"We Knew in 18 Hours We Had Made a Terrible Decision" w/ Stephanie Henderson

Stephanie Henderson — CEO-turned-executive coach, keynote speaker, culture strategist, and founder of Impact Driven Partners — joins Dr. Matt Paden on the Bad Days Leadership podcast. Stephanie shares the software rollout that blew up within 18 hours because she and the IT director forgot to include the people it would actually affect, how waiting to give feedback until an annual review turned into an hour of tears and a permanent lesson, and why she stopped calling her company a "family" and started calling them a team — because you can't fire your brother. She breaks down why wanting to be liked is a trap, how reframing accountability as an act of love changed everything for her, and why the real red flag isn't how a leader reacts to criticism — it's that nobody feels safe enough to offer any.

Transcript

SPEAKER_01 0:02

Every leader has bad days. Most pretend they don't. This is a show where leaders stop pretending and start learning. Welcome to the Bad Days Leadership Podcast, where leaders pull back the curtain on decisions they cringe about, runes they misread, and the failures that shaped everything out. Real leaders, real mistakes, real lessons. Because you can't become a great leader without a few bad days. Hey everyone, welcome back to the Bad Days Leadership Podcast. I'm so glad you're here. If you've been following along, you know this show is all about something we don't talk about enough in leadership: the bad days. The decisions we regret, the moments we cringe about, and the lessons that shape us into the leaders that we are today. Today's guest has had an incredible career full of influence, impact, and I suspect even a few hard-won lessons along the way. I am thrilled to welcome Stephanie Henderson to our show today. Stephanie is currently a keynote speaker, executive coach, culture strategist, and operational scaling partner. That's a lot, Stephanie. We're gonna can't wait to hear about all that, who helps leaders build organizations that are both high-performing and deeply human. Stephanie has over two decades of executive leadership experience. She was the CEO of a $40 million organization, has served in multiple executive roles. That breadth of leadership helped shape her conviction that sustainable results aren't driven by strategy alone, but by clarity of identity, the strength of culture, and discipline execution. Stephanie is the founder of Impact Driven Partners, where she partners with founders, CEOs, and executive teams through uh keyno speaking, executive coaching, and hands-on operational leadership. Stephanie is from the great state of Texas, and when she's not helping leaders transform their organizations, she is a wife and a mom to two kids. Stephanie, welcome to the Bad Days Leadership Podcast. We are so glad that you are here.

SPEAKER_00 2:12

Yeah, thank you for having me. I'm excited to be here. I always love talking about all the um lovely mistakes I made in leadership along the way. They're great learning experiences.

SPEAKER_01 2:22

Yeah, we we um sometimes we don't call them uh wins and losses. They're wins and lessons. We all have plenty of lessons. We all have plenty of lessons to learn from. So let's just jump in if you're ready. I'd love to start hearing some stories about your uh from your experience and your perspective. Let's start with this. Uh, every leader has at least one moment that they look back on and think, what was I doing? Or maybe it's a moment they observed where they thought, what was that person doing? You know, maybe that was a boss or a leader in another organization, whatever it may be. I'd love to know what's a what's a leadership moment or decision that you still cringe about?

SPEAKER_00 3:01

Yeah, I've got some great stories for this. Um, growing up as a leader, you always have a few. But one that comes to mind the most is um in the company that I was with before, we were doing a soft, a new software integration. And we were a younger company at the time, but we had grown enough that we had to get with some better technology. And um, so our technology affected everybody in our company, um, our guys in the field, our girls on the phone. And um our IT per our IT guy and and myself at the time um made this decision to go with this software. And um we started to implement this software, and we just kind of forgot to figure out how was it gonna affect our people in the field, our people on the phone, our all of these things. It made sense to us in our head from a top level, right? But it it didn't make a lot of sense at all um when we started implementing it, and it was a disaster, it was an absolute disaster. Um, we ended up um w completely wiping the slate clean. We had to call it a loss on that um software, and I over the next two years became um the most educated on how to do our research, how to test in the field, how to communicate and ask and get curious with our people that all of these decisions affected. And um I in in that through that um it was very hard and it was uh one of those things that you did not want to have to swallow and say, Yeah, I messed up there. But I learned so much about being a change maker. And for the rest of my career, that was one of the things that everybody, you know, if they were gonna say Stephanie's good at this, is it is implementing change process, all of those things, because I got to learn it the hard way.

