Ep. #13: Managing Your Most Difficult Employee (even in times of crisis)

Hello, everyone. Welcome to episode number 13. I am so excited to be here with you today. No, really, I am. At the time of recording this episode, I have been working from home, my children have been home for a full week now, all because of the coronavirus. We are still in the very beginning stages. We don't know what to expect, and it's just a very uncertain time for everybody.

So to get us started, I want to give a shoutout to my clients right now, who are just really killing it. So if you're a client of mine, you're probably a very high achiever, so when, pardon my French, shit hits the fan, you step up to the plate. So if that sounds like you, you're in the right place.

But I also want to acknowledge that, during this uncertain time, it's also possible that you're feeling a bit of imposter syndrome. But let me just point out for a minute what that might look like for you. So let's say you're willing to just dive in headfirst, you want to step up to the plate, you want to show your boss that you're capable of handling more and now's your big opportunity, and you're leading a team, so you put together this email for your team, and you're going to rally the troops and let them know that everything is okay, and exactly what the vision is for your team, and you hear crickets. Nothing; no one responds and nobody says thank you and nobody pats you on the back. And so you start to feel a bit insecure. You wonder, "Oh, maybe I shouldn't have sent that email. Maybe I shouldn't have come up with that vision in that way," and you start to pull back.

But the thing that I want to remind you of is that even senior leaders also experience imposter syndrome. But the thing that makes a really exceptional leader stand out above the rest is that, even though they experience doubt, even though they're going through uncertainty and they don't have all the answers, the important thing is is that they show up and they do it anyway. They know that their role is a leader and that they have to be there for their team. It's the most important thing, that their team sees them in this way. And I'm not talking about that you have to be strong and you have to put on this face. Actually, I'm talking about just the opposite. If, at any time, it was important to be vulnerable in front of your team, now is that chance. It's a chance for you to show them, "Hey, I'm scared too. Hey, I've never worked from home with my kids hanging out in the other room. Hey, I'm not sure that we have enough food to cover us for the next three weeks as we're staying inside our homes. Hey, I don't know what's going to happen next with the organization. But I want you to know that I am here to lead you, that I am here to guide you."

And the ways that you can do that, and the way that you can be there for your team, is to just really understand what are the three most important things that your team needs from you right now? Number one, empathy compassion. They need to see that you're a real human being. Number two, they need face time with you. So I'm hearing all over the place that people are having daily huddles. They go from weekly meetings with their team to daily meetings with their team. It's even more important right now that you're showing up, that you're there for them, that you're reaching out to each one of them individually, and giving them as much face time as possible. And number three, they need strategy and vision. So it's not enough to just tell them what to do. You also have to tell them what the expectations are. What does success look like for your team? Because success may not look the same way that it used to.

For instance, I have a client that works in sales. And her success for her team was always measured on very specific results on, literally, how much money comes in. So they're not going to be able to measure whether or not their results are working in the same way that they used to be able to, because it's not a money game right now. But instead, she can show them, "Okay. What we're going to be doing, our strategy for the next two or three months is going to be all about building relationships." And then she has to give them the exact strategy of what that's going to look like. And what does success look like? So I'm just telling you that, and offering you that, so that you can keep in mind, what do people need from you? And, actually, I said this goes for your team, but it also goes for managing up. What does your boss need from you? What does the CEO need from you? Empathy, compassion, face time with you, they need to be able to see you way more regularly than before, And they need to understand what your strategy and your plan is. And if you do those three things, essentially you're setting yourself up for a promotion.

Now. This brings me to my second point that I want to point out right now because I know it may feel like this is the last time, or the worst time in your career to actually go for a promotion. But I want to point out that a promotion happens in many, many, many different ways. It could happen because you're given a higher level of responsibility. It could happen because now, all of a sudden, you have a seat at the table, or it could actually mean that you get a higher position. You get a salary increase, you get a different title. In 2008, the percentage of women who were promoted into higher-level leadership positions was at an all-time high. In the heart of the financial crisis, 2008, more women were promoted into leadership positions. And the reason is because we needed compassion at the top. We needed that strong leadership. We needed a different voice. So if you're that type of leader, if you are a leader of the people, if you are a leader that understands and can see the bigger vision, then we need you now more than ever.

