Tough Conversations You Need to Have When Working Remotely and How to Get Through Them

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Jen L'Estrange16

One of the most difficult things to do in a remote working relationship is effectively managing tough conversations. It's not because the fundamental steps are so different from an in-person conversation, but because the delivery is so much harder. My old adage has always been, the more difficult the conversation, the closer it needs to be. It’s why, pre-pandemic, our team always preferred to do termination and performance-related conversations in person. But then COVID upended everything. Now, effective communication for remote leadership is something we’re known for, and I’d like to share some insights into how our team manages tough conversations effectively for the organizations that we work with.

Know what you want to achieve. 

Every change management project has an overarching goal of benefits realization. It’s the supporting act to the business change that we’re trying to deliver. The same holds true for tough conversations. They’re tough because we’re going to ask someone to change something - and they’re probably not going to like it. So, before hurtling yourself into a difficult conversation, take a few minutes to write down the best and worst-case outcome for the conversation. What does good look like?

Prepare the script.

Always write out the scripts for tough conversations. It helps to ensure you cover all the key points, especially if you’re following up with legal documents, but in a remote environment, scripting is especially important. It forces you to structure the conversation and, in the event that the tech fails mid conversation, or if the person leaves the call or goes off video abruptly, a script gives you a tracking mechanism so you know exactly where you left off before the conversation stopped.

Deliver with empathy and listen actively.

As much as leaders and managers dread tough conversations, it’s harder on the receiver, especially when it’s a surprise. We try to avoid surprises through effective performance development processes, but assuming that there’s no getting around the shock of the message you’re about to deliver, communicating with empathy and kindness is essential. 

Part of demonstrating empathy is active listening. This is really hard for most people when managing a tough conversation because you’re so focused on getting your own message heard, however, it may be the most important step in the process because this is where you have an opportunity to show that you value the person, regardless of the message. Active listening also helps you pick up on cues like a change in tone of voice or cadence instead of trying to read body language, which is not an option when holding a conversation via video or phone. 

So, read your script, pause, ask them if they have questions or have feedback, and just listen. You don’t need to respond immediately to any questions, simply thank them for the information and, if appropriate, let them know when you’ll get back to them with an answer.

Make it about the issue, not the person.

Everybody screws up at some point. When I think back over my career, I can count about a dozen minor mess ups and a few really big screw ups. They were all fixable, and I’m still here and the world is still turning. The point is, if you're having a tough conversation about someone’s performance, make the conversation about the issue, not the person. In fact, you’re having the conversation because you value their work and their contribution. If you didn’t value them, they wouldn’t be there. Even if the conversation is really difficult, including compliance issues and criminal behavior, it’s still about what took place, not a value judgment of the person or people involved. 

Know when you can be flexible, and when you can’t. 

If this process began with a written goal statement, “what does good look like?”, this is where you deliver. In most tough conversations, there is some room for compromise or negotiation and it’s often the only way of getting to yes. As a leader in a remote environment, knowing where you can compromise is important - and in most cases, has to be done in advance of the conversation. 

This includes knowing when the conversation is becoming unproductive and needs to either escalate to someone else in the organization or needs to be taken off video and into the office (if that’s an option). Usually, you’ll know when the conversation has taken ‘a turn’ but it’s crucial that you pivot without creating additional drama. Keep it simple. Try: “Listen, I feel like we’ve reached an impasse” or “I feel like we’re a little stuck on this” followed by “I think I’d like to pause the conversation and pick up on it later [in the office]. Could we reschedule?” or “I think I’d feel more comfortable if we stopped the meeting here and addressed the issue with someone who can help us find the right solution. Can we reschedule?”

Remote work, and remote leadership, are skills that require discipline, process, and most of all, trust. The challenge with any tough conversation, especially in a remote workplace, is that trust is being tested. If you’re going to navigate it successfully and achieve your goal for the conversation, remember to act and react in a way that reinforces, rather than erodes, that trust.


This article reflects the views of the author and not necessarily those of Fairygodboss.

Jen L’Estrange, the founder and managing director of Red Clover, an outsource HR firm, is fanatical about helping companies clearly define their people strategies and achieve their change goals. She is committed to building a team of uniquely talented HR consultants from diverse backgrounds to provide strategic guidance to the firm’s clients. Before founding Red Clover in 2015, Jen worked with Altria, Philip Morris International, and Accenture in IT and HR leadership roles where she had the opportunity to live and work in over 10 countries. She is a subject matter expert in financially driven organizational change management and is regularly called on as a speaker on topics related to employee engagement during disruption, values-based talent management, variable compensation strategies for SMEs, and leading through change.

What’s your no. 1 piece of advice for managing tough conversations in the remote work world? Share your answer in the comments to help other Fairygodboss members!