SPEAKER_01 5:00

Yeah. Well, I love that. That's a great story. So tell me, how long did it take before you and the IT director realized this was heading in the wrong direction?

SPEAKER_00 5:09

Oh my, about a day.

SPEAKER_01 5:11

About a day.

SPEAKER_00 5:11

It took about a day. Yeah. I mean, we did all this prep work too between the two of us, and we were so ready and so convinced that this was gonna be the software that was gonna take us to the next level. And um, yeah, I mean, 18 hours in, we were both like, we have made a bad decision here. Uh yeah.

SPEAKER_01 5:31

Well, it's it's it's good that you can look back on it now and and you became you you kind of just referenced this, you became somebody schooled and uh certain and sure about what it takes to change, to lead change. And we talk a lot about leading change in our business, and you know, it changes a story and it has a cast of characters, and it sounds like maybe the lesson there could have been something related to not including the full cast of characters in this change uh initiative, right? So, other than maybe what you shared, are there any other lessons that came out of that moment that you were able to learn from and utilize differently specifically uh as you think about leading change or just leadership in general uh in future opportunities to lead change?

SPEAKER_00 6:14

Yeah. So I think one of the main things I learned through that and and over time as we grew is to always um get a get information from each population of your team. So each department that was gonna be affected by the change. And I actually, as we grew and were bigger, you know, ended up with when I left we had 250 employees. Um, I had a focus group. So if we were gonna do something that was gonna change and affect you know a large portion of the people in our organization, we would call them that focus group first. Here's our problem, here's the possible solutions. Now, how does this how is this gonna affect you? You know, you're in the field or you're you're the one making the sales calls or you're the one doing these things. How will it affect you and your teams? And that was like one A. Before we fully dive in, you know, we did our research first and things like that, and we're able to propose some things to them to get their ideas. But I think that that was one of the most important things that I learned about creating change, especially if your organization has a significant number of team members, um, where you know, you get to a certain level in leadership where it's very hard to feel what it feels like being a frontline person, right? And so making sure you're staying engaged with those people as you're making those decisions that will impact and affect them the most.

SPEAKER_01 7:37

That's really good. That's such a good word. You know, uh leadership is all about other people. And and sometimes it's really hard because we're so caught up in the idea or the the solution to a problem or the project or the product or whatever it may be. And sometimes it's it's the simple things like making sure the people around us are ready to go. It's not the widgets that are usually the problems, it's the communication in the in the people, right? So let me let me just kind of uh set up a next question here. So leadership teaches us to spot patterns, right? And especially the unhealthy ones. Uh sometimes we've learned a lot about what those unhealthy patterns were for us earlier in our careers. And sometimes that's because we've we've learned from our own experiences, kind of like the story you just shared. And sometimes we've seen it in others. Uh so what's a red flag in leadership that maybe early on you didn't catch, but now you can uh you can spot it instantly?

SPEAKER_00 8:36

I would say the ability to control uh your emotions, especially in criticism. Um I I see that being calm, calm in the chaos and things of that nature, and being able to truly humble yourself, um, to take on uh the thoughts and the and the criticism or the correction or accountability from others. Um, you know, that to me, at first I didn't really recognize the the red flag, but it came really clear to me um pretty early on that you know, that was one of the most important things is you want people to feel comfortable and saying, hey, you might have missed the boat on that. And um, you know, and and I guess the red flag would be that people were afraid to do that, maybe more than how the reaction was. Um so seeing that, like, why are my people not giving me real, real information, the real truth about how I'm doing? And you know, if you ask your team, like, hey, is there anything I can work on, and they all say no, then there's a problem there, right? Because there's gotta be something. They're just afraid to talk to you. So I think that would be one of my red flags is just um people not feeling comfortable um coming to you for whatever reason and um being able to control those emotions and the reaction to the criticism.

