Thinking Inside the Box

How to Lead with Empathy in Times of Change - Andrea Herron

Matt Burns Season 1 Episode 178

In today’s episode, I chat with Andrea Herron, Head of People at WebMD, an HR executive leader, published author of "There's an Elephant in Your Office," and host of the award-winning podcast The HR Scoop. Andrea was recently selected as one of Ragan’s Top Women in Wellness and HR, an Agent of Change in American Healthcare Leader magazine, and a Top Leader in DEIB by Mogul. She lives in Portland, OR with her family and french bulldog Norman.


Our conversation began, as many do, with a candid discussion regarding how life is different today than it was in 2020. When the conversation pivoted to mental health, I was eager to learn more.


Prior to her role at WebMD, Andrea was the Vice President, Human Resources at the Oregon Humane Society. Clearly drawn to organizations making a bigger impact in society, I was curious where that inspiration came from. And how it has informed her professional practice. 


It was a really fun conversation. I learned a lot. And I hope you enjoy listening as much as we did recording it.



Andrea Herron


Andrea Herron is the Head of People at WebMD, an HR executive leader, published author of "There's an Elephant in Your Office," and host of the award-winning podcast The HR Scoop.

She was recently selected as one of Ragan’s Top Women in Wellness and HR, an Agent of Change in American Healthcare Leader magazine, and a Top Leader in DEIB by Mogul. She lives in Portland, OR with her family and french bulldog Norman.

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Matt Burns

Matt Burns is an award-winning executive, social entrepreneur and speaker. He believes in the power of community, simplicity & technology.

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Andrea Herron: One is toxic positivity. It's being aware of what that is because we can all easily fall into it. So this would look like the manager who always says, every day is a good day. Could be worse. Oh, well, what's the silver lining? Positive vibes. Only these things, right? So if you've said those things, do not panic, you're okay. The toxic part comes in when those are the only things that are allowed. You are not allowed to have a bad day, but have a human moment to just sit in it and be like, yeah, that actually was not great. Missing someone. Love it. All you.

Matt Burns: Constraints drive innovation. Hey, everyone, it's Matt here for another episode of thinking Inside the Box, a, show where we discuss the innovative ways organizations and their leaders overcome complex issues at work. If you're interested in checking out our other content, you can find us at our shiny new website, insidetheboxpodcast.com, and on all of your favorite podcast platforms by searching thinking inside the box. And if you enjoy the work we're doing here, consider leaving us a five star rating, a comment, and subscribing it ensures you get updated whenever we release new content and really helps amplify our message. In today's episode, I chat with Andrea Heron, head of people at WebMD, an HR executive leader, published author of there's an Elephant in your office, and host of the award winning podcast the HR Scoop. Andrea was also recently recognized as one of Reagan's top women in wellness and HR, an agent of change in American Healthcare Leader magazine, and a top leader in Deib by mogul. She lives in Portland, Oregon, with her family and french bulldog Norman. Our conversation began, as many do, with a candid discussion regarding how life is different today than it was in 2020. And I was curious to hear that perspective from an HR executive. And when the conversation pivoted to mental health, and in particular organizational mental health, I was eager to learn more, because prior to her role at WebMD, Andrea was also the vice president of human resources at the Oregon Humane Society. So clearly, she's drawn to organizations that make a bigger impact in society. And I was curious where that inspiration came from, how it's informed her career decisions, and ultimately her professional practice. Today. It was a really fun conversation, and I always learn a lot when I talk to Andrea. I hope you enjoy listening to it as much as we did recording it. And now I bring you Andrea Heron. This is going to be a fun conversation, Andrea. I have high hopes, and we've done this once before, so I, think it's anchored in experience. How you doing?

Andrea Herron: Doing great. So happy to be here.

Matt Burns: For those who don't know Andrea Haron, a bit about your background, your experiences, and what's led you to today.

Andrea Herron: Yeah. So I have been in HR now for a very long time. I'm one of those, unique people, perhaps, that knew I wanted to go into HR, really since college and grad school. I had an internship and was just drawn to it right away. And I am from Kentucky and moved to Portland about eleven years ago. And it took me a long time to let the y'alls and the slower speech come back through. And I think I, bring that up because I think so many of us have these backstories and places we've come from and we don't like to talk about it and we want to forget we ever came from somewhere different. But especially being in HR, I think it's important to understand that we're all people and we all come from whatever background and experience that we have. So you'll hear y'all for sure.

