Having difficult conversations with employees is hard – especially when you’re managing remote teams. Here are some tips to make it easier.

For leaders who are new to virtual work environments, managing remote teams can feel especially complicated. After all, you can’t just walk down the hall to see and talk to everyone. You can’t conduct an impromptu meeting whenever you want. You can’t check in with employees on a whim. To a certain extent, the separation, distance and lack of in-person interaction can create mystery and disconnection.

Virtual work definitely adds complexity to the leadership function, but managing remote teams really isn’t all that different from managing onsite teams. Regardless of location, all managers share the same basic challenges in leading people.

One such challenge that any manager will encounter at some point is engaging in difficult conversations with employees. These types of conversations typically focus on:

  • Negative feedback about job performance
  • Negative feedback about a specific behavior
  • Disciplinary issues
  • Demotions or involuntary reassignment of roles and responsibilities

Without a doubt, engaging in difficult conversations with employees can be uncomfortable in any setting. But in an environment in which a manager and subordinate may rarely, if ever, interact in person, both parties are vulnerable to misunderstandings. Successfully navigating these difficult conversations virtually requires a higher level of emotional intelligence and more intention.

Here are some tips to overcome one of the toughest aspects of leading remote teams: engaging in difficult conversations.

Lay a positive foundation from the start

So much of what you do before a situation arises with an employee can impact the course of potentially tough conversations and their outcomes.

If you take the right actions proactively and consistently, tackling difficult conversations with employees may end up being easier than you think. At the outset of your relationship with each employee, take the time to:

  • Establish trust. You and your employees should be able to be open and transparent with each other. Your employees should view you as a coach – someone who wants to help them succeed – not as an adversary.
  • Spend time getting to know your team members. Learn their personalities, working styles and communication preferences. Engage in remote team-building activities or virtual social gatherings to build rapport and understand who your employees are on a deeper level. Find out how you can adapt your management style to best support each individual employee.
  • Set personal expectations. Talk with your employees about their roles and responsibilities, processes for carrying out their work, expected quality of their output, work hours and availability for meetings. Don’t assume that you’ve been clear in outlining your expectations – be thorough and ask your employees if there’s any confusion to clear up. This is one of the most common mistakes that managers of either remote or on-site teams make.
  • Review the company’s remote work policy. This policy should cover the company-wide requirements and expectations for working remotely – for example, the technologies that should be used, IT and cybersecurity standards, optimal working conditions, productivity standards, and rules and procedures to protect sensitive information.

You can demonstrate trust in your team by managing outcomes versus people. In other words, don’t fixate on how many hours employees are online each day or how often they check in. When employees work from home, there will always be distractions.

Instead, focus on your employees’ output – what they did well and accomplished, or what they missed or didn’t complete. In a remote work environment, you have to trust your people, because you simply can’t police them from afar.

You can also build trust with employees by owning up to your mistakes and identifying opportunities for your improvement. If an employee’s error or oversight resulted from your actions, be honest. You can say something like:

“I want to give you some feedback on a project you recently completed. To be fair, I did not properly set expectations, so let’s clarify those expectations now and see how we can approach the next project.”

  • Have a communication plan. Let employees know how you’ll communicate with them individually, including the frequency and the channel (e.g., email, messenger, phone, etc.). It’s also good to ask your employees how often they want to receive communication and feedback. Managers should communicate the minimum, but some employees may need/want more. Set aside time for team interaction as well. Overall, it’s important to communicate often.

Your team members should also know how to reach you if they have questions or concerns. Be accessible when you say you are available.

Default to using video

Video calls can be extremely helpful in managing remote teams and conducting difficult conversations virtually. A videoconference is the next best thing to an in-person meeting, enabling you and your employee to see each other’s nonverbal cues, gestures and facial expressions. It’s just more personal. That’s why you should never use email or any other form of written communication to deliver bad news to an employee unless it’s a follow-up to a verbal discussion.

A few things to keep in mind:

  • Be selective about which meetings require everyone to be on camera. Don’t wait until you need to have a critical conversation to get your employees on a video call. Engaging your employees face to face should be a regular practice. At the same time, numerous long video calls can be exhausting for team members and can lead to burnout at a faster rate than in-person meetings.
  • Use video calls to deliver both positive and negative feedback. If you only want to do a video call when you have something negative to say, your employees will dread talking to you. They’ll view you as a disciplinarian rather than a coach – and that’s not a place of influence.
  • Give employees notice that you expect them to have their cameras on. Tough conversations are already somewhat awkward, so do what you can to diffuse any additional discomfort. Letting employees know upfront that a meeting will be on camera can prevent them from being caught off guard and unprepared. It’s a simple courtesy that generates goodwill.
  • Don’t use video as a tool to micromanage employees. If you need to see your employees to confirm that they’re working and paying attention, this is a sign of a lack of trust and poor management. Instead, treat video as a strategic tool to strengthen your connection with employees during important moments.
  • Appear engaged. Maintain eye contact and don’t multitask on other projects. This tells employees that your conversation is important and has your full attention.

