EP 44: Navigating Difficult Conversations

Sarah Fanslau:
Welcome to THRIVERS: Impact-Driven Leadership for the Next Normal. I’m your host, Sarah Fanslau, Chief of Impact of THRIVE IMPACT. If you’re listening to this, you’re probably somebody who doesn’t just want to do nice things in the world, but you actually want to create positive change in people’s lives and not burn out while doing it. Well, how do you do that? Our mission is to redefine what’s normal for workplace leadership, to be about co-creating impact from the inside out. Burnout is the enemy of creating positive change, and we want to connect you with impact-driven leaders and ideas so that you can learn to thrive in today’s landscape.
Today, I’m joined by my co-host, Tucker Wannamaker. Hey there, Tucker.

Tucker Wannamaker:
Heyo.

Sarah Fanslau:
Co-hosting, how are you feeling?

Tucker Wannamaker:
[inaudible 00:00:52] your cohost. I love it.

Sarah Fanslau:
I know. I’m so excited. We have a really fun conversation. Well, fun, I don’t know. Hopefully, I know it will be fun. It may also be hard.

Tucker Wannamaker:
It could be a difficult conversation. [inaudible 00:01:01].

Sarah Fanslau:
It’s about difficult conversation. So Tucker, before I introduce to the guests, talk to me. How are you feeling about this conversation? What’s coming up for you?

Tucker Wannamaker:
I feel like it’s such a ripe time for talking about how to have conversations that are humane but yet also difficult. Literally, we had two organizations we’re working with right now, where earlier today, we talked about a massive pain between the board chair and the ED. We also talked about the executive director being gone, and now the board is coming in. I feel like most of our work revolves around helping people to have difficult conversations, because there’s so many difficult conversations that are needing to be had, because people are realizing things are bubbling to the surface, and it’s like, “Wait. This isn’t working anymore. Wait. Is this even worth it for me anymore?” There’s so many things like that. So I feel like it’s a really important next normal, impact-driven leadership topic to talk about, so I’m grateful it’s happening.

Sarah Fanslau:
Yeah, 100%. Well, I’m so excited to introduce our guests, and spoiler alert, I have worked with both of these humans, and they’re my favorites. So it’ll probably just be a fun chat. But first, we have Tabitha May-Tolub. She is currently the Director of Training and Partnerships with Multiplying Good. She has about 25 years experience in the youth leadership and development space. She had this amazing company called Roots & Wings that trained young people and the adults who care about them in a lot of different pieces, like leadership, communication, identity development.
Before that, she was with another awesome youth organization called Youth LEAD, training and inspiring young people to use their values and beliefs to connect with communities. She has graduate training in marriage and family counseling and holds degrees in psychology and education. And when she’s not doing all this amazing work with young people, she lives around the Boston area and has two beautiful children and a husband. And Tabitha, we’re just so lucky to have you here today.

Tabitha May-Tolub:
Thank you. I’m so excited to be here.

Sarah Fanslau:
Absolutely. And then we have Janai. Janai, I love Janai. She is a fave of mine, as is Tabitha, but Janai is currently the Senior Program Manager. She has 15 years experience of youth development experience. She right now is overseeing the New York and New Jersey chapter of Students in Action. That’s part of Multiplying good. Before joining Multiplying Good, Janai was the Youth Outreach Manager for ECPAT-USA, where she educated and empowered and mobilized young people around the issue of child-trafficking. She was also working at places like Global Kids, South Asian Youth Action and Advocacy Lab, teaching young people about social justice. Janai went to the University of Vermont and New York University for grad school, and she’s an AmeriCorps alumni.
And Janai, well, actually both Tabitha and Janai and I worked together at Multiplying Good, and Janai was like my first human I hired when I was working at Multiplying Good. And I still remember sitting in the interview room with Janai, and I was just like, “Yes, yes, if this is going to be what it is.” And she and I did so many conferences together, and just Janai, it’s great to see your face, and I’m so glad to have you here.

Janai Smith:
It’s great to see you. Thank you. I’m glad to be here. Thanks for having me.

Sarah Fanslau:
Absolutely.

Tucker Wannamaker:
I feel like in hearing both of your bios and a little bit of your background that you are experts in difficult conversations, everything from helping young people to connect across with communities and around social justice issues. I hear two people who have been deep in the trenches of how to actually host and facilitate and have difficult conversations. So I just noticed that in hearing your bios, like, “Wow, I have so much to learn here today. This will be great.”

Tabitha May-Tolub:
I would have to say that word expert makes me uncomfortable. I’m not sure anyone’s an expert on this, but I think the value of the discomfort of it, I do feel very familiar with, for sure.

Janai Smith:
Seconding that.

Sarah Fanslau:
Well, yeah, I was going to say, I think that may be a good place to start. I’d love for you to each just tell us a little bit about what is your experience with difficult conversations and what kind of brings you to think about this as a really important piece.

Janai Smith:
You can start, Tabitha.

