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Answering Your Questions about Having Difficult Conversations 

I recently sent out a survey to folks on our mailing list asking what issues they were facing and what they wanted me to talk about in future episodes. So today, I’m going to dive into one of those questions. If you’ve been wondering how to have those difficult conversations with team members who aren’t meeting expectations, keep reading.

I sent out a survey to the folks on our mailing list because I want this podcast to be as useful to you as possible. And to do that, I need to know what you need to know. If are not on our mailing list and you have questions about supervising or want to suggest a topic, you can find the link to take the survey in the episode summary.

One of the questions I asked folks was, “If you had a coaching session with one of us, what situation or problem would you want to break down and get guidance on?” The very first person to answer the survey asked…

“How do I handle difficult conversations with staff members? For example, I have an employee who has trouble following directions. Sometimes they change what they were asked to do or how they were asked to do it. The employee gives me all sorts of excuses each time they’re late or slips out early. They don’t seem to understand written directions and verbal instructions must be repeated multiple times. I don’t know how to better communicate with someone who seems to have a learning disability.”

What a great question to start us off! Now this staff member seems to have a few things going on, but in general, this is a pretty typical problem, right? A team member isn’t living up to your expectations and thus, you need to have a conversation about their performance. And it’s especially frustrating when you feel like you’ve tried oh-so many things to help them be successful.

If we break down this question, there are really two parts to this question. First, how do you “fix” an employee who seems to have ongoing issues? And second, how do you make such conversations less difficult?

I’m going to start with the second part of this equation first. Now, since I’m the one who wrote this article, you may be wondering, “Then why the BLEEP didn’t you just say that WAS the first part?” Good question. Lol. I chose to put them in that order because most folks would say the primary issue is the employee’s issues. I mean, if they just did what they were supposed to do, you wouldn’t have to have a conversation at all, right?

Well in part, these conversations seem so heavy because we typically only discuss people’s performance when there are problems. If someone’s nailing it, or at least doing decent work, then things move along pretty smoothly. When things are seemingly going well, there’s not much motivation for you to stop and discuss performance. But when someone is getting in the way of your team’s success, suddenly that motivation is there even if it feels difficult.

But what if you discussed performance on a regular basis, even with the folks who are meeting expectations? I know some of you meet with your team regularly. And I know some of you mean to, but all the stuff on your plate and the fire putting out get in the way. But having regular coaching conversations with your team is key to their and your success. If you’re meeting with your team members every week or every other week to discuss not just what they’re doing but HOW they’re doing, it will make it way easier for you and THEM to have a discussion when things need to improve.

Question…has your boss ever sent you a short email or popped their head in to say, “Hey, I need to talk to you today before you leave.” Now even if you’re the bestest employee ever, what are you going to do? You’re going to sit there and wonder what this is about and what you might have done wrong. You’re going to stop being productive and instead hyperfocus on what could be wrong. Again, that’s because we’ve been taught that unexpected talks with the boss are an unusual, stressful thing. It’s perceived as being negative.

Even if you meet with your folks regularly, if you don’t often discuss performance other than an occasional “great job on ______,” any discussion about things that need to be improved is going to make folks feel stressed out and defensive. And naturally, that’s how you’re going to feel about the situation as well. The system that most of us use is primed to make everyone involved go into a stress response. And if you’ve read any of my past articles on stress, you know being in a stress response will negatively impact how both parties navigate these situations. You’re going to be all in your head, and they’re going to be worried and defensive.

The first thing you need to do to make these difficult conversations less difficult is to set up a new system to manage your team’s performance. That means regular meetings with each team member that focus on both performance and professional development. And that’s a change from what most one on one meetings look like. I meet with plenty of folks who say when their supervisor does meet with them, it goes something like this…

“How are things going? What do you need from me? I need you to work on this new project. (Where you only get a broad overview.) Any questions? Okay, let me know if you need anything.”

Now obviously most meetings go longer than this, but in general they’re not structured in a meaningful way. Yes, your supervisor may give you the opportunity to ask questions or bring up issues. But depending on your relationship with your supervisor, you may not feel comfortable asking the questions you really need answered. You may not want your supervisor to question your abilities, so you decide you’ll figure things out yourself. Or you just may not want to let them down.

So, what SHOULD these meetings look like? To answer that question, we’re going to switch gears a bit and dive into that first issue about how to address an employee who’s not living up to your expectations, aka – performance management.

