Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AEs about things like, what does it take to be a great sales manager? Or how can you go home happy month after month? So let's dive right in. 

Hi everyone, you're listening to “On the Flip Side” with Wingman. I'm Kushal. And today's show is dedicated to all things women power. I'm so excited to learn more from our guest for today's show, Dr. Cindy McGovern. Dr. Cindy is the CEO of Orange Leaf Consulting, which specializes in helping companies grow their business through assessment, planning, training, execution and measurement. She's also a passionate public speaker, and loves to present new ideas and sales strategy, person development and leadership. Dr. Cindy, so great to have you on the show.

Dr. Cindy: It's so wonderful to be here. Thank you so much for having me

Kushal: So Dr. Cindy just to start off, I love your LinkedIn bio that reads the first lady of sales. How did you come up with that one?

Dr. Cindy: I think I can take credit for it actually. I wish I knew who actually said it first, because it was very early on in my sales career. And oftentimes, I was the only woman presenting and so they would say, oh, here comes this lady, here comes this little lady. And somebody says little lady, she's more like the First Lady. And I was like, Oh, I'm totally taking that. I'm stealing that. So whoever's listening, if you came up with that, I would love to be able to give you credit.

Kushal: Nice, incredible. I think now, of course, as this is a woman's in sales special, of course, I'm just gonna get straight to it. As a woman in sales really and also as a CEO running her own business how has your journey been? And what are the challenges really that you faced as a woman in sales?

Dr. Cindy: So it's a great question. And it's sort of twofold. I've had sort of my own challenges within my own head that I've had to combat. And then of course, external challenges of competing against not just, you know, other salespeople, but just my own demons of like, I have to be the best, and I have to beat the guys or I have to beat these other ladies. So I think part of our competitive nature as salespeople is, is healthy. But I think we also probably push ourselves a little bit too hard sometimes. And I think for me, it was also owning my value. And knowing what I brought to the table, and that was sort of that internal struggle of like, well, I have to gain permission to ask for the business, or I need to get to this point in the relationship before I feel like I can do this. And that's not true. You know, that's the advice that I would give anybody listening is you've earned the right if they're meeting with you, if this prospect's meeting with you, you absolutely have the right to do that. But there were these sort of inner voices in my head going, you didn't earn it yet. You didn't earn it yet. So that was one of my bigger challenges. 

And then the other challenge is comparing myself to those other salespeople. And I think there's a healthy level of competition that comes with that, where you can say, they're doing this really well. And I'm gonna kick butt and do this too. But I think you look externally too much, it actually affects your confidence. And so it's sort of that journey of saying, okay, this is a healthy amount of competition, this is a good way to look at it. I'm learning from that. I think that's a motivator for me to be like that, I can hit that number, but also being really careful that you're not judging yourself.

Kushal: I love those insights really about, you know, the inner voices. I think, not a lot, not enough of us really talk about it enough, right. Forget about external forces. But really, the own voices inside our own heads are sometimes the ones that are really that, especially if you're a woman, right, and this is really the most toughest to even drown out. So I think it's really, I think it's really key to sort of address those pieces. So to go back a little bit, what do you really wish that you first that you kind of knew when you first started out with all of this?

Dr. Cindy: So my journey was kind of interesting into sales, because I never wanted to be in sales, and now known as the First Lady sales, go figure that one out, right. Like, it's kind of a crazy thing. But when I got pushed into sales, it was because I thought it was this icky thing, I thought it was the pushy type of sales, the transactional type of sales versus really relationship selling, which is true sales. It's very consultative and it's helping other people get what they want. So at the beginning, I wish somebody had told me that that was just the very small portion of stakeholders that that pushy side, that sales truly is understanding needs, delivering on those needs, if you can. And so that was the first thing that I would have changed. And then the second thing that I would really change, if somebody would have shared with me to go back is to remember that I have value whether they see it or not, doesn't matter if I may not be a solution for you today, I may not ever be a solution for you, but that does not diminish the value that I provide to my clients.

Kushal: I think those are really super key things. And I was actually watching your highlight reel where you're talking about, you know, the icky sort of image and impression that a lot of us have of sales. How do you really drive people to go beyond it, people who are sort of younger at their careers maybe?

