How to help your employees better navigate the workplace

After over 40 years of managing people, I’d like to think I’ve seen and heard almost everything. Still, I believe in the saying, “Behind each set of eyes, there is a story.” I know I can’t always trust what I think I’m seeing.

If you only get one thing from this post, I hope it’s this: Ask your employees questions, and listen to the answers.

It’s that easy.

With the right people on your team, hard conversations can reach deeper issues. And by listening to understand, you can redeem a difficult situation and turn it into a growth opportunity for you and your staff!

Here’s how I like to navigate 10 tough conversations in the workplace. These are all real situations I’ve had to confront with employees over the years. It was rarely as simple as I thought it would be, but that’s part of what I love about being a manager. People always surprise me. And when I help someone grow personally and professionally, we both win!

  1. My employee writes poorly
  2. My employee doesn’t perform up to their ability
  3. My employee resists constructive feedback
  4. My employee lacks self-confidence
  5. My employee speaks decisively where they have no depth
  6. My employee uses company chat for non work-related issues
  7. My employee acts like a supervisor when they’re not
  8. My employee undermines my authority
  9. My employee manipulates company politics
  10. My employee isn’t a good fit for the team

1. When one of my employees writes poorly…

What’s your first reaction when one of your employees’ reports, emails or slideshows is full of jargon, spelling mistakes and vague statements?

But before you talk to them, make sure it’s actually a problem.

Does their audience care about the mistakes?

Are their mistakes confined to emails to you and their coworkers? If so, then it may not be important to address it, especially if you get the gist of what they’re saying. (That said, it may not enhance their reputation around the office, so you may still address it.)

But if they’re creating materials for higher ups, customers or advertisements, it’s definitely worth the time and effort to coach them to better writing. You don’t want your employee to lose a promotion or client because they had a bad tone, or they misspelled too many homophones.

There are plenty of reasons why people don’t write well, but let’s explore some practical steps you can take to make their poor writing less of a problem.

Look at their job description

First of all, is writing a key component of the job they’re being asked to do?

If so, they may be in the wrong job.

Sure, most people can improve their writing over time with coaching and motivation. But if you’re running a business and not a school,  you need your employees to do the basic aspects of their job without loads of extra training from you.

Problem: Your employee writes poorly from a writing-intensive position.

Solution: Move them to a less writing-intensive role.

Look at their workflows

When was the last time your first draft was your final draft? Hopefully never.

Even the best writers write terrible first drafts, but you never see them. Why? Because there should be a buffer between us and the writer: a copy editor.

Sometimes you have creative people who are great with concepts and messaging. The problem is they don’t know the difference between an adverb and a participle. That’s okay! Creatives are very valuable people. It’s up to you to give them editors and tools to help them craft a clear, compelling message.

Their editor could be you, a coworker or a freelancer who knows and understands your business.

Don’t have the resources to get them an editor? Get them a free writing and editing aid, like Hemingway editor, ProWritingAid or Grammarly. (My go-to is Hemingway.) Even good old spellcheck does wonders. And don’t forget to make sure they have a fresh copy of your company’s style guide. With the right tools, your employee can become their own editor.

Problem: Your writer has great ideas but poor delivery.

Solution: Get them a copy editor.

Look at their attitude

Does your employee understand that good writing is important to their success? Maybe they ignore spelling and grammar because they think delivery doesn’t matter as long as people still understand what they’re saying.

Perhaps they just don’t care.

You need to get them to care.

Have  a 1-on-1 meeting and explain why their poor writing is a problem. Describe all the impediments it will put in the way of their advancement in the company. They need to start caring about those red squiggly lines if they want that promotion next month.

Problem: Your writer doesn’t care about delivery.

Solution: Coach them into caring.

How to talk about their poor writing

Meet with your employee 1-on-1 as soon as you realize that their poor writing is more than a one-time mistake.

Your goal should be to coach them, not shame them.

Come prepared with a few things:

  • Examples of their poor writing: Select a few key examples of each type of mistake. Then group their mistakes— like Exhibit II in this article. Your employee needs specific examples of what they need to watch out for as they try to improve.
  • Explanations for why each infraction was inappropriate in its context: Describe why typos are easily overlooked in their emails to you, but not in their emails to the department head. They need to practice adapting their writing (and their proofreading) to their audience.
  • Solutions to improve their writing: Brainstorm a few ideas yourself beforehand and then ask for their own ideas during the meeting. There’s a good chance they’ve dealt with this problem before. If so, they’ll know what does and doesn’t help.
  • Example of what you want their writing to look and sound like: Draw from your own archives to find examples for your employee to analyze and follow.

Give them time to get better

If better writing is key to their professional success, you as their manager need to help them. Provide time for them to improve as a part of their daily work, which will show them you value them personally and professionally. It should motivate them to improve, and you’ll reap the benefits when they do.

You could send your employee to a business writing seminar or coach them yourself; whatever you do, try to adjust their workload accordingly. Adding extra work to their already full schedule will only stress you both out. They shouldn’t have to choose between improving their writing and completing their objectives.

How I actually handled it

Jenna was an excellent communicator. Sure, her writing had a couple grammatical issues, but it was easy to imagine that she’d be an energetic and effective writer.

I was wrong.

Being a good speaker is quite different from being a good writer. Jenna had struggled with organizing her material and using proper grammar and punctuation; she somehow even managed to outsmart spellcheck—there were spelling errors everywhere. For whatever reason, her communication skills left her when she wrote; she just choked. And the resulting feedback she received shook her confidence.

It didn’t take long to figure out that writing wasn’t in Jenna’s career path, but I did want to help increase her skill. After all, everyone has to write emails. I didn’t want her to burn out on a promising career because she couldn’t write.

I recommended some online tools like those listed above, but I wasn’t sure those solutions would help Jenna organize her thinking. Because she seemed to have no problems communicating when  talking, I suggested she take a different approach.