Matt Burns: Outstanding. This is a y'all supported zone. You're good here, right?

Andrea Herron: It really is just the best way to address a group in mind. So born and raised in Kentucky, started my HR career there, ah. At a global plastic manufacturing headquarters. So really jumped into the deep end on manufacturing and how global works. And then for family reasons, moved to the west coast and have worked in energy efficiency and nonprofit, the Oregon Humane Society, animal welfare, and now currently at WebMD, where I lead HR. And every place has been so different, but people are people in every single place. And I think if there's any profession where the people doing the work can easily move between industries and products, it's HR.

Matt Burns: I think you're right, and I think that we talk about industry differences, but at the end of the day, people are people, and there's different context. I'm curious. You have a very unique background because as I go through kind of that cv on LinkedIn and kind of work my way up the list, I see to your point, Oregon Humane Society, I see WebMD. I see a lot of organizations that are very clearly purpose driven, and I'm curious how intentional that was. And if it's intentional, what drew you to that particular line of organizations and not Wall street or large oil and gas companies, or in Kentucky perhaps maybe working for some of the large logistics companies down that part of the world, what drew you to more impact oriented organizations?

Andrea Herron: Yeah, it definitely was intentional. In undergrad, my degrees are in psychology, and so I've always been fascinated with what makes humans do what they do, what is the motivation, what is the drive? And I really enjoy making a difference in people's experience because we spend so much time at work that if I can make it better, that makes me feel good, and I know it's good for the business. And then that just kind of extrapolated out to, well, if I'm doing good work, I want the place I'm working to also be doing good things. And so there's lots of different ways you could do that. Lots of industries, but, for me, it was intentional to be a part of organizations that are doing something positive or uplifting humans or animals or health care in any way possible. So I could tie my own work to that value and mission statement, which I feel like we overlook. And it's, oh, yeah, we have the vision and the mission, and it's been on the website for five years. Nobody really looks at it. But I would challenge you to really dust that thing off and take a look, because people do pay attention. And I have seen, especially with the younger people coming into the workforce, it is even more top of mind than it has ever been. And so if you don't have a strong tie to how the work matches a, bigger vision or mission, you're really missing out on some quality candidates.

Matt Burns: Because the expectations, to your point, are changing. Employees and candidates feel more empowered to ask those questions. And let's be honest, a lot of the other factors that could come into play, things like job security or career succession, have taken a step back in more recent years as the economy has been in quite a disruption as a result of the pandemic, recessions, all those different things. But the example they've seen since entering the workforce or seeing their parents in the workforce is that didn't experience the same loyalty that perhaps we bore witness to in the generations before us. So, yeah, they're rightfully saying, okay, if you can't guarantee me 30 years of employment, then what can you give me? Because if you're not going to give me top of market pay and you're not going to guarantee me longevity, and you may or may not look at my career path with some degree of intentionality, then what I have to get is, to your point, alignment to a broader purpose so that I can at least build that alignment that maybe the organization hasn't built for me. And I think it's a really key piece, as I think it's a key piece that individuals are looking for evidence as to how organizations will treat them and value them as individuals in a world that is increasingly complex, where mental health is bubbling to the surface in ways that it hasn't before. I'm curious, given your emphasis on purpose driven and on mental health, and, on looking after the employee experience, how are you thinking about mental health in 2024, and how have the events over the last few years shifted? How you're thinking about mental health in 2024?

