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How to Have Tough and Courageous Conversations With Your Employees

By Conor McMahon - Jan. 1, 2023
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Being a manager is tough work. From requests for promotions, to underperforming employees, a resignation, and everything else in between. Often, it feels like “what’s next?”

No one is born to manage or lead, we all make mistakes every day and the learning curve is steep. Whilst your job as a manager is to make sure your employees know what they need to deliver and when, what if your attempts to motivate them go in one ear and out the other? “If I bring it up, what if they end up quitting?” I hear you say!

Here are some tips to help you have these tough conversations with your employees.

Key Takeaways:

  • When having a difficult conversation, make sure you provide feedback effectively.

  • Be specific about the reason for the conversation and have examples of what went wrong and avoid bringing any personal feeling into it.

  • Make sure you watch what you say and the tone of your voice because it can sway the outcome of the conversation.

How to Have Tough and Courageous Conversations With Your Employees

Why You May Not Want To Have These Conversations

Let’s take a step back and look at the reasons why you’re so worried about approaching an employee about an imminent issue:

  • You fear you’ll make them feel bad

  • You fear the consequences of the conversation

  • You fear hearing rejection

You’ll notice the word fear a total of three times there. But as the famous George Addair quote goes: “Everything you’ve ever wanted is on the other side of fear”. You’ll never truly know how things will turn out and its this fear of this unknown that sends managers into a catastrophizing spiral of every scenario that could go wrong.

You can however do your utmost to keep things in your favor. Instead of cowering away from these much-needed conversations, you should be tackling them head-on. Don’t let one bad interaction ruin your working relationships else you risk harming your reputation as a manager.

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How to Have Tough and Courageous Conversations With Your Employees

Courageous conversations are the result of overcoming this fear and the more you expose yourself to these situations the more you refine your leadership qualities. Here are our top tips to starting and finishing those courageous conversations:

  1. Be approach-ready. Let’s say you’re dropping the “no-promotion” bomb – have you gathered your reasons why the employee isn’t ready for a promotion? Or perhaps the business isn’t ready to accommodate monetarily and it’s bad news you must break?

    Plan out what you want to say and how you want to convey the message. Place yourself in your colleagues’ shoes and ask yourself – how would I take this bad news and what would trigger me?

    Practicing the conversation will numb feelings of awkwardness and help you feel more confident. Equally, don’t wait too long for the conversation to happen and be as transparent as possible. There’s nothing worse than an employee feeling like they’ve been left in the dark.

  2. Meet them on some level. Acknowledging a colleague’s point of view is half the battle. Understanding and creating action points is the other. Figure out ways you can accommodate training needs over a set period of time or creating adjustments in your office environment to help improve a noise or work-bullying issue.

    • State your team and business goals up front, work together and figure out a way to overcome shortfalls on both sides. After the conversation, thank them for their understanding and recap the conversation via email with all your action points. Remember – keep it firm yet positive. Set timely goals and regular check-ins so they know you’re there for the support. Resolve disagreements firmly and fairly.

    • People take criticism in all sorts of ways. Understanding the reason why things got heated in the first place is a fantastic place to start.

    • Unfortunately, situations like this don’t just resolve themselves and in order to retain trust and confidence from your employees, you need to focus on resolving the problem in a way that makes them feel heard and acknowledged. Give them room to ask questions and tell their side of the story, it might help you clarify what’s going wrong and help plan a way to tackle the issue head on.

    • Keep in mind that you’re both in the workplace to get the job done, not be the best of friends. Get to the very root of the problem, listen to their side of the argument and ask them how they’d like the issue resolved and work with them to come up with viable solutions to work together.

  3. Provide feedback effectively. Still a sandwich-method kind of manager? You may want to rethink your strategy. According to Harvard Business Review – the sandwich approach to feedback is highly ineffective due to its misconception of providing “balanced feedback.

    Ditch praise-criticism-praise for Evidence – Effect – Change – Continue, AKA the E2C2 method. It looks a little something like this:

    • You identify what’s gone wrong

    • You provide cold hard evidence to back up your statements

    • You explain how it’s affected the team/project at hand

    • You guide the employee on how to go about making changes to errors and ultimately how to maintain these changes in the future with continued consistency.

