May 25, 2025

You Can’t Check a Box for Culture: Interview with Shawnee De Anda, Chief People Officer of Thriveworks

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Adam Mendler

I recently went one-on-one with Shawnee De Anda. Shawnee is the Chief People Officer of Thriveworks and was previously the Chief Human Resources Officer of Signature HealthCARE.

Adam: What are the keys to leading in a remote environment?

Shawnee: Multiple forms of communication, multiple ways to get in front of your workforce. We do ENPS surveys. We do a Great Place to Work survey. We do the ENPS every quarter. Their feedback is so important, so we know what we could do differently or better. The Great Place to Work survey is very detailed and gives us phenomenal information as well. But I think you have to ask. You have to probe. You can’t assume it’s your way or no way. And so we’ll often ask our workforce, how do you want to be communicated with? Are there things that are important to you that maybe we haven’t touched upon? If we’re doing a town hall, for example, we’ll solicit topics like, what do you want to hear about? What do you want to talk about? It’s important to hear from them, to listen to them. You can’t assume you know what needs to be addressed or discussed.

Adam: What are some of the pitfalls you’ve faced in trying to build culture for a remote-first company, and how have you been able to overcome them?

Shawnee: Yeah, it’s not easy. I’ll be really honest. I will share, though, that I do feel like we have a culture of empathy, a culture of feeling. From a business perspective, is that the most important thing? Does that impact the bottom line? I think it does. I think in the long run, it absolutely does. Building the culture is based on employee feedback and the overall employee experience.

Let’s say you’re sitting in the ivory tower. I think sometimes people see that C-suite title and assume you might be out of touch. But it’s our job – whether you’re in the C-suite or any people leadership position- to have consistent and regular communication with your employees from top to bottom, to find out what’s going well and what’s not.

There’s this book I read years ago by Quint Studer called Rounding: Rounding for Success. It’s basically about asking three very generic questions: What’s going well? What could we do differently or better? And is there anybody I should thank or congratulate? By doing those things, you find out more about what’s going on in the organization than you would by prepping a board deck. It’s about getting real-time, hands-on, frontline feedback and understanding their experience and perception of the organization.

It takes a little more effort. It definitely does. You have to be proactive. You have to have that outreach with your workforce. We also do virtual happy hours. We do virtual trivia. We try to build community, even outside of work. We want to get to know everybody. We have this “Mandatory Fun” chat, which is awesome. I know who can bake, who has gigs on the weekends, who has amazing photography skills. It’s just really neat.

In a remote environment, it’s a little different, because people might feel braggadocious throwing something into a chat-like, “Look at these great things I’ve done.” There’s that old saying, you don’t want to virtue signal. Sometimes when people first join the organization, they almost associate some of our chats or the online ways we try to drive engagement and build community as a social media play. But once they get comfortable, it really helps them open up: sharing about themselves personally and celebrating professional and personal wins. It goes a long way. You’ll have people from the West Coast to the East Coast cheering you on. Asking, “Hey, how about that win?” or “How’d your kid’s soccer game go?” That connection really matters.

Encouraging active participation? Sometimes we have individuals who haven’t participated in a while, so we ping them in the chat: “Hey, how was your son’s soccer game? I know you had a tournament this weekend.” That encourages them to respond. So sometimes you have to initiate it yourself. But once people realize it’s for all the right reasons, it becomes easy for them to engage and participate.

It took me a minute to get comfortable with some of the ways we communicate and solicit engagement. But once I was, it became second nature. It becomes exciting. It’s an easy way to know who your peers are and who your team is. We know what our mission is, but each team and department might have different priorities, and this helps build engagement across all of that. It’s important. It’s not easy. But thankfully, we’ve had a lot of people who felt it, who knew it, and thankfully, we get feedback from our workforce that really tells us, “Hey, it would be beneficial if we could do A, B, or C.” All the things we’ve implemented to drive engagement and build culture in a remote environment were based on employee feedback: what they wanted, what they preferred, and what they’d like to see.

Adam: Do you have any other tips on how to lead in a remote environment?

Shawnee: Yeah, I think it’s important to be real. Be your authentic self and still actively listen in a remote environment. You can’t just check a box for engagement. You can’t check a box for culture. It has to be something you really care about and want to positively impact. Because if you’re disingenuous, remote or in person, people feel it. They pick up on it.

Adam: When you’re working in a healthcare environment, difficult conversations are inevitable: delivering bad news, communicating a diagnosis, handling patient complaints, discussing treatments. What advice do you have for anyone in the field of healthcare on how to have the difficult conversations and have them effectively?

Shawnee: That’s a great question. Dealing with difficult conversations in our largely remote organization requires a blend of communication skills, empathy, and clear strategies to ensure the conversation is productive and supportive, especially for people managers and clinicians. Our clients want to know what the next steps look like, and they want empathy along with direction.

