The webinar “The Power of Storytelling” centered on using storytelling to enhance the sales processes by engaging buyers, delivering personalized demos, and driving impactful narratives. Hosted by Justin McDonald, CEO of Saleo, it featured panelists Doug Landis, storytelling expert and CEO of DL Advisory; and Brian Cotter, Senior Vice President of Sales Engineering at Seismic. The discussion highlighted the transformative role of storytelling in overcoming challenges of technical sales, fostering emotional connections, and aligning the sales approach to buyer motivations in the evolving post-COVID marketplace.
Read the full transcript below:
Justin McDonald:
Doug, Brian, thanks for joining me. Excited for the discussion today.
Just a quick intro. I’m Justin McDonald. I’m the co-founder and CEO of Saleo. All about storytelling, all about demos.
I’ve also been in SaaS for about 19 years. So love SaaS, love the demo, love to talk, to thought leaders like Doug and Brian.
So, just a couple intros. I will say this is not your atypical go find a bunch of panelists and pick a topic.
These are two gentlemen that love storytelling, that know it well, that practice it, that lead it. You know Doug has been in SaaS for a long time, a big thought leader in the sales space, was literally the chief storytelling officer at Box.
So he has a few things to say about storytelling, of course, came from Salesforce; as well as Brian. I think there may have been some overlap with both of them at Salesforce.
And then Brian Cotter, the SVP at Seismic, a customer, a friend of ours, and, literally invented a concept called Storytelling Labs, which they implemented and executed at Seismic. So this is a really great topic for two gentlemen that know it exceptionally well and certainly excited to jump into it.
So before we do, do you guys want to say a couple words? Say hello?
Brian Cotter:
Sure. Well, Doug, it’s good to see you again.
Justin, thanks for having us. And, you know, being a career presalesperson other than two years out of college, realizing I was not an AE, it’s always been about the art of being able to visually present their future on your platform.
And that I’ve always kind of looked at storytelling as a way to connect with people, especially when we work in technology where it’s not always easy to understand and follow the impact and the outcome that you can drive with it. So for me, my whole career has been trying to figure out different ways to actually connect with the audience, articulate, you know, the value prop, walk them through based upon where they are on the sales cycle so they could actually embrace what the offering has as far as how it could solve problems.
But also more importantly, how could they actually realize value over time and accomplish their objectives. So everything we do is all about connecting with people these days and storytelling is a major vehicle.
Doug Landis:
And you kind of nailed that, Brian. I mean, look at the end of the day, storytelling is a form of communication.
And in fact, it’s the oldest form of communication that we have. If you even think of what they were drawing on the caves back way back in the day, they used, like, four visuals to tell a story of 100s of years.
And it’s how we communicate naturally, but we’re talking about this beforehand. But it’s so weird, we get to work and all of a sudden it’s like we feel like we need to speak in fragments and bullets and maybe, I don’t know, what, like, I want to say Twitter, but I guess that makes me old. The x language, which is only 140 characters.
The reality, you know, the truth is it’s like we need to get back to this art and to this form factor of communicating because it’s the easiest way for us, as listeners, to understand, to connect, and to digest the information. And unfortunately, when we all sell technical products, we get too lost in the myriad of details and features, and we lose sight of the fact that we’re actually a human being having a conversation with another human being.
And, you know, this clearly is a subject that is near and dear to my heart. It’s something that I’ve been involved in well before I got into technology, just an FYI, because, I am an actor.
I’m actually a professionally trained actor. I went to acting school in San Francisco.
And the truth is when you think about acting, fundamentally, what you’re really trying to do is tell the story of the character that you are supposed to identify and understand. And, it’s difficult, but you’re communicating.
Right? Ultimately, you’re trying to elicit a positive response from the audience. And, you know, if you think about that, that’s really what we’re trying to do with our customers and our prospects is elicit a response that says, oh, yeah.
I get that. Because you know what? When you’re on the receiving end and, Justin, Brian, I’m sure you experience this often.
When you’re on the receiving end of someone trying to sell to you, especially if it’s something technical, you’re also thinking about one, how do I get other people on board? And two, how do I articulate what this product is and does and what value it’s going to deliver to us in our business and what problem it’s going to help us to solve? And then three, of course, how do I get comfortable with switching from what I was doing to now using something totally different? And those are all challenges that we as buyers have to overcome using story form in your communication, not all of your communication, but in your communication. Makes it a lot easier for us to capture and understand.
