Erin Diehl Of improve it!: 5 Ways Empathy Will Affect Your Leadership

An Interview With Cynthia Corsetti

Empathy will create change and a ripple effect in not only your life, but in the lives of others. So, if you’re able to help a human being, one human every single day, you’re living out your purpose. And when you’re living out your purpose, you are in service to not only others but to yourself. It’s going to affect you and change your life as well as the people around you.

Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Erin Diehl.

Erin “Big” Diehl is a Business Improv Edutainer, Failfluencer, and Keynote Speaker. Through a series of unrelated dares, Erin created improve it!: a unique professional development company that uses improvisational comedy and experiential learning to sharpen leaders and teams so they can thrive in ever-changing environments, and do it with a whole lot of laughs along the way.

Erin Diehl is a graduate from Clemson University, a former experiential marketing and recruiting professional, and a veteran improviser from the top improvisational training programs in Chicago, including The Second City, i.O. Theater, and The Annoyance Theater.

Having spoken on global stages with companies, including Amazon, LinkedIn, McKesson, and the Obama Foundation, Erin has an energy and message to share with the world that creates lasting ripple effects for change. As a graduate of the Goldman Sachs 10,000 Small Business Program and member of The Chicago Innovation Awards Women’s Cohort, Erin is a living testament to the power of life-long learning, and how working to understand ourselves helps others to do so, too.

Erin is the proud host of a Top 1% Global Podcast, The improve it! Podcast, which you can find anywhere you listen to pods! She is also a first time author to the Amazon Best Seller & Top New Release book: I See You! A Leader’s Guide to Energizing Your Team Through Radical Empathy.

Among her many accolades, Erin is most proud of successfully coercing over 35,000 professionals to chicken dance.

When she’s not playing pretend or facilitating, she enjoys walking on the beach with her husband, son, and eight-pound toy poodle, BIGG DIEHL.

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I fell into this career path In my twenties. I had always known that I wanted to help people, but I just really wasn’t sure how to do that. And when I walked into my very first improv class, I knew at that moment that that was where I was meant to be, that I was able to fully be myself. I also knew that this art form had a healing modality to it, so I stuck with it. I continued my training at three different improv schools, and it became clear to me that I was going to use improv as a teaching tool to help other people become their highest selves through play.

This took many different shapes in the beginning, but what we’ve created here at improve it! is a professional development company that uses laughter, experiential learning, and play to help people tap into the highest versions of themselves possible. I feel so grateful that I get to do what Jen Gottlieb says is labeled as hope, H-O-P-E, which is, “Help One Person Every Day.

Can you share the most interesting story that happened to you since you started your career?

Yes, it was when my team and I were asked to be facilitators for the Obama Foundation’s first ever training day. We worked with a large group of about 250 folks, and within that large group was one of our very own, our VP of Client Experience, Jenna McDonnell.

The groups were challenged with putting together a plan for positive change in the city of Chicago, and each group had to vote on the best idea. Jenna’s group voted her idea to be the best. They then had to present this not only to the room of 250 people, but to the former president himself. I watched that day change Jenna’s life. She was a timid intern who blossomed into this confident professional, and it’s been one of the greatest joys of my career to watch that transformation. I do know that that day changed her life because Jenna saw for herself that if she could present to a former president in front of 250 people and across several media outlets, she could do anything. And she sure has.

What do you think makes your company stand out? Can you share a story?

improve it! uses improv comedy to train professionals to be their highest selves, and we really tap into this art form as a method for teaching people whatever particular soft skill that the workshop calls for. For example, in our Taking Initiative & Creative Risks workshop, we do an activity called “The Gift” where partner A pantomimes and hands an invisible “gift” to partner B. Partner B then names the gift anything they want by saying, “Thank you for _______.” Then partner A justifies why they gave them that gift, “You’re welcome, (reason they gave them that gift.” This activity uses improv as its training tool to teach participants why creating a safe space for new ideas to be shared is an essential first step, because without a safe space in place from the beginning, lots of folks won’t feel comfortable enough to share in the first place.

