The Corporate Human Playbook with Casey Calkins

[00:00:00] Welcome to the Wise Podcast, where we celebrate the brilliance of women inspiring sales excellence. I’m your host, Lauren Palmer. Casey Calkins is the founder of C2it Partners, where she develops people first, leaders who drive sustainable results without burning out with a background spanning big tech companies like Salesforce.

[00:00:21] Personal finance and psychology. Casey brings a unique combination of corporate leadership experience and behavioral science expertise to help newly promoted managers and frustrated executives break free from old school leadership approaches that fuel instability and turnover. Her signature approach focuses on the inner work and human skills.

[00:00:44] That are often overlooked in corporate America. The psychological foundation that determines whether someone becomes a leader that people want to work for, or just another manager that they’re forced to tolerate. Casey holds the PCC certification from the International Coaching Federation and degrees in both psychology and sociology.

[00:01:05] She offers one-to-one coaching programs. Group coaching programs and corporate workshops designed to help leaders master the inner work that fuels lasting success for themselves and their teams. Casey, thank you so much for joining the WISE Podcast.

[00:01:21] Thank you for having me, Lauren.

[00:01:23] It’s such a delight. I loved our conversation when we originally chatted.

[00:01:27] I think we’ve had a few now, and obviously your bio is so extensive with everything that you’ve done, so I thought maybe we’d just start on that because I covered a lot and your bio, and obviously the listeners will have heard that first, but. I’d love to talk about your work with c Twoit Partners, your business.

[00:01:45] Um, and for me what really stood out was your approach, which focuses on the inner work and human skills that are often overlooked in corporate America. Um, so particularly coming from the uk. I’d love to dig into that a little bit, Casey, like, why do you think that the human element is overlooked so much in the us?

[00:02:09] So. I think I would start by by asking you a question ’cause you have worked overseas, whereas I have not worked overseas. I’ve only been in corporate America, my entirety of my career. So just did you, have you noticed a difference?

[00:02:25] I have. I’ve noticed a difference. The way I would describe it here is maybe the speed and the pace and the kind of hustle culture.

[00:02:35] It feels more paramount. Here than the uk Um, the UK feels a bit more slower and people led here is more about revenues, numbers and how are we gonna hit them fast, maybe because it’s so competitive. So yes, I have felt a difference for sure.

[00:02:53] Okay. Um, because I was gonna say, I, I think it’s prevalent in corporate America.

[00:02:58] I think it’s also something that’s prevalent in the west too. Mm-hmm. So I think there’s also a lot of differences between. Um, anywhere in the west and places that would arguably be other parts of the world. And you could argue that, well, that’s obvious because the west is leading most corporations globally.

[00:03:16] Um, but I think the answer is kind of nuanced. I think it’s a combination of speaking to America specifically. I think it could be partially our, our, some cultural, uh, elements that go with it. First being our Puritan roots. Um, not to get nerdy there for a minute, but you know, we, we as a culture were defined early on by suffering and hard work as being virtuous.

[00:03:49] So I think that could be one element of it. I think there’s a lot of kind of rugged individualism. That was the basis of what our country was founded on. We’re very like. Get out there, rise and grind, you know, fight the power, um, with how we just came to be. And I think that capitalism kind of fuels that speed and pace of business.

[00:04:19] So I think you combine all of those things and it’s really easy for. The inner work or the human skills to be labeled as soft or less important or less valuable because, well, for one, they’re frankly harder. For two, they take more time and they don’t have immediate return. In a capitalistic society, we’re fueled based on.

[00:04:51] Revenue, and this is by the way, regardless of your actual job title, is tied to revenue in corporate America. Everything ties back to revenue, right? And as a result, it’s not just revenue, it’s immediate short-term revenue quarter over quarter, month over month, year over year, rather than thinking about lasting sustainable results.

[00:05:13] So, I don’t know. Kinda a nuanced answer.

[00:05:15] Yeah, I love that. And I think, um. Tenure as well. Like if you actually invest in the human skills and you take some time to really like breed a team that is aligned to your vision mission, and they feel respected and valued, that’s gonna give you a longer tenure of staff within your business.

[00:05:34] I’ve also seen here that that turnover is higher, maybe because of. Your point around capitalism and immediate return and revenue, and there’s this kind of hunt and chase all the time. Whereas if you actually invest at the front end in your team and your staff and you have a happy group of employees who are then striving for revenue, ultimately they’re gonna stay at the business longer.

