We’ve all had that moment: staring at an impossibly long to-do list while our boss casually adds “just one more thing” to our plate. That sinking feeling in your stomach grows as you wonder how you’ll possibly get it all done—and whether bringing it up will make you look incompetent.
Recently, one of our Optimism Library subscribers brought this question to our attention: “My to-do list is out of control and my boss keeps piling on more. What’s the best way to have that awkward ‘I’m drowning here’ conversation without sounding like I can’t handle my job?”
We took it to Simon, and here’s his response.
It’s Not About Workload—It’s About Priorities
You first need to reframe this entire conversation. “Instead of talking about workload, talk about work prioritization,” says Simon.
Rather than positioning yourself as someone who can’t handle the volume (which could indeed make you look incapable), you’re positioning yourself as someone who wants to deliver the most value.
The Magic Conversation Starter
Simon suggested this approach: “Say: ‘Boss, I need your help. I’ve got a ton on my to-do list. Can you help me prioritize? I want to make sure I’m spending my time on what you think are the most important things.'”
What’s brilliant about this approach is that it accomplishes several things at once:
- It shows you’re taking ownership and being proactive
- It positions your boss as the expert whose guidance you value
- It focuses on delivering results, not just activity
- It makes the prioritization a shared responsibility
The Follow-Through That Changes Everything
The real power comes in the follow-through:
“Then, when your boss gives you something new, say: ‘No problem. Here’s everything in priority order. Where would you like me to put this?’ And start with number one.”
By continually bringing the conversation back to priorities rather than capacity, you shift the dynamic. Your boss now shares responsibility for deciding what gets done first—and what might not get done at all.
“Remember, employers pay for results, while employees want to be paid for effort,” says Simon.
This disconnect is at the heart of many workplace frustrations. Your boss doesn’t care that you completed 400 tasks if the two most important ones didn’t get done. By focusing on prioritization, you align yourself with what your employer actually values—results on the most important tasks.
Making It Work
Each time your workload increases, you bring it back to priorities:
“By having the boss take accountability for priorities, you take accountability for working through them in order. People get upset when important tasks aren’t completed, not when your list remains long.”
Sometimes, just seeing the full list of prioritized tasks will prompt your boss to say, “Actually, never mind, I’ll do it.” Other times, they’ll help you re-prioritize, ensuring that the most critical work gets done.
The Bottom Line
We all face overwhelming workloads at times, but how we address them can make all the difference between appearing overwhelmed and appearing strategic. By shifting the conversation from capacity to prioritization, you demonstrate your commitment to results while creating a shared responsibility for managing the workload.
Facing a challenge at work? Maybe Simon can help. As an Optimism Library subscriber, you’re invited to our exclusive quarterly Live Q&A sessions where you can ask Simon your questions directly.
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