We have had so many case studies of companies continuing to use the training tools that we teach them long after their workshop is over, especially the central tenet of “yes, and” to expand ideas not only within their teams but their organizations as a whole. One company that comes to mind in particular is American Marketing Association. We started working with them, and almost from day one they adopted “yes, and” and made it a core value of their organization.

So when you walk the halls of American Marketing Association, you’ll see this “yes, and” core value on its conference room signs and you’ll see it plastered around the office. I think this pillar of collaboration and how it sticks with our clients is what sets our company apart from other L&D organizations.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I think one of the first traits that has been the most instrumental to my success is determination. For me, that really came through in the pandemic. I knew we had built something so important and mission-critical to the world that I would do anything to see it come to fruition. I was determined to do anything to make our mission come alive.

This determination helped me to pivot the business over and over again to create virtual opportunities for all of our improv professionals, for our clients, and created new service offerings and ideas that we could use to not only impact leaders and their teams, but to bring improv to different parts of the world. That determination allowed us to work with partners globally, not just locally, and expanded our reach beyond Chicago, which is where we were at the time.

The second character trait I think is empathy, which I talk a lot about in my book. I See You for me is really about understanding the whole person, the human being, not just the human doing. And I think that has come into play so many different times with the women of the internal team here at improve it!. We love anyone who doesn’t identify as a woman to be clear, we’ve just always hired women and have this really awesome group of women leading the internal team here. I see that empathy come through not only in how I lead the team, but how they lead themselves, how they lead each other, and how they empathize with our clients.

I’ve had clients say to me before that they thought that our VP of Client Experience Jenna was the founder of the company or they thought our VP of Talent Cristy was the founder of the company. That’s the highest compliment that I as a business owner could ever receive is that people feel so seen, heard and valued by the team that we’ve created here.

I think the third characteristic is fun. I think that if you measure the amount of success you have by the amount of fun you’re having, then you’re living a life filled with joy and you magnetize and attract so many things to you. I have many stories about fun’s role in my success, but one of my favorites is the fact that we’ve trained over 35,000 people to chicken dance — a fun movement component to all of our events. Having fun is our calling card, and we make sure to incorporate it into our day to day.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

I’ve had to make a lot of hard decisions, but I think probably the most pinnacle decision I had to make was in 2020 when I had to choose to either close our doors or to pivot our completely in-person, completely face to face, completely human to human professional development company, completely virtual.

The easy route would have been to say, hey, it’s been a good run. We’re gonna shut her down for a little bit and we’ll reopen when things come back, which at the time we had no clue would take two years. The harder choice was, hey, how can we reconfigure everything that we’ve built into a virtual format and do this in basically a matter of weeks in order to survive? And I will say that was one of the hardest times of my life.

I had to make many decisions in the moment, even though I wasn’t sure what the right answer was going to be. I was full of uncertainty, but I continued to follow my gut.

My team continued to follow their guts as well, and together we pivoted our way through that pandemic and we’re better for it today. We now can do any offering that we have completely in person or completely virtually. And they are just as impactful in either format. That showed me that I am so capable as a leader that I need to continue to trust my own tuition, my team’s intuition, and that I surrounded myself with the right people who believe in this dream and who stood by it.

And through that we’ve created and attracted so many amazing individuals to our company and have gotten to work with some of the coolest companies all over the world because the pandemic actually expanded our reach globally, which was awesome. So those challenges actually led to a silver lining and I found the lesson in them and have taken that with me throughout my life.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

I believe that empathy is not just walking in somebody else’s shoes, it’s putting on a pair of their Nike dunks, walking in them for the day, getting a blister and handing them back to the person that you got them from and saying, wow, I see you. Now, I think it is a vital trait for leaders to possess empathy in today’s work environment for several reasons, but one of the main ones being that our lives have significantly changed post-pandemic.