[00:05:57] So

[00:05:58] well, sure. And I think that all of those things we just talked about and the speed is really magnified within. The spaces of tech and startups, um, because everyone is really focused on top line revenue and they’re trying to prove their worth to investors. They’re also trying to continue on the up and to the right dramatic trajectory to justify either an acquisition or going public, and both of which require a lot of that speed, but I think it can sometimes be at the expense of.

[00:06:34] The employee and the human capital, the more that we treat human capital at the same way that treat we treat other commodities, the more that it will ultimately result in companies rising really fast and fading or dying really fast too.

[00:06:55] Yeah, absolutely. I spoke to one of my guests who I think you know very well, it’s Monica Stewart.

[00:07:01] I do know Monica and

[00:07:02] she talked about this exact topic where we, we kind of phrased it as, especially for startups is like slowing down to speed up. And I think fundamentally what happens is startups. Go, oh my gosh, we need to get revenue and we need to hit these crazy ambitious revenue goals now. But really, maybe they should have started to think about investing in a sales team months earlier so that there is that ramp time, there is that time to embed in the business and really understand each other from a people perspective until you’re ready to hit go.

[00:07:37] ’cause I’ve seen it happen too many times in my career. It’s like, we need salespeople now. Put them in the role, give them a couple of weeks training. Then tell them, well, you’ve gotta hit these absolutely crazy growth goals. And it doesn’t, it doesn’t work like that, does it? It takes a long time.

[00:07:53] You know, I think about, um, I get this visual of like, uh, a slow burn versus a fast burn with, you know, this image of fire.

[00:08:03] I think a lot in metaphors and visual things. When I used to manage a team, people used to laugh at me. What? Because I would make a lot of references too. Other things in life that would get a little philosophical. But, um, you know, if you think about a piece of paper and if the end goal is to burn the piece of paper, you have two ways you can go about that.

[00:08:28] Have you ever noticed the difference in the speed? That’s, and, and by the way, the, the end goal is to burn through the piece of paper. It is your fuel for warmth. Okay. In this image, let’s think about that image for a moment. So you want it to be lasting. If you just light that piece of paper on fire, it’s going to burn out within seconds.

[00:08:50] But if you make the simple choice of twisting that piece of paper, like it not into a, into a roll, and then light it on fire and I’m talking crumpling it, it’s gonna last a lot longer and keep you warmer a lot longer. But it requires you to just think. Of a solution that’s going to just try and get it to the same end goal, but.

[00:09:18] A lasting end goal. If that will, if you, if that makes sense.

[00:09:21] Definitely. Let’s, let’s, let’s jump onto that. ’cause the metaphor for me is like symptomatic of the stuff that you do as well. Helping leaders and managers avoid burnout. When you were talking about the paper Oh yeah. I was like. Burn out. Yeah.

[00:09:36] Because that’s gonna burn people out as well as, you know, get the, get the business results fast, but not give them the longevity they need, so. Mm-hmm. You spend a lot of time, Casey, and, and I’m sure throughout your career you’ve been IC and then you’ve gone into leadership, and now you’re coaching and training, you know, newly promoted managers.

[00:09:55] What I tend to see is top performing reps amazing at what they do, promoted into leadership and then told, Hey, everything that you are good at, can you just teach the team exactly what you do? And it doesn’t really work like that because each of us have their own of our own skills and superpowers and to tell.

[00:10:16] A manager just to just replicate what you’ve done doesn’t really work. So my question to you is, for those who, and this topic is quite relevant for anyone who is maybe new into leadership or wants to go into leadership, what are the tools that they need to succeed going from IC to leadership? ’cause it is very different, especially if you’re successful on your own.

[00:10:39] Right? So when you get promoted to being a leader, I think. It’s interesting that statement of you’re told you were successful, now go teach everyone else how to be successful too. Um, but no one gives you those tools to, to instantly become a teacher. Um, you know, I have two children who are ages seven and 10, and I know that my, my kids’ teachers went through a lot of extensive training just on knowing, knowing how two plus two equals four, but on understanding how.

[00:11:12] My kids’ brains work so that they can understand why two plus two equals four. Um, it’s actually more important to understand how to communicate an idea than to just know the answer. Um, so I think that the biggest things I work with my clients on are some of the things that they often feel like they don’t have the time to focus on.

