She’s That Founder
207 | Why Trying to Be a “Good Leader” Won’t Help You Lead Better and the 4 Questions That Will
I think trying to be a good leader is making some of us worse leaders.
Hey, hey, hey. You're listening to She's That Founder, the podcast for ambitious female leaders who are ready to stop being the bottleneck in their business by using AI frameworks for faster delegation and decision-making.
I'm Dawn Andrews, and today you'll discover why the checklist you've been measuring your leadership against was never something a human being could actually accomplish.
The four questions that replace what would a good leader do with something you can actually use in the room, and how to tell the difference between what this moment may need from you and what would just make you feel better
Happy Tuesday, everybody. It's great to be back.
A few months ago, I'm really excited to share this topic with you today. I was thinking about it. A few months ago, I had a hard conversation I needed to have with someone on my team, and I did the thing I always do before something like that. I made a list in my head.
Should I be more direct? Should I lead with empathy first? Am I being a pushover if I give her more time? Am I being a hardass if I don't? Should this be collaborative, where we figure it out together, or should I just tell her what I need? Am I supposed to be vulnerable here, or is vulnerable the wrong move for what this person actually needs from me right now?
Like, the amount of questions that I asked myself just to deliver this piece of feedback was utterly ridiculous. I was standing in my kitchen with my tea going cold, running through this list of leadership virtues like I was trying to pass some kind of test. Like, be decisive, be empathetic, be confident, be approachable, have boundaries, be inspiring, be calm under pressure.
I mean, good Lord. And somewhere in there, I thought, "This is insane. I'm trying to be 11 things at once to one human being in one conversation, and there is no version of me that can hold all of that at the same time." 24 years of this work, using tools, teaching leaders how to be better leaders, and I still stood in my kitchen running the checklist like I hadn't written half of it myself for other people.
Like I didn't even know what I was doing. And that's what I wanna unpack with you today because I don't think I'm the only one doing this. If you've ever stood in your own kitchen or your rear view mirror in your car or your bathroom mirror running through a list like that before having a hard conversation, I want you to know that you're not alone in it, and you're not doing anything wrong by wanting to get it right.
Here's what I've noticed in myself and in almost every founder and leader that I work with. We've been handed this composite definition of what a good leader is. She's supposed to be empathetic and decisive, vulnerable and confident, collaborative and authoritative, approachable and boundaried, inspiring and accountable, emotionally intelligent and calm under pressure and transparent all at once, all at the same time.
It reminds me of America Ferrera's speech in the Barbie movie, right? We're trying to do all of that simultaneously, and I challenge you to do it. Go ahead. I will wait. But we can't. Nobody can. And this was a checklist that none of us could ever actually complete. And I wanna be really clear about something here, because I'm not about to tell you that empathy is a problem, or vulnerability is a problem, or collaboration is a problem.
None of those qualities are wrong. I believe in every single one of them. The problem is thinking that all of them are correct in every moment, no matter who's in front of you or what's actually happening. And here's the part that makes it worse for us specifically.
In my work, I hear these phrases constantly: psychological safety, servant leadership, leading with empathy, bringing your whole self to work. These are beautiful concepts, and I actually believe in most of them, but nobody translates them into an actual behavior, and without that, they stop being useful ideas and start being a standard we judge ourselves against without ever being told what we're supposed to do.
It's an unwinnable game. And the story that you might be telling yourself is, "If I could just learn the right leadership behaviors, nobody would be disappointed in me. My team would like me, my board would approve, my boss would think I'm amazing, nobody would quit, nobody would think I'm difficult."
I mean, wouldn't that be lovely? But leadership isn't a collection of virtues that you're supposed to perform. It's a practice of making choices, and those are two completely different jobs. So if it's not about performing the right behaviors, what is it about? And this is where it gets really interesting.
I have a thing, and if you've been listening to me for a while, you already know this about me. I like being right. If I'm right, that means everyone else has to be wrong, and some sick little part of me finds that really satisfying. There have been plenty of moments where I just wanted to tell someone exactly what to do because I was tired of holding space for the process to unfold, and there have been just as many moments where I avoided saying the hard thing because some part of me wanted to be liked more than I wanted to be honest.
None of that makes me a bad leader. It makes me a human being, and trying to lead other complex human beings inside multi-human being systems, which is a phrase I use constantly because it's the truest thing I know about work. Here's what I think is going on underneath this good leader obsession.
It gives us the illusion that there is a correct answer, that if we just find it and perform it well enough, nothing bad will happen. Nobody will leave. Nobody will hate the decision. The thing will work. And right now, we have such spectacular examples of bad leadership in the world, I think it makes us want this even more.
But leadership, by its nature, is responsibility without certainty. You can make a decision that is thoughtful and compassionate and strategically sound, and somebody can still hate it. Somebody can still walk out the door. Something can still fail, and that's not a sign that you did it wrong. That's the job.
So stay with me, because this is the actual reframe that might unlock something for you. Sometimes good leadership means listening. Sometimes it means making the call and saying, "Nope, we're doing this." Sometimes it means asking more questions. Sometimes it means giving someone another chance. Sometimes it means ending the relationship.
Sometimes the person in front of you does not need your vulnerability. They need your clarity. And do you ever have that moment where you genuinely don't know which one it is? Leadership isn't a thing that you perform.
Leadership is figuring out what behavior creates the outcome that you're responsible for with actual complicated people in a specific moment. Context like reading the room and knowing what to do is the whole job, and it is not an easy job. So I'm inviting you to stop asking what a good leader would do, and start asking, "What does this moment require of me?"
Which is nice to say, and genuinely useless if I don't give you a way to actually do it. So here's what I use. We'll be right back. Okay, real quick, before we get into the four questions that will help you lead with more ease. If you're the kind of leader who wants real usable tools instead of another vague framework, I put together a free guide called 10 Ways AI Will Make You a Better Leader.
It's specific, it's practical, and it's built for exactly the kind of judgment calls we're talking about today. It's linked in the show notes. We're early adopters over here for a reason, and I can't wait to share it with you, so go grab it. The link's in the show notes.
And we're back. Okay, four questions.
This is what I started using instead of running that virtue checklist that I was talking about earlier, and I'm just saying sometimes I run the checklist anyway and then have to, like, reorient myself. I'm a human being. Sometimes I get a little carried away. But I think these four questions will help you to read the room, so to speak, and figure out what that moment requires of you for the person that you're working with.
Okay, question one: What outcome am I responsible for creating?
So start with the result. What actually needs to happen here? Not the leadership technique, not empathy, vulnerability, et cetera. What's the result you're trying to get? You trying to meet a particular deadline, generate some sort of revenue number? Like, what are you trying to accomplish?
Number two: What does the person or the team actually need from me right now?
So if you're trying to raise revenue by 20% this quarter, what does the person or the team in front of you actually need right now? Do they need clarity, context, a decision, a question answered, coaching on how to do something, a boundary set, space, some sort of how-to?
If you're asking yourself about this person in relationship to the result, something will rise to the top really quickly.
Number three, what am I tempted to do because it makes me more comfortable?
This is the one that gets real. Am I avoiding the conversation because I wanna be liked? Am I making the call myself because uncertainty makes me a little crazy, and I just want it to go the way I want it to go?
Am I asking for consensus because I don't want anyone angry with me? Am I giving someone another chance because ending something feels hard? You have to separate what serves the outcome from what relieves your own discomfort as the leader.
And ooh, girl, I know it's hard, because those are not the same thing, even when they might feel identical in the same moment.But this is where you stop stepping on your own toes.
And then question number four, what action best serves the larger intention?
And then take action. Not perfectly, not without emotion, not knowing exactly how everybody's gonna respond, but deliberately, intentionally. And I wanna be really clear about something because I don't want you walking away thinking the outcome justifies whatever it takes to get there.
That is not what I'm saying. The standard was never get the result at any cost. The standard is holding the outcome, the people, the context, your values, and your responsibilities all at the same time and making the best decision you can with all of it in your hands. This shows up the same way whether you're managing one employee or running a company.
Should I give her more time? Should I make the call myself? Should I tell the client no? Should I delegate something? Should I protect revenue or protect the team?
If you're leading at a higher level, it just gets more layered and complex because you're weighing the employee, the health of the team, the business, the politics, the precedent, the culture, the risk, and what your own boss expects all at once. And there may be no clean answer, but that's leadership, too. So the translation, no leadership checklist that answers those for you.
Your judgment does. That's the actual skill. Not the virtues, the judgment of when to use those virtues. So you're not failing at leadership because you don't have the right traits. You're building the muscle of judgment, and that only comes from using it and living with the consequences
So here's what we covered today.
The good leader checklist was never something you could actually finish because it was never a checklist to begin with. It's a practice of choices. Leadership is responsibility without certainty, which means the goal was never to get it perfectly right. And the four questions, what outcome am I responsible for?
What does this person need? What am I doing for my own comfort? What serves the bigger intention? Those are what you use instead. And here's what I wanna ask you to do this week. Next time you catch yourself asking, "Am I being a good leader right now?" Stop and ask the third question instead, " What am I tempted to do because it would make me more comfortable?"
You don't even have to act differently yet. Just notice where your comfort and the outcome split apart, and that noticing is where the whole thing starts. And if this is the kind of leadership conversation your organization needs more of, this is also the work that I do outside the podcast through executive coaching, women's leadership development, speaking, and custom leadership programs.
And you'll find all of that at the link in the show notes.
There isn't one version of you that becomes the good leader and gets to stay there. Leadership is a practice. The target is always moving. Different person, different moment, different problem, same responsibility. So lift your head, look at what you're actually trying to create, and choose what this moment requires from you.
That's it for today's episode of She's That Founder. I'll see you on Thursday, and until then, you've got this. Stop performing the checklist and start trusting your judgment. See you later, Lovey.
