From Stumbling into Sales to Soaring above the Crowd - With Catie Ivey

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Thank you so much. That was quite the intro in case I needed a confidence boost this morning. I'm feeling good, you know, after doing.

A few of these episodes, I think I have a career as a hype man. Everyone's like, you know, could I just hire you as a hype man just to pump me up before meetings and interviews? And I'm like, you know, I might just do that. I might just go down that path.

Could you just join my next team meeting around the first five minutes? It'll be perfect. Yes.

We can talk about that after the show is here. So. But we're gonna dive right in, because that's what people enjoy about this show, is we get right into the good stuff and into the tactics. And so I wanted to open with this. What makes sales leadership so hard?

It's a great question to start with, and to your point earlier, something we don't talk about a ton. And I think at the core, it's because we are constantly living in two worlds and focused on being great at two very different skill sets. If you think about what makes a seller great, it's typically some very different core competencies than what makes leaders or even managers really strong. And as especially frontline sales leaders. But even more so, as you move up the chain, you're responsible for really big numbers, and most of us have been sellers, and so it's so easy to revert into this, like, super salesperson mode. And I find it at every level, like, I want to just get in the trenches and close the deals and do things quickly. And at the end of the day, there's a place for that, of course. But the reality, my job is to make my people the best versions of themselves and to figure out how to maximize what they're capable of doing. So trying to bounce between those two roles constantly, it's really draining. I think that's part of what makes sales leadership so hard.

And so what sort of either systems or reminders you have in place to catch yourself? Right. When you notice yourself going into super science sales mode, how do you recognize it or how do you pull yourself back? Because there's a quote that I live by. I read it to my management team all the time. The strength of the leader can become the weakness of the team. And because you can super sales mode, we go in, but then we make it harder for our team. So, like, how do you check yourself? Like, how do you make sure you don't just go down that path?

Yeah, I don't Think I have a perfect formula for that. To be honest, I do catch myself almost every time I knee jerk reaction trying to give feedback or take charge of something. I try to pause for just a second and figure out if there's a question that I can ask, especially if it's a rep or a manager. Hey, let's think about this for a second more. What else could we be doing here? And maybe I have, of course, what I think is the right answer or the right direction. But just creating a little bit of space for that person to think or come up with a solution or propose a solution certainly builds that muscle in the reps and the managers and I think has helped me over time learn how to slow down just a little bit and create more space for people that work for me.

I love that it's about the questions, actually. I was just on vacation as you know, and my parting advice to my management team, I said w, I said, while I'm gone, what would KD ask? And I made them actually go through. I was like, not what I what would I do, it's what would I ask? What are the questions? You know, I would ask you if you brought something to me. So what are some of your go to? I'm going to split this into two. What are some of your go to questions? If a manager brings a problem to you and if a rep brings a problem to you, what are some of those questions you like to ask them to get their creative juices flowing?

I think they're actually probably more similar than we think at times because at the end of the day, most of it comes down to whether we're talking about a challenge that a rep is facing from a deal or a performance perspective or a specific deal that we're struggling to get across the finish line or we feel stuck on. There's always some underlying why that's sitting there in terms of what's creating that friction. So if it's with a manager and we're having challenges from a performance perspective or just missing some key things, my initial questions are why do we think that this is happening? Why do we think is the core? If we've got someone that's not pulling their weight or not working super hard or really struggling with motivation, there's got to be some key reasons. And you start asking questions about why and the core motivations and quite often you find that the team lead or the manager really doesn't know how that person is wired, what are their long term ambitions? Of course they know what their quarterly goal is and how much they're trying to sell right now, but what's actually driving them towards that long term. And quite often you find they haven't really tapped into either those intrinsic motivators or those long term goals and been able to tie things back. And I think it's exactly the same when we're talking about dissecting deals. If we've got an exec that's creating a bottleneck or something installed for whatever reason, there has to be core components to the why of what's causing that. And usually it's because we as sellers haven't figured those things out. We haven't gone deep enough. If you know, Sandler old school like Pain Funnel, we haven't done enough of the layering questions to really figure out outside of the product and the three or four things they gave us, what do they really care about? And those are usually the things that are getting in our way.

I absolutely love that it's the why. I don't care about the what. I know the what. I know what the numbers are. I know what the deal stage is. I know what's happening. I want to know why and how we can fix it. Now, something you just mentioned there, tapping into something. This is something I heard on one of your previous podcast episodes, and it's in your LinkedIn profile as well, is tapping into superpowers. And I love this phrase because I agree, I believe everyone has super powers, but you have to identify them and you have to pull them out of people. So talk to me a little bit about this. Right? So when you say tapping into rep superpowers, even manager superpowers, what do you mean and how do you do it?

