What No One Prepared Me For About Leadership
No one prepared me for most of what I would actually have to do as a leader. Not the hard conversations, the decisions I had to communicate but didn’t make, the pressure of carrying the number, or the responsibility of leading people through uncertainty while still being expected to deliver results.
I’ve spent more than 20 years inside revenue organizations, from Fortune 500 companies to growth-stage businesses, and I’ve been inside that pressure. I’ve made mistakes, stayed quiet when I should have spoken, spoken up without clarity, and tried to solve something myself instead of developing someone else to do it. I’ve also learned that leadership is deeply human, and that behind the data, the performance, and the results are the people you are responsible for leading.
In this episode of The Real Work of Leadership, I’m sharing more about my own leadership journey, the experiences that shaped how I think about coaching, accountability, and developing people, and the mistakes that taught me some of the hardest lessons. I’m also talking about why I believe we need more honest conversations about what leadership actually requires, especially the parts no one prepares you for.
0:33 – Why Elisa is talking about leadership in the first place
1:21 – More than 20 years inside revenue organizations and under real pressure
3:00 – Looking beyond the data to understand the people behind it
4:38 – Leadership as a responsibility to develop the people in your care
6:06 – Taking over a team at 52% to goal and leading the former manager
7:55 – Communicating decisions you didn’t make and leading through uncertainty
9:55 – Getting clear on your reason for wanting to lead
13:08 – Understanding what actually drives the people on your team
15:14 – Coaching individuals differently instead of expecting everyone to work like you
17:03 – Making mistakes, letting people fail, and learning instead of jumping in to save them
18:54 – The gap between leadership theory and the actual work of leading
21:51 – Why Elisa is willing to talk about the failures and trade-offs leadership demands
Mentioned in What No One Prepared Me For About Leadership
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Elisa Hawkins: Leadership theory is easy. Leading actual people while you're managing up, putting out fires, thinking strategically, and still trying to hit the number is something else entirely. Hi, I'm Elisa Hawkins, and welcome to The Real Work of Leadership. We're getting into the conversations, decisions, organizational dynamics, and real-life pressure that come with leading a team and being responsible for the results.
So last time, we talked about what this podcast is all about. And on this episode, I want to talk about why the heck should you listen to me? I mean, who the hell is Elisa to be talking to us about leadership, right? Well, I'm not here because I believe I've done leadership perfectly. As a matter of fact, I haven't. I've made a lot of mistakes and I have had a lot of things that I've learned from and wins from the mistakes. And when I talk about wins in leadership, I'm not talking about customer wins. I'm just talking about learning from the mistakes that I made because you know what? Here's the thing. No one prepared me for 90% of what I was going to do in the real work behind leadership. I'm here because I've spent more than 20 years doing that, carrying the number, both from a new business perspective to a customer success perspective, from small business to mid-market to national enterprise accounts. I've built teams.
I have built strategy, I have built processes, and I've made some decisions under some very intense pressure. Fixing what was not working and then learning some really hard lessons along the way.
So I've spent over 20 years inside revenue organizations from Fortune 500 companies to growth-stage companies. They have run the gamut of industries from tech to distribution where I served multiple industries. So I have seen all kinds of different environments from large corporate structures to really scrappy growth-stage startups. And my progression came from starting at a very individual contributor level, whether it be small to mid-market business, and then growing into enterprise, major account sales, and also into customer success. And then developed myself to get into leadership, both at a team level, so as a district sales manager, all the way up to VP level responsibility. I have built the teams. I have coached leaders and sellers. I have improved underperforming organizations where I went in and not only did I dig into the data because part of leadership, yes, is analyzing data and thoughtfully thinking about it.
But behind that data is the humans behind that, right? And I'm not just talking about the humans on the teams you lead. It could be the customers. What is the data telling us? What is actually driving what the data is telling us? Is it from, hey, we're performing extremely well, in these certain areas, why are we performing extremely well? Or this individual is doing as consistently month over month, quarter over quarter, year over year, hitting their goals, and the team thinks great of them. What are they doing? Right? So one of the things that I love to do when I'm analyzing data is ask a lot of questions surrounding it. It's not just the good things. If I'm analyzing data that's not telling a pretty picture, I always say, data tells a story. Sometimes it's good, sometimes it's bad. That's for sure, right? But always behind that are going to be questions that we ask ourselves as leaders. What is this actually telling us?
And what is the why behind that? I understand what it takes to build teams. I understand what it takes to coach. Coaching is my absolute favorite part of leadership. And I've really carried direct accountability and responsibility, not just for the revenue and performance, but also for the human beings that are in my care. And I very much look at leadership as a service because it is our responsibility as leaders to develop our teams, to develop individuals, to develop the human beings that are on our team. They are in our care while they are with our organization and on our team. I very much look at leadership as a service. And if you want to call it servant leadership, if you want to call it leadership, service leadership, whatever you'd like to call it, I view my responsibility as a leader in service of not only the organization, but more importantly, the team that I lead.