Justin McDonald:
Yep. I love it, Doug.
Totally agree. Very good.
Great. Well, Laura, you want to, go to the next slide, and we’ll jump into this.
We got an action packed agenda. The way these guys expound upon good thoughts and ideas, we’ll probably get through 75% of it, but it’ll be a great 75%.
So excited to jump in. Doug, to kind of piggyback off what you said of, you know, it’s very easy for sales, presales folks to get wrapped up in the technical details, the constructs.
Right? And I think with, you know, post COVID, and Brian and I have talked about this, you know, several times over the years, the world’s changed. It’s very different.
Right? I think Zoom and talk about getting wrapped up in the technical and devices, it’s very hard to have the human connection. So I think every bit of time that you spend with the buyer, between the seller is exponentially more important.
Right? It’s higher risk. It’s high reward.
I think, you know, HubSpot and some I think Gartner did a study that basically said, you know, out of 80% of the time buyers spend evaluating, you’re only spending, you know, 19 or 20% of that time with them. So selling SaaS is hard.
It’s always been hard. It’s gotten exponentially harder.
The storytelling, the human elements, really comes into play – excited to jump through it.
Doug Landis:
You know what’s interesting, Justin? I’m curious. Well, first of all, I’m super curious about the 5 decision makers in a deal.
It feels like it’s 11 to 20 now instead of just 5. But, secondarily, if you think back in your early career, you know, this is dating myself.
But back in the field when you’d go into an office and you have meetings in person and face to face, which I fundamentally believe we’re going to kind of move back to again because we miss a lot of that. But, you know, what’s interesting is it kind of became I felt like it was more natural to do that, to be storytelling or to do storytelling, to be a storyteller in those in that context when you’re live and in person with a bunch of people because you’re talking about life and your weekend and the story about how you got here and how you’re plane almost hit a bird and like, just stuff happens.
But all of a sudden, when you are on Zoom, and we’re in this virtual world, and it feels like, okay. We got to get to it.
Right? I’m curious. Do y’all feel that way? You guys are young, so maybe you were never…
Justin McDonald:
No. I’m not young.
When I was in SAS, it was first called ASP. So it wasn’t even called SaaS.
There you go. dating myself a little bit.
But, I agree, and then I think it’s a parallel to the water cooler. Right? The water cooler is a time when people have an opportunity to tell stories.
Right? It’s the natural communication, it’s the community feel.
And so I totally agree. I mean, I do think the world is shifting towards back in office for a reason.
I mean, irrespective of productivity, I think people can be productive either, but just the community feel, the culture that can be built, the conversation that can be had, the stories that can be told, right. They’re all relevant.
They all happen better in a natural in person setting. And, I think there’s merit to it.
Brian Cotter:
Yeah. One of the things on that, going back to my two years of when I actually didn’t do presales, we were formally trained to walk into doctors and lawyers offices and to look at the walls, look at what’s in the room, figure out something that you could kind of connect with them, build that relationship.
And, it served me well over the years because you can create relationships by just seeing a picture of a sailboat and a raincoat and a waterproof bag and the person’s a sailor. But going into Zoom you’re also training people to look at the background of the people in there, but, you know, people backgrounds.
It’s harder to get to know them. And, Doug, to your point, I think part of storytelling is connecting with your audience at another level and understanding what motivates them and why they’re interested in solving the problem.
Is it purely a task or is it something that could get them promoted? And so you are right. Building relationships, and I do agree with the 5.
I actually think there’s more of them, but it’s kind of like the iceberg. There’s 5 people that you’re talking to and 20 people underneath that will pop up at any given time.
So, I do agree. Figuring out how to build relationships whether you’re in the room or out of the room, is a future that we all need to figure out how to address the right way because that will help stories land better.
Justin McDonald:
Yeah. Sometimes it does feel like 11 or 12 influencers and people, you know, speaking into decisions.
Doug Landis:
Cool. And you got to know who those people are.
Justin McDonald:
Yes. They matter.
Doug Landis:
The stuff that’s going on behind the scenes is actually more important and more valuable. Getting everybody just aligned on the problem itself.
Right? You could have the best demo in the world. You could have the best presentation in the world.