Leaders are just now understanding the importance of seeing the human being, not just the human doing. We see the whole person bringing themselves to work and the challenges that they might be facing in their personal life.

When we are able to really put ourselves in the shoes of the person who we’re talking with, we’re able to see that person, not just for the person doing a transaction at work, but for the entire human being. The entire human being who’s having a human experience–all of the things that they’ve been through, all of the things that they are going through, and how we can help them get through their future.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

I’ve had so many empathetic conversations. I think one of the great things about improvisers is that we are taught to be empathetic on stage in order to make scenes go forward, we’re taught to “yes, and” the person before us by adding to what that person is saying and not negating it.

And that’s essentially what empathy is. It’s a “yes, and” exchange. It’s a, “Yes, I hear you. I acknowledge what you’re saying and feeling. I see you, and let me add to that.”

Let me take what you’ve said and really process that, not negate it, and add to it so that we can build this beautiful scene together. I don’t have one personal experience that comes to mind when thinking about how it can impact our organization, but as a whole, I think that one of the most beautiful qualities of an empathetic leader is that they truly listen.

And I can say for a fact that the reason that our VP of Talent has been here for ten years is because we have a kind, loving, and empathetic relationship where we truly listen to each other.

Empathy is why our VP of Client Experience has been here for seven years and is taking a seven year sabbatical. We’ve both empathized with each other, we see the human being not just the human doing in each other. I’ve listened to her as she’s grown in her career, she’s listened to the guidance I’ve provided, and she’s also listened to me as a leader in my own personal situations.

Anyone who’s been a part of this organization for any period of time–we have internal team members who have been with us anywhere from two to ten years–knows how large of a role empathy plays. They can feel it. And I think that’s a great testament to them feeling seen, heard, and valued–they feel like they can show up.

On the flip side too, there have been instances where I haven’t been an empathetic leader and my team has felt comfortable enough to have conversations with me. That’s the thing about having an empathetic culture–if it works, it also self-corrects. So managing up, managing down, leading up, leading down–it all comes full circle when empathy is at play.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

I think this is a really hard scenario, especially for empathetic leaders, because a lot of times empathy sometimes could be what Kim Scott who wrote Radical Candor calls “ruinous empathy.” You don’t want to be a leader who is too empathetic because you still have to make decisions that are the best for the individual and the best for the business. So, I think a lot of times making a tough decision that might not be popular for the team is one of the hardest parts of being a leader. You can’t please everyone.

But one thing that you can do is make sure that the people who you are making the decision for feel seen, heard, and valued and that they at least know that you considered their part of the conversation when making that decision. So, bringing that to the table, it would sound like, “I know this decision isn’t super popular. I heard Susan say xyz and Bob say xyz, so here’s where we’re going as an organization.” This goes such a long way, it may not be the decision that everyone wanted, but the fact that you named Susan and Bob’s thoughts/concerns is what’s important. They know that they were listened to.

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

Empathy is understanding the individual and seeing all parts. Sympathy is I think more of a grievance with that person. It’s really taking on the energy. And that’s something that I think is really important as a leader.

Empathy is seeing the full picture and if the situation calls for it, using this to help come up with a solution. Sympathy is seeing the full picture and taking on the energy, but not coming up with a solution.

When you can see the full picture from a bird’s eye view as a leader, you’re having more of an empathetic stance, and you’re able to make decisions. But if you take on that energy and have too much sympathy for the person you’re leading, you tend to get in the weeds and it can be difficult to find a way out.

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

This is a great activity called “Empathy.” You can try this as an activity and then use it and apply it in your real life. Let’s say Susan is having a challenge. You would listen to Susan’s challenge and then repeat back the challenge in the first person as if you are Susan. What does this do?

It allows you to filter Susan’s issue through the first person as if you are going through the challenge. Speaking in the first person about the challenge takes you out of the equation, drops Susan in, and when you remove yourself, you’re able to see the full human having the experience, so you’re able to create change and not let your own emotions get in the way.

How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?

