10 Questions To Ask When Your Team Keeps Missing Deadlines

Read Time: 4 minutes.

I got a frantic text message from a CEO I coach this week:

"I'm so frustrated with our data analyst. He's spent weeks on an issue that should have been handled in a few days. And it's taken so much of my time and energy. The only path I've found to help him is to give him small, discrete tasks. For example..."

I wish this situation were uncommon.
Or that his reaction is unusual.
But neither would be true.

There's a large grey area between "hire smart people and get out of their way" and "we'll only succeed if I micromanage every step of every task."

That grey area is called management.
When done well, it's called leadership.

But that quick-twitch pendulum swing from space to succeed to deep in the weeds is understandable.

• We're under pressure to deliver results.

• We're competing with other talented companies.

• We're trying to maintain the high standards that succeed.

But before you take over someone's work, learn why they're coming up short. There are reasons they fall short other than they're incapable.

If you uncover that reason, you can tailor your solution to it. And in doing so, you can often get the outcome you want without taking on their work.

They remain responsible and empowered.
You remain leveraged and leading.

Here are 10 possibilities:

Context Gaps

Team members misinterpret requirements, miss crucial context, or misunderstand priorities. The solution is to reset expectations explicitly, document definitions of "done," and break work into visible chunks they can track.

Capability Mismatch

The assigned work exceeds current skill levels, but pride or fear prevents admission. Address this by assessing skill gaps, providing targeted training, and matching tasks to current capabilities while building toward growth.

Capacity Overload

Multiple competing priorities and constant context-switching create the illusion of progress while actually slowing everything down. Fix this by auditing their full workload, eliminating unnecessary tasks, and creating team-wide protected work time.

Confidence Issues

Perfectionism and imposter syndrome create paralysis, leading to endless revisions while avoiding transparency. Make it safe to make mistakes, celebrate incremental progress, and engineer early wins to build momentum.

Communication Blocks

Fear of delivering bad news leads to silence until crisis points. Counter this by modeling vulnerability yourself, visibly monitoring for early warning signals, and reinforcing a culture that celebrates asking for help and doesn't tolerate hiding problems.

Coordination Problems

Dependencies on other teams or resources create hidden bottlenecks and delays. Prevent this by identifying dependencies early, creating clear, mutually agreed escalation paths, and building in realistic collaboration buffers.

Complexity Underestimation

What seemed simple reveals hidden complications, edge cases, and scope creep. Combat this by breaking down work upfront, explicitly planning for unknowns, and creating discrete phases for rework.

Chronic Distractions

The constant pull of meetings and reactive work prevents sustained focus on important deliverables. Fix this by auditing time allocation, creating protected focus blocks, and actively shielding from interruptions.

Cultural Misalignment

Differing standards of quality and urgency create friction and delays. Align the team by setting clear standards, demonstrating what excellence looks like, and establishing shared values around delivery.

Change Resistance

Attachment to old methods and passive opposition to new approaches causes subtle delays. Address this by understanding the underlying concerns, lowering the stakes through experiments, and creating genuine ownership in the new direction.

The Bottom Line

Speed doesn't come from pressure. It comes from properly diagnosing the root cause and addressing the real barriers your team faces.

Next time work is late, resist the urge to push harder. Instead, use this framework to step back and fix the underlying problem.

Your team will thank you.
And more importantly, they'll more than make up the time you invest.

What You Missed This Week

The big new in our house this week:

⭐ Mar crossed 10,000 followers on LinkedIn.⭐

Please give her a follow if you’re not already.

Did you miss last week’s Monday MGMT Minute? 

📌 How you can avoid getting caught up in the What-If trap.

And here are our 5 most popular posts from this week:

1. 11 Promises Every Manager Should Follow

2. 8 Mind-Bending Cognitive Biases

3. Master The Art Of Managing Up

4. Questions to Ask Before Taking A Job

5. How To Find Manager Success At Different Levels

Our goal is to build a community of 1 million thoughtful, curious leaders.

Your ♻️ reposts on any or all of the above are always appreciated.  

Thank you for reading. Appreciate you!

Dave & Mar