SPEAKER_01 10:03

That's really good. I think um the feedback, uh, the willingness to receive feedback, right, is so critical for leaders. And when I go into organizations and and see that that's a challenge, that's an immediate red flag for me, too. It's like, wait a minute, there's something going on here. So that's good. It's really good. Let's shift gears just a little bit. And we've all wished that someone maybe would have pulled us aside early on in our career and told us something we didn't learn until much later. Uh, what's something you wish somebody had told you as an early prof uh early career young professional, emerging leader? What's something you wish somebody had had kind of told you about uh earlier on than maybe you were able to learn it on your own?

SPEAKER_00 10:49

Yeah, so one of the things that I struggled with early on that was really tough is accountability um and having the hard conversations. Um so, and really more so that truly caring about a person means you're willing to hold them accountable so they can be their best self. In my early years, it was, you know, I don't want to hurt their feelings. I I am I I want to make sure that they feel empowered and all of those things, and you know, kind of held back a little bit instead of being truly real with people, um, having that full honesty of like, hey, listen, I am doing I I am telling you this because I care about you. And um, I am not willing to let the people I care about not be as excellent as they can be. And just re really was a reframing for me, you know. Um, I I was able to step up and have the conversations, but it was it was scary, right? It was scary and it was um hard, but change reframing that in my mind later on, um, and just realizing like, you know, this is an act of love. I I'm just I'm doing this because it matters to me that you are your best self. And I want to receive the same thing from you. So um that was one of mine, like, man, I wish somebody would have told me that 10 years ago, you know.

SPEAKER_01 12:18

Um how much better would life have been if somebody had shown us what real leadership and real opportunities in the professional world were gonna be like, uh, not just what they appeared to be and uh or what we learned in class or college or wherever somewhere else, or read in a book, right?

SPEAKER_00 12:35

That's right.

SPEAKER_01 12:36

No, I love that word that you just use, reframing. Uh it's a word that uh I think is uh really, really important for leaders to not only be able to reframe themselves, but also to help others reframe and try to make sense of what's going on around them. And one of those mo one of the moments that creates that need for reframing is often when things, well, not just bad, go bad like we talk about on this show, but sometimes it's we learn our best lessons when there's been moments of just failure. And uh I you've had such a successful career. I'm sure there's never been any moments of failure. But if there are anything, are any lessons that you've learned from those moments that were uh edging towards failure or challenge? Uh I think it's really important that maybe our listeners hear from you and and others as we uh have other conversations. Uh talk to talk to young professionals, especially or new leaders, people who have just moved into a leadership role. What would you want them to know about failure?

SPEAKER_00 13:43

I think failure is important to identify um and to accept. Um I think that as as we grow in a leader in leadership roles that you know failure is just gonna happen, right? We're human beings, and to take it as, you know what, I'm glad that happened because now I know, because that was a blind spot that I didn't realize I had. And now because I have gone through this failure and because I did not hit the mark this time, now I know, and from now on, I can be better for that. I can take care of people better, I can serve people better. I think that's the best way to really look at failure in leadership and anything that we do. That you know what, sometimes it's a gift, it's a gift, and we're getting to see now, hey, these winders are off. I am no longer gonna continue to make that mistake, and now I can move forward. And also, as leaders, we should teach the people around us about that as well. So being able to say, look, and have the humility to say, look, this is how I failed, and this is what I learned. And so now you don't have to go through that. You get to learn from my failure. And I that's that's the most beautiful part to failure to me. If you can really dig deep and be humble about it and just say, hey, listen, there's there's some lessons you can learn from me. This way you don't have to fail in the same way.