I said, “Why don’t you start by recording what you want to say into the voice memo app on your phone? Then, transcribe it as your starting point.”

Remember when I said speaking is different than writing? It’s true. And Jenna proved it.

Sure, she still needed some editing for grammar and spelling, and writing was still hard for her. But this solution helped her a lot. We saw a marked improvement in her output and her writing stopped being the Achilles’ heel of her career goals.

2. When one of my employees isn’t performing as well as they could…

I’m going to assume here that your employee is capable of excellent work. Why else would you have hired them?

Even if they’re new, it’s most likely that they’re underperforming on just one or two of their tasks, not on everything. As hard as it can be to watch an employee struggle, do your best not to express any disappointment.

What I mean is this: focus on your employee’s struggles in work and production, not on them personally. Try to frame the issue in a way that doesn’t come off like you’re doubting their value or worth.

There’s a reason your employee is putting out substandard work. Your job as their manager is to find the “why” behind the “what.”

Let’s look at a few of the most common reasons for underperformance I’ve encountered. Then, I’ll talk about the best ways to have that tough conversation.

They’re not suited to the task

Everyone has strengths and weaknesses. The best way to engage your employees and excel in your industry is to help them play to their strengths and passions; and the sooner you can learn what those are, the better.

We all have skills. Sometimes it’s not that your employee isn’t good at a task; they just don’t know how to do it. So they’ve been bumbling along, trying their best but failing a lot. Perhaps you’re expecting them to do something they’re not capable of doing.

Would you give someone with terrible grammar a job as your head writer? How about putting someone with no technical savvy in charge of your infrastructure?

I hope not.

When you realize you gave an employee a task they’re not qualified to complete, adjust their responsibilities as soon as possible. See if you can switch tasks around; find a coworker better suited to the task and give your employee a project they’ll be good at.

Do a just a little bit of job sculpting and you’ll see what amazing things your employees can do.

They don’t understand the task

I’ve learned that the clearer you can be at the outset, the better.

When you give one of your employees a new task, be as clear as possible. Describe the scope, deliverables and deadlines more thoroughly than you think necessary, and do so face-to-face. Give them a written summary for reference.

But even if you do everything right, it’s still possible your employee won’t understand the expected work quality. So it can be helpful for them to see an example of your ideal.

Hopefully, they’ll remedy the issue as soon as you point it out to them, but if not it may be time to transfer them to a different role, or even out of the company.

They’re tired

People aren’t robots. At some point we run out of steam and need a break, or at least some well-worded encouragement to get us going again.

Is your employee underdelivering because they’re going through something hard in their personal life?

Be careful about being too personal, but try something like this:

“I’ve noticed that your reports aren’t up to your high standard. Could you help me understand why that is?”

A more general question like that opens the door for them to say…

“To be honest, I haven’t been able to focus at work very well this quarter because my wife got diagnosed with cancer.”

Then you can offer your sympathies and make adjustments for them as they walk through this hard time. You could offer a lighter workload, some extra time off, or fewer big projects; whatever you can do, your employee will appreciate your help. Your goal is to make sure they feel like they are still valuable—both during and after the crisis.

Scrap excuses

As you dig deep to find out exactly why your employee isn’t doing well, listen to their excuses. Most people get defensive when they’re told that they’re underperforming; I know it’s my first instinct.

But don’t dismiss your employee’s excuses just because it seems like they aren’t owning their failure. There could be some validity to them.

There are dependencies with certain work. If your employee’s pipeline is empty, can they do anything about it?

Talk through each of their excuses with them. Discussing how they could have dealt with each one empowers them to improve next time; it will help prevent them from getting stuck by the same obstacle over and over.

It’s a good idea to have your employee document any obstacles as they come up. Ask them to talk with you when they feel as though these obstacles might affect their productivity. The goal is to understand and deal with problems as they arise so they can be dealt with and moved past immediately, making excuses for lack of output irrelevant.

Start the transition process

Unfortunately, there’s always a chance that your employee may never meet your expectations. It can feel like you’ve failed them as a manager, but don’t give in to that. If you did what you could and your they didn’t respond, that’s on them.

No matter how thorough your interview process is, not every person you hire will be a great fit.

Let me state the obvious: If someone consistently underperforms, you need to document it and move toward dismissal. Underperformers not only affect productivity, but your work culture as a whole.

Your other employees know who the weak link on your team is. If you aren’t dealing with it as a manager, it will erode their trust in your leadership.

The key to a smooth dismissal is to Put together clear expectations and document the results. Keep tabs on issues as they arise, and if your employee doesn’t meet your standards, it’s time for them to get a new job.

How I actually handled it

Mitch was a great guy. Friendly, intelligent and talented, everyone wanted him on their team.

But each year, I got the same report: Mitch wasn’t getting any work done, and (he thought) he always had a reasonable explanation.

We tried him in 3 different departments. Each time, his new supervisor welcomed him, hoping that this time it would be different. But at the end of the year, Mitch always still managed to underperform.

I spent a lot of time with Mitch. I met with him to help him get organized and we agreed on meaningful assignments with clear deliverables. I tried my best to empower him to do work that he’d both enjoy and that he would be qualified to do.

Nothing worked.

The more I tried to help Mitch, the more I realized that he was comfortable with a slow pace—a very slow pace. He didn’t do well with hard deadlines, he was easily overwhelmed when urgent matters came up and despite his talent he had a hard time knowing what to do next without being spoon-fed.

I had an honest conversation with Mitch where I tried to help him understand himself a little better. Eventually, I suggested that he find a less stressful, more structured job. After some time, he did and ended up a happier guy with delighted managers.

3. When one of my employees resists constructive feedback…

As managers, we want our employees to do well – and learn to do even better. The problem is, how do we help them?

The answer is constructive feedback.

Or so we’ve been told.

