The key to keeping your team engaged and fulfilled
Sometimes, when things are going really well in our culture and on our teams, we forget to talk about where we want to improve and grow.
You would think that because I regularly teach others how to strengthen their cultures and have courageous conversations about what's working and what's not I’m always on top of these conversations. But it’s like the example of the hairdresser who does everyone else's hair and not their own: I forget that I need to have these same important conversations with my own team.
I recently facilitated a mastermind session where the topic of checking in on people and making sure they're happy and fulfilled came up. I quickly realized it had been quite a while since I last checked in with my own team on how they’re feeling about their work. Things have been going so well that it just hasn’t been at the top of my mind—and I actually think that that’s the best time to have conversations about what could be better. It helps us to be proactive and get ahead of any potential frustrations and challenges.
So, during a five-minute stretch break in the mastermind group, I took action. I sent the team a voice message via WhatsApp and said, “Hey, I just had this realization: It's been a while since I've checked in with you on how you're feeling about work and how fulfilled and happy you are. I’d love it if you could take time to think about this and then share with me what you think is working well and what could be better.”
I asked everyone to reflect on two questions: 1) What needs to stay the same in order for you to be happy and fulfilled here for the next five years? 2) What needs to change in order for you to be happy and fulfilled here for the next five years? Then, I asked them each to share their thoughts with me in a WhatsApp voice message sometime within the following two weeks.
I want to address WhatsApp for a second: On our team, we love using voice messages. We love it because it gives everyone, including myself, more time to think and process. We also all have different schedules, so it allows for everyone to respond when they can do their best thinking. My team knows they can take their time in getting back to me. And then, when they do respond, I have time to think about their feedback and process it before I reply. It’s like having a one-on-one conversation where we each have the space to give intentional, well-thought-out replies.
AND . . .
. . . there’s a reason that this method works well on our team: We have the trust and psychological safety that allows us to communicate in this way. I have been working with the people on my team for 6+, 11+, and 12+ years. We have a culture of complete openness and candor. If we didn’t, I would have had this conversation face-to-face, whether via video chat or in person. No matter how you bring up these questions on your team, I encourage you to use the method that best suits the level of trust and psychological safety you have.
Two weeks after I received everyone’s feedback via WhatsApp, I determined the common themes. Here’s what I learned: In terms of what needs to stay the same, everyone feels comfortable with their capacity and the specific work they're doing, and they love the freedom and flexibility that our culture provides. They love that they don't have to choose between their work and their lives, and they each feel really valued, supported, and cared for.
Where the team suggested that we consider growing over the next five years is in having a more clear path to new benefits and when those benefits will be unlocked. This wasn't a surprise; it's something we've been talking about and working on together for a while now. We want to be extremely competitive when it comes to benefits, and we have focused first on getting everyone to their dream salaries. This feedback helped me see that I want to lay out more concrete steps for what benefits will look like on our team and when we can expect things to happen, just like we’ve done when it comes to compensation growth.
Another interesting thing that came up was a fear of what would happen to our team and company if something were to happen to me. There is a desire to have a conversation around what that future might look like and how we can ensure that the team is cared for on a long-term basis if that were to ever happen. It’s a little morbid, sure, but we know that it’s so important to talk about because right now, we have the chance to be proactive.
The feedback wasn’t at all surprising to me. It was aligned to what I expected it might be, and everything that the team felt, I felt, too. Had any of the feedback been surprising, or if someone on my team had shared that they were unhappy or not fulfilled, I would have had deeper one-on-one conversations in addition to an overall team conversation.
Because everyone was already on the same page, I presented the overarching themes of the feedback at our in-person October team retreat. It was a meaningful, forward-thinking conversation, and it gave me a clear picture of where I want to put my focus as a leader to ensure my team continues to feel happy and fulfilled. My biggest takeaway from the conversation was an overall feeling of gratitude: I’m so glad that the team is really happy and that we're all on the same page about the areas where we want to grow.
When you have conversations like these with your team, I think it’s really important that people know that their feedback matters and that it's not just going to float around somewhere. Responding to feedback and making sure people know they’ve been heard is what inspires them to speak up again in the future. They’re more inclined to be honest about how they're thinking and feeling if they know that something's going to happen with their feedback.
So, leaders: Here’s your reminder to check in with your team, even if things are going really well—especially if they are going really well. It’s an awful feeling when you don't learn that someone is unhappy until after they decide to leave your organization. That’s why we have to have these conversations regularly—I recommend twice a year—so that we can work together to stay on top of what needs to change and what should stay the same. I call this process the “stay” interview: It’s how we can check in, get ahead of potential obstacles, and create space for candor and openness.
Here’s to meaningful conversations and growing together!
Big hugs,
