Working Conversations Episode 205:
Difficult Conversations in the Hybrid Workplace

Have you ever sent an email or text message that was completely misunderstood?
It happens more often than we wish it did.
In today’s hybrid work environment, people often attempt to handle difficult conversations through emails, chats, or text messages—where tone and intent can be easily lost.
Text-based communication lacks the vital social cues that help us understand intent, making it easy for misunderstandings to happen and escalate. When messages are misinterpreted, workplace relationships suffer, and productivity takes a hit.
In this episode, I explore how to navigate difficult conversations in hybrid settings with confidence and clarity. I introduce the "3 Vs" of communication—verbal, vocal, and visual—to help you communicate effectively and ensure your message is received as intended.
I also walk through a seven-step framework for approaching difficult conversations with confidence. It starts with asking if it’s a good time to talk, setting a constructive tone by finding common ground and using “and” instead of “but” to keep the discussion open and non-defensive.
This approach not only prevents conflict but also strengthens relationships and fosters a more productive work environment.
Difficult conversations are unavoidable, but when handled well, they lead to stronger teams and better outcomes. If you want to dive deeper into this topic, download the first few chapters of my book Head On: How to Approach Difficult Conversations Directly.
Â
Listen and catch the full episode here or wherever you listen to podcasts. You can also watch it and replay it on my YouTube channel, JanelAndersonPhD.
If you enjoyed this episode, don’t forget to subscribe, rate, and leave a review. Share it with a friend or colleague who’s ready to embrace the future of work!
LINKS RELATED TO THIS EPISODE:
Head On: How to Approach Difficult Conversations Directly.
Episode 5: Debunking the Myth that 93% of Communication is Nonverbal
Â
Â
EPISODE TRANSCRIPT
Hello and welcome to another episode of the Working Conversations podcast where we talk all things leadership, business, communication and the future of work. I'm your host, Dr. Janel Anderson.
Have you ever sent an email that you thought was perfectly clear only to have it completely misinterpreted? Or maybe you received a very curt teams or email message that left you wondering, are they mad at me? In a hybrid work environment where so much of our communication happens through email, text and chat, it's easy for tone and intent to get lost in translation. And when the conversation is difficult, like when you need to give constructive feedback or navigate a conflict or address a sensitive issue, these digital channels can make things even worse. In today's episode we're talking about why text only messages don't carry enough social cues for difficult conversations and how to have them more effectively in the hybrid world.
Now, a question I sometimes ask the audience during a keynote is this. How many of you have spent upwards of 20 minutes comprising a three sentence email just to get the right tone and hope the recipient doesn't misinterpret you? Pretty much all the hands in the room go up. Keep them up, I tell them and then I say, now put your hands down. If it worked, most of the hands stay up.
Now, I've addressed this topic before and I have a book on it head on how to Approach Difficult Conversations Directly. And if you haven't read the book yet, I will link up in the show Notes where you can download the first three chapters of it for free and links to of course, where you can buy it as well if you want to read the whole thing. But what I want to really stress today is that when you're having those difficult conversations, it is different in the hybrid work environment. It is absolutely different than when you have the conversations face to face. And of course, if you do have the opportunity to have the conversation face to face, I want you to. But so often in the hybrid working world, we're just not in the office on the same days, if we're in the office at all.
So I want to just bring the conversation back to why it's different and then give you some very tangible strategies for what to do in the hybrid work environment when you need to have those difficult conversations. And it really comes down to the three Vs. And if you've been following the podcast for a while, you'll know that I did a whole episode on the 3Vs, way back in episode I believe it was number five. Again, we'll link that up in the show notes too. But the three Vs are that our communication is traveling on three different channels that all begin with V, the verbal channel. This is words, acronyms, abbreviations, anything that can be written down, like the transcript of the podcast episode that I'm recording right now. The actual words would be the verbal component. Then there's the vocal channel.