But every time you give constructive feedback, this particular employee:

  • Blows up
  • Denies the problem
  • Seems to agree but never changes
  • Runs away

Here are 2 possible solutions for improving employee reception of feedback.

Change how you deliver feedback

Nobody’s perfect. I’m not, and neither are you.

The reason your employee balks at your feedback could be because you’re not very good at it.

Are you…

  • Using a compliment sandwich?
  • Describing the issue too vaguely?
  • Blaming them?
  • Ambushing them?

Any of the above would keep most people from internalizing and acting on feedback.

Compliment sandwiches and vague descriptions cheapen constructive feedback by making it easy for your employee to dismiss. But using language that blames them or ambushes them only makes them bitter, and you end up with an employee who doesn’t internalize your constructive feedback.

To avoid these pitfalls, approach feedback conversations with 2 attitudes in mind:

  1. “I will be clear.”
  2. “I will be kind.”

Any time you give constructive feedback, resist the urge to beat around the bush. You’ll only waste time and confuse your employee. Leave no room for interpretation as you describe what you want your employee to change, and give them actionable steps to start as soon as they leave your office.

But don’t forget to give them a chance to speak up. Kindly ask if they’d like to explain why they’ve been doing things a certain way.

The results will speak for themselves.

Focus on their reception of feedback—not on the feedback they’re ignoring

If you don’t see improvements after ensuring your approach is clear and kind, it’s time to have an even more difficult conversation:

Their unresponsiveness to feedback.

The solution isn’t to have another conversation about why they still haven’t changed; instead, you need to have a one-on-one meeting confronting the issue of why they’re just not listening.

Often, employee inability to accept constructive feedback extends far beyond the workplace. I’ve seen it connected to self-confidence, and that’s a tough thing to confront.

Even the best people experience the Dunning-Kruger effect: essentially, we like to think of ourselves as exceptional and talented while ignoring our shortcomings. In this case, your employee has overestimated or overlooked their weaknesses, and they don’t understand why you think they need help.

In most cases, open discussion is the best approach. Give clear examples of how they’ve responded in the past and how they might have handled it better, and give them some power by asking how they would like you to deliver constructive feedback.

Eventually, you’ll be able to start focusing on specific pieces of feedback again.

How I actually handled it

When I started a new job as a senior director, there were several managers reporting to me. I sat down with each of them and their employees to get to know them; I wanted to understand their needs so I could help them grow and succeed.

It didn’t take long to figure out that I was going to have have trouble with Mike.

Mike managed an incredibly important department, but after talking with his employees, I could boil his leadership philosophy down to one word: authoritarian. Mike’s military background meant the chain of command was central to him. Unfortunately, to him that also meant unwavering inflexibility. His employees learned there was no disagreeing with Mike – it was like talking to a brick wall.

As we worked together, I ran into the same problems as his employees. His department needed a philosophical overhaul, and Mike’s stubbornness was going to make it hard.

I could have just replaced Mike, but he was doing a difficult job that few wanted to do, and he had a lot of talent. So I decided to try to help him grow. After several failed attempts, I finally landed on a strategy that worked:

Whenever I approached Mike, I would first encourage him in areas of organization and process that were important to him. I spent a good amount of time pointing out specific strengths that he possessed that impressed me. From there, I outlined the issue I wanted to address and gave specific examples of how his employees’ strengths could help him solve the problem. He began to see that others had good ideas too, and that he could trust his team to help him figure out the their problems.

It was never easy to give Mike constructive feedback…. He generally pushed back. But helping him understand his team’s capabilities helped build trust on his team, and ultimately, opened him up a little more to constructive feedback.

4. When one of my employees lacks self-confidence, failing to speak up when they should…

As managers, it’s easy for us to see our employees’ untapped potential. Every day we see how hard they work and the amazing results they produce.

But sometimes, our employees see it differently.

They think their promotion was a fluke, and that they just got lucky. They don’t understand their amazing potential and can’t comprehend why you deemed them worthy of promotion; they barely feel like they deserve the position they currently hold.

To you, it looks like your employee is lacking confidence. So what can you do to help them overcome such a deep-rooted issue?

There’s no scripted formula to boost your employee’s self-confidence, but let’s take a look at some best practices for dealing with an employee who’s timid and uncertain.

Build a safe work culture

You have to start with one important question: Do your other employees feel comfortable speaking up?

Some other ways to ask that question and get you thinking:

  • Do projects fail because no one with key information spoke up?
  • When you ask for honest feedback – either from groups or from individuals – do you get it?
  • Are there certain things that are off the table for everyone, things even you don’t feel comfortable talking about with your boss?
  • Are people’s suggestions often ignored or unresolved?

Did you answer yes to any of those? If so, perhaps your organization needs to re-examine how feedback is handled. You need to change how it’s encouraged, received and resolved.

Create a safe place to speak up by doing so yourself. Be a role model for your employees; show them when to speak up, how to do it and how to follow up. Granted, this will mean being more open in your conversations, but your employees will recognize and reciprocate your vulnerability.


Even if those you report to don’t respond as you wish they would, you can still choose how you respond to feedback.

When an employee raises a concern with you, start with affirmation:  Listen, smile and nod. But don’t let it stop there; always to follow up, even if it’s just to say:

“Mary, I appreciated that you brought that issue to my attention last week. I talked with those involved, and we’re going to take a wait-and-see approach. Since we’re not acting on it yet, I want to make sure you know we’re still watching it. Because you said something, we’re prepared to address the problem if it escalates. Thanks again for bringing it to my attention.”

Reward—publicly—employees who speak up

I came across an interesting cycle for building confidence.

When a risk pays off, we get a confidence boost and feel more comfortable taking more risks.

So self-confidence, which seems fundamental and unchangeable, can be tangibly boosted.

Make sure you recognize everyone’s feedback immediately. It willl build a feedback-safe workplace for everyone, even the quiet, seemingly insecure ones.

