Selling doesn’t have to be a grind—in fact it can be a joyful opportunity to help your ideal clients and buyers achieve their vision. That’s the refreshing viewpoint of sales maven and Win Without Pitching leader Shannyn Lee.

We explore:

How to take control of conversations around fees and value (hint: you may need to kick some old baggage to the curb).

Developing selling frameworks that define how you’ll respond in each stage of your buyer’s journey (including how you’ll vet them).

Why you want to be “kind but ruthless” (and exactly what that looks like).

The surprising role joy can play in your selling and marketing efforts.

Using LinkedIn to engage future clients and build relationships—and one winning way to turn “cold” into warm.

LINKS

Shannyn Lee | Website | YouTube | LinkedIn

Rochelle Moulton Email List | LinkedIn | Twitter | Instagram

GUEST BIO

Shannyn Lee is the Managing Director for Win Without Pitching and an unstoppable force of human empowerment.

She spent a decade in senior marketing and communication roles in Fortune 500 companies before moving to a business development leadership role at a well-regarded Seattle design firm. She also spent four years at Catapult New Business where she worked with agencies of various disciplines and size, building and leading their business development programs.

Her time on the front lines of agency business development coupled with many informative years on the client side, has given Shannyn a unique perspective into what marketers are looking for in agencies and what agencies must be doing in order to compete and win.

Shannyn’s empathetic and encouraging coaching skills have helped her clients translate the lofty Win Without Pitching ideals into real behavioral change with lasting results.

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TRANSCRIPT 

00:01 – 00:31

Shannyn Lee: Pick the 1 thing that you enjoy doing. Maybe it’s writing, maybe it’s a podcast, maybe it’s videos on a YouTube channel, and go all in on it and do it well, and then leverage that content to turn it into other things. So you might write an article that you then chunk up and use for LinkedIn posts or tweets, right? But you’re 1 person, you can only do so much. So you need to get disciplined about what’s the 1 thing you’re going to be good at. And you need to block it on your calendar, 1 hour a

00:31 – 00:42

Shannyn Lee: day, 3 days a week, that’s non-negotiable unless the house is burning down. And then you need to have some fun with it, frankly, so that you keep doing it and find some source of joy and inspiration in it.

00:47 – 01:16

Rochelle Moulton: Hello, hello. Welcome to Soloist Women, where we’re all about turning your expertise into wealth and impact. I’m Rochelle Moulton, and today I’m here with Shannon Lee, who is the managing director for Win Without Pitching, and I quote, an unstoppable force of human empowerment. And having seen her in action, I can attest. She’s also a salesmaven with off the chart empathy and encouragement skills. So Shannon, welcome.

01:16 – 01:20

Shannyn Lee: Thank you so much, Rochelle. I’m so excited to be here with

01:20 – 01:51

Rochelle Moulton: you. Well that makes 2 of us. 1 of the reasons I’m really excited is because you’ve got such a rich and varied set of experiences in B2B conceptual sales that I think will be hugely helpful to our audience. But you also have a point of view around sales that I’d love to dial into. So let’s dive in. Sounds good. And I’d like to start with your story. Now you’re clearly not a soloist and yet I couldn’t wait to have you on the show after we spent just a little bit of time together. So tell us some

01:51 – 01:56

Rochelle Moulton: more about how you got to this place and your role today with Win Without Pitching.

01:57 – 02:30

Shannyn Lee: Yeah, you bet. Whenever I look back on my journey, I think there are just key moments along the way that I think, well, did it get me here or not? But what I have come to realize is there’s some varied experience that has allowed me to just step into who I am and be really comfortable with that and really try to help others in these moments, specifically now around selling. And so I’m a big fan of varied experience. And so professionally, I started on the corporate side and worked for some of the biggest companies in the

02:30 – 03:02

Shannyn Lee: world, AT&T Wireless, for example. And I was thick in the politics of what that means to work for a big organization and navigating my way through. And I learned I liked a smaller opportunity and jumped over to the design agency side of the business, where I worked for small firms that built brands and designed annual reports. And that’s where I landed in my first sales role. And when the opportunity was presented to me, I really had no idea what it meant to sell for a design agency. But I just was brave and said, yeah, I want

03:02 – 03:32

Shannyn Lee: to do it because I want to be around creative people. I want to make an impact. And I really took to it and really found that it was a superpower for me. And I was fortunate enough at that agency to meet Blair Enns, who’s the founder of Win Without Pitching, because we had him come in and teach us how to sell the Win Without Pitching way. And it was in that moment that I realized kind of how much of myself I had lost on the big corporate giant side, and how much permission he was giving me

03:32 – 03:38

Shannyn Lee: in that moment to sell from a place of help and empathy and creating value.

03:39 – 03:40

Rochelle Moulton: Imagine that.

