214 | I Need More Confidence Is the Wrong Diagnosis | Leadership, Delegation & Systems with AI Frameworks

You froze in the room. Lost your words, your footing, maybe your own content. And the advice showed up right on schedule: you just need more confidence.

Sometimes your hesitation as a leader isn't a confidence challenge. It's useful information.

I got essentially fired from a two-day sales retreat I was hired to lead. I knew the material cold. I'm a confident, engaging speaker, and that's not a brag; it's the setup. Mid-sentence, in front of everyone, the executive who hired me cut in and redirected the room. The call was right. I didn't see it.

What followed was every public speaking nightmare at once. But I didn't lack confidence. I had plenty. That was the whole problem. What I was missing was context: who had influence, what happened before I walked in, the agenda underneath the agenda. No power pose was going to save me.

"I need more confidence" isn't a category you can work on. Confidence to do what, exactly? Raise your prices? Tell your CEO she's wrong? Lead 300 people instead of 30? Each one takes different knowledge, skills, relationships, and practice.

In this episode:

• Why “pop” confidence advice helps you walk through the door but can't prepare you for the room
• The better question to ask the next time you're googling "how do I become more confident"
• Why the woman who waits sometimes understands the stakes better than the one who jumped in first

SKILL, CONTEXT, OR POWER
Before you call it a confidence challenge, ask what's missing.

Skill: Practice it. This is where confidence is real; it just shows up on a different schedule. Not "I feel confident." More like "I have evidence I can deal with this. I've screwed it up before and recovered."

Context: Go get it. Ask more questions. Listen longer than feels comfortable. Learn who's really deciding, what they care about, what they're afraid of.

Power: Learn how it works and where it lives. Who has authority? Who has influence? What is the senior person trying to solve that you can't see from your seat? Whose support matters before the meeting ever happens? Taking up space without understanding the space is incomplete advice, and it can be dangerous.

And access isn't equal. The 2025 Women in the Workplace report found only 31% of entry-level women have a sponsor, compared with 45% of entry-level men. You can't affirm your way into a relationship you don't have access to.

TRY THIS THIS WEEK
Pick one thing you've been calling a confidence challenge. Ask yourself, out loud if you can: is what's missing here skill, context, or power? Then go get that one thing.

SEND THIS TO ONE WOMAN
Think of one woman who's been told she needs more confidence. Send her this episode. What she may need is better information, better preparation, or more power, and she deserves someone who will help her figure out which one.

RESOURCES
Women in the Workplace 2025, McKinsey & Company and LeanIn.Org
The West Wing and Scandal, for a crash course in how power moves through rooms

CHAPTERS
[00:00] The day I got overridden in front of the whole room
[02:30] Plenty of confidence, zero context
[03:30] What a power pose can't tell you
[05:50] Skill, context, or power?
[09:00] When patience looks like hesitation

The confidence comes afterwards.

Send this episode to one woman who's been told she needs more confidence. This comes straight from your on-air ask, and it fits a Thursday episode, whose job is growing the audience.

"Confidence isn't something you put on before the risk. It comes afterwards."

RELATED EPISODES

• EP 207 | Why Trying to Be a "Good Leader" Won't Help You Lead Better and the 4 Questions That Will 
• EP 208 | Your Confidence Isn't the Problem. Build Power Literacy So You Know When to Push, Wait, or Walk Away
• EP 213 | Fear in a Cute Blazer. Why More Research Won't Make Decision-Making Easier

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Transcript

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She’s That Founder
214 | I Need More Confidence Is the Wrong Diagnosis

Sometimes your hesitation as a leader isn't a confidence challenge, it's information.

Hey, hey, hey. Welcome to She's That Founder, Thursday Edition. These are the quick rants, kick in the pants, velvet boot moments that represent me standing in the future, pulling you toward the even stronger, better, more powerful version of yourself with AI as your co-pilot

Let me tell you about the time I got fired. Okay, essentially fired. Let's call it what it was. I was hired to lead a massive two-day sales meeting and retreat. I built the program, I knew the material cold, and I'm going to say this plainly because it matters for the story.

I am a confident, engaging public speaker, and that is not a brag, that is the setup. So I walk into that room believing that my job is to lead, and I lead hard. There's one part of the discussion where I'm moving the room towards a conclusion, and I know where this conversation is meant to land, and I'm driving us there.

And the executive who hired me, the person whose event this is, cuts in, like mid-sentence while I'm speaking, and says, We're staying on the topic that we're on." And this was a moment to let the room air out their concerns and their frustrations, so I get it. But here's the part that makes this story really hard to tell.

The call was right. It was what the room needed, and I did not see it. The delivery, though, rude. A sidebar would've been nice, but instead, I got overridden in front of everyone, and it stepped all over the rapport I'd built and the credibility that I was standing on. I could blame the person for the interruption, but I actually don't. When I'm stuck or when things like this happen, generally I just say what's so and go from there, and here's what's so.

I was overly confident in my approach to that event and to leading, and I was naive about what was actually going on with the people in that room. And in the moment, what happened after that was every public speaking nightmare you can think of. I couldn't find my words. I couldn't find my footing in the content, my own content.

I felt like I was having a hot flash right there in front of everyone. I felt like the whole room was looking at me funny, and there were actually a lot of sympathetic faces out there, but that's not what it felt like. It was an out-of-body experience.

If this were purely a confidence conversation, like if I was speaking to a confidence expert, this is how I feel like it would go The expert would say, "She got rattled. She needs to own her power, stand tall, and breathe, and walk back in." But did I lack confidence in the story that I just told you?

