2278 - A Roadmap for Effective Leadership Conversations with The Ready Zone's Esther Weinberg

0:04Well, hey, Thoughtful Leader. Welcome to the Thoughtful Entrepreneur. On this show, I interview purpose-driven founders, experts, and change makers who are making a real impact in the world. Want to be a guest? Simple. Go to upmyinfluence.com and click podcast. I'd love to promote your story to our audience of over 100 ,000 and across over 2 ,300 daily episodes and counting. Want to get booked on other great shows like this? Simple. Go to podverified.com and get your free guest authority score. Thousands of hosts are looking for high quality guests and Podverified connects you the right way. Now let's dive into today's episode.

0:58With us right now, it is Esther Weinberg. Esther, you are the founder and CEO of The Ready Zone. Your website is thereadyzone.com. Esther, it's great to have you. Thank you so much, Josh, for having me. That's great. You got it all right. Yeah, yeah. Well, listen, before we start talking about what The Ready Zone is and who you serve, I always love learning what other leaders are kind of into on the side or hobbies, games, movies, music, just kind of whatever they're geeking out on. Anything come to mind? Oh, you're going to laugh. So as of late now, I didn't grow up as a professional dancer, but I love I love hip hop and dance.

1:39So not classical dance, but I love to dance. And so lately I've been into Dance Dance Revolution, which is a game on Xbox and PlayStation. And it is so great because I mean, I'm the kind of person I put on. I make my own. I'm like my own DJ with these songs. and so to have a place not just me to move my body it's funny I was driving the car this morning I put on put on like a song by Pitbull and I'm like moving my butt oh yeah you know all the moves yeah I'm thinking oh my goodness so yeah it's I would say that it's probably a non-traditional thing that people are geeking out of but it's very much uh that's amazing that's that's what I love it's like so my I have questions of so I think we had uh we had it I don't know if it's Dance Dance Revolution, but I think for the Wii, like way back in the day.

2:27So I remember my kids doing it. And I'm curious if you, do you feel like it actually teaches you rhythm, coordination, choreography? Do you feel yourself improving the more you've played this? You know, it's a funny thing because it reminds me, I've been watching this documentary about Billy Joel on HBO Max. And he was talking about how when he was a kid that he would be taught certain pieces to play and then you just start riffing off of it so I find that it does teach you coordination and stepping and then I just want to riff and do something on my own that's not this that it's not the arrow scrolling up and down on the screen but yes so I think it teaches you all that I think teaches you coordination it does teach you rhythm and then for me it also makes me want to even improvise even more.

3:18Just shows you how I'm not a rule follower. Well, Esther, let's talk about the ready zone. Give us an overview of the work you do. Yeah. So the short answer is that I help CEOs and executive teams grow and keep their best people to scale without confusion and solve the people side of technology and transformation. If you think about it, the three areas is the three T's, talent, keeping and growing the best people, traction, growing and scaling right, and also technology. How do you merge people with technology? Because today, people are so really freaked out, understandably, about AI and the advent of AI and the impact.

4:06But what I do is I really get underneath the surface and figure out what's really slowing things down, whether that's how people lead, they communicate, make decisions together. And oftentimes it's these hidden beliefs or what people are avoiding, these avoidance patterns and those dynamics or underdeveloped leadership depth that's quietly shaping and getting in the way of everything. So, you know, what they get as a result, they get better attention of top talent. They get faster, cleaner execution and they get leadership teams that operate at a higher level and a culture that can actually support the pace of growth that you're driving.

4:43Sometimes you can grow so fast and the culture doesn't grow. And then there's real speed bumps along the way and companies that grow without burning people out or breaking what makes them great in the first place. So that's really the backbone of everything I do. Yeah. Well, Esther, I would love your kind of take on where we are like in 2025 here. What trends have you been seeing in your world that you think are valuable for an audience of a lot of SMB founders and leaders that listen to the show? Yeah, I would say that, you know, what I'm seeing is that, you know, the real trends that I'm seeing, the major trends I'm seeing is that companies are growing, but leadership isn't growing with them.