Be prepared

To keep your conversations with employees on topic, within time limits, calm and professional, have a plan. Winging it will undermine those objectives.

Come to any meeting with your main points in mind, backed up by specific examples. Focus your criticism on a behavior or some aspect of job performance – make sure it’s never personal and directed at the employee.

Your end goal for the conversation is to create a path forward for the employee to improve. Rather than spending too much time discussing what the employee did wrong, guide the conversation toward the solution. This should comprise the majority of the discussion.

Clearly explain the issue – then listen and ask questions

Once you’ve explained the issue as you see it, listen to your employee’s side of the story. They will appreciate the opportunity to be heard.

Find out if there’s a personal circumstance that has impacted their job performance or workplace behavior and how you can accommodate it. On the other hand, you can confirm whether the performance or behavior problem stems from a lack of knowledge or training, or confusion about expectations. Otherwise, it may simply be a disciplinary issue.

Engaging in this exercise can help you become a more empathetic leader and, together, you and your employee can work toward a mutually agreeable solution for moving forward. This collaborative listening approach reduces the likelihood that a difficult conversation will have lasting negative effects on employee engagement.

Assess what support and resources are needed

Ask the employee how you can help them improve their performance or change a behavior. What do they need from you to succeed?

Additional training or distance learning is an option.

You could also pair the employee with a mentor or a peer who they can shadow. With either a mentor or a colleague, employees can engage in periodic check-ins. From the employee’s perspective, this could be more challenging in a remote environment, especially if they’re new to the company and don’t have established relationships. Make the necessary introductions for the employee – don’t leave it to them.

Also solicit their input for how they might improve – they may suggest an idea you haven’t considered yet.

Outline next steps and follow up

Depending on the individual employee’s circumstances, clarify what the immediate next steps will be following the meeting. If this is a disciplinary issue, let them know that this conversation serves as a first step, and explain where they are in the disciplinary process. If the employee could benefit from a performance improvement plan, either work on creating a plan with the employee or ask the employee to submit a plan by a set deadline.

You may also consider increasing the frequency of one-on-one check-in meetings.

Regardless of the path forward, continue to follow up with the employee and assess whether the employee has improved.

If you notice improvement, communicate that to the employee – even if their adapted behavior or performance output constitutes a basic expectation. For example, let’s say you had observed an employee being unprepared for client meetings – but in the last few meetings, this employee has been on time and prepared for client meetings. You could say:

“I noticed you were on time and well prepared for both meetings. This is exactly what we’re looking for, so keep it up. What actions did you take to make this happen? How do you feel those meetings went for you?”

Positive reinforcement is very important. Just as employees need to hear constructive criticism to improve, they also need to hear positive feedback to stay engaged and motivated, and to understand how you view their performance.

Be sensitive to privacy

While managing a remote team, you should still be sure to be alone in an enclosed room any time you engage in a difficult conversation with an employee.

However, employees working remotely may not have a private office in their home. Often, they’re working at their kitchen table or on their living room couch. They might have their spouse or children nearby. As a courtesy, before the conversation turns toward the issue at hand, ask the employee if they’d like to continue the call elsewhere in a more private location. This can help to prevent any embarrassment.

Be flexible

You and your employee need to be able to focus on your conversation. However, when employees work remotely and the office merges with personal life, things happen. Family members show up unexpectedly. Children get sick. Pressing personal errands or emergencies can happen. If anything like this disrupts your conversation with an employee, be flexible about rescheduling meetings. Your employees will appreciate your consideration for them.

Summing it all up

Though it may feel daunting at first, managing remote teams really isn’t much different from managing on-site teams. It just requires some intentional effort on the manager’s part to set expectations, get to know them personally, build trust and practice good, regular communication. That way, when difficult conversations with employees inevitably happen, the discussion isn’t painful and won’t create lasting damage to the relationship.

When these difficult conversations happen, use video to strengthen employee connections and personalize conversations. Also come prepared, listen, ask questions, offer support, explain the next steps and follow up after the meeting has concluded. To learn more about coaching employees while maintaining positive relationships, employee enthusiasm and motivation, download our free magazine: The Insperity guide to employee engagement.

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