Tabitha May-Tolub:
Yeah. The podcast’s only so long, but I would say there’s two primary things that put me in this space. One is where I grew up. I grew up in a very homogeneous town in Maine and somehow had the clarity to understand that the world didn’t look like the town I grew up in. So I spent the first year of college in a very, very diverse university, making lots of mistakes, being very, very ill-equipped, and I think that drove me to understand how important that skill set is. And I valued it and it was amazing, but it was also a really painful year. And so that kind of drove me to do this work.
And then I think one of the beauties of working with young people is that they are right there. They’re in it, and supporting them to have those conversations as a way to give them a path forward. So I think those are the two things that brought my heart to it. And then I’ve just in been many situations where wanting to think about helping myself and others navigate that.

Sarah Fanslau:
Janai, what about you? What brought you to this spot of difficult conversations?

Janai Smith:
So interestingly enough, my starting experience is kind of the inverse of Tabitha’s. So I grew up in a very diverse area, and then I went to college in a very, very white area. And so being there and experiencing tokenism, well-intended sometimes and other times not really, just really got me thinking, “This is a problem and there needs to be a conversation or multiple conversations around it.” And so really attempting, I don’t know how successfully, but to get those conversations started, even as a 17 or 18-year-old is kind of where that seed was planted.
And then to Tabitha’s point, just working with young people, the conversations have to happen. There’s so much that they need to say and so much they want to say. And sometimes there’s that difficulty of speaking to an adult about a certain topic or even speaking to your peer when you disagree. And so they’ve definitely encouraged me to even lean into that discomfort and just be in the trenches with them to have these difficult conversations.

Sarah Fanslau:
Well, I love that. I love that both of you have this kind of identity piece a little bit of around formative conversations that have brought you to this. And the three of us, just for the readers, while we were working at Multiplying Good, we did some work with the Edward M. Kennedy Institute in Boston around having difficult conversations, specifically how to help adults, because I think adults are the biggest problem here. I don’t know, you tell me. But helping adults learn how to have difficult conversations and facilitate them, so that the young people that they’re working with could really share their thoughts and their voice.
And so I’m curious, as you all think about the work you’re doing now and have done before, what are those kind of pains or issues you’re seeing come up for non-profit leaders or young people? What are the pains they’re experiencing around difficult conversations? And it could be having them facilitating whatever’s coming up for you, but what are the pains or issues you’re seeing here?

Tabitha May-Tolub:
Why don’t you kick us off this time, Janai?

Janai Smith:
Sure. I think the main one is just a fear of having these conversations. And so there’s this idea that one, maybe we’ll say the wrong thing and that everyone will look at me and think that I’m uneducated or I’m this or I’m that. And two, we do live in a cancel culture. And so again, you make one mistake sometimes, and that can blow up everything. So I think there’s a strong fear amongst our leaders to broach the topic. And then if you work, let’s say, in a non-partisan organization, it’s hard. “Well, I don’t want to come off as taking a stance against this or for this,” and what you kind of end up doing is pretending that issue doesn’t exist, which is problematic in and of itself.
So I would say that that’s really the thing that has come to mind is that there’s this deep-rooted fear of just having those conversations. And then if someone is willing to have those conversations, it’s where do we start? How do we create a space in order to do so? And there’s going to be discomfort, and people are going to be offended. Again, that still kind of boils down to fear, but it’s also uncertainty. It’s like, “Well, how do we even get this conversation started?”

Tabitha May-Tolub:
Yeah, I would echo that 1000%. That fear, I think is the biggest factor, especially in our communities right now. They’re so polarized and there’s so much tension to begin with, we’re constantly afraid of saying or doing the wrong thing or hurting people that we care about, communities that we care about. I think also, just to name it, organizations have attorneys and HR professionals that are saying, “Don’t do anything. Don’t say anything. We have a document they’re going to sign.” So I think that, although I understand they’re trying to be protective, is really, I think, can get in the way.
I also think a lot of organizations assume if difficult conversations aren’t happening, it means everything’s okay. And so they’re just like, “We don’t need to have difficult conversations because everything’s fine.” And I think we’re humans, humans are complicated. The issues we talk about are complicated. If difficult conversations aren’t coming up, it’s because people are uncomfortable or, worse, afraid to have them, not because they’re not there, and that I think is a major barrier.
I also just think we don’t teach people this, there is a skillset to have difficult conversations, and we don’t teach that, and it is against our grain. It’s against our biology, our anthropology. It’s against everything we are as humans. And so there’s no way for it to develop unless we intentionally start building these skills in our young people and our employees. So we just don’t have the skills, especially at the leadership level. It’s just not there. I think a lot of times on the ground, the direct service people, they have them because they have to.

Tucker Wannamaker:
Yeah.

Sarah Fanslau:
100%.

Tabitha May-Tolub:
But it’s not being transferred up. And even with that on the ground, if it’s not up here, eventually the culture and climate starts to implode.

Sarah Fanslau:
Tucker, curious what thoughts or reflections are coming up for you?

