Why group trust can’t replace individual trust on a team
Hi friends! I’ve missed you!
We are back from our Break Week, and I am so excited for this week’s topic. It’s about a leadership ah-ha moment I recently had.
But first, some context:
One thing I’m really proud of is the culture of trust and open feedback our team has built. It hasn’t been easy. It’s taken us more than a decade to get to a place where we can have transparent conversations as a team, openly disagree, and challenge each other from a place of compassion.
In fact, the psychological safety of our team is so strong, we have nearly all of our high-stakes conversations as a group. This is quite a difference from how it was in the early years, where I needed to have one-on-one conversations in order for people to feel safe to speak up and give feedback.
But now? Now we have quarterly, verbal 360 reviews as a team, where we openly give our feedback to help each person grow. We also look at five areas of our team dynamic—our trust, relationships, collaboration, communication, and personal happiness at work—and rate how we feel we’re doing on a scale of 1 to 10. And then, we share our scores and why they are what they are . . . out loud.
Even though our team trust is now what I always dreamed it would be, I’m recognizing one shortfall: Even in the healthiest, most open team cultures, some conversations require a private space and a direct invitation. No matter how comfortable you are with a group of people or how much trust you’ve built between you, one-on-one conversations still matter a lot. And I’m recognizing that I need to have more of them.
You may remember that a couple months back, I wrote about a series of tough and meaningful conversations I had with my right-hand person, Monique, who is our team’s Chief of Growth.
Those chats helped me recognize that not all feedback comes up in a group setting—nor should it. Monique and I were both carrying some frustration, but it wasn’t something we were intentionally withholding from each other. It’s just that sometimes, you need a private space to air out tension, get clarity on the underlying issues, and resolve them together.
That makes sense, right? We know we need one-on-one time to strengthen relationships and trust. But for a leader who is used to everything being a team conversation, it can be hard to recognize when I need to carve out that individual time.
When Monique and I decided to write about our experiences with our one-on-one discussions on the blog, it sparked a meaningful team discussion that made me think deeper about all of this.
In a team meeting, one person shared that she was bummed to learn about Monique’s and my conversations by way of working on the blog posts about them. She thought we should have talked about them as a group, especially if we thought they were consequential enough to write about. Another had a different viewpoint: She shared that she didn’t feel a need to know about one-on-one conversations, even if there was a blog post written about them.
I love that we have a team where we can openly discuss viewpoints like this. I understood each perspective, and it felt like a real leadership dilemma: Where is the line between one-on-one and group conversations? And what does it mean when we share something here on this blog?
We worked together as a team to get to the heart of it, and here’s where we landed:
We agree that not everything should be a team conversation. I shared that I want to be a leader who respects individual trust, and that means some conversations need to stay private, especially if they don’t involve anyone else. The team totally respects that. But there’s an important distinction: If I and someone else from the team decide to share a private experience in a blog post, the team should hear about it from me first. Even though not everyone on the team feels a need to be in the know, I think that if it’s something I’m going to share publicly, I’d like to discuss it as a team first so that no one is caught off-guard.
I’m really glad we had this conversation and made these distinctions, and I feel clear about how we’ll handle it if we have another situation like this in the future. But more than that, I’m glad we paved the way for more one-on-one conversations on our team.
As things are now, I don’t have one-on-ones with members of our team, not even for performance reviews. We do everything, including reviews, as a group. This is partially because I’m a big proponent of avoiding unnecessary meetings; I don’t have standing one-on-one meetings, either. Instead, I keep up with my team via WhatsApp voice messages. I talk individually with my team all the time without ever formally scheduling a meeting.
The only place we currently have more formal one-on-one chats is our “Stay Interviews,” where I ask each person two questions: What needs to stay the same in order for you to continue being happy and fulfilled here? What needs to change in order for you to continue being happy and fulfilled here? Each person shares their answers with me privately first, but then I present the collective feedback to the group, and we address it together.
While all of this is great and has clearly served us well over the years, I’m finding that I want more structured individual time. I loved my chats with Monique because of where they led us, and I want to have moments like that with each member of my team. But instead of putting a regular meeting on the calendar, I want to do it in a way that is aligned with our culture of flexibility.
I’ve decided that in the near future, I’m going to put occasional one-on-ones with my team on the calendar where I ask questions that I hope will prompt really meaningful conversations. I’m still thinking through the questions I’ll ask during our first go-around at this, but I’m certain they will be about topics that wouldn’t normally come up and that will help us get to the heart of meaningful issues. I know that we have the trust to handle them.
Here are some of the questions I’ve been gathering since thinking about this idea. When I land on my final questions for our first attempt at this, I’ll share them with my team in advance so that they have time to think about their answers before we meet:
On a scale of 1-10, how fulfilled do you feel in your role? If your score is less than 10 and you could wave a magic wand to change things, what would you change?
What is most frustrating about working with me?
In what areas do you want to grow? What would a breakthrough year look like for you? How can I help you/challenge you to get there?
Do you feel like I trust you? Why or why not?
When is the last time you felt truly proud of something you did here? What made it meaningful to you?
What’s a recent tension point you’ve noticed that hasn’t been addressed?
I'm so excited to try this and I’m grateful to my team for always rolling with my ideas. I hope this blog shows you that no matter how long you’ve been a leader (or teaching people about leadership!), there’s still so much more to learn.
How about you? Have you ever struggled with the balance between one-on-one and team conversations? Do you think you’ve ever mistaken group openness for individual openness? Could you consider creating an individual space for greater curiosity and connection?
And while I’m here: If you've ever been asked impactful questions during a one-on-one, could you share them with me? I’m looking for all the ideas as I think about how to make these discussions extra meaningful for our team! Hit “reply” and let me know.
See you back here next week!
Big hugs,