So in today's episode, I'm going to be talking about how to manage your most difficult employees. Now, I know it may feel like this is not necessarily the time to come down hard on those difficult people that you work with, and it may seem like, "Oh, let's just let them slide." But I actually think it's just the opposite. I think that if you had a difficult relationship with one of your employees, it's only going to get worse during this time of uncertainty. And your instinct might be to pull away. It might be to just give them space. And I'm going to encourage you to actually lean in and do something different with this employee. To actually use this as an opportunity to work with that difficult employee and to empathize with them, and to actually strategize with them in a different way to actually see if you can produce a different outcome.

So this is going to require you to really step up to the plate. It's going to require a different level of leadership but don't worry. I know you're up for the challenge and who knows. You could get that person who's always been wrenching your plans. I was going to say a ring in your neck. Something like that. But that employee that has always been just so difficult to work with and doesn't meet their deadlines, doesn't listen to you, brings down the morale of the team. This could be the opportunity to actually get them to step up to the plate as well. We all want to be seen, we all want to be heard, and in a time of crisis we want our work to matter even more.

So to start out with I just want to point out that one of the reasons that you might not have been able to get promoted in the past could be because you haven't been able to deal with this difficult employee properly. Now what I mean by this is, imagine that you have a difficult employee and your boss knows that you have a difficult employee, and you do one of two things. So you either complain to your boss about said difficult employee. So you'll talk to your boss about the reason that you missed the deadlines or your team missed the deadlines is because such and such didn't deliver on time. Or such and such seems to be behind on the game. So you'll use this person as an excuse and you'll use this person as a problem as to why you aren't able to get the results that you want. And sometimes we even put it into our boss's hands to fix the problem.

Now let's say that you do the opposite. So you choose choice number two which is that you don't share it with your boss. So you're kind of embarrassed. You're like I need to just handle this myself. I need to figure it out. I need to do something about it. So you never tell your boss what's going on. Let me tell you. Your boss knows what's going on. So either way, your boss knows so it doesn't matter if you're doing step number one where you're blaming your challenges on this difficult employee or step number two which is that you're trying to hide it from your boss and just sweep it under the rug and deal with it on your own. Either way, your boss knows that you're not properly handling this situation. Now imagine if they gave you a promotion. Now you have an even bigger team or you're managing managers which is a whole different ball game. How are they going to trust you to be able to do that?

So what your leader needs to know is that you can handle difficult employees. So I'm going to give you three ways that you can actually work with this person and even during this time of uncertainty you can still apply these and actually I think it might actually be easier to apply these steps that I have used with my clients and I know it really makes such a huge impact and people are just shocked at how quickly it works. They'll have a difficult employee for years and years and years and then all of a sudden they do what I'm going to teach you today and it just turns every single thing around.

So I'm going to give you the three steps now but I just wanted to point out that all of this leads into how you're going to have more success in your career and how you're going to be able to be seen in a better light. Now, before I get into showing you how to manage a difficult employee, I want to first define what a difficult employee is or could be for you so that we're all on the same page.

In the book, The No-Asshole Rule, by Stanford professor Robert Sutton, he talks about the difference between a temporary asshole, who might be having a bad moment or a bad day, and a certified asshole, who is persistently nasty. He gives the example of when he sent a scornful email to a colleague because he wrongly believed she was trying to take an office away from his group. In this instant, he was acting like a temporary asshole, and to be a certified asshole he would have to act like that jerk persistently. So first of all, I just want you to notice this difference.