5:30It's always growing with them. So here's the three most common trends that I hear across companies, private equity firms, CEOs right now. One, and there's not necessarily any order, but number one, talent is the number one conversation before, during, and after the deal. That's whether you're getting private equity or you're a fast-growing founder-led business. Talent is the lever in the risk. So finding it is tough. Keeping it is even harder. And very few leaders are asking, how confident are we that our current team can lead where we're going? So most aren't evaluating that clearly before a deal closes or they realize too late that the leadership team isn't set up to scale.

6:08Second thing is there's a leadership gap between ambition and execution. So CEOs often tell me I've hit a wall, we're making money, but I can't tell if this is a retention issue, a hiring issue, or a leadership issue. And what's often missing is that mid-level and senior leaders were never developed. Sometimes frankly the founders have never even developed. So CEOs keep getting pulled in the weeds trying to grow and lead at the same time, but with no space to think. And then the third thing is that there's no room to slow down, no clear framework for how to lead in complexity. So if you think about it, many leaders I work with are overwhelmed by competing advice with shifting goals, nonstop pressure that we're all under today, right?

6:51So they're trying to deliver today while building tomorrow, but without really clear communication, prioritization, or leadership and accountability in place. One CEO said to me, when I finally get the right people in the right seats, I can look up and think, but until then I'm underwater. But the truth is also that people aren't really having the kind of conversations, real tough conversations, because nice people don't tell people the truth always. And so that's where performance quietly breaks down at the human level. That's where I'd say that. As you were sharing, I just, a thought came to my mind about a blind spot that I think I have, and I suspect that others have this too.

7:28I, you know, like a lot of founders that just have this red hot passionate desire to learn and grow and just this unquenchable appetite to pursue these things. That's not necessarily the norm for all leaders. And I think for those of us who have just that incredibly self-directed, I don't need anybody to tell me, you know, I'm going to just passionately pursue the things I want to learn. But that is a major blind spot for me because I would assume that my other leaders in the organization would be doing likewise. Maybe not the case. And so if I can influence that proactively, I probably should rather than just assuming that they're reading the same books that I am.

8:13I know they're not. Yeah. Yeah, I think, look, I think that the other thing too is that I think as leaders, we can't expect, like I had this happen with the CEO the other day. He's telling me that he had a leader in one part of his business. He moved into another leader. He's not performing the same way. He's really disappointed that he's not having the same, he's not performing at the same level. He's really believed in him. He's not having the same passion and conviction that he had. And when I said to him, simple thing, but really important, I said, does he know your expectations? And he said, I think so.

8:47I said, think is not knowing. So you either know or you don't know. Like if I put you in a stand of a court of law, you put your hand on a stack of Bibles and you swore, could you actually swear that you understood what your expectations are? And he said to me very eloquently, he said, no, I can't actually say that. But how would I even know that? And I said, well, first you'd have to ensure to convey it, number one. Number two is after you do, all you need to do is say to somebody, and this is my language, you'd have to wordsmith this for yourself. What I have to say to somebody is, you know, we've talked about a lot of things today.

9:16I've shared my expectations. What are you really taking away from what you're hearing that I'm sharing that my expectations are? What are your expectations? So this way we get on the same page because I can't, as a founder, as I'm starting to grow and scale an organization, I'm not the one driving everything. So you have to make sure that you're bringing people with you, not leaving them far behind. uh esther your background uh is in the entertainment industry um you got to do some really cool stuff uh especially i mean i love the intersection of like uh media relations uh with disney and espn uh i i i boy i'd love to geek out with you on this we'll talk about maybe the state of the industry right now but i'd really love to learn like how that has informed the work that you do today, your experience there?

10:06You know, it's so interesting. I remember there was a real inflection point a few years ago when I decided that I would pick up and I would move to Uganda, Africa, and I would run my business out of Uganda, Africa in the evening. And then during the day, I would do international development work. And so I'm working with these high power media companies like Netflix, Warner Brothers, NBC Universal, Nike. and during the day I'm dealing with children's rights and issues really affecting kids on the ground, stories that can make your hair stand on them. But I found one thing very, very similar is that people are people.

10:43And the issues that people, the organizations that I'm working with on the ground in Uganda are going, are the same as the ones in media companies. Media companies are dealing with, why is decision-making slower and consistent? Why are people that are great for me leaving? Why are we trying to grow, but why is that stall? Why isn't my team performing at the level that I need? That is agnostic as far as if you're in the media business or you're not in the media business. If I'm running an organization and it can be in the ground of Africa, of course, the context that I'm living in is quite different, but it's still as personal to me as someone who's running in the middle of a media organization too.