Andrea Herron: A lot. It shifted a lot. It's been a shared experience for me. It was a little bit, I don't know, ahead of my time, perhaps. In 2019, I published a book called there's an elephant in your office, and it's about supporting managers and leaders in the workplace about mental health of their teams, because there is a need. And I wrote it with my sister, who had her own mental health crisis, almost lost her job, and she really went through it as I was trying to help her. There was just nothing out there. And so we wrote this book together with real life examples and what to do to actually help people, and then cut to 2020. The world flipped upside down. And to your point earlier, everyone realized, oh, nothing is stable, nothing is confirmed for the next 30 years. I may be out of a job tomorrow because there's a global pandemic and everything is different. So not only were people dealing with that lack of concrete, reliable employment, we also had a full blown mental health crisis with loneliness. I mean, we have not even touched the surface of the impact of loneliness yet, but, all of the mental stressors that with good coping mechanisms, we can kind of roll with it most of the time. I'm not talking about people with clinical depression or anxiety. I mean, that obviously needs to be treated by a professional in whatever is appropriate for that person. But just the average ebbs and flows that when your world is upside down and you're alone and nothing is certain, everybody's mental health took a hit. So in 2022, we actually released a second edition of, there's an elephant in your office with updated tips, insights, and tools for being remote. Because that is another huge change that has impacted people's wellness overall. For positives and negatives. It's a mixed bag. Some people really thrive in a remote world, and some people really don't. So when I think about what has changed in the past few years, I mean a lot, how we even approach well being, meaning it's not just diet and exercise, but rather it's financial wellness. Are you stressed out about your money? It is your mental well being. It is are you connected? Do you have friends? Your emotional support? So there is just so much to be had there. And when I think about mental health now, it really is all inclusive. It's not just do you need a therapist? Although that can be a great place to start. It really is supportive management tools, just having more connection that tie to people, to the mission, to the values, and really caring for the whole person. And not just how many widgets did you produce or how many reports did you file or whatever the tactical output is of work. It really is taking care of the human that does the work. That was a lot.

Matt Burns: It's a lot. But it's also a really key differentiator as you think about a really complex problem. And to me, it's a complex problem because the question of ownership and, I know that's not a great word, but the issue of who owns this, because a lot of people are contributing to this in terms of the state of the world. Like, we talk about, mental health at work, it's not just simply in a vacuum. We're not talking about mental health. That only happens at work. People bring mental health with them. In work, out of work, it's very fluid, and if you have a bad day at home, it transits into workplace and vice versa. And sometimes with no rhyme and reason, things cross over. I think traditionally, one thing that we can look back at with some degree of, I don't want to say hesitation, but it's almost like, I wish we were more honest earlier in the process, because I grew up in a world where you weren't allowed to talk about mental health. You weren't allowed to have a tough day. You'd have to kind of like whisper, whisper asking for time off. And if it got too many people, then it's like, is Matt really cut out for this job? Is this a career limiting conversation around longevity? Jobs in leadership are really stressful. Matt, if you need a day off for stress every so often, all those questions became part of the narrative, which weren't fair, weren't accurate, and actually worked to serve people, to drive their own concerns and their own health underground, which, as we've discussed, didn't do anybody any favors. We're now in a place where employees are saying, like, hey, I've taken on more than I did before, and I'm feeling stress, whether it's work, whether it's home, I'm feeling stress. And they're asking for help from their organizations in a way that they maybe hadn't in the past because of that aforementioned lack of transparency. It's a tough question, and I don't want to put you on the spot, but I'm curious what steps that you've seen organizations take to address some of this shortfall or opportunity and to create a more supportive, employee centric environment. I get it. There's always, a constraint on resources and time. And what can organizations and leaders do to help support and create a more supportive work environment?

Andrea Herron: Welcome.

Matt Burns: Hey, everyone, it's Matt here. I hope you're enjoying today's conversation. And before we continue, I want to update you on my latest creative project this week at work. Every Friday at 07:00 a.m. Pacific Standard Time. That's 10:00 a.m.. Eastern. And 03:00 p.m.. GMT, my good friend Chris Rainey of HR leaders and I discuss the latest trending topics on the minds of executives globally, from organizational culture to technology and the future of work. We cover it all, and we invite some of our favorite colleagues to join us, from Dave Ulrich to Whitney Johnson, and executives from iconic brands such as NASA, Krispy Kreme, and WebMD. What can I say? We like to keep things interesting. And if you've been following us for a while, you'll no doubt recognize the fun partnership Chris and I have developed over years. Podcasting together. We're not afraid to be real, share our own challenges, and ask the tough questions. Joining? Well, that part's easy. Follow me on LinkedIn, click the bell icon on the top right of my profile, and you'll get notified when we go live. And now back to our discussion.