Dr. Cindy: It's funny because I think even seasoned sales people struggle with the ick factor sometimes, because we feel like we're stalking a prospect or we're following up too frequently. And so we get in our own heads around, I'm being that person or that kind of sales rep. No, you're not. If you really believe that you have a solution for them, stay in front of them and help them. But for folks who are starting their careers here or younger in sales, I will tell you to recognize the fact that you're not going to be that person, because you've already seen it. If you see, and you can recognize the ick factor, you're never going to be it. Because you can already know, okay, that's not where I want to be. And I have kind of an avatar that I use for that. And I call them Tommy two thumbs, and he's this used car salesman coming across the lot at you. And we know that, we don't want to be that. So you're going to rail against it, it's that observation of I don't see myself there. But on the flip side of that is being clear on who you do want to be. And I think the advice that I would give you is to own the talents that you bring to the table. But on your curiosity, own, you know, women in particular have this wonderful little voice in our heads, that also pushes us and we have really good intuition, use all of those things to your advantage in sales, to be able to listen to what's being said, as well as what's not being said by the prospect and client.

Kushal: So Dr. Cindy, I'm assuming that a lot of these values really have made their way into Orange Leaf Consulting. But I'd love to maybe hear a little bit more about you know, the how and why we Orange Leaf Consulting, how did it all begin?

Dr. Cindy: So I wanted to start a consulting firm that truly consulted. We have a very high turnover rate with clients on purpose. We want to be able to go in and fix it and get the heck out of dodge and leave your leadership in a position that they can actually continue to do this long after. And so where it began from is I wanted a consulting company that literally did just that. I saw so many consulting companies that we're in with an organization for many years. That's not consulting that's outsourced, that's a different thing. And so what I wanted to do is be able to empower leaders within organizations to be able to grow their own business, because there's leadership structure already in place. But so often as leaders, and I know, even for myself, we maybe weren't trained on coaching or staff, we maybe weren't trained on even training our staff, we were a good sales rep put into a managerial role. Well, there's a lot of skills that we needed to learn and embrace to be able to elevate the people on our teams. And so that's really what we do is we go in, we assess the organization, we put that leadership piece in place, we're very much behind the curtain, we want to make sure that it looks like it's coming from your leadership, and then we leave you stronger than we found you. And that's the whole goal. And then we get out of dodge. And then hopefully you go tell people all the wonderful success stories, but it's really about that true consulting to build them stronger. That was really my vision in starting a company.

Kushal: So Dr. Cindy, you talked about really empowering people to become better leaders in some way, right. I'm assuming you would have seen a lot of women either as being part of that, you know, being in those leadership roles or maybe struggling a little bit to get to those. What would your advice be in general to women who are trying to get into leadership roles today?

Dr. Cindy: My biggest advice to women who want to get into leadership is to raise your hand, there is a seat at the table for you. You just haven't sat down yet. And this is one of the things that in a lot of the women that I coach, a lot of women in transition who are moving into leadership roles, or even entrepreneurs, or women that want to get into sales management or leadership, they struggle with raising their hand, it's like you're waiting for somebody to see your talent. No, no, tell them your talents, sell yourself. It's your personal brand. You're building your personal brand here. And you want to build that profile as the leader. And so if it's something that you want, and that's part of your aspirations and your career, look for the opportunities to self-promote which is hard. Even for salespeople, it's hard. You have to find those opportunities to say, I don't want to do that. I can help with this. Let me show you my skill set. And make sure that you're constantly offering that value that you have. 

And then the other thing I would say too, is recognize the path that you have within the organization that you're in. And if there's not an upward mobility path, maybe that's a closed door and you need to find another path elsewhere and I think women wait too long. A lot of times where we think, well, they'll finally see it, they'll recognize it later. It doesn’t happen. It doesn't happen and believe what they're telling you and showing you if they're promising, you know, oh, it'll happen eventually. But it still isn't happening in 2, 3, 4 years, believe them, because it's not, you know, they believe their actions. And so making sure that you're seeking out those opportunities to find the right path for you and not being afraid to step out of that. And I think, you know, we call it a comfort zone, but I actually don't think it's necessarily comfortable. Sometimes the comfort zone is just familiar, and it's actually really uncomfortable where we're unhappy. And so I would invite all of the women who are listening to this podcast to think about is, are you in this comfort zone, familiar zone because it is just familiar? Is it really fulfilling you? And if it's not recognize why it's not? And maybe that leadership path is the way for you. But just because you don't see a path in your current organization doesn't mean there isn't a path out there.