Seriously? I had plenty of fucking confidence. That was the whole challenge. Confidence wasn't what I was missing. What I was missing was context. I needed to ask more questions. I needed to listen more. I needed to understand the people that were gathered in that room and who had influence, who followed the leader and who didn't, what had happened before I got there, and what those people needed from my two days besides the things that we had put into the agenda.

The, you know, the agenda underneath the agenda. Before I assumed that knowing how to lead the session meant I understood what was happening inside it, and no power pose was gonna save me here.

And this is what's got me really fired up today, and why most confidence advice drives me absolutely bananas. Power poses, affirmations, mantras, journaling prompts, dressing differently, 30 ways to look more confident in your next meeting. That is false you-go-girl energy, and I'm so over it.

And look, maybe standing differently changes how you feel in that moment walking through the door. Great. I mean, seriously, great. That is great. Those things may help you for a moment, but they don't necessarily help you prepare for the moment. Because a power pose can't tell you who's really making decisions, what that person cares about, what they're afraid of, what happened in that room before you walked in, what this decision touches downstream, or what objection you haven't seen coming.

What you actually need to know how to do. That's where confidence advice, like pop confidence advice, stops being useful and starts being inadequate leadership advice. Here's the bigger thing. "I need more confidence" isn't a category. As a category, you can't work on it.

Confidence to do what exactly? Raise your prices? Fire someone you've worked with for eight years? Ask an investor for money? Tell your CEO that she's wrong? Walk into a board meeting? Launch something that might fail? Lead 300 people instead of 30? The confidence required for each of those is not the same thing.

 Each one takes different knowledge, different skills, different relationships, different practice. So how do I become more confident is a real question. It is a question that people ask. It has a ridiculous number of Google searches. But I feel like it's the wrong question.

The better question is, what would make me more capable of handling this specific situation? And in fact, one of my invitations right here right now is if you find yourself googling how do I have more confidence, how do I build self-esteem, I would ask you to transfer that question, to transpose it into what would make me more capable of handling X situation.

Whatever it is that has you googling how do I become more confident, what's the situation that's preceding it? So I mean, real talk here. Confidence isn't the thing. What's missing is the thing. So before you call it a confidence challenge, ask yourself what's missing here.

Skills, context, or power? If it's skill, you can practice, and this is where I'll give confidence its due because it's real. It shows up on a different schedule than we've been told. Not I feel confident. More like I have evidence that I can deal with this situation. I've practiced. I've screwed it up before and recovered.

I know what I know, and I know what I don't know, and I trust myself to figure out the part that I couldn't see coming. That is confidence built from practicing a skill and becoming better at it, increasing your self-efficacy and capability. Confidence isn't something you put on before the risk. It comes afterwards, after you take the swing, after you miss, after you find out that you survived, after you get better and do it again.

Fail up every single day. I literally have that written on my wall. So that's the skills part. If it's context that you need, if that's why you're asking for more confidence, you go get it. You go ask the questions, you listen longer than feels comfortable sometimes to people, and this was me in that room when I totally ate it.

And if it's power that has you asking for more confidence, that's a different conversation. And I wanna be careful here because telling people to speak up isn't terrible advice, but some days 28-year-old me just needed to hear someone tell her to say the fucking thing, to take the risk, and find out what happens.

And I needed some of that at 38, too. But once the stakes get bigger, the higher up you go on the leadership ladder, willingness to speak isn't enough. Power isn't given, it's taken, and God, I really wish that wasn't the case, but you have to know how power works and where it lives. Who actually has authority in that room that you're trying to speak up in?

Who has influence? What is the senior person in the room trying to solve that you can't see from your seat? What happens if they say yes, and what happens if they say no? Whose support matters in that room before the meeting ever happens? Taking up space without understanding the space is incomplete advice, and it can be really dangerous.

You know, you want a quick lesson on power, well, maybe not quick, but I watch The West Wing. Enjoy the show, you guys, because how power moves through rooms, I mean, that's part of the reason why Scandal was such a popular show as well. It's all about how power is moving through rooms and what it takes to be able to get things done.

Corrupt power at various points, but power. And I just want to be clear, too, that this isn't always about us. The 2025 Women in the Workplace report found that only 31% of entry-level women have a sponsor or some sort of mentorship, compared with 45% of entry-level men in, across all different job types. So you can't affirmation your way into a mentorship relationship that you don't have access to, right?

Those things make a big difference in helping to learn to navigate rooms of power. And one more thing, because I don't want to turn this into a "be bold, take risks, go girl" episode. Some of the strongest women that I work with are patient.

One of them will sit with a situation much longer than people expect. She watches, she listens, she collects information, she understands the consequences, and then when it's time to move, she commits fully, and ooh, she's unstoppable.

And from the outside, that can look like being hesitant or over-prepared or even overthinking or not confident enough. And knowing her and her process, I see something completely different. I see platinum level judgment. Sometimes the woman who's waiting understands the stakes better than the person who jumped in first.

So here's where I've landed. I don't want you to be more confident. I want you to be more capable, more powerful. I want you to have more agency and self-efficacy. I want you to understand the rooms you walk into, to know what you need to learn, and to practice the skills you don't have yet.

To take the risk when the risk is what's required, and to trust yourself enough to know that if you fuck it up, you'll learn something, clean it up, and do it again. You don't have to figure out how to feel certain before you move. You just have to become increasingly certain that you can handle yourself when you do.

So here's my ask this week. Think of one woman who's been told she needs more confidence. Send her this episode, because what she may actually need is better information, better preparation, or more power, and she deserves someone who will help her figure out which one.

Take this into your week, pick one thing you're calling a confidence challenge, and ask yourself out loud if you can, is what's missing here skill, context, or power? Then go get that one thing. That's the whole assignment. I'll see you Tuesday, and until then, just remember that confidence comes afterwards, Lovey.

See you soon.