03:40 – 04:09

Shannyn Lee: Yeah, right. Be yourself and see if you can help. And it just took off from there. We stayed in close touch. He was a mentor and he asked me about 9 or 10 years ago to join as a coach. And I’ve been doing this for all of those years and now moving into a leadership role in January where I’m taking over day-to-day operations of the company. So it’s just been a great ride. It’s been filled with some ups and downs, like everybody goes through, but I really feel like I’m working in my unique ability and helping

04:09 – 04:10

Shannyn Lee: people.

04:11 – 04:26

Rochelle Moulton: And I just love the trajectory of this because it’s, you know, big corporate and then you start to find your way. And then you just find that place where I call it your genius zone, where you’re firing on all cylinders and doing the work that you were meant to do.

04:27 – 04:37

Shannyn Lee: Yeah. And it feels good to Allow yourself permission to find that and then find the right company that sees that. And man, it’s just unstoppable if you can get there.

04:37 – 04:39

Rochelle Moulton: Yes, when you get there.

04:39 – 04:41

Shannyn Lee: When you get there. Not if, you’re right.

04:43 – 05:01

Rochelle Moulton: So Shannon, there are a few things about selling that I’d really like to 0 in on. So I guess the thing I’d kind of like to start with is why do so many of us have such a hard time selling ourselves? I mean, because as soloists, that is what we do. I mean, we’re mostly selling our expertise and ourselves.

05:02 – 05:39

Shannyn Lee: Yeah. A couple things come to mind for me. The first is, I think, so many of us equate selling with something icky and pushy and feeling like we were being duped, right? Like being convinced of something. And so I think that’s the first thing is people’s baggage or perceptions that they bring to selling service roadblocks. The other piece of it is, I think a lot of times people struggle with how to communicate who they help and how and what the value is they think they can create for that client. And I’m talking about positioning there and

05:39 – 05:49

Shannyn Lee: you know very well how important that is. So I think those things combined oftentimes crash and people just can’t overcome them. And that’s where the hangups can be.

05:50 – 05:56

Rochelle Moulton: Do you think as women, do we have a harder time with this than men do just on average?

05:57 – 06:14

Shannyn Lee: Yeah. And I wish the answer was no, but I think it’s, I know it is completely possible to overcome and be quite effective and quite helpful as a woman in the sales environment. I think there’s some additional things we have to overcome as women for sure.

06:14 – 06:43

Rochelle Moulton: You know, it’s interesting because I thought 1 of my superpowers back when I was in a big firm was that I was empathetic and I would listen because I didn’t think of myself as a power seller, which sometimes people would look at it that way. And I found that leaning into my natural personality, which wasn’t soft, but wasn’t hard either, it felt like I was bucking the system, but it worked for me.

06:43 – 07:22

Shannyn Lee: Yes. And so What I love about that is you were uniquely okay with being you and not trying to step into a role or turning into a sales robot because you felt there was some way that this had to be done. But you let that true you come out and use those strengths and superpowers to help you guide those conversations. And selling should come from a place of empathy. Selling should be about having conversations and uncovering, can I help? And there are vulnerable moments on either side of the equation, and you should be yourself and figure

07:22 – 07:31

Shannyn Lee: out what is it about you that really matters in those conversations so that that person across the table can see you in a true manner.

07:31 – 07:51

Rochelle Moulton: I love that. Well, and the irony, feel free to tell me if you disagree, but the irony strikes me that it’s actually easier to do that as a soloist than it is inside an organization where there is a model for how to sell versus you create your own around your unique strengths and your vision for the work you’re doing?

07:51 – 08:17

Shannyn Lee: Yeah, I agree. And I would think so. And I think that the soloists that I’ve worked with at Win Without Pitching eventually get there once they’re given permission. And I think a lot of times the soloist entrepreneur has a lot of pressure on them because they have to play every role in their business. And that can be where things get challenging and where things might feel harder than they need to.

08:18 – 08:48

Rochelle Moulton: Yeah. 1 man band or 1 woman band in this case. Right. So let’s meander over into this idea of how we can do a better job talking about money, about our fees, like giving a big ass number to something and not choking when you’ve said it. I’ve done that a couple of times. It seems like we spend a lot of time getting in our own way around these fee conversations. What do you think about all this?

08:48 – 09:22

Shannyn Lee: Well, I think it starts with understanding your motivators that cause you to do those things in the sale, like the inability to talk about money. Why is it hard for you? I think you have to examine those motivators. And those motivators could be things like you have a high affiliation score, which means you have the need to be liked and you have the need to create comfort and make things easy for people in these conversations. So you seek to kind of ease the tension versus bring a healthy tension to these sales conversations. So I think once

09:22 – 09:41

Shannyn Lee: you can identify like, what are my motivators? Why does it feel uncomfortable to talk about money and name it and explore it? And then frankly, like flick it off into the universe and get yourself in the right mindset. That’s the beginning to this journey of gaining confidence around talking about money.