[00:11:34] Um, first off is delegation strategies and letting go of control and understanding. What types of failures are okay to allow your team to have? I also work with them heavily on building, really impactful one-on-ones in team meetings. ’cause I actually think those are like the cornerstone of any frontline leader when it comes to everything.

[00:12:02] And more often than not, what happens is you get thrown in and you’re told to have one-on-ones with everyone. Tell me if you can relate to this. And then the calendar gets overloaded and it’s, you know what, we’ve gotta push this, or we’ve gotta, or we’ve gotta scale this back to 15 minutes. Or, you know what, let’s just make it a quick phone call while, while we’re walking.

[00:12:23] And then there is no real structure to it if it even happens at all. And it becomes just like a little bit of a quick check-in, and it’s usually just. Let’s go through. If you’re in sales, it’s, let’s just go through the deals and I’ll just tell you what to do and then we’ll move on with our day.

[00:12:40] Yeah, I, I would agree, but I must say I’m regimented with my one-to-ones.

[00:12:46] That’s good. As a leader. That’s good. I have two a week, two hours with each rep a week. Okay. Um, my team isn’t huge, so I also know that I’m privileged to be able to do that, but those. Don’t get moved unless there is like fire, um, and serious emergency. And, and we have a, a very clear structure to those one-to-ones that are focused around.

[00:13:10] One of those sessions will be on pipeline deal review and what’s stalling and how we can surround the buyer group. But then the other one is like deep coaching, so that’s where they always send me their calls and I will listen to them and give advice on, you know, maybe discovery call questions that might have been more valuable or role plays that we could then do because it, this is the thing, anyone who wants to tread their toes into sales leadership, like just remember you.

[00:13:38] Coaching isn’t just instructing, it is dynamic and it is changing every day because every single one of your reps is different. And also you are gonna hear calls one minute. They might be amazing at nailing that part of the pitch. Next minute. Maybe it’s, it’s fallen a little bit. You have be on it. All the time.

[00:13:57] Um, and I think you’re so right, Casey, because if you come into the sales leadership and you think, oh, it’s fine. My team will be just as self-sufficient as I am, you’re wrong because teams need you a lot.

[00:14:11] Well, and yeah, so, so a lot of it is just helping to coach my clients on letting go of control and helping them to understand how to.

[00:14:23] Effectively build systems that will result in mutual accountability with their teams. And understanding the delineation between this is a really big deal that I need to step in on, or this is something that I can let go and let that person figure it out on their own and maybe even fail a little bit.

[00:14:42] Um,

[00:14:43] yeah, it’s such a good point. Let them, let them fail a little, a little bit, I must say. I think. That was my hardest part when I sort of treaded into that territory is the control piece and the delegation piece. So I loved how you sort of said that, right at the offset actually, that is what you have to learn to let go.

[00:15:01] Yeah. And like they’re not gonna do things the way that you do things. They’re just not, no, they’re a different person, but you, they, you have to be there to help. Them learn from their mistakes and and guide them because I read some great articles from you actually, Casey, about micromanagement as well.

[00:15:19] ’cause it’s very easy to tread into that territory, isn’t it? Being, thinking that you are being helpful, being on top of them all the time. I know I’ve done this, I will put my hands up and say, and I hated myself for being that micromanager, but I felt that that was the only way.

[00:15:36] Well, yes, and it’s interesting, I haven’t met a single person.

[00:15:40] Um, that has said, you know what, the only way that I can make sure things get done is by just riding everyone’s ass all the time. That’s, nobody wants to do that right now. A single person wants to do that as a, as a leader, and nobody intentionally becomes a micromanager. You do things, to your point, Lauren, with the intention of being helpful.

[00:16:00] Mm-hmm.

[00:16:00] Um, but a lot of times that takes away the ownership as a result.

[00:16:05] What is your view though, on. Diagnosis of where things haven’t worked. So for example, a rep. Isn’t driving the amount of pipeline that they should be and that meets KPIs and expectations. And so rather than be that micromanager being CC’d into every email, you then don’t have any visibility on why that might be happening.

[00:16:31] The way that I’ve approached it, and I might be wrong, and I’m okay if you call me out on the podcast being wrong, it’s okay, but the way I’ve tried to approach it is let’s diagnose your messaging. What are you saying? How are you threading? What are you sending? What is the positioning that you are giving?

