Prepare for the conversation as well, think about what you want to say and how you want to say it. It’s also important to anticipate potential responses, so you’re not caught off guard during the conversation.
Practice active listening and understand the other person’s point of view and finally, find support or someone to coach you to give you the confidence to tackle the conversation.
Kathy (host):
Well, hello there, and welcome back to another episode of “Help! My Business is Growing,” a podcast where we explore how to grow and build a healthy, sustainable business. I’m your host, Kathy Svetina.
Kathy (host):
As a business owner, there will be times when you need to have difficult conversations, whether with your employees, clients, or customers. These conversations can be stressful and uncomfortable. Let’s face it, it’s easy to procrastinate and avoid having these talks, pretending everything is fine. But the problem arises when you keep putting them off, as it can lead to even bigger problems for the business down the line. So, the question here is: how do you make these conversations easier on yourself and the people you need to talk to? How can you make them less intimidating and more productive?
Kathy (host):
A quick reminder: all the episodes on this podcast, including this one, come with timestamps for topics we discuss, and each one has its own blog post. You can find all the links and detailed topics in the show notes for this episode.
Kathy (host):
My guest today is Sheila Lambert. She is the president and founder of Lambert Leadership Coaching. With over 30 years of experience as a therapist and executive coach, she has empowered thousands of women to advance in their careers and be at the forefront of their companies through self-discovery. Sheila is a licensed counselor, a certified workplace wellness professional, and a stress mastery coach. She is also a speaker and a leader’s advocate. Additionally, she supports and donates a percentage of her business proceeds to many nonprofit organizations, especially the Dana Farber Cancer Institute, as she has had many people in her life succumb to cancer. Join us.
Kathy (host):
Welcome to the show, Sheila.
Sheila (guest):
Thank you so much, Kathy, I’m so happy to be here.
Kathy (host):
Thanks so much for being here. It’s going to be a great conversation. We’ve covered this particular topic on the podcast before, but I wanted to delve deeper because we’ll be discussing how to have difficult conversations with employees and clients. This is a conversation that many of us tend to avoid due to fear of confrontations or uncertainty about how to approach it. Sometimes we even witness people sticking their heads in the sand, hoping that the issue will simply go away. However, it never does, obviously. It feels like you’re trying to cross a rickety bridge over rushing water. But you know that you have to do it to reach the other side, even though it’s incredibly uncomfortable.
Kathy (host):
But it’s super, super uncomfortable. So what we’re going to be focusing on this episode is like, how do we make this easier. And I think the way to make it easier is to at least what I’ve seen for myself is to prepare yourself for it at least. But how should you prepare yourself? Because you know, the several conversations could be nerve-wracking, even if you’ve done them before.
Sheila (guest):
That is the million-dollar question, Kathy. And it is something that is really the preparation for conversation is actually the most important part of a conversation. The actual conversation is important, but the preparation for it, as you said, is ultra-important. And so I have so much to say about that.
Sheila (guest):
The first and foremost thing I want to say is that there are different types of conversations. So it’s also important to be able to pause and say what kind of a conversation: Do I anticipate entering? Is this conversation about me? Is it about the other person? Or is it actually about a situation? So when I’m thinking about me, so preparing myself for things like what did I say, that might have brought me to this conflict? That brings me to having to have this difficult conversation. And then what did I mean? Or what could have the other person meant? So the type of conversation for myself? It’s really kind of digging deep into what’s going on in my mind. Am I telling myself any stories? Is this real? Is it not real? So, you know, I think I just want to start with that part of it. Does that make sense?
Kathy (host):
Yeah, it does, actually. Because there’s so many times that I’ve noticed too, you have this one story in your head, what might be happening, but when you actually start having the conversation and you’re listening to the other person, you realize that what you thought is actually completely the opposite of what is going in the other person’s mind. And you also talked about the particular situation so there’s it’s almost going to be root of the cause of what is causing this uncomfortable situation. But what are some of the you said you the story in your head could be one of them. But how about the other person in the situation? Can we unpack that a little bit more?
Sheila (guest):
Yes, and I think the preparing in my mind is part of unpacking it. So, I think setting that stage for what is going on inside of me and what do I need to leave at the door so that I can then focus on the other person, right? That’s really important because the stories can then move on, and we’re suddenly coming up with what the other person might be saying back to us, haven’t even entered the door yet, right? I know, for myself, I’ve done that a lot of times, and my clients, they share stories where they’ve done that before. So, setting that stage and being clear on what do I need to leave behind in order to understand who this person is?