Tucker Wannamaker:
Yeah, I want to just get into some stories, like where, you know? It doesn’t have to be too recent. I know we joked about that at the beginning. “Over the last week, where have you …” Tabitha, I’m so curious, especially what you just said around the lack of skills too, how much of this is a how issue, and because I don’t have the skill, therefore I have the fear, how much of this could be solved with just some simple tools and some tricks? Not everything I’m assuming, of course. I was even talking to a friend of mine earlier this week of sometimes, we try to go for the heart issue, the deep-rooted issue of what’s really going on, when really maybe just a tactical how challenge of let’s just create better conditions.
We usually joke about whenever people have these big diversity, equity and inclusion conversations, and then they have a meeting the next hour of the silent majority and the vocal minority. We’re just totally missing it. There’s how to this, and I just wonder how getting into some stories of how, where has played itself out in your real lives and some of those skills that you’re talking about that could help alleviate some of these fears in a sense?

Tabitha May-Tolub:
Yeah. I think you’re right on it. I think the how, this isn’t rocket science, not really, but it is uncomfortable and it’s hard. And some of it can be taught formally, but some of it just needs to be informally messed up in safe containers where people can fail and then authentically correct and move forward. I think a lot about my freshman year of college. I say I spent a year offending everyone I met, and it wasn’t because I was a bad … I was such a good person, but I had no context for how to have difficult conversations. And so I think a lot about the head and the heart.
You can understand something intellectually about how to have a conversation or how to engage with someone who is different from you in whatever way, and that’s good. That’s a good first step, but then there’s also this heart understanding that comes later. And so I think we have to teach people the formal skills of how to have difficult conversations, and then we have to give them the containers where they can safely fail so that they can really get that heart connection and so that it becomes just an organic way of operating, as opposed to, “Oh, no. Difficult conversation. Engage, engage.” It has to get to that next level eventually, but I think that’s the hard part. So I didn’t tell you any stories, sorry.

Tucker Wannamaker:
Well, I want to hear about when have you created the container, right? I love what you’re hitting on of giving people space to learn because we already have this inherent joy in learning, and learning involves messing it up. Just like you’ve seen any child try to learn how to walk, guess what? They had to fall how many times in order to learn how to walk? And that’s how learning is. And we all want that, we have a joy in learning, but we don’t have the conditions or the containers in which to learn. And there’s a whole body of research back behind all this, but that whole concept of we’ve stolen learning away from our institutions. But I’m curious from you, how have you created a container? Tell me about a container that was there with your staff, with your team, with whatever it might be.

Tabitha May-Tolub:
Sure. Yeah, I’ll talk about Roots & Wings just because I had full control, for lack of a better word. But I think the containers, we talked about our work with Edward, Kennedy, the containers are fairly simple. I think the challenge is they need to be implemented before there’s a crisis. They need to be part of every staff meeting. They need to be part of every strategic plan. They need to be part of every one-on-one, so that is just how we operate. So when something is difficult and uncomfortable, we already have the container.
So those containers include shared goals, shared agreements about how we operate with each other. Those contain a very lean-into questions and curiosity. When we bump up against something, instead of leaning into defense or ego, we lean into curiosity and questions. It includes deep-listening building, which is everyone thinks they’re good at and no one really is that good at. And also reflection and time and intentionality, which so few organizations feel like they have the space to include in all of these containers. But when you engage that set of things in everything you do, that’s just how we operate, that’s just how it is. And it doesn’t make the difficult discussion more comfortable because it’s a difficult discussion, but we all know how we’re going to operate when it comes up.

Tucker Wannamaker:
So I hear a lot of shared agreements, shared understandings. We have one at THRIVE, which is lead with appreciation, as an example, which is a learning that I’ve had to unlearn from leading with the edit first. “Okay.” A lead of appreciation, and we’re learning how to even do that and our own core values themselves around co-creation and things like that. But I’m hearing a lot of shared, coming up with shared agreements, even before a meeting itself, or maybe even if you’re having a difficult conversation, right in front of you, creating the container within that difficult conversation itself. And I love how you use the word agreements. We’ve heard that in our podcast before too. Not expectations, how I expect you to show up, but what would I love to have and then, subsequently, what would we love to have and what can we be in agreement around so that we can go into this container?

Sarah Fanslau:
Janai, I wanted to invite you, and you’ve done a lot of this work around difficult conversations. Curious as you think about back to your conversations. I’m thinking about a few you and I have particular been in, not Janai to Sarah difficult conversations, but Janai and Sarah with other humans in difficult conversations. Just curious what’s coming up for you as you think about how to do this while in some specific spots you’ve been in and what you’ve done?