So this was very much a personal journey for me, I think in arriving at this and recognizing how important it was because I've worked for managers that in the past that have been so fixated on the gaps or the struggles or the areas that we needed to improve, whether it was myself or my team. And there's a place for that. And of course we want to help people get better and we certainly want to make ourselves better. But what I recognized really early on in my own career is that I lived in this place of self doubt and lack of confidence for far too long because I didn't spend the time to figure out and lean on the things that I was really good at. My journey is a little bit unique because I took it was going to be a gap year. It ended up being almost a gap five years where I worked for a nonprofit before going to university. And I led teams during that time. So 18 to 22, I was leading teams, trekking through the jungle in Southeast Asia and, like, doing really interesting things. And so when I started my career at 25 as a seller, I wasn't very good at selling out of the gate. It took me a while to build those muscles and learn about business and figure out how to be a trusted advisor. But I was really good at leading teams. I was great at creating culture and seeing people and making them feel safe and understood. And I focused so hardcore and so much on how to get better at sales really fast and all the things I wasn't good at, that I think I waited too long to recognize that I had a really natural path into management and leadership. So in reflecting on that, on myself, that's a lot of how I look at people and managers that I lead. How can I help them figure that out? Maybe a little bit sooner. What are some things that I can identify that they're naturally really good at? And to your point, we all have them. Doesn't matter if it's your top performer or, you know, your biggest challenge that's keeping you up at night. We all have something we bring to the table that makes us really good. Like, I think of a rep I managed a couple of years ago, and she was everything I look for in a rep. Like, just like an athlete, super competitive team player, delightful to be around. Like, literally the makeup of an amazing salesperson. But she really struggled early on. Like, she was just missing things and certain things weren't clicking. And we sat down and started figuring out it was just she was in a new industry, and it was taking some time to build that business acumen, muscle. And she was so stressed about that that she was literally, like, missing key things within a discovery, not knowing how to direct a conversation, struggling to think on her feet. And we took a step back and realized, like, hey, your superpower is people love you. You are so good at building relationships. So there's no quick fix for how do you learn everything about this industry? The quick fix is we're going to lean on the fact that people really, really like you and want to work with you. So if you need to ask the question two times or three times, then ask the question again. If you need to call someone back because you missed something, call them back. Like, she got so much grace throughout this process, and people just wanted to do business with her. She ended up, of course, being a superstar. Of course she learned the industry and got quicker at some of the things. But it's interesting she also got even better at the relational aspect that has served her to this day. So I think it's usually as simple as just figuring out those few little things that someone brings to the table and helping them focus there.

Alright, so you just opened up so many cans here that I'm ready to dive into. This is going to be great. So let's first let's talk about self doubt and confidence.

Right.

Because that is, that is like the Achilles heel or just holds back so many. Not even just salespeople, people in general. Right. Just all of us. Right. Of doing what we're capable of. You said you started with a lot of self doubt and you didn't have a lot of confidence. How did you build it? Because a lot of people when they get into that situation, they then just avoid it. They say, well, sales isn't for me or this isn't for me because I feel this way where you leaned into it and you said, okay, I'm going to fix it. So how did you get out of that place? Because I'm sure a lot of people listening right now can empathize with that word for word. That doubt and that fear and that, oh, that heartbeat, that stomach like turning when you have to pick up that phone. How did you work through that?

Well, first of all, it took me far too long. So I'll admit that front and center. But I think I did really early on. I identified there were some things about sales that I loved. I recognized what I wasn't good at, but I really enjoyed the process of getting to learn a ton about business. My first job out of college, we were in an open territory model so I could literally. And it was full funnel so I could source anything and sell to anyone, which meant that I worked a ton because there was no end to what you could do. And I sat up at night prospecting. But I found that there was aspects of that that I just loved because I was learning so much that was outside of my core skill set. And I felt like I was having an opportunity to really learn about business. And if you're not naturally curious and don't enjoy something about business, you're not going to be great at sales. Like it's just, that is what it is. And so for me, a lot of it came down to finding some aspects of the job that I really enjoyed. And when you're in those moments of like, I don't know what to do here, I don't feel good at this. I don't terrified to pick up the phone, whatever it is. I had to lean on those things that I did enjoy in the process and I did. I struggled a bit more with some of the. The cold calling never really scared me. But some of the process of selling, it just took me a little while to wrap my head around that, understand how to direct a process. But I did enjoy so many of the aspects of that prospecting and the top of the funnel piece. So I just did a ton of that. I knew that I was going to have to go through more sales cycles to really build that muscle and get smarter and better. But I found ways to focus on the things that I enjoyed in the midst of that. And I think that was key for me.

I love that. So then this goes to the next level. How do you bring that down to your team? Because the words you use, you said making people feel safe and secure, right? Even the rep that you mentioned, like feeling like she's safe enough to have that conversation with you. What are some of the things as a leader that you try to build into your team or into your managers where reps do feel safe and secure? Because if we walked down the street and talked to 100 salespeople right now and said, hey, do you feel safe and secure in your job right now? I bet you we don't crack the 50% majority there. So how do you build that into your teams?