SPEAKER_01 15:15

The idea that the word you used, humility, is so important to all this. And humil humility is such a posture uh that is um, I don't know, sometimes lacking, but uh it's also that's that's that's where lessons are learned is when there's challenges, right? It's if everything's easy, every day's easy. What lessons are we gonna learn? So I appreciate you bringing up that con that word of humility and just how it all ties together. The opportunity to fail. I think um maybe you had moments like this too. Um I remember my first quote-unquote leadership role. Uh, I was way too young and had uh a mentor kind of walk me through some opportunity on a Friday afternoon that he wanted me to take on Monday morning. And I was a little nervous at 24 years old, and he said, it's okay to make mistakes. And I don't know how it would have gone if he hadn't said that. It went, it worked out uh pretty well in that season of life, but but I kept that in the back of my head a lot, and we tried some things, and some of them worked, and some of them didn't, and he kept telling me it's okay, we're gonna make mistakes. And some things are not everything's gonna work, Matt. And uh I've always appreciated that. But uh that humility, uh, the humility he showed in as a supervisor handing me the reins to a to a team of people that was uh it was a lot, but uh he also just freed me up uh to know that failure was was real and was expected because if we weren't doing anything, we weren't gonna mess up, right? We needed to make some things happen, we needed to try some stuff, we needed to do some things. So I appreciate you saying that. Uh not just failures uh make a difference in what we learn, uh what we learn about ourselves and our leaderships, not just from failures that we uh learn about ourselves. Sometimes it's just those mistakes. Uh they just teach us something. Uh the mistakes we make over time, we don't stew on them, we don't think about them in terms of we can't think about them in terms of the negative, we can't let it weigh us down. But uh do you have any stories about when a mistake helped shape your current leadership style? Mistake.

SPEAKER_00 17:35

Um yes, uh okay, so this is kind of an interesting topic on this, um and it is a mindset type thing. But so we, and this is comes a lot from my values, we really operated with the word family. We're a family, and people use this a lot, and I'm gonna challenge that. So, what what I learned, and I do feel like it was a mistake to use the word family. Um, what I learned is family brings a lot of emotion. Family, um, you know, my you you don't look at your brother and say, you know what, my brother just really is not showing our family values anymore, and he is just not holding up to his end-of-the-deal brotherhood. I'm gonna let that brother go, and I'm gonna get me another brother, right? And so that that breeds something interesting in our businesses when we use that word family, so we completely flip that and started talking about team. And in our team, we still love each other, we still care about each other, in our team, we still have each other's back. And when we walk into our business and we put on our great days leadership jersey, this is our team. And we are fighting for and working for and holding accountable our teammates every single day. And we have a great coach that leads us and all of those things, instead of thinking about it like my family and like this, my dad, you know, looking at this boss that I have like that's like my dad, no, right? There's just so many emotional um dynamics to that, and we used that word family for years, and we realized like that was a mistake. Like, we we need to use the word team, and that's what we are in our business. And um, you know, we we did some fun things with that. We even had letter jackets, and now we we we used the term family for so long, we had to like really so everybody got a letter jacket with our carpet sec team symbol and how many years they'd been there, just like you do um on your sports teams. But that was a big thing that um, you know, a lot of people are surprised when I say that, but I truly believe in that um that you can have that same care that you have, you know, for want to use that word family in your team.