Andrea Herron: Yeah, no, I would love to answer this question. I think the very, first thing that any manager or leader can do that will make the number one biggest difference is simply to talk about it. I mean, there's so much research that it doesn't even have to be the CEO. Anyone who is in a leadership position, talking to their team, and they just mention, oh, if anyone is their own story, or they share an antidote or a tool, or they just open that conversation. Huge shift in people's comfort, because to your point, there is still a huge stigma associated with taking too much time or being too much of a burden or questioning being able to do your job. And nobody wants to be the person at work that people are whispering about or wondering if you can do your job. So the stigma has gone down. For sure. It is getting better, but we're not all the way there yet. So, other things that I do inside of my organization and when I do trainings for other companies or do, speaking engagements, things I recommend. One is toxic positivity. It's being aware of what that is because we can all easily fall into it. So this would look like the manager who always says, every day is a good day, could be worse. Oh, what's the silver lining? Positive vibes. Only these things, right? So if you've said those things, do not panic, you're okay, it's fine. You can say those things. The toxic part comes in when those are the only things that are allowed. You are not allowed to have a bad day. You are not allowed to have a human moment. You are not allowed to just sit in it and be like, yeah, that actually was not great. So it only becomes toxic when it's never allowed. So just knowing that and catching yourself can be helpful. I've also done unconscious bias training because a lot of times, these habits and things that we do, we don't even realize that we're doing. Another great tool is called the take ten check in. Super easy. In a meeting, any meeting, really could be with your manager, that they would ask three questions. How is the team doing? How are you doing and how can I help? Because when you ask how the team's doing intentionally, people are going to actually tell you how they're doing because they feel safer. How are you doing? You're going to get something, and then how can I help? If they give you something to help and you follow through, that's a huge win. And all of these things just go to show people that you're open, you care about them as a person, and that it's okay to be human, which then impacts their mental health and their cooperation and their output, and, quite frankly, their productivity, because they're more engaged, psychological.

Matt Burns: Safety just can't be overstated. And it influences everything from diversity and inclusion to innovation, to customer success. We've talked about profitability. It improves accidents. Like, the science is clear now, it's 2024, we can stop having the conversation of, is there a bottom line benefit to treating people well? The answer, yes, there is, and it's getting to the point now. And maybe this is just me, and I have the benefit of saying this because I'm not attached to a Chro's job today, but it's getting to the point now where I'm actually actively questioning the fiduciary responsibility of executives who make decisions that are in misalignment with that. Because if your job is to enrich the shareholder, and we've proven scientifically that doing the right thing for employees has a bottom line benefit, then what are we doing? And justify to me, using the same argument that was used against me for the first 20 years of my HR career, prove to me with numbers, why your idea is better. Because I have science that proves that this is actually a good idea. Those are always interesting conversations that I greatly welcome to that point. And to be fair, the roadmap that got us to this point, that helped us grow our careers, that helped build incredible organizations, that created amazing things, is not going to be what gets us the next 50 years. As the world has changed and the traditional people that we all went to to look for insights and to get their best practices are at, the same place. We are trying to figure out what makes sense and how we can do things differently. Where does Andrea go to for information? Where do you go to when you want to stay on top of trends? When you want to bounce ideas off of people, when you want to figure out what's happening in the broader world around you?

Andrea Herron: It's a great question because oftentimes we are so bombarded with our very curated news feeds that feed us what we already know or already like, it can be hard to get out of your rut and find new things or connect with different people who haven't found their way into your algorithm yet. And so it is important to call that out because you do have to be intentional. So there's always going to an industry conference or getting the newsletter, being part of that professional group, there are so many. And your local chapter and all of that. Podcasts I have found to be really great because I can listen to them on my commute. If I can go for a walk, which I highly recommend. Everybody, during your day, find 15 minutes to go, leave your space and walk around. Very, very good for your, actually, your productivity and your mental health. Podcasts are good also. One thing I have recently started doing is following leaders who I really admire that could be on any social media, could be on LinkedIn, could be on Instagram, TikTok, wherever, and you get these little bite sized doses. Personally love Mel Robbins, Simon Snack, Brene Brown, you know, some of the heavy hitters, but there are plenty more, even in your local community or industry, and follow them and see what they're talking about and then do some research on your own or if there's something interesting, join that conversation. I think it's important that we get inspired by each other and we stay connected also through our peer networks and local community. Because just like big elections, for example, is an election year. Yes, that matters. But you know what matters just as much, if not more? Your local elections. And the same thing goes for your profession. Yes, the huge national conference. Amazing. Great. But what is your local community doing that you can take back into your work and make connections and peers and friends? That is more exactly kind of where you are? And then I guess, yeah, those would be the biggest ones. I'd say it's hard, but I try.