Janai Smith:
Yeah. So definitely what came to mind as Tabitha was sharing is that yes, in an ideal world, those containers are already there, and sometimes they’re not, even when you work at an organization that’s been around for years and years and years. And so I think the important piece is to be ready to jump in, to have amazing individuals like Sarah, like Tabitha, and like Tucker, I’m sure, who are ready to say, “Okay, this doesn’t exist, and we have to create it.” And so just thinking about our time at MG, unfortunately in 2020, a lot of things were happening, and we were not prepared to have difficult conversations. But folks had to step up and say, “Okay, we’re going to create this space.” And we literally, well, Tabitha literally created the brave space for people to come and have difficult conversations. So whether we’re talking about the murder of George Floyd, or whether we’re talking about how the pandemic affected different people differently, really just leaning into that discomfort and saying, “I’m going to start this because it’s important and it’s necessary.”
And so with that said, hopefully it doesn’t always fall on one person, but there are going to be those times where even the folks who do this work, and they shouldn’t have to be the ones to step up, they do. And so that’s kind of what comes to mind. It shouldn’t always have to be the same folks, but sometimes it is. But yeah, and just being willing and open. Yeah, that’s …

Tucker Wannamaker:
Well, I’d love for either one of you to walk through where have you had a brave space that you have tried to create that did go well and what happened? What were the factors, the specific factors involved and what helped it to go well? And then one that didn’t go well, it didn’t go how you wanted, and it was perhaps a great learning experience for you. And what were the factors involved that you learned from that?

Janai Smith:
Sure. I can start with one that went well.

Tucker Wannamaker:
Do it, yeah.

Janai Smith:
It might be a bit of a cop out. Sorry, Tabitha.

Tabitha May-Tolub:
You’re good.

Janai Smith:
So yeah, so thinking about during the pandemic, unfortunately when George Floyd was murdered, there were a lot of students of color who were devastated, and students in general, but especially our students of color were devastated, and there wasn’t a space for them to talk about it. And then some of those students of color had advisors who were white, and they just had no idea what to do. They’re like, “I’m a white person. I can’t relate to this youth of color. What do I do?” And so one, just naming that I think was extremely important. And so what we were able to do is create this space where we said that, “This is going to be really hard and really uncomfortable,” but naming that is one of the biggest things I think that was productive and effective.
And then again, leading with those community agreements of saying, “Hey, we are all here with good intentions, and yes, we might mess up, but at the heart of the hearts, we’re here because we want to learn and we want to be able to support our folks, specifically our young people.” And so knew that we had I think it was four or five sessions, but we had a couple of sessions, and I think that was another area of success is it wasn’t just one conversation, “Okay, we’re good.” It was, “No, this is going to be an ongoing conversation for the next couple of weeks.” And then of course, making it optional. We don’t want to force anyone into these spaces because that defeats the purpose. So having folks opt-in, but also asking that the folks that do opt-in, if they’re there fully, they’re not in and out, that they’re staying focused, they’re not distracted. So really being committed to the space were some of the things that went well.

Sarah Fanslau:
And I will say, because I was there at this time, that I think one of the things that we also did that was important was two things. One is kind of create a brave space template so teachers and adults could go and take that and do that, right? I think to Tabitha and Janai’s point, there’s so much fear, and if you can give folks even just a roadmap, I think there’s something to hold onto, and you’re like, “I can take this at least and go out.”
And the other thing that I think we did, although we could have been more proactive with it, was also have the conversations internally. Because I think oftentimes, especially in organizations that are doing frontline work, there can be a real disconnect between what the organization does outside and what it looks like inside. And that can really, I think, create dissonance for staff working in an organization where it feels like they have to be this one person outside and this other person inside. We don’t operate that way as humans. We can’t. We’re one human.
And so we did have conversations inside the organization about it, and I think, Tabitha, to your earlier point, had we been an organization having those conversations before the murder of George Floyd, we would’ve been in a much better spot. Because I think what comes up for folks, regardless of whether we want to or not, is why is this important to you now? Why is it important now? Because everyone else is watching. And that’s true for so many organizations. So many organizations were reactive in that moment, because they didn’t have anything before that. And so I think that was both kind of a win and a learning for the organization around who it has to be outside of moments of crisis.

Tucker Wannamaker:
That’s good.

Tabitha May-Tolub:
Also, I think one of the things you touched on, Janai, that I think is so important is just the skill of just naming something. I think when I’m in a difficult conversation where I’m not sure what to do next. I just name whatever it is. I see this happening, I’m feeling this. There’s a power to just naming what you’re seeing and feeling. I think we also think difficult discussions have to be about solutions then, and innate, they do often get to really great solutions because you’re actually hearing all the pieces, but that’s not where they start. They have to start with safety, and they have to start with the humans in the room. And you have to be able to empathize without feeling like you are agreeing, because it’s really not about that. So I think just that piece of naming it is so important to the piece and the goal of the difficult conversation. Why are we having this? What’s the point?