SPEAKER_01 19:58

Yeah, I love that. Uh I have found it to be some of the organizations we work with where they they express themselves as a family, uh, which I appreciate, like you said, at one level. But I also suspect some of the challenges they have as organizations uh are because they have a hard time holding people accountable, uh making tough decisions, you know, doing whatever it takes to you know, whatever's necessary because of that that challenge that is. Now, your example of uh, you know, can't just replace your brother. My sisters, I think, tried a few times uh to replace this one. But you know, I think but I think you're right about that. And I think that's really, really wise, and that's something we can all hear. I think the idea of team, I take the word team very seriously. Me too. Um that one of the problems I've always had is um not just when people refer to an organization as a as a family, but a team, but they don't act like a team. Because I I I I think there's a big difference between a working group and a team. And I I think there are absolutely probably in most organizations you look at moments where the leadership team or the marketing team or the sales team or whatever, they don't even work together regularly. They don't even they don't operate like a team. They they're more just thrown together for assignments and projects, and and that's a different animal too.

SPEAKER_00 21:22

So that's right.

SPEAKER_01 21:24

There is something to that. Uh most of us can look back at something we once thought was great leadership, and now we know better. Maybe you've had a moment where uh maybe hindsight being 2020, uh maybe there was something you used to think was really important or really good about leadership, but now you know it's probably not necessarily as important as maybe you once thought. Anything come to your mind when I say something like that, when I ask you that question?

SPEAKER_00 21:56

Um Well, being liked. All the time, I think, is uh something that comes to mind with that. Um, you know, when you're a leader, you're gonna make decisions that people aren't gonna like sometimes. And um, there are going to be people in your company and on your team that um don't agree, maybe don't like you for a season. And um, you know, I learned later on that sometimes that means you're doing the job that you were assigned to do. Um, and that, you know, obviously we have to look at all sides of that. Are are we being, you know, good stewards of what has been given to us to lead? Are we, do we have compassion? And are we doing all the things that we should be doing right? But um sometimes we got to make those hard decisions and we're just not gonna be liked about it, or people are gonna be upset, and that is okay. And um, you know, I think clarity is important in those areas and those spaces. But, you know, early on I did. I wanted to be liked, I wanted to be, you know, everybody's favorite. I, you know, I wanted to make sure everybody was happy with what I was doing, and that's not actually true sometimes. So that was definitely one of those for me.

SPEAKER_01 23:12

Yeah, I think one of the things that made the sitcom The Office so popular and people resonated with it was because Michael Scott, as most people know, um, was a boss who wanted to be loved, right? And had a hard time with a lot of things. But I think one of the reasons people appreciated that is because they'd seen it. You know, they'd seen that uh there's probably polar opposite that they've seen. They've seen the boss that wants everybody to love him or her, and then there's the person who's kind of the tyrant, but somewhere in the middle is where there's some there's probably some reality that where we need to land. But it is um it's such a myth that leaders are gonna be liked. I mean, and the reality is most leaders I talk to would express, maybe they won't express it loudly, but quietly, one-on-one, they often express that uh leadership is more lonely than they anticipated.

SPEAKER_00 24:05

Absolutely.

SPEAKER_01 24:06

So that's uh that's a good word for everybody. Um just got a couple more questions here. Uh we we've all kind of been there. You mentioned feedback earlier. I want to go back to that topic for just a second. You've been in, you've been, you were mentioning it earlier as though you were uh, as a leader, you have to be willing to hear what people have to say. I also think there's great examples of what it means to provide feedback. And or there's probably some examples from your career where you've delivered feedback that maybe it didn't go real well. And maybe you learned some stuff about how uh yourself and how you offered that feedback or how it was put together, how it was packaged, whatever it may be. Tell us a little bit about uh maybe a moment where you've delivered feedback and it didn't go really well, maybe even horribly wrong. I don't know, but uh give uh give us uh a moment there that you can remember giving feedback that didn't get taken, especially.

