114: Taking Charge of Your Sales Career With Sydney Sloan

Thank you to our partners, SalesLoft, LeadIQ, and Costello for helping us put this one on. Find all our upcoming events at jbarrows.com slash events. Good afternoon, everybody. This is John Barrows. Make it happen Monday. And I hope you all had a great weekend. I am excited for our guest today. She's actually my new favorite dance partner, Sydney Sloan over at SalesLoft. How's it going? It's going great. Yeah, what was that? It was Dreamforce last year, right? It was. You got the moves, John. You got the moves. Only with old school hip-hop and stuff like that. As soon as it turned into the new school stuff, you noticed I was like, all right, I'm out of here. You put Biggie or Tupac or anything like that on and I'm all in.

So anyways, Sydney, for those of my audience that don't know you, they all should because I talk a lot about you and I talk a lot about SalesLoft. But could you just give everybody a little bit of background, like what's your role right now at SalesLoft and kind of where you're coming from? Yeah, sure. So I'm currently leading the marketing team as a CMO at SalesLoft. I've been here for just over a year. Boy, how time flies when you're having fun. And it's been great just to see the company evolve in that time and the industry and the role that we get to play in that, along with you, John, and you're a great partner and a great inspiration for so many folks. And prior to that, I definitely had a lot of roles in marketing.

I think I've worn all hats by now. And I am one of those geeks. I like to, you know, we have sales nerds and I definitely wear the marketing geek t-shirt in the sales nerd world. And, you know, just love being able to understand customer problems and craft the stories that allow us to share and inspire people. And then my other area is kind of around building community. So the short form of kind of my background and how I got here, long time at Adobe and in product marketing and creating market opportunities and shaping kind of what digital transformation was back in the early days. And then I got to serve customers in the Jive community. So I ran community and customer marketing at Jive and kind of hopefully, you know, on the pioneering side, I would say, of customer experience.

And just thinking holistically outside in about customers, especially in SaaS, as we know, you have to work just as hard to keep that, to onboard, adopt, grow, retain, is as equal to the front end of the funnel in terms of the buying experience and bringing those customers on board. And so really starting to understand the dynamic between those two worlds. And then most recently was a CMO at an open source document management company called Alfresco. So it's been awesome. Yeah. So I think we could, you know, I mean, we could take this conversation a million different directions because of sales and marketing alignment, how things are evolving, the customer experience. But, you know, I think what's near and dear to both of our hearts these days from a development standpoint is career development, right?

For the people that we work with and for a lot of people getting into sales, specifically in marketing, because my actual background is in marketing. And I fell into sales because I didn't want to do that out of college. Like I didn't really, it didn't feel right for me. So I just wanted to be out and, you know, and just, you know, making calls and that type of thing. But it, but it, it was a, it wasn't a purposeful thing. I, you know, I, I kind of, like I said, I didn't know what I didn't know. And so I just stumbled around. Now I was very fortunate that a lot of things happened in my career to kind of keep me moving in the right direction. And you couple, you know, I, I personally don't believe in luck.

I believe you make your own luck. And, and so I think that's what's happened with me over my career is because of my work ethic and my, you know, my motor, if you will, things have tended to pan out in the right direction. But, you know, you talk a lot about, um, taking, taking control over your career. Yeah. So can I ask you, like, when was it like throughout your, your history, your, your career history, if you will, when did you really start taking control of your career? Like, when did you consciously say, I, I, I got this right. Cause, cause I don't think some people that happens early on, you know what I mean? Like even before college, like I want to be a doctor period. Like, and I'm going to school for a doctor, most people in sales and marketing don't have that.

I know exactly what I want to be when I grow up type of mentality. So when did it strike you that this is, I'm taking control now? Yeah. Yeah. I was a pretty driven and in achievement oriented and competitive, uh, youngster, uh, throughout my like high school and college years. And, and, and it, where there was a definitive moment, I I'm actually doing what I intended to do when I set my, my college intention. And I know a lot of that doesn't happen for a lot of people. And my, my niece and nephews are going into college right now and, and, you know, it's just seeing how they're kind of discovering and that's okay. But I went to school for international business at university of Southern California.

And that's exactly what I'm doing. And it was the last year. So I, I put myself through school, um, and had all those great loans coming out. But, um, I think that's important too. Um, but I was, I was working 20 hours a week throughout college and, um, and had, was working at our, um, the donors department where there was actually a lot of outbound cold calling, um, looking for, for, um, donations. And then, um, we would host different events. And so I found my passion for events at 19, 20 years old and my senior year of college, I was lucky enough to get into the entrepreneur program at SC, which is an amazing program. And I wrote my business plan on an event planning company. And I use that as an opportunity to go out and interview the best event planners in Los Angeles and got to build relationships with them.