Kushal: Dr. Cindy, I love how you talk about really the difference between a comfort zone and a familiar zone. I think that is maybe, you know, a lot of us, not just women, but a lot of us probably fall into that trap and think, you know, that's a good place to be when it really in the long term isn't. So statistics and our own experience obviously tells us that a lot of women tend to opt out at some point or the other have new leadership roles, whether that's in sales. And this was in fact a thread that I was having with Shruti, our founder, yesterday or a couple of days ago, when we were talking about how so many women actually just opt out at some point. Why do you think this really happened? And is there a way for corporates really to make it easier for women, or at least give them an equal playing field in that sense?

Dr. Cindy: So, wow, that's a loaded question. So that's a big one.

Kushal: So hope you're having morning coffee? 

Dr. Cindy: Yes, I did. I did. But I think this is such an important thing to discuss. And this is where I think as women leaders, we have not just the opportunity, but the obligation to help the generation behind us. Because we are the ones that are breaking the glass ceiling, we are the ones that are fighting those moments in those inroads and those opportunities to take a step forward and take that seat at the table. But I think a lot of women opt out because number one, they're exhausted from fighting, I really do believe that's true. It's like I've done everything I can, they're still not seeing my value. But that's kind of what I was saying before, it's just because they don't see your value doesn't mean it's not there, examine that comfort zone, that familiar zone, maybe that's your cue to exit. And then the other thing that I think we opt out is because it's by choice, it's truly by choice. And maybe we want to dedicate time to family, maybe we've decided we don't like the way that the organization is run. So those are by choice. 

But I think the one that worries me the most about women opting out of the leadership roles is because they feel like they don't have the opportunity. They feel like it's not that even playing field. And it may not be truly, it may not be we have you know, we have biases as human beings, but recognizing the nature and the culture of the organization that you're in and trying to see those opportunities that align with the goals of the organization, is the way you'll start to sort of chisel away at that glass ceiling, and give yourself permission to do this. And I think that's the thing also is we sort of talk ourselves out of it. So then we opt out, like, oh, you know, I shouldn't do this, I shouldn't push, I shouldn't stop shitting on yourself, you know, let's get really clear about what you want to do and find that focus. And I think sometimes women opt out. Because we don't have a good plan in place, we sort of have an idea of where we want to go, but we're not in tune with the path to get there. Don't be afraid to ask for help to get on that path. Don't be afraid to reach out to colleagues, to mentors to other people within your organization and say I have my sights on that job. How do I get there? How did you get to the job that you're in? Because if we're not gaining information on how to at least take one step, it's really easy just to throw your hands up and say, okay, I give up.

Kushal: I think stop shooting yourself is a really powerful way. There's so many slogans that I see coming out, you know, really printed on T-shirts. And obviously, we're talking about, you know, what is the fact and you're right, I think women men we all the other, we really need to kind of ask for help and ask really for guidance when we feel we need it. And if we were to flip this around a little bit, what would your advice really be to other folks who are really becoming better allies for women, or other diverse backgrounds at the workplace?

Dr. Cindy: I love that question. Look for the opportunities to elevate others, kind of what I think about the next generation, like it's not just an opportunity, it's an obligation that we have. And everyone that is an ally to a woman in the workplace, and finding ways to help them to shine, even if maybe they're not willing to step into that spotlight on their own just yet, but see the talent in them see the value that they're providing to the organization and invite them into the spotlight and find that chance. And there is this whole misconception that like, you know, self-made Millionaires and self-made this, nobody does this life alone, you know, somebody gave you a job at some point, somebody helped you. So for the allies out there, recognize the barriers to entry for the women within your organization look at or even in your industry, you know, maybe it's not even within your company, but it's within your industry, and find ways to weave them into the fabric of the conversation and that strengthens everybody. I mean, obviously we're all much stronger for having a diverse, you know, group at the table. But I think it also makes you look really good as an ally because you're seeking out resources to bring new life into the conversation. So there's a benefit to you as well.