Now I want to preface this by saying you cannot “fix” an employee’s behavior or performance without their consent. What I mean by that is you may have the best intentions and do everything within your power to support and coach them to success, BUT if they lack the desire or ability to upgrade their performance, there’s nothing you can do to change that. You trying harder is not the solution. It’s just going to make you – and possibly your team – frustrated and waste valuable energy.

At its core, performance management consists of three main components…

  • Setting CLEAR Expectations

  • Consistent Coaching

  • Holding Folks Accountable

I’ve done several articles on each of these things, but I want to briefly break them down here. Collectively, I’d like to frame this with a Brené Brown quote. She says, “Clear is kind. Unclear is unkind.” If you’re wrestling with issues like these, it’s most likely because you WANT to be kind and supportive of your team. And that’s wonderful. But the best way you can do that is to be clear and direct with your team. Keeping this in mind, let’s dive into these components.


You need to be clear about what you expect from your team. Yes, they have a job description, but that’s a broad overview. Plus, it can change over time or even daily. The very first element in Gallup’s engagement tool, the Q12, is “I know what’s expected of me at work.” Knowing what’s expected is foundational for anyone’s success. You can do this verbally, but it’s also helpful to put these things in writing. Everyone is busy, including you. I don’t know about you, but I definitely don’t remember everything I tell folks. And sometimes I think I’ve told Alicia something, and she assures me I definitely did not. Thus, it is helpful to have things in an email or shared document. This keeps everyone on the same page and makes it easy for either party to verify what has been communicated.

But before all of that, YOU need to take the time to become clear on what you expect. Most supervisors don’t take the time to do this, which means they can’t communicate to their team members what they need them to do. In all fairness, you probably don’t do this because A) you’re crazy busy, and B) most of us assume other people know we want. But there’s no reason for that to be true. You cannot assume they know. And don’t fall into the trap of believing, “they SHOULD know.”

Maybe they should, but it’s your job to make sure they do. YOU need to make sure they know what’s expected of them. And until you’re clearly communicating what you need them to do and what the final results need to look like, you’re setting up your team to fail. And just asking them, “do you have any questions?” doesn’t fix the problem. Remember, that less-than-optimal supervisor interaction I mentioned earlier. I once had a statistics professor who always asked, “What questions do you have?” I never asked any because I was so confused, I had ALL the questions! But I didn’t want to say, “Yes, I have a question. Can you explain all of that again?” Never assume you’re on the same page until you’ve discussed it.


Once you clearly lay out your expectations, then you need to coach your team along the way. These sessions need to happen regularly. They also need to be structured so both you and your team members know what’s going to be covered. Now I have Adaptability, so for a long time I felt like a meeting agenda kept me from going with the flow of the conversation. But really, it sets up expectations for what’s to come. It also makes sure you remember what you want to talk about. We’re often so rushed; we mean to cover certain things but simply forget because we’re running late from our last meeting.

And remember, we’re restructuring this process so difficult conversations don’t feel so difficult. That means talking about performance EVERY TIME. You can add in other topics as well, but at the very least you need to talk about any current or new expectations. Then you need to discuss what they’re working on. Don’t just ask, “How’s ____ going?” Ask specific questions. The purpose of this is NOT to micromanage. Micromanaging is about maintaining control. You’re asking questions to assess where they are in the project and to get in front of any potential issues.

Often the folks we have issues with will answer the, “How’s it going?” question with “fine” or “everything is good.” But that doesn’t tell you anything and doesn’t allow you to correct their course along the way. You need to know what’s going well and why, so you can reinforce it. You need to know what’s potentially getting in their way and why, so you can help them problem solve. Your job as coach is to help support them as they try to meet the expectations you’ve laid out. This is your opportunity to do that.


This part is what stresses out so many folks. I’m sure that’s why this person asked the question. But if you’re being clear upfront, including putting those expectations in writing somewhere, and coaching folks along the way, then this part is easy – even if it doesn’t feel great. But remember, if you don’t have clear expectations set in the beginning, that’s when this gets really messy.

First, accountability is NOT about failure. If someone lives up to your expectations, then you should hold them accountable by celebrating their success. Another element of Gallup’s Q12 is “In the last seven days, I’ve received recognition or praise for doing good work.” But even successful team members don’t necessarily maximize their energy, so this is also the time to focus on development. Use this opportunity to talk about how they can improve their performance in the future or how the experience can help them in their career.

One of the best tools to use to maximize these conversations is CliftonStrengths. If you and your team know your Talent Themes, then when you’re in this accountability phase you can ask folks, “How do you think your talents help you succeed with this project?” That answer can help top performers lean into the things they do best. You can also ask, “How do you think your talents might have gotten in your way?” This works for top performers as well as folks you’re having problems with, because our talents can easily get in our way even if we’re ultimately successful. Imagine if that high performer could use 25% less effort to achieve the same goal? That’s just as important as focusing your time on correcting under performers.