Got an even more so now in this Covid world that we're in, how much insecurity and just lack of that is floating around. It's really scary in terms of building that into a team. I'll be the first to say that the remote management piece is new for me. I'm learning a ton. I think it changes the dynamic, makes it even more important, but it's harder and you have to do some things a little bit differently. But in terms I talk about psychological safety, we've all read the Google study of what that means and kind of how important that is. But it's just creating an environment where people feel like they're allowed to fail and celebrating failure like, we're all going to screw up, we're all going to make mistakes. There's going to be times when we don't operate at the best version of ourselves and giving people a safe place where they can admit those things, ask for help. I mean, in a remote world, sometimes it's as simple as just encouraging people to ask more questions. If you've got team slack channels in different places where people communicate or in a Team meeting or different environment. Hey, ask the team for help here. We're all getting stuck. Things are moving so quickly. We're expected to pivot literally every three weeks. It feels like there's something new we're supposed to have figured out as sellers or sales leaders. So ask the question. Figure out who else is struggling with this. Sometimes it's as cheesy as, like, we make everybody talk about one mistake that they made this week or one epic fail or something that went wrong. But you just have to create an environment where people recognize that literally, whether you're top of the charts or the bottom of the charts, we're all going to have weaknesses and failures, and that's okay. And the goal of a team is to drive that forward and figure out how to offset for one another's weaknesses or failures.

I love that. And I think that is one of the harder parts I've noticed so far. Also now having a fully remote team is in the office. When someone crashed and burned, we were there. So not only did you know the crash and burn happened, but also you could laugh about it, you could shake it off. Right. Sharing those epic failures was actually easier. It has been harder. Right now, you just get crushed on a cold call. You're just sitting there by yourself. There's no one around to really share that with. So I like that you're being proactive there. Now, I want to call out a word that you used a little bit earlier, which is different than what most people say, even myself. You said, create a culture. Most people say, build a culture. You build a culture. You said, create how to create a culture. And I like that nuance in word. I'm picky with words. And I think that's very different because building implies you have the tools. Creation is. You gotta go get everything and put it together. So as a leader, how do you create the culture that you want? What are the things that you think about on a regular basis or the things that you do to actually create that culture?

That's an interesting nuance that you pointed out. I don't think I've ever thought of it that way. But as you were describing it, I do think that I look at it slightly different because building also kind of says that you've got a foundation that you have to stick with, and then you're going to make it better, you're going to improve or make tweaks. And I think create gives us the sense of like, the world is our oyster, like, we can build the teams that we want and we can create in individuals and environments the dynamics that we want to see. So I don't know that I've ever thought of it quite like that, but I really like the nuance that you called out. Yeah. One thing we haven't talked about much, I think that is super important for me and my leadership style and what I hope to foster in teams definitely ties into that concept of psychological safety. But it's also being really, really authentic in who you are as a leader and instilling that in your people as well. I mean, sometimes it's as simple as we talked about helping people find their superpowers. We all also have a lot of gaps and things that we're not great at. As a leader, I know a lot of things about myself. I get bored easily. I multitask too much. I struggle to follow through with projects at times because I get bored easily. I naturally talk really fast, so it's hard for me to slow down and. And give people space at times. So sometimes it's as simple. I think this has to happen at a one on one level, but building that sense of trust where, you know, maybe I sit down with my fabulous, you know, most introverted sales rep that I adore, but who's very, very different than me, and I have a conversation that says, hey, I think you're phenomenal. You know, you and I communicate naturally, really differently. So there's times when the way that I talk or the types of questions I ask may make you feel run over at times because I like to move fast and you need time to process. So what I would appreciate and love if you could do is help me see that it's something I'm aware of, it's something I'm working on getting better at. But if you notice that and it makes you feel a certain way, if you could just let me know, like, I'm doing everything I can to try to improve, but I want to honor the way that you communicate and what you need from me as a leader. Little things like that, that acknowledge, hey, I've got stuff I'm working on. I'm aware of it to some degree, but if you could help me be more aware, it's going to make me better and it's going to make me manage you in a way that makes more sense and empowers you. Those types of things, I think are key in creating that culture of authenticity, open communication, the type of trust we're really trying to build.

That was so good. And I hope everyone listening really picks up on what just Happened. There is oftentimes as leaders, we try to make people into us. This is how I did it. This is how I sell. This is how I communicate. We try to turn them into us. It's one of the mistakes I made very early on in my leadership. But what she's doing is the opposite. This is me. This is what I see in you. I'm not trying to turn you into a fast talking, snappy person because that's me. I'm gonna let you be you and go through it. Something I suggest leaders do. I have mine. I have working with KD Manifesto. It's like five pages and it describes how I communicate, how I look at data, how I think about things, right? So even things as simple as especially going to a new company, my thinking face looks angry. So like, obviously it's audio right now. But my thinking face is like a scrunched, right? Like I sit and I scrunch my face as I think. If you don't know me, that can come across as very intimidating or that can come across as, oh, he's disagreeing with what I'm saying. Whereas if I get that in front of me and say, this is how I think, I'm okay with silence. If I'm not talking, it's okay. It just means I'm thinking. So I write all that out. Ashley, I'll share it with you after this episode. You can see what it looks like. It's a really fun.

I literally just jotted that down. I'm like, I need a manifesto. It's perfect.

I'll share mine with you and you can read through it because it does. It breaks that all down. It's also just a fun exercise to go through to identify strengths and weaknesses, which a lot of leaders don't. All we like to identify are our strengths. We don't like to identify our weaknesses. Now, something else you've talked about a lot is frontline leadership. That there's not a lot of investment in it. There's so much investment. Well, we'll call it so much investment in rep development. But even that's not that much. Then you become a manager and there's almost no development. And then you become a director and there's like no development. And then you become a vp. Do you know if you go on Amazon right now, by the way, and type in VP of sales and books, not one book shows up on how to be a vp. There's nothing out there. So I want to go through the different layers here. One, what you do to develop Your frontline managers. But then two, what are the things you developed basically in yourself as you moved up the chain because it disappears. I haven't had a development conversation on how to be a great VP of sales from any company I've worked for. I've got mentors, but no company has developed me that way. So how do you develop your managers, but then also how do you develop yourself?

Yeah, there's probably a couple things that I would highlight. I mean one, the component we've already talked about in terms of how to run a one on one or sit and have a trust building conversation, acknowledging strengths, weaknesses, that probably is the first thing that I focus on with new leaders. It's the piece that feels the most outside of our comfort zone. I think when we make that transition into, for most people, moving from an individual contributor into their first sales leadership role or even a team lead role, they're used to winning and being really good at what they do. And to your point, their knee jerk immediate reaction is how can I make the rest of the team more like me so they can sell more deals? And that's not how it works in management, but it's the most easy thing to lean into. And so that first trust building conversation, figuring out what are the nuances with the two people you're leading or the five people you're leading, or the eight people you're leading so we can start to understand, not the old school like stack ring system, but hey, each of these individuals, what do they bring to the table? How can we help pull those things out? And for new leaders, you got to kind of do some of that with them, literally in one on one conversation, sitting and creating those building blocks to teach them how to see some of those strengths and even asking some of the questions, okay, what are some things you think we could do together to highlight that, to pull that out? You've got someone really struggling with confidence. What are some things that you've done in the past or you've seen really work for others that has helped build confidence? So usually they can figure that stuff out, but it's just asking some of the questions. I think also for new leaders or really frontline leaders at any stage in their career, helping them understand what the job actually is. For most of us, there's three or four things that we've got to be great at and three to four core responsibilities. I mean for me, it's like a pretty clear playbook in terms of making my people the best version of themselves, delivering the revenue, forecasting accurately and then building my company and myself from a brand perspective, those four things make up most of what I do in some capacity. So helping leaders understand what are the things that you actually have to do every single day to be able to walk away and feel like, okay, I delivered, I did the best that I could today, and I think that rings true at all stages of our career. So it's something that I've honed in on more as I've led larger teams and kind of advanced in my career is, okay, what are those core things? And how do I make sure as the team grows that I'm actually doing them really consistently? I think that ties in probably to the second piece of your question around how I've developed myself. Although I could go on a really long monologue on that one. So maybe I'll pause because you probably have more questions on this.

I got a few questions there, but actually it's not even a question. I want you to say your first bullet point again because I think leaders forget this. You said the core four things that make me a great leader that I focus on. You list out the four. Hopefully the order stays the same. What was the first one?

Making my people the absolute best versions of themselves.

We could stop the episode right there. And if every leader actually thought that way, all the other things start to fall into place. This is something I drill my managers on. You could bump into my managers at 2am on a Saturday morning. They might be five Red Bull vodkas deep. And you ask them what their job is, they would be able to tell you, it's to make my people better.

Right?

It's not to hit revenue, it's not to hit for it's to. The first job is to make their people better. Then the other things fall into place. So I hope everyone caught that. That is huge. That that is her foundational. I don't want to call it a core value, but that's the first thing because that's the things that fall into everything else. Now, this actually doesn't make me back up. I. I wrote this question down three times now because I keep wanting to ask it from something that you said earlier. Great seller, great manager in the industry, oftentimes it's the top sellers that become managers, even though oftentimes maybe they shouldn't. How do you identify a good leader who maybe isn't the best salesperson, but then also how do you help get that person into leadership? Because sales has this really stupid mentality of like, you have to be better at selling to lead Me, which it's a very unique. It's very unique to sales, right? You brought up athletes before like Michael Jordan wasn't like, oh, Phil Jackson, you're not a better basketball player than me, so I'm not going to listen to you. But in sales it's like, did you make Prez club five times? Because I made Prez club five times and you didn't make Prez club five times. You can't be my manager, right? So now I'm rambling there a second. So there's two parts of this one. How do you potentially develop a leader, right, who maybe isn't the top of the board, but you can tell they're a great leader. But then also how do you handle that dynamic potentially of like moving someone into a leadership position even though they weren't the best salesperson?