You could have the best prospecting email in the world, but the reality is, Justin, you know this. Like, you’re CEO of a company.
How many decisions do you make on a daily basis? And how often are you going through the reprioritization of those decisions and what’s more important is so critical. Like, even just knowing that, I think part of this kind of goes into the narrative piece that we’re going to talk about here, but, just kind of knowing that Justin is the CEO of a fast growing early stage software company, I can build somewhat of a point of view or a perspective about his world.
Right? And in that, I can also probably share some stories about other CEOs that I know that meet on a regular basis, because guess what? It’s a super lonely job. Right? So I’m already kind of inferring based on knowing what your what your world is like.
I could be wrong, but based on that, based on knowing my audience, and knowing you, I can pull out some really interesting stories based on my own experience of starting a company and feeling like, you know, days where I was like, I don’t know who to talk to. So, you know, I’m talking to random people at coffee shops just trying to get perspective because I can’t talk to my board and I can’t talk to my team because they all believe that I know what the hell I’m doing.
Justin McDonald:
Yeah. We can have a therapy session here too if you want.
That’s fine. Away from storytelling.
But, yeah, it’s all salient points.
Yeah. I would say how many decisions do I make before 9 AM? And it’s quite a few.
So try to make them in morning, the big ones.
Doug Landis:
Well, some people are better at night.
Justin McDonald:
That’s true. That’s true.
Very good. Alright, Laura.
So next slide, and I think after this, we’re going to stop doing slides and get into some really good content. I’ll leave you all with some of this data here.
I think it’s very relevant. It’s very accurate.
I think one of the things I’ll mention is that storytelling is not natural. Right? It hasn’t always been natural for me in the 19 years that I’ve been in SaaS.
I think it’s exponentially important today, more than it’s ever been. And so I think just hearing from folks like Doug and Brian and what it looks like, to get some repetition, get some best practices, is critical for myself as a leader, and for someone that’s just starting out.
You continue to use it day in and day out. I can’t tell you the amount of stories, decisions that I try to make or to get buy in, even in a leadership team in Saleo, where I’m doing it through the lens of a story.
Right? It will resonate more. It hits better.
It gets perspective. It gets credibility.
And so I think two of the things that are near and dear to my heart that will kind of weave throughout today are if you can tell a story through the lens of the customer, right, it’s like the microplot in a bigger story. It kind of moves it from fiction to nonfiction.
It becomes very real for your buyers. So I think as we’re thinking about stories, think about how can you actually tell the story through the lens of your customer, which I think really hits home.
It adds a ton of credibility and relevancy for your audience or for your prospects. And then two, especially since we’re all in software, right, I would argue most of the people on this webinar are selling software.
When you look at the actual demo story, right, the data is the story. Right? The UI can be pretty. The UX can look great, but when it comes to the actual story you’re trying to tell, it’s around the data. What’s on the screen? What are the relevant pieces of terminology or localization or use cases that are relevant to your buyers? So, anytime you’re trying to tell a good story within the actual software demo, it has to come back to the data.
And data is one of those terms that’s thrown around left and right. In software, you’ve got engagement data. You have measurement data. You have intent data. You have productivity data. You have win rates.
Right? So data can sound very ethereal at times, but when I say data, I mean the actual data that’s in your product that allows you to communicate the correct story through the lens of the software. So, couple of things that are passionate, for me as well as Saleo that we’ll talk about today.
Doug Landis:
I have a little quote, when I do storytelling workshops, and it’s similar to the last, square here, which is facts fade, stories stick. I mean, just think about that.
You know, when it comes to things like elections, not we’re getting political. We’ll stay away from that.
But, you know, the reality is we forget about all the stuff that people throw out there, whether we believe it to be true. Who knows? But the reality is we understand the stories and the experiences we’re having. Right?
Maybe it’s, you know, we went to a rally and then we met people, we had an experience there, there was a riot or whatever it may be, or maybe it’s just like you remember when the election was actually over where you were and how you celebrated or didn’t. You know? Like, that’s what we remember.
We don’t remember all these, like, gory little details. This is important because here we’re talking to a presales community that y’all have a lot of facts and y’all have a lot of stats and Brian, I’m looking at you because, you know, you’re the king of this.
Not in a good way, not in a bad way. But when you’re talking about really technical stuff, it’s so easy to get just caught up in