Sarah Fanslau:
Yeah. Tabitha, that reminds me of another difficult conversation we had at Multiplying Good where it was about a program decision that was made, and this piece around coming together to have the conversation about what folks were thinking and feeling about it without changing the decision. I think oftentimes there’s this neat .. And that was actually my response, right? I’m like, “Let me fix it.” I want to jump to fixing, and instead of jumping to fixing, which is our natural impulse, I think, so much of the time, it’s like, “Let’s stop and hear.”
And what I heard in that conversation, and a lot of staff were there, was that if we had jumped to fixed, we would’ve maybe been solving one person’s problem and creating a problem for others. And so it’s such an interesting piece, and when you bring the voices all together, then you can hear, “Oh, so there’s this kind of stream of thought over here, there’s this other one over here, there’s this one over here.” And then to your point, maybe the point isn’t to change the solution always, but to just recognize that there were thoughts and feelings about a thing. Yeah. Yes. Yeah.
Well, y’all, I want to invite you into our next question, which is just we have this frame, we want to think about the next normal of nonprofit leadership. If we’re thinking what we want this sector to look like or even impact-driven leadership, what is the next normal for you all when it comes to difficult conversations? What do you hope to see in the future?

Tabitha May-Tolub:
I feel like I’m reinventing. I’m saying similar things, but I think the essence here is the same. I think if we want a new normal, we need leadership that looks at this differently. I think we need leadership that looks at difficult conversations not as an obstacle to be overcome, but as an opportunity to really see things bigger, see things differently, or just care for their team in a different way. I think we need CEOs and EDs and boards that buy into this as a valuable tool. And then to be able to support staff, like we said, with formal training and informal training and structure that just consistently creates spaces and opportunities for us to have these conversations.

Janai Smith:
Absolutely. I totally agree. And what I would add to that is also just, and I also feel that I’m saying similar things, but just the willingness to create that space for your staff as well. It should definitely be happening with our leaders, but there should be this sense of community and the sense of openness and belonging where staff can come together, have those conversations and be heard. And so I think there’s something important about leaders not just making decisions as they have these conversations, but opening up so that staff or whoever else is involved, stakeholders can come to those leaders as well to give their input on what needs to be done and how things can be changed.

Sarah Fanslau:
Tucker, curious if things are coming up for you as you’re kind of hearing some of these pieces around. It sounds like both kind of giving the training and tools for folks and then just creating the conditions throughout an organization. And I would add structures, the conditions and structures for folks to engage in this on a regular basis. But as you think about our work, what’s resonating with you here?

Tucker Wannamaker:
I think the first time that Erin facilitated us having a joint group discussion about our sorrows over the last year, and it was both the wins and the accomplishments, and it was the sorrows and disappointments. And I know that because of that, we started implementing that in our regular work of inviting spaces in a group, in a whole group, and we try to create containers around not disparaging people, as an example. And we’re learning into how do we create some of those agreements that somebody’s not like, “I hate that woman,” and it’s like, “Oh, that’s defeating the purpose.”
So that’s why I keep thinking about these containers, but that’s one of the ones that comes up is, Tabitha, what you just said around this is not an obstacle to overcome per se. I don’t have to figure out a solution per se. Let’s just hear first, let’s just listen first and then see, and then we can go from there. Not just assuming we need to go somewhere, because we may not. We may just need to create space for people to feel heard, which is what I keep thinking of is how do we help to know, you said this earlier, Tabitha as well, around most of us think that we’re great listeners.
But I’ve been wrestling around with this actually with my 11-year-old daughter Ella, and I’m like, “Okay, the classic listening is not because you heard what I said and can tell me the word. Listening is that I feel listened to,” is what I’ve been saying. And I’m like, “Wait, do I even think that that’s true?” You know how it is with parenting, and you’re like, “I think I just shared something, and I need to figure out if I actually believe it.”
But I’ve been wrestling through this concept of what is listening in the first place? If I’m a good listener, does that mean because I’m able to reflect back, or is it because somebody feels listened to? Is it really about the other, not about me? I’m thinking about David Brooks’ newest book right now around how to see others deeply and be deeply seen, how to know a person and some of the things that he’s getting in there, and so much of it is about understanding how I’m showing up in this space, but also does somebody feel deeply seen in the first place?
And so I think that’s coming up for me is trying to figure out when is the space, and I don’t know this. I think about this with my own wife. When did we know it’s the space to move forward, and when do we know it’s the space to just hear and to listen? There’s a question that somebody told me once of, “You can ask your partner, do you want to be, what was it, heard, helped or hugged or something like that?” And then, because I don’t know right now. To your point that y’all have thought, “I don’t know.” Janai, as you were saying, just naming it, there are so many times where I just don’t know what to do, or I’m confused in that maybe somebody does need solution and maybe they just need to be hugged or maybe they just need to be heard. And me knowing what’s supportive is what keeps coming up for me around this power of listening, and how do we do that?

Sarah Fanslau:
But I think you just gave your own answer, which is you just ask, right? You ask, “What do you need right now?”

Tucker Wannamaker:
Well, and in these contexts, Janai and Tabitha, as you’ve been in some of the harder difficult conversations where somebody does voice, whether it’s written voice upon a board somewhere or verbal voice into the room that makes it more difficult, what do you do in that moment? What do you do to defuse, to honor what’s being said? Because that to me is what people are most afraid of, I think, or that’s at least one of things.

Sarah Fanslau:
Yeah, feeling attacked.