[00:16:47] Because if you have a call and someone drops off and ghosts you, or if you’re sending emails and no one’s responding, we have to try and diagnose why? Because if that’s not symptomatic of the rest of the team. Is it a simple tweak that we could make that could change things for you? So I wonder like, how do you approach when you don’t have a visibility as a sales leader?

[00:17:10] You have zero visibility. You’re not in the office with them, you can’t see their emails, you can’t hear their calls. How do you recommend a sales leader managing that?

[00:17:21] Yeah. Um, I would back up and first ask the question of does the rep. Know that this is a problem. Right. And I think you have to first ask that question because the, the individual needs to take equal ownership for the issue to their manager.

[00:17:44] And too often we will have new managers, in particular, they will think that by being empathetic, they should be sympathetic of the hardship and let core performance just kinda slide. Because, oh, it’s just really hard for them. But the reality is, um, there needs to be mutual, mutual accountability comes from understanding the importance of a situation and, um, wanting to improve.

[00:18:13] Right? So contingent that all those things are there, I would first frame it as asking your report. What do you think you need help on? Where do you need support? I can’t be there all the time, so I’m gonna ask you to first self-reflect where do you think things are going wrong? And not only will that tell you a lot about trying to like sniff out where the problem might be, it’ll also tell you a lot about where you need to coach them.

[00:18:50] Because if the response is, I have bad accounts. Then there needs to be a much deeper conversation around self-awareness and, um,

[00:19:06] I’m not sure where to answer this from there. Yeah, that’s just a really difficult one. I think that if you’ve worked it’s true in a job long enough and you’ve been in sales long enough, yeah. It’s like you need to know. If you don’t blame the accounts to your management. Oh, I mean, don’t blame the patch on your performance.

[00:19:23] Yeah. Okay. Um, because even if you have a difficult patch, you have to have the tenacity and the growth mindset to know that there’s always another way and there is another way. It might be more difficult than other people. Mm-hmm. And that may be true. Mm-hmm. But that doesn’t mean we can’t overcome it. Um,

[00:19:40] yeah, go ahead.

[00:19:41] I was gonna say the biggest thing I took away from that as well is. As a leader, not always dictating where you think they need to focus or where you think their shortfalls are. You can observe and have a view of that. Sure. But one of the things we did as well as development plans, where I put two things that I think from observation they could work on and then said, I want you to put two things, and then I asked them.

[00:20:07] What do you want to focus? What do you think is the number one thing you need to work on now that we can do together? Because it comes from them to your point. It’s that self-awareness piece

[00:20:16] has to, otherwise you’re duplicating. Mm-hmm. Um, my question for you, I love that by the way. I think individual development plans are really, really important.

[00:20:25] Um, but my question to you is, do you fill it out first or do they fill it out first?

[00:20:29] Um, recently it was me first. Uh, did I send it to them? Yes, I think I, I filled it and sent it to them and asked them to put theirs in. So if you suggest it the other way around, that would be interesting too. I would actually

[00:20:39] challenge you to do it the other way around because I think that they will be influenced by your responses with how they fill it out.

[00:20:46] And I think it would be really interesting if you were to ask your, your reps for before their next quarter Q, quarter QBR quarterly business review or their next big one-on-one to say. Here is a blank template for an individual development plan. I, I need you to have this completed by our next one-on-one so we can discuss it and I will then bring to the table what are my two, what’s my feedback, and then go from there.

[00:21:11] I think this is a big thing with one-on-ones too. I think when it comes to like this quote, culture of documentation, you know, most managers, particularly in tech are, are potentially taught that they should have a one-on-one document that’s a shared document, but it very often. Becomes a one-sided document and it becomes something that the manager keeps notes in, which I would argue as No, no, no.

[00:21:35] It needs to be the, the report comes prepared and puts the agenda in there for the meeting. It’s established that I as your manager in one-on-ones, wanna make sure that we discuss a few things and these are the things I always wanna discuss, but I wanna make sure that your agenda is top of mind too, so that if we can’t get to all those things, we still will and I expect.

[00:21:57] My directs to be keeping notes on our conversation in there. They should be typing just like I am, right? So if we’re talking about something, I might ask them, and if I see them just kinda like smiling and nodding and we’re talking about how to problem solve a deal, I’ll say, where are you writing this down?

[00:22:16] And they’ll say, oh, my piece of paper. No, no, no. You’re writing it in our one-on-one document. Right? Because people get afraid of documentation, but it shouldn’t be something we’re afraid of. It’s something that it should be a mutual conversation.

