When you’re leading a team, there are few things more frustrating than missed deadlines.
It always puts you in a tough spot– you start wondering…
Should I follow up? How flexible should I be? Is this going to delay our launch?
There isn’t a hard and fast “rule” on how to handle overdue work or how flexible to be with missed deadlines.
But at a certain point, you might start to ask, am I being a supportive leader by being flexible with deadlines? Or just enabling a pattern that isn’t working?
Here’s the approach I use:
1- Be clear upfront.
Being clear isn’t just about sharing the due date– you also want to explain why it matters.
Is it part of a larger project where others are depending on that task getting done?
Is it client-facing work with a promised delivery date?
Is it an essential piece of a launch that has set timelines?
When people understand why something is important (not just when it’s due), they’re more likely to follow through.
2- Build in buffer time.
Whenever possible, I try to “bake in” spaciousness around due dates because I know things come up. People get sick, projects take longer, unexpected things come up. I get it, I’ve been there too.
I aim to assign due dates before I actually need something done so that if (okay, when) something runs late, we’ve got some cushion.
3- Address issues.
Yes, be understanding and empathetic if someone needs an extension. But also: don’t let it become the norm.
Take some time to dig into understanding why the deadline wasn’t met and whether it’s something that can be supported or solved going forward.
- Was the deadline that I set realistic given the scope of the project? Did I provide enough of a runway, as well as all the information and access they needed well in advance?
- Am I being clear in my expectations and sharing additional information and context that would be useful for them to understand why this is important?
- Have I made it clear what I expect around communication? Did they reach out to me about needing to extend the deadline, or did I need to chase them down to get an update?
- Is the team member overextended with their workload? Am I asking for something not included in our retainer?
- Do they understand how missed deadlines impact the team or the business (including me)?
4- If it’s a pattern and it’s not improving – let them go.
I don’t use a rigid “3 strikes” rule. Instead, I look for patterns and trends.
Is it something that has happened once or twice? → Not a big deal. That’s human, it happens.
Is it improving since we made xyz adjustments? Is there progress being made in terms of better communication, etc? → Great, let’s give it more time.
Or is it a pattern that (even after clear, direct feedback) isn’t actually changing? → That’s when I know it’s no longer a good fit, and I’ll let them go.
For me, perfection isn’t the goal. Deadlines will get missed from time to time– that’s just part of running a team.
Instead, my goal is to empower my team to take full ownership of their tasks and projects, to communicate things clearly, and to understand how their work fits into the bigger picture – so that everything can keep moving smoothly.
