“I just don’t get it.”
That’s what Lisa kept saying during our coaching session.
Lisa, a VP at a fast-growing SaaS company, was frustrated with one of her direct reports, Matt, a Senior Director of Engineering.
Matt had been putting off making a final hiring decision for weeks. The position had been open for months, the hiring pipeline was strong, and yet—he kept delaying.
Lisa was floored.
- “We need this hire—yesterday.”
- “He’s the hiring manager, not me. Why am I more concerned about filling this role than he is?”
- “This delay is putting extra work on his team. Doesn’t he see that?”
The deadline was here. If Matt didn’t make a decision, they’d lose top candidates to competitors, and his team would remain overburdened.
Sound familiar?
If you’re leading a team, you’ve likely run into this exact challenge—a high-performing direct report who inexplicably delays a critical, time-sensitive task.
So, what’s really going on? And more importantly, how do you help them without micromanaging?
Let’s dive in.
What’s Really Happening? Different Work Styles, Different Priorities
The first thing Lisa needed to recognize was that Matt wasn’t ignoring the hiring process because he didn’t care. In fact, Matt was deeply invested in hiring the right person—but his natural work style meant that:
✅ He prioritized accuracy and risk reduction over speed.
✅ He wanted more data to be absolutely certain about his decision.
✅ He was overanalyzing every candidate instead of moving forward.
Lisa, on the other hand, was a fast-moving, big-picture thinker who thrived on decisive action. She saw the hiring process as a strategic business decision that required momentum.
Matt saw it as a high-risk decision that required deep analysis.
This is where leaders need to adjust their approach to time management—both for themselves and their teams.
How to Help Your Team Manage Time Without Micromanaging
As a leader, you don’t just manage your own time—you help your team manage theirs.
Here’s how you can support different work styles and keep critical tasks on track:
1. Define Priorities Clearly (And Early)
What Lisa Did: She assumed Matt saw the hiring decision as an urgent priority.
Better Approach: Make it explicit. Instead of “We need to hire someone ASAP”, say:
💡 “The team is stretched, and every week without this role filled adds more strain. Let’s commit to making a final decision by Friday.”
✅ Call out potential bottlenecks early. Ask, “What’s slowing down your decision?”
✅ Break down large tasks into smaller, manageable deadlines.
For high-detail team members like Matt, giving structured timelines reduces the feeling of overwhelm.
2. Align on the “Why” (Make It Meaningful)
People aren’t motivated by deadlines alone—they’re motivated by outcomes that matter to them.
Instead of: “We need to move faster.”
Try: “The longer we wait, the harder this workload gets on your team. What do you need to feel confident in your decision?”
✅ Tie tasks to personal and team impact.
✅ For detail-oriented leaders, frame it as a risk-mitigation issue. (e.g., “By hiring now, we reduce burnout and prevent turnover in your team.”)
✅ For strategic thinkers, connect it to business goals. (e.g., “This role will help us hit our next product milestone faster.”)
When team members see the purpose behind the task, their motivation shifts from compliance to commitment.
3. Offer Structure, Not Micromanagement
Lisa’s instinct was to keep checking in, but that only led to frustration. Instead, she needed to offer structure that supported Matt’s workflow.
Better Approach:
✔ Set check-ins in advance. Instead of last-minute pressure, schedule progress updates. (“Let’s touch base midweek to review final candidates.”)
✔ Provide decision frameworks. If someone is overanalyzing, give them clear criteria to follow.
✔ Ask, don’t assume. Instead of saying, “Why haven’t you done this yet?”, ask:
“What’s holding you back from making the final call?”
For highly analytical team members like Matt, this approach reduces resistance and increases accountability.
4. Recognize That Time Management Is Emotional, Not Just Logical
Most leaders assume time management is about organization and planning. In reality, it’s about emotional regulation.
Common emotional blockers:
❌ Overwhelm – “What if I make the wrong hire?”
❌ Perfectionism – “I need more data before making a decision.”
❌ Avoidance – “If I delay, I don’t have to deal with the pressure yet.”
To help your team break through these blocks:
✔ Acknowledge the challenge. (e.g., “I know hiring is a big decision. Let’s make the best choice with the info we have.”)
✔ Encourage a ‘draft-first’ mindset. (e.g., “We can always refine the hiring plan if needed.”)
✔ Coach through barriers. Ask, “What’s the hardest part about this for you?”
Final Thought: Lead by Example
At the end of the day, time management isn’t just a personal skill—it’s a leadership skill.
Your team isn’t just looking at what you tell them to do—they’re looking at how you handle priorities yourself.
The best leaders don’t just manage their own time effectively—they empower their teams to do the same.
