Is your employee missing deadlines again, and you’re running out of ways to address it without sounding like a broken record? In this week’s Q&A, HR expert Jane Harper dives into one of the most common (and frustrating) workplace challenges: how to handle employees who consistently miss deadlines without turning into a micromanager. From uncovering the root causes of poor time management to setting clear expectations and fostering a culture of accountability, Harper shares practical strategies to boost productivity while keeping empathy intact.
A reader writes:
Dear Jane,
I have a designer on my team who’s talented and creative but constantly misses deadlines. Every time I assign a task, it gets delayed with new explanations. While the end results are great, the delays are frustrating and throw off everyone else’s schedules.
I’ve tried gentle reminders, setting clearer timelines, and even checking in mid-week. Still, this employee keeps missing deadlines and somehow makes it sound reasonable every time. I don’t want to demotivate them, but I also can’t let this habit affect team morale and project flow. How do I handle an employee missing deadlines without becoming that boss who hovers over every move?
Jane’s advice on managing employees who miss deadlines
Whether it’s procrastination, burnout, or lack of clarity causing delays, this piece will help you strike the perfect balance between compassion and performance and finally get those projects back on track.
Diagnose Before You Discipline
Not all employee performance issues are created equal. Sometimes an employee missing deadlines is actually a symptom of unclear priorities, too many simultaneous tasks, or lack of resources. Start with an open conversation. Ask what’s causing the delay, workload, distractions, or unclear expectations. This turns the situation from blame to problem-solving.
Make Accountability a Habit, Not a Punishment
If the employee keeps missing deadlines even after discussions, set specific check-ins. Instead of micromanaging, establish progress markers. For example: “Let’s review the first draft by Wednesday.” This keeps accountability active without feeling intrusive. Remember, managing employees who miss deadlines is about structure, not surveillance.
Connect the Dots for Them
When deadlines slip, remind them how it affects others. Show how one delay can snowball into team productivity problems. Most employees don’t intend to cause chaos they just don’t see the bigger picture. Framing deadlines as collective goals rather than orders helps people take ownership.
Address the Behavior, Not the Person
Avoid framing the issue as “you’re always late.” Instead, try “I’ve noticed the last few projects went past deadline what can we change to prevent that?” This keeps the tone constructive and prevents defensiveness. Handling difficult employees effectively often comes down to communication, not confrontation.
A missed deadline here and there isn’t a crisis but a pattern is. The art of dealing with poor time management at work lies in empathy balanced with structure. Be supportive, set clear expectations, and follow through. Great leaders don’t just chase timelines they teach accountability.
Are you facing a tricky workplace dilemma? Write to Jane Harper with your questions on workplace conflict, policy issues or people management problems. Your situation could be featured (anonymously) in a future column.
Don’t let the changing world of work derail your hiring instincts. Send in your HR queries with the subject line ‘Ask JANE HARPER’ at info@thehrdigest.com.
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