And I've seen multiple sides of leadership from the person trying to earn the opportunity, which I was one. And hey, listen, when I was going after my first leadership role, my direct manager leader, she did not necessarily want me to leave her team. Not because she didn't think I was capable, but because she was going to lose her highest performer on the team, right? We're going to talk about that in future episodes, but being the person who tried to earn the opportunity and then also coaching other people in navigating how to earn and strategically seek after their next opportunity, whether it be in leadership or it could be in a different role within the company. I've been that newly promoted leader, where I came into a team that, quite frankly, was all over the place. They were at 52% to goal. They had half, 50% of the sales team was on a performance plan. And I also had to lead the former manager who had been demoted.
So those were all very messy circumstances that I was not prepared for. So I've been the newly promoted leader. I understand what that looks like. I've experienced it and really and truly made mistakes, but then also came out of it with such a deep knowledge of what it takes to be a great leader from actually the team and from their feedback that they gave me.
I have been the executive carrying the number for an entire sales organization and responsible for sometimes having to deliver news that I did not personally agree with. Unfortunately, I've had to let go of people as a newly promoted leader, as well as an executive leader. Nobody prepares you for that. And I really want to take some time in future podcasts to really talk about preparing yourself for that, because it's never easy. And as I tell every single leader, that is the worst part of the job, whether it's for performance-related issues or not. It is the worst part of the job. And if you ever get comfortable with it, then you might need to rethink how you approach leadership, because it should never be an easy thing to do. But it has to be true human conversations that you have. I'm very passionate about that. You're going to hear that a lot.
I've been the person navigating decisions that were made above me. And those are sometimes great. It's a change that we love to have. Sometimes it is not. And I've had to be the person navigating those because as a leader, you're always going to have to communicate decisions that you did not make, that you have no authority to control, but you have the responsibility to enact. And those are things that I have done throughout my career. Sometimes it is great. Sometimes it's a great thing. Sometimes it's really challenging. Because believe me, we're going to talk about this in future episodes about leading through uncertainty and change. Because especially in this day and age, with everything we have coming at us from market economics to the AI technology disrupting so many things right now, there is a lot of uncertainty that we have to guide our teams through. And believe me, leadership is a guide.
And I talk about the messy bits of leadership a lot because I think it's really important for people to talk about the messy bits because nobody talks about it. People sometimes have the perception that leadership is this grand title. You make so much more money. Spoiler alert, no, you don't.
We're going to be talking about that in the third episode with one of my guests, Becca. Spoiler alert, you do not make more money, especially if you are leading in a revenue organization. And it was always my goal to actually ensure that the sales professionals on my team were making way more money than I was. I actually celebrated that. So if you are thinking about getting into leadership, it's the title, it's the money you really need to have conversations with people, leaders around you about that reality.
We're going to be talking about this in the future too, but I really want you to also sit with the why of leadership.
If you're thinking about getting into leadership, what is your why behind it?
My why was because I had unfortunately had so many bad leaders. They weren't bad people; they were not great leaders, and I wanted to change that. I wanted to be a great leader, that great leader that I needed in my career as an individual contributor. And a lot of that is surrounding coaching and strategy and not just about managing the numbers, but really leading with strategy and coaching and people helping me to grow. And I wanted to give that back. So I always look at it as coaching other people, not because their success is my accomplishment. In actuality, it's the opposite. Their success is their success. Because as I like to say, I can coach you 24 hours a day, seven days a week, but it's up to the person who I'm coaching, it's up to you to take action off of what we have talked about and what we've discussed.
And when you are the one doing the work, and you are the one taking the action on the coaching that has been provided to you, you are the one responsible for your success. And I truly believe that. If I can just help impact a person's career or their success in their current role with just a little help, then that's what I want to do. Because I truly believe that it is our responsibility as leaders to develop, whether it be through effective coaching, opportunities for them to improve, whatever that looks like, but also maybe sometimes having tough conversations.
There is a team member that I coached through a pretty tough time that was potentially career-affecting for her. But through coaching and having some really tough conversations in an empathetic and human way, she completely turned everything around. Not only in her career and how she approached certain things professionally, but also in her life. And I am grateful to have just been a small part of that. So sometimes we have to have tough conversations, but those tough conversations can lead to such great opportunities for the person, not only in their professional life, but maybe potentially in their personal life as well.
One of the things that changed my understanding of what leadership could be is just that, is that when I speak to individuals that are on my team or leaders, I really want to understand what drives them, what drives them both professionally and personally. So if there is a goal that they are trying to meet economically, right? Like what is driving that? There's always something driving that. I had a team member that one of the reasons that he needed to get to a certain level in his revenue growth and his commissions is because he was actually trying to buy a home for his parent. And I really took that deeply because that is something that drove me as well. And it's one of the greatest things that I will have been able to do for my mother is to help purchase a home for her. And so I really understand that.