[00:22:32] Let’s take a quick break to talk about something exciting, the Sales Revolution Network.

[00:22:38] Let’s face it, there are plenty of groups and networks out there, but this one, it’s all about keeping things simple and impactful. Through our vibrant global WhatsApp community, sales professionals like you can come together to share insights, tips, and success stories to support each other. Inspire ethical practices and build a network based on trust and integrity.

[00:23:01] This isn’t just another group, it’s a movement. Find out more@femaleleader.com. Huge biggest hit ever. Get your team to also document during the process, but also follow up with you. And I haven’t done this properly yet, but I will moving forward. What did you hear from that one-to-one? Because let’s talk about feedback.

[00:23:26] Because as a sales leader, you are having to give feedback. When we talked before, you talked about being a listening ear and then sometimes giving them a swift kick in the rear, right? Sometimes we are having to be quite direct and give some feedback. That’s not easy to hear, and I think it’s quite interesting to have your team also feedback.

[00:23:45] What did they take away from that one-to-one? Did they actually listen to what you told them? Mm-hmm. Or did they only hear the negative? Which can happen because to your point about humans and psychology and behavior, sometimes I do that. I’ll go, everything was terrible because I only hear the negative, which is not true.

[00:24:03] There was loads of positive in there. Ask them to repeat back what they heard. ’cause if there are missing bits, you can help be like, well, hang on, we talked about that too. And also get them to send you what their actions are. That’s vital. What are you, what are you gonna do from that one to one, not just have it?

[00:24:20] Well, no different than a sales call. Right. You should start every conversation with an upfront con. I am big on Sandler sales methodology. You should start every conversation with an upfront contract and every conversation with next steps. Why? Why wouldn’t we do the same thing with one-on-ones?

[00:24:35] So easy.

[00:24:36] Take ownership of it. Take ownership. So easy to forget the simple things as well. Yeah. Go back to the simple things. I’d say like even you talked about delegation at the beginning, Casey, and we did a coaching course, uh, this week actually the leadership team, and we’ve been working together for years.

[00:24:52] We’re all, you know, we’ve got loads of experience across the team and we did a course on delegation, but if you looked at the topic, you’d be like. Honestly, we’re quite senior. Why are we doing delegation? And we revisited the Eisenhower matrix, which I’m sure you know, right? Are. And do you know what blew my mind?

[00:25:09] Get a piece of paper

[00:25:09] and fold it in quarters.

[00:25:11] It’s so silly. Yeah. Because I’m like looking at this going, oh my God. Well, those things that I thought was so important and urgent are not. So again, I would say another tip for anyone in sales leadership is like revisit the basics all the time. Like you said, contracting, uh, how you deliver information.

[00:25:29] Like yeah, how you plan your week. Blocking in your diary, how you delegate. Well, because you’ll find when you’re stressed and you’re working at pace, you’ll just forget things that are just so simple. Yeah, absolutely. So I’d really love to dig into the motivations of salespeople, because you’re talking a lot about how do you manage people, how do you get the most out of people, especially without.

[00:25:55] Micromanaging and also them avoiding burnout. ’cause that is very prevalent in our, in our field. Um, and I’ve certainly seen, definitely with the people I’ve managed throughout my career is like, actually the large majority are not motivated by money, which can make it harder. You’re like, okay, so what are you motivated by?

[00:26:14] Mm-hmm. So what is your tips for helping to uncover intrinsic motivators on your team and then helping design. Rituals practices that help them avoid burnout?

[00:26:26] Yeah, so I actually have a free resource that I put together for people on this topic, and it has actual questions that leaders can ask their employees in a one-on-one setting, because nine times outta 10, especially if you’re working with someone who is attached to a revenue team or to sales, if you ask them outright the question of What are you motivated by, they will tell you money.

[00:26:47] Um. So step number one is don’t take that answer at face value and follow up with another question that’s something along the lines of, what does money mean to you? Right? Is it a new house? Is it security? Is it freedom? Is it the ability to do what I wanna do? Right? Um, and the other thing is. If money were completely cared for, what would drive you to keep going?

[00:27:22] If money were handled, you are doing great. What? What would actually make you wanna get up in the morning and keep coming to this job and wanting to continue going? Because that’s gonna happen too. And that’s very real when you find people. That maybe land on that one golden egg early in the year and they just kind of start coasting the rest of the year, which is not, I mean, which is fine, but I’ve been in that position as that rep, and by the way, that’s, that’s only fulfilling to a point.