Sheila (guest):
And I might not even be getting to your answer, Kathy. And I know we’ll kind of dig deeper. But I think some of the other preparation is, who is this other person? Why is it that I’m anticipating there to be a difficult conversation? Again, it could have been a previous conversation that erupted or progressed into conflict, or it could be my own stuff that’s getting in the way and thinking it’s going to be a difficult conversation. But being able to try and understand where this other person either came from or who this other person is that I have to make sure I accommodate, right, instead of treating the person behind the door I’m about to enter as the same person that I always have a conversation with.
Sheila (guest):
So, in thinking about an individual where maybe there was a conflict and I’ll prepare or there was an issue, and I’m preparing for that difficult conversation, pick one of the things that I have found to be real important is to be able to ask myself, could something else be going on with this person? Now, I might not know it. But if we work with each other and if it’s someone that is being managed by the individual or that as a teammate or manager for that matter, so it could be on the same level up or down? Normally, we know who the person typically is or how they show up? So if there’s a change, is the change because of me? Or is the change maybe because there’s something else going on? And that I need to try and understand that before jumping right into the conversation.
Kathy (host):
That makes sense, and you know, I always like to bring those down to very specific levels. Because I think it’d be a lot easier if we come up with an example, like a real-life example where someone needs to have a difficult conversation. And do you have any examples like that when a client of yours, or maybe you had it where you had to have a difficult conversation? But can you walk us through, like, what were some of the preparations that you had or the client had to do, and how did that affect the conversation itself?
Sheila (guest):
Yes, there are so many examples that come to my mind. Let me share with you a past client that I’ve worked with for many years. This individual, this woman, was advancing in her career and was struggling with a change in her upper manager or vice president, I should say. And so she was doing so well in her work, advancing and having large teams. And then this new person came in, and suddenly she was finding herself having these roadblocks of not feeling heard, not getting validated, and not being able to execute on recommendations. So, you know, there was this internal conflict she was having.
Sheila (guest):
And so we worked on preparing for the ultimate conversation, meaning it has been a long period of time that I’ve been reporting to you. So it’s time now to have the conversation. One of the things that she had to really do some work on, which is a step in having a difficult conversation, is those stories I mentioned earlier. She had to put them in their place. She had to identify what was really happening and why she was really being questioned. Why was she feeling she was not being validated? Was that real? And let go of the saboteur thinking.
Sheila (guest):
Because what was happening was that she was starting to think, “I just don’t think I can be here anymore.” So she went from this great tenure as an employee and as a leader. And then this one change really created self-doubt, and the self-doubt perpetuated and lived in her head, which I think really got in the way of her understanding her manager. Once she was able to set the stage first through some work and then devise a plan, she went in with confidence and actual examples of questions. She was able to execute a really good conversation.
Sheila (guest):
I remember her saying, “I suddenly felt like this person that I was reporting to was human.” Right? She was no longer my boss; she was a human being. Once I asked some really open-ended powerful questions to her, which we prepared for, her manager was able to say, “Oh, wow, I didn’t realize that was what you were feeling. And the reason why I manage this way is because of XYZ.” Suddenly, the power differential that my client was feeling and creating a little bit of herself became more normalized. And when that happened, there was a shift in trust, there was a shift in openness. She didn’t expect to hear everything she wanted to hear, but she knew she wanted to open up that conversation.
Sheila (guest):
For her, that was really helpful. And I find that to be really common. Once we can get the stories out, rewire our self-doubt, and prepare enough of the conversation with tactical tools, and feel armed like going into a meeting with the questions in front of me and the things I need to let go behind me, and just some breathing and really some presence in active listening, that’s where the magic begins to happen.