Even if you don’t have an immediate answer, you need to have an immediate response. If one of your employees speaks up, try to respond immediately with something like this:

“Jared, thanks for speaking up. I’m going to take a closer look and get back to you on that. If I haven’t gotten back to you in a week, please bring it up again. I really appreciate you speaking up.”

Are you trying to boost the confidence of one specific employee? Give the whole team lots of public recognition. Your specific employee will see you rewarding others for speaking up and feel more comfortable following suit. And when they do speak up, your immediate encouragement should be a positive payout. It’ll build their confidence and make them more likely to speak up again.

Follow up on what your employees say

A big reason your employee doesn’t speak up – maybe the biggest one of all – could be because they think it’s futile.

You think they’re suffering from low confidence, too afraid to speak up when they should. But perhaps what’s really happening is that they don’t see any point in speaking up.

How did that happen?

Well, here are some possibilities…

  • You dismissed their feedback, or someone else’s feedback.
  • They never saw the effect of their feedback.
  • Upper management solicits feedback but never acts on it.

Now, I’m not suggesting you have to act on every piece of feedback you receive. In fact, Please don’t.

Instead, begin any feedback requests with a reminder that you can’t act on everything you hear. When your employees know this in advance, they won’t be disappointed when you don’t act on every single suggestion they give.

You have to do a little more than have a simple disclaimer, though.

You’ll also need to follow up with your employee. Even if their idea was terrible or irrelevant, still affirm them for speaking up. And, if possible, tell them why you’re rejecting their comments. When employees know why you put aside their feedback, they’re less likely to be bitter about it.

Change how you talk to them

Okay, so let’s say you have a healthy feedback culture; your employees give you great feedback all the time.

Except for one employee.

Despite everything you’ve tried, they don’t speak up. There’s something about your workplace that makes them feel uncomfortable, unsafe, or unsupported.

Here’s one solution:

Get to know your employee better.

Take a look at how they carry themselves and interact with their coworkers. Do you know what motivates them? What kind of feedback makes them feel valued and appreciated?

For example, let’s say they don’t like enthusiastic praise; either they don’t believe it or they’d prefer more constructive feedback; something realistic but with an encouraging lilt.

When you think you have a better handle on how they function, meet with them one-on-one. Ask them to describe three situations where they feel they were successful, and try to understand what parts of the process made them feel it was a success. Then frame their work in the same vein as their successes.

Remember, you can’t talk someone out of low self-confidence, but you can open opportunities to bolster it. Sometimes, it’s as simple as reframing situations to help them see themselves like you do. Other times, books, training seminars or team activities could work. Be creative!

Reexamine your team

Almost everyone feels comfortable weighing in, so that means your culture is good to go, right?

Well, maybe not.

Perhaps many members of your team might have similar personalities, so your particularly quiet, under-confident employee sticks out like a sore thumb. It may seem like your they are the problem, but the real problem might be your team.

We like to surround ourselves with people who think about and solve problems like we do. When we all have a similar mindset, it’s easier to move forward quickly with fewer conflicts. Except that’s exactly how you get in trouble.

Start by asking your employee what they think of your culture.

Does the current extroverted team dynamic make it difficult for them to weigh in? Are their coworkers too emotional in their instinctive responses? Is there a certain coworker who never reacts to their ideas well? Do they come from a culture that handles conflicts differently? Are they afraid of seeming like a know-it-all?

Identify the fear or obstacle keeping your employee from speaking up more often. Together, brainstorm how they can overcome it. Make it clear that their contributions are vital to your company’s success and you’ll do whatever it takes to help them speak up.

How I actually handled it

We have an active workplace, and sometimes it’s hard to get a word in. Certain people in our company (including yours truly) take a breath and talk for 15 minutes. It doesn’t always encourage spirited discussion.

Mark was a fairly quiet guy, but was one of the sharpest guys on our team. In one-on-one discussions, I was amazed by his insights. I trusted him to balance out my over-the-top positivity.

It’s not that he was always negative; he just discerned obstacles and flaws in my plans. His voice was often the voice I needed and, curiously, there were times he remained silent when he saw me heading off a cliff.

When I first talked with Mark about the problem, he apologized. He agreed there were times he chose to stay silent. And sure, there were times it was hard to find the space to interject, but more often than not, he didn’t say anything for fear of being a “Negative Nelly.”

I realized I was the problem.

My optimism made Mark think his more detailed and balanced approach would irritate me. I explained that nothing could be further from the truth, and I needed him to be an effective leader; I encouraged him to speak up.

Initially, I had to jump-start the process.

When we were discussing an important issue, I made sure to ask, “Mark, what do you think?” It put him on the spot, sometimes uncomfortably, but soon he got used to the sound of his own voice in our meetings. Others complimented him on his keen insights and gave him the confidence to be who our team needed him to be—himself.

Sometimes, we need to look in the mirror and ask whether we, as managers, might be a part of the very problem we’re trying to fix. This one hit me like a ton of bricks, and recognizing it helped Mark become a more effective member of our team!

5. When one of my employees speaks decisively in areas where they have no depth…

There’s a difference between a know-it-all and someone who’s trying to be a know-it-all. A true know-it-all can be obnoxious, but they’re usually right; someone who’s pretending puts their foot in their mouth regularly.

When you’re sure your employee isn’t a real know-it-all, there are a few steps you should take. Get ready to turn their “fake it till I make it” attitude into an “I made it” attitude.

Point out what’s wrong with what they’re saying


When your employee digs themselves into a hole, document what they said and how they said it. Make notes about how their comment lacks depth and shows they don’t know as much as they’d like to think they do.

In a one-on-one meeting talk about why what they’re doing can’t continue; It frustrates their team, their credibility decreases, and the people who should speak up don’t get a chance to.