This is everything we do with our voice almost as a musical instrument. Volume, pacing, intonation, inflection, tone, all of that that goes into the delivery of the message out loud. This is why sarcasm doesn't work over text message. If you've ever tried to be sarcastic, you may know that it falls flat on email or text message. Unless it's with like your spouse or your BFF who totally gets the subtleties of the message. But otherwise, sarcasm needs ride on our tone of voice. And then the third V is visual. This is eye contact, facial expression, appearance, gestures, all of that that can be seen about our message.
And if you don't have your video on in teams or Zoom, then you're losing out on the visual channel. So these three channels that all start with V, verbal, vocal, and visual, all go into delivering a message that has a lot of nuance and context and social cues to it. The more of these channels at our disposal and the more that we're using, the more opportunity that we have to imbue our message with all of the social cues that will help it land as intended. Now that's why conversations need to happen in real time, on a call, over video, or ideally, face to face. That synchronous real time communication allows for immediate clarification, real time adjustment, and most importantly, the human connection that words alone can't provide. Even if we don't have our cameras on, or even if just using the phone, we at least have that vocal channel that carries so much meaning and content. Now, when it comes to difficult conversations, vocal tone is everything. It's not just what you say, it's how you say it.
The warmth in your voice can signal understanding. A measured pause can signal thoughtfulness, or a slight shift in tone can turn a tough message into a constructive one. But when that communication happens over email, text or chat, all of that nuance disappears. The words may be there, but that emotional intent is missing. And if the person on the receiving end is likely to apply emotional intent to your message, and they are, the emotional intent that they apply often will miss the mark. And it's not their fault necessarily. This is just what the human brain does. It fills in the gaps.
They might just be in a hurry or they might be worried about something entirely different, and that mindset gets applied to the message that they just received from you. So consider this. You get a slack message or a teams message from your boss that just simply says call me when you're free. No punctuation, no emojis, just a short little sentence that can send your heart rate skyrocketing. Are you in trouble? Is there a major issue or are they just setting up a routine check in? Without vocal tone again, your brain will fill in the gaps, often assuming the worst. Now instead, imagine that your boss calls you and says, hey, I'd love to check in with you on something sometime soon. Do you have a few minutes? The words are different, yes, but it's the tone that makes the difference. A friendly, neutral tone communicates that the subject is just a conversation, not a confrontation.
Now to be fair, if you are pinging someone in advance of a difficult conversation to see when they're available, I'd also recommend that you use this type type of language like hey, I need to check. I'd love to check in with you on something instead of I need to check in with you on something even if it is on slack or teams. But again, I'm getting ahead of myself here. Again, the person on the receiving end of the message is going to fill in the gaps and they are not likely to assume positive intent if your message is terse or short. This is especially problematic when you're delivering a difficult message. If you need to give critical feedback to a colleague, say, hey, there are several errors in the file that you just sent me. If you say that over email or tat teams or slack, it come it could come across as cold or harsh or even passive aggressive. But if you say it in person over a call, you can soften it with your tone.
Hey, I wanted to give you some feedback on the file that you sent over today. There were a few errors that I caught and I wanted to go over them with you so that we don't run into get this again next time. The vocal warmth and the natural pacing of the real time conversation helps to signal that your intent is to help and not to attack. So that's why difficult conversations really do need to happen in real time, on a call, over video, or again face to face, if that's an option. Synchronous communication allows for that immediate clarification, that real time adjustment. And again, the human connection. You can hear hesitation in someone's voice when you're listening and you can ask some follow up questions to find out what's wrong. You can tell if the other person's holding back and encourage them to share more.
You can reassure, you can empathize, and you can adjust based on the cues that you're receiving in the moment. Now, difficult conversations are already challenging. Stripping away vocal tone by relying on email, text or chat makes them even harder and riskier. So the next time that you find yourself about to type out a tough message, pause and ask yourself, does this deserve real time communication? Would this be better said out loud? The probable answer is yes. Now, a quick caveat here. If you need to give critical feedback to someone that you have a strong relationship with and the situation is very matter of fact, I wouldn't necessarily call that a difficult conversation. That's just like, hey, you made a typo and I fixed it for you. Now what I'm talking about here are situations where the person might be upset, offended, or otherwise confused or could misinterpret the message that you're sharing.
