The ultimate guide to having difficult conversations with employees
We’ve been there.
Marcus hasn’t been hitting his deadlines for the past three weeks.
Sheryl has been making negative comments about her coworkers to anyone who will listen.
Jason has been taking two hour lunches, every single day.
Looks like it’s time for a difficult conversation. *Cringe* 😬
If you’re a manager, you’re going to need to get used to managing difficult conversations once in a while. They’re a part of the job – and, unfortunately, they’re not always easy.
Michael Lopp, author and Slack’s VP of Engineering, puts it succinctly:
“On the list of leadership merit badges, ‘Successfully deliver hard news’ is one the hardest badges to acquire. It’s not just that you have news, it’s hard news. It’s an honest something the human sitting across from you does not want to hear. Not only do you need to deliver it, but you need to successfully deliver it.”
Nervous? Don’t be. Our ultimate guide to having difficult conversations with employees will help you nail these conversations every step of the way.
The above quote from Michael Lopp brings up a good point: what exactly constitutes a difficult conversation? Are they always about delivering bad news?
According to Elizabeth Freedman, Principal at executive coaching firm Bates Communications, the most challenging conversations with employees are the ones that go beyond simple fact-based discussions to touch on topics more sensitive or personal in nature – and ones that were left to fester over time.
“These are often related to performance, lack of advancement, letting people go, aspects of behavior that are more nuanced like demeanor, hygiene or attitude,” she says.
“Sometimes it is not about what you are saying, but the fact that you didn’t say something in a timely way, that you have let an issue become more pronounced. When you don’t nip things in the bud, the discussion is much harder.”
But what are the most common conversations that tend to worry managers the most? Corporate trainer and executive coach Bruce Mayhew says there are three conversations that tend to come up the most often:
- “Annual performance reviews where there is an disconnect between what the employee expects and what management are sharing.”
- “An employee missing deliverables or submitting work that is not up to expected standards/quality.”
- “An employee not exhibiting the values and policies of their workplace. This often impacts respect for their coworkers, customers and suppliers.”
While performance issues are a key component of difficult conversations, there are many other conversations that might come up as well. Research from the Chartered Management Institute, for example, identified the 10 most challenging conversations to have at work – and the list included a few less work-related topics like family relationships and health.
And depending on your management style, you mind find certain conversations much easier to address than others. You might thrive, for example, resolving a conflict between two team members, but struggle when it comes to delivering negative feedback.
“Difficult conversations can be many things to many people,” says Bruce. “The important thing is how you handle them.”
How a manager handles difficult conversations can have a huge impact on their relationship with their team. A poorly-handled conversation can erode trust, and negatively impact morale and productivity – and that means your team isn’t reaching their goals.
In a presentation for Lean In on difficult conversations, Fred Kofman, director of the Conscious Business Center at Universidad Francisco Marroquín, outlines the importance of addressessing these conversations head-on:
“It is precisely at those times that communication is most vital to achieving your goals that conversations break down most dramatically. That’s why difficult conversations are scary – the stakes are high and there is a high cost to fail, and yet that’s where failure is most likely.”
That’s why it’s so important to learn – and follow – the proper steps to having difficult conversations with your employees. In the following sections, we’ll outline what to do before, during and after your conversations to make sure your difficult conversations go as smoothly as possible.
Preparing for difficult conversations 📋
Our number one tip for prepping for a difficult conversation? Don’t wing it.
“Even if you are an experienced leader or manager, take the time to really prepare ahead of the conversation,” explains Elizabeth Freedman.
“You need to be specific, concrete and clear. Collect your facts and support what you are saying with data. If you have particularly sensitive or hot button issue, make sure you have covered your bases with HR and others key stakeholders. Think through what you are going to say and also prepare for what they might say, and questions they may ask. It’s important to think through how you will be able to control your own emotions and anticipate where they will react or feel defensive.”
In other words, don’t YOLO hard conversations (thanks to Michael Lopp for that gem).
