sell hard in presentations, attempting to build enthusiasm that will translate into financing, sales, publicity, and profitable new relationships. And sometimes they become so revved up about the projections and the company’s future that they unnecessarily lock themselves into dates that are unrealistic or cannot be met.

Raising stakeholder expectations and then failing to meet them can be disastrous. It’s far better to set realistic dates from the start.

More specifically, to avoid date inflation, the agile entrepreneur should do the following:

  • Set dates for presentations and meetings well in advance, before the excitement of the moment sets them for you.
  • Provide date ranges, rather than specific dates, when possible. A range of a week, a month, or even longer will improve the odds of your being able to deliver as promised.
  • Re-evaluate deadlines and milestones regularly. Periodic meetings will give people an opportunity to tell you if they are on schedule. If they’re not, they may be in the best position to help you recalibrate various key dates through discussion and debate.

Negotiation Know-How

Many small business owners are skilled at negotiation, yet sometimes they shy away from negotiating deadlines imposed by others. As noted, it’s possible to negotiate even if you’re dealing with a governmental agency. But it’s not possible to bargain with the government or with any group or individual if you don’t try. While not every deadline is negotiable, some are. To capitalize on these situations:

  • At the Very Beginning of a Deal Question Whether Deadline Dates Can Be Moved if Circumstances Change

Pose likely scenarios that may impact a deadline: a delay in funding, for instance, or a slowdown because of a complex manufacturing process. In essence, you’re setting the stage for negotiating the date somewhere down the line. It may not be necessary, but broaching the subject at the beginning increases the likelihood of amenability to date bargaining later.

  • Assess and Use Your Leverage.

You may possess little or none, especially if you’re dealing with a regulatory agency or a big bank. But sometimes you do have leverage because of your history or relationship with a deadline-maker. Remind the deadline-maker about what’s at stake and about how stretching the deadline might improve the odds of getting a return on the investment. Refer to relevant experience (maybe the money you’ve generated for the deadline-maker in the past) and to previous discussions (perhaps, for example, the deadline-maker insisted at the beginning that you could have the business up and running in nine months). Most people don’t respond well to whining or begging, but leverage might buy you more time.

  • Trade For Time

Agile entrepreneurs recognize that they may have to give something up to obtain an extension. Ask yourself two questions: (1) How much additional time do I require? And 2) Is what I have to offer in exchange adequate?

If you need just an extra day or two, you probably don’t have to offer much, maybe a slightly increased financing rate or return percentage for investors. But if you require weeks or months, then you might have to give a lot, such as a larger percentage of ownership of the business or a promise to pay a relatively large penalty for being late.

And you might have to think more creatively if you lack the ability to trade financial incentives for time. Perhaps the deadline-maker could use your services at a discounted rate for some other project. Perhaps an offer of your technology or your people for some other purpose would appeal.

Ask, “Is it Me?”

I emphasized earlier that entrepreneurs must distinguish externally imposed deadlines from internally imposed ones. When small business owners are starting up they often create unnecessarily tight time frames. They honestly believe that their deadline and milestone dates are dictated by the market, but the dates are actually set by the entrepreneur’s highly aggressive, competitive nature.

The advice here is simple to offer and difficult to follow: Don’t let your ego get in the way of setting realistic deadlines. Entrepreneurs need big egos to succeed; they’re often Davids operating in a world filled with Goliaths, and they rely on their self-promoting abilities. But ego can get in the way of agility.

Take a step back when you decide on an ambitious deadline and determine whether that date is fair for you, your people, your customers, and your partners and/or investors. Ask yourself if it will take a miracle to hit the dates you’ve decided upon or if hitting them will just require a strong effort and a bit of luck.

Key Questions

Assessing your attitude and actions in relation to milestones and deadlines can do a lot to increase your agility. To evaluate your time-frame attitudes and behaviors, answer the following questions:

  • What types of deadlines cause you the most anxiety or give your business the most problems? Regulatory filing requirements? Loan repayments? Investor requirements? Your own internally generated objectives?
  • How do you respond to this anxiety or these problems?
  • Do you drive your people and yourself to the breaking point in order to meet deadlines? Or do you miss deadlines routinely, figuring that you can always get extensions?
  • Do you ask yourself “what if ” questions to determine the ramifications of meeting or missing a set deadline? Do you think and talk about what might happen if you were to ask for an extra week from the person or group setting the deadline? Do you examine whether the deadline is real, or one that you’ve insisted upon?
  • Do you engage investors, business partners, employees, and others in discussions about how you deal with deadlines and other key dates and how they deal with them? Do you have these conversations well in advance of key dates? Do you find a way to compromise with people whose styles clash with yours, or at least a way to agree on techniques to manage them if they become an issue?
  • Are you guilty of setting highly ambitious deadlines in a spur-of-the-moment speech or conversation?
  • Do you usually try to negotiate time frames with various outside groups, investors, banks, government agencies, customers, and suppliers, or do you generally assume that deadlines are hard? Do you find that your pride or stubbornness prevents you from broaching the topic?
  • Are you honest with yourself when it comes to time frames? Can you step back and think objectively about your motivations for setting a certain date?

If you find yourself answering these questions in ways that suggest you have a rigid attitude toward various due dates, that’s a great first step toward becoming more agile. Once you’re disturbed by this realization, you’ll be motivated to change, to ask the “what if ” questions, negotiate deadlines, and do the other things that increase your flexibility.


Taffy Williams has been an entrepreneur and advisor to entrepreneurs for more than 30 years. The founder and president of Colonial Technology Development Company, which assists start-ups in technology commercialization, he writes the Startup Blog as well as articles for Examiner.com. This article is derived, with permission, from his book, Think Agile: How Smart Entrepreneurs Adapt in Order to Succeed. Copyright 2015 Taffy Williams. Published by AMACOM Books, a division of American Management Association, New York, NY. All rights reserved.

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