What started out as a typical newsletter call turned into something else this week. We were all set up on a group video call to create the next newsletter when the conversation took an abrupt turn. Our topic was values, something we talk about a lot.
MJ wondered aloud if we might use a recent team presentation as an example. “As we were planning the presentation, doing something new together, we talked about whose voice is acceptable, where we belong, and where we’re needed.”
“I think I’m seeing that in a very different way,” Aubrey replied.
The air shifted suddenly. We could feel it collectively, even across five different cities.
Aubrey continued: “I was just told that we were doing the presentation. No one asked me. I came to a team business development meeting and was told, ‘we added you because you have legal background.’ So, during the presentation, I didn’t know why I was there. It wasn’t a legal presentation.”
Aubrey’s perspective immediately pushed the rest of us outside our comfort zones. We saw a potential conflict unfolding. It wasn’t part of the newsletter plan. But we had to make a space for this conversation now—it was too important not to keep going.
MJ offered a different memory of how everyone came to the presentation. She agreed that “the presentation could have been done without any kind of legal background. But because you do have one, I think it enriched the conversation. Your experience helped me make connections, which is why we wanted you to be a part of it.”
But MJ also remembered asking Aubrey to join in. “My memory is that we brought it back to the team and said this would be great. Aubrey and Kim would be welcome to join. But it sounds like from your experience, Aubrey, that you were “volun-told” to do so.”
Leaning into a Difficult Conversation
This is officially where we abandoned our agenda to create a newsletter and decided to hold space for the conversation that was unfolding. We knew it was important and that we wouldn’t be able to focus on any other topic at this point.
When we debriefed about this conversation later, Jennifer noted that this is how difficult conversations generally arise—people stumble into them. “If you don’t have a foundation of partnership in your organization, you might back away from this whole conversation. You might say, this is uncomfortable so I’m going to leave. Our ability to hold the conversation instead of tapping out is a sign that our partnership is active.”
Jennifer continued, “Rarely do people schedule these conversations. It’s not like something happens and then we put a time to talk in our calendars. It’s much more realistic that we are asked to live our values in the moment, we have to lean in and have the difficult, uncomfortable conversation.”
We also want to note that what MJ is demonstrating is deep listening—listening to understand and mirroring back what she heard. It’s how you honor someone else’s words. It’s how you see them fully.
Over the next few minutes, it became clear that Aubrey hadn’t been at a meeting where the presentation responsibilities were decided. “I didn’t find out about it until I was already in the meeting. By that point, I didn’t know what my role was.”
Asking clarifying questions is another part of deep listening. MJ’s question was, “Why didn’t you say you didn’t want to do it? Or did you not want to?”
Aubrey responded, “It’s not an issue of my not wanting to. It’s not knowing what my role was supposed to be.” And then Aubrey really leaned into vulnerability: “Something I’ve been struggling with is my role in the company. My role is different: I have a department. In addition, I’m doing learning and development. It doesn’t work the other way—the rest of the team isn’t doing Talent Advisement on top of their work.”
We paused to take in this statement. It seemed hard to say. It felt heavy. And it felt monumentally important.
We tell clients that they don’t have to have all the answers. This is especially hard for leaders who are socialized to be responsible for every solution. Sometimes, what’s needed is just a question. Just some more curiosity.
“I’m wondering,” MJ began, “how you see your role within the organization. What I heard you say is that you feel a lot gets added to learning and development, but not so much a reciprocal receipt of support in your role. Did I hear you, right?”
“Yes,” Aubrey confirms that she has been heard correctly. “When we were doing the presentation as a group the first time, I could sense some frustration from you. Perhaps because you felt like we should have all gone through it before because we all owned it. But at that moment, I didn’t feel like I owned it. I felt like I was helping with my legal background, not that I was a part of the presentation or its creation. All this stemmed from the fact that, again, I was just told I was doing this.”
As for her role at Leverage to Lead, Aubrey acknowledged a struggle to define her scope and the unique pressure she feels as the sole head of an entire department. In a traditional corporate environment, silos are the norm, but we’ve seen how damaging they can be to collaboration. At Leverage to Lead, we don’t want silos. Our work depends on the energy and creativity of all of us together.
Sitting with the Discomfort
MJ brought up a post on LinkedIn that she had noticed just that morning, and connected it to her question about Aubrey’s role. “I wonder whether you feel siloed in your work because I was surprised to see a post on LinkedIn that said, ‘Aubrey’s Hiring.’ I didn’t know that was happening. I was surprised.”
The deep listening continued. Aubrey shared her reaction to MJ’s comments. “Well,” Aubrey responded, “my whole job is hiring, right? I post about jobs all the time. I don’t feel like my work is siloed, but I do think it’s interesting that you’re saying you didn’t realize I was hiring because that’s a very large part of my job.”