Um, and that translated into two internships and ultimately my first job at the special event, which was a magazine that was for people in the special events industry. So I was definitely straight into my career of what I was passionate about and doing by the age of 20, 21. I was like a, uh, uh, I had a student membership for meeting planners international. And, you know, I, I, I built that network, um, as a young person. And I think one of the kind of lessons in there is that never be afraid to ask people for advice. I was writing a business plan and I was getting all these great lessons from people who had been there and done that. And that formed the relationship that I was able to leverage for years to come.

And, you know, I, I think that's a great lesson for, for folks early on in their career. Um, if you don't know, ask, learn, um, and then once you find that path, you know, develop those relationships that can, can help you grow. So I agree. And I think, but so here's a challenge, right? Cause I think, you know, when I was coming out, um, of universities and such, and, you know, LinkedIn was just really just starting to get going in the early two thousands, that type of thing. And so to reach out to somebody and say, Hey, um, can I have effectively an informational interview? Or, I mean, that was, that was quite easy to do. I mean, I, I did something very similar to you before LinkedIn, even any time I saw somebody who I thought was successful, right.

Who I admired, if you will. And it didn't matter what industry, it didn't matter where they were in their careers. Whoever I felt was, I felt was, you know, I admired. I would ask them to grab lunch and say, Hey, you know, I was very structured too. I had like a, here's 10 questions I have for you just to try to get their insights. But now I feel like it's, it's almost a little, it's almost a little bit overblown with the informational interview and that type of stuff, because so many people have unfortunately used it as a sales tactic, right? To, to, Oh, you know, Sydney, I just want to pick your brain about where you are in your career. And then I'll try and some try to flip it. So what are some of the pieces of, and this also kind of leads to mentors, right?

Mentors versus sponsors and that type of thing. So how would you suggest a kid coming out, cause I couldn't agree with you more, go find people that you admire and, and try to emulate or at least understand their story. So you can see yourself. Can I see myself doing that type of thing? How do you recommend kids reach out like to, to, to somebody earlier in their career so they can really start to figure that out, whether it's in college or right out of school? Yeah. Yeah. Well, I think I probably have 10 to 12 years on you because LinkedIn didn't exist. I'm not sure the internet was around when I graduated, but, but we did have email. Yeah, I think I did. I think we didn't have cell phones back then.

Um, but I, I think it still comes down to the same principles. I mean, please don't ever use mentoring as a tactic to get into, you know, a sales, that's just, that's just wrong and not good, you know, uh, mojo. But, um, my, my, you know, start asking around and depending on who, you know, in your network or your parents, it's, I mean, I was talking to this kid the other day and they're like, oh, I don't want to use my parents' network. And I'm like, why not? Like everybody else is doing it. I mean, I admire you wanting to stand on your own, but do it after you get the connection, kid. Um, and, and so, you know, that like looking for people, I mean, the people that are putting themselves out there that are giving advice that, you know, you can listen to podcasts.

You can go do that first. And so when I get, and I just mentored a guy yesterday from a customer of ours that I, you know, he just asked for 30 minutes and he was prepared, but that's what I asked. I'm like, go do your homework first. Go listen to a couple of my pod. You know, we do this, right? Listen to a couple of podcasts, see what it is about me that is draws that connection to you, that there's value in what I have that can help you. And I believe in paying it forward. So many people did it for me in my life. And I can share that in terms of kind of my own career, but, um, you know, I'm willing to take that half hour, but be prepared, use the time wisely. And for instance, that mess, that meeting I had yesterday with this gentleman from Freshworks, um, you know, I said, okay, I'll give you three more, I'll give you three more half hours over the next year.

You have to choose how you want to use it. And so write me back, tell me what your goals are, what you want to learn as he's transitioning and wanting to become in marketing. And so I think you have to be, it's not just about, you know, the connection, but being prepared, purposeful, and then following through. So it lets the person that spent the time with you know that it was valued and that you're doing something with it. And they'll more likely take that second call a year from now, two years from now, um, when you need it again. And that's why I think like the, the takeaway for me on that is definitely be specific with what you're asking for from somebody like you and me, because what I, I, I do the same thing with you.

I love mentoring and I'll send my calendar out to anybody who wants to, and if I have time, I'll chat with you. But what drives me absolutely crazy is when reps say, well, John, why don't you give me a little background on how you got to where in your career, where you are in your career today? It's like, you could have done all that research on LinkedIn. You know what I mean? Like, like, Hey John, you know, I see you worked at Xerox and I noticed a lot of executives have copier sales in their background. Like, how did that impact your career early? You know, that's the type of conversation that we want to have because it's easy for us to, to have that conversation. Cause I can give you very specific concrete.

Yeah. Yeah. I can give you one, I'll give you one more and then we can go into kind of the, the, the, the layers of, of, of life as we progress through. And as I've progressed through and all the coaching, but, um, it was, uh, it was actually two years ago, almost to this time. And, um, uh, we were running, you know, we, we had a strong inbound funnel that, uh, was only getting a 7% conversion rate to opportunity. Um, and, and, and so we felt that there was an issue and, and at the time, um, my CEO and CFO was like, well, we need to get rid of the SDR team. I'm like, ah, I'm like, you might as well get rid of marketing then because, you know, like passing, uh, marketing generated leads to sales.

