Getting Employees to Meet Deadlines without Nagging

Help employees meet deadlines. Stop missed deadlines from the start. Create a game plan. Get past lame excuses. Ask proactive questions to get employees to take ownership for their projects, and learn to follow through.

Employees and sales reps not meeting deadlines is a major factor in low sales team performance. As a leadership coach, exasperated supervisors and sales managers often plead with me to supply effective methods to improve employee time and goal management skills.

Take a look at this scenario with Heidi and Rodney

Heidi is the team leader. Rodney is a project coordinator on her team.

Rodney is called into Heidi’s office. He could tell immediately by the look on Heidi’s face that she was struggling to keep her composure in check: “Rodney, I thought we agreed three weeks ago to get this project finished by now. Now I’m hearing it’s nowhere near ready. What gives?”

Flustered, Rodney says, “I’m doing the best I can, and I’ll get to it as soon as possible.”

When someone like Rodney makes a habit of postponing certain tasks, procrastinating on his to‑do lists, and failing to meet agreed-upon objectives, it’s maddening for the superiors like Heidi who count on him. Even the most understanding managers can find themselves in badgering mode when employees continually don’t meet deadlines and desperation grows. You might even play the “distrust card,” where you lose total faith in that person.

So how do you deal with someone like Rodney? Don’t worry, there’s light at the end of the tunnel. Many times when trying to find out why an employee can’t seem to meet deadlines, out of desperation, you might ask a question like the following:

  • You told me you’d get this project to me two weeks ago.
  • I’ve asked for it several times now, and I still haven’t seen it.
  • I don’t understand. Why isn’t it done yet?

These type of questions usually will not get you very far. Many times the employee will give whiny, vague responses? However, getting negative or ambiguous feedback can be a blessing in disguise, giving you a heads-up that something isn’t right and you must view this information in a clearer light.

Get to the origin of why employees don’t meet deadlines

Sometimes managers say, “What do I need to do to help you get this done?” We think we’re being a resource for the employee, but we’re actually undercutting his confidence. He ends up feeling scolded. Or worse, he becomes aloof, or skittish, and avoids you, because he thinks you’re angry. He feels under-the-gun. Ironically, the manager thinks she’s “done good,” by creating a sense of urgency for this individual,. But instead, she has taken ownership of the problem for herself. A terrible strategy — she’s now doing her employee’s work.

Rarely do managers want to go down that nagging path where they constantly buttonhole employees with, What’s going on? Why isn’t this ready?” Despite the best intentions to stay cool and professional, the manager’s frustration inevitably is revealed in their words or tone of voice.

Create a game plan to meet deadlines from the start

Here’s a proactive approach used by Heidi: 

  • “Hey, Rodney, it sounds to me like you’ve been incredibly busy.
  • As you know from our conversation last week, we were talking about getting this project completed next Friday, one week from today.
  • So tell me, how are you progressing so far?
  • Walk me through the steps you’ve implemented since we spoke last week.” 

Heidi then listens very closely to Rodney to find out what he’s initiated so far and what he hasn’t, as well as any other potential issues that might creep up.

Suppose Rodney says either one of these statements…

  • Well, things have been really busy around here, but I plan on getting the project done as soon as I can.
  • Well, it’s gonna be late, probably a week later than I would like.

In response to this, Heidi has three choices:

  1. She can say, “Okay, I can live with that.” But probably not!
  2. She can negotiate with Rodney and agree upon a more realistic timeframe if needed. Determine if there’s wiggle room to give Rodney a day or two, versus his usual week or more of being late.
  3. She can recognize the sense of urgency here. After all, Rodney and Heidi had already agreed that the project was supposed to be finished by next Friday. This could easily become Heidi’s problem instead of Rodney’s, but since this is really Rodney’s issue, Heidi needs to keep the onus on him. She may tell Rodney, “I’m sorry, but I’m afraid going beyond next Friday’s deadline is unacceptable,” adding an open-ended question that will encourage Rodney to specify dates and provide feedback: “How can we ensure that we’ll stay within our agreed-upon timeline?”

Getting past the lame excuses why employees can’t meet deadlines

Now that he has a fire lit under him, Rodney can respond, “Okay, I can realistically get this done by next Friday.”

Heidi needs to stay in charge and confirm Rodney’s action plan. “Great! What specific steps will you need to take between now and next Friday to accomplish this?”