Tucker Wannamaker:
Yeah. It’s like, “I’m going to be attacked, I’m vulnerable.” And if I’m in a moment where I feel like somebody is attacking me, what do we do either as facilitators or the one who is being given that difficult conversation, if you will? Curious your thoughts on ways to approach that.

Tabitha May-Tolub:
Do you want to kick that one off?

Janai Smith:
Sure. So I think that’s where those community agreements come in. That’s the first thing that came to mind. Because if you have those set up, you can always revert back to them or refer back to them, excuse me. So if something is going on where there’s an ouch moment, if you will, we can say, “Okay, let’s take a pause. Let’s review those community agreements so that we know we are all here in good intent, and not we’re going to lean into this discomfort right now. We’re not going to attack anyone. We’re not going to point fingers or anything. We’re just going to remember and be reminded that we’re here for a joint cause and that we’re all here in good intentions.” And so I think that’s one of the first things that’s helpful.
The other thing that I did not mention earlier is that it could be helpful at the start of these conversations to do a grounding exercise, again, to really just bring everyone into this space so that we’re all taking deep breaths. We started this conversation off with a collective breath. So even small things like that, or in those moments, if, let’s say, we did not start with a grounding exercise, maybe we take a pause to do a grounding, to reground us, do that exercise. And I think that’s one of the things that sometimes facilitators can get nervous about. It’s like, “Nope. We have a schedule. We have to follow this.” But it’s like, “No, no, no. Something went off the tracks. Let’s take a moment to pause and let’s recollect ourselves.”

Tabitha May-Tolub:
I think it’s also super important to understand just how we function as humans and how our brains work. So to have those skills when the tension in the conversation gets high, to release that tension, because it is literally a different part of our brain. That is fight or flight, that is our caveman brain. We cannot have a connected conversation when that part of our brain is on fire. It’s just not possible, and to try to do that is only going to lead to more pain and more hurt. So to be able to relieve that tension in some way, to take a breath to remind people of ground rules.
I think it’s also so important, and this is a high-level human evolution here, but it’s so important in these conversations to understand that feelings that come up that are strong are likely not about you. I think that was one of the biggest lessons I learned in that year when I would encounter someone and I would feel like myself getting defensive, I am like, “I’m not approaching this the right way, but also these feelings are because of a history of experience, and I need to honor that. I need to put my ego aside for a second and be like, ‘This person’s reaction to what I just said is one about my inappropriate,’ whatever I just said, and I got to autocorrect, ‘but also there’s experiences there and feelings there that I don’t understand, and part of this interaction is me trying to understand is best as they’re willing to share so that we can have a human to human interaction.”
So I think going back to, I know it’s hard to, everyone wants to know what to do in the crisis, but it is so important to put this stuff in place long before your team is in crisis, because then no matter how heated that is, you have a relationship with this person. You are coworkers. They saved your butt on that project last week, they did that amazing thing with that young person that brings you to tears every time you think of it. So no matter what just happened in that interaction, they’re a human that you care about, and so that makes everything going forward easier. So I just think laying that groundwork is so key.

Sarah Fanslau:
Yeah. Well, and even there’s some great research on the importance of high quality connections in the workplace and what they really point to. It’s the broaden and build theory. It’s both kind of long-term relationships, but that we can establish meaningful connections in a very short amount of time with other humans, and that is that grease on the wheel that we need to get through these pieces.
I was going to play a little bit of Devil’s advocate, though, on what you both just shared, because we were a workshop last week, and we are doing a strategic plan with an organization that’s going through a lot of crisis. And we were asking folks a question, I forget exactly what it was, but folks were putting things up on this tool, we call it Easy Retro Board, which is a digital tool. It’s an anonymous board so people can write whatever, and people were writing folks up, things up, and there were a number of pointed comments. It wasn’t kind of to a specific individual, but to departments, and there are not a ton of people in the room.
And there was a conversation about, or there’s this thing that comes up between people being free to be authentic and people not offending others. So I want to put that to you. What is that line? If I’m sitting here being like, and I know what Adam Grant says, but what do you guys say when I’m sitting here saying, “This is my authentic self, right? I’m telling you what’s authentic to me.” How do I deal with that versus I’m offending other people? What does that look like?

Tabitha May-Tolub:
I don’t know. I want to say a flip answer, but I’m going to try to be more productive here. I believe so much in the intentionality of the words we use. We can say the same thing and readjust the words, and it has a more powerful impact in whatever way we want it to be powerful. So I think part of those pointed comments is what’s your goal here? Is your goal to be authentically heard? And if so, you need to say that in a way that people can hear. Because when you put your words out there in a way that’s designed as an attack or could feel like attack, if your intentions were not to attack, but your choice of words came off that way, it is hard for people to hear it. And so that’s a choice you have to make.
I think sometimes people use that as an excuse to just say what they want, and sometimes people just don’t have the skills to rearrange their words in a way that lands more clearly. I think one of the things, just to give Janai some flowers, I think one of the things I love about Janai when she’s in these conversations is she can say the most powerful things, and the way she says it and the words she chooses, people have to hear them, and that’s a really powerful tool. And I think in that toolbox of having difficult conversations, being able to shape your language so people are allowed to hear powerful things and they can take it in, that is a game-changer, for sure.