Like that, it's just dead in the water. I mean, it doesn't, it doesn't work that way anymore. Please don't let that happen. And I, I've said, I'll take, I'll take on the team. Um, our CRO was fantastic and she was great in front of people and we tried to fix it, but I, I was like, I'll, I'll do that. Now I'd never done, I'd never managed SDRs before. And, and so what I did is, and, and my counterpart, the woman that was running the program, we reached out to 25 people on LinkedIn, told them what we were up to, interviewed them and learned so much. Built our network, learned a ton, learned about sales loft. Um, but also like what it is to manage the team, inspire, motivate, build their career path.

You know, I see that stuff on MSP on the modern sales professionals all day long. That stuff is golden. And, and so I do think that asking the right questions, being structured, um, and building that network, you know, of learning, it's kind of how people do learn today is through the experiences of others. Um, and, and so, you know, be, be willing to share it when asked, uh, ask when needed and, and we'll all, you know, the, the goal of our community, uh, is to learn, share and grow together. And, and, and, and that's kind of a foundation of it. I mean, quite honestly, that's why I created this podcast was because I don't read, I don't learn by reading books. Like I feel super bad because everybody sends me their sales book and they want me to read it and whatever.

I literally have a stack of 50 books on my desk that I haven't touched because I don't, I don't like, I, I literally fall asleep when reading like within three pages of a book. I don't care how interesting it is. I'm out. Right. And, and, and, you know, podcasts, like when I listen, I like listening to podcasts, but I find myself sometimes just literally zoning out when I listen to a podcast and all of a sudden I'll be driving and three exits later. Or I'm like, Oh shit, I totally, right. So for me, the way I've learned is actually like this. I, I don't have time these days to sit down and read a novel, but I do have time to sit down with an hour. Who is somebody who's an industry expert and pick their brain about stuff.

And my hope is, is that that, that knowledge that I gained from that person that I gained will translate to my audience. And so it is definitely figure out your learning style, but, you know, interviewing and understanding experiences from people being specific, specific is huge. And, and one more point I wanted to make on that, cause you brought up, um, you know, even in your career and your parents and stuff like that, the kids, parents, uh, learning lesson here for me, I, a friend of mine. So we had, we had season tickets for the Patriots, right. And, and I would go every single Sunday and, and my buddy's dad was the guy who had the season tickets. And I, and, and I grew up with this kid since I was five, six years old.

So to me, even though I, now I was somewhat of a peer to him, obviously, you know, from an age and whatever, I still thought of him as Mr. LaVangie, you know, like, oh, Mr. You know, I didn't, like, his name was Joe, right. That's what you call an adult. Right. But I still literally called him Mr. LaVangie. And I always saw him as my buddy's dad. So what he would do is during the tailgates, we would all be getting drunk and doing our thing. And he'd just be sitting there reading his paper, like quiet as a church mouse, right. Just doing his thing. And I'd, yeah, yeah, whatever. And then he passed away. And the obituary that his son wrote for him, I read, and I was absolutely blown away what this man had done with his life and his career.

He had started four companies. He had, he had started his own venture capital, two different venture capital companies, four different startups, and worked for himself out of his house. And I'm like, and I'm now doing what I do, being a consultant, starting my own company, working out of my house, looking for funding, like all that shit. All I thought to myself was, holy shit, what an opportunity did I miss that to sit down and just talk with him about his experience, about what worked and what didn't work. I mean, I probably could have learned every Sunday I could have gotten a mini MBA from this guy if I had just turned and asked a question and stopped looking at him as my buddy's dad and looked at him as somebody who maybe I could learn something from.

So I implore kids out there, don't ignore your parents' network, don't ignore your friends' parents' network, do a little bit of homework on them. It's amazing once you start to open up your eyes to what your parents do and then who they're connected to. It's like, holy shit, like you've got some cool stories there, right? Yeah, always be curious. Point for you, selling Sherpa, our friend Jeremy Donovan, the summaries of all the sales books. I totally cheat. I go read those and get the highlights and then listen to Jeremy's podcast. I'm like, yeah, okay. I use Get Abstract. It's a five-page summary of every business book out there. They work. They work. Good enough. So let's talk. All right, so now we've got the stages.

What are the stages that you look at from a career development standpoint of how to own each one of them? What are kind of four of them and let's kind of dissect each one of them? Yeah, I reflect back on my own life and then as I coach people, I've had the opportunity to manage people now for over 20 years. And it is like that being a leader, I love being a leader as much as I love marketing. And so the four stages that I kind of recognize, there's the individual contributor stage, there's the first-time manager and thinking through that. Then there's that kind of path to director level where you move up in the organization and there's things that have to change at each one of those stages. And then I call the last one, you could call it a leader, an executive, a C-suite.

By that point, it's very common, the things that you need to do and how you would change to that one. So let's go to an individual contributor. You're hired onto a company. Hopefully, you get hired onto a company like Sales Loft that has a really good culture, a really good support structure, training, and all that other stuff. But let's face it, 90% of the companies out there are not like Sales Loft as far as the support they give specifically to sales. You know what I mean? I think every other position has some structure to it as far as where they fit and how they're trained and how they're developed. And I still think people are still struggling with how to really, truly develop sales reps the right way.

So as an individual, lacking potential resources or support, how do you look at owning your career as an individual contributor? Yeah. I mean, I think when you're an individual contributor, it really is about the results and the tasks kind of that you're accomplishing. And so you want to be able to put that score on the board. You want to be able to figure out how to manage your time and what your ultimate goal is. But a lot of times at the IC level, you are in your own world and controlling your own destiny. And when it comes to learning, and I agree, you get to choose where you work. And while there are an evolution of organizations, there's a great stat in Harvard Business Review of the 4,000 institutions out there.

Only 100 have sales, either courses or curriculum or, if you're lucky, an institute. Yet in our lifetime, 50% of people that graduate from college are going to be in some kind of sales orientation. That was Harvard Business Journal. I can give you the link to it. It was amazing. I read that and I was like, holy cow. So we're not training people outside of those 100 institutions for the sales profession. And so, you know, when you're looking to, this is why being an SDR, coming into that first, is a great opportunity to learn the tools of selling. And I was giving advice to somebody the other day around, you know, there's kind of the two basic things. There's just communication. People said it was a question around, you know, if we don't have a full training or sales enablement team, like, how can I learn?

And it's like, well, there's lots of things you can learn. And there's communication style, time management. I'm sure these are all things that you teach. You know, steadfastness, you know, being able to take rejection and keep motivated. And then being able to close the deal. And if that's the actual deal or a meeting or whatever it is that you're doing, that negotiation and willingness to ask for the close are all traits that will benefit you further in life. Sales or not sales, right? This is basic, fundamental, you know, working style and communication and those kinds of things. So I think that is, you know, and you can find that in books, online, in podcasts. There's so many things that you conscribe to.

So my advice is it's ongoing. And so set aside the hour a week, two hours a week, however committed you are to your own personal development and growth and stick to it to always learn something. Even better, as you're on your path from individual contributor to first-time manager, you've decided that you want to start managing people. Use that as an opportunity to teach others. Like, this is where you get to raise your game. Here's what I've learned. Now I can teach others. By the way, you learn it more when you teach it. 100%. So that's, you know, that's what I would give the advice of that individual contributor. Focus on results. Always be learning. And then look for that opportunity and ask and inform your manager that you're ready to take the next step.

And enroll them in your development to coach you to get there. So I got a very concrete example that I just, like, right after, right before our call here, I got on. So I did one of those coaching calls, woman. She actually gave me, if you wanted to give me some insights on podcasts and that type of stuff on, you know, what she would like to hear. And one of them was this. She's a little bit later in her career. She had had to take some time off to take care of her family. Her parents were really sick and stuff. So, you know, she's 37 years old. She's now an SDR because she wanted to get into the same. She starts at the SDR role. And her frustration is this, is that she's like, John, what do you do when you have an AE, right?

An SDR-AE relationship when the AE just literally doesn't give a shit, like doesn't work with you, doesn't give you any guidance. It's kind of like, yeah, do whatever. You know, I kind of trust you, but also is lazy and like perfect example here. And I don't want to call her out. I don't want to be too specific with this example. But she, like, literally, she just gave me an example of she qualified this account. The customer is super excited about the opportunity and the solution. And she flipped it over to the AE. And the AE asked, hey, the first question the AE asked was, did you talk to her about the fact that our minimum investment is like $30,000 or whatever it was, right? And she's like, well, no, but she needs the solution.

She's excited about the solution. So he was like, all right, fine. He took the call. Literally, the first question he asked was, do you know what our minimum is? Told her. And the client was like, yeah, we can't afford that. See you later. And hung up. And, I mean, to me, that's just infuriating because you don't know whether they could afford that or not. Like, if you can show the ROI and the, you know, 1 to 10 ratio and that type of stuff, you should be able to do it. So she's saying, like, what do I do about this? And so put that hat on, right? How do you control your career in that scenario? And, by the way, in her previous role in an organization, the same type of thing happened. And she was actually let go.

And the feedback was because she couldn't get along with her AE. And she's a hard charger. She's a high dean. She's got a motor. And she wants to be successful. And she knows, at 37 years old, I don't have time to deal with this shit. Like, let's get some shit done. Let's work together. And so she's super frustrated with the fact that, you know, the AEs, they're more senior. They get, you know, they pretty much whatever they say goes. And now she's in a similar situation. So let's use that as an example of taking Crowley. That's a tough one. It is. Well, first of all, can we say that Bant is dead? And really, it's just about the need. Yes, thank you. But, you know, I think there's two options for her.