Well, this one's near and dear to my heart because like I mentioned, I wasn't the top salesperson. I was never the bottom of the charts, but I wasn't number one or number two out of, you know, a hundred reps. And so that transition is really challenging. And like I mentioned, I wish I had recognized sooner and had someone feeding into me, hey, some of the stuff you do naturally within a team environment is really unique. Let's do more of that. And I think that's what it comes down to. I think there's two things that really have to happen when we think of how do we get right folks into management. It's also helping reps figure out what do they want to do. Because sometimes there's this expectation that to move up in my career, I naturally need to manage people. And that's absolutely not true. There's some of the most successful salespeople I know that are making a ton of money and doing really well are these kick ass enterprise sellers. And so there's two very different career paths. And I think our job, especially if we're managing folks that are relatively early in their career, is to help them figure out one, some ways to explore to figure out what they really enjoy, but then to help career path them in one direction or another. And I usually make it as simple. Like for someone that works for me, it's hey, like what gets you ultra jazzed? Like is it closing your own deal and bringing in that business or is it if you help teach someone something else, Someone, someone else something that they didn't know and then they crushed it in a way that maybe you didn't even think of, like you can pretty early on figure out there's people that are wired just a little bit differently where they get so amped about seeing other people succeed. Doesn't mean they're not ultra competitive and they still want to win, but they really enjoy seeing people around them succeed kind of at a different level. So one, it's helping them figure that out and then if they identify early on or whatever point, hey, I know I want to lead teams. I know I want to manage. My first piece of advice always is do the job that you want. Same advice I give SDRs. You want to be an account executive, start doing the job as much as you can get your hands on before it's your job. It's the same. If you want to be leading teams or managing people, look for ways that there might be gaps or opportunities in your team. Every leader out there right now is struggling with something. I mean, this Covid dynamic move into remote. It's been a challenge for all of us. So I guarantee that if you're an individual contributor, if you take five minutes to think about the job that your boss is doing, there's things that you could be massively helpful. There's things that you could bring to the table that he or she is definitely looking for. So try to find those opportunities to put up your hand and say, hey, love to lead this in our next team meeting. Or I noticed that this was missing last time. Can I follow up here? How can I help you with this? Just little bits of proactivity go a long way and naturally start positioning you to the rest of the team as someone that's leading, that's taking ownership. And I think that goes to your next point of what if you do have this dynamic where you promote someone who wasn't number one or wasn't better necessarily from a numbers perspective than the people around them. If you've done the right things in kind of to set the stage of positioning them as a leader, then that dynamic, I think, is a lot easier than if it's just out of nowhere some random person gets promoted and at the team's like, what? This is kind of unexpected. Yeah.

Now that last part there too. It should never be unexpected, right? Like if you're a rep who wants to be a manager or a leader, however it is, it should be actually pretty anti climactic when it happens happens. It's like, all right, hey, everyone, like, we moved Katie into management. The response of the team should be, yeah, like that's kind of what she's been doing for a while now. Anyway, saw this coming, right And I think it goes into one, the rep doing their part to do the things ahead of time, but also, as you mentioned, the leader putting them in a position where they can start to be seen that way. And it shifts a little bit there because I think that's so important. One of the questions that I asked, anyone that comes to me says they want to be in management, ask them four questions. Say, one, are you ready to put your income in someone else's hands? Are you ready to put your income in someone else's hands and potentially make less than you were making before? Two, are you willing to have me be mad at you because of what your team is doing?

Oh, such a good point.

Okay. Are you willing to sit like, as salespeople, we love to take ownership, but as a manager, it doesn't always work that way. It's like, are you ready for me to be mad at you because of what your team is doing? Three, are you willing to have your success no longer tied directly to your work ethic? You can't work your team to success. You can't just put in more hours as a manager and get better results, right? And then that, that fourth one, it's like, are you ready to make less money for other people's success? And a lot of times those four questions, I can watch people's faces, right? And they, their faces change, they go, oh. I was like, okay, so you may not want to be a manager, you might still want to be a leader, but a manager, those are the buckets that you're going to have to check. And it catches people off guard sometimes. Now, full circle, back your development. So you made that transition, you were a good seller to a great leader to now VP your leading leaders. What are some of the things you've done to develop yourself into the leader you are today?

So one thing, and you made a comment about we invest way too little in leaders as they move up the chain. One thing that I think demand based, my company has done a really good job at is investing in some external coaches. So we have an executive coach for our executive team, which has been massive for me. I've toyed with the idea of hiring my own executive coach many times and just never pulled the trigger and done it. So having someone aligned to me that is outside of my day to day, it's not my boss, it's not someone that I work for or with, has been really empowering. It gives me the opportunity to ask really specific questions and focus a bit differently. Even something as simple as I want to run more effective one on ones like I don't get feedback on how I do that. Like in our job we don't get a ton of feedback as much as we ask want it. And so being able to have someone external really kind of peel back the layers, ask some questions. How are you doing this now? Have you thought about this? Give me a story. Tell me an example of how you've done this. That's been really impactful for me and I wish I had done it sooner in my career. I think the other thing that gets more and more important as you move up in your career is cultivating just a broader network outside of your company and your team. You made a comment earlier about your boss. You've got mentors, but your boss isn't necessarily the one that's leaning into personal development. I don't think at our level that's necessarily the expectation. But I desperately need coaching and leadership and mentorship. And part of that's just getting exposure to how other people are doing things and what's going on in the industry and some of the challenges that other folks in my role are facing. So find ways to get plugged into communities or networks. For me, revenue collective has been massive. I've met one of my actual friends through it, which is amazing, but I've also met some incredibly talented people that I'm able to learn from. Some of it's direct one on one conversation, some of it's more passive by access to Slack and some other really great, you know, tools. But those types of things I think it gets. It'd be really easy even now as we're fully remote, to get a bit lazy and kind of just focus on doing the role, getting through this season as opposed to what are all the things that I can do to make the most and really maximize this season. So that's kind of how I've been thinking about it.