Kathy (host):
This is interesting because when I work with business owners, they’re on the opposite side of this, where they are the person that the employee has an issue with. And a lot of times, it’s because the employee is reluctant about the changes happening in the business. So it’s good to hear the other side of how the employee might be feeling and how they’re processing this in their head. The question that I have here is, let’s say that you do have an employee who feels this way and you are the manager. And you know, you see the signs. The person is being required in the meetings or meetings, and either they’re feeling more resentful. There’s just something, usually what I’ve noticed is there’s nothing that you can put your finger on, what exactly it is. It’s just this general energy, vibe, and feeling that they that you have with the person. Yes, is there anything as a manager, as a business owner, if you have an employee like that, that you know is struggling or you have a feeling that is struggling? Is there anything that you can do to make this easier for them or coach them or guide them to have that conversation with you?
Sheila (guest):
Absolutely. The most important thing is not to ignore it, Kathy. So many people ignore it and hope that it goes away. To your point earlier, do not ignore it. The second is to understand what, and I’m assuming then that this person is acting different, right? Yeah. So when that person acts different, there is something going on. So opening up that conversation, using similar tools, setting the stage, setting up the meetings to have private, open conversations, trying to come towards that person in a caring, compassionate way, using open-ended questions.
Sheila (guest):
“I see that there’s been a change in how you’ve been at meetings, and I just want to open up the conversation and ask if you’re okay. I’m wondering if there’s something we can talk about that I can be helpful with. Has there been a hazard, something that’s changed? Can you help me to understand that, be open about your silence?” Right? So open-ended? Careful, right? I always caution the people I work with not to go to that employer and say, “Why are you acting different?” Why can put someone on the defense? How come can make someone feel not safe?
Sheila (guest):
And really, what you described, which is part of the work I do with leaders, with organizations, with business owners, is working on creating psychologically safe cultures. And when there’s a change, similar to what you described, sometimes the person, the employee, or the team is feeling unsafe, is feeling like they can’t speak up for some reason. And sometimes it’s the business owner or it’s the leader who’s causing that, and sometimes it’s not.
Sheila (guest):
So the signs are important to look at and actually see. Some people have the obstacle. They put obstacles in their way or they don’t look at the obstacles to remove, and those obstacles sometimes are time-related. It’s easy. And so therefore, the busyness gets in the way of really looking at the employee and the behavior change. So I say, don’t ignore it. Look at what’s happening around the environment. Look at yourself as a business owner and as a leader and say, “What am I doing, if anything, to create this shift in culture? What do I need to look at within myself?”
Sheila (guest):
And then have that really good, even conversation using some powerful open-ended questions to engage and figure it out.
Kathy (host):
Yeah, and I would say also the busyness, it’s sometimes can be a pretense of avoidance. You know, there’s a problem and you’re constantly busy. But that busy is a very convenient excuse to just run away and avoid the situation. Because no, not this week, not this week, not this week. And before you know it, a month has come by and you still haven’t had the conversation. But we’ve talked about if the employee is a little bit avoidant as well and is starting to be more distant. But what about if you have an employee who is more open up and verbal about the stuff that they don’t like, and they’re actually being argumentative and argumentative in front of your team and other people? I’ve seen that as well, especially because, again, the companies I’ve worked with, they go through a lot of changes, and not everyone’s going to be on the same page with you. And you might get into a situation when you are communicating that to the team in a meeting, and then you have one person that is completely closed off and starts to argue with you in front of the team. How do you handle that?
Sheila (guest):
Hmm, that’s a great question. What an uncomfortable position for everyone. Really, I’ve been there before, from all different angles, to be honest with you. I think as part of setting the stage or setting the tone in meetings, there needs to be some ground rules. So if it’s an established team meeting or a new team meeting, it’s always good to re-establish what the ground rules of the meeting are. We’re here to have open conversations, the expectation of the team is to respect people’s differences. It’s okay to disagree. Here are the ways that, as your team leader, I want us to agree on as far as how we’re going to disagree. So I think setting the stage and sometimes that’s done in quarterly or annual or semiannual retreats, where there’s real business planning and team building. I oftentimes encourage teams when they bring me in to do retreats to have their business items, including things like that before actual retreat stuff.
Sheila (guest):
But I think setting the stage and having the conversations about what the meetings need to look like are important. So that’s the first thing. I’m all about setting the stage, Kathy, can you tell? And then providing? Yes. And then after that, when things bubble, it’s okay to allow it to bubble to a degree. But as the leader, right, the leader really needs to be the one in charge, not to close it down at certain points, but to say, “Okay, well, it sounds like there, we really do have some differences of how we’re looking at this situation. And person, it sounds like you’re really struggling a little bit. So how can the team help talk this through? Or another tactic could be, it sounds like we’ve reached our max in working through this issue. And we’ve gotten some great feedback. And we’ve reached some crossroads. So I’d like to try and regroup right now. And this person who’s argumentative, let’s just take this offline and talk through some of the things I think you’re bringing up. I want to get back to our meeting. I want to get back to, right?”
Sheila (guest):
So there’s a way to redirect in the meeting. And then most importantly, a conversation with that person set privately around their behavior. Because we can open up a conversation, we can have our active listening, we can create a psychologically safe culture, we can allow people to have differences and identify them and name them. But when there is someone like that, it can take away all the work that the organization has done and create a culture of drama, negativity, and toxicity. And nobody wants to live in that. And that’s where organizations struggle with retention.
Kathy (host):
Yeah, I mean, it just sucks all the energy and all the oxygen out of the room. You can just feel it. And it’s very uncomfortable for the people who are in the room witnessing this as well because it’s very cringy, I will say that. It’s very cringe-worthy to be in a room where this is happening. And I’ve been in a couple of rooms like that, and just, “Just get me out of here.” So you’ve said redirecting and then having a private conversation afterward. So let’s talk a little bit about this private conversation afterward. How would that look like? Should you, as I say, not ever write an email when you’re angry? Just wait, should you wait a day or two? Maybe a week or two to address this? Or should you address it right after? Like, what is the timeframe? And how would you have that conversation? Like, how would that look like?
Sheila (guest):
I think a lot of my answer is different depending upon the person. So, is this someone who this is the first time that this has happened? I’d give it a little time, give them some space, check in with them, circle back with them. Try and engage with them that day, I think, right? For the most part, if it’s somewhere there’s been some buildup progression or ongoing, again, it depends on the person. Are there previous write-ups on that person? So there are different things to look at to determine next steps. That individual, I might then make sure HR is pulled into that conversation to come up with the right plan for next steps.
Sheila (guest):
If it’s someone that there’s a really good relationship with, and even if it’s not the first time but it’s not really a problem, and it could be relating a situation, I’d still circle back with that person fairly soon. Because what’s hard to have is for everyone leaving for that day, right, the manager and the employee. So I think managers, right, this is part of being a leader is learning, learning and getting training in the areas of when do I execute now versus when do I wait a little bit? Now, one key component is for that leader, like, I need to make sure my emotions are in check. If I’m really angry about what happened and how they derailed the meeting, having it right away might not be the right thing. I know, for me, I need some time. I need to breathe, I need to make sure my emotions are in check. And that’s where that difficult conversation comes in. And then meeting with the individual and opening it up and having some clear objectives.
Kathy (host):
Is there any common words or phrases that would make this particularly effective when you have this meeting? And I know, I’m not asking for like formulas of it. But it would be really good to have something in your back pocket that you can say, well, this is maybe how I can phrase something like this so that it’s more neutral versus negative and so that you have that objectivity. And you’re not coming, even though you might have cooled off, it could still be on when you think about that particular event. You still get angry. So is there anything that would help when you’re in that situation?
Sheila (guest):
I think non-judgmental questions at first, to try and open up the conversation and not come at the person, are important. For example, you had obvious signs that you were upset during the meeting, it was clear to myself and everyone that you were upset. Can you please help me understand where those emotions were coming from? Can you share a little bit about the position that you are feeling in there? This approach says, “Alright, I want to hear your side.” And sometimes when that happens, the other person starts coming down a little bit. Now, again, giving them space, as you mentioned earlier, might be important.
Sheila (guest):
If the person is still elevated, you can ramp up the question a little bit while still keeping it open. For example, you can say, “I understand you’re saying you have a difficult time with that. I’m really trying to engage in the conversation with you to try and help you and try to help the team. I can’t do that if you’re coming from a place of judgment. I want you to try and think about how we can have this open conversation in a productive way.” Sometimes, this approach helps the person realize that they need to shift their mindset and approach.
Sheila (guest):
If the person is still unable to have a productive conversation, the leader needs to step in and take charge. They can say, “Okay, it sounds like you’re not really at the point of being able to have this conversation. The reality is, I’m going to recommend for you to take some time and think about how you acted at that meeting and how you’re going to rectify that. And I’d like to have a follow-up meeting with you.” The leader can give the person time to calm down and come up with their position. They can suggest taking a day off or working from home to allow for reflection. Alternatively, they can schedule a meeting in a couple of days and provide the person with questions in advance to prepare for the conversation.
