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Creating Value & Trust Through Messaging w/ Kristina McMillan {Hey Salespeople Podcast}

In this episode of the Hey Salespeople podcast, Jeremey Donovan, SalesLoft’s VP of Sales Strategy and Kristina McMillan, VP of Research at TOPO, dive into what it means to create credibility as a salesperson through messaging.

At TOPO, Kristina makes it her mission to help sales organizations deliver the best experiences possible to their buyers. As the Vice President of Research, Kristina has a team of analysts who combine strategy with actionable best practices for some of the world’s fastest growing companies. Kristina shares some of these best practices with Jeremey, including how she thinks coaching is starting to see a resurgence thanks to conversational intelligence tools and what types of messaging resonate with people in a way that the seller is actually giving some value. 

This episode covers the important do’s and don’ts of messaging for salespeople to establish trust with buyers.  You won’t want to miss Kristina’s three crucial steps for a successful business conversation. 

Listen to this episode for answers questions like:

  • How can salespeople hone their craft as storytellers? 
  • What are the three steps for achieving meaningful messaging? 
  • How did Kristina learn to communicate with C-level executives as a new SDR?
  • What does it take to turn a prospect into a customer? (Hint: A little empathy goes a long way.)


Partial transcription:

Jeremey: Welcome Kristina McMillan from TOPO. Kristina. Welcome. 

Kristina: Thank you.

Jeremey: Kristina and I shared the stage at Rainmaker earlier this year and had an absolute blast getting to know each other and doing that I’d already had great respect for both Kristina and TOPO. If you don’t know who TOPO is, TOPO is a research and consulting and advisory firm that focuses on go-to-market strategy for sales, sales development, and marketing. One of the things I love about TOPO is that they really do combine the best of strategy with the best of immediately actionable best practices, which is the kind of stuff that I love and I know our listeners love. Kristina leads analyst teams who are focused on all of those. So once again welcome to the show. 

Kristina: Thank you so much. 

Jeremey: I’ll start the way I start all these podcasts, which is to learn a little bit about you and two questions. And the first one that I like to ask is if you can share your favorite sales or leadership books of all time and why it resonated with you so deeply 

Kristina: Two come to mind for me, that have always sort of impacted me. One is Daring Greatly by Brené Brown. I like to think I read it before she was so cool. Now she’s got like her own Netflix show. I believe strongly in sort of this authenticity in the way you engage with people, whether it be from a leadership perspective, or from a sales perspective. I think that authenticity is what helps you make a deeper, more meaningful connection to try and get to, for example, someone’s pain to try and get them to open up to try and get them to trust you. So I believe that’s been a very impactful one for me.

The second one that I always just thought was fun, was actually Delivering Happiness, which was by Tony Hsieh, the CEO of Zappos. I love the way they set up the culture to try and create this customer experience that trickled down in every single employee and every single action they took. I think that, again, there’s a tangent there for sales that can be really beneficial to take away. 

Jeremey: Yeah, two outstanding ones. One of the things that’s talked about a lot is that Zappos will hire people, put them through training, and then offer – it’s been increasing amounts of money, multiple thousands of dollars – to actually quit. At the end of training. 

 Kristina:  Yep. If they’re not passionate about it. Or if they don’t think they’re a good fit. 

 Jeremey: I think it’s a great idea. Outside of Zappos, I’m unaware of companies that actually literally put their money where their mouth is to ask people to quit at the end of onboarding.

 Kristina: Especially after you’ve done that work. I think what that comes down and what I’ve always found that translates to sales is the passion. You have to really be able to get passionate about what you’re doing, or it becomes very obvious that you’re not. I think when we go in and we listen, auditing sales reps’ calls or helping teams and there’s either reticence or a lack of enthusiasm… it sort of spoils all of your training and your process and all of those efforts. Passion trickles down to some level of like, ‘I want to be here, and I want to engage with this person on the other end of the phone.” 

Jeremey: Lack of enthusiasm is nervousness or do you think it’s really lack of passion for the products and services that the company is selling? Or some combination? Where do you think that comes from? 

Kristina: Candidly, I think it actually comes from the fact that it’s a really hard job to do – sales. Especially, for example, SDRs or anyone that’s doing prospecting. Anyone that’s doing a lot of the same thing over and over again, it’s hard to kind of rally and keep that energy level up all day, every day.

We actually spend a lot of time with managers, helping them try to figure out how to craft a better day or help the team manage their time to also manage their energy. You know, we don’t necessarily do coaching on that type of stuff, but it’s an important thing to consider. The best reps will always be the ones that are standing up walking around. They’re trying to keep their energy up, they try to focus their calls during times when they know that they’re going to be the most focused and energetic, that kind of stuff. It can be a small thing, but it actually is a distinguishing characteristic of people who end up really excelling. 

A lot of the work we end up doing is giving people the structure to succeed. Often, teams are still left to kind of figure it out on their own, even with internal enablement, even with training, even with frontline managers. You still have a lot of reps that are at their desk, not sure if they’re doing the right thing. They settle on what their own secret sauce is without necessarily having anyone checking in on them or coaching them or that type of stuff.

Coaching is starting to see a resurgence with some of the conversational intelligence tools out there, which I think is just one of the greatest things that we could have hoped for. It’s a reason for people to spend more time together, to get better at their craft. What it’s offering is something to rally around to do it more often. Some of the nervousness or the censoring, that type of stuff is just because they’re left alone. They just need the support to help figure it out. 

Jeremey: Yeah, practice iterations in a feedback-rich environment. That’s the key to success. 

I’ve read one of the two. Daring Greatly, I have not read. But of course, I’m a big fan of Berne Browns original TED Talk. I think she might even have done subsequent ones as well. She hit a chord on vulnerability that I think just the right time that our society needed to have that wake-up call. 

Kristina: Yeah. It’s interesting because, on that one, we listened to a lot of sales calls. We talked to a lot of managers and we do a lot of email audits to really understand not just what everyone thinks is the right thing to send out, but what are they actually saying, what are they actually sending?

It’s funny because when we do these audits, people will put forth their best, and we say that’s great. Now put forth your B+, because that’s realistically what 60% of your stuff is. It’s not the one that you spent 30 minutes to craft and make it perfect and beautiful and highly customized. It’s all the other stuff. When we go in and look at that stuff, there are two extremes. There’s the highly generic, which means this could have been sent to anyone on the planet – whether or not they are in this role and care about this type of technology – or it literally is so detailed and potentially overly personal.

The thing I like about this whole surge and like vulnerability, and being authentic, and all this… I think it’s great. But I would just encourage salespeople to remember the context, professionally. Think about how to translate that into your messaging. Get to the heart of the matter for the person on the other end of the phone.

When I’m calling someone trying to really understand their persona, what’s relevant to them and what they care about, it’s about putting myself in their shoes. Maybe even just saying something like ‘Hey, look, I actually talked to folks who are in a similar role today. I know one of the things that I hear is x, I’m just curious. Is that something that you’re struggling with as well?’ Then, that connection is made. Not because I shared a lot about myself, but rather because I opened myself up to taking a chance at getting to something that might be valuable to them. 

Jeremey: What other types of messaging do you think resonate with people in a way that you’re actually giving some value and not just trying to take 15 minutes of their time to conduct discovery on them? How can you give value in that initial messaging? 

 Kristina: Every conversation, you have to make sure you do three things. The first is you have to create context. And I’ll talk a little bit more about how you do that. The second is you have to convey value. Again, this is a business conversation and I brought something to the table that is valuable to you could be a piece of information. It could be something I’m going to give to you, could be something that we’re going to do together next.

The third piece is making sure that there is guidance for what we do next. It seems such like a no brainer for reps, but it’s actually one that they often mess up the most. If they don’t provide a clear direction of what we are going to go do together next. What is the very next step? Am I going to reach out and schedule time? Or it could be explaining what is the next step in the sales process. The more we can be prescriptive, such that I mean, I often joke with teams that you have to make it seem like you’ve done this before.

When you leave people hanging, they get this uncertainty, which is like, so are you going to call me? Am I supposed to do that? They just get this nervousness that ‘like, uh, what am I supposed to do.’ Whereas we’ve all had that experience when you go somewhere, and it’s a concierge-like experience. Where they literally tell you ‘this is going to happen, then this is going to happen, and this is going to happen. Let me go ahead and walk you over to step one to get you started.’ And you’re like, that was so easy. That was incredible, from a customer experience, because we’ve led them along the way. We’ve guided them.

We’re actually launching a CX practice here at TOPO. One of the pillars of CX that we believe is strong is the guided aspect of customer interactions. You can’t just tell them. You have to actually show them, move them, guide them through so that they feel like A) we’ve done this before and other people have walked this path of success before, and B) that the person I’m with on this path is a credible guide. That’s so important as a salesperson, right from the very first conversations. That is, if I’m knocking on someone’s door and asking for their time, I’m being prescriptive about that next step all the way through to those final stages of how we get this deal done and I get them set up as a successful customer.

Those steps create context, convey value, and really close. Asking what are some other ways that we can provide and relevance? It really comes back to making sure that you can answer these three or four questions about your buyer.

  1. How is this person measured?
  2. What does good look like?
  3. What does success look like?
  4. How do they know if they’re going to get their bonus or not?

That’s really important. What are those different metrics or factors that they have to manage in their job? Then, what requests or demands does this person hear in their job? What are the stressors from the organization in their job? Someone in IT might be hearing all sorts of complaints that are different than someone in HR. A third is what gets in the way of this person’s success. It could be resources could be, I don’t know, regulatory constraints.

Lastly, an important one to us in sales is what happens if this person does nothing? To solve this problem, you have to know where you fit in the pecking order. I think that’s so important. We all come at it with ‘this is the most important thing to me as a salesperson to solve this problem for you.’ But how does it feel for the person on the other end of the phone if it’s a ‘nice to have’? Well, we might actually want to acknowledge that there are other fires burning for them and try to help them understand where we fit in that.

THERE’S A LOT MORE AFTER THIS! Listen to the full episode for the rest of the conversation between Jeremey and Kristina here.


If you have a passion for the art and the science of sales, are looking to further your career, or just want to hear some great, practical tips, ‘Hey Salespeople’ is the podcast for you. Subscribe so you can follow along as Jeremey interviews the brightest minds in modern sales to bring you immediately actionable advice. Listen and subscribe here.

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