09:41 – 09:49

Rochelle Moulton: Well, talk some more about healthy tension. I totally agree with that. I can feel it in a meeting. You can describe what that looks like for people.

09:49 – 10:26

Shannyn Lee: Yeah, what that looks like, for example, in an initial sales conversation that we call the qualifying conversation, just like many do out there, is your ability to demonstrate some selectivity. You should be equally as selective as that person looking to hire you is when they’re assessing the right fit. And so when you get into a sales conversation, you should feel very empowered to take charge from the get-go and let that person know, hey, I also have a process when it comes to deciding who’s a good fit for me and my expertise. And so I’m gonna ask

10:26 – 10:56

Shannyn Lee: you a bunch of questions on this call to assess, is there a fit? And if we decide, yeah, at the end, this makes sense, then we’ll keep talking and we’ll schedule the next conversation, which will be largely around what’s the value that we think we can create for your organization working together. We’ll identify metrics. What’s happening is here is from the beginning, you’re taking control of that conversation and letting that person know, hey, I’m checking you out just as much as you’re checking me out because I’m most interested in seeing if I can help you. And

10:56 – 10:59

Shannyn Lee: if I can’t, I’m going to be really honest and let you know upfront.

11:00 – 11:36

Rochelle Moulton: Yeah, taking the reins from the very beginning. And I think it’s not always natural when somebody first starts a solo business because usually they’ve come from being an employee somewhere else. And this idea that you have a process, not just of who you’re going to work with, but how you’re going to work. Just taking the reins from the beginning while still engaging the client and getting them to talk about their challenges and their environment, all of those. It feels like those are confidence builders. I almost felt myself sit up straighter as I thought about handling a

11:36 – 11:37

Rochelle Moulton: meeting that way.

11:37 – 12:07

Shannyn Lee: Well, and I know I sit up straighter when I handle my sales calls that way, because you’re right, I feel confident. And part of why I feel confident is because I have frameworks to follow that tell me what I need to do in each conversation throughout the buyer’s journey. So I’m organized and I’m clear and I don’t feel like I’m making it up each time I have a new sales conversation. So that’s the other piece of it is adopting some selling frameworks for yourself to get yourself organized around this journey you’re about to go through as

12:07 – 12:11

Shannyn Lee: you’re working with a potential buyer to decide if, you know, you’re gonna do this together or not.

12:11 – 12:24

Rochelle Moulton: Well, let’s dig into that. That’s just too juicy to ignore. So when you say selling frameworks, it sounded like you were talking about the conversation. So we’re talking about the conversations versus the process, the entire sales process.

12:25 – 12:58

Shannyn Lee: Yeah. So we think about things in terms of the buyer’s journey and What are the things that need to get done during the buyer’s journey to help decide are they a fit, should we work together? And so for us, it starts with this idea of what we call the probative conversation, which is this is positioning, essentially. This is there through your thought leadership or through referrals, people are hearing about you. You aren’t necessarily present. They’re forming an opinion about you, maybe stuff you’re posting on LinkedIn, and they see you as an expert. And they raise their

12:58 – 13:37

Shannyn Lee: hand and say, I want some help. And then the first kind of in-person or via Zoom conversation happens where you qualify. That’s the next framework is the qualifying framework, vetting to see if an opportunity exists if the fit is good. If it is, you proceed to what we call the value conversation. And the value conversation is all about bringing transparency to metrics, measurements, needs, but more importantly wants, like what’s the future vision? How do we get there? What do we think we can be accountable for as the solopreneur to contribute to that vision? What do we

13:37 – 14:13

Shannyn Lee: think together a fair range of investment is to get this work done? And okay, now you’re collecting all this information. And that means you can then go away and create a proposal. And in When Without Pitching Land, we like a 1 page 3 option proposal. We don’t want a big long daunting document. We want 3 high level ideas for different ways you can work together within a budget range that was agreed upon. And then you come into a closing meeting, but it’s more about facilitating a choice and really saying, okay, we’ve arrived at this place where

14:13 – 14:34

Shannyn Lee: we know enough about each other and enough about the project and enough about what the right investment is that it’s time to decide. I’ve got 3 options, which 1 makes the most sense for you. So it’s following these frameworks, these 4 conversations to help guide this journey and be effective, but be efficient. So it’s not a long drawn out sales process.

14:35 – 14:51

Rochelle Moulton: You know, 1 of the things I love about the way you just framed that is the value conversation. And I have the advantage of having heard Blair just talk about this in the last month. It sounds way less intimidating, the way that you just described it than I think people think about it.

14:51 – 15:23

Shannyn Lee: Yeah, I think what it really brings is integrity and transparency, honestly, because you’re demystifying how you price things. You’re putting it all on the table for the client to say, these are the things that need to be true at the end of our engagement. These are the metrics that matter to me most. And you’re sitting across the table saying, these are things I feel like I can hit. I’m going to think about solutions to do that. This is what I think the value is that can be...