    This method is straight to the point, focuses on positive change and doesn’t beat around the bush. An effective leader is transparent and focuses on moving forward. Remember: trying to soften the blow by starting off with “the good news” to offset the bad delays the value of the positive feedback to follow.

  4. Be specific. There’s nothing worse than a manager that doesn’t know what they want. When bringing up issues make sure you explain yourself thoroughly. Have a list of concrete examples so the topics of conversation don’t appear random. If you can recall examples accompanied with evidence of what went wrong as well to rectify and/or prevent the issue from propping up again, your critique has a better chance of being well received.

    Get to the points quickly and don’t dwell on mistakes as this will inspire feelings of inadequacy and guilt. It’s very likely the employee knows something’s up – so put them out of their anticipation and get straight to it.

  5. Be accountable. We get it, hearing that you didn’t play the role of manager as well as you should have can be a real blow to the self-esteem.

    Maybe you weren’t around in your employee’s settling in period or you were “too busy” attending to other affairs and put them down low in your priority list. Accepting that you may have contributed to employee dissatisfaction shouldn’t be taken as a negative. This is the perfect opportunity to showcase yourself as a leader and help develop the skills they need to perform the job.

    Flustered? Make the time, have regular check-ins scheduled, stop making excuses and set an example.

  6. Watch your language. This goes back to rehearsing what you want to say. The words and phrases you use matter, regardless of how much you watch your tone. Critiquing is one side of the conversation, but you also need to convey, in words, what a positive outcome would look like and the steps you can take together to ensure that happens.

    If you’re starting a conversation about an employee’s poor performance, explain how the benefit of working on these areas can benefit their development and wider team relationships. Avoid “blame” words and ask them what their thought processes were on a task that they didn’t quite complete up to scratch. Lead by example and show with examples what it is they should be striving towards.

Having Tough Conversations With Your Employees FAQ

  1. How do you bring up difficult conversations with an employee?

    When having a difficult conversation with an employee, it’s important that you are specific. The more specific you are during the conversation the better. If the employee needs to change their behavior, not being specific about what they did was wrong and what they should do to correct it could cause miscommunication and no behavior change. Make sure that you focus on the facts and examples of the situation.

  2. How do you have a difficult conversation at work?

    When you need to have a difficult conversation at work, make sure that you set the talking points in advance and you have the conversation somewhere private. Setting talking points allows you to focus on the facts instead of letting your personal feelings do the talking. This also allows you to discuss everything you need to discuss without forgetting something.

    The conversation should also be done in private in a reliable environment. Doing it in front of other workers can cause the employee embarrassment and it is seen as unprofessional. It can also cause other employees to feel uncomfortable.

  3. How do you have a successful outcome to a difficult conversation?

    To have success with a difficult conversation, make sure that you and the other person come up with a solution together to the problem. After calmly telling the employee what they did wrong, it’s time to come up with a solution. You should ask for their view because it allows for them to engage and put their input. When you have their view, you are able to come up with a plan that is beneficial to both parties.

  4. What is the most important part of having a difficult conversation?

    The most important part of having a difficult conversation is developing and practicing effective communication. This mean that you should be using skills such as active listening, assertive speaking, asking questions, and acknowledge emotions. Without effective communication, the point of the conversation may not come across and both parties might be focused more on their emotions leading to no positive outcome of the conversation.

Conor McMahon is a writer for Zippia, with previous experience in the nonprofit, customer service, and technical support industries. He has a degree in Music Industry from Northeastern University and in his free time he plays guitar with his friends. Conor enjoys creative writing between his work doing professional content creation and technical documentation.


Conor McMahon

Conor McMahon is a writer for Zippia, with previous experience in the nonprofit, customer service, and technical support industries. He has a degree in Music Industry from Northeastern University and in his free time he plays guitar with his friends. Conor enjoys creative writing between his work doing professional content creation and technical documentation.

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