Thinking about the logistics
An important component of a difficult conversation is figuring out what you want to say and why – but you’ll also want to take a minute to think about the when and where. Will this conversation take place during your scheduled one-on-one, or will it be a separate meeting? Is there a place in your office where you can speak privately?
To add, or not to add? 🤔
Not sure whether to add your difficult conversation to your SoapBox one-on-one meeting agenda? After all, you don’t want to blindside them, but you also don’t want them to panic. One option is to approach your employee in person and let them know you’d like to set up a meeting to discuss an issue that has come up – then add it to your agenda.
If you’re really not keen to bring it up beforehand, use your Private Notes section in your SoapBox meeting agenda to jot down talking points and potential action items beforehand – only you’ll be able to see them, and you can always transfer them over to the shared agenda later, if needed. 👇
Having a meaningful conversation
As a manager, one of your top priorities should always be having meaningful conversations with your team. And that becomes especially important when it comes to the more challenging conversations that sometimes arise.
As we’ve already discussed, the first step in having a meaningful conversation is preparation. The “Before” section above will help you ensure you have a clear idea of what you want to say, and why.
But beyond the prep work, there’s a lot you can do to ensure you’re setting yourself (and your employee!) up for success.
The power of notes
Here at SoapBox, we love taking meeting notes – we’re obsessed with it, really. But we think it’s extra-super important when it comes to the more difficult conversations managers need to have with their team once in a while.
You’ll want to refer back to the meeting later on, so be sure to jot down what was discussed, and any next steps you’ve landed on together. It will help to ensure the challenging conversation doesn’t go wasted.
Is your conversation is going badly? 😬
Worried the conversation will go off the rails without you knowing it?
Here’s the bad news: you might not know a conversation has gone badly right away. Or, it might seem to have gone poorly in the moment, but you’ll find out later your employee was just digesting the information.
“The reaction you get in the room is not necessarily the full picture of what the person is thinking and experiencing,” says Elizabeth. “Not everyone reacts visibly. Some people shut down or are not ready to process the information in the moment. It may take days or weeks to process the information.”
All the more reason to follow up afterward – but more on that later.
However, according to Bruce, there are some warning signs you can look for during the conversation to get a sense for whether an employee’s triggers (or your triggers) have been hit – a surefire sign things will go off the rails.
Look for these physical signs:
- Flushed cheeks
- A stiffer sitting position
- Sweaty palms
If you see these warning signs, it might be a good time to step back and check in with your employee. Ask how they’re feeling, and what they need from you to continue the conversation. They might even ask to pause the conversation as they process the information you’ve shared. That’s OK – just be sure to make a plan for when or how to continue the conversation.
Following up after a difficult conversation
If you talk to your employee about their dipping performance at work, but then never follow up on the conversation, did it ever really happen?
“It is important that the follow up is not to rehash the conversation, but to acknowledge the mutual accountability and actions related to the next steps discussed in the room,” explains Elizabeth. “Helping to ensure that the path forward continues to be clear is key to follow up.”
But it’s also important to follow up to check in on the employee.
“Managers need to be very thoughtful about difficult conversations because there is a lot at stake, especially if the conversation doesn’t go as planned,” she says.
“You are having a difficult conversation because you want a different outcome. The question becomes, did you get a positive change out of the conversation? If you achieved that outcome it may be yes, but if it is at the expense of something bigger – someone is no longer motivated, or they are demoralized – it may not.”
That’s it! 🎉 Hopefully this guide helps you to have more productive, meaningful conversations with your team. Remember to prepare beforehand, be engaged and present during the conversation and follow up afterward.
But most importantly, according to Elizabeth, remember to look at the bigger picture:
“Never forget that this is a relationship, and that you care about what happens beyond the conversation. Think about the greater objective, whether it is creating more success for the individual, the team, the organization. It is about making something better.”
Have better conversations with SoapBox