I think you do have to take control of your own career. And it does depend on the environment. That's super unfortunate about what happened to her before. You know, my first inclination would be to see if she could support another rep. I always say go where the energy is, right? Like, don't push a rock up hill when you don't have to. And so if there's, you know, if there's another opportunity for her to support somebody else, I would ask for that. If not... But how? But let me interrupt real quick. So she's already been let go because she couldn't get along with their AE. So that's a little bit of a historical benchmark there for her. Perception and reality. They don't know the details of that.

Now, I'm a new SDR at a new company. I get assigned this debt of an AE. I'm doing everything I can to push that rock uphill. You're my boss, Sydney. I come to you and say, what? Without being a complainer. You know what I mean? Without being somebody who's just like, oh, you just can't get along. And, oh, that's just Joey. Joey's, you know, that's how he is. You got to figure it out. You know what I mean? But if I come to you six months into my job as an SDR and start complaining that my AE sucks and I want to be... What's that approach? Yeah, I mean, you're probably... So, I mean, I'd ask for advice and coaching. I'd try and find out what the track record of that AE was in terms of his success with previous SDRs.

And what was it about that relationship that worked? And what could you model into that that had happened before? So she can kind of figure out the guardrails. And maybe she can expand to another AE so she does get the balance. So not... I don't want to transition to, hey, I want to try to. Like, I'll work extra hard to support another one, take a higher quota, like if she's a D, hard charger, and see if there's a difference in the way that she's supporting a couple of reps, perhaps. So, I mean, it's a tough situation when you're put in a world that you have to work through. But hey, guess what? We have to work with people, unfortunately, sometimes that you don't get along with and you've got to find that middle ground.

I think a good advice, too, is humanizing that person. Like, how can she build a relationship? What do they have in common? If that person is not yet warmed up to her, you know, that could be an area, too. And then once that relationship is established, she can be a little bit more honest and saying, okay, help me help you. You know, here's what I need. Here's what you need. Can we come to a mutual agreement in terms of coaching you can provide to me? And then I'll continue to give good service to you. Yeah, I think actually that's great advice as far as understanding. It's almost the same thing with a manager, right? Like, you want to understand what makes that person tick. And I don't mean just from a comp standpoint.

I mean genuinely what makes them tick and what makes them happy. You know, what are their goals, life goals? Forget about, you know, I know what your metric goals are, right? That's obvious. Everybody knows those. But genuinely, what, you know, are you, do you have a family? Do you want to get home earlier for your kids? Like, do you want to be able to, you know what I mean? Those type of things. And if she can tap into that, you know, for instance, if I had an SDR and they talked to me about how I'm trying to get off an airplane and I want to be home with my daughter more and that type of stuff. And then they played towards that, they would have my ear all day long. You know what I mean? But if they just come in saying, hey, what deals do you want me to work on this month?

And, you know, how many emails do you want me to send out? I'll be like, yeah, whatever. Just kind of, I don't know, give me some meetings. So. Well, we know that selling is all about the relationships these days. So I guess the first relationship you have is with your own supporting team. Yeah, you do. So let's now, oh, and one more, because I think it translates into the next stage here. There's one of the things I always recommend everybody do is they document, they document, they put structure and process to everything they do. And they almost force the interaction and the reciprocation, if you will. It's like clients. You know, I wrote a little post a little while ago called, you know, everybody needs structure in the sense that if you don't have structure, it tends to fall apart.

And people like to be guided through a process for the most part, right? And so if you have a process and you can guide them through it and put some structure to it, they feel more comfortable working with you as part of that. So, you know, have an agenda for every call you have with your AE. Summarize that conversation. Get their confirmation of it. You know, when you have a conversation with a client, document that. Summarize it. CC, ask for the referral back. So that now when the AE comes back and says, that's a shit lead, you have a documented thing where the client said that these are all the things that they were looking for. You know what I mean? So you at least back yourself up. And that kind of leads to that next role, which is now you're going to be the manager, right?

I mean, in sales specifically, we talked about the lack of education in sales. At least it's there. At least there's sales training for sales reps. But man, sales management, usually sales management is, hey, John, you're the best of the team. So congrats, you're a manager. Now go show everybody to do what you do. And it's like, what? You know what I mean? With no guidance. And I always say, actually, usually the best rep on the team is usually the worst choice for a manager. Because they're kind of that artist, right? They're the one who just does. They have that drive. They have that motor. But they can't really articulate how they do what they do. So if they can't put a process around it, they can't teach everybody else how to do it.

So say you have this aspiration as an individual contributor. You want to be a manager. First question for you is this. Do you ask for it or do you earn it? In the sense that there are people that, you know, part of me says, I want the aspiration. I want to hear a rep says, yes, I want to be a manager. How do I get there? The other part of me says, perfect what you're doing right now. Crush what you're doing right now. And then earn that opportunity. So don't talk to me about it yet. So where are you on the ask for it versus earn it? And when should you do it? Both. I'm on the both scale. I want people to have passion for what they're doing and a career plan and especially for my high potential, high performers that I can help them into that.

And while I may not have a role for them yet, which is your responsibility as a manager to set expectations, I can start to develop certain skills or help you develop certain skills that will make you more qualified for the next phase in your career. And then you get the, and now you've been demonstrating it. The opportunity comes available and you've earned it. So a lot of coaching that I do here is really about learning those skills. And so this is, you know, when you get to that first time manager, now all of a sudden you're leading others. So you need skills around inspiration and motivation, providing feedback, being a, you know, being, being able to articulate expectations. Like people, people have a hard time doing that, holding each other accountable.

You said you were going to do that. You, you, you didn't do that. Let's talk about why. Why do you think that's such a problem? I don't know. Why do you think that's such a problem to, to set expectations and hold people accountable for them? Because I, but it baffles me. They're uncomfortable conversations a lot of time because people then feel like they're failing. But maybe they need help. I think it's the way that we orient into the conversation. It's like, okay, you said you were going to do that. Gosh, it didn't happen. Like, let's talk about why it didn't happen. What, what do I own in this? What do you own in this? And how do we change that trajectory for the future? It's not a blame.

Maybe you set the bar too high, right? Maybe, maybe, maybe they didn't have a skill that they needed. Maybe they missed something. Maybe they aren't doing their job and you do need to hold them accountable so they step up. It could be all of these things. But what I always like to do is assume best intentions. Sure. That they were trying hard and they, they were doing something. And so this is a coaching opportunity for the leader, to the manager, that the manager learns those lessons so they can then do that. But I do think people like that first time that you have to hold somebody accountable. And, and, and so, you know, practice with a peer, practice with your manager, right? What you think versus what you say.

Those are all good skills for kind of practicing into something that's going to be uncomfortable because, guess what? Every step up, the conversations get harder. Harder. They get harder. You know, it is. So the other thing that I would say in that first time manager category, things to look for skills, right? This is a delegating is another really important one. People, I see people fail at this all the time. They're wonderful individual contributors. They take all this on, they start to manage, and then they take all the work on of everybody that reports to them. That is not a recipe for success. You're going to have to learn delegation. And when you delegate, that means they may not do it exactly as you've done it.

And so the best thing that I've learned in delegation is, you know, to delegate and give feedback early and often and tell, learn with the person, how they work, how you work, setting expectations, giving feedback. But I think that's one of the most critical, second critical skills in first time managing. Yeah, and I actually think that's one of my hardest, like both my wife and I, we both have our own little small businesses. We both work out of the house here. And I will tell you, I've at least been able to adjust, you know, adjust it a little bit. But my comfort level, you know, the whole mentality of it's faster me to just do this than show somebody else how to do this, that only works to a certain point.

And then it absolutely breaks because you can't just do that. And it's not a scalable thing, right? You know, I bring this to Morgan, you know, I hired Morgan a few years back and it was funny because, you know, watching him deliver my content was brutal. And I, and I was just like, oh my God, you're not doing it the way I do it. Like stop doing it that way. And I just, I had to get very comfortable with him, letting him figure out his own style, even though I might not have liked it, but it's still, but, but whether I liked it or not, it wasn't a point. It was, did it drive the result we were looking for, right? And hopefully you picked up a couple of things that he did, right? I think that's, you know, I, I, I do it my way.

It's the right way. Not necessarily, but you can give guidelines, right? Like let's let them try, let them, you know, collaborate with them. But listen, cause there, there might be a different way that's not your way. And you can, you can also learn as a manager. And as a, as a, uh, once manager, and then I was on my own for, you know, for years, right? I was doing my own thing for, for 10 years. And then I picked this kid up and now I got to actually manage again. Right. And I'm like, shit. And I remember he came on board October, 2017, uh, to the end of 2018, we had his performance review and, and he knows this, so he doesn't mind me saying this. Um, he didn't come in even remotely close to where I thought he was going to come in at.

Okay. As far as the number of days trained. Okay. I'm sitting there going, I run a whole company. You know, I do 90 days of training a year, plus managing four people, plus traveling all around the world. Like if you can't do 60 or 70, like something's wrong with you. Right. So that's kind of what we put there. And we looked at it and we both agreed this is a good goal and all that other stuff. Right. And he, and he missed it. He was like 50% as far as the, the delivery of, of training. And I was, I was pretty furious because that's exactly how much we missed our target by as far as the company was concerned. And I remember I was going to come in on his performance review and he knew it. He knew I was going to come heavy, but thank God.

What I did was before I went heavy and criticized and kind of was like, basically, should I get off the pot? You got to figure this out or else I got to figure out something else. I asked him, I said, so Morgan, before I get into this, how do you feel like you did last year? And what he said was, he goes, you know what, John? I don't think I did that great. He goes, and, and let me tell you why I think I didn't do that great. He goes, everything last year was new for me. He goes, literally, I was before this job, I was an SDR and an SDR manager. I had one job, one company, and I came in in the morning and I left at night and that's what I did. And I worked harder than everybody else, but I had a very singular purpose.

Now I have to do the SDR role. I also have to do the AE role. I also have to do the customer success role. I also have to figure out how to train. I also figure out how to travel. He's like, I mean, he had never had a passport before me. He had never done an expense report before me. So little things like somebody like you and me would take for granted as far as expense reports. It's like, what are you fucking talking about? Like put it, you know, like put it on a spreadsheet and send it in. Like who gives a shit that all, as he was explaining all that stuff being new to him, I kind of sat back and I was like, you know what, all right, you're right. You know, maybe the expectations were just, I don't think the results expectations were too much, but I think the overall expectation was too much understanding where he was coming from.

And so I basically took my entire performance review that I was going to give him and flushed it down the toilet. And we started talking about, okay, all right, I see that, you know, and, and, and we made a plan and now he's crushing it. Right. So I think that to your point of listening and being somewhat empathetic about anybody's situation, right. With your manager, with the AE or any of that stuff, but then working together to kind of say, you know, it's not my way or the highway, it's let's work together on this so that we can, you know, figure out the best of both worlds here. Yeah. That drives me to the director, the story that I wanted to share about director too, because I think it is having a manager that's willing to be open and honest with you that you trust.

And, and I, I had hit a ceiling. I, I, I was working a hundred hour weeks and it seemed like every big project got handed to me and I would crush it and I couldn't understand why I was not being promoted to director. Like, what is it? Like, what else do I have to do? And it was finally until my boss at the time, Eugene Lee, he's like, Sydney, he's like, it's, you know, you are going to continue to get all the hard projects because you get shit done and you get it done well. But the way that you get it done is holding you back. You know, you leave a wake behind you. You're not, you're not building relationships. You're crushing through. And, and he's like, it's actually the, the, your behavior, not your results.

And so you need to start thinking about how you show up, how you make other people feel and building those relationships across the company. At that time, I don't know if it's still the case at Adobe, it was almost like a thumbs up, thumbs down. There was the marketing council. And if you wanted to be promoted, it was really hard to be a group manager at the time to director. They, they limited the number of roles in, in the company. And so the marketing council had to vote on who would get promoted to director. It was crazy. You could get hired in, they didn't have to vote on that. But to get promoted, you had to get thumbs up across the board. And name me was like thinking my results mattered.

And it wasn't, it was my reputation that mattered. And so I had to change the reputation. And that's that turning point in life we were chatting about earlier. It's like, at what time did you know that you took control? Like I was pretty driven. I, I, I knew I wanted to continue to grow, but I didn't take control of my career until I realized that relationship. And I was lucky enough to get a coach and I'll never forget it. Um, my coach Don, he, he, he started listening in on my calls and he's like, you sound like a German drill sergeant, like marching through and, you know, how do you talk to these people? And he's like, we got to soften you up and you got to like figure out what's going on.

I mean, it took eight years to reprogram. I mean, I did get promoted, like, right, you know, it would be within a year. Um, but you know, to learn that as you go into the director level, as you go into that, it's, it's totally different now. Now it's about relationships across the organization, who you're building that with, owning something that's more than your just direct line of influence. And, and now it's about influencing and, um, and orienting, you know, how do you, how do you get someone to realize that your priority is their priority? This is hard stuff, right? Um, and, and fortunately in big companies too, you start to fall into politics here. So you got to figure out how to navigate, you know, build your network and all that kind of stuff.

Hopefully, you know, a lot of us don't, I choose to work in smaller companies because it's just not something I want to spend my time doing anymore, but you know, it is the reality of the situation depending on where you, where you work. I mean, that's what that to me is. And this is also kind of goes to eventually knowing what your strengths and weaknesses are. Um, and like you, you don't really know that when you, when you first get into business, right. But what I, what, what I found real that I still have, and this is why I work for myself. I cannot figure out how to play the game when it comes to the corporate culture game. Like, right. Cause like, especially as middle management or even senior management, cause you have to manage up and manage down.

And those are two different skill sets, right? Managing up so that the perception of you is positive enough so you can get those promotions to those next levels, but also managing down so that your team respects you when you're not, you know, and you're the filter of the ship that's coming downhill. Right. And I, I don't know. And managing across, John. Yeah. Managing across, actually, that was another, um, and I know we're coming to the other time at kind of the end here, but, um, and I've got a hard stop in two minutes. Yeah. So, uh, so, um, managing across, that's the last lesson that I'll share. And that is at leadership. And that's when you realize who your first team is. Um, and so coming into my last company, coming into this company, and I was very transparent about it.

I shared it with my direct reports. It's like, Hey, I'm here. I first have to develop relationships with my peer group. I'm, I'm here first as a leader, second running marketing. Yeah. And I am here to empower the folks that, that I get the pleasure to work with every day on my team. But they, they lead, Mark, I help orchestrate, they lead, they're the day-to-day and, and I'm a, I'm a leader. And so for that next level to get up to, you know, the, the executive level or whatever you want to call it, you know, that all the, all the lessons before delegation, accountability, inspiration, motivation, communication, all super important and empathy for people. But leadership is, you've got to be able to take your hat off.