Kushal: So we’re obviously talking about you know, weaving sort of newer voices like you said it to the conversation. What would your advice really be for companies and for corporates who are maybe cognizant of the differences and maybe want to do better?

Dr. Cindy: So there's a lot of companies that we work with actually are, you know, looking for creating a more diverse community, but also making sure that they're elevating each other's talents and strengths and creating space for unique talents even as well. And so my advice would be, take an inventory of your team now and look around the room. And the easiest thing is just look around the room and everybody's your same age, everybody's got your same background, you have a problem. But the next piece is, look at where the gaps are in talent. Because every team needs different skill sets. I mean, you can easily look at, you know, you need operational, you need process, you need sales, you need technology, those are the easy ones. But look at the creativity that is needed to be able to propel the organization forward and start asking, where can we find that? Where can we find the different points that's going to be able to bring that level of talent and that different set of eyes? And I'm a big fan of having an outside set of eyes on everything anyways. But one of the things that you can do is talk about this with a friend in another industry, have them assess your organization, say, Here's my leadership team, what do you see that we need, you know, and just have those conversations. That's a lot of what we do with organizations too. But really just self-analyzing by taking that inventory. It's funny, because sales managers that we'll work with, they'll always say, oh, you know, I'm down a sales rep, I gotta hire a sales rep. And I always say pause, why do you need a sales rep? Is that really what you need? Let's look at the skill set that's missing. Do you need a prospecting rep? Do you need a hunter gatherer? Do you need somebody that's stronger in technology, do you need somebody that's more of a marketing type of a sales rep? Before you go filling a slot just to fill a slot, look at what actually is needed for the next phase of growth, and then make those decisions. I think it's no different from organization looking to bring in a diverse skill set.

Kushal: Dr. Cindy, one of my last few questions for you is really going to be about, you know, what do you think it really takes for a woman or really anyone to succeed in sales?

Dr. Cindy: Wow, big question. I think the first thing that I would say is you got to actually have a really good plan. And it sounds so simple, but we as salespeople are really good at winging stuff. And we've gotten used to it, and especially if you've been in sales for any period of time, and you're selling within a vertical, it is sort of a repetitive thing. They all have similar challenges. They all have said, you know, and I don't know about you guys, but there have been days, when I've had conversation, I'm like, did I already say that? For sales calls back to back and like, did I already explain that? So we have to be really careful about that. But it is having that solid plan of where you want to go and giving yourself permission to create space to plan and get clear on if this then that, if this then that, and know where you want that path to go. And more importantly, also knowing what the markers are along the way that show you that you're leading towards your goals or not. And if you're not, tweak that plan, but that's one of the most important things and so much of what we do with organizations and even individual salespeople that we coach is re-crafting their plan because it was a little loose to begin with. Maybe didn't have some smart goals in there. But also, they started to wing it because they thought they knew what was going to happen next. So in the most simplest answer I can say is, solid plan.

Kushal: That's in fact part of what we already have in our T-shirt. One of our slogans for our company is don't wing it, Wingman it. 

Dr. Cindy: Nice, I love it.

Kushal: I think this conversation has really been, you know, filled with so many insights. It's such amazing ideas, really, for people to kind of learn from, which kind of brings me towards maybe the last question for today, which is really around what is the number one impact that you would like to drive on the world?

Dr. Cindy: My number one impact is to give people permission to go after what they want. That's literally I think sales is a life skill, not a business skill. I think it should have been taught in high school because it's about going after what you want and helping other people in the process. And so if there's one big impact, it's to give yourself permission. You deserve it. Go get what you want.

Kushal: Thank you so much, Dr. Cindy. It's been really amazing. You're having, you know, having you “On the Flip Side” with me. Appreciate your time today. 

Dr. Cindy: Thank you so much. It's been a pleasure.