Deadlines? Ha! Don’t Make Me Laugh

By Steven E. Sacks, CPA, CGMA, ABC

Distractions, distractions and more distractions coupled with deadlines. Ah, deadlines! Those are the bête noire of executives, journalists, record producers, book authors and anyone else in the workforce whose deliverables are expected by a certain date. And what about those dates? Are they arbitrary or do they have the real urgency of, say, a court order?

I researched the origin of the term deadline and found that it can be traced to the Civil War. A line was drawn in the sand around a prison or near a detention fence. Any prisoner who went beyond the line in the sand would be shot. Later on, the term deadline shifted to the publishing sector, mainly for newspapers where an article had to be submitted by a certain time or it could not be included in the paper. Overtime, the term applied to other areas of work that was schedule-driven.

If you want to control actions and behavior in the workplace, you have to set deadlines. It is, however, a double-edged sword: it prevents dilly-dallying but also de-emphasizes refinement with the aim of perfection. What usually results is the philosophy of “Don’t let the perfect be the enemy of the good.”  This may be relevant for a tweet or a Facebook post, but for important matters, not so much.

In deadlines for home renovations, unveiling of a new smartphone, tax filing, or a bevy of any time-mandated activity, deadlines are often ignored. You can easily find IT project management efforts on a junkpile of missed milestones or incompleted phases. The culprit: missed deadlines.

What are the causes of deadlines turning to dust?

  • Ineffective communication. The people in charge of the project don’t effectively communicate its importance or purpose. They will think others will automatically understand it. I’ve worked with clients who believed a step in the process was unnecessary and a waste of time. While they understand the wishes (or mandates) of management, they’ll go through the motions of completing the step, but not with the desired alacrity.
  • Lack of real listening. A cause of this is people disbelieving the project has no way of being accomplished for whatever reason. It could because of the scope, limited resources both financial and human, or no acknowledgement of how each person’s effort can play a role in completing the project on time. At some point, people will tune out the messenger.
  • Inability to have a voice. Those who are involved in implementing the phases of the project believe the timelines are unrealistic, but they don’t have the confidence, influence, or courage to speak their mind, with the goal of giving the decision makers a reason to reconsider their plans. What happens is that no one says anything. If one person happens to voice an opinion, he or she may not do so in a convincing manner, thus reducing the impact of their insight in the minds of the project managers.
  • Inconclusive advance information. The deadlines are established without knowing the necessary elements for the project to be a success. It is baffling and counterproductive to have those who are not responsible for a project’s implementation to set an arbitrary completion date and expect those responsible for the implementation to adhere to that date.

Teams, whether virtual or in-person, need some guidance as to the plans, expected outcomes and, of course, the deadlines. While it is normal to detest deadlines, particularly those that cannot be justified, they do, however, provide a positive effect in the form of careful planning, the search for alternative approaches and, hopefully, better teamwork.

If you want to be honest about and effective with deadlines, conduct a retrospective of those initiatives whose deadlines were clearly explained and embraced with those that were disregarded. Determine the approaches taken to establish real and realistic deadlines and compare them with those deadlines that proved to be abject failures.

Once you can identify the differences in the successful projects versus those that failed, you can amend how you approach establishing deadlines.

If you fail to undertake this assessment, then deadlines will continue to be an eye-rolling, snicker-inducing exercise — probably akin to throwing a dart at a calendar while blindfolded.


About the Author

Steven Sacks is the CEO of Solutions to Results, LLC, a consultancy that specializes in helping individuals, firms and organizations meet the challenges of communicating with clarity and purpose. Visit his website at