The Skilled Manager’s Guide to Dealing With Underperformers

You can’t manage someone’s performance; you can only help them manage it themselves

Alex Jones
Nov 21, 2019 · 9 min read
Photo: Tom Werner/Getty Images, modified by Alex

Dealing with someone who isn’t performing at the level they should be is frustrating. It’s stressful. And honestly, it can be scary when it escalates to the point of needing to let someone go. It’s been the hardest part of my job, bar none.

It’s also one of the most important responsibilities that any leader shoulders. But here’s the thing: Our job isn’t to manage performance because frankly, we can’t manage another human’s performance.

Let’s pause for a second and think through how different life would be if we truly could manage how someone else performs, via a snippet from one of my favorite episodes of The Simpsons.

Homer: “Are you guys working?”
Team: “Yes, sir, Mr. Simpson.”
Homer: “Could you, um, work any harder than this?”
Team: “Sure thing, boss.”

Well, that was easy! We’re done here…

Okay, so back to reality: Telling people to work harder, faster, or better isn’t an effective tactic. Instead, what we can do is provide clear feedback in a timely manner and support the team members responsible for meeting, if not surpassing, our expectations.

While some performance issues aren’t recoverable, many can be addressed. And when they’re caught early enough, our investment is minimal (assuming the employee is invested in improving).

A bit of context

Just so you know where I’m coming from, here are some of the situations I’ve faced in my career:

  • As a new manager, I’ve had to fire someone I had previously promoted against my boss’s advice. This person lied about me to that same boss while I was sitting right there at the same table. And yet, this was still immensely hard for me. I wanted nothing else than to avoid the situation altogether. (I didn’t.)
  • I’ve provided feedback to people on other teams who came to me for perspective on how they should handle being placed on a performance improvement plan.
  • I’ve worked with people on my team who were at risk of being fired due to poor performance. In some cases, we were able to get them on the right path. In others, it was clear they needed a different environment to be successful.
  • I’ve had countless conversations with other managers regarding how to handle someone who isn’t performing, either because I needed a sounding board or they did.

Note that as tough as these situations are for us, there is no doubt they are much harder for the person on the receiving end.

To start: What are we talking about here?

Underperformance. As a concept, it seems pretty clear. Either someone is doing well enough or they aren’t, right?


Often, our goals aren’t clearly defined and measurement is subjective. (“Could you, um, work harder than this?”) What do we mean by “collaborates well with others” or “meets expectations?” Poor communication and misaligned expectations are key drivers for poor performance.

In these cases, the failure belongs to the manager, not the team member.

Take a second with that: It’s on us, not them.

But that’s good news, as it’s much easier for us to improve how we communicate than it is for us to get another human to make big changes. (Also, setting clear guidelines and communicating well are part of the job description of a good manager).

The different levels of feedback

Photo courtesy of WOCinTechChat

Daily, we’re expected to ensure that our team functions to the best of its ability, and that the people we serve have every opportunity to live up to their potential. For people who are performing well, we only need to provide the occasional nudge.

Providing clear feedback in a timely fashion is a hard skill to develop, but most people appreciate and can act on concise, actionable feedback when the situation is still fresh in their minds. In fact, motivated people want to improve and appreciate that you are there to help them.

Piling it all up until you “have the time” to address it or have “enough” examples to warrant a conversation will overwhelm the recipient, often putting them in a defensive position. At that point, they’re no longer looking to improve; they’re looking to get out of trouble.

Because of this, you should always deliver feedback in person and provide time for a discussion. No one appreciates drive-by feedback, and feedback delivered via email, Slack, or text has a very high likelihood of being misinterpreted.

And most important of all: Do not soften your feedback because you’re worried about coming across as mean. That’s just you trying to protect your ego.

“Clear is kind.
Unclear is unkind.”
- Dr. Brené Brown

If the same issue(s) crop up more than once, it’s on us to deliver the same clear feedback to ensure that it sinks in. But before diving in again, take the time to evaluate how you shared the feedback and recommendations. See if you can deliver the same message in a slightly different way that might be more effective.

As you talk, be sure to tie the new round of feedback to previous conversations. It’s important that you both to recognize the behavior as a trend that needs to change, not a one-time event.

It’s also important for the team member to understand that this is an opportunity to drive their own growth. As much as possible, they should define possible solutions while we provide light guidance or ideas. They won’t grow very much if we dictate exactly what has to change and how. (That comes later, if needed.)

Photo courtesy of WOCinTechChat

Sometimes providing clear feedback on what to improve isn’t enough. If repeated guidance doesn’t result in a positive change or if a particularly problematic issue has cropped up for the first time, we need to make the gravity of the situation crystal clear.

In these times, the manager’s role becomes more serious and more prescriptive. This may be a hard conversation but we must approach it with the intent of helping the employee hit expectations, so the language we use and our presence of mind have a huge impact.