We were all listening and making room for different perspectives. We got clear on all the perspectives without saying anything is right or wrong, no “should” or “shouldn’t” in our feelings or perceptions.
Then Jennifer shared that she felt surprised by the hiring post, too. “If you’re hiring, come back to the team and tell us you have a new position you’re recruiting for. One, it helps us understand how busy you are and gives us context. We’d know if you don’t have time to do something because you’re recruiting for so many positions. Two, it would help us to know if we need to rely on someone on our network for support.”
At this point, Jennifer brings the conversation back to Aubrey’s role and her level of inclusion in the larger organization. “I imagine,” Jennifer reflects, “that the conversation where the decision about the presentation was made was held on a team call, and Aubrey isn’t always on those calls.”
We wonder if Aubrey needs to be included on team calls. There’s concern about Aubrey’s time and pulling her away from recruiting work to be on calls. But then again, everyone needs to be caught up. Being a remote team means we’re not always together sharing information, which can create a silo effect, even if unintendedly.
Landing on a Core Issue
What started out as a miscommunication about who was invited to create a presentation has opened up a line of conversation about something deeper and more impactful. Jenifer names it: “The question we need to ask at this point is, ‘What does collaboration really look like for us?’”
This elicited more questions: should Aubrey come to standing meetings on Tuesdays and Thursdays? What HR and recruiting items should Aubrey and Kim bring back to the larger group? We know we have to be proactive and intentional about meetings because we are a remote team spread across the country. How do we ensure everyone has the support they need? How do we make sure we’re all connecting and feeling connected, both to each other and to the fabric of the organization as a whole?
“It’s difficult,” Aubrey said after taking a moment to listen, “to do placement and recruiting at the level I need to and attend all team meetings. I’m trying to figure out how to make it all happen. We’ve considered hiring an assistant, but that may not happen for a while. I’m trying to figure out how to manage doing all these things without working 60 hours a week.”
This is the moment when we have to lean on our value of Creativity. We never want anyone to work 60 hours a week. We want creativity, flourishing, collaboration, risk, imagination, and communication. If something is not working, then we come together and see what will work. What would it look like? What support is needed? How can you feel integrated?
It’s not surprising that Aubrey’s role has evolved over the year that she’s been with Leverage to Lead. It’s our job, collectively as a team, to help create the role that will work. Perhaps that means some untraditional features. Either way, it starts here, with this dialogue.
Calling on Our Inner Agility
MJ described feeling “full of adrenaline” and having wanted early on to change the subject. “I felt worried about my relationship with Aubrey. I want to feel like we’re moving together toward a shared goal, not for Aubrey to feel like she has separate goals. But it doesn’t feel like we’re there right now. Despite my discomfort, I kept my butt in my chair to have the conversation because shared goals are what I want. I also feel like I failed Aubrey with the presentation. I didn’t ask if you wanted to be part of it. That feels like a failure that I can’t fix now because it’s done. And I also feel vulnerable because I don’t know enough about what Aubrey does. I’m fighting against feelings of incompetence. And I’m feeling responsible.”
Aubrey summed up her emotional state as “not feeling amazing. I think I feel very frustrated because as head of talent advisement, I have a budget and monetary goals, and placement goals. No one else has those. It feels almost like starting my own small business within a business. I feel like I need to be successful in my role to make sure that Leverage to Lead as a whole is successful. So I feel frustrated that not everybody shares that pressure.”
Kim described feeling vulnerable and exposed. “I’m one of the members of the team who is least likely to talk about my feelings. I did have some adrenaline going. I want to do what I can do to help and support. The conversation made me reframe thinking about our meetings and how to approach them. I plan to think of them more as collaboration meetings.”
Jennifer’s primary feeling was relief. “I feel relieved for a number of reasons. One is because this is fixable. These are things that we can manage. I’m also relieved because everyone is having the dialogue with agency and accountability—showing up in the conversation without me having to have the answer. As a CEO, I feel this is a problem we can deal with.”
Where to Now?
This was, to be honest, an intense conversation. We all needed some breathing room and some downtime to collect ourselves.
There isn’t one prescribed follow-up for any difficult conversation. In our case, the next thing we needed to do was process the conversation individually. We make a promise to come back to it by giving it an agenda item at an upcoming meeting, and everyone is accountable for showing up and being able to talk through it. We commit to talking further about how our team functions, how we structure meetings, how we prioritize whole-team gatherings, and how we ensure we do not grow siloed. To be prepared to hold that conversation, everyone needs to take the responsibility for processing their experience.
In the spirit of radical honesty and taking you into our own journey so that you can see the work being done, we’ll let you know how that next conversation goes. For now, we’re deeply grateful for the opportunity to talk with each other, in hard and uncomfortable ways and in delightful and joyous ways. We’re grateful for those of you diving into the same work, making progress in your own journeys, and sharing in ours.