No, I think that's great. I think the best leaders that I've spoken with and learned from are the ones that are open to learning. Actually, open learning is not even the right word. It's seeking it out. It's. You know, everyone loves to say they're open to learning, but if I'm just sitting on the one is sitting on the couch. Like learning is not just gonna walk through the door and show up like you have to go in and get it. So now we're gonna make a small shift here because we've been talking a lot about leadership and development. I want to get into some tactical sales things Here a little bit too. Right. So as you've been leading these teams, which is always one of my favorite parts, is you get to see a lot of what's happening.

Right.

Like when you're the seller, you have your results and you have what you do, but when you're leading teams, you get to see, like, what the patterns are. So we're gonna go through some closing tips and some prospecting tips.

Right.

So as you work with closers, is your team full cycle or do you have split?

No, it's weird. We have SDRs that support, but we do 25% of our own pipeline, so.

Okay, perfect. And you said when you started, you were full cycle as well. Right. Like, you just go out and get it. So let's start with the prospecting side first. What are the pieces of advice that you give new reps or veteran reps to have better success while prospecting? Because pipeline is kind of everything. No company is drowned in pipeline. Right? We starve. We don't drown. So, like, how do you help your teams generate more pipeline? Let's start there.

Well, first, when we talk about prospecting, it's do it and do it all the time. And this is absolutely critical. Whether you are an account executive closer, full cycle, just an sdr, whatever phase, you have to constantly be looking at the business through the lens of a hunter and someone that is sourcing opportunity and looking for opportunity that doesn't yet exist. So I talk a ton about just intellectual curiosity and being genuinely curious about business. Like, if I'm not on a zoom call or recording a podcast, I've got CNBC on next to me and I'm reading news and just things that are happening that are really interesting all the time. So even at the VP level, I prospect all the time. Ask my team consistently. I'm popping them some, hey, this company got funding. Do we have we talked to them. Hey, this really cool thing happened. So I think you have to think like that. Especially if you are in an account executive role and you own a territory, you got to think like the CEO of that territory doesn't matter if you've got 10 accounts or if you've got a Geo, there's something that you can own and you can think like a business owner. And the best prospectors or hunters, the best salespeople, they think like they own that business and they're doing the short term and the long term things to really cultivate that business. And of course, all the things we talk about in terms of being super creative, be authentic, try to automate your way into success. There's no massive amount of volume that's going to get you the fix. Or a pipeline perspective. I don't know. I don't believe in most of that stuff. There's some process things that we can do to make our lives a little easier, but at the end of the day, we're trying to connect with human beings and create enough value that they give us time and talk to us. It's pretty simple.

Yeah. I mean, I joke with my team. I've said it on some webinars, too. Is like, if it was as easy as sending a templated email, I wouldn't need salespeople. Like, I just. If I could just send a templated email and wait for the positive responses to come back, I wouldn't need salespeople. I just loaded all. I'd load up all my. I'd load my tam up into Marketo and go. I was like this. This is where the creativity comes in. This is where you get to flex that muscle and bring personality into it. You have to. Templates are not going to give you success. There's frameworks to follow, but not templates. That's not going to give you the best results. Now let's flip it then to closing. Right. So, all right, I've done a good job. I've worked my territory properly. I got their attention. I got them into the sales process now and funnel. What are the things that you encourage your reps to do to close business either more or close business faster?

So it's interesting because I think one mistake that we make as leaders at times is we think of closing as if it's like this separate motion or the separate thing that happens. Back in the day, I worked at a company and we would talk about how many closing calls that we have on the calendar. It was like as if this negotiation and closing process was somehow removed from the rest of the sales cycle. And I understand there's lots of different types of sales motion. Some are very transactional and quick. Some are much longer and more complex. But at least for the business that I'm in, closing is in no way removed from everything else that we're doing throughout the entire process. The best closers are the ones that are best at discovery. And then they're able to do discovery throughout the entire sales process, whether it's two meetings or 22 meetings. They're constantly figuring out what makes this person tick, what's the company trying to accomplish, and they're finding ways to tie that product or that service back to those end business goals. Closing should feel like the culmination of both people winning, like we're both getting what we want here. One of my reps got a deal literally late last night, and it had been the most laborious legal process we've been through in a while. Our deals are usually pretty simple once we get to the yes. This has been like, almost three months of back and forth and some really silly stuff that was outside of our control and outside of our buyer's control. So literally getting that contract signed. My rep was winning, and the buyer was winning. They were so stoked. Yes. We got this across the finish line because it mattered to both of them. And to me, that's what the best closers are able to do, is tie the entire motion back to making that person that you're selling to feel like this is a win for them.

