We’ve all had that one employee who seems to be intentionally working against us. Maybe they do good work, they just have no interpersonal skills. They might have potential but just have the worst attitude. Or maybe you can’t think of a single positive thing about them, yet, here they are. You have tried carrots. You’ve tried sticks. Your boss asked you to coach them up, so you’re trying but it doesn’t seem to be making much of a difference. Well today we’re covering coaching that difficult employee, how it’s typically done, and why that won’t work. Then, most importantly, I’m giving you what to do instead. (Your mental framing and the exact words to use in your coaching discussions are covered HERE on YouTube!)
The normal way to coach, won’t get you where you’re going.
People typically coach a difficult employee like this. They say something like, Hey bud, I know you’re super busy. I know we’ve asked a lot of you and you are doing your best. I’m just wondering if you could try to have a little better attitude. It makes it hard for other people to do their job when you say things like you have been. I know, I know it’s been a lot. Like I said, I know you’re trying. I just want to mention something so I can help. You know? I’m on your side. If there is anything I can do to help, just let me know. Read that out loud, does that sound like you coaching? If it does, I have news for you, you just ran backwards rather than taking the step forward you intended.
When you ‘coach’ this way your team member will walk away with questions. They’ll ask things like, Was that correction or a compliment? I wonder what they could do to lighten my work load? They’ll think, at least they know it’s not my fault I’ve been short with people. Now I want you to ask yourself, What was the goal of that conversation, and did you hit it? Are you coaching them to improve or begging them to do the minimum? When we sit on the outside looking in we can see that this, is not how we want to coach. You want to be compassionate and transformational. You want that team member to walk away clear on what to improve and inspired that they can.
Coach to elevate expectations
Today we’re going to break down what is wrong in that coaching and what to do instead. First and foremost, we need to look at the overall tone. When you approach coaching with a hey I know this is hard but do you think maybe you could try to ___, you’re setting yourself, and your team member up for failure. You are giving up your power as the leader. As the leader you can’t coach success by begging for the bare minimum. Instead, come to the conversation clear on what your expectations are and what living those expectations would look like objectively.
When you coach employees, even the most difficult ones (especially the most difficult ones) you approach it with confident power. Your confidence comes from clarity. That means even before you enter the room, before the conversation starts, you know what you expect. You expect respectful questions and comments, clocking in on time, people to speak up and take initiative when they have questions, you expect people to respond to emails, calls, or messages in 24 hours. Whatever the expectation is, be clear with yourself. That clarity will give you confidence to give compassion to the one offs and conviction on the standards.

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Focus on the work, not how it feels
Now that we’re in a clear and objective state of mind, let’s carry that into the coaching conversation. Your intent to acknowledge efforts that people are making are great, and we’re going to use that, with our clear objectives, to open the conversation. Because you absolutely can support and show compassion for effort, without falling down the hole of commiserating on business. So, rather than saying, I know you’re so busy and trying so hard, let’s flip it to be objective and positive. You could say, I appreciate the overtime you’ve put in to complete this analysis. My intention is to have this wrapped up in the next 2 weeks so we’re back to normal working hours.
Focusing on feelings can have you both digging deeper and deeper holes because yes, misery loves company. The thing is though, every emotion is contagious and you get to decide which one you’re spreading. Staying objective and positive essentially lifts their chin to see where we’re going. They see a light at the end of that over time tunnel. They feel your appreciation for their time and work. Also, they understand that you expect their continued dedication. (Expectations and appreciation can coexist) You didn’t use that work or time as a crutch for any other behavior. At this moment you’re establishing yourself as the leader, as the coach, and you’re just in the opening lines of this conversation.
Be direct about success
In our example of how managers typically coach poor attitude and behavior, things got really squishy when the boss asked for better behavior. Honestly, there was no specific ask or expectation set out. Managers usually just ask if employees can try to be better, and then rattle off excuses. It sounds like, Could you try to be nicer to coworkers? I know they start it sometimes. Or they’ll say, Do you think you could maybe be a little more positive in meetings? I know there have been a lot of hard pills to swallow, and I don’t like them either, but could you try to just not be as negative maybe? Unless you have a true concern or something you think we need to know. There is a way to get your point across and maintain respect on both sides of the conversation.
In your coaching explain what success looks like. Now, that could apply to anything in your work but today we’re talking attitude and behavior so, it could sound something like this: A successful analyst can performs meticulous review of the data and builds strong, respectful relationships so that their analysis can be used effectively. That looks like asking for input, listening to questions to understand the need, and answering them with the intent to build everyone’s knowledge. Being direct about what success in a role or situation looks like keeps the focus positive. You don’t have to waste time on every single thing that went wrong. You get to focus them on where you see them going.
It’s as if you’re hiking a trail with someone who is trudging along, dragging their feet, complaining about the roots and rocks. You finally decide to stop begging them to stop complaining, even though its hard and the roots are big. Instead, you gently lift their chin to get a glimpse of the 100 year old trees and the running deer. You focus them on why you’re hiking in the first place.
Empower them to make the fix
If you want to really be next level in your leadership, empower that underachieving, difficult to work with employee, to make the fix for themselves. Now, I’ve had people argue that they are empowering the employee. They ask that employee to maybe, please, consider trying to hit the minimum standard when they’re able. Then they end the request with, and let me know if I can do anything to help, and see that as empowerment. If that is what you’re doing, I need you to know that you didn’t empower them, you stranded them.
Empowering someone means to give someone confidence in their authority and power to do something. It means that you’ve set the vision for where they could go, and gave them the confidence to determine their own route. If you haven’t set the vision, the end goal, and you haven’t shown your confidence that they can get there, you didn’t empower. You stranded them. You communicated that you’re uncomfortable with how hard things are and told them to figure it out, while also basically telling them it’s OK if they never do. Once you’ve come in with clarity and confidence, you set the vision, the end goal of what success looks like for them. Now, you simply ask them, what do you think would be the best way to get there? Now, that, is building confidence in their power to get it right.
Coaching requires a coach
I hope you’re reading this thinking, ok, I’ve got this. I’m changing how I interact with _(that one person you’ve been imagining the whole time)_. But before you set out with your notes to transform your coaching abilities, I need you to stop and consider something. Who is coaching you? To transform your capabilities as a coach, you need a coach.
Let me explain. A coach is there to guide you to your full potential. Meaning, your coach helps you transform into the leader you desire to be. So, to give that difficult employee (and your star team members too) the best shot at the successful vision you laid out for them, you need someone guiding to yours as well. You need a coach who can lift your chin to take your focus from how hard this one employee is to the vision of the transformational leader you’re becoming. Do you have that coach guiding you to the focus, clarity, and empowerment in leading yourself and your team to the best versions of yourselves? If not, we should talk. Click here and reserve some time to find out what could be possible for you in coaching.