Matt Burns: It's super hard. It's hard, and it takes a lot of time, and the answer keeps changing. So it's not like you can solve an answer, put it into your bookmark, or write it down in your notebook, and then you're good. You have to come back to that answer and say, is it still relevant today? Has the answer still changed? And I think about just the conversation around remote work. In 2019, the conversation around remote work was maybe on an exception basis with a doctor's note. And now 2020, it was, everyone go to home. Everyone has to go to the office because we can't be together in the same place. And then it turned into every organization redefining for itself what hybrid meant, which in some cases meant everyone back to the office immediately. Some cases meant no one comes back to an office ever again. But in most cases meant we're going to figure out and navigate through this period of time. Where is it? two days, three days, four days? Is it by role, is it by geography, is it by pay band? And lots of individual nuance, lots of subjectivity, lots of personal preference and bias being injected into the whole process. We ended up in a place now where most organizations have at least settled around what is today working for them. I'm not naive to believe that we're not going to see continued evolution in this space. And now there's very much, I'm just curious. Now we're four years almost into this journey. For the organizations that took a really strong stand in 2020, we, one way or another, said, this is, we're going to plant our flag. Has the data four years later borne out? What do they learn from that experience? How have they changed their thinking around this? That, to me, is a really interesting conversation because it's a very emotionally charged issue that butts up against a lot of deeply held beliefs. And it was very interesting for me to see certain leaders react to this conversation. I was blessed in that I worked in a role in the corporate world where the last five to six years, the majority of my team was remote. I was in a corporate office. But I had a very dispersed team because I took the belief of I wanted the best possible people on my team, which meant that I wasn't geographically constrained to the city in which I operated in. I wanted really great people, and that was at times challenging. It required me to be more intentional about setting meetings, having one on ones, being more responsible about task management and delegation and follow up. And for somebody like me, that's not super organized. That wasn't always easy. But I had to adapt my approach because it was ultimately where I would find the best talent and where I would be able to work most effectively with that talent, so as to not micromanage, but also to stay on top of what's happening. So they felt like they had support. To me, it's, a very easy example to articulate, and I understand why it's complicated. So I think you've illustrated well the challenges and the complexity with staying on top of trends. And I think for those folks that are interested, I will also direct them to your LinkedIn profile, the stuff that you've done, because I know you're too humble to do that yourself. So I'll put that in the podcast show notes. The work that you're doing, I'd love to learn more about, because we had a conversation offline, you're doing some really cool stuff and you're doing some really great stuff in service to other people. So what are you working on these days? And maybe share a bit more about kind of how you spend your free time.

Andrea Herron: Yeah. Well, thank you. I do a lot of things, but it's also interesting and dare I say, fun. One of the things I'm really excited about is to continue doing trainings and trainings. It feels so pedantic. Right. It's a whole shift in how we think, in how we approach employee engagement and wellness and well being. And to your point earlier, why we don't need to argue about whether or not it's valuable. It is valuable, and so now we need to do it. And what I have found is that just like normally, people who become managers don't necessarily become managers because they have all of the amazing tools ready to go. To be a manager, you have to train some things right? And HR folks and leaders. It's the same with employee culture and wellness, because we don't just necessarily, because we work in these positions, know how to do all these things. So I'm really excited to build out some training programs to offer two companies in a whole array of things, of how engagement and leadership and this unconscious bias and mental health and really empathy and leadership, I think, is absolutely one of the top skills that you need to be a leader in 2024 and beyond. And also speaking engagements and as much as I can educate and share tools and tips and ideas to help us evolve to a more modern workplace, that gets me fired up, because as we saw with the whole Covid the last few years, exactly as you said, it's these rigid old systems that are puttering along and aren't really working, but we have to have something to replace it with. And you can't just say, oh, well, that way doesn't work. Just butts and seats five days a week doesn't work without having something to offer in return. So I think that's kind of where we are and in a way that I can help people in HR, in leadership and companies kind of make that transition. And the other thing that gets me really excited is coaching and mentoring younger, well, younger in their career, regardless of their actual age, more junior professionals in HR and leadership. I really want to kind of help that next generation of professionals kind of come up in this way that they are thinking about these things for the betterment of the employee and the business, because it is both. That just gets me really excited to try and feel like I can maybe make a difference in changing even a little bit of, someone's experience that they then take on with them in their journey.

Matt Burns: So we started this conversation by you sharing that you're one of the few people that intentionally chose an HR career path. You're definitely the only person on this podcast that had that, story. That being said, I'm curious, what advice would you give to an HR professional who is maybe just beginning that career, and how would that advice be different than the advice that you were given when you started your own journey?

Andrea Herron: I think the best advice I could give to someone more junior in their career is to be open to whatever opportunities, and challenges come your way. And that's not shocking or something no one's ever heard, but you really, especially in HR, you never know what you're going to get. And if you can keep a mentality of a learner's mind, a beginner's mind, being curious and being interested in finding out, oh, that went horribly wrong, how could we do that better? And, learning from that, who knows what direction you could go in? HR is a very big profession, right? So, I mean, you have to kind of figure out at first, which part are you even interested in? Maybe if you're a generalist, what are you more drawn to? Is it benefits or recruitment or employee relations or. You kind of have to explore a little bit of what lights you up, but follow that and then be open to taking on an extra project as a stretch or growth. And don't expect that you have to know it all right away. And I think what I know now that I wish I had known in the beginning is how important it is to have some type of mentor. I don't think we talk about that enough. I had a wonderful first boss and I'm still in touch with her and I'm so grateful for everything she taught me. But that was just happenstance, right? I didn't seek that out, and it has been really important for my career development and growth. So if you don't have someone you're looking up to, you're following, you're connecting with. Don't be afraid to send that message or make that ask. Hey, would you mind to meet for coffee for half an hour? Let me pick your brain. I'd love to hear your story. It is intentional, but those relationships are incredibly important for getting you on the right path.

Matt Burns: I couldn't agree with you more. I am, a product of the mentors that have spent the time and their own valuable time with me, and allowed me to make mistakes and learn and ask silly questions and all the things that you do when you're beginning in your career. And I think to your point, HR is such a varied and interesting profession that I don't think a lot of people have visibility into, especially at the large enterprise level. The amount of different career paths and skill sets that are required in HR today. You can go deep down recruitment and learn around sales and around more relationship oriented type work and around talent assessment and how to embed that with technology. You can get involved with learning and development and go down the learning path and focus on skills development and coaching and instructional design. You can go into employee relations, get into labor law and labor relations. You can get into comp and go down the path of, technology data. I can keep going and going and going. That's what excites me about the profession is the ability to almost be a swiss army knife of sorts and be able to interact with so many different intelligent, passion, purpose driven professionals. It's a real privilege and it's been a great privilege as well. Chatting with you, Andrea, today. I always enjoy our conversations and I'm going to link, as I mentioned, all the details for yourself, all the things you're working on in the podcast show notes. But just thank you again for the chat today.

Andrea Herron: Thank you. I appreciate you having me on. It's always such a delight.

Matt Burns: Ento HR is a digital transformation consultancy working at the intersection of strategy, technology and people operations. We partner with organizations, private equity and venture capital firms to accelerate value creation and identify the organization's highest leverage initiatives. And this can take place in many forms, from strategic planning and alignment to technology procurement, implementation and integration, along with organizational design, process reengineering and change management. With our proven track record of working with complex, high growth organizations, we provide a lens that goes beyond the balance sheet, increasing enterprise readiness, resilience and value. For more information, check us out@bentohr.com.