So you might think that you have a persistent asshole on your hands, somebody who just needs to be dealt with or that they're just like this and they're not changeable, but it's also possible that that person is actually just a temporary asshole [laughter], meaning that they're just in the wrong role or they don't understand the expectations, or maybe they had a poor leader in the past who just didn't clearly define what it is that they needed. So these three steps that I'm going to show you are meant for you to uncover that, to really be able to decide for yourself, "Okay, is this person manageable? Is this person workable?" Because having a persistent asshole on your team is toxic. It's toxic to everybody, and you may notice that it brings down morale of the team. That's probably something that you've already witnessed yourself, but it also is a timesuck for you.

You're spending so much time trying to manage this difficult employee that you're not able to create the strategy and the vision for your team that they so desperately need. Your team wants you to actually take control of the situation, even if they empathize with this difficult employee. Even if it seems like they'll be upset or there'll be backlash because of this difficult employee and when you work with his difficult employee. I'm not actually advocating here firing somebody or getting rid of somebody. I'm actually-- the steps that I'm giving you are to uncover if that person is, first, manageable.

So the secondary step is what you're actually going to do about it, but the first thing is really just, how can I work with this employee? How can I see if this person is actually manageable?

So step number one: acknowledge any challenges that that person may be facing. If it's a team member that you didn't hire, you could let them know that this is the way things were done in the past, it' snot their fault, they just don't know any better. And I also encourage you to reinforce what they're doing well. So this is kind of how it applies in this time of crisis and uncertainty: acknowledge the challenges that we're all facing. Be empathetic. Let them-- what you're wanting to do is you're wanting to reduce their fight or flight instinct, so you're wanting to break down their guard. And I don't mean to lie to them. Actually find something that you do-- that is truly not their fault. Like I said, if they were hired by somebody else, if they had poor leadership in the past, if there were not clear expectations, this is not actually their fault.

And so you're just sort of saying it up front, and so that way, maybe, they'll let their guard down a little bit, and they'll actually tell you what their real challenges are. Another thing to notice is that that many difficult employees have been with the company for a long time. So they feel like they have tenure. They've been there 20 years. They're an expert at what they do. So another thing that you can get through to them, is that you have an expectation for them to show up as a leader.

And then you can define for them what leadership looks like. So it's not being rewarded for your expertise, it's being rewarded for your relationships, your communication, working well with others, all of these soft skills that maybe they didn't have the expectation of before. And so if they understand your point of view, and they understand what you're trying to do for them, then they can either say, oh, I'm not interested in that. I'm not interested in a leadership role.

So then now you know where they're coming from. Or they might say, oh, I didn't realize that. This is just the way it's always been done. And the unintentional side effect of first acknowledging their challenges, that a difficult employee might be facing is that you learn something about why their behavior is so challenging.

Not as their typical excuses, but it gives you actual clues. You may not even know what they were told directly by their previous boss that led to them acting so weird. So be open to being surprised. Be humbled. Now, let's move onto step number two of managing difficult relationships. It's to be clear and be direct.

Now, when I talk about directness, I don't mean changing your leadership style so that you can work with a person. I mean saying exactly what you need. Giving them a very specific deadline. Letting them know what success looks like. What your expectation is. Back to step number one, if you're speaking to them because you want them to be your successor someday. Usually, we don't pick our difficult employee to be our successor, but sometimes we get stuck with a difficult employee that's our only option. So let them know, why are you grooming them in this way. You're not just doing it because you want to fix them.

See, that's when the fight or flight comes in, is when they feel on-guard. When they feel like you're trying to fix them and change them, then they're going to put up their defenses. And that's what you want to try and avoid. So another thing that ends up being a possibility that I hear a lot from people, is that I've already told them once, twice, three times, and they just don't get it.

