Issue No. 02 | How To Coach An Underperforming Employee
Do you have someone on your team who just isn’t hitting the mark? Like they’re just not getting it?
Maybe they’re missing deadlines, delivering subpar work, or just seem disengaged.
There are many — maaany — reasons why you might have an employee who’s not cutting it, but far fewer ways to deal with it effectively. Learning how to coach an underperforming employee is one of the most valuable skills you can develop as a leader or business owner.
I hate to break it to you, but you are going to have to address it head-on with them and this means…dun, dun, dun…having a difficult conversation! Gasp!
Whatever the reason, the idea of sitting down to address it probably gives you mild anxiety. Nobody loves these talks, right? And how the hell do you even start?!
It is very common to try and avoid these conversations or delay the inevitable, because they are, well…difficult. They can be difficult for you to deliver, and they can be difficult for your team member to hear.
But if we switch our thinking from “this is a difficult conversation” to “this is an important one” — one that ultimately benefits your team member — it can have a far more positive impact on the experience and outcome for both of you.
It also helps to understand that the intent of these meetings and addressing any performance issues is not to reprimand, punish, or rub their nose in their mistakes, it’s to work with them to identify the root cause, find a solution, and support them while they get back in fighting shape.
It’s a process that, when done right, can actually improve performance.
And that’s what we want. Coaching your team members is a big piece of the leadership puzzle and addressing under performance is significant to the success of your team members.
If you want a deep dive into having difficult conversations, read How to Approach Difficult Conversations.
This post is beefy and covers a lot, but if you’re looking for the TL;DR – skip down to the bottom for the key take aways
Step One | Getting Started
One of the hardest parts of having a difficult conversation can be just getting started. It’s not unusual to get really hung up on finding the exact magical combinations of words to start the conversation.
This is usually where we try to soften the blow with unnecessary small talk or pleasantries. And what people don’t realize is this usually makes it worse…particularly for the person receiving the less-than-pleasant feedback. They typically know something is up and the longer you delay it, the longer they’re sitting there waiting for the other shoe to drop.
The best way to start the conversation is to address the elephant in the room right out the gate, and let them know you are here to have a difficult conversation.
If you’re wondering how to coach an underperforming employee without sounding harsh, this is where it starts — by being honest, clear, and compassionate from the get-go.
This may sound like…
“I need to discuss something with you that may be a little hard to talk about, but it’s important that we discuss it and find a solution”
“This might be a hard conversation for us to have, but we need to discuss [insert specific issue]”
Step Two | Let’s Get to the Root of the Issue
Before you can work on resolving anything or coaching your employee through the issue, you need to know what’s actually happening. You simply cannot fix a problem if you don’t know what’s causing it.
There are a number of factors that can contribute to an underperforming team member. Anything from personal problems and burnout to lack of training or tools/resources. And they can present in a number of different ways, like delays in handing in work, disengagement, attitude problems, and missing work all together.
Addressing the concern is half the battle, but working to find the right solution to the right problem is the other.
And now you may be wondering “Well how do we know what the root cause is?”
Well, my friends…we’re going to ask them.
This may sound like…
“I’ve noticed [insert specific issue] recently—can you tell me what’s been going on?”
“I’ve noticed [insert specific issue] happened again today. I want to talk about what’s been going on and see if we can come up with a solution”.
Step Three | Have an Open and Honest (but Direct) Conversation
It is so, sooo important to be direct when you are addressing any issues related to performance. It doesn’t benefit anyone — not you, not your team member, and not your business — to be vague, overly soft, or cushion the conversation in compliments or small talk.
You absolutely want to be kind and mindful of your tone (you’re not coming guns a blazing here), but it is imperative you are direct with your language and very clear about what the issue is, how it’s affecting the team or business, and why it’s an issue. It’s also important to focus on the behaviour or action and not make it about them as a person.
It can’t be stressed enough the intent of this initial conversation is to really understand what’s going on. You will use those stellar active listening skills you have to hear their perspective and get to the root cause. You are not listening to blame, punish, or voice your frustrations. You are there to create a space where the person feels comfortable opening up about what’s going on so you can work together to find a solution.
Step Four | Set Clear Expectations
Clarity at this point is crucial. It 👏🏻is👏🏻 crucial👏🏻
You must clearly define how they’re underperforming, why it’s an issue, the impact it has, and what needs to happen moving forward. If you want to see improvement, expectations and next steps must be made crystal clear.
When you set clear expectations, you eliminate confusion or any grey area and provide a clear, direct path forward. Without clarity, they may not understand what they need to do to improve — and may continue to underperform. I mean, how many times have you walked out of a meeting not entirely sure what you are supposed to do?