Sarah Fanslau:
Right-o. Yeah, yeah. Janai gets heard a lot and for good reason.

Tabitha May-Tolub:
Sorry. Now I embarrassed her.

Sarah Fanslau:
So true though. It’s so true.

Janai Smith:
Thank you. [inaudible 00:38:17]

Sarah Fanslau:
Although I feel like that might become a burden at some point, Janai. I am not sure.

Tabitha May-Tolub:
I hope not.

Sarah Fanslau:
Yeah.

Janai Smith:
We’ll see. I’ll keep you posted.

Sarah Fanslau:
Janai, what are your thoughts on this authenticity versus kind of …

Janai Smith:
It’s such a great question, because I often in my personal life think about this, although I know the answer for my personal life. But in professional settings, I think to a point that was made earlier around high quality connections, so if we have a culture where folks feel connected, where folks truly know one another, you know that you know yourself and you also know your coworker, and so that if you say things a certain way to one person, it’ll be totally fine, but if you say it to someone else, they may be offended.
And so I think just keeping that in mind and, to Tabitha’s point, keeping your intentions in mind is also going to be phenomenal. If you focus on what your intention is and what the main goal is, rather than, “Well, I’m feeling fired up and let me be me,” kind of thing. It’s like, “Well, no. What is the goal of the conversation that we’re having, and how can I get my point across in that way?”
Because I’ve been in situations where I just want to be my authentic self and say things how I choose, and I’m like, “That’s not going to land with these folks, and so let me retweak, let me tweak the way that I’m saying it.” And so I think it’s just really being mindful of your audience and mindful of the folks that you’re talking to. And I think, of course, there are heated moments where that goes out the window, unfortunately, but I think one of the things that needs to happen is you have to self-correct immediately and either apologize or whatever it takes to mend that space and take accountability for, “Yes, I was being my authentic self, but I also hurt someone, and that’s not okay.” So just kind striking that balance.

Sarah Fanslau:
Yeah, yeah. I’m hearing something really important for both of you. And the reality is a lot of cultures don’t have guardrails, and so you go into spots to have conversations, and you realize or we frequently realize that there’s no kind of cultural norms around conversation, which puts everyone at risk, right? Everyone at risk, because it means any conversation has the potential to damage both individuals and the organization. And that before we can do anything, we need to figure out how it is we want to be together right now so that we can do that as we try to work forward.

Tabitha May-Tolub:
I think the other thing that we haven’t named yet is, and maybe that’s another question we’re going to talk about, but in these organizations, these problematic communication dynamics that just exist that are about power and that are about [inaudible 00:40:57], they just exist already, and we can’t just operate inside those. We have to challenge and change those. My favorite thing that leaders have done, and this has happened to me more than once in my career, is when a leader steps into a space and goes, “This is a safe space.” It’s a commandment, it’s an order.

Tucker Wannamaker:
You will [inaudible 00:41:16].

Tabitha May-Tolub:
I count the number of times that that has happened, I’m like, “You can’t mandate that. That’s not how that works.” So I think that’s an important thing to just name. You can’t just put new things in the old space. You got to change the space.

Tucker Wannamaker:
Oh, that’s good. So if I’m a CEO of a company or a nonprofit that’s trying to have impact in the world, and I have all this fear around having that conversation that I know I need to have or a collective conversation around a really tough topic, I’m curious in a sense of thinking about going almost, Janai, you were kind of hitting on this too, around understanding the goals, but this is taking it even further. What is, if you will, the joy set before me that would allow me to really step into that fray, to step into that fear? What’s made possible for me as a CEO or me as a team leader or me as an ED if I courageously step into this? What’s made possible in my culture, what’s made possible in my fundraising, what’s made possible in whatever it is that you’ve noticed and seen of the after effects of being able to host these difficult conversations in this kind of way?

Janai Smith:
Oh, god. Well, the first thing that comes to mind, I’ll pop in there, is definitely there’s this, at least internally, there’s this culture of trust now and almost authenticity, because if I know that I can come to you and I can have these difficult conversations, I have a whole new respect for you as a leader. And I also know that when things get difficult, let’s say in my specific department, that I can come to you and bring that in, maybe even be under your mentorship to then help whatever situation may be happening there. And so I think there’s definitely this idea of … I’m losing my words, sorry, but there’s this feeling that I can do that too, and that even though it’s hard, I can step out and be brave and create those free spaces as well.