But let's be humble here for a minute. Let's say, if you've told someone once, twice, three times, four times, five times, and they just don't get it but you're doing it the exact same way, let's say that perhaps, just perhaps, maybe the way that you're speaking with them is not working. So do it again. But I want to encourage you to do it differently. So if you've been direct in the past in a certain way, figure out another way to connect with them and be direct. Give yourself two or three tries, try many different angles before you just give up on the person. And like I said, any of this can be done even if it's a time of uncertainty. Even if your employees are working remotely. Even if something different is happening in the organization, you can be direct with them. You can set expectations. It's not unkind. This is not a time to just let people slide and get off the hook. You can be an empathetic leader. I know you. You are compassionate. You are empathetic. You can be that rock for them and you can also be direct.

Direct doesn't mean that you're a jerk, especially if you do the first step and you actually acknowledge why, perhaps, it-- they have this certain type of behavior. So if you do the first step, then you won't come off as a jerk. You won't come off as too direct or you won't have to alter your personal leadership style. And then, step number three is to set them up for success and this is so important.

So many leaders, they try to look to the future when they're dealing with a difficult employee and they say, "Well, I don't want to have to keep micromanaging them, so I don't want to micromanage them now. So I'm just going to tell them one more time that they need to get this to me." No. No, tell them that they need to get this to you and then check up on them, and check up on them again, and see how they're doing, and maybe sit down with them and actually walk them through it. Spend a little bit more time with them to actually set them up for success. Work with them a little bit more than you would with your other employees. I'm telling you, if you put in the legwork now, it will solve you-- or save you so many headaches further down the line. So just really think about it, "How can I go above and beyond right now to eliminate and open up time in the future?" So be willing to do that. Be willing to sit down with them.

We're in a time, like I said, where people are having daily huddles instead of weekly huddles. So have extra one-on-ones with your difficult employee. I know that difficult employee's the last person you want to be talking to, but do it [laughter]. Just do it and actually get them across the finish line.

So those are the three steps. Acknowledge why their behavior could be that way and step number two is to actually be direct. Give them firm deadlines, set boundaries, let them know what your expectations are and number three is to set them up for success. All three of these steps will not only give you clues onto whether or not this person is manageable but, hopefully, in the long run, it'll actually turn that difficult employee into an exceptional employee. It is possible and I have seen it happen over and over again.

We are at a time when people need you to be a leader. They need you to step up to the plate and this brings me to my final point, which is as I talked about before, it's possible that the reason that you're not getting promoted is because you haven't spent the time to actually solve the situation with this difficult employee. So it's important that you're checking in with your boss along the way about what's going on. Now, this isn't the same as my first scenario, which is complaining to your boss or making excuses to your boss, but share your wins. So if the difficult employee actually starts to turn around and get better, let your boss know. Be excited about this, let that person-- send an email out to your team, celebrate them. Just because they've been a jerk for a really long time and they just had one win doesn't mean you can't celebrate that one win. Give them kudos. Let your boss know what you're doing, what the process looks like, and how you are fixing the situation.

And then, of course, go to your boss for guidance if it looks like, at the end, and you have gone through all the steps that I talked about-- and let's say you've gone through all those steps three or four times, and you have it documented, and you've tried this and you've tried that, really make sure that you're doing something very different every single time. Don't just repeat the same process over and over again and then go to your boss and say, "This person's not fixable. This person's not manageable. I don't know what we should do with them." Instead, say, "I tried this and I did these things specifically, and then I went to him and I gave him these three things specifically, and then I tried this." And at some point, you probably should have talked to your boss in the middle of this process anyway so that you can start to get input and feedback from your boss as to what's working and what's not working.

So that's it. This is how to deal with a difficult employee. I wish you all the best during this challenging time, but I'm also very hopeful for what lies ahead for the future of leadership. I think that this is a time when we're going to see a lot more compassion, a lot more empathy, rising to the top and compassion and empathy does not mean getting walked all over. It doesn't mean not setting boundaries and it doesn't mean not dealing with your difficult employees. I hope you find this useful and I look forward to seeing you next week.

Bye.