SPEAKER_00 25:04

Yes, I can remember early on um I was sitting across from a another um person in my organization giving feedback, and it there was a there ended up being a lot of tears. Um it it was because I had waited too long, right? I I had this idea in my mind I'd learned in school and these things and and about, you know, we're gonna we're gonna do a review, we're gonna do an annual review, you know, and we're gonna sit down and we're gonna sit across from each other and I'm gonna tell you all of these things. And um this is somebody that I talk to every day, right? I talk to them every single day. And um, they were right down the hall from me. And I sat down to for that review, and the things that I had been missing talking to them about every single single day were the things that they needed to work on, and there were a lot of them. And um I'm sitting there, you know, and she's she was oblivious to them. Um her self-awareness was a little off, but I as the leader had failed to say, um, you know, frequently and as they happened, like, hey, this is a problem, you know, like something that we need to fix. And um, you know, it it it was rough. I'm uh I'm telling you what, it was a long hour um for me, uh, but it taught me a lot about feedback and how important it is that the timing is right, that we do it um more often than just once a year, every six months, every quarter. Um, but it is part of just our culture, right? To give feedback. And um, I also learned in this that I then something I truly loved is before um, you know, we're gonna have an intentional moment of feedback, to initially ask the the team member, what do you feel like you need to work on? Um, and have them take some time and to intentionally think about, okay, in these areas, and I would give them areas, these are the areas that I'd like you to assess of yourself. What do you think you're doing well? What do you think you need to work on? And um, then they would bring that back to me and then we could meet. And nine times out of ten, 98% of what I was going to tell them, they already knew in themselves that they needed to work on. And it was so much easier, easily accepted, so much more easily accepted because it was their idea, right? Um, and so I I appreciated that. I learned that through that um, you know, very quickly. It didn't take me but one review. Um, and I said, okay, we're gonna do this differently. And how do we do this differently? And that, and so that would be mine for sure.

SPEAKER_01 28:03

That's really good. Stephanie, this has been so good. Thank you for your honesty, your stories, and the way you have uh shared both your wisdom and your humility. And you've allowed us to uh add those into our conversation about leadership. Before we wrap up, uh, I do have one more question for you. But before we wrap up, I'd love for you to tell us something that you have coming up that you are most excited about with your business, with your work, with all that you've got going on.

SPEAKER_00 28:30

Yes. Okay, so I'm excited about this one. Um, so Impact Driven Partners, um, we have what we call the culture curriculum. And the culture curriculum is basically um how as a leader to root yourself, um, figure out what your real identity is, and create an amazing culture in your organization. And then how to weave that culture into your organization to create impact, um, create the results that we want as an organization to create impact in our community. So my exciting news is I'm actually traveling to Africa in June, and I am getting to teach that culture curriculum to um a group of business leaders um in Harar, Africa. So that's a fun and exciting adventure for me. And I would never thought being a girl from Littlefield, Little Bitty, Littlefield, Texas, would be able to teach something that I created in Africa. So that's a big thing for impact-driven partners. And um, one of my favorite things to do is uh work on that culture stuff.

SPEAKER_01 29:39

That is so, so awesome. Uh, that'll be an amazing trip to Africa. Maybe we'll have to have you back on and you can tell us all about it after that.

SPEAKER_00 29:46

That's right. That's right.

SPEAKER_01 29:47

That'd be good. Let me uh let me leave us or have you leave us with an answer to this question. This is a question we often ask, or a version of that we often ask. If you could have uh if you could leave leaders with one uh encouragement about their worst days, what would it be? Leaders that you know they're gonna have them. They they know they're gonna have them, but what's this one encouraging kind of word or thought you'd like to share with those that are going through hard days?

SPEAKER_00 30:18

I think just remember that tomorrow's gonna be better. And that one day you're gonna be able to laugh about this situation. I mean, you know, I think that we take life way too seriously sometimes, and everybody makes mistakes, but tomorrow's gonna be better. And um the sun's gonna rise and we're gonna be able to put a smile on our face no matter what's going on. We've all been there.

SPEAKER_01 30:45

That is so good. That is a good word. Stephanie, thank you again for joining us and everyone listening. Remember, your bad days don't disqualify you, they develop you. If you've enjoyed uh this episode or others of our podcasts, we'd love for you to like and subscribe to the Bad Days Leadership Podcast. We will see you on the next episode.