How much effort should you put into a struggling employee?
- mayadolgin
- Sep 9, 2025
- 3 min read
(August 19, 2025 Newsletter)
A question I often hear from clients is “How do I know if it’s worth it to invest in that team member who’s not performing up to standards?”
If you’ve wondered this, the following experience will be familiar to you: you’ve been giving feedback and direction, checking in and following up, sending reminders before (or after!) deadlines, and it feels like nothing is working. Or it works temporarily but the person slides back into their old habits.
It’s legit to wonder at some point whether your efforts are for naught.
Why it matters
Your time is limited, but so is the mental and emotional energy that you’re spending on this team member.
One of your core functions as a people leader is to grow your team members’ potential and capacity, but you shouldn’t be working harder at it than they are.
And on the other hand, the sunk cost of the time you’ve already invested in them, from hiring and onboarding to ongoing support, can be a tough pill to swallow.
Plus, if you think the position will be hard to fill and the burden on you and/or your team in the interim will be too much to manage, you can start to second guess your instinct that it’s time to move on.
How to decide on next steps
Here are some criteria that can be helpful in making this difficult decision.
What other ways would you describe the situation? Once we dig into it, it becomes clear whether you believe the person cares about the mission of the organization and whether they see themselves there in the long-term. Are they doing their best, sincerely, but are struggling to keep up? Or are they checked out and doing the minimum to slide by? Do they express interest in other aspects of the team or organization’s work and just less in their own?
What else is being impacted besides their work product? Is their low performance impacting just you? You and the team? Other departments? What are the ripple effects of them missing deadlines, handing in sloppy work, or having a poor attitude? This can help determine the severity of the situation.
Check your own motivations. Ask yourself? Why do you want to support this person? Why else do you want to support them? Why do you really want to support them? If you came to an answer that’s about lifting this person up, keep going. If it’s about saving your own reputation, reconsider short- and long-term impacts.
What’s the worst that can happen? What’s the best that can happen? Play out both directions. That’s a great way of checking the risk involved.
Who else on the team needs your attention? If you’re neglecting your best people by spending too much time on your worst performing team members, it’s time to rebalance the effort.
Your next steps: Once you’ve determined whether you want to continue investing in this person, your response could range from:
Having a serious conversation about your concerns and goals and their aspirations, and discuss next steps together.
Begin the process of putting them on a PIP or just exiting them.
See whether they’re more interested in another role that might be opening up somewhere else in the company.
Final thought: It’s always worth considering how you might be contributing to the problem. Are you not being clear enough in how you assign work? Do you take over too quickly when the person hits a roadblock? There is always something you can learn from these moments. Don’t miss that opportunity.
The Coaching Corner
Coaching up
For some of you, coaching your boss comes easily and for others it requires sensitivity and courage. It means showing up as a thought partner and challenger. A few ways it could sound:
When being assigned something that is unclear or too vague: “I want to make sure I’m taking care of this to your standards. Could you paint some more of the picture for me on…?”
When they’re being a bottleneck: “I know you have a ton on your plate. What can I help with so you can review that doc soon?”
When you’ve been asked to do something out of the blue, “I’m sure that is important. Could you walk me through how it fits into the org goals we’ve talked about?”
Recommendations
“Perspective” – a lovely 3-minute video that everyone here should watch. No spoilers; I’ll just say that it lifted me up when I saw it.
“Now is the time for courage” – 5 steps that anyone can take to cultivate courage. I’m all on board with making all 5 of these top habits to pursue.
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