Angela Cheng-Cimini: Mastering Difficult Conversations in HR
27 Feb 2025 · 25 min
Angela Cheng-Cimini, an HR veteran of 30 years, explains how to handle difficult workplace conversations. She emphasizes focusing on observable behaviors rather than character, holding a "meeting before the meeting" to prepare people, and sequencing accountability and coaching before mediation. She also discusses organizational courage: the willingness to speak truth to power and give honest feedback.
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Angela, thanks for joining us today.
Kwame, thank you for having me.
It is my pleasure. So how would you get us started? By telling us a little bit about yourself and what you do.
So I'm obviously not an audiophile. For our listeners just joining us, Kwame and I had a great time in the green room preparing for this. And so I'm a 30 year old career HR professional, a mom of two amazing adults, and married my college sweetheart and we love to rescue dogs. So it's a little bit about me that's amazing.
I too married my college sweetheart as well. We met in Spanish class and got married in graduate on graduation day.
Oh, that's amazing.
Been at it for a while. That's great. And can you tell the listeners a bit about your background in HR too?
So I actually studied it as an undergraduate. My dad discovered this major for me. I knew I wasn't a STEM kid and I said, well, business. So he said, well, what about this program? And it turned out to be sort of all human resources related organization, psychology, labor, history, labor, economics, some statistics in there. And I had a couple internships and I was hooked. And I actually don't think there are that many people who go to college be like, I want to grow up and be an HR person. But that was sort of what happened to me. It's my calling for sure.
Incredible. And now we're going to go into some of the difficult conversations you've had in your HR journey. And there are so many different types of tough conversations that come up. But one of the things that I'm finding people are struggling with a lot is the difficult conversation that appears kind of like a mediation where you as a leader in an organization, you have two people who are not on the same page, and then they come to you to be the adult in the room to make a decision and find peace, which is not often easy. So can you just set the stage and talk about maybe some examples of when or why this type of situation might happen and then what it is that we can do to put ourselves in a position to succeed in those conversations?
Well, certainly, I think there are times when people are just going to be oil and water. They're just fundamentally not going to enjoy each other's company. But in the work setting, there are always going to be shared objectives, goals that are in common. And if you can distill the relationship to the why are we here together? How do I help you? How do you help me? And get to brass tacks on we don't have to make small talk, we don't have to understand what each other did on the weekend, but we do have to understand that we have to be here for each other in this context. And almost always you can get people to agree that, okay, we're just going to be sort of all about business. We set some guardrails around how we behave with one another. For example, we're going to share airtime. Or in some of the most extreme cases, sometimes they just can't be left alone. And so there has to be a chaperone in the room until they have learned the skills through which they can then have conversations independently. But sometimes you need to give them a little bit of a safety net. It creates a little bit more of a burden on their managers. But sometimes you just need to do that before you can expect them to be adult on their own. But I have found that you can get people to a place where they agree on why they have come together in the first place and ask them to set aside the things about the other person that they don't like so much, whether it's how they communicate. Well, what is it that you don't like about the way I communicate? Well, I think it's brusque or I think sometimes it's curt, or sometimes you cut me off and try to identify the specific behaviors so people can take accountability for the things that they can change that help to improve the relationship. And if either party defaults on that agreement, then it becomes a completely different situation where you have to pull the person to account for not having held up their end of the contract.
Oh, there is so much to explore here. Angela, I love this because we have, we've talked about some of the origins and then we also talked about what it is that we actually do. And when you think about it from perspective of what our goal is in the conversations and then how to achieve those goals, you've made it much more manageable. Because I think a lot of times we go into these conversations and we fail because we're trying to achieve the impossible. We're not focused on the. The. The business concern where we're saying, you two are within this organization. We need to work together to make the organization better. But a lot of times we say, I need everybody to like each other.
That's right.
And that's not always realistic. And the point you brought up was really powerful. Sometimes it's just oil and water. We just don't match. We are. Our energy is just too different. And that's okay. So I think just giving people the permission to recognize that you're not always going to like the people you work with. I think just acknowledging that is powerful in and of itself.