I’ve found it also helps to remind my employee that experts use a certain lexicon, and they betray themselves as outsiders when they use the wrong terms; even the wrong body language can tell their audience they’re bluffing.

Train them to talk about what they know

Sometimes, your employee just wants to impress whoever’s in the room. So to make up for lack of perceived opportunity, they end up talking about things they don’t know much about.

Take some time to teach your employee how to handle situations when they’re in over their head. However they got there, they’re their best bet to get themselves back on stable ground.

Give your employee some phrases for situations when they’re in over their head:

  • “I’m sorry. I lost my train of thought. Does anyone else have something to say?”
  • “I just remembered Bob knows a lot more about this than I do. Let’s go ask him.”
  • “Honestly, I don’t know enough about this to accurately answer your question. Would you check back with me in a week or so after I’ve done some more research? Otherwise, I know Bob has done this before. He might be a better point person.”

People will appreciate your employee’s honesty and humility. They’ll also appreciate that he suggests an alternative. It shows initiative even as he owns up to his own shortcomings.

Help them understand when they should and shouldn’t fake it

Faking it until you make it works – in the right situations.

Encourage your employee to think about when it is and isn’t okay to pretend they know what they’re doing.

It is okay when…it’s a matter of confidence.

When an employee lacks confidence, they’re the only person standing in their way. Faking it will get them out of their own way.

It is not okay when…it’s a matter of knowledge.

It’s never good to pretend to know more about something than you actually do; generally, you’ll end up being exposed. Help your employee understand the problem with speaking up when they shouldn’t.

How I actually handled it

By nature, I like to know a little about a lot of things. I don’t plumb the depths of anything – I’d rather leave that to the experts. Still, living in the software world means I need to actually know some stuff. Faking it doesn’t work.

Frank was a very capable guy. He understood technology architecture, and he was awesome at managing a team of to complete a project. Yet he sometimes hurt his reputation when he would speak authoritatively without the knowledge to back it up. In a room full of experts, he’d use the wrong nomenclature to describe technical processes; he came off as an incompetent poser.

When I met with Frank, I told him this true story:

Years before, I worked with a man who used to be an U.S. Army General and an executive at GE. As you can imagine, he was brilliant. When he first came to work with our organization (a large non-profit), he used a nickname to refer to our company. A nickname no one in our company would ever use. We did have a nickname – just not the one he used. By using unfamiliar terminology, the general did exactly the opposite of his intentions. He wanted to seem like a relational insider, but his use of the wrong nickname immediately made him an outsider.

I explained how people are far more forgiving of acknowledged ignorance than they are of presumptuous but mistaken expertise. Frank wanted to be an influential member of the team, so he was open to my feedback. I suggested that he ask more questions and use the answers he received to gain clarity. I also recommended he learn more about our products and services; ;hen, he could narrow in on an area of expertise he could use to gain the credibility he so desired.

I’m happy to report that Frank did a good job implementing the feedback, and he became a more valued member of the team because of it!

6. When one of my employees uses company chat forums for purposes that aren’t work-related…

Office communication tools like Slack and Yammer can be a blessing and a curse.

Used in moderation, they can foster collaboration and connection among employees. They can help offices be quieter, they tear down walls for more inter-departmental mingling, and they help remote employees connect with their coworkers.

But what do you do when one of your employees isn’t using it for anything even remotely related to work?

Update your chat policies and norms

I hope your employee handbook says something about using instant messaging tools.

Yes? Good.

Now, when’s the last time you updated them?

Instant communication tools are still new – they’re literally changing workplace culture as you read this sentence, and your policies and norms should evolve as your along with it As employees figure out how chat tools fit into their workday, you need to figure out how they can best benefit everyone.

Explain in your policies how employees can keep chats from becoming an addiction or distraction.

Here’s an example:

“We recognize the great benefits of our chat tool, but we also recognize that it’s easy to abuse. Instead of micromanaging how you use it, please just keep yourself in check. Every so often, ask yourself a few questions:

  • Are you using it more than others?
  • Are you as productive as you should be?
  • Do you spend more than 30 on it minutes per day?
  • Does it take you a long time to re-focus after checking it?
  • Are you more active on non-work-related channels than you are on the work-related ones? 

If you answer “yes” to any of these questions, please reign it in a bit. We want you to bond with your coworkers and have a safe place to speak freely, but we still need you to get your work done.”

Check their productivity

It feels strange to walk through your floor at 2 PM and see employees sending gifs to one another and laughing over inside jokes, right? It’s tempting to assume they’re wasting time. But most of them are just engaging in office banter; they’re just blowing off steam to stay engaged and focused.

When you think an employee is using the chat tool more than they should, check their productivity. Check their progress on projects. Are they at a roadblock or falling behind?

Then check their frequency; have they been overusing the tool for 3 days or 3 months? Make sure it’s a habit and not just an off week for them.

If your employee is on track with their projects and goals and they aren’t distracting others, let them be. The last thing you want to do is start micromanaging people who don’t need it.

Create some special guidelines

Is your employee’s (or their coworkers’) productivity suffering? Then it’s time to chat.

First, affirm them for contributing to a friendly workplace. It’s awesome that they get along with their coworkers!

Then give them a clear picture of what is okay. You need to start by agreeing on some concrete rules to guide their use of your office chat tool.

And make sure to explain why they need to step back from the chat rooms: it’s hurting productivity, and, frankly, it’s hurting their reputation. They don’t want to be the person who’s always goofing off, do they?

How I actually handled it

One of the things I love about our company is the family atmosphere our CEO has fostered. He cares deeply for his staff, and that carries over into the relationships we have as a team. We’re creative and hard-working, but we also laugh and have a lot of fun together.

When our company first started using Slack, everybody was using it improperly (myself included). It wasn’t like we were actively seeking out distractions from our work, but having company business on the same channel as the latest cute cat gifs just made it hard to focus!

