One of the most difficult aspects of leadership is also one of the best aspects of leadership which is dealing with people. 

I believe you have to love people in order to be in a leadership position but it can be really hard to navigate if you’re not equipped to deal with the different personality styles, strengths and even difficult personalities on the team.

So today, I wanted to talk about managing difficult employees because I know it happens and I know it’s tough. 

Would you prefer to read rather than watch? Not to worry! You can read the blog post below.

But first, to really help you stand out in your new role I highly recommend downloading The Ultimate Guide to Being an Effective Team Leader.  A free downloadable interactive guide to help you show up and stand out and take the right action steps.


Let’s start out with the first difficult employee type, the complainer or the person that tends to make things out to be bigger than what they really are. 

I think we’ve all worked with someone like this that just always seems to create a mountain out of a molehill. 

Every project is a big deal and they let the entire team know how utterly challenging it’s going to be to embark on it. 

This type of person is really damaging to the team for obvious reasons as we need the cooperation and buy-in of the entire team for things to actually come together. But if there is one person that tends to point out all the negatives and complain about things every step of the way then it can absolutely make it draining for everyone else. 

A lot of times it falls into three buckets or categories:

*It could be because they believe that they have way too much on their plate when really they don’t know how to prioritize their day or workload

*They really do have way too much on their plate and don’t feel supported?

*They don’t know HOW to do the work they are being given

In all categories their default is their form of procrastination — which is complaining about things rather than doing things. 

For you as their manager you should approach this in two ways. 

*Since their overwhelm causes them to complain, approach them about their workloads and help them to either better manage their day and tasks or provide them with the support that they need so that they aren’t so flustered and overwhelmed. 

*Shift their perspective by getting them to pair their complaints with solutions. Every single time they bring a complaint to you or mention a complaint in a team meeting, bounce things back at them by saying “Hey Sally, thanks for bringing those issues to the forefront. I’d like to hear how you think things should be handled moving forward.” Get their minds thinking in terms of solutions rather than problems. 


The next difficult employee type is the yes person. 

This individual on the surface might seem great because they are the ones that say yes to every project, every task, everything but they fail to follow through on their commitments which leaves you not being able to trust them to deliver as promised.  

Obviously this is extremely frustrating and doesn’t make that individual feel good about themselves either. 

Again, merely a symptom. In some cases it’s poor planning, fear or even just the people pleaser in them wanting to say yes knowing that they can’t. 

With this individual, a step back to determine the root cause is essential. This is because it will affect the education you provide them around planning or saying no. 

But also on a more tactical level, you being clear on the expectations is really important. They need to know not just WHAT you need them to do and by WHEN but also the consequences of not following through on their commitments. 

I think sometimes as managers we forget that part of the equation when we set expectations – and it is important for people to know what the fallout is going to look like, especially for someone that seems to always fall through. 


The next type of difficult employee to work with is the know it all. I don’t think we can have a video talking about managing difficult employees without talking about the know-it-all it’s just not possible. 

I worked with someone like this ( not on my team thank god ) but someone laterally who was always talking a lot on topics that she considered herself to be an expert on that she really wasn’t. And it was annoying and frustrating even though I didn’t manage her. It was still annoying and I’ve heard some stories from clients of people that they manage that do the same thing. 

Something that I noticed about her, and you will probably notice about the know it all on your team –  is that the incessant need to talk about all the things they do know is really again just a symptom of their insecurity.

For whatever reasons they either don’t feel validated either in their personal life or at work and so it comes across in this need to showcase their knowledge wherever they can. 

So for you one of the best things you can do is learn how to balance the beam of recognition with firmness. 

The other thing that’s extremely important for this individual is having a direct conversation with this person around what’s happening. 

First off, if it’s annoying for you can you imagine how annoying it is for the team? In fact, a lot of times this causes a subtle divide and then work is not done effectively on any level because people aren’t working together collaboratively. It might not seem that way on the surface but it always is layers deep.

The other thing is that the know-it-all is not aware of how they are coming across and so you as their manager need to bring this to their attention in a way that is direct while still treating them with dignity and respect.  Choose your words carefully and be delicate but direct and firm. In the New Manager Accelerator I teach my students a framework for having sensitive conversations just like this because with this person knowing that insecurity is an issue you don’t want to be the straw that breaks their back. 


The next difficult employee type is the person that always comes to you to solve their problems.

They have a job to do and somehow they are in your office, sending you emails and double checking everything before making a decision. 

Again, a symptom and it falls under various buckets. 

>>They lack critical thinking skills 

>>They have critical thinking capability but they lack confidence to solve issues on their own 

>>They lack the training they need to whatever it is (so the support hasn’t been provided along the way) 

>>They are being micromanaged by you so they feel as though that’s what you want them to do 

>>They’ve been in an environment before with a poor manager (which there are plenty of) and so they have been conditioned to not do things on their own. 

I went to a leadership conference a couple years ago where the speaker was talking about the concept of the monkey that was taught by Steve Brown who was a leadership expert. 

The concept is that when people come to your office and say ‘hey we’ve got a problem’ you have to immediately visualize that they have a monkey sitting on their shoulder that has jumped off their shoulder and has made it onto your desk and that your job is to get them take their monkey with them when they leave. 

Essentially in a very visual way he was trying to say as the leader don’t take on the problems yourself. Yes, support them in solving the problem but don’t take it on yourself because you’ll never have true progress like that. 

My mentor used to say “Mak people are paid to solve problems and so if I’m having to solve their problems for them why are they getting paid?”

I agree and have adopted that mentality myself. I want to create a supportive and collaborative environment but at the end of the day everyone is getting paid for the complexity of the problem they are solving. So if they are getting paid to solve issues and you’re doing it then that problem has a really high price tag. 

So how do you do this? How do you strike that balance of providing the support and not solving it for them?

One way is to put it back on them the first time around. Hear them out and even if you have the solution say: 

“Thanks for bringing that to my attention. Here’s what I’m thinking though, I have a lot of confidence in your ability to come up with solutions for this. How about you take some time and think through a couple of different solutions and come back to me when you have about 3 and we can discuss from there the best path to take forward.”

This way they are leaving your physical or virtual office with their monkey and you are training them to solve issues while still providing the support they need when they come back with a well thought out solution. 


The next difficult type is the gossiper. We’ve all worked with people like this that just love their tea and love spreading it just as much. 

This is such a tricky one because the gossiper in a lot of cases, not all – but some cases is often the friendliest most liked person in the crew and so you want to love them but they spend way too much time spreading cancer. 

It’s dangerous no matter how lovely they are as it causes trust and productivity issues as people are wrapped up in the story rather than what they are being paid to do.

There are two antidotes to dealing with the gossip and one is steeped in the culture that you have defined as part of your standards. 

It’s important to remember that if you allow gossip in any form, then you are saying that you condone the behaviour. 

Always step back and ask yourself if as the leader of the team you have either allowed or set the wrong example when it comes to gossip. 

Personally I’ve been guilty of this. Where I’ve allowed things to get out of hand because I refused to either step in or I participated in it myself. It’s so easy to get sucked into the tunnel when crap is happening but it’s distracting so you gotta pull yourself together if you are going to demand that others not do the same as they are following your example. 

Secondly, make sure you are being transparent with the team about what’s going on. The more you leave people out, the more prone they are to fill in the blanks and it leaves room for the gossip to spread stories and create a narrative. 

So aim to have a transparent communication plan for the team whenever things are happening. Don’t wait to discuss something. Be clear about what’s happening or going on as close as possible to any incident or change so that you get in front of things.