Now in those conversations, vocal tone is the most important of the three V's in the conversation. And that's what we're talking about here. Vocal tone carries your positive intent, your goodwill, and your graciousness. So let me give you a recipe for the difficult conversations in the hybrid work environment. Step 1 Ask if it's an okay time to talk. This is equivalent to like swinging by someone's desk in the face to face world to see if it looks like it's a good time for them to have a conversation with you. Now, if you are co located, by all means swing by for goodness sakes to see if it looks like a good time to have the conversation. If on the other hand, you are in one physical location and they are in a different physical location, let's say both working from home or one working from the office and the other working from home, then even if you have your camera on, you still want to talk.
You still want to ask, is this a good time to have your to talk? Even if you have your camera on, you still want to ask is this a good time to talk about something important? Because you only see them in their Hollywood square, so you don't know what's happening just outside their wingspan. And if you're watching me on YouTube, you see me putting my arms outside the picture. You just can't see what's maybe three or four feet in their external environment. So you don't know if they are co working with their spouse or roommate. Or maybe they have children home from school who are privy to the conversation, they might just say, hold on a second while I close my office door, or pop in some earbuds to get some privacy. So the very first step is to ask if this is an okay time to talk. Now, for some of you, that might mean pinging the person over teams or slack to find out if this is an okay time to talk, rather than just showing up on a video call for them or showing up on the phone for them. And this would be driven by the normative behavior of your relationship with them.
If you usually ping each other on teams or slack to set up a call, then by all means do that. You just don't want to do anything alarming in that. You might let them know that time is of the essence. If time is of the essence in this call. Sometimes a difficult conversation can wait a day or two. But this is really what you want to find out is, is this a good time? When we are co located, we can easily see if somebody is upset or distracted about something that might have nothing to do with us. And then we know to wait a beat and have that conversation a little bit later. Now, one other consideration I want you to take here at this point when you're setting up the conversation is to consider whether you have cameras on or off.
If you are operating over teams or zoom or the like. Now, especially if the person is particularly emotive or takes things really hard or gets particularly uncomfortable in difficult situations, you might then suggest that they have their cameras off, or you might set it up as a phone call instead of a video call. In doing so, you're giving the opportunity for the other person to not have to watch themselves have a physical reaction to the difficult news or the difficult conversation that you're about to have with them. And again, individual mileage may vary based on how emotive people are and what this specific context is. So just give that some consideration. Some people might really be appreciative of not having to watch themselves have that difficult conversation. Okay, now imagine you've gotten their buy in, this is a good time. You're not going to have the cameras on.
Â
Or perhaps you decide that you are going to have the cameras on because you want them to see your facial expression that conveys your goodwill, your positive intent and so forth. But you've asked them to keep their camera off if they so desire. Okay, now the very first thing that you're going to do when you start speaking is you're going to start with common ground that engenders some sort of agreement. Now, when the brain is in agreement by nature, it is not defensive. There is no perceived threat, so there is nothing to defend itself from. So it might just be like this project is challenging or the deadlines on this project are a nightmare. Now, a nightmare is not necessarily a fact. It's a little bit of hyperbole, but it will still engender that agreement that we're talking about.
Now, one other way that you might begin the conversation is with something I call a sensitive. Now another way you might begin the conversation is with something that I call a sensitivity cue. A sensitivity cue lets the other person know that this is going to be an awkward conversation. It might start something like, you know, this is really awkward for me to bring up. Now what this does is it neutralizes the awkwardness and kind of spreads that awkwardness out across both parties. You knew it was going to be awkward already. You've just leveled the playing field by letting the other person know that this is going to be uncomfortable and awkward as well. Now this is especially true if it is a peer of yours and let's say you don't have direct authority over them and you really don't want to come across as micromanaging.