I love that. I'll tell a real quick, funny legal story. So this is back when I was in my selling days as well. Long contract cycles. Get the yeses from everybody. Send over the contract. Right? Legal red lines the hell out of it. Right? All the red lines. I get it back. I accept every change that they made, and I send it back. I say, cool, all this looks good. Go for it. They reviewed it. They redlined their own agreement. So they sent me another contract back that they redlined. It was the one they had sent me. I had just accepted everything. They redlined their own contract. And I was like, are y' all just sitting there with, like, a thesaurus and just, like, changing words to change words? Like, this was your contract. How are you redlining your own stuff? So if we got any legal listeners, just stop it with that nonsense, all right? It's not your job to make this harder. It's okay. Like, we're all good. So. All right. From there, the last big topic I wanted to touch on before we kind of wrap things up is I know women in sales is very. A very passionate. I don't know, even the right word here. Passionate projects. Totally wrong word. Don't kill me for that. But you know what I'm saying, It means a lot to you. Right? And this is something that means a lot to me as well. It's something I focus a lot on. I'm very intentional about trying to bring more women into my teams and into leaderships, and it's something that gets talked about, and it's definitely being talked about more. But what I wanted to hear from you is more of what are the actual tactics companies can do or leaders can do to actually create this change, Right? Because we can talk about it all we want, but it's like if no one goes back and does something differently, nothing changes, right? Nothing changes if nothing changes. So what do leaders or companies need to change in order to get more women into sales and get more women into sales? Leadership. And not even sales leadership, just leadership positions, executive positions. Like, what are some of the changes you think need to happen?

Part of it does depend on where you're starting from. In a lot of SaaS and tech sales environments, it's still very much a bro factory and lots of dudes, a lot of dudes that look the same. If that's your starting point, then the first thing you can do is stop hiring everyone's friends. You have to get outside of your immediate network. We tend to naturally, we hire within our network and we naturally hire people that look like us, that have some of our strengths. Even as a leader, I naturally pick up on things that people are good at that reflect what I'm good at as opposed to naturally looking for things that are different, which is super important. So depending on where you're starting from, look outside of your network. Get out there in real life in different ways. If you don't have people complain all the time about not having a pipeline, I don't have the right, you know, enough diversity in our applicant pool. Well, then go out and find the people. There are so many communities that are out there. Get active. Show up on a Thursday night sales call. You know, there's so many different things that you can do these days to tap into real talent and find people that are outside of your network that don't look like you, that don't come from where you come from. So I think that's super, super important. I also think you've got it. Assuming that your company has women in leadership or at an executive level, make sure you're showcasing them, make sure that they're on the website, make sure that you've got them producing content. Get them on LinkedIn. One of the first pieces of advice I give to either, you know, gals that are relatively new in their sales career or folks that are wanting to get into sales that are females is figure out if there are women that are leading there. If there aren't, run like, do not work there if there aren't some women that are leading teams, because that tells you that there's a dynamic where women aren't getting promoted or they're not finding ways to create diversity. And I think the topic is much broader than just getting more women into sales and into leadership. But the women lane is certainly where I've played and have the most experience. So showcase the gals if you've got them on your team and get outside of your networks and find people. Those would probably be the most. Two tactical things, I would say.

I'll share a story because this is recent. This is literally within the last 24 hours. And I was excited to talk to you about this because I actually reached out to a few people privately and asked about this. So I just made a post yesterday, right? We finished a series C, and I'm looking for SDRs and SDR managers. So I make this post. God knows how many views and comments it has right now, but I have gotten 25 counted this morning. 25 direct messages about the SDR manager position. 22 of them are men, two are women.

Wow.

And I sat back. I've messaged. I actually have quite a few women that I mentor in sales directly that, like, you know, I pay. I was like, what am I missing here? Because I do care about this and I'm intentional with my language and I make sure it's not bro tastic and, oh, you gotta have 10 years experience all this. I'm intentional with it.

Why?

And this is probably bad question. So I'm making you answer for all women in the world. But where? Either what can I do differently or what encouragement can you give to women to reach out, right? To be like, when you see something like that, to reach out and say, like, hey, like, I am interested, because I am. I'm doing direct outreach now to go try and, you know, drum things up. But that was such a 25, 22 guys, like 23 and only two women. Why do you think that occurs? Or is that not a fair question to ask?

Oh, it's 1000% a fair question to ask because we focus, and it's rightfully so, we need to focus on what? Us as hiring leaders, managers. Leaders, executives. What do we have to do to fix the problem and to create more diversity. But when we think of women and getting more women into leadership positions specifically, we also have to be willing to step up to the plate and take the chance, make the dare Risk. Take a risk for a job that maybe we're not fully qualified for or we don't think we have all of the skill set. I mean, there's tons of research. McKenzie did a massive study a few years back. Women literally will not apply for a job until they feel like they have 105% of what that company is looking for. Whereas men, again, massive generalization will put up their hand when they've got 50% of the qualification. And so that follows us. And there's lots of psychological reasons in the way that our culture raises little girls compared to little boys and lots of things that you can dig into there in terms of how we're wired to think. But we have to take ownership for that and be willing to step outside and take those risks, take those chances. And to your point, one, proactively get out there making sure we're connecting with the right people. But when we see something that is interesting, be willing to throw our hat in the ring and say, like, hey, I'm your girl. I got this.

Yeah, like, it was just something I was like, man, because I was really intentional with the language, right? You know, open to coaching, right? Bringing the best out of people. Nothing about years experience, nothing about industry, nothing about it. And I was just like, damn it. Like, that makes it hard because then you have all these applicants and you have to work through them and do things. And I was like, I just wish there had been more. But to your point, the key that I think with all this, any diversity in sales, whether that's women, whether it's minorities, whether it's sexual orientation, it's being intentional. It's going. Because I've been getting a lot of those messages like, how do we get more blacks into sales? I'm making this post and I'm going to say, I want a black leader. I'm like, okay, pause here real quick. Have you even tried, like, have you reached out to the black business unions? Have you reached out to the black and tech group? Have you reached out to the women in tech group? Like, have you actually reached out to do it? Are you waiting back passively, right? This is full circle back to open to learning. Just because you're open to diversity doesn't matter. You gotta go get it. And I hope people understand that message here on both sides. Right? Go get it. But also be willing to put yourself out there, right? To be got, so to speak.

And it's interesting you made the comment about your. It's a LinkedIn post. And one thing, I've been very purposeful the last six months to be more present and start to build a brand on LinkedIn, which I hadn't done previously. And one of the reasons that that became important to me as, as I started spending more time, I didn't see very many women creating content, at least not sales leaders. So different genres in different spaces, but there were just very few thought leaders that were producing and really doing a lot of connection. It's been interesting over the last six months that's there's some amazing people that I've met, connected with, learned from, but it still tends to skew. I look at even my own content. Unless I post specifically about women in leadership or women in sales. A majority of the interaction that I have, and I'm assuming even the views that I get, tend to be a lot of very male heavy. So there's some purposeful pieces that we have to do, even at the very foundational levels, I think, and it's important.

And this is why I was so excited to have you on, is to have that voice. But people need to see it. Like a few of the women that I mentor, I've encouraged them for almost a year now to get more active with their branding, like, their posting. All of them said the exact same thing. When I mentioned it, it was like, well, I'm just gonna let my results speak for themselves. All of it, the exact same type of response of like, well, you know, I don't want to put it all out there. I'm just gonna let my results speak. And I was like, you know, you kind of still got to put it out there because no one can come in and see those results, right? But you inspire someone else, right? And that's what's so, so important. And this has been inspiring. So we're going to wrap on this. I got two questions left for you. The first one, the big three, right? So we've been going now for 50 minutes, right? And people are going to get to the end of this and go, whoa, what just happened? She dropped so much on us. If there were three things that you would want them to remember from this episode, three tactical things, what would those three things be that you'd want people to walk with?

Trying to figure out how to make it really short. First. One, get good at finding people's strengths, starting with yourself, and then become maniacal at finding other people's and help bring those out. Two, be authentic. Whether you are a seller or a leader, people want to see who you are. They want to buy from you. They want to work for you. They want to trust you. So be authentic. And for the leaders, take ownership of making your teams and your companies more inclusive and more diverse.

I love it. I love it. And then the final question, right? The name of this podcast is Live Better Sell Better. Right? Focusing on the person. I have this weird Idea, Right. That if we live our best selves, if we are better as people, the sales improve as well. What would be your live, better advice to everyone listening? Right, like, how to get more out of life, more fulfillment from themselves, more joy.

Right.

What would be your live, better parting advice for everyone listening?

We could definitely do a separate 50 minutes on this one.

For sure. We could.

The first thing that comes to mind is have more fun. I think that we, especially those of us that are wired to be ultra competitive and intense and very career oriented, we tend to forget that when we're not curing cancer, we're selling software, we're mentoring people, like we're connecting with human beings. And I mean, the job that I get to do all day, every day is pretty amazing. And I need to find ways to enjoy that and revel in that versus being kind of attached to the stress and the pressure of it. So I think that would be my live, better advice. Have more fun.

How do you have fun?

So it's been very different with COVID Normally I have fun. I travel a ton. I've been to 52 countries, so my husband and I tend to travel a lot, like every other weekend almost. So that has changed. We also tend to eat out and drink out a lot and have a really great network in both Atlanta and New York. So not being around very many people and not leaving the house as much has definitely crimped our style. So right now it's been very, very business oriented. I've been reading a ton, building a lot of cool connections professionally that are kind of morphing into friends, friendships and doing a lot more stuff virtually and trying to find creative ways to enjoy that. So ask me again in six months and I hope the answer will get back to normal.

Ain't that the truth? Six months, please. Back to normal. But Katie, this was amazing. You have absolutely a new fan. And I have so much respect for what you do and how you do it, which is, I think, so important. How you think through things and how you teach people and how you care for yourself and others. So thank you so much for your time. Where can people find more of you? Where can they get more of you? Like, how do they stay in touch with you?

Sure. LinkedIn is definitely the focus. I'm Katie Ivey and it's Katie with a C. So I'm pretty easy to find on LinkedIn. There we go.

Katie. Ivy. Katie with a C. Thank you so much for your time today and your advice and your expertise. We'll have you back again. Because this isn't gonna be one and done. We got so much more we can start dive into. But thank you for your time. Be safe out there. We'll be in touch.

Thanks so much, Katie.

All right.