Yeah. And it becomes a bit of a performance and business imperative. Like, y' all gotta sort this out. I'm not gonna make you like each other. But there is work to be done, and you need each other to be successful. And to the extent that you give up on that, that's going to mean very different consequences for the person who chooses to opt out.
Agreed. And one of the things you talked about is focusing on behaviors. And this is vital in these types of situations where you find yourself playing the role of quasi mediator in these situations. But it is so easy to overlook. And perhaps a way for us to really appreciate how powerful this is is to imagine the opposite. So if we don't focus on behaviors, what is it that we're focusing on that can lead us astray? And what the dangers there.
Yeah. And you have to go into those conversations assuming positive intent. So you do some prep work with each person beforehand. Right. What are the things that you bring to this relationship? What are the things you would like to see in your partner? And then you have them come together and sort of share that sort of as ground rules. So you kind of dig deep because there's a reason why the organization thinks both of you are valuable. Each of you brings something positive. So let's acknowledge that in each other and try to build on that.
That's great. Yeah. Because a lot of times we go into the conversation with negative momentum.
Absolutely.
Things are rolling in the wrong way. It's like we just have the bad vibes, and then we just feed into those bad vibes.
That's right.
Starting off the conversation with, hey, so why is it that you all hate each other? Let's talk about that. Yeah, but what you're doing first is you have to acknowledge, yeah, both of you have value and we're going to force you out of your, you know, your emotional silo right now and say, okay, I want you to force yourself to try to see the value in the other person. Let's acknowledge that and then we can build on that. And then during the conversation, we focus on the problem behaviors because if we don't, then we focus on subjective interpretations of what it is that we see of our perceptions and that can be led astray. Our perceptions are going to be heavily biased, rooted in our self serving biases and make and geared towards making us feel good and blaming the other side. And so focusing on those behaviors is going to be critical. But it's sometimes tough to get people out of that mindset where they just say, this person is holistically bad. There is no redeeming character. Yeah, exactly. So as you're working with them, how is it before the conversation, do you get them to drill down specifically on the behaviors itself versus their subjective interpretation of those behaviors?
Well, the behaviors are sort of what got them into trouble in the first place. So they're usually pretty quick to rattle off the things they don't like in the other person. The harder work is getting them to recognize the things that the other sees in themselves and then taking some measure of accountability. Right. I think to your point, we have a tendency to inflate some of the things that we don't like about the other person. And so how do we dial that back a little bit to be more reasonable? So it's a place where I can actually digest that. If you just say, well, you're a horrible person, then I'm just going to outright reject that. But if I say, when you show up late, that's really irritating to me because it signals to me that you don't respect my time. So that's a bit that I can recognize, that's a bit that I can own. So if you can atomize it, it also turns down the temperature in those conversations and it gives the person something actionable to work.
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This is great, Angela, because even with that example, the way that you articulated it is less triggering to the other side. And I think it's important to recognize that there is no way for us to deliver these messages in a way that it doesn't have some kind of psychological impact.
Yes.
And liberating ourselves from the need to sugarcoat things to the point of making everything palatable allows us to actually speak with clarity and recognize that I'm going to do the very best I can to be as respectful as possible and recognize that the other person has agency and autonomy. I can't control their emotions. That's really up to them. That's. That's really important. But when it comes to this, there's an element that you brought up earlier when it comes to sequencing these conversations and creating a process. Sounds like you're talking to them a little bit beforehand too, before we actually get into the conversation. What part of the conversation are you handling beforehand versus what before the actual conversation where both of them are together and then what are you actually having doing when they're actually in your presence and you're all communicating together?
A lot of times I find that the friction comes from one side or both sides not feeling like they've been hurt. So I want to give them some space to sort of process. So the meeting before the meeting is tell me what you're experiencing, what's your perspective on how this whole thing unravels and give them a chance to express what they're experiencing. And I can do some validation or I can say, actually, is it possible that this is actually how it went down, but that your lens has maybe gotten a little bit out of focus? Just give them some again, give them a chance to process, to do some reflection before you send them hot into that conversation. Have them do some homework because it is part of their responsibility in making that relationship. It's not all on the other person.
That's powerful because it's not just not all on the other person, but it's also not all on you as the HR leader or acto mediator. Right. And a lot of times people are not willing to take that ownership.
So.
So when we're thinking about the solution to this problem, the challenge that we're all experiencing collectively, it's really important to focus on that ownership aspect and accountability. Everybody is going to have some level of accountability in this. And that's not to say there's not a difference between right and wrong, because sometimes we get here because somebody did something flagrantly wrong.
That's right.
Right. But in the rehabilitation process and in the process of just rehabbing this relations, in particular, the person who has been wronged also has some responsibility in terms of what we have to do to get back on track. And that's hard for the person to accept too, especially when it's a situation where they are on. They could be perceived as the victim or might perceive themselves as a victim. So how do you speak to the accountability side for somebody who truly believes that they are not accountable for the situation that they find themselves in?
And that's where a skilled mediator really shows their value. Right. Is how they hold up the mirror. To say sort of as unobjectively as I can, this is impure through the behaviors. I see. These are the words you chose to use. And let me help define for you why those words were emotionally triggered, why they were hurtful, why they were disrespectful. And it may be that that person may never come to realize it, in which case the relationship is far more broken than maybe can even be fixed. Right. So one of the things we talk about where I work is that we're a continuous learning organization. And that's not unique to us. A lot of organizations strive to be that. And that means that we are willing to think about how we show up for one another, how we have failed one another, how we celebrate one another. And if there is someone who flat out refuses to even possibly entertain that, there could be another version of the story that's running astray of our philosophy of being continuous learning. There's no perfect. Nobody gets it right all the time. I think you're right. There will be instances where we flagrantly have just screwed up. And in that case, if that person's unwilling to admit that, then it's a different problem to be solved. That's probably not mediation.
Yes. And I think that's crucial to understand because there are some situations where mediation is an appropriate response to this. And there are some situations where it actually is very, very flagrantly inappropriate to use mediation in this situation. And it sounds like. And I want you to tell me what you think about this angle too, because it sounds like sometimes you as A leader might have to have a difficult conversation where the hope is that we can graduate to a mediation. Because let's say somebody might say, might do or say something that is incredibly problematic. Another person, the organization comes to you and says, hey, you don't know this, but this person said or did something that was incredibly problematic. And so before we get to the point of mediating and bringing those people back together, we have to address that person and that behavior first.
Yes.
And then we'll determine what we do next. Because whether or not we have a subsequent conversation may depend entirely on how the person handles that initial conversation, where we're doing in some investigation to figure out what did or did not happen, and then giving some coaching and feedback because we might find out through that process, you know, what this person might need to go. And if they need to go, then there's no need for mediation too.
That's exactly right. That's exactly right.
Yes. This is good. This is good. And I know with the time remaining, one of the things we wanted to talk about is organizational courage. First of all, I love that term. And so let me give you the floor to just kind of lay out what that means to you and then how it manifests itself in different organizations.
For me, organizational courage is deeply embedded in the DNA and the culture of this organism, this organism that we call the organization. And it's our willingness to have hard conversations with each other, to say the emperor has no clothes, to call a spade a spade, to admit our mistakes, to hold each other to account. And I think sometimes we believe we're sparing the other person's dignity or their feelings. And so we opt out of those conversations or we do them in a way that's so opaque that the message actually never lands. And so we think we're doing someone a service, when actually we're doing them a disservice.
And I think we all can look at situations where that has occurred. And I want to go a little bit deeper into this because we can all look from the outside looking into an organization. We could say, hey, you should have stepped up and you should have had that conversation. Somebody should have done that. But then when it's us within our own organizations, we might just come up with all sorts of excuses for why it should not be us who should be speaking truth to power and having these tough conversations. So let's focus on self awareness and then what we can do to overcome these barriers. So what is it inside of ourselves that holds us back from saying what needs to be said and speaking truth to power. And then how do we overcome that?