Obviously you don't want to say I don't want to come across as micromanaging because then you just put the idea of micromanaging in their, in their head. But you might just say this is awkward for me to bring me to bring up. Again, it just shares the uncomfortability. So you've either started with some sort of agreement or some sort of sensitivity cue that says this is awkward for me to bring up. Now you're going to share the facts of the situation. This is step three and you're going to share the facts of the situation and you're going to connect them with the word and. I call it the grand and and what and does is it keeps the agreement going between these facts. As you're building up to when we get to step four, the organizational impact when and again it keeps that agreement going and the other person is more likely to stay engaged and not get defensive or feel threatened.
When we use but or however to connect those facts together, the person is more likely to get defensive. But and however are conjunctive adverbs. And if you remember back from Schoolhouse Rock, conjunction junction, what's your function but and and connect things together. But is different from and however because it has that descriptive property. Just like however, but and however are conjunctive adverbs. They connect things together. But with that Descriptive property that suggests that what comes next is about to be different than what came before. So if you use but or however, if you had the person agreeing, agreeing, agreeing, however, all of a sudden they're not going to agree with whatever comes next.
Â
And they haven't even heard you say what comes next. And what comes next should be step four. That is the organizational impact. This is where I want you to land the tee up of that conversation. So when you land on the organizational impact, this is what it means for our customers. This is what it means for customer service, for our organization. This is what it means for our team dynamics or our interpersonal relationship. When you land on that interpersonal, when you land on that organizational dynamic, it makes it less personal again.
It makes it more about the team, about customer service, about supporting the customer, about the product. Whatever it is that the organizational impact has to do with, it's less now about the other person and more about that organizational impact. If this is in your personal life, it could be about the relationship, it could be about the family or, and so forth. Now step five, this is where you zip it and you ask the other person for their side. A lot of times all you have to do is just stop talking and the other person will know it's their turn. But you might need to prompt them and say, okay, I've shared what this looks like from my side of the situation. Now I'm really curious to hear what's going on from your perspective. And here you want to really, really listen and stay curious.
Now, I've done a few past episodes on listening and we will link those up in the show notes as well if you need a refresher on listening. But here you just really do want to stay present and refrain from judgment. You really want to hear the other person out and be open to the idea that they have information that you don't and that your job here is to listen to that information and integrate it. Now, after you've heard their side of the situation, we're on to step six. And this is where you're going to build a solution together based on what you've both shared. And this will take some back and forth, some give and take. And don't rush to an agreement to a solution, especially if it's a complicated and complex issue. Might even take multiple conversations to get to a solution.
And that's okay. Now, once you've reached some sort of solution, you want to, in step seven, set up a time to review the solution to see if it's working. You Want to put that on the calendar, that meeting to follow up on the calendar? Put it on the calendar right now, right when you come up with the solution. And maybe it's for two weeks out or a month out, whatever the right interval is. And this does three things. First, it holds the other person more accountable for doing whatever the solution is. It holds you more accountable as well, because maybe there's some part of the solution that you have to uphold as well. So that future placeholder is a reminder to change behavior for whomever needs to change behavior.
Two, if the person doesn't effectively implement the solution, or maybe they make a positive change and then they backslide. The meeting is already scheduled, so it doesn't feel punitive like, oh, Janelle's putting time on the calendar again to revisit this. Okay, the time's already there, so it's neutral. And then number three, if they do make a change, it gives you an opportunity to reinforce and acknowledge that change behavior. Because what gets acknowledged gets repeated. Now this is something that we often forget to do. We just mentally go, oh my God, I'm so glad that's fixed. Now we don't have to discuss that again.
But we miss that critical opportunity to lock in that behavior by acknowledging it. So again, you want to put that calendar invite on their calendar so that you get the opportunity to do that for all three of those reasons. Now let me give you an example of how this could go. Let's say your colleague is not pulling their weight on a project. So this is a peer to peer conversation, which quite frankly are probably the toughest ones to have if you're the boss. It's easier to have that difficult conversation downwards. It's difficult to have the difficult conversation upwards as well. But let's just say it's peer to peer.