Sheila (guest):
It’s important for the leader to come up with three objectives for the meeting. The objectives might not necessarily be about resolving the problem immediately but could focus on understanding the individual’s perspective, ensuring they grasp the impact of their behavior, and determining next steps. Having these objectives provides structure to the conversation and helps the individual understand that their behavior needs to be addressed. At the end of the conversation, it’s important to summarize and wrap up the discussion, set the date for the next meeting, and clarify the action items or areas of improvement that need to be addressed before the next meeting.
Kathy (host):
And would you also send a summary of it in an email? Or would you just summarize it in the meeting as well?
Sheila (guest):
I think at that point, documentation is huge. Okay, and I have two reasons why I’d say yes to the documentation. One, it’s really important, right, for being able to track employee performance. And when it gets to the point of performance improvement plans, we need documentation.
Sheila (guest):
But the tune, sometimes people’s emotions get in the way of understanding and hearing from the meeting. So having a follow-up can be a good reminder and can help that visual person to get out of the emotion and into so having that structured email or follow-up at this level is important.
Sheila (guest):
Some people have already established that, right? Because when I work with people, I encourage when you’re working with a team, establish what type of communication is important as you move forward. So that might already have been established. Or if it’s not, I would definitely get that in place.
Kathy (host):
Yeah, that makes sense. And, you know, this is an interesting perspective too because now as we are working on globally, and maybe that you are working, you have remote workers, you might have, you know, some outsource staff or whatever it might be, that are not in the same culture as you. So that brings an extra layer of complexity of having these difficult conversations. So are there any cultural differences that you have to keep in mind when you’re having these difficult conversations with employees or clients from different cultures? Like, how do you handle that? I know this is a very packed question. But is there any general guidance that you can give us there?
Sheila (guest):
I don’t even know if I have all the right answers to that question. But I will tell you that I’m a true believer in at the beginning of that manager, supervisor, your supervisor, Supervisory relationship, understanding the person you’re managing, I also encourage understanding your manager. So certainly, understanding needs to be all-encompassing, not only being who is this person as an employee, but what are the factors in that person’s life that brings them to who they are. What’s important to them in their life, which includes their culture? How can I best support them in their work here, which includes their culture?
Sheila (guest):
There’s a tool that I use when I work with individual leaders, as well as organizations, individual leaders to help them have those conversations and set that stage for developing that understanding, let’s just say, and I also do this with teams when I’m working with them. But there’s clear questions that helps things like what’s most important to you? How do you want to be celebrated? What are some misperceptions that people have of you? So I think that the beginning developing of that relationship can be where a manager begins to understand those cultural differences. Especially if you know the culture is a little bit then you can we can dig deeper, what’s important to you that we you want us to celebrate for you and with you.
Sheila (guest):
And then I would also look at how to reverse that. Because, yes, we want leaders to support their teams and their individuals around their culture. And it’s important as managers and leaders to communicate what’s important to us, so that there’s a shared inclusivity shared relationship and understanding.
Kathy (host):
Yeah, and I think as a business owner myself, I think of this as the company that you own and you started and you’re working in, and you have a certain vision and you have certain values in the company, even if you have no idea what they are. There are definitely that they’re. You just have not articulated them yet enough, but they are definitely there. And I think for me, the way how I have managed that in my own business because I’ve worked a lot with people in different cultures, is by having certain guidelines that I communicate upfront. One of the biggest ones is that mistakes are okay. A, that everyone is human, we all make mistakes. And I would rather have them tell me and say, “This is what went wrong, and we can fix it together,” versus someone trying to hide it or feel bad about it or whatever it is. So that is one of the core values that I have for my business, that where human mistakes are fine, just tell me about it versus trying to hide it. And I think that’s very important to articulate those types of things, whether it’s on a company level, and how it is to work with you as an individual.