It's not about marketing what I own. It's about my role as a leader in this company and what, what we care about, which is our customer success, you know, um, helping each other out. And so in the, in the things that I'm most proud of at sales off so far is not, not just, I mean, like the results are great, but the relationships that we're building across team, how marketing is supporting customer success and service, how we're supporting people operations and the work that we do around employee engagement, how we're supporting sales, of course, pipeline, messaging, training, all that stuff. That is where, you know, when you get to that level, that's my recommendation of, of how to think about the role and, and where you spend your time, um, and then how you think about approaching your job.

Yeah. And, and also again, knowing, being self-aware, whether or not it's really for you, you know what I mean? Like there are certain people that just are better managers, they're better execution and leadership, lead it like leadership in that you can lead in a bunch of different ways, but like leading a company or leading a division or leading a, something like a bigger group for bigger purpose. Some people, it's just not their skillset. Some people, they're just not good at it or, you know, it just, it's not as comfortable. So I think, you know, the more you try different things out and, and you pay attention, the more you start to figure out where your skillsets are, and then you start to figure out that path.

Right. Because I think self-awareness is, uh, is an important skill, uh, to, to hone in when you're growing through your careers, figuring out what you're great at and what you're not. And you know what, it's really easy. Three things, right? When you sit down with people, figure out who that, you know, your peer group or the influencers are, and you only have to ask three questions. What's working, what's not working. And what could I be doing better or differently to, to serve you or to serve the company? That's it. It's not a, it's not a, you know, a 360 with a hundred questions. It's three questions. Yep. I love it. Awesome. Well, Sydney, uh, love, I mean, I think you and I should have a conversation about sales and marketing alignment.

We, you know, uh, we can talk about a million different things here, but, uh, we'll, we'll save that for another podcast. Talk to us a little bit about, um, what are you really focusing right now with sales law? Cause I know you guys are making a shift in, you know, you're, uh, trying to go whole customer life cycle and you're trying to, you know, you're doing some big campaigns in San Francisco. So what should people be paying attention to right now with sales loft and what's the message you want and how can they stay connected with you? Yeah. First and foremost, it's the thing that we're most passionate about and that's building a community of sales professionals around the world, right? Where, where they can learn, grow, share together.

So whatever we can do in terms of inspiring the sales profession, teaching, learning, and building that network, that's priority number one for, for, for me as the, the, the marketing leader at, um, um, at sales loft. The second is absolutely we're looking to, how do we serve all those revenue professionals or customer facing individuals so they can communicate more effectively and more consistently across the entire customer life cycle. You think about it, they might be using sales loft with the SDR team or the inside sales team. That customer has the experience with you across all of them. Why would you give them less of an experience once they become a customer? So having the ability to serve the customer success team and the renewals team or wing-to-wing account executives and to think differently about what they need and how to serve them best.

Absolutely. And the third is, you know, I'm super proud of how we're able to serve larger customers. We, we have won some great logos lately. Um, can't quite say their names because the bigger they are, the harder they, you know, they harder, the harder they protect their brand. But, you know, looking at how, how this sales engagement is starting to impact sales all across the board. It's not just about SaaS startups that know how to use technology to win differently. We're talking thousand person sales organizations that are transforming the way that they sell. And, and that's inspiring. And, and, and that's when, you know, something big is, is happening in the market. And we're just seeing this continuous momentum and we want to do our best to be able to serve customer, small customers, medium customers, large customers, uh, any, any, any customer that wants to use sales engagement to differentiate how they build that relationship with their buyers.

Love it. Yeah. And, and just for everybody who doesn't know, it's under a rock, you know, I, that's why, you know, the lines, not only because of what you guys are doing from a tech standpoint, but also just from an overall ethos standpoint and what, you know, how you're trying to elevate the overall profession of sales. I mean, I've known Kyle since he started and, and I'm, I'm, you know, investing in people. I've always said, if I'm, I'm never going to work for anybody again in my life because I'm such a pain in the ass to deal with. But if, just if there was one company I would ever go work for, it would be Sales Loft, um, just because of what you guys are building over there. So I genuinely appreciate everything you do, uh, and what Sales Loft is doing for the community.

So thank you very much. You're part of it, John. You're part of it. It's awesome. It's awesome. Thank you so much. I really, really appreciate the opportunity to like be on your podcast. You've got so many loyal followers and just, just time with you is awesome. I love it. So I'm going to be able to, on the next, uh, sales, uh, I don't know. I can't say it yet. Cause I don't think you guys have announced it yet. I'm telling the company right now. That's where I'm going to do next. We can cut it up and play some of those stuff again. All right. There you go. Awesome. Awesome. Okay. Thanks, John. We'll see you soon. Yeah. And for those of you out there, you know, hopefully you got as much value out of this conversation as I did.

And like I always say, go make somebody happy today. Make them smile. No matter how bad your day went, if you made somebody smile, you know, you had a good day. So, all right. So have a great week, everybody. Let's make it happen. Thanks. I'll see you next time.