I think it's like any. Any fear or like a lot of fears. It's. It is worse in our. In our heads than it often is in reality. So we worry about, is that person going to hate me? Is that person. Is. Am I going to suffer some sort of. Some sort of political blowback because I've spoken truth to power? It is often about a sense of self preservation. Do I put myself in harm's way because I've chosen to say something that might be unpopular or controversial? I have seen more harm done than not when we withheld really important information, particularly when it comes to making a critical decision, whether it's about a person or strategy. And I'll tell you, one of the most enlightening moments for me was a manager was struggling to give performance feedback to someone on his team. And that employee finally came to me, and she said, you know what, Angel? Just. Just give it to me straight. Does my manager think I suck at my job? And I said, well, he is struggling with your performance. And she said, well, can you give me some examples? And I said, well, it's really kind of inappropriate. She said, I know, but I'm trying to get that feedback from him, and I can't get it. So if you have information to share with me, I would really appreciate it. And so, of course, I had been involved with him and how he was going to manage the symphony, so I was able to share with her his observations. And she nodded, she understood. And you know what? Two weeks later, she resigned because she realized that this job wasn't good for her, that she could never be successful because it wasn't anything that she really felt passionate about. And if he had had just that conversation with her months ago, we would have saved everybody a lot of heartache. And it didn't turn out to be. It was difficult in the moment. But later she thanked me for the grace, for the transparency, for the candor, for the respect. And I think that's where the power of courage comes from.
Powerful. That's a great example, too. And it helps us to recognize that sometimes an outcome is inevitable and sometimes the outcome that we are trying to avoid is inevitable, and we are doing ourselves and the other person a disservice by not having the conversation and arriving to that outcome in the way that is most compassionate and effective. Yes, because if we might have had the conversation about feedback and recognized, hey, this is simply not a fit, it's not necessarily that you're doing Anything wrong or I'm doing anything wrong, this is. You're just on the wrong team, and that's okay. But let's have the conversation so we can come to that conclusion and that then actually do something about it. But we say, I'm afraid of hurting somebody's feelings. I don't want them to feel bad. And then we just act really awkward and avoid them, and they feel really bad anyways and they leave.
That's. Anyway. Yeah.
Right.
Yeah. This gave her agency, and she pivoted to something else that makes her so. Made her so much happier.
Absolutely. And I think, Angela, when we are honest with ourselves, a lot of times we say that we're doing this to spare other people's feelings, but the reality is we're doing it because we are afraid of confronting our own feelings or sparing our. Yes, yes. And it's just so important to recognize that, because at the end of the day, when we lean into that and we have those conversations, we will find ourselves in a new place where both parties are empowered with more information that both parties can use to make better decisions, too. And negotiation is an information game. And then at the end of the day, when we're having these conversations, we're sharing information, letting folks know what we want, and we're trying to see whether or not there's a way for us to move forward productively in this organization and in this relationship. And sometimes the best outcome is just a humble realization that the future is not here or with this person. And that's okay, too.
And life is too short to be stuck in bad choices.
Absolutely. I agree.
I agree.
Well, Angela, I know that we're coming up on time, and because somebody wasn't able to figure out the audio listeners, I am. I am the somebody. So it was like a guy asking for directions. I could figure it out. And then I asked Simone to come on the podcast, our executive producer, and he figured it out, you know, so lessons learned. But before you go, I know you are embracing a new chapter in your life. So can you give the listeners just a little teaser about what might be coming next?
Yeah. So 30 years in HR, and I think to do this worked really well. Kwame, you've got to show up every day willing to give every ounce of compassion and sensitivity to the work. And I was feeling my energy starting to flag, and I didn't want to get to a point where someone had to have a hard conversation with me. And so self selecting out, I'm going to take some time off. I think I'LL keep my hand in hr, but I really want to try paddleboarding. I want to try writing a book. I want to catch up to my husband, who's been retired for a number of years and spend more time with our adult children. It's scary to be sure to be walking away from a steady paycheck, but I think there's something beyond that's beckoning me. And this may just turn out to be a sabbatical and maybe I'll come back to it in a year, but I feel I owe it to myself to try something different.
Amazing. Well, we appreciate the fact that you spent some time with us to share your wisdom and listeners. Make sure to connect with Angela on LinkedIn if you would love to. Just keep in touch and keep up with the journey too. So Angela, thank you so much for joining us today. Really appreciate it.
Thank you for having me, Kwame. It's been great.
Wait, wait wait wait, wait.
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