[00:27:59] And then you’re like, I’m bored. Exactly. Right. So that’s not great either. So I think it’s, the biggest tip I would say is don’t take the initial answer at face value. Just ask. One to two more questions that are open-ended about that. Tell me more about that and write it down. Oh, so you wanna buy a house.

[00:28:18] Tell me more about the, your dream house. Let’s talk about that. Or if I could, if you had the ability to be, if money were handled and you had the ability to either be speaking in front of our team and teaching them how you became successful or, um. Being called out and recognized for your accomplishments, what would, what would you say some, you know, and that gets into, that, gets you into, are you driven by recognition or by helping to, uh, helping other people?

[00:28:52] Go ahead. Sorry.

[00:28:53] No, not at all. I, I’m excited ’cause I’m like, oh, what’s the, what’s, what have you heard the most? What do you find? Because I’ve got an idea in my head from, yeah, the people drawn to sales, but what do they tend to say outside of money?

[00:29:07] Autonomy.

[00:29:08] Autonomy. Okay.

[00:29:10] Um, I’ve heard a lot of autonomy and recognition.

[00:29:13] Those would be the two. Yeah. Um, autonomy, meaning I get to do whatever the heck I want and I don’t have people breathing down my neck. Right. I, I, that’s what that means usually. Right. And the second one being, um, being celebrated for doing well. Caring more about, and, and another way you can frame this is do you get more excited?

[00:29:35] By knowing exactly how much money you’re gonna make from closing that big deal, or by seeing your name at the top of the leaderboard. Mm-hmm. And if it’s by seeing your name at the top of the leaderboard or both, that means that recognition is in there too, as a motive. Absolutely.

[00:29:50] It’s such an anyone who is treading into sales leadership also get your teams to do like personality assessments.

[00:29:57] I did that. Oh yeah. And it’s so interesting. Which one did you do? Oh, was it Myers Briggs, I think. Okay. And immediately, yeah. And they give such detail on strengths, weaknesses. Uh, where they wanna develop as well, what personality types. And sometimes you might find you have two of the same people on your team, which can be easy to manage ’cause they’re similar, but also challenging in other ways.

[00:30:19] So. Yeah. Again, when you are, when you’re taking on leadership, like park, actually review yourself again. I would say like really deeply understand yourself and your strengths and attributes, and also your weaknesses. Like be vulnerable, be honest with your team as well about how you like to work, what’s important to you, but also dig into that with them as well.

[00:30:40] Um, motivators. I remember managing a guy. Who he was very clear. I do not wanna be celebrated and I do not want validation. And it was so unique for me. I was like, what do you mean you don’t wanna be celebrated? And he won a massive deal and he literally sent me a message, do not put this in the shout outs chat, but that, that wasn’t important to him.

[00:31:03] But thankfully he was self-aware enough to tell you that and brave enough to say so. I mean, that’s great. I love that. Um, yeah. Yeah. It’s interesting. On the personalities thing, we always, um, the two that we did most often were DISC and um, StrengthsFinder. Mm-hmm. And the thing that’s really nice about both of those is they’re helpful also with hiring.

[00:31:25] So if you do that assessment with your team and you find that you have a lot of people who have. Very similar thinking styles. That’s not necessarily a good thing because it’ll oftentimes result in group think and you won’t have very productive conversations. You want everybody to be a little bit different in the room and just because again, you’re all in the same role doesn’t mean you all have the same personality type and that you all think the exact same approach, situations the same.

[00:31:51] So it can also be really helpful there, um, when you’re trying to bring on new, new people. Like what kind of. Persona and thinking style do I need for my team?

[00:32:01] It’s really fun as well. I really like it. Oh, it’s also, it’s also also

[00:32:04] so fun.

[00:32:05] Also, it’s a fun, like offsite as well. Get your team together and like really, I, I, everyone winds me up in my business.

[00:32:11] ’cause I always do awkward like. Like icebreakers, but I make them awkward on purpose and they’re not, not always about work, but it’s hell. Like they’ll always be like, oh, here comes Lauren again. But we’ve learned so much about each other and it’s hilarious some of the stuff that comes out. So

[00:32:26] what was your icebreaker question?

[00:32:28] What’s your favorite icebreaker question? Oh

[00:32:29] God. The one I did the other day was, um, what’s something that you are weirdly passionate about that people wouldn’t expect? Mm. It was a good one. It was good. Some random stuff came up. I’m telling you that right now.

[00:32:42] What and what would be yours now?

[00:32:45] I’m

[00:32:45] curious to know what would be yours?

[00:32:47] Mine was tattoos. I actually don’t have it. No, I’ve got one. I don’t have many tattoos, but I love, I’m so obsessed with them. In another life, Casey, I would’ve had sleeves for sure. Is it the permanence? I think it’s the art that it’s scary. The art of it. The art, but, but what scares you about, why don’t you, the permanence, the permanent, it’s the permanence too.

[00:33:08] Yeah. I, I changed my mind like, like the wind. Yeah. No, and I’m too impression where I’ll be like, yeah, I’ll get it. And then next week I’d hate it, so,

[00:33:16] oh, there you go. Okay. I am oddly very passionate. This comes from my mom. I’m oddly very passionate about thrifting and antiques. Love that. And love a flea market.

[00:33:27] Love a flea market. I need to find a good flea market in New York. So if you can recommend any, please let me know. Um.

[00:33:35] I used to watch this TV show called Flea Market Flip, and they went to one in upstate New York and I think they did one in Manhattan too. I’ll Google it later. There’ll be some good ones in upstate.

[00:33:43] Alright, I’m gonna spin on to the quickfire questions, Casey. Okay. This has been amazing and I’ll say it again. Sales leadership is tough, but it’s also fun. And make sure that if that’s something of interest, you like, set yourself up for success. Casey is someone that does coaching and enablement and upskilling.

[00:34:04] You will have to learn on the job all the time because it is, it’s, I’ve learned more in the last year than I’ve ever learned in, in my career. It’s so transformative. Yes. Um, so I would always say, get yourself a coach. Get yourself an amazing network. Meeting women like you. I’m so lucky on this podcast.

[00:34:23] ’cause sometimes I’m like reaching out, like, can someone help me with this question? Find that tribe to help you through it as well. So the questions I’ve got, they’re all centered around sales leadership. The first one is, what trait do you believe is most critical for a sales leader today?

[00:34:42] Um, I would. I would, I would say, um, the ability to read the room, and I’m not gonna label that as empathy, although I do, I mean, I preach that and I think it’s very important, but it’s also understanding how you need to show up and what that other person needs from you in that moment.

[00:35:08] I think that’s actually more important than empathizing with another person.

[00:35:12] Would you say that’s kind of a spinoff of eq? Yeah, absolutely.

[00:35:18] I think it’s, I think it’s a very specific part of eq, emotional intelligence.

[00:35:24] Mm. And it’s such a big one when you’re so used to working for yourself and only having to worry about yourself to then start thinking about that.

[00:35:30] That’s not one Ive heard before,

[00:35:32] but I think, but I, yeah, but I think if you’re really a really great, effective consultative sales person, you’re probably actually pretty good at that. And you don’t realize it. You just have to apply it to a new situation. Mm-hmm. Because really great salespeople. Know how to do exactly that with their customers.

[00:35:47] And now you just need to do it with, you know, directly internal. Yeah, absolutely. It’s still customers, right? If you’re still in a customer facing role.

[00:35:55] Well, I always say in sales, you are, you’re not just selling externally, you’re also selling internally. And that massively means your team, because your team have to be on board with your vision emission.

[00:36:04] So you’re, you’re having to sell them on onto that journey with you, otherwise they’re not gonna wanna work for you. That’s right. Um. What about inspirational figures? And by this I mean female sales leaders, mentors that have inspired you on your journey.

[00:36:19] Hmm. Um, the person that come, oh gosh. I actually am really fortunate that I have a lot of women mostly, uh, that I would put in this category mostly because I have surrounded myself with a lot of women sales leaders throughout my career.

[00:36:39] So I have a few I’m going to give you, I love ’em. Send them, I’ll put

[00:36:44] the links to their LinkedIns or any recent websites, businesses afterwards to send that to me if you can.

[00:36:50] Um, one would be, um, Nina Kovac, my former a VP at Salesforce. She would be one. Um, she is just like, totally, I’m still very much in touch with her and she is.

[00:37:08] The epitome of a human first sales leader. Um, I have a group of former sales leaders that I, that are now all entrepreneurs that I talk with very regularly. That would be Mel Goodman. She started a company called Work Mom. She’s also ex Salesforce, my friend, uh, Donna Lynn. Who is also, she now has on target learnings.

[00:37:39] You should actually talk to her for your podcast. She does similar things to what I do. She does sales leader training and then Lindsay fine of fine fractionals. She does fractional revenue consulting now. Um, I talk to them very regularly. Um, and then I can mention others that like I came up the ranks with at Salesforce too, that are coming to mind most immediately are Michelle Cochran.

[00:38:05] Um, um, Michelle Caruso, um. Yeah. Sam Buller. Rachel Loder. Gosh, I could go on.

[00:38:15] Well, this is amazing. Are you, is this

[00:38:16] gonna be like on the Oscar Oscars where you’re like,

[00:38:19] and I wanna play Well, what an amazing place and privilege to have worked at a business with such awesome women. I mean, sometimes Casey, I have guests struggle to give me one.

[00:38:32] How lucky are you? I feel very

[00:38:34] fortunate.

[00:38:34] So fortunate. And it wasn’t always that way. Yeah, and I’ll definitely be adding all of you ladies so I can follow your journeys. ’cause every time I hear these names and you follow people, you’re inspired by what they’re doing. So yeah, I mean that’s, that’s awesome.

[00:38:49] Thank you for sharing them. Um, and then finally, um, upskilling, right, reading or listening to things, what’s really influenced your approach to sales, leadership? Anything you’ve read, for example.

[00:39:03] Uh, I have two books that were my most favorite leadership books. Number one is Multipliers by Liz Wiseman. You have you won that one?

[00:39:15] I haven’t go by it. I mean, it’s so good. Um, and the second one is, um, hidden Potential by Adam Grant. Those two

[00:39:25] far none. My list is getting too long. Casey. I never have enough time. No, but listen to them. Oh, the other thing actually, a guest gave me a tip for, um, that you might quite like, you might have done it in your career that I love and I’ve just started doing internally at my business, is a book club.

[00:39:42] There are all these amazing books on leadership and maybe just, yeah. One of the books is, could be for SDRs, outbound selling. So I’ve actually done one on EQ for my team. Love it. And I’ve sent them all a copy and we are all gonna come together at the end of the month and talk about what we learn. It’s such a

[00:40:00] great thing.

[00:40:01] Okay. I totally used to do a book club with my team. Nice. Can I tell you my favorite book club that I used to run with my team? Yeah, you can. And I want you to use this too. Um, seeing the Big Picture by Kevin Cope. Seeing the Big Picture by Kevin Cope, Kevin Cope. Awesome. It is all about understanding. This is a book club that I think every B2B sales leader should do with their sales teams because it’s a book that’s all about feeling.

[00:40:28] If you want your team to get really good at feeling confident in talking to CFOs, actually wrote a post online about this recently. That’s what this is about. What do they care about when it comes to terms like a balance sheet and profit margins and all of those things when it comes to understanding how to talk to CEOs, CFOs, executives?

[00:40:49] This is the book, and I used to structure it where I would put together a giant Google Slides document and I would divide it up chapter by chapter. It’s, I believe it’s enough chapters that every person on my. Nine person team could handle a chapter and they were in charge of week by week coming to the team meeting and spending the first 15 minutes, everybody had to read that chapter and that person from the team had to build a slide teaching the team about that specific chapter, like what are the key takeaways?

[00:41:19] And then when we were done, everybody had a shared slide deck of all the key points that they learned in the book. It was great.

[00:41:25] That’s awesome. It’s, yeah, it’s a great way to bring people together, have fun. And made me think executive engagement, that’s a topic in itself because it is, it’s huge. It the language, the way that you hold calls.

[00:41:40] I mean, I just had a call with an executive and his words were, Lauren, I don’t speak to any other media owner, but you. And he’s like the CEO, so like, let’s make this a good one. And it’s very different the way you handle those types of calls. And it ended up being a super fruitful conversation and I feel lucky he wants to still speak to me.

[00:41:59] But, um, yeah. Anyways, such amazing tips here. You are wonderful. I’m so glad we met. I’m so grateful to have you as a guest. You’re doing some awesome things, um, especially yeah. Supporting women. So thank you so much, Casey. It’s been a pleasure. Of course. Appreciate you, Lauren. Thanks for having me. Thanks for listening to the WISE podcast.

[00:42:22] I have been your host, Lauren Palmer, and if you’ve enjoyed this episode, please leave us a review or why not join our sales revolution. For more details, please visit female leader.com. See you next time.