Now, I explained this in terms of top performers because we tend to have a more positive attitude about interacting with those folks. But the concept is the same for folks who aren’t meeting your expectations. Since you’ve been clear along the way and it’s in writing, if anyone goes into the whole, “but I didn’t understand what you meant?” or, “that’s not what you said I needed to do” business, you can easily set it aside. If they bring it up, you simply remind them that, “I’ve been very clear this entire time and we’ve had several conversations before now to clarify what was expected.” Again, if you aren’t clear upfront and they go this direction, they may have a good point.

This is also where you need to be clear about what needs to change and the potential consequences if they don’t improve. I’m sure you have an official HR discipline process. They need to know what it is and what changes they need to make to keep their job. Again, clear is kind. It may feel icky, but finding softer words causes confusion. It may feel like saying, “We’re going to have to look at other options if things don’t change,” is a gentle way of letting folks know they’re going to lose their job. But that can be misinterpreted as, “Oh if I don’t make this change, maybe they’ll move me to another job or change my responsibilities.” You need to communicate that they need to do A, B, and C by _____ or _____ will happen. That doesn’t mean you can’t support them as they do that. But ultimately, it’s on them to make the changes happen by the deadline.


Okay, so those are the three main components of performance management. But I do want to take a few minutes to address the last thing this supervisor mentioned in their question. And that’s about how they suspect the individual in question has a learning disability.

Alicia used to be the Assistant Director of Academic Support, which included overseeing the Disability Support Program. So, we’d often discuss these issues, including how the guidelines apply to staff as well as students. In a nutshell, for someone to receive reasonable accommodations, they need to disclose a diagnosis that makes them eligible for reasonable accommodations at work. That means you must treat folks like you would anyone else on your team, until they tell you otherwise.

And even if someone DOES have a diagnosis that MAY be eligible for accommodations, it doesn’t mean they automatically get them. There is no magic list that tells you exactly what those accommodations should be. This is a discussion between the employer and employee to determine what REASONABLE ACCOMMODATIONS make sense in that situation. Typically, HR is involved in these discussions to make things official.

And the qualifier “reasonable” is very important here. In this example, the employee often comes in late and offers various excuses. Well, let’s say they go to the supervisor and say they’ve just been diagnosed with ADHD, so they need to have a flexible start time. You may think that seems reasonable given the diagnosis, BUT you also need to factor in the expectations of the position. If their responsibilities include opening the gym at 8AM every day, it is NOT reasonable for them to have a flexible start time. That would mean everyone would have to wait until they showed up to get into the gym, which simply doesn’t work. Other positions may allow for that flexibility, but it’s a discussion not a given. And yes, that may very well mean they cannot continue doing this job if they can’t meet those expectations. That’s not necessarily a failure on anyone’s part, but rather the job isn’t a good fit for that person.  

In the original question, the supervisor is assuming there’s a learning disability in play. While that may be true, you’re not allowed to suggest that to the individual or treat them any differently than you do everyone else. If you do, you may very well run into trouble if you do need to terminate that person. Not to mention, how fair is it to the rest of your team that this individual gets all this extra “help” and isn’t held to the same standards as other folks who ARE meeting the expectations of their roles? That can negatively impact your team’s engagement.

What you can do is let ALL of your team members know what resources are available to them. And when you’re coaching everyone, come at it with curiosity. Again, you’re not trying to diagnose your team. You’re asking them questions to help THEM identify what’s preventing them from being successful. Maybe that’s something you can address, but it might also be something they need to fix on their end. You’re also asking them questions to identify what could help make their performance even better. Do that consistently with all your team members and you’ll be able to address potential issues along the way. That’s a less stressful approach for everyone vs. letting things build into a huge, uncomfortable conversation. And as an added bonus, this process also allows you to focus on your team’s development and engagement at the same time. That’s a win-win-win.

Okay, I hope this has given you an overview of how to make those difficult conversations less stressful for you and your team members. Again, I’ve done previous articles that dive into different aspects of performance management, so you can go back and dig in deeper. Or, we’d love to work with you through individual coaching or in a group workshop to help you upgrade your performance management skills and get even more tools to make managing your team less stressful and more impactful. You can reach out to me at to ask questions and get more information about the services we have at Strengths University.

And, if you have a question or topic you’d like to suggest for future articles, you can use this link to fill in our survey -





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