3 Worst Work-Related Conversations and How to Handle Them

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Patrice Barber

Patrice Barber, CEO of Career CNX and National Speaker

No one likes to have difficult conversations, especially at work. But sometimes, they’re unavoidable.

Let’s cover three of the worst work-related conversations you could have and how to handle them in a professional way.

You’re great but your work “Needs Improvement”.

This is a tough conversation to have, but it’s important to be honest with your team member if their work is not up to par. The best way to approach conversations where you need to give negative feedback is to start with a positive comment to set the tone. Then, focus on the specific area(s) where their work is lacking. Wrap up with agreement on a clear action plan to improve.

For example, you might say something like, “I’m really impressed with your creativity, but I’m concerned that your attention to detail is slipping. What would help you to be able to focus on the details of your assignments again?”

Listen for their response to understand the root issue, which may be lack of understanding of the original request, a perceived time constraint you didn’t impose, or external distractions that are unusual for them. 

Wrap up with “I appreciate that you have had family distractions. Would it be helpful if Jane took over for this assignment or will you be able to have a revision by the end of week?”

Be constructive

It’s important to be constructive in your feedback. Offer suggestions for how your employee can improve their work, and be clear about what you expect from them. 

For example, for someone who is new and consistently missing deadlines, you might say something like, “When I took this Project Management course, it was a game changer for me in meeting deadlines and focusing on the right priorities. I think you would benefit from the course to better organize your work and meet deadlines. The company reimburses you if you complete the full course. One of the goals you mentioned last quarter was to take on more leadership and some training to help you prepare. Would you have time next month to fit this in?”

Working with the employee to get them the training they need is one way to increase skill levels and employee engagement.

You are not "right" for our company.

If you are interviewing, explaining at least part of the reason behind your decision not to continue the process or conversation goes a long way to maintaining the company’s brand.

For example if the candidate is technically skilled and has the experience but shows up wearing a wrinkled t-shirt and jeans, you might ask about prior work settings they have been in and the dress code. There also may be extenuating reasons for the one off issue like a family issue, washer that failed,  etc. Ask questions to help discover their understanding about personal appearance, personal brand and the statement they want to make to others.

“I appreciate the time you took to plan for our interview. You have great answers to my questions. We are a fast paced company that relies on experience, a professional appearance, and business acumen. We are looking for candidates who understand the importance of demonstrating each of these three qualities at every opportunity. Based on our time together today, we are going to move forward with other candidates who have presented themselves more aligned to our professional appearance standards.”

Stay positive to shift away from the personal attack

Shifting to a positive mindset and open ended conversations allows you, as the leader, to better assess if the individual truly is not a good culture fit (e.g., your company manufactures military drones and the employee plans to work for the peace corp).

Two great questions both parties should be assessing ongoing is:

  • Am I (are they) able to continue to add value?
  • Am I (are they) aligned with the direction the team and company are going?

When you are talking with an employee who has been with the company for a while it’s vital to be honest with your employee if they’re not a good fit for your company’s culture or values. The best way to approach this conversation is to focus on the specific reasons why you feel they’re not a good fit.  

Start with respect. Remember that this is a difficult conversation for both you and your team member. Be clear about your decision, but be kind and compassionate in your delivery. 

For example, if you haven’t already, start with a discussion about their big picture “what if you could“ ….
“What if your emergency account, college savings account, and retirement accounts were all full, how would you spend your time? If you could be doing anything you want, where do you see yourself in 3 years, and how does this current position help or not help you get to that next role?   

Once you determine what motivates your team member, ask them what they think would be the best path to help them achieve the skills and gain experience needed to move toward their ideal work. 

Often personality styles that irreconcilably clash can be an underlying cause. If you have a colleague in another group with an opposite style to your own who can provide the skills and experience your team member is looking for,  propose a conversation to discuss the merits of your team member and explore options. 

Even the best interviewing doesn’t result in a great fit for your organization. Fit is sometimes difficult to ascertain through interviewing. If someone is hired and is later found out to be a bad fit, don’t just show them the door. Take the bold approach of allowing them some specific time to find a next opportunity that is a great fit starting with an open discussion about what works best for them. This isn’t always possible but it can be the approach more often when there are open conversations along the way.

Your behavior is not “appropriate”. You produce great results but your peers are struggling to get along with you in team efforts.