11:23Yeah. Esther, who do you work with today? What types of companies? And maybe if you want to share a story about someone you're working with specifically, that'd be great. Yeah. So I, so currently my focus, so I still do work with media companies and I really do the more of my main focus is working with CEOs, the C-suite and senior executives of businesses that are between 20 and a hundred million dollars. So if you think about it, people that are going through the issues that I mentioned before, talent, traction, technology, growing and scaling quickly. Like one CEO said to me the other day, He said, my business is going to grow.

11:59We're aiming to grow between 20 and$50 million. But do we, A, have the leadership team in place to grow from 20 to 50? Because you know this. You built a business. You've grown it to that$20 million mark, whatever the mark that you have is. And then you want to grow it now to 50. But can that same team take you there? Not always. Or not with up-leveling. Second thing he said to me is, do I even want it? So there's real different kinds of issues that I'm working with C-suite leaders on. And one thing I'm very much working with people on is working with people also on what are the kinds of conversations we need to have that's going to make the business move forward.

12:41So I'll give you an example. I was working with a head of HR at a company, and that was about to double in size. And on paper, she had everything. Title, the trust of the CEO, the experience. I mean, she's a chief HR officer, for God's sakes. But behind the scenes, she felt stuck. And she said to me, it's easier to stay behind the scenes rather than be taken seriously and not rather than not be taken seriously. She's polished, composed. She ran interference for the whole executive team. But under the surface, she was frustrated and resigned and afraid of being really misunderstood. So how effective can you be?

13:16And you you may know someone like that or, frankly, you may be in that boat yourself. but what worked what we worked on wasn't tactical I know it sounds weird it was a skill gap now it was the underlying belief system that was running the show and I have a framework that I use with people called the five a's which is the five a's stand for aware acquire I'm sorry aware accurate acquire accountability and action which what I mean by that is what the five a's are number one the first day is aware, what feelings am I aware of? Now, I know feelings aren't facts, but as a colleague of mine says, they're road signs to what's most important to you.

13:56So she finally admitted that she was operating from fear, frustration, and resignation, and she convinced herself that staying small was the safest way to building trust. Then accurate, what is actually true? She believed that her voice didn't really matter, but the truth was she hadn't tested it, that she wasn't speaking up in ways that her peers could really hear and respond to, and then acquire, what is this moment here to teach me? Not you, me. And so she realized she's a trained performer, amazing singer. So on stage, she's bold, expressive, magnetic, but she realized she'd been hiding herself at work and it was costing her influence.

14:36Accountability, where am I responsible? She saw that no one was actually dismissing her, that she was doing that herself by shrinking holding back and what an action is what am I now going to do differently is she stopped being the fixer she delegated more she started speaking up with a lot more clarity and authority and in a way and also she knew it was a groundbreaking exercise when she walked into the CEO's office instead of sitting down and talk to him she goes let's go for a walk let's go for a walk and talk about it because it was better he was more effective if they would have that kind of side to side conversation that I'm sending across from you.

15:11And people started listening and she didn't force influence. She became it. And the result is she went from hiding in plain sight to shaping the company's growth strategy at one of the most critical times in their history. So she even said to me, she goes, look, the five A's didn't just help me prepare for having this kind of conversation. It helped me become someone who no longer even avoids it anymore. more. You, your website is thereadyzone.com. When somebody goes there, Esther, what would you recommend they do? And I know you've got some free resources as well. Yeah, the first thing I would suggest people do is download my book, because I think that my ebook of better leaders, better people, better results, six eye-opening strategies to thrive through change you didn't ask for.

15:57The reason why I say that is because I know that if you're listening to this podcast, you're looking for practical tools and strategies you can use today. Not some theory and data is great, but you really want tools. And that has tools and strategies you can start implementing today that can shift your leadership. I like it. Better leaders, better people, better results. Six eye-opening strategies to thrive through change you didn't ask for. That is available right now for free. You can download it at thereadyzone.com. Esther Weinberg, founder and CEO of The Ready Zone. It's been a great conversation.

16:33Thank you for joining us. Thank you so much, Josh. Appreciate you.

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