We decided to separate our chat channels by teams, projects, and fun. When people need a pick-me-up, they go to the channels set aside for humor. Now, their in-the-zone focus time isn’t interrupted by the latest installment of “Carpool Karaoke.”

7. When one of my employees takes on a supervisory role when they’re not actually a supervisor…

Most people want to advance in their careers, but some people don’t wait for an official promotion before they start acting the part.

When one of your employees tries to act like a supervisor when they’re not, here are a few things that should guide your conversation.

Gauge its extent

It’s possible your employee has blurred the lines between mentor/leader and supervisor/manager. Eager to move forward in their career path, they’re doing their best to show you they’re management material – except they’ve crossed the line from showing their potential to taking over your job.

Think about which behaviors have been red flags. Do they:

  • Delegate their responsibilities to others?
  • Try to keep others on the team accountable?
  • Usurp your authority for setting vision and direction for the team?
  • Have others consulting them before they consult you on things that are clearly out of their scope—like PTO, HR issues, and project roadblocks?
  • Sense a lack of leadership on your part?

Before you act, get as much context as you can. Figure out how long it’s been going on and who’s been affected by it. Have they been a manager before? Do they need help understanding where it is and isn’t okay to flex their newly developed managerial muscles?

They could also just be trying to win at office politics as they clamber up the corporate ladder.

Consider who brought it to your attention

You noticed it on your own

Noticing behavior like this without a heads up from your employee’s coworkers could mean they’re trying to handle it themselves before bringing it to your attention.

That’s good! You want your employees to try to resolve conflicts on their own – it helps cut down on unhealthy dependency.

Set up one-on-one meetings with each person your employee is trying to supervise. During each meeting, describe the inappropriate behavior you’ve noticed that impacts them and find out how they’ve been handling the situation.

Do they feel confident dealing with their coworker without your intervention?

Then write up a plan so you’re all on the same page as to when you’ll step in. Set up a few follow-ups to hear how it’s going, and applaud them for addressing the issue on their own while stepping in just enough so they see you care. You want to find a balance between being attentive and micromanaging.

On the other hand, they might not have said anything to the out-of-bounds employee yet—either because they don’t think it’s a problem or because they’re unsure how to confront them.

Help them see why it’s a problem, and create a plan for how they can confront the employee. Make it clear that you support them and they won’t get in trouble for pushing back against the employee’s behavior.

Finally, agree on the point where you’ll step in to help mediate the situation.

Your employee’s coworker(s) brought it to your attention

If others are uncomfortable enough about it to bring it to your attention, it’s probably gotten pretty bad.

There are 2 likely reasons they came to you:

  1. They talked to the employee, but it didn’t help. They tried to resolve the issue on their own by asserting boundaries and making it clear that they’re equals, but your employee just isn’t getting it.
  2. The employee isn’t approachable. It’s gotten to the point that the stray employee has convinced their coworkers they have hire/fire capabilities and their coworkers fear for their jobs. Or the employee could be known for being so volatile that their coworkers fear an explosion of anger or some form of passive-aggressive backlash.

Either way, it’s time for you to step in. While you want to push your employees to handle issues themselves, it’s clearly gotten to the point that insisting they do so will only make it seem like you don’t care about the situation.

Check yourself

One of the most difficult things to do as a leader is to ask for feedback. There’s a chance your employee has been stepping out of line because they’re trying to pick up your slack. There are other signs you should look for that indicate your employees don’t think you’re managing them well. If you’ve been having a hard time getting respect from your employees, an employee stepping into your duties shouldn’t be a surprise.

Do you trust your employee’s opinion? If so, ask them where you can grow. Of course, do this carefully so that they don’t get the idea that they’re now managing you too.

Confront your employee

Odds are, you’re going to need to have a very frank conversation with your employee.

Here are some questions to guide your conversation:

  • Are you aware you’ve been doing things outside what’s expected of you?
  • Why have you been adopting more and more managerial duties?
  • Do you understand why you need to stop acting as a manager for your coworkers?

Before your conversation, reflect on past conversations you’ve had with your employee about their career growth. If your employee has expressed a desire to be a supervisor some day, come prepared to discuss how their actions are hurting their progress toward their goal. If they try to excuse their actions by saying they’re just trying to show that they’re management material, try saying something like this:

“I understand that, and I appreciate the leadership qualities you’ve displayed on projects X and Y. However, I need you to remember that you’re not a manager yet.”

It will help if you can give them a solid timeline of when they can expect to become a manager. Then, you can discuss ways you want to help them grow into the role without continuing to step on your toes.

There are 3 things you need to make crystal clear during your conversation:

  1. They need to stop acting like their coworkers’ superior/manager/supervisor.
  2. They need to stick to the duties outlined in their job description.
  3. There will be consequences if they continue to step outside their role. Be specific.

Your goal should be to eliminate all ambiguity. Once you’re sure you’ve been clear with them, any persisting deviant behavior will clearly be grounds for dismissal.

How I actually handled it

As the parent of four kids, believe me when I say I’ve heard, “You’re not the boss of me!” more than once. I don’t like hearing that from my kids, but I like it even less when I hear basically it in the workplace.

Rick worked hard to familiarize himself with every part of our team’s business – he was competent, hard-working and responsible.

He was also a know-it-all with less than perfect emotional intelligence.

It wasn’t long before Rick started telling people what to do in a bossy and authoritarian way. I noticed that some of our staff began to resist him, and that even when had something to say that was crucial to our success people tuned out his message simply because they were sick of listening to the messenger.

When I met with Rick, I complimented him for the areas of strength he was bringing to our team. I thanked him for stepping up in areas where he was not specifically responsible. I then asked him what he thought responsibilities were. Not surprisingly, he listed off several things that were clearly not his responsibility. He also vented some frustration about others, “not doing their fair share”.