Your colleague isn't pulling their weight on a project. Okay, so number step number one, you call or ping them, depending on what your normative behavior is. You ping them on teams or slack to say, hey, let me know when you have time to hop on a quick teams call with me. Okay, so you haven't alerted them to any danger here or anything like that. Okay, Then step two, you're going to start off with some common ground. You're going to be, you're going to say, like, hey, I know we all have a lot on our plates, especially after Tiffany's unexpected departure last month. Okay. At this point your colleague should be agreeing with you and is not defensive.
Okay, so now you're going to go into step Three. And you're going to get into the facts. Hey, the way we originally divvied up the work for this project was that I was going to be doing A, B and C and you were going to be doing D, E and F. That's not quite how it's panning out though. I seem to be doing A, B, C and most of D. Okay, so that's your fact setup. Now you're going to get into the next step, which is the organizational impact. And here you're going to say something like D really falls squarely into your area of expertise.
I want to make sure that our team is the most set up for success. So can we talk about how to get D back into your court? Okay, now we're going to go on to the next step where you're listening and here's where you carefully listen to their side of the situation, staying curious, asking for clarification, and really listening for any other details that might be useful. Now, maybe they're struggling with their workload or something outside of work, or maybe they think that you encroached on step D and took D from them. Okay, so just be open to anything and make space for them to share whatever is up for them. Now if they do share that, they feel like you took step D from them. Now, you need to make sure you manage your own defensiveness and you don't get defensive for that, you're just going to be thankful. Okay, let me give that back to you. What's the most graceful way for me to transition that back to you? Okay, now you're on to step six, the solution.
So see if you can mutually come up with a solution that you both contribute some ideas to, or if the other person offers up in a solution that's agreeable to you, like, hey, you took this off my plate, let me take it back. You just want to go with it. If they offer up a solution that works for both of you, okay, but again, there might be some give and take, there might be some back and forth here. Okay, and then step seven, you want to be gracious, thank them for their time, thank them for having this conversation and say, hey, I'm going to drop a follow up meeting on our calendar for two weeks from now just so we get a chance to revisit this and make sure what we planned out today is still working. Okay? They're not going to say no to that. And again, it gives you that chance to a, keep you both on track for committing to what you said you were going to do. But two, if one of you slips a little bit, the meeting's already there for you to get back on track. And three, if it all works, you get a chance to acknowledge both of you for resolving the situation effectively.
Okay, now, now these situations might not always be super easy to resolve, but they are never going to go away on their own. And they might take one or two more conversations to get to the bottom of it, but at least you get the ball rolling. All right, so in the Show Notes for today, we're going to link up where you can download the first few chapters of my book for free. Head on how to approach difficult conversations directly. You'll also find notes on that same page for you to buy it from my website in different places as well. So again, let me just quickly recap the six seven steps for you. Number one Ping the person to find out when's a good time to have the conversation. Number two, Start with common ground or a sensitivity cue.
Number three Share the facts that are pertinent to the situation. Number 4 Land on the organizational impact of those facts. Number 5 Listen intently and with curiosity. Number 6 See if you can mutually come up with a solution that you both can contribute to. And then number seven, put some time on the calendar to revisit the conversation to make sure everything's working all right. If you found this episode helpful, please share it with someone else who might benefit from hearing it. And again, let me double down on this idea that our vocal tone is what is most important in the hybrid work environment when we're having a difficult conversation. So until next week, my friends, keep working on what matters most and don't be afraid to have those difficult conversations.
As always, stay curious, stay informed and stay ahead of the curve. Tune in next week for another insightful exploration of the trends that are shaping our professional world. And if you learn something from this podcast or if you enjoy the content, please subscribe to my channel on YouTube, share the podcast over on your platform of choice, and follow me on social media. These are all excellent no cost ways for you to support me and my work and you'll find links to my social media over on the show notes page janelanderson.com/205 for episode 205 .
Until next time, keep thriving and keep working toward the future of work that we all want. Stay connected, stay curious and I will catch you next
CHOOSE YOUR FAVORITE WAY TO LISTEN TO THIS EPISODE: