“Leadership is getting in the trenches with those you serve and leading by example.”

In this episode of Executive Evolution, Craig Anderson chats with Cassie Mecklenburg, Executive Director of Sheltering Wings, about how emotional intelligence and empathy play a big role in leadership.

Cassie shares her story, starting from her leadership roles in college all the way to running a successful non-profit, and how she leads at Sheltering Wings today. She talks about how she balances big-picture thinking with the day-to-day stuff, and why having a team with different strengths makes all the difference.

Things to listen for:

• (00:37) The importance of emotional intelligence
• (01:54) How to navigate tough topics with people-first leadership
• (03:49) Knowing when to compromise or stand firm
• (15:03) The importance of curiosity in leadership
• (17:31) From daily tasks to community-focused leadership
• (20:07) How to be a coach and not just a problem solver
• (24:25) Why leaders should build friendships with their teams

After You Listen:

• Connect with Cassie on LinkedIn
• Connect with Craig on LinkedIn

Key Takeaways:

• Practice empathy by understanding your team’s challenges
• Surround yourself with diverse perspectives to enrich decision-making
• Lead by example by getting in the trenches and showing you're willing to do the hard work alongside them

This has been generated by AI and optimized by a human. 

Craig Anderson [00:00:00]:

In a meeting in front of the entire sales organization, I looked directly at one of the sales reps and said, if I can only sell this product at that kind of discount, I might as well hire a bunch of flying monkeys. Welcome to Executive Evolution. I have over 25 years of leadership experience in corporate America. I learned a lot of lessons the hard way, and I created this podcast so that you won't have to. On this episode of Executive Evolution, we spend time with Cassie Mecklenburg, the executive director of Sheltering Wings. And one of the things we talk about is the importance of emotional intelligence and empathy. And the story I have to tell you before we get into that interview is a time when I did not have that level of empathy. My team was going through a difficult time.

Craig Anderson [00:00:45]:

The industry was going through an intense period of price competition, and I didn't have any good answers. And I was getting peppered throughout the sales meeting about pricing, and I knew I couldn't sell that pricing to my senior leadership. So I looked him right in the eye and said, I may as well just hire a bunch of flying monkeys if I have to discount like this. Not my greatest moment as a leader. We really do need to appreciate and listen to our team and understand what it is they're going through and really have an honoring and faith that the input that they're giving us and just casually brushing it off as I did was not worthy of me or worthy of them. So I would encourage all leaders to really begin to practice emotional intelligence and empathy in their leadership style. And that's a core of what we discussed with Cassie today. So let's jump in right now and hear the story of her Executive Evolution.

Craig Anderson [00:01:37]:

Cassie, welcome to Executive Evolution. I'm so glad to have you join us today.

Cassie Mecklenburg [00:01:41]:

Oh, I'm so glad to be here.

Craig Anderson [00:01:43]:

Yeah. You do such great work with your organization. We'll talk about that later. But I'm really excited to have your perspective as an executive director of a not for profit on Executive Evolution today. So are you ready to dive in and get started with our lightning round?

Cassie Mecklenburg [00:01:56]:

Yeah, let's do it.

Craig Anderson [00:01:58]:

All right, question number one. What is the best leadership book you have ever read?

Cassie Mecklenburg [00:02:04]:

I'm going a non traditional route, and I'm going to say charitable discourse by Dan Boone.

Craig Anderson [00:02:10]:

Wow. What brings that one up front for you?

Cassie Mecklenburg [00:02:14]:

So my faith is really important to me, and so it comes from a faith perspective, but the concept behind the book is that we should be able to have conversations about difficult topics. And so it really is about equipping you to have those conversations without it being polarizing and with it being very people first minded. And I just think that that is so incredibly important in our leadership that we think about it from that perspective and really think about not how can we have a disagreement, but how can we have a charitable discourse?

Craig Anderson [00:02:47]:

I love that. It's so true. So many leaders and evolving leaders that I talk to, they struggle with those difficult conversations because they want to make sure they're liked or they're worried it's going to, or for some reason that feels like conflict to them and they don't want to have that conflict, and they don't have a good way to enter into those conversations, and then they end up putting them off, which only makes those conversations even harder. So what a great book.

Cassie Mecklenburg [00:03:12]:

Yeah. And my innate tendency and personality is to think everyone can come to the table, and if we talk about it long enough, then we'll all be in agreement. But that's not true. There are some things that we believe that we've experienced that we just hold true to that looks different from what a conclusion that someone else is going to come to. And so this book has really helped open my eyes to say, okay, how can we all come to the table? But it's okay if you walk away with a different perspective and you never actually fully agree.

Craig Anderson [00:03:48]:

Yeah, no, I love that. And now I'm just curious, when you're around maybe the table with your leadership team or with your board, but probably your leadership team, and we can only get to 75% agreement, how do you go forth from there with the leadership team? So you're still kind of united front.

Cassie Mecklenburg [00:04:05]:

That's hard, right. So you really have to look at it on a case by case basis, because sometimes there are times where I need to compromise and I need to identify, this isn't something, this isn't a hill I'm going to die on. This is a place that I can get comfortable enough with for us to move forward. And so I'll concede and I'll say, okay, let's go your way. Let's try it. Let's move forward. There's other times, as the leader of an organization, where you have to have the discernment to know, no, I'm going to put my foot down. Like, I understand that you don't like the answer or that it's not your first choice, but as the leader of this organization, I've got to put my stamp on it and say it is what it is.

Cassie Mecklenburg [00:04:50]:

And to know the difference takes a lot of wisdom and discernment.

Craig Anderson [00:04:54]:

Oh, it absolutely does. Yeah. And it just kind of builds with experience that you're able to kind of see into those and make that call and probably also your own confidence as a leader to be able to say, no, this is where I'm going to put to say no, this is where we're going to go.

Cassie Mecklenburg [00:05:09]:

Well, that's why you're the leader. Right? I mean, there are times where you have to make those hard decisions. And at the end of the day, whether it's my decision or whether it's my team's decision, it's quote unquote my decision because I'm going to take the fall if it's not the best, if it doesn't turn out exactly, no matter whose idea it is. But I'm going to give credit where credit's due when it's a victory. And so we've got to be mindful of that, that as the leaders. If I put my stamp on it, it's my responsibility. If it doesn't go as well as it could. But then at the same time, like I said, giving credit where credit's due when it does go really well and someone else has come up with it.

Craig Anderson [00:05:48]:

Love it. Great. Okay, next question. Who is your leadership crush?

Cassie Mecklenburg [00:05:53]:

So I laugh at this question. My leadership crush is Allison Malingdon with IMS.

Craig Anderson [00:06:00]:

Okay.

Cassie Mecklenburg [00:06:00]:

And I just have so much respect for her and I won't go and tell her story, but she one time was at a speaking engagement and shared a very vulnerable story about a mistake that she made that was pretty embarrassing for her. And to get up in front of a room of about 250 individuals and to admit that I thought took a whole lot of courage, grit and vulnerability. And it was in that moment that I thought, I like this woman. Like, she is a good leader. And we oftentimes don't elevate leaders because of a shortcoming or a mistake that they've made or something along those lines. It's because of what great things that they've done. And Allison has done unbelievable things for the city of Indianapolis, through the Super bowl, through the IMS, through the Indiana Sports Corp, all of these things that she's done. But she's also not afraid to be real and to be human and to share those mistakes she's made along the way.

Craig Anderson [00:07:00]:

No. And that's such a great point because we believe we have this kind of, we have a lot of beliefs about what good leadership is that are wrong. And one of those is that you always have to be stoic, you always have to be kind of this pillar who isn't affected. But it's hard for your team to kind of identify with you that way. I mean, everybody sometimes feels scared or elated or worried or whatever it is. I think it's our job as leaders to say, hey, I'm feeling that, too. But here's the way forward. I'm going to make mistakes, but this is what we're going to do to try and make up for them.

Craig Anderson [00:07:31]:

And that's how you kind of align people better with you and you get them to follow you through those difficult times. So that's a great story. I don't know her, but I love that story.

Cassie Mecklenburg [00:07:39]:

Yeah. Oh, she is fantastic. She's great.

Craig Anderson [00:07:41]:

Great. All right, last question. In the lightning round, in ten words or less, how would you define leadership?

Cassie Mecklenburg [00:07:49]:

I think leadership is getting in the trenches with those you serve and leading by example.

Craig Anderson [00:07:56]:

I love it. Okay, so say more about that. How does that show up for you?

Cassie Mecklenburg [00:08:01]:

Yeah. I never want to ask my team to do something that I'm not willing to do. I work for Sheltering Wings. We're a domestic violence shelter and service support center. And so we have a community living environment where our families come and live. And so, as you can imagine with that, while we have this wonderful, beautiful facility, there are challenges with community living, and there are household chores here, just like there is everywhere else. And there's nothing that I should be asking my staff to do that I'm not willing to do. And so, while it's not necessarily my job, there's times where I'll pitch in to wash dishes or I'll do different things.

Cassie Mecklenburg [00:08:38]:

When we have a third shift that's open because we've got someone on extended leave and we just. We're having a hard time filling that spot, I'll occasionally step in to do that, and it's not because of any greatness of mine or anything along those. It's just because that's what we do. We come alongside one another, and we should be leading in the way that shows that every position, every role is valuable and important because it's what makes the team work and our organization thrive.

Craig Anderson [00:09:07]:

Yeah. And I think that's so important because every job is what's driving towards accomplishing the mission. Right. And when people can't see how their yden, you know, maybe I'm just sweeping this hallway and how am I actually helping solve the problem we're trying to solve? But they're all such crucial positions right about. So helping people see that's important. As a leader.

Cassie Mecklenburg [00:09:25]:

Yeah. And I'm not the expert at all of those things. And so sometimes when I work alongside a colleague, you know, I'll have to say, look, I am here to help you and to do what you tell me to do because this is not my expertise. And that's a bridge builder for us as well. When we work alongside each other. I don't want to just sit in my office all day long and I do enough of that.

Craig Anderson [00:09:47]:

Right.

Cassie Mecklenburg [00:09:48]:

It's super easy and I'm prone to it. I'm prone to sit behind my desk or to be out on donor calls or meetings with members in the community, but I want to have those touch points with my team as well. And so I have to be intentional about that. It's not something for me that just comes supernatural.

Craig Anderson [00:10:05]:

Right.

Cassie Mecklenburg [00:10:06]:

So I have to do that.

Craig Anderson [00:10:07]:

Cool. All right. I'm. Well, let's kind of go back. We always like to talk about, Cassie, your first real leadership role. So if you think back to kind of your career or even before you started your career, you know, what was your first real leadership role?

Cassie Mecklenburg [00:10:22]:

Yeah, I'm going to go back to college. When I was at Olivet Nazarene University, I was class president for my sophomore, junior and senior year and loved that opportunity to be a leader and to learn and kind of cut my teeth on what it means to be a leader. It was something that I had to really tremendous privilege where faculty and staff invested in me and poured into my life at such a formative time and really helped me through the ups and downs as I was figuring out the early stages of adulting and what all that means and what was next for me. I would say that's really where I cut my teeth in a quasi formal leadership world.

Craig Anderson [00:11:03]:

Sure. That's a big piece, right? Kind of bridging that gap with faculty and students and kind of being in that middle, you know, looking back, what were some of the challenges for you in that early leadership role?

Cassie Mecklenburg [00:11:15]:

When you're in college, you have a tendency to think you know everything. It's like when you are a 6th grader in an elementary school and you're the top dog and you just, you know, you think you're so great or you're a senior in high school and you're the top dog. When you're in college, you're at kind of the pinnacle of what you've known so far in your educational world and environment. And so you're in college and you're doing the things, you're living independently and so in my leadership. When I look back on it, I think that that concept was kind of reflective in my leadership. And it's not that I walked around with this really cocky or conceited notion that, you know, how big I was on campus or something along those lines, but it did give me this sense of ownership and responsibility that I sometimes didn't always know exactly how to navigate. And so I would maybe entitled is the right word. At times.

Cassie Mecklenburg [00:12:19]:

I don't feel like I was entitled all of the time, but just those moments of, oh, yeah, I know who to talk to and who to go to, and I can get that done and there's a healthy confidence that can come with it. But when it's not tempered and monitored and you're not cognizant of it, it can turn into entitlement. I can think of times where I maybe didn't navigate that tension as well as I should have.

Craig Anderson [00:12:43]:

Yeah. And especially when you talked a minute ago about kind of that servant leadership aspect, that's really something that's a struggle when you're younger in those leadership roles saying, well, no, I'm kind of a big deal right now. I don't do that thing. And so it does kind of tip into maybe almost a little bit of arrogance or entitlement. Did you ever come to kind of in a realization to look around saying, wow, am I coming across like this?

Cassie Mecklenburg [00:13:07]:

So there's one experience in particular that stands out to me. The short story of it is that our admissions department was bringing in juniors and seniors of high school, and they were going to feature them and honor them at my senior year graduation, baccalaureate service. I learned about this kind of through a roundabout way. And I was senior class president, and myself and a couple of others just thought, well, that doesn't make any sense. This is our baccalaureate service. This is supposed to be about us. Why is the admissions team trying to take this over and highlight juniors and seniors that haven't even come here yet? And so we jumped to these conclusions of what that was going to look like and it wasn't going to be about us anymore, and they were going to turn it all into this thing about underclassmen or juniors and seniors in high school. And so I went to, I think it was the dean, if I remember correctly, who I knew.

Cassie Mecklenburg [00:14:08]:

And so I went to them and said, hey, the admissions team is doing this. I don't like it. How are we going to address this? What's it going to look like? And the short is it got back to the admissions team and they said, why didn't you come to us in the first place? Like, we could have had a conversation about this and we could have clarified that it's literally a 32nd welcome that we're just acknowledging that they're here and it's not some big focus. But I was so caught up in what I thought it was going to be and jumping to these conclusions, and so I ate a lot of humble pie that day. And even still, there's a person in admissions. Her name is Lisa, and I've lost touch with her, but if I could go back to her, that's truly one of my regrets because I know that I was like, hey, I'm not going to let this happen on my watch. And so why went guns ablazing? And I didn't just stop and ask the questions. I think about right now, we hear a lot about being curious and just asking good questions, and I didn't do that.

Craig Anderson [00:15:11]:

Yeah, it's so funny because that curious, and we do talk a lot about that now, and it solves so many problems. We make so many assumptions about what's going on, and we tend not to do those with positive intent. Right. And so I see that a lot with kind of leaders who say, well, you know, I know why they're doing this because, da da da da da da. What conversations have you had to maybe dig into that? Because that's a big leap and we don't know. And it kind of gets back to where you're talking to. When we're a leader, we feel like we should be so resolute and everybody we should know, and to sit there in front of everybody say, I don't know why this happened. Tell me what was going on with you.

Craig Anderson [00:15:47]:

Seems like such a weakness, but it's really a strength for a leader to come out that way.

Cassie Mecklenburg [00:15:52]:

Yeah, absolutely. I wish that I would have done that beforehand, but I didn't. And it's one of those moments where I look back and I just think, man, that's not a reflection of who I was or my character. Like, luckily, it's not. It's a moment in time, but it just has stuck with me. So, Lisa from admissions, if you're listening to this, I'm so sorry.

Craig Anderson [00:16:12]:

I love it. That's great. Well, hopefully she is. All right, so now let's kind of move forward, right? You've been through a lot of roles. You've been through a lot in your career. Now you're the executive director at Sheltering Wings. Tell us what leadership looks like for you. Today, because I'm going to guess, you have employees, you have volunteers, you have the people you serve.

Craig Anderson [00:16:34]:

You're leading in a lot of different ways. What does leadership look like for you today?

Cassie Mecklenburg [00:16:38]:

Yeah, so I'm the executive director of Sheltering Wings. We're a domestic violence shelter and service provider, and we've got about 40 staff members. Since I started eleven years ago, we've grown from about 25 to 40, and so we've had quite a bit of growth, and we've built out an executive team and then a leadership team, and then we try to pour into our staff and encourage professional development. And so it's been a challenge in the evolution for me of growing the organization, because when I first started, the needs for leadership looked very different than what they do today. As one of 25, which was still a decent sized staff, but as one of 25, I was a lot more in the trenches and I was doing a lot more of the day to day work that needed to be done at a high level. But I was much more involved and integrated versus today my role has shifted quite a bit, and I've had to be really intentional to get myself out of some of those day to day tasks and keep reminding myself that my role and really what the organization needs from me is more of that strategic, visionary, entrepreneurial, community minded leadership versus leading on that day to day level. And so it's been a fun transition, but it's been a learning curve. As we get into these habits and routines of what's happening and how things work and when it's going smoothly, that's great.

Cassie Mecklenburg [00:18:06]:

But as organizations evolve, you've got to evolve with it.

Craig Anderson [00:18:10]:

And I've seen and talked about this a lot of kind of, as you evolve, move up into those higher level leadership roles, there were probably things when it was small that you love being involved in day to day, and now you can't be, or I guess you could be, but probably to the detriment of everything else you've got to make sure is getting done. How did you kind of get your mindset built around pulling away from the things you really enjoyed? Because I have a higher call for what I'm doing for the organization now. How did you kind of go through that process?

Cassie Mecklenburg [00:18:40]:

First, I think I had to create a level of self awareness of what was I actually doing, because when you're in the midst of it, everything feels important, feels urgent, feels like it needs my hand on it. But what I had to come, I had to step back and say, wait a minute, you've got a really capable, confident, competent staff that can handle this, and I don't have to serve in those roles like I once did because we've grown and because we've kind of evolved with our organization and we've made some really great hires of some really capable people. And so that's really helpful when you have faith and trust in your team to be able to do the work. And so I think that's part of it. If I was looking around our organization and felt like they couldn't do the work, and so that would be a real temptation for me to keep putting my hands back into it. And so spending the time to hire a team that can do their job at a level with excellence is well worth the extra time of the time to invest in that. Whether that's prolonging the hiring process, working through recruiting and networking, it's just really important to have the right people on your team. So that's been really helpful as we've grown to put a more intentional effort into that.

Cassie Mecklenburg [00:20:03]:

I would say the other part for me is just being more comfortable in a coaching role versus an executing role. Recently we've had some staffing challenges that I was helping the team navigate and I could feel myself working with our leadership team and I just wanted to go fix it. I'm a problem solver. I would not say I'm the best listener. When people come to me with a problem, if you just want me to sit here and listen, like, you've got to be abundantly clear that's what you want. Because I just want to go into problem solving mode.

Craig Anderson [00:20:40]:

Right.

Cassie Mecklenburg [00:20:41]:

And so with my team, I recently was just feeling this tension, internal tension of I just want to fix this for the team. But what I really need to do here is coach my team to handle it. And so recognizing that my tendency is to fix, but that the needs of the people and the organization is for me to coach is really an important level of self awareness.

Craig Anderson [00:21:06]:

For me, it's kind of figuring out where are we making our highest level of contribution to the team and to the organization. And it's really kind of leveraging your experience and your knowledge through the growth to say, let me help the team succeed, instead of doing all the work myself or trying to do all the work myself, especially if you're a problem solver.

Cassie Mecklenburg [00:21:24]:

It's that adage, right, of do you give a person a fish or do you teach them how to fish? And sometimes it's much faster in the moment to just give them a fish and solve it. And move on and you're done. But next time something like that happens, which there's going to be a next time, then if you've better helped equip them to handle it themselves. That Runway of time is so much shorter that things can be handled more quickly.

Craig Anderson [00:21:54]:

Oh, yeah. No, it's such a truism. And that's one of the biggest things when I talk to people about delegation, is they don't want to do it because it's too much time to teach somebody how to do something. They don't look at it as an investment. They look at it as time wasted when it's actually to say, hey, if I can teach you how to do this once, that's 25 times. I don't have to do this thing. And you can go forth and probably do it in a way that brings you something you bring to it. That may be even more than what I'm doing with the role, but it's a hard mental leap for people to make.

Cassie Mecklenburg [00:22:26]:

Yeah. And to be fair, it's a lesson I'm still learning. Right. I mean, I still, at times, just want to get my hands on something, and, you know, my natural tendency is to jump to that, but I have to remind myself to take that step back from it.

Craig Anderson [00:22:40]:

Sure. One other thing when we talked about is you started out with an organization, you came in, there's 25, you have 40 now you build a leadership team and an executive team. Can we just talk a bit about, as you built that leadership team, what were the things that were important to you in building that leadership team, and what lessons have you learned from that experience?

Cassie Mecklenburg [00:23:01]:

I'm gonna go with my executive team. So I have a program director and a donor and community engagement or a development director that I work really closely with. And when hiring both of them, I wanted people that I saw that they had different strengths than what I did. I was intentionally looking for people who could do things differently and have a different but yet complementary perspective to what I have. Because it kind of goes back to the previous conversation. If I have all of the ideas and I hire people who have all of the same ideas that I have, then that's really a very limited way for us to lead and run the organization. But when we can come together and have different ideas, people who feel. Who would feel comfortable and safe to express a difference of opinions, I don't want people who are always going to cower back and acquiesce and say, oh, Cassie said this.

Cassie Mecklenburg [00:23:57]:

So this is what we're going to do. I'm comfortable with challenge because I don't always have the best ideas. I don't always know the best way to move forward, forward with things. And so I wanted to hire people who were different enough, yet shared the same vision, that we could really rely on one another as a team.

Craig Anderson [00:24:17]:

Love it. I love it. That is so fantastic. Thank you. So, Cassie, I always like to give my guests an opportunity to do a little time traveling, go back in time to young Cassie in that first leadership role. What's the one piece of advice you would give her that would make her better life? Easier? Hold her calm. What's the one thing you wish you could go back and tell young Cassie?

Cassie Mecklenburg [00:24:42]:

I don't know if this is exactly how I would phrase it, but something to reiterate that empathy is key. I don't know if people explicitly told me this or if it's just something I built in my own mind from pulling nuggets here and there, but I thought that there had to be a pretty distinct relational barrier between a leader and those who report to them that you couldn't or you shouldn't, that you had to be careful with being friends with people who report to you and that you just needed to make sure that you kept that personal and professional boundary clear. And I think that's terrible advice. I think it's something that we have to be really mindful of and sensitive to because it can be very complicated when we're friends. And sometimes that diminishes a person's ability to speak truth either way, either to the leader or from the leader, because they don't want to mess up the friendship and so they're afraid to speak truth there. But if you can bring two people together who can do that and navigate that well and appropriately and sometimes be okay with uncomfortable conversations, I mean, why not get to know your team? Why not empathize with them and share life? I think that it helps you make better decisions and it helps you become a stronger team. I think that leadership is much more about emotional intelligence than just strategic planning. And emotional intelligence and empathy go hand in hand.

Cassie Mecklenburg [00:26:17]:

I've missed out on relationships with people who I think could have been really great friends and colleagues because of that. And I wish I would have learned that a little bit earlier.

Craig Anderson [00:26:27]:

Love it. Okay, great. Well, Cassie, really appreciate you sharing your story today. If people want to learn more about Sheltering Wings or connect with you, what are the best places for them to go to do that?

Cassie Mecklenburg [00:26:39]:

Yeah. So shelteringwings.org is our website, and Sheltering Wings is our handle on all social media channels. So that's a great way to connect with us.

Craig Anderson [00:26:49]:

Great. Well, thank you so much. And we'll get all those links in the show notes. And again, thanks for sharing the story of your Executive Evolution, Cassie.

Cassie Mecklenburg [00:26:57]:

Thank you.

Craig Anderson [00:27:01]:

Thanks to Cassie for such a great interview. She really touched on so many things that I think are important about leadership. And as always, I want to break those down into the three critical leadership areas of confidence, competence and calm. In the area of confidence, Cassie told us how she will defer to her leadership team when they're in disagreement. Not all the time and not every time, but when there's a compelling case, she has enough confidence to know there may be something she doesn't know, and it's the right time to say, not my way, but yours. And that's really hard to do unless we have built up a great level of confidence than the team that we've surrounded ourselves with in the area of competence. Following up on that, she talked about hiring a complementary leadership team. A lot of times, leaders want to surround themselves with people who are just like them, and that's a huge weakness.

Craig Anderson [00:27:53]:

We need to be challenged, and it's a sign of leadership competence when we bring people around us who we know will disagree with us, maybe we share the same vision, but we want people who maybe have a different view of how we're going to get things done. And then finally, I want to talk about how she keeps her calm, and that's by having faith and trust in the team that she surrounded herself with. She had a great opportunity as her organization grew, to build that executive team and leadership team around her. And you really want to build a team that you have faith and trust in that will lead the organization in the way you see the vision and set the direction for the business. So thanks again, Cassie, for sharing the story of your Executive Evolution. Remember, you can go from being an accidental leader to the greatest leader of all time. All it takes is developing your competence, competition, confidence, and calm. See you next time.