Because Rick was sensitive to criticism, instead of slapping his hand I started by letting him know how critically important it was for him to prioritize the responsibilities I had given him. I outlined how important those tasks were to our team and to me personally. I explained that taking on more responsibility than I had given him was causing some confusion and that he needed to let me handle keeping others accountable for their tasks. I also owned that I had not been clear about certain responsibilities and that I didn’t want his reputation tarnished because he was trying to help the team.

The most important thing for Rick to hear from me was that he was a critical piece to our team’s success and that he didn’t need to extend his scope to be recognized as a key player. He seemed to understand that he wasn’t helping himself by over-stepping his boundaries, and I saw significant growth in this area as a result of our conversation.

8. When one of my employees undermines my authority…

No matter how confident you are, it’s never easy to hear that one of your employees has been undermining your authority. As their manager, you want respect. But this employee doesn’t take you seriously—and they’re getting away with it.

They could be…

  • Going above your head
  • Badmouthing you to their coworkers
  • Exaggerating your blunders
  • Challenging the ideas and plans you present

It could be any number of other unpleasant and unkind things, and this can kill the culture of your team.

Still, it’s actually best not to confront them immediately when you find out. Let’s look at a good process to take care of the problem without everything spinning out of control.

Document it

First make sure what you perceive lines up with reality and that you can document it.

And then document it.

Talk to people who have been affected by your employee’s undermining. Find witnesses who are willing to come forward. If your manager or someone above you brought it to your attention, ask for specifics. Explain that you’d like to deal with this quickly and efficiently.

Your goal should be to have as much unbiased evidence of the behavior as possible. Employees who undermine their managers rarely own up to it right away.

If you discover along the way that they’re not undermining you, let it go. For example, are they merely sharing ideas in a communication style different than you’re used to? Just buck up and accept it. Often, letting them know you hear their ideas is enough to get them to calm down.

Confront them

Okay, so you have some objective evidence of their behavior. It’s time to meet with your employee one-on-one to talk about their behavior.

Start by sharing the evidence you have. Don’t start with questions. That just opens the door for a bait and switch.

After you’ve told them what you’ve seen, heard and documented, ask them to respond.

In this case, it’s best to be blunt; simply ask them outright why they’re undermining you. Don’t worry about being nice. You’re reasserting your authority—not making friends.

Try something like this:

“I’d like to know why you feel the need to undermine my authority with your coworkers. Is there a reason you’re going above my head rather than bringing your feedback about my management style directly to me?”

By being open to their critical feedback, you’ll set a standard of professionalism and transparency which you will then be able to ask for in return.

If your employee continues or doesn’t own up to their behavior, it’s time to transfer them. Either move them to a different department or transition them out of the company

How I actually handled it

Even I find this one hard to believe, and I lived it!

Bill was an important part of our team, but he was a maverick. If there was an unconventional way to do anything, he did it. If there was an unorthodox way to express a thought, he expressed it. Unfortunately he was also emotionally immature, which ended up causing some serious problems.

The team I was leading needed to work remotely for about 4 weeks each year, and it was important for each person to take personal responsibility for their productivity during our time away. Before everyone left, I gently made it clear what was expected and reminded them that this was a time to focus, not for watching Netflix.

About 3 weeks after the team came back together, I met with each staff member for their annual review. One of the women on my team asked me, “What are you planning on doing about Bill’s trip?”

Bill’s trip?

Apparently Bill took the 4 weeks we were working remotely and decided to have a vacation. In London.

When he came back, he shared the pictures of his trip with everyone on our team but me, which could have been a coincidence, except that he even took great care to not show my my fiancée!

Bill was extraordinarily insecure, and his behavior was troubling from the very beginning, and by the time I got a clue, Bill had not only undermined my authority; he managed to alienate most the members of our team. In fact, I would say some of his behavior even bordered on sexual harassment.

A friend once told me that one of his jobs as a leader was akin to the job of a shepherd. He needed to determine whether a difficult employee was “a wolf, or a sheep with sharp teeth”. If the employee is a sheep with sharp teeth, take it to the dentist and get them removed. In other words, do the hard work of telling them the truth and bringing them into the fold of your culture.

When a shepherd encounters a wolf, he doesn’t negotiate with it or try to shoo it away. He kills it. When you have a wolf on your team, don’t hesitate. Fire them.

I didn’t, and it’s a decision I regret it to this day.

9. When one of my employees is visibly manipulating company politics…

I don’t know if there’s such a thing as an office free from company politics.

There’s always someone trying to climb the corporate ladder by:

  • Gossiping
  • Undermining
  • Lying
  • “Brown-nosing”
  • Blaming others

It’s a sad reality that people will do they think will help them get ahead, and it’s something we often have to tolerate. But what about when an employee goes too far?

Write it down

If you’re going to do something about their behavior, you need objective evidence. When they openly work office politics, document it.

When one of your other employees brings it up, write it down.

And make sure you investigate any claims coming from third parties; Their coworkers might be the ones playing the field.

Find out their motivations

Assuming office politics don’t drive your organization, you need to find out why your employee thinks they need politics to get ahead. What made them think simply working hard and being a good team member wouldn’t work?

Here are some questions you could ask:

  • “What are your ambitions?”
  • “Where do you see yourself in five years?”
  • “How do you want your coworkers to perceive you?”
  • “What makes you want to come to work each day?”

Your goal is to get them to be honest about their behavior.

If your employee isn’t opening up, try sharing something honest about yourself. I’ve found that people often repay vulnerability with their own vulnerability. Share about a time when you thought you needed office politics to get ahead, or a time when you were frustrated with a coworker or manager and reacted similarly to the way they’ve been acting.

Let your employee see your humanity and they’ll let you see theirs.

Explain how they’re hurting themselves

After they’ve opened up about why they’re engaging in office politics, tell them why it isn’t working.

Describe the steps you think will help them meet their goals and outline how their behavior is hindering their progress. Be specific.

