Lead with Swagger
Lead with Swagger, hosted by Jennifer Sukalo, is your go-to podcast for bold, purposeful leadership and personal transformation. Whether you're fresh out of school, navigating a midlife pivot, or completely reinventing yourself, this show is your invitation to lead with confidence, clarity, and unapologetic authenticity.
Jennifer—an executive coach, TEDx speaker, and award-winning author with over 30 years of experience—has helped more than 50,000 leaders around the world unlock their potential. Her unique approach blends behavioral science, real-world insight, and practical, doable strategies that empower you to lead your career, your business, and your life with intention.
Each episode delivers compelling conversations, actionable tools, and transformative wisdom to help you break free from fear and self-doubt—and instead lead with clarity, courage, and yes, swagger.
This isn’t just about success. It’s about fulfillment, alignment, and becoming the most powerful version of yourself.
The question is: Are you ready to lead?
Lead with Swagger
#71 | You’re Not Helping—You’re Holding Them Back (The Leadership Lesson You Can’t Afford to Miss)
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You mean well… but what if your “help” is actually holding people back?
In this raw and eye-opening episode of Lead With Swagger, Jennifer Sukalo shares a humbling moment that reveals a powerful leadership truth: good intentions don’t always create good results.
From stepping in too quickly to solving problems for others, this episode exposes how “helping” can quietly create dependence instead of confidence—and what to do instead.
If you’ve ever thought, “It’s just faster if I do it myself”… this one’s for you.
Hit play and learn how to stop overhelping—and start building stronger, more confident leaders.
Let me ask you something. Have you ever tried to quote unquote help and somehow made things worse? Like you stepped in with the best intentions, thinking, I've got this, I'll make it easier, I'll save time, I'll help them succeed. And then later realized you didn't help. You actually made them more dependent on you. Yeah. Same here. So the other day, I got called out by a dog trainer in front of my dog and my husband, who, by the way, immediately sided with her. Not my husband, my dog. Rude, right? We were working with our dog chance and she's observing how I interact with him. And within minutes, she stops me and says, Yeah, so um he's thinking he's in charge. And I'm like, Excuse me? Here I was thinking, I've got this. I know how to be the calm, confident leader. I work with this all the time with my horses. I lead teams, I guide and develop other leaders. I have this covered, right? Wrong. Apparently, I did not have this. Because while I thought I was being calm, supportive, and guiding him, my actions were screaming, chance, you take the lead. I'll follow you. Wow, wake up, call. And in that moment, I had this realization that even with the best intentions, we can reinforce the wrong behaviors. Sound familiar? Stay with me because this isn't about dogs. This is about how we show up as leaders, parents, partners, and friends every single day. Welcome back to Lead with Swagger, the podcast where we get real raw and ridiculously honest about what it takes to lead with confidence, authenticity, and a whole lot of heart. I'm your host, Jennifer Socallo. And before we go any further, can I just say I'm genuinely proud of you for being here? Not in a weird, condescending gold star for showing up kind of way, but truly because you're choosing growth. You're choosing to get better, you're choosing to lead on purpose instead of just winging it and hoping for the best. And that already puts you ahead of so many people out there just reacting their way through leadership. So well done, you. Now, here's a truth I need you to hear. We are all works in progress. Always. It doesn't matter how experienced you are, how many teams you've led, how many wins you've had, there's always another level. And honestly, that's what makes this fun. Because imagine if we had it all figured out, just flawlessly executing every single day. Sounds like the most boring existence imaginable. Growth is the game. And sometimes growth looks a lot like getting humbled by your dog. I've seen this pattern everywhere in my life with my horses and my relationships, and especially in leadership. The more I learn, the more I realize, oh wow, there's more for me to learn. And this moment with chance, it reminded me of something powerful. Having the right intention does not guarantee the right impact. Now let me say it another way: good intentions do not equal good leadership. It actually took me back to when I read Multipliers by Liz Wiseman, that book. Equal parts brilliant and mildly offensive because I saw myself in it way more than I wanted to. And I've done a lot of work with this over the years as a certified multipliers facilitator and in real conversations with leaders trying to get this right. And I can tell you, this shows up everywhere. I remember reading it and thinking, oh, I do that. Oh no, I really do that. Okay, wow, I need to stop doing that. Wiseman talks about two types of leaders: multipliers who amplify the intelligence and capability of others, and diminishers who often unintentionally shut it down. And here's the kicker: most diminishers don't mean to be that way. They're trying to help, they're trying to support, they're trying to make things easier. Sound familiar? Think about this. How many times have you stepped in because it'll just be faster if I do it? Or they're struggling, I should help. Or I don't want them to fail. So you give the answer, you solve the problem, you take over. And in the moment, it feels helpful. But what pattern are you creating? Dependence instead of independence. It's the classic, do you give them a fish or do you teach them how to fish for themselves? And let's be honest, sometimes teaching them how to fish is slower, messier, usually, more frustrating? Absolutely. Especially when you know the answer. But let me ask you this: what are the most powerful lessons you've learned in your life? Not the easy ones, not the ones someone handed to you on a silver platter, the real ones, the ones that stuck. Yeah. Those were probably a little uncomfortable, maybe even painful, because you had to figure them out. Now, this doesn't mean that we just sit back and let people struggle endlessly. That's not leadership either. There's an art to this. It's stepping in enough to guide without taking over. It's helping them get unstuck, then handing the ownership back. And one of the simplest ways to do that is ask instead of tell. I know it sounds so simple, and yet it is so hard. Because you're sitting there thinking, I already know the answer. Why do we have to play 20 questions? But those questions, that's where the growth happens. So, how do we stop getting it wrong even when our intentions are right? Here's a couple things you can focus on. One, never stop learning. Acknowledge and accept that you don't know everything. I don't know everything. Nobody does. The moment you think you've arrived is the moment you stop growing. Two, ask instead of tell. Not always, not in a crisis, but more often than you think you have the opportunity to ask. Three, seek feedback. Yeah, I know this one's uncomfortable. It's tough and it's crucial. Ask your team, your family, your friends, what's working, what's not. How can I do better? This gets even harder the more senior you get. But it's important to remember that feedback is just information. And information is how we get better. Four, enlist the help of professionals. Look, I didn't and I won't magically become a better dog handler overnight. I'm getting help. Same with leadership, coaches, mentors, books, workshops. You don't have to figure this out alone. And honestly, you shouldn't. Okay, so here's your challenge for this week. I call this the pause before you pounce challenge. The next time someone comes to you with a problem, before you jump in with the answer, pause. And instead ask one question. Just one. Try what do you think we should do? What options have you already considered? What feels like a good next step? Then let them think. Yeah. It might be awkward. Yes, it might take longer. Yes, you might have to resist every urge in your body to just jump in. But watch what happens. Watch how they start to step up. Watch how their confidence grows. Watch how your role shifts from problem solver to leader. And if this episode hit home for you, if you had one of those, oh wow, I do that moments. Don't keep this to yourself. Think of one person, just one who needs to hear it and send it to them right now, not later, now. And if you haven't already, hit the follow button so you don't miss what's coming next because we're just getting started. And if you're feeling bold, leave a review. Not the polished professional kind. I would love the real one. The this called me out in the best way kind. The I didn't want to hear it, but I really needed to, kind. Because that's how this message reaches more leaders who are ready to actually lead differently. Now remember, leadership isn't about having all the answers, it's about creating the space for others to find theirs. Even if it means occasionally getting humbled by your dog. Until next time, stay real, stay raw, and keep leading with swagger.