Tabitha May-Tolub:
For sure. I love that. And I think not everyone’s so into personal growth, but you’re going to grow a heck of a lot as a leader. Every painful conversation, every time I’ve been self-threatened or attacked or hurt someone that I care, every terrible difficult conversation I’ve had, I’ve come out a stronger person. And as a leader, I think it’s invaluable. Non-profit professionals, too, we’re a rare breed. We work hard, but we work harder when we are feeling it. So to create an environment where everyone feels seen and heard and connected to each other, forget about just like, “Oh, that’s nice,” that is a necessity where we have nonprofits failing left and right for money reasons. This is an invaluable resource to have a high functioning team who really feels like they can be in it together.
And I think most of us know, I won’t say we all, but most of us know how important it is to have a diverse team and a diverse organization. We know what happens when you just have people that agree with you all the time. We know what happens when you don’t engage in the diversity of our world and the community. No matter how many DEIB policies you have, you are not going to be able to do that unless you are able to navigate difficult conversations in authentic ways. It’s just not going to happen. People are going to come and leave. So there’s so many tangible reasons to do this besides just like, “We should be doing this.”

Sarah Fanslau:
Yeah, and I will just say I think one of the other things that I have seen in my lived experience and also comes out in that research around high quality connections is that organizations have to be really careful of the folks in organizations that may be driving down or creating spirals of negative communication, those individuals who everyone in the organization kind of knows, “Sarah over there is a little bit of an issue,” and we just kind of let it slide. Because letting kind of bad behavior slide is a real issue in organizations and signals to the rest of the staff that it doesn’t matter what I do here or how I show up, and I can treat folks any way I want. And so I think as we think about difficult conversations, we don’t mean mean conversations, clearly, through our conversation, and we have to be really careful about the dynamics we set up around kind of all communications in workplaces and really hold folks to account for showing up in the ways that we’ve all agreed to show up.

Tabitha May-Tolub:
And the beauty of the tools we’ve talked about is they apply to every difficult conversation. If we’re talking about identity differences, if we’re talking about work style differences, if we’re talking about vision difference, same skills. So once you have them, you have them.

Sarah Fanslau:
So folks, last question. We have just a few more minutes. I need some really practical steps. If I’m a nonprofit leader right now, and I have an employee I need to talk to, I need to have a difficult conversation about race, I want to, whatever it is, what are my top two or three practical steps I can take, and especially if you have them, any tools or resources folks can go check out?

Tabitha May-Tolub:
Yeah, I would say the leadership needs to model it 1000%. Whether it’s comfortable or uncomfortable, you have to model it. I think you need the tools and the structures in every part of your organization. They’re simple, apply them everywhere. And you need to seek out diverse opinions and thoughts and perspectives on your team to create that openness, that curiosity in those questions.

Janai Smith:
Absolutely I agree. And what I would add to that is don’t be afraid to lean into that discomfort. I know it sounds like kind of a pie in the sky thing, but that’s really what it boils down to, in my opinion, or one of the things that it boils down to. Because with that, to Tabitha’s point, you’re going to be modeling that behavior. If you can even, to what we’ve been saying for most of this conversation, you can name the fact that, “Hey, this is what I’m attempting to do. I’m not going to be perfect at it, but I’m trying.” I think staff members will appreciate that.
And something else that we mentioned earlier that I think is really important is ensuring that your staff members are heard and that their voices are included in this. So before we just jump into difficult conversations, asking what does the staff need from me? What do my stakeholders need from me? How can I make sure that this is a space that is truly a safe space? I’m not just coming in demanding that it’s a safe space, as Tabitha mentioned earlier. And so really, I think if I had to sum all of that up, it’s really taking the “I” out of it and bringing the “We” into it. It’s like it’s not about me, it’s about the folks whose voices I’m trying to elevate and make sure that we are having this dialogue.

Sarah Fanslau:
Yeah. I love that. Tucker, what about you? What are your fast tips?

Tucker Wannamaker:
I think based on some lived experience and what Janai and Tabitha have shared is if you notice reactivity happening in either yourself or in others, to just take a moment to pause. We all have reactivity, and even Sarah, what you’re hitting on with bad behavior, I think any form of reactive behavior, whether it’s fighting or flighting or freezing or fawning, generally speaking, isn’t supportive of the environment. And so if we notice that within ourselves and within others, just encouraging a moment of pause like, “Hey, can we just take two minutes? I’m feeling a little bit … My nervous system’s going crazy.” Just create the space. I think that’s been so valuable for us, and I’m grateful for that. So that’s a really practical tool to just give space to it.

Sarah Fanslau:
Awesome. Well, I love that. I love having you all on this podcast. It was such a pleasure to see your two faces again on my screen. It’s been too long. And we’ll put some links to some tools and resources in the show notes for y’all to check out.

Tucker Wannamaker:
Oh, yeah. If y’all have some tools, that’d be great. Yeah, [inaudible 00:49:37]

Sarah Fanslau:
Yeah, send them our way, for sure. And then I’m sure Janai and Tabitha would be willing to connect with y’all on LinkedIn if you want to kind of send a request their way. So y’all, I hope you learned some things about difficult conversations. We are all still learning around difficult conversations, and hopefully we can all have them more often.

Tucker Wannamaker:
True.

Sarah Fanslau:
So thanks to everyone for listening, and we’ll see y’all soon.