Help them understand that trust is the bedrock of any team, and that their behavior not only erodes team trust of the entire team; it also erodes the trust their team has in them.

As a leader, I can tell you that any time I’m feeling manipulated, it has the exact opposite effect the manipulator wants it to have. You have to make that clear to them.

How I actually handled it

There’s a proverb that states, “The first speech in a court case is always seems right until the cross-examination starts.”  Sounds like truth, doesn’t it? ? One of your staff tells you how someone else has messed up, and when you confront the offender, they tell you a completely different story!

By and large I have worked with great people who have taken responsibility for their failures, but Janet just couldn’t do it. She was a professional victim, and to ensure she was never blamed for failure she made sure she was always the first person to tell the story. Remember “the first speech in a court case is always convincing”? Well she made that principle work for her– for a while.

Eventually however, our leadership team began to see the pattern, and we asked her supervisor to address it.

Naturally, Janet had an explanation for every scenario she was confronted with. It was someone else’s fault every time, and she always had a justifiable reason for being the first to bring it up – she was just being conscientious!

So Janet’s supervisor changed the rules, and that seemed to help her. Whenever she had something to share about a failed project or about an obstacle she was facing, she was asked to bring others from her team to the meeting. Then her supervisor would ask probing questions that eventually got to the bottom of the story.

As is true in most cases, Janet didn’t realize that her behavior had the opposite effect intended. Instead of saving face, playing the political game actually hurt her reputation with leadership, and lost the trust of her team. The plan her supervisor executed did help, but sadly,Janet never regained the trust of her team.

10. When one of my employees just isn’t a good fit on our team…

First things first. Don’t mistake a poor team fit for a poor culture fit.

In the case of the former, you have an employee who isn’t meshing as well with their coworkers as you thought they would. But in the case of the latter, you have an employee who isn’t adding value because their priorities don’t align with company priorities.

Resist the urge to fire employees just because they’re not meshing with your team. If they’re still meeting expectations, just focus on helping them feel like a part of the team instead of dismissing them. Different opinions and ways of approaching problems can be a great push for teams that have too many similar voices.

Here are a few ways to help an employee get integrated and feel connected to their team.

Affirm their value

Is your employee excluding themselves from the team simply because they don’t feel comfortable yet?

Make sure your employee knows that you are happy you hired them. Affirm the value they add to the team in private and in public, when appropriate.

Highlight the ways they push their team to be better. Praise them for speaking up in meetings. Encourage them to keep up the good work.

When your employee feels confident in their value, they’ll feel more comfortable asserting themselves as part of the team.

Encourage their coworkers to be inclusive

Choose a couple seasoned team members who you know are good at reaching out to people and explain that you’re concerned your employee isn’t feeling like a part of the team. Having someone on your employee’s level reach out to them can be better than trying to facilitate something yourself.

Find out what’s holding them back

If you’re not seeing improvement after they’ve been encouraged and received inclusivity efforts from their coworkers, meet with them one-on-one.

Have a frank conversation where you lay out what you see as the problem, what you’ve done to fix it, and how their reactions haven’t been what you expected.

Your aim should be to find out whether or not they also think they’re not meshing with the team and what they’re prepared to do about it.

If your employee is a good company fit but not a good team fit, maybe they’d be happier in another department. But if they’re happy with their relationships on the team, you might need to revise your ideas of what a good team fit looks like.

How I actually handled it

When I was in high school I was forced to read “The Peter Principle” (which I highly recommend). In the book, Laurence Peter suggests that each person in an established organization rises to their level of incompetence, then generally stays there. If you’re a great lieutenant you get promoted to captain. If you excel at being a captain you get promoted to major. But if you we a lousy major they won’t bust you back down to captain. They’ll keep you as a lousy major, and you will have risen to your level of incompetence.

This happens in every organization and is even more difficult is when you have a growing company. A competent administrator in a company with 50 employees might be utterly incompetent in a company of 1000.

The culture of our Executive Team was relational, and in that sense J.D. was a perfect fit. As an HR rep, she genuinely cared for each member of the team and was quite insightful, understanding our staff well. When we were small, I often depended on her insights when making personnel decisions, and because we were in growth mode, I needed those insights regularly.

However, as our company grew we needed different insights, and J.D. would take a great deal of time in our meetings to talk about things that were more granular and less relevant to the types of decisions we were making. Her insights were still valuable, they just didn’t fit the context of our executive team.

When I initially met with J.D. I explained the problem and asked her to confine her comments and input to more universally relevant topics. I regularly made myself available to hear her concerns, but for some reason she just couldn’t make the transition. The other members of the team appreciated J.D., but they felt the same tension of “one of these things is not like the others”.

Eventually I had to make a hard call; I asked J.D. to step off of our leadership team, and I replaced her with someone who brought similar insights to the team without the issues we faced with her.

Predictably, she saw this as a demotion, and I guess it was. But over time, as she and I continued to meet together and I continued to ask her for specific insight, she embraced he role as an “ad-hoc” member of the leadership team. While she didn’t have a voice into every issue, she knew she was having an influence on our corporate culture and on the lives of our individual staff. She continued to like her job!

Let’s wrap it up

In 2015, the millennial generation (those between the ages of 18-34) became the largest segment of the American workforce. While these newly-minted professionals have been maligned in the media, it’s been my experience that, when properly motivated and trained by leadership, they are generally energetic, creative and passionate about their work. But there’s one thing they don’t have:


This blog post and the others in this series focus on how to help employees navigate in the workplace, a workplace that is often new to them. By taking time to help them walk through the process, you not only helping your business;you’re helping build the next-generation workforce we all want and need. So let’s work together using these principles, and make it happen!

Disclaimer: The purpose of this blog is to inform and inspire, but should not be considered legal advice. We’re not lawyers, just business people trying to share what we know! 

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