When we approach this conversation, we should be prepared to discuss:

1. The issue that needs to be resolved, including the fact that it remains unaddressed or poorly handled even after previous conversations

For example: “We’ve talked about you missing deadlines without warning a couple of times over the last two weeks, and even though we talked through ways for you to fix it, you missed another one this week without letting me know. I’d like to understand why and talk through what needs to change so it doesn’t happen again.”

2. What we specifically expect to see change

For example: “Going forward, you need to implement the changes we discussed before, namely that you’ll ‘raise a flag’ early to let the team know if something looks like it will slip and why.”

3. When that change needs to be in place, and the expectation that it isn’t just a one-time change

For example: “I expect this to be how we work together from this point forward, so we don’t see any more surprises.”

4. What will happen if it occurs again (which may lead to the next section)

For example: “I know you have the skills and drive to make the changes needed, and I’m here 100% to support you. My aim is that we won’t need to have this conversation again. But if we do, you need to understand that our next conversation will have serious implications for your career here.”

Two people often walk away from the same conversation with different memories of what was discussed (or what was important), especially when emotions are involved. So take the time to send an email summary of what you discussed, laying out the situation, the feedback delivered, and the proposed remedies. This can eliminate ambiguity and provide the employee with the opportunity to highlight any gaps or disagreements. It also highlights the importance of the conversation.

Photo courtesy of WOCinTechChat

Sometimes people continue to miss expectations and it looks like we’ve hit the end of the road. Once we, as humans, have made up our mind that someone isn’t performing, it can be hard to see that they may ever be able to fix it. Frustration and apathy can kick in at this, the worst possible time.

Distance compounds that impression so your boss, being a step removed, has less of an opportunity to see the potential for improvement; the same is true for Human Resources (HR). So, while you’re likely already stressed about how to handle the situation, they may be telling you to “make the call,” “rip off the bandaid,” and “get it over with.”

In an experienced organization, there will be an established process to follow to ensure that everything is documented and the company is covered.

In some companies, that process is simply a checklist with a 100% chance the employee will be fired. But in a good organization, it provides a real (and final) opportunity for the team member to improve their performance and avoid being let go.

Either way, it’s up to us to do right and treat this step as a last chance for meaningful change. We owe it to the human whose livelihood, identity, and self-confidence is on the line.

There are different formats for a PIP (Performance Improvement Plan), but at the heart of it, it’s a formalized version of the steps I laid out above, often treated as an actual contract with signatures to verify that the employee has seen the plan, even if they don’t agree with it. You’ll work with HR to build a plan ahead of meeting with the employee, the key aspects of which are:

  1. Where the employee is underperforming and what constitutes expected performance
  2. What exactly needs to change
  3. Specific, measurable objectives that show progress
  4. A timeline for when changes will be in place and the length of the program, which will be tied to the amount of time required to observe results. It should also include a schedule for how often you will meet to review progress.
  5. A clear statement that the employee owns with listed goals and requests for any support they will need from the manager or company
  6. The consequences of not meeting the objectives

While it’s hard to implement a PIP as a manager, it will be harder for the recipient. It’s tempting to soften the blow but that risks muddying the importance of the situation. Be clear and reinforce that you are there to help, but it is on them to succeed.

This process requires a true investment of time and energy on both of your parts. You must be truly invested in their pulling through and proving themselves. Anything less is a failure. They must also be interested in making the needed changes, with the goal of staying on the team.

Making a decision

At the end of the program, there are two options: Either the team member still isn’t meeting expectations, or they have improved to the needed level. There should be no middle ground. Extending the plan for someone who isn’t quite meeting the stated goals is avoidance.

Even with all of your effort, and perhaps good faith on the part of the employee, you may find that their performance still isn’t at the level where you need it to be. If you laid out your plan well and communicated clearly throughout, then it should be clear to all involved that it’s time for the employee to move on to another company. Be clear and kind when you have this conversation. If they tried, thank them for their effort, and ease the transition out as best you can.

It’s exciting when all of your hard work has paid off and you can see someone reach the potential you know they have. Congratulate and thank them for their effort — it was a lot! Then be sure to clearly communicate that everything is not going to return to how it was — this is the new normal.

Wrapping up

Take the time to think through how you give feedback and when. Don’t let it simmer and don’t weaken it by trying to be nice. Provide as much support as you can without taking ownership of the employee’s responsibility for their behavior.

Doing this will help them grow and in time, you will earn their trust as you show that you truly care about them as an individual.

Isn’t that what we all want?


Helping designers thrive.

Alex Jones

Written by

Leading at the intersection of strategy & design. Autodidact. Barbecue acolyte. I start fires (the good kind).


Helping designers thrive. A Medium publication about UX/UI design.

Alex Jones

Written by

Leading at the intersection of strategy & design. Autodidact. Barbecue acolyte. I start fires (the good kind).


Helping designers thrive. A Medium publication about UX/UI design.

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