Stop Overusing Empathy: Balancing Empathy And Boundaries With Whitney Sullivan

by | Mar 16, 2023 | Podcasts

SWGR Whitney Sullivan | Balancing Empathy


All good things have their limits. Even too much empathy can hurt us. In the world we live in, empathy has become more important than ever, especially for leaders. However, it is easy to fall into the trap of being too empathetic. This episode’s guest sheds light on how to rethink empathy and find the balance between too much and enough. Elizabeth Bachman interviews leadership coach and keynote speaker, Whitney Sullivan, to talk about how to set boundaries, manage empathy, and identify where it is useful and where it is not. Whitney tells us about the struggles faced by many female leaders as they grapple with the societal pressure to be codependent and self-sacrificing. She then offers a new perspective to help us shift our mindsets on empathy when it comes to delegating, giving critical feedback, and even building relationships with your team. She helps us reel back from giving so much of ourselves that we get burnt out. This conversation reminds us of the importance of boundaries as leaders. That way, we thrive not only in our roles but also in helping our teams succeed.

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Stop Overusing Empathy: Balancing Empathy And Boundaries With Whitney Sullivan

Before I get going in the interview, I’d like to invite you to see where your presentation skills are strong by taking our free four-minute assessment at That’s where you can see your skills are strong and perhaps a bit of support could get you the results you need and the recognition that you deserve.

My guest is Whitney Sullivan who reached out to me. She said, “Do you want to talk about the mistakes you can make if you are too empathetic?” She then described a lot of things. I thought back to my early days as a leader and realized I made all those mistakes. It was good to be reminded of how to set boundaries, how to manage empathy, where it’s useful and not. It was a very useful conversation.

Whitney’s official bio is that Whitney Hinshaw Sullivan is a leadership coach and keynote speaker with a heart for beginners. With a background in leading fitness, wellness, and student leadership programs in higher education, she learned the hard way that transitioning from individual contributor to leader requires a lot more than a change of title.

Whitney offers the coaching she wishes she had received so that leaders can show up with clarity, confidence, and resilience. She lives in Bozeman, Montana with her husband. She’s also an avid reader, outdoor adventurer, and cycling instructor. You will find this a very useful conversation. On to the interview with Whitney Hinshaw Sullivan.

Whitney Sullivan, welcome to the show.

Thanks, Elizabeth. I’m happy to be here.

I have to applaud you because you are one of the few people who are speakers that wrote to me. First of all, you said you tune in to the show. I was very happy about that. I was like, “People are tuning in.” You said, “I have something to say,” and you put yourself forward, which was perfect. I went, “I have made all those mistakes. Let’s talk about it.” Before we get into the perils of empathy, let me ask you who would be your dream interview? By that, it is someone who’s no longer with us. Who would it be, what would you ask them, and who should be listening?”

This was such a good question to reflect on. I had a hard time picking one exact person, but I kept coming back to groups of people. I love historical fiction, period pieces on Netflix, and documentaries. The group of people I kept thinking of was women in history breaking barriers. A book I read in 2022 was called The Rose Code. It was this historical fiction book by Kate Quinn. I recommend it. She told the story of three women who were code breakers during World War II, or they worked for the people doing the code-breaking. One of them, in particular, was a code breaker. They worked in a place in England called Bletchley Park that no one knew was breaking the German Enigma Code.

Those were the types of people I kept thinking of. I realized what they had in common was females breaking barriers, especially in World War II. Here are women going into the workforce doing something that’s traditionally male-dominated. I would be so curious to know their experience of showing up and serving in that way.

Especially after World War II, that’s when things started to shift for women in the workplace. They were the pioneers. I would want to sit down with them and say, “Tell me your perspective. Tell me what it was like to show up in this role every day. Tell me moments when you had to have a lot of courage. What would you say to someone down the road that also needs to show up to a space where they might need to have a little courage?”

One of the interesting things about this conversation is that you try to think about code-breaking. Women think differently. Certainly, women communicate differently. A huge part of the work that I do is helping men and women learn how to talk to each other because it’s the same words but they’re two different languages. The male code breakers would’ve attacked the problem in a different way. I suspect that the women would have seen connections that the men wouldn’t have, but nobody talks about them.

That’s why I loved that book so much. It was this fictional representation of real events that’s like, “I’d love to get in there and hear what went down in those circumstances.”

I’m going to have to do some research about that. Let me ask you. What struck me by the talk that you proposed was what the limits of empathy are and where empathy gets us in trouble. When you started talking about it, I thought, “My first years as a boss, I made all those mistakes.” This show is for female leaders. Some of us may have learned that lesson, and some of us may need to be reminded. Talk to me about empathy and boundaries and how they fit together.

First of all, I would recommend to any female leader looking to learn more about emotional intelligence, empathy, or emotions, to look into Brené Brown’s work and Atlas of the Heart, which I’m going to talk about here in a second. She said so beautifully in her HBO series that she did on Atlas of the Heart that empathy is not empathy without boundaries. Empathy without boundaries is enmeshment. Those are her words, not mine. She said so in such a clear understanding way that with empathy, we have to know where others end and where we begin.

SWGR Whitney Sullivan | Balancing Empathy

Atlas of the Heart: Mapping Meaningful Connection and the Language of Human Experience

When it comes to being an empathetic leader, especially as a woman, how we know and establish that is by making sure that we’re empathetic, we set boundaries, we establish clear expectations, and we’re willing to give critical feedback. Empathy doesn’t mean we don’t do those three things. Empathy is how we show up to those difficult moments. It’s a compassionate stance or being curious, or it’s a skill in perspective-taking. Something that I learned, especially as an emerging leader, and I work with emerging leaders in my leadership coaching practice, something that they learn is that we have to be empathetic and we have to set boundaries, establish clear expectations, and be willing to give critical feedback.

One of the things that make me think about that is that women are often trained to be codependents. Lots of people are codependent, but women are trained to put others second.

We are self-sacrificing.

I don’t think anybody does it on purpose. It is society. Those are the messages that we get, certainly from the stories we grew up on and all of that. It’s good to have emotional intelligence and to put yourself in the shoes of others. That’s rule number one in my book. For the strategy of somebody who’s trying to be visible and valued, it is to know your audience and use strategic empathy. It’s my signature term.

That’s a great term.

You are empathetic. You put yourself in the shoes of the people you’re talking to, so you know what they’re looking for. You can talk to them in a way that they will understand instead of expecting them to think the same way you do, but to be strategic about it. That’s the part that people forget. Strategic empathy is you are doing it A) Because it makes you a better person to understand where someone else is coming from, but B) To use it as a strategy so you can reach them where they are.

I love that. We need to repeat that. It’s a strategy to meet someone where they are. That’s such an excellent use of empathy as a tool in leadership and a strategy to meet people where they are. That’s beautifully said.

Empathy is a strategy to meet someone where they are. Share on X

You have to lead. That was something that took me a while to learn when I was running the opera company. I founded an opera company. In learning how to be a boss, I wish I had somebody to help me. We’re going to talk later about mentors, but that’s the other thing. I thought I had to do everything myself. I’m sure you go through that. How do you approach a client or a leader who believes that if they say they need help, that’s a weakness?

The very first thing that I do with every client is take a deep dive into self-awareness, into what drives you, and into what blind spots are. I use an assessment. It’s called the Enneagram assessment. I don’t know if you’re familiar with it. What I like about this assessment is that it’s not warm and fuzzy. It will tell you your strengths, but it will also tell you your blind spots that can come up.

For example, for leaders, one’s vulnerability is to be avoided at all costs. It’s a big mindset shift to realize that asking for help is a form of strength. It’s important to educate clients on what I like to call The Vulnerability Blind Spot. That’s where we’ll offer people help all day long. That’s the strength in us, but the moment that I have to ask for help, that’s the weakness in me. There is a quote by one of my role models early on in coaching. Her name is Mo Kerik. She’s a great thought leader on people leadership. She has this beautiful quote. She says, “Courage and vulnerability are twins. They always go together.”

I work with clients on shifting their relationships from vulnerable moments to courageous moments. We can’t engineer the vulnerability out of our experiences, but we can begin to build tools that help make courage a little more accessible in that vulnerability and a little bit more manageable. I might ask a client because it’s vulnerable to ask for help. That’s the empathetic piece. I’d be like, “I’m curious. What would make that feel more manageable? What would allow you to access the courage to ask for help a little bit more?”

One of those things is self-awareness. I also have noticed in new leaders the compassion point. Usually, by the time they’re working with me, they’ve had that moment where they’ve realized, “This is a lot harder than I thought it was going to be. Leadership, leading people, and building these relational skills with people are a lot harder than I thought it was going to be. I need to ask for help.”

There are lots of things that go into supporting someone and accessing that courage, but self-awareness is one. It’s understanding what makes you feel most vulnerable and how you can then turn that into a moment for courage. Have you had that point where you realized, “This leadership journey is a lot harder than I thought?” Sometimes, maybe a failure happened. Something happened and they realized that they didn’t have a choice but to ask for help.

Here’s another thought. A couple of things came up as you were talking about that. One is if you’ve ever worked in an organization and you are stuck with a micromanaging person or the person above you is micromanaging you, it’s probably because they haven’t learned how to let go. If you are that person, learning how to delegate is so important. If you don’t delegate, your people will hate you.

I love that clarity.

I’ve been on both sides of those.

Delegating isn’t a spur-of-the-moment thing. It’s a skill that takes empathy to learn how to use. If you’re going to delegate well, you have to set boundaries well. You have to be good at setting clear expectations. Delegating is going to require giving people critical feedback. If something is not going the way that you wanted it to go and you delegate, you’re going to have to practice your empathy. Put them in your shoes and give the feedback that they need to succeed in that task.

SWGR Whitney Sullivan | Balancing Empathy

Balancing Empathy: Delegating is a skill that takes empathy to learn how to use. If you’re going to delegate well, you have to set boundaries.


Let’s talk a little bit more about feedback and giving feedback. That’s so important. Why is it so hard to give feedback?

I don’t want to speak for everyone. I can speak to my experience. I can speak to clients that I’ve worked with and pull from their experiences. Sometimes, when we give feedback, especially the higher stakes of the feedback, the more we want to try to manage or prevent emotional reactions than the other person. Especially if we need to give critical feedback, we get pretty over-focused on, “I don’t want them to be upset and mad at me. I don’t want them to dislike me. I don’t want them to not approve of me.” We’re using all of this anxiety in the wrong space.

One thing I like to work on with clients is, “What’s your responsibility at this moment? Is it your responsibility to manage their emotions, which are trending towards enmeshment? Is it your responsibility to be as clear and as kind as possible, give them the tools that they need to succeed, and create a safe space for them to have whatever emotional reaction that they might have?”

I circle back a couple of days later and say, “What have you been thinking about this feedback? What can I do to support you?” Giving critical feedback is hard, especially if you’re a sensitive person. Women, especially in the workplace, I don’t know if you’ve experienced this, but I know I experienced a fear of being needy, too bossy, too demanding, or having too high of standards. Those were all fears. I didn’t want people to dislike me if I’m being honest.

That is society. Girls are taught to be liked. That’s the most important.

We have that internal message that says, “If they don’t like me, it’s a failure.” That’s a subtle undertone. I don’t know that that’s always conscious.

It’s an unconscious thing that you receive as a child in so many little bitty ways. It is sometimes directly and sometimes indirectly.

That makes giving feedback hard. It’s vulnerable. This is Brené Brown’s version of vulnerability. It’s emotional exposure, risk, and uncertainty. You’re putting yourself out there to be criticized and disliked. You’re exposing the things that you want, need, and expect in order to succeed. When we over-focus on what the reaction might be, that takes away from being clear about the feedback that we need to give. I also want to validate, too, that feedback is hard. That’s okay to feel a little nervous. I was reading Michelle Obama’s new book. She talked about being comfortably afraid. Be comfortably afraid when you give feedback. That’s normal.

Just be comfortably afraid when you give feedback. Share on X

The other thing is if you don’t tell someone when they are not doing well, they might be kicked upstairs. They might be promoted because you want them out of your department, but promoted upstairs. They’ll make the same mistakes if nobody ever tells them.

It’s a duty. That’s something that I coach leaders on. It’s like, “What’s your duty here?” That’s a personal reflection I had to learn early on in my leadership days. I was like, “It’s my duty to give this feedback, make this decision about their status on the team, or choose not to promote them. That’s my duty and my role.” Part of leadership is sometimes people being upset with that.

You have to be self-aware as a leader to know if you are not promoting somebody, make sure that you have a good reason. People talk to me about executive presence. They always say, “You don’t have executive presence.” Often it’s an excuse not to promote you because you don’t look like the person who’s doing the promoting, whether it be gender, skin color, nationality, or any of the many things. You’re not someone they think of as a leader because you don’t look like them.

That’s not helpful feedback. They’re like, “You have an executive presence.” What does that mean? What do you want? What is your expectation?

One of the things that I found the most helpful at that point is if you are on the receiving end of that, say, “Can you give me some specifics?” There is a good phrase I heard from Dee C. Marshall and Mita Mallick. They have a brilliant podcast called Brown Table Talk, which I listen to and learn a lot from. I learn a lot about how to be a good ally. They said, “What does executive presence look like to you in this company or in this organization? Pin them down.” Gravitas is an executive presence. It more or less means the same thing. There are some specific things that you can do to not sabotage yourself.

I don’t know if this is sassy or not, but asking the question, “What does executive presence look like?” and they say something like assertiveness, what I would want to know in that situation is am I going to be punished for being assertive, too? Women tend to have that double standard of, “We want you to speak up, but not too harshly. Speak up, but don’t be bossy.” It’s such a tough dynamic to navigate, especially when we’re talking about something like executive presence. If you’re looking for a woman to do something, will you reward me for showing up in that way, or will I then be held to a double standard on the other side?

It is a tightrope that we walk as women, especially as powerful women. Let’s talk a bit more about how to set good boundaries and how to get help setting boundaries since it’s something that little girls are often not taught. It took me a long time to learn about boundaries. That was something I learned embarrassingly late.

I was the one who always wanted to be liked. I wanted to be nice. I wanted everybody to love me. I didn’t realize until embarrassingly late that it was not helping me professionally nor was it helping the people I was leading. How can you think about boundaries? Let’s say you’re leading a team. Let’s give ourselves some parameters here. If you’re leading a team, what are important boundaries?

I have a few things circling in my brain as we talk about this. In a general sense, before we dive into some specifics, it’s important to define what boundaries are. I’ve read different authors. I love to read, so I’m always referencing books that I’ve read.

Boundaries are what you want, need, and expect in order to thrive in your role as a leader. That’s some language I pulled from Nedra Tawwab. She wrote the book Set Boundaries, Find Peace. You need to know what you want, need, and expect in order to thrive at work. That’s something that, personally, you need to know.

SWGR Whitney Sullivan | Balancing Empathy

Balancing Empathy: Boundaries are what you want, need, and expect in order to thrive in your role as a leader.


Another powerful definition is from Melissa Urban in her book, The Book of Boundaries. She talks about boundaries being the limits that you need to set in order to feel safe and supported. She is brilliant in pointing out that boundaries are what I will do. We can’t control other people, but we can set expectations and then make adjustments on what we will do in order to remain safe and supported in our workspace. To throw out boundary definitions and authors, I would recommend the following. They’re both females. Both have some great work examples of how important that is to set boundaries at work.

This is based on my own experience. I’m a relational leader. I’m a relational person. One of the big boundaries I had to learn to set was to make sure that. I didn’t blur the boundaries between work and friendship. As a relational person, I built relationships with my employees. We had strong connections. As a leader, you have to know when the role comes before the relationship. If your connection starts to blur the boundary between being a leader and being an employee, that’s not a very good boundary to have.

Another boundary that I think about is what you need for your well-being. What do you want, need, and expect in order to thrive in your well-being at work? This is all introspective stuff. No one can tell you exactly what that’s going to be. It’s something that throughout your leadership journey, you have to have that self-awareness and emotional intelligence of the things that you need in order to show up and operate at your highest self each and every day.

Here is where working with a coach is useful, but also to have a team of allies that you can call on to talk through something.

I call it a support network.

It is so that you can chat about something like, “Where do I find the boundaries for you? How do I deal with this person?” As you are talking about it, you may find the answer coming out of your mouth without your brain being consciously engaged because it’s coming straight from your subconscious.

You got to have that person asking those good questions and rooting for you in that way. Something that I coach clients on is that we have to have some go-to phrases when it comes to setting boundaries. They might feel like writing with your non-dominant hand until you start to integrate them in an authentic way.

There are some phrases that I like to throw out to clients. They are things like I’m talking to an employee that maybe I need to set a new boundary with, a super simple phrase is to say, “Moving forward, what’s okay with me is blank, and what’s not okay with me is blank.” It could also be, “Moving forward, what works for me is XYZ, and what doesn’t work for me is XYZ.” It’s using that contrasting and future-oriented language.

Sometimes, when you have some phrases and words in your back pocket, when it comes time to set a boundary, then you have those words. The boundary has to be followed up with action, and it has to be an action that you can control. Boundaries aren’t controlling other people. They’re limits that you are owning.

Boundaries aren't controlling other people. They're limits that you are owning. Share on X

What happens when you are too empathetic or too friendly?

Sometimes, you can start to blur the boundaries between work and friendship. When we overuse empathy in a way where we start taking on the emotions of other people as our own, that’s a recipe for burnout. That’s when we’ll get burned out. When you’re not protecting your limits, that’s when you’re going to start burning out. It’s hard to show up as your best self when you’re burnt out.

As a leader, you need to be able to lead. If they’ve seen you after your third tequila and dancing on the table, they may not have respect for you, or they may feel the fear at which point it’s safe to say, “I’d rather not do that.”

That’s such a great example.

I remember a case where my boss was standing on the table with a napkin over her head. I never thought of her the same way after that. How can we manage our own self-awareness or recognize the limits of our self-awareness?

I’m biased on this one because I’m a leadership coach. One of the best things you can do is invest in yourself. Invest in tools that are going to help you grow that self-awareness. It could be reading. It could be journaling. The next level up is attending professional development opportunities. The single best thing, in my opinion, and I’m biased as a leadership coach, is working with a coach, working with a mentor, or working with someone who is going to ask you awesome questions, give you that feedback in real-time, and challenge your thinking and your mindset on things.

Especially coaches and mentors, they have tools that they’ve been trained on or that they are committed to using that will help you build that self-awareness. I’ve talked about the Enneagram assessment. It’s a self-awareness assessment. We need language in order to process things. When it comes to self-awareness, the constant pursuit of more language to help you understand your thinking, feeling, and behavioral patterns will help grow your self-awareness. I can’t say enough that working with a coach or a mentor is powerful as you build your leadership practice.

SWGR Whitney Sullivan | Balancing Empathy

Balancing Empathy: That constant pursuit of more and more language to help you understand your thinking, feeling, and behavioral patterns will help grow your self-awareness.


What I keep thinking about is surrounding yourself with people who are strong in the places where you are weak. You may not even be weaker, but you’re not terribly good at that part. An obvious, practical example is I have empowered my team. I’ve asked my team to challenge me and to make me think about decisions. The way my brain works, I usually find that version 3 or 4 is one that we’re going to go with.

I can make a snap decision, but it’s often not the best one. I’m better off if I sleep on it and think about it. I always make sure that my team says, “Are you sure? Do you want to do that? If so, what specifically do you want to do?” Otherwise, I will go off in five different directions. I am easily distracted as a leader. I’ve learned to surround myself with people who are better than I am.

That support network is so important. That’s a key tenet of the program that I run for leaders. It is the connection piece. I’m asking them, “Who is in your support network?” I’m making sure it’s diverse. You want people who are going to cheerlead you, but who are those people that you trust to critique you, too?

They can challenge you.

Some of my favorite connections that I still value so much were those connections that I could go to and completely trust to say, “This is what I’m thinking. What do you think?” They’re like, “That’s crap. You’re completely off base here.” Those are the most valuable connections. We have that trust, too. You have to include critics in your support network as well, ones that you trust.

It brings me back to blind spots. One of my favorite thinkers is Tina Greenbaum of Mastery Under Pressure. She said, “Don’t you want to know your own blind spots? Everybody else can see them.” That’s a quotable quote that I put up on social media from time to time because I need to be reminded.

I would also add to that. If you are a leader that tends to trend towards overusing empathy, the more important it is to have a connection that you trust that you know is going to be a little bit more analytical maybe. One of my favorite colleagues was in higher education. She had a very analytical approach. She was less emotional or relational in her approach. I could trust her to be like, “You’re being too nice.”

If any of this speaks to you, dear reader, where could we start? What is one thing we could do if we’ve been reading this saying, “They’re talking about me?” What’s one thing you can do to start?

To stop overusing empathy?

Yeah, and to start to be a better leader.

If I could go back to my younger self as someone who is struggling to overuse empathy, one thing I would say is to start practicing when the stakes are low. How we view success and failure sometimes is not always accurate. We think success is this one big moment and failure is one big moment, but they’re collections of a lot of small moments. I have a hunch that there are a lot of small moments that you’re overusing empathy. It is where you’re taking empathy too far that you could practice on.

I encourage clients that even if something as simple as their Starbucks drink is made wrong, I want them to go ask to get it made right. It’s those small moments. If the food is bad at the restaurant, are you going to send it back and ask for something different? The clients usually guff at that like, “What?” I’m like, “Really.” When we practice in these small moments and we start to get a sense of what that feels like, what words are authentic for us to use, or what that power feels right to get the Starbucks strength right that you paid $5 for, that eventually builds up and translates into bigger moments. If you can set expectations and be empathetic in your stance in small moments, you can do it in big moments, too.

If you can set expectations and be empathetic in your stance in small moments, you can do it in big moments too. Share on X

Thank you. This has been so useful and so helpful in bringing up some of the painful memories of the mistakes I’ve made.

We’re all human.

There are things you can do to be a better leader to use empathy strategically and set boundaries. Thank you so much for being a guest on the show. If you enjoyed this, please rate us on Apple Podcasts. That’s the one that matters. Give us a good review and a five-star rating. Tell your friends. Subscribe to the YouTube channel. There are lots more about leadership there. If you’ve got any questions, you could contact either me or Whitney Sullivan. I will see you at the next one.


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About Whitney Hinshaw Sullivan

SWGR Whitney Sullivan | Balancing EmpathyWhitney Hinshaw Sullivan is a leadership coach and keynote speaker. With a background in leading fitness, wellness and student leadership programs in higher education, she learned the hard way that transitioning from individual contributor to leader requires a lot more than a change of title.

Whitney offers the coaching she wishes she received so that leaders can show up with clarity, confidence, and resilience.

She currently lives in Bozeman, Montana with her husband Tim, where she is also an avid reader, outdoor adventurer and cycling instructor.