Like many of us, Rodney has his quirks. Maybe he’s a procrastinator. Maybe he has multiple priorities that require him to multi-task, and his plate is already full. The bottom line: when next Friday rolls around, will Rodney’s project be ready? When Heidi follows up with Rodney, it’ll be unacceptable if he responds, “Oh, gosh, I’m going as fast as I can. This came up, that came up, and I just couldn’t get to it …I’ll get it to you next Monday.” He might as well be saying “whah whah whah,” like the adults in the animated Peanuts cartoons.

Rodney might blame his slow progress on lack of time. But pointing to time constraints can be a Band-Aid approach. Sometimes when people say, “I don’t have the time,” when you read between the lines, you may find they’re really saying:

  • “I can’t do it.
  • I don’t know how.
  • I feel too vulnerable.
  • I feel too insecure.”

Time management issues often result from an employee working outside his or her comfort zone. And sometimes the employee with just tell the manager what she wants to hear, to get her “off his back.”

Ask proactive questions to get employees to take ownership of projects, tasks, and goals

The best way to manage Rodney is to ask him proactive questions now, rather than reactive questions later:


  • “Why isn’t it ready? What have you been doing?”

This approach puts people on the defensive; bad move! You’ll cross that fine line between encouragement and nagging.


  • Rodney, walk me through the steps you’ll take to finish this project.
  • Do you see any potential obstacles that could get in the way?
  • If so, what are they?
  • What will you do to ensure you’ll have ample time to finish the project by our deadline?

This approach drives Rodney to articulate the physical actions and resources he’ll use, what potential obstacles he may encounter, and how he’ll overcome them. Be good-natured about it: “Hey Rodney, how are things progressing since we talked Wednesday?”

Here are some additional proactive questions to coach employees to meet deadlines

  1. What are your goals and timeline for this project?
  2. Take me through your action steps to get this project done by x
  3. How are you progressing with the project so far?
  4. Bring me up to speed where you are now compared to a week ago. 
  5. What’s working?… What’s not?… What are you going to do about it? 
  6. Explain to me what your plans are between now and next Monday.

Follow-Ups: Help your employees meet deadlines

Managers may say, “Yeah, those are good questions, but do I really want all these details or overly-precise explanations” Yes, you do! When you deal with someone like Rodney, and you want him to meet deadlines, you’ll want to know his level of commitment, willingness, confidence, and ability to follow through.

Action Steps:
If he can’t walk you through all the steps, that’s a red flag. Make sure the employee has a complete understanding of the steps and outcome desired. When he is able to articulate the action steps, this will cut back on the amount of “hand-holding” required by the manager.

Keep the lines of communication open with email conversations. Ask your employee something like this: “Great! So that I am kept in the loop, send me an email by the end of today summarizing your progress and next steps.”

Make the Employee Accountable:
Make this inquiry: “What will you do between now and this Friday to meet your deadline?”

Provide Ownership:
Reinforce your employees’ determination to stay on track and take ownership. As the manager, take the words “Here’s what you should (or need) to do” out of your vocabulary.

In my sales leadership business, I address this challenge with many of the companies and organizations I partner with.  Check out these two management workshops:

To learn more about my sales training, coaching, keynote speaking or workshops, contact Performance Based Results now!

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Paul Cherry

For over two decades, sales expert and author PAUL CHERRY has helped B2B sales professionals close more deals in all major industries. As a recognized thought leader in customer engagement strategies, Paul Cherry has been featured in more than 250 publications, including Investor’s Business Daily, Selling Power, Inc., Sales & Marketing Management, The Kiplinger Letter, and Salesforce.

Performance Based Results

Paul Cherry is the president of Performance Based Results. PBR delivers intense, customized sales team training programs and sales management coaching to companies throughout North America. Paul has worked with more than 1,200 organizations, including 175 of the Fortune 500, plus more than a thousand entrepreneurial, small to mid-sized, cutting-edge businesses looking to dominate their niche markets. Clients typically get 7 times their return-on-investment (ROI) or better.

Questions That Sell

Paul Cherry’s top-rated bestseller, Questions That Sell: The Powerful Process for Discovering What Your Customer Really Wants (AMACOM) has been listed on BookAuthority’s “100 Best Sales Books of All Time” and has been published in four languages. He is also the author of Questions That Get Results (Wiley) and The Ultimate Sales Pro (HarperCollins Leadership).