We work with our people leaders on building empathy and emotional intelligence through active listening. We use empathy exercises – even with clinicians- to understand how tone comes across, as well as nonverbal cues. We also encourage making sure that difficult conversations happen in the right setting. It should be a safe space for everyone involved. That might mean scheduling a private meeting and ensuring confidentiality. There’s a time and place for everything.

Thankfully, most people leaders have emotional intelligence and know how to navigate those conversations. Many of our clinicians work remotely, and some see patients in person, so picking up on nonverbal cues is critically important. Empathy is something our clinicians have in abundance, and we learn from them what best practices look like when delivering difficult conversations.

Adam: What exercises allow you to develop empathy?

Shawnee: They’re all role-playing exercises, which can be extremely comfortable and fun for some people, and extremely difficult for introverts or those who have a hard time. But they’re basic role-playing activities. For example, if we’re preparing for a difficult coaching conversation, our HR team will partner with people leaders on tone and delivery, acting like they’re the employee being coached. Mostly role-playing.

One important thing is not to sound robotic or scripted. Be you. Be who you are. If it’s off the cuff, that’s fine. A lot of times, managers have scripts during difficult coaching conversations, and it’s like no, be you. Be vulnerable. These conversations aren’t comfortable, whether you’re the coach or the one being coached. But speak to that individual the way you normally would. It doesn’t have to be overly formal or different from your usual day-to-day conversations.

You’re absolutely right: practice makes perfect. But you’ll have one-off meetings where you get thrown off or receive an unexpected question. That’s when it’s okay to be vulnerable and honest. If you don’t have an answer, let them know you’ll follow up. What’s important is being authentic.

When you’re overly scripted, it can make the employee feel like the relationship isn’t what they thought it was. Maybe they thought they had an open relationship with their leader. Imagine working with someone for two or three years – sharing wins, family updates, personal moments – and then they show up to a difficult conversation acting robotic and scripted. It’s very off-putting.

You have difficult conversations because you want the person to succeed, not fail. But if the conversation feels scripted, it could immediately turn someone off. They might leave the meeting and go straight to LinkedIn to look for other jobs. So how you deliver the message, even if you’re uncomfortable, is critically important. That delivery can determine whether someone can turn around their performance.

You need privacy. In skilled nursing, for example, there are rooms for confidential conversations. Face to face, you can read body language – head turns, leg bouncing, clenched fists- and adjust. In a remote setting, it’s the opposite. We’ve had coaching conversations where employees turn off their camera, and we can’t see if they’re engaged or not. We lose those nonverbal cues.

Sometimes employees ask to record the conversation, which I’ve never had happen in person, and that can be off-putting. So it’s different. There are best practices for both settings, but each is unique. You just have to prepare: what could go right, what could go wrong. If it’s in person, do you need someone nearby in case things get heated? If it’s remote, and someone logs off or goes off-camera, what are the next steps? You have to plan for best- and worst-case scenarios.

Adam: What body language should you try to express and what body language should you try to avoid?

Shawnee: You always want to make eye contact, be empathetic, and show that you care and want the person to succeed, whether it’s a difficult conversation or not. From a remote setting, make sure your surroundings are quiet, you’re not distracted, and you’re not distracting the person you’re talking to.

The number one piece of advice is eye contact. Second is active listening. You have to really hear what someone’s saying, not just run through a checklist in your mind. Body language while actively listening can sometimes seem closed off, so prepare for that. If you’re taking notes, tell them: “Hey, I’m taking notes, so don’t think I’m multitasking or answering emails.” Those little things help.

Adam: Do you have any other best practices to follow or pitfalls to avoid for those who have to have difficult conversations in this environment?

Shawnee: I’d say make sure you leave time for questions. Don’t dominate the entire conversation. Make it two-way. Ask for feedback. If it’s an employee who isn’t meeting performance goals, ask why. It’s also a great time for leaders to be reflective. Could you do something differently or better?

I often share that people leaders need to be chameleons for their teams. It’s not the team’s job to deliver their work in the exact way we prefer. I had a leader in the past who insisted on a specific font. If people didn’t use it, that was a problem. But that’s such an easy thing to change. Yes, leaders should set expectations, but we also have to make sure we’re setting our teams up for success.

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Adam Mendler

Adam Mendler is a nationally recognized authority on leadership and is the creator and host of Thirty Minute Mentors, where he regularly elicits insights from America's top CEOs, founders, athletes, celebrities, and political and military leaders. Adam draws upon his unique background and lessons learned from time spent with America’s top leaders in delivering perspective-shifting insights as a keynote speaker to businesses, universities, and non-profit organizations. A Los Angeles native and lifelong Angels fan, Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders.

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