Use the SMART goal method if appropriate and pull in any supporting documents you may have (policies, procedures, training manuals, etc.).
Having the how, why, and what clearly established will not only highlight what needs to happen to improve but will also help with identifying what support is needed and establish accountability for the team member.
For best results, follow up this conversation with an email outlining the action items for both of you
This may sound like…
“For the next two weeks, the priority is [insert priority]. Other tasks can wait unless they’re urgent. Focus your energy on these tasks, and we’ll reassess in one week.”
“I’ve noticed there’s been some confusion around priorities, so to be clear, your top focus this week is completing [specific task]. Once that’s wrapped up, we can shift focus to [next task].”
Step Five | Offer Support and Resources
Once you’ve clearly established what needs to happen to improve and set your expectations moving forward, the next step in coaching an underperforming employee — whether you’re a new manager or a business owner — is figuring out what support is needed.
Remember — the intent of these meetings isn’t to punish or reprimand; it’s to help your team member get back on track.
Support can look different depending on the situation. If someone is struggling with a personal or health issue, support might mean giving them time off or temporarily adjusting their schedule.
In other cases, it might mean extra coaching, training, or access to better tools and resources. The key is to identify what will help this specific team member succeed.
When you offer support, keep it time-bound. If you agree to additional training, time off, or an adjusted workload, attach a clear timeline and follow-up date to re-evaluate the situation.
This may sound like…
“I want to make sure you have everything you need to succeed. If there are any tools, training, or resources that could help, let me know and I’ll make them available to you.”
“Let’s set up a weekly check-in to go over your progress and discuss any challenges you’re facing. That way, we can address things early and adjust as needed.”
Step Six | Document, Follow Up, and Give Regular Feedback
When you are dealing with performance issues, it is almost never a one and done scenario. Meaning you are looking at having at least a couple of meetings to discuss the issue, check-in on how they are doing, highlight any improvements they’re making, and re-evaluate the support and resources as you go along.
As with any coaching conversation, take notes. Document what was discussed, what support and action items were agreed upon, and what next steps or timelines you’ve set.
You don’t need a formal “action plan” — even a quick email summary works wonders for keeping everyone aligned and accountable.
This may look like…
“Thanks for meeting today. To recap, your main focus over the next two weeks is [priority]. We’ll touch base next Friday to see how things are going. You agreed to look into [training/resource], and I’ll [manager action]. Please let me know if anything else comes up.”
Step Seven | Be Patient, But Honest About Consequences
It is important that you are very upfront about the consequences, whether this means continued performance issues can affect their team, their position, their chances of a raise or bonus, their client relationships — or, in the worst-case scenario, lead to termination.
This may sound like…
“If we can’t meet the [specific task] by the Friday deadline, it’ll delay the entire project and potentially impact the client relationship. It’s really important we stay on track with this timeline.”
“If your performance doesn’t improve by X date, it may affect your eligibility for future projects or promotions. I want to help you succeed, but we need to see consistent improvement in these areas.”
A Note on Terminations
To make sure you set the right tone and make sure the employee feels supported, I strongly suggest you do not bring up termination in the initial meetings or even go in with that as an end-goal. It’s not exactly what I would call an effective motivator.
I have worked with many managers in the past who have just gone through the motions of crossing their t’s and dotted their i’s, so in the end they can just terminate the employee for cause or with a ‘clean conscience’ and I will say, most employees see right through this strategy.
While there are times when, after a genuine attempt to improve performance from both sides, it still doesn’t work out and ultimately ends in termination.
But termination is a whole other blog post.
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I know coaching an employee through performance issues can seem like one of the harder, more frustrating parts of our role as a leader, but it can also be one of the more rewarding. By taking the time to understand the situation and work with your team member to improve their performance, you’re investing in their success, your team’s success, and your own skills as a leader.
As you grow into your role as a business owner and team leader, these coaching moments will become second nature—and you’ll be the one your team turns to when they’re struggling and need support. So, the next time you face an underperforming employee, don’t shy away from the conversation.
Remember, learning how to coach an underperforming employee is part of growing into your leadership role — and it’s one of the most valuable skills a business owner can master.
Key Takeaways
✓ Start the conversation by acknowledging this may be a difficult conversation
✓ Go into the conversation with the intent to bring the issue to light, find out the root cause, offer support if needed, and find a solution.
✓ Be specific and direct with what the actual issue is, how it’s affecting the team, and why it’s an issue.
✓ Set clear expectations of what needs to happen moving forward to improve performance
✓ Offer support and ensure your team member knows you are there to help them succeed
✓ Take notes!
✓ Follow up with any action items, agreed support plans, and any check-in meetings
✓ Avoid talking about terminations in the initial meetings.