But that's just one small example of what we as leaders should do is to understand what is driving our people on our teams: how they take in information, what kind of feedback do they prefer, how do they receive feedback, because everybody is different. And that's one of the things that really I took to heart as you heard me talk about, hopefully you listened to the first episode, is that individuals receive things differently. Every individual should have a different coaching plan because every individual has different opportunities to grow. They have different sets of skills and talents. No individual, just like no human being, is made the same. That was one of the most critical things that I understood early in my leadership journey. Each individual is going to receive things differently, needs to be coached differently. And by the way, they're not going to do the same thing as I am. And I shouldn't expect that.
And the deep understanding of the human element of leadership is really how I always wanted to approach leadership because I had been managed in a very different way. And I wanted to inject the human element into it while still driving results. Because let's face it, there is real pressure, especially if you are leading a sales team, a revenue team, customer success, any team that is responsible for driving revenue for the organization from marketing to sales to customer success. The target still has to be met. And the team is going to be looking to you for answers when something goes sideways that's maybe out of your control, maybe it's out of their control, but the team is going to be looking to you for answers, always.
And the organization is always going to evolve and change. Because if you're operating from what the company used to be versus where you want to go, it's the old adage, right? If you think you can get different results by doing the same thing, you're absolutely wrong. So organizations are constantly going to evolve and change. And that's a great thing, because if you stay the same, you're not going to grow. So we always have to change and we have to be okay with that because change is inevitable. It's how we approach it and how we learn from it that is up to us. There's not always a clean or obvious choice that can be made. Sometimes you make a decision in a moment that you think is gonna be the right one and it ends up not being that. And so then you have to pivot. And I have made mistakes. I have stayed quiet when I should have spoken. I have spoken up without clarity.
I've tried to solve something by myself instead of developing someone else to do it.
One of the things that I learned early in my leadership journey was that I needed to let sellers fail. And so many leaders that I have coached get so supremely uncomfortable with this because they don't want to lose that deal. And I'm not suggesting or advocating for you to let a seller fail on a multi-million dollar deal. Not at all. What I'm suggesting is that you cannot jump in and save them every time. They have to learn from their mistakes. And then you coach them through that and get them to take a learning and a lesson from that and ask them what they would have done differently because it is in the post-mortem, if you will, of our losses that we take so much knowledge, we gain so much feedback and knowledge from where we maybe didn't do well in that. So it's the same thing with the leader. Leaders are not 100% perfect, just as the teams that we lead are not 100% perfect. We're going to make mistakes.
But the key is learning from them. It's how we choose to move on and learn from those mistakes and apply it that's going to make the difference.
I built Her Revenue and this podcast because I saw too many capable people, especially women, receive responsibility without adequate preparation, support, or authority. I've seen traditional leadership advice that often teaches behaviors without explaining the organizational realities around them. Because again, there is leadership theory and then there is the actual work of leading. And I do not see leaders being prepared for that. And leaders need to have honest conversations about what the job actually requires. And we do not need to be afraid to talk about it.
Because just as we cannot be afraid to have a difficult conversation or a tough conversation with our team, whether it be individually or as a team, we cannot be afraid and shy away from having the honest conversations about the challenges that we face as leaders, what the job actually requires, because, leaders, if you are not prepared, or if you're a company listening to this, if you're a leader in a company, if you're a CEO or a founder and you're listening to this, if you are not preparing your leaders for the actual work of leadership, then your revenue is gonna suffer, the organization will suffer, your culture will suffer. And so it's supremely important that we have these honest conversations.
Again, I am not a leadership theorist explaining what should happen from the outside. I have been inside the pressure. I've been accountable for what happened next. I've been accountable for and in service to the teams. I've been the one who's had to deliver not-so-great information. I've had to deliver challenges that the business is facing, the organization is facing, and some things that are happening that are difficult. I've had to deliver that. I've also had to deliver some phenomenal results. I have reported out on, really, the increased revenue, the women in sales organization that I started, and what the results of that were. There have been great things because, again, I want to talk a lot about the challenges because I want to prepare people for leadership, or if you're in leadership, understand you're not alone in feeling that you're challenged in this.
But I also want us to talk about the phenomenal things that happen when we decide to have great conversations and listen to one another, because that's what it's all about.
So you should not necessarily listen because I have every answer because Lord knows I do not. But listen because I am willing to tell the truth about the questions, the decisions, the failures, and trade-offs that leadership actually demands. Thank you so much. I'll see you next time.
Thanks for listening to The Real Work of Leadership. If this episode resonated because you're navigating the real challenges of leading, building trust, managing up, making difficult decisions, and delivering results, then our Leadership Accelerator was built for you. Applications are now open for the Fall 2026 Accelerator. Visit HerRevenue.com to learn more and apply. And if you're enjoying the show, I'd be grateful if you would rate and review it at ratethispodcast.com/realwork. See you next time.