Sheila (guest):
Yeah, I love that! I love that you mentioned the word “values.” And I think what you just said, as far as how you set that stage with people, like I’m going to use because I love it so much, but the value piece is critical, right? So there are a few different levels of that. I’m glad you mentioned it. Values are what gives me joy, as you know, right? That’s why you just described what you do with your business. But values is connecting our set our values with company values is also what gives people energy, right? So I believe that understanding people and where they come from, and what’s important to them, and what their values are, is critical in setting the stage for that open dialogue and communication. And it’s also critical for businesses to have their own value statements. But then to have employees engage in that process as well. So they can understand it, feel a part of it, share their values, and see where there’s alignment for energy and motivation. So I’m adding in an extra piece that you didn’t ask for, but I think that’s kind of what was coming up for me when you share that.
Kathy (host):
Yeah, and you know, as we were talking about this, I always have a lot of mental images in my head. What I would think about these is kind of analogies. When you don’t have values and you don’t have these guidelines in the company, it feels like everyone is in a boat and everyone’s rowing in different directions. So what’s going to happen? You’re not going to get anywhere. There’s going to be a lot of issues. You’re going to be stagnating. It’s just going to be really hard to move forward. But once you have that, everyone is now rowing in the right direction, the direction that you want to go as a leader, and everyone is doing their part. Because obviously, if you’re leading the ship, you cannot be rowing as well. You’re just going to get exhausted. And as a whole, we’re overworking and overburning yourself comes out. But if you’re there, steering the ship, and then you have people rowing in the same direction, it makes it so much easier, so much better.
Sheila (guest):
That’s right, absolutely. And the piece that you mentioned, as far as setting the tone of “it’s okay to make a mistake,” right? Even making a mistake, but sharing it, “I made a mistake, I would have done it this way next time.” You’re still seeing people rowing together, right? It’s just bringing in those values of authenticity.
Kathy (host):
Yep. So Sheila, we had a really great conversation. Thank you so much for this. But I always ask this, every single guest that comes to this podcast, is I want to give someone something listeners actionable steps that they can do in the next week or two. So if someone let’s say that has a difficult conversation that they need to have, and they’re like, “I don’t really want to do this, but I know I need to do this,” what is the one thing that they can do in the next week or two, or hopefully sooner if it’s a conversation that they need to have as soon as possible, to get them to that conversation in the most productive way?
Sheila (guest):
Yeah, all in one. I think one of the most critical first steps is self-care, right? If that person doesn’t have time to rest, to take care of their human basic needs, and to put their stuff aside, it’s not going to be productive. The second is prepare, like we talked about. Then, of course, the third is active listening. Try and just prepare for that active listening. And if that’s not clear, or if that individual feels stuck, find someone to help support you – find a coach, find a friend, find a group where someone can share with you, be your mirror, you can practice with. But find somebody so that you can then be successful at that conversation, which I know everyone can be. It’s just a matter of preparing for it.
Kathy (host):
Thank you for that. So one tip, Sheila, where can people find you?
Sheila (guest):
I am on LinkedIn, Sheila Lambert, and I have my website which is Lambert Leadership Coaching. And my email is Sheila@LambertLeadershipCoaching. So in any avenue, please reach out. I’m happy to have a consultation.
Kathy (host):
Thanks so much, Sheila. I really appreciate this conversation, and I know it’s gonna be probably one of the most popular podcast episodes.
Sheila (guest):
Oh, thanks so much for having me, Kathy.
Kathy (host):
Thanks so much for joining us today, and I hope that we’ve given you some valuable tips on how you can prepare for those difficult conversations so that they become easier and more productive. It’s important not to run away from them or put your head in the sand because that is not going to serve you or the business. Also, if you love this episode, you can find all the timestamps, show notes, blog posts, and links on the website at newcastlefinance.us/podcast. And before I go, I do have a favor to ask. If you are listening to this on Apple Podcasts, could you please go to the show and tap the number of stars that you think the show deserves? This helps other people find it and gives that much-needed Apple Podcasts algorithm love so that more people can discover it. Thanks so much. Until next time!
Sheila Lambert is the President and Founder of Lambert Leadership Coaching, LLC. She brings over 30 years of experience as a therapist and Executive Coach, empowering thousands of women who advanced in their careers and are at the forefront of their companies through self-discovery.
Sheila works creatively and collaboratively with organizations to help elevate and advance their leaders. Aside from having over 450 hours of academic training and over 1700 hours in ongoing continuing education training, Sheila has an MS in Organizational Leadership and an MS in Counseling.