If your employee’s behavior is affecting their work or the work of others, you need to have a conversation. The best approach is to focus on the specific behaviors that are causing the problem. 

For example – if you would normally say: “I don’t like the way you’re speaking to Rob in that tone. Please stop. That’s not the way you talk to someone. I won’t allow it in the future. You should apologize to him.”

What you should say instead: “Hi, do you have a second to talk about what happened with Rob? I wanted to let you know that I appreciate how hard you’ve been working on meeting your engineering design deliverables this past quarter, and it hasn’t gone unnoticed. I suspect that you snapped at Rob because you really want the rest of the team to meet these targets, too. But in the future, could you approach Rob with more empathy? He’s also under immense pressure to get information from others and complete his reviews so that the whole team can meet their targets. Would you be willing to apologize to him so he feels heard?”

In concluding your conversation, you could say something like: “I am invested in your success here. Your work is great, but your people skills are holding you back.”

It’s also important to be clear about the consequences of their behavior. Let your employee know that if they continue to behave inappropriately, they will be required to take personal skills training or may be let go.

Preparing for a difficult conversation

After deciding that a difficult conversation needs to take place, start with a reflection on both your own fears about the conversation and what the other person may fear. Some examples include:

  • Fear of conflict. Many people fear conflict and a difficult work conversation can certainly be seen as a conflict. You may worry about the other person getting angry, defensive, or even hostile. If you are truly worried about your safety, prepare in advance with your leadership.
  • Fear of being disliked. No one wants to be disliked, and a difficult work conversation can sometimes lead to the other person disliking you. They may see you as being critical, harsh, or even unfair. Remember that in a professional setting, being disliked by an employee is not atypical.
  • Fear of being seen as incompetent. If the difficult work conversation is about the other person’s performance, they may worry that you’ll see them as incompetent or incapable. They may also worry that you’ll think they’re not a good fit for the job. Being specific about what you are addressing, staying positive, and having open-ended conversations can help to offset this fear. 
  • Fear of being blamed. If the difficult work conversation is about a mistake the other person made, they may worry that you’ll blame them for the mistake. They may also worry that you’ll think they’re not a good employee. If you think this is a possibility, prepare for it by having alternate solutions to handle the mistake or error in a way that focuses on moving forward rather than getting stuck in blame and shame for the past.
  • Fear of retaliation. If the difficult work conversation is about the other person’s behavior, they may worry that you’ll retaliate against them. They may also worry that you’ll make their life at work more difficult. Assure them that retaliation is not part of the equation. The outcome you are focused on is improvement and their success.

Do some research

Do some research for common interests between you. The employee has a life outside of work and you may be able to help them by relating to them.

Decide before the conversations what results you need.

  • Update skills?
  • Change behavior?

Be clear on what results are needed by when, and agree upon a plan to accomplish those outcomes.

Write your questions

Write out your questions for the employee. People cannot answer statements, so avoid making blanket declarations. Here are some ways to direct the conversation.

  • Be curious and ask about them to gain empathy
  • Listen for common ground
  • Remove the trigger words and let go of blame/shame
  • Find something good about what they are doing/saying/acting (there is always 10% you can learn from others!)
  • Be open to their options to find the way forward, not focused on your win
  • Let go of the outcome: be curious, and open to hearing their perspective

Dealing with difficult work conversations

Difficult conversations are unavoidable at work, and they can be especially tough when it comes to performance, culture fit, and behavior. However, with a positive mindset and commitment to preserve the relationship, difficult conversations can yield positive results.

If an employee isn’t performing, be specific and focus on the area(s) where the employee needs to improve.

If an employee is not a good fit for your company culture, be honest with them about why.

If an employee’s behavior is affecting their work or the work of others, address the issue directly.

By preparing for difficult conversations and following these tips, you can help ensure that employees are productive and positive.

Career CNX can help you keep in touch with your employees as well as your network by prompting you to have periodic conversations with people. These conversations are quick check-ins on how the individual is doing in 5 key areas, family, friends, health, and …work. This approach doesn’t have to get any more personal than the person is willing to share, and it opens up an empathetic two-way conversation. Managing the whole person is a great way to maintain employee engagement and help good people become great people.

To discuss challenges in your workplace and how Career CNX can assist to increase employee engagement and enhance performance, select a call time here:

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