Empathy is the backbone of ensuring that all feel seen, heard, and valued. It’s ensuring that people feel safe. They feel like they belong and they feel like they matter. That’s what the root of empathy is.

It is saying I see you, you matter, you are worthy. You are a human being, having an experience. I see and hear that. And here’s the “yes, and.” Here’s how I’m going to guide you through it. Here’s how I’m going to hold your hand and help create an outcome with you. It’s not skipping right over the outcome. It’s seeing the person going through the experience and then guiding them to an outcome that helps them, the human being, as well as the population as a whole.


Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?

1. It will make you a more well-rounded human being. I say that because when you lead with empathy, you’re not just leading from your ego, you are leading from your higher self because you are in the act of service.

2. Empathy will create change and a ripple effect in not only your life, but in the lives of others. So, if you’re able to help a human being, one human every single day, you’re living out your purpose. And when you’re living out your purpose, you are in service to not only others but to yourself. It’s going to affect you and change your life as well as the people around you.

3. Empathy is going to make you live longer. Instead of getting stuck, empathy is always going to drive you forward so you’re saying, “Okay let’s do it. And now let’s try something else.”

4. Empathy allows you to constantly be innovating as a leader. If you’re not helping other people and coming up with solutions to problems, then you’re not doing the job of a leader. Part of your job is to innovate, to create change, and to help solve problems. So more empathy actually leads to more innovation.

5. Empathy makes you a sticky leader. It makes people want to be around you because they feel seen, heard, and as if they matter, so it helps with staying power, with people staying in their jobs, being fulfilled, feeling seen and heard, makes them want to show up and be more productive.

6. Empathy is the number one tool that I know that will give you a productive team. Because when people feel seen, heard, and valued, they want to show up. When they want to show up productivity rises. And then the individuals around the organization and the organization as a whole thrive.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

This goes back to what I mentioned earlier about ruinous empathy based off the book Radical Candor by Kim Scott. Kim states “Ruinous Empathy™ is “nice” but ultimately unhelpful or even damaging. It’s what happens when you care about someone personally, but fail to challenge them directly. It’s praise that isn’t specific enough to help the person understand what was good, or criticism that is sugar-coated and unclear.

Ruinous Empathy is seeing somebody with their fly down, but, not wanting to embarrass them, saying nothing, with the result that 15 more people see them with their fly down — more embarrassing for them. So, not so “nice” after all.

You can address this by being empathetic, challenge directly, and give radical candor. Kim Scott says it best! She’s a colleague and has been on our podcast, the improve it! Podcast two times. Ruinous empathy is not god

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

Oh man. Well, I’m really trying to go to bed earlier and get better sleep. But if I am staying up late and ruminating on an issue, it’s probably more an external problem than an internal problem. And I think that external problem is really trying to attract the right people to our organization, really finding the partners that align with our mission and our core values and doing that in a way that is working smarter, not harder.

The quality of product, the quality of humans that we have in our business, those things are solid. I feel so good about that and the people who run our business, facilitate our offerings, the offerings that we share, I mean, I feel great about, but it’s really getting our name out there that keeps me up.

And how do those things influence my daily decision-making process? They’re everything I think about–what’s the fastest way we can reach more people with the right message at the right time. That’s what I’m constantly thinking as we’re seeking new ways to market, innovate, and bring people to us through prospecting sales conversions and leads.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

It will be called the I See You Project. This is a project that I’ve thought about for a really long time. Essentially, it’s a nonprofit that is in conjunction with the book that I wrote called I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy.

It’s a project that allows humans in different communities all over the United States, potentially all over the world, to nominate people in their community who are doing great work. People who are leading with empathy, who are giving to their community and of service, who care for the people that work for them, who are great leaders and coaches and just need to be recognized.

The I See You Project will recognize those people. It will bring awareness to the good that they’re doing in their community and it would give them something that they can pay it forward with. Maybe it’s an experience for them or maybe it’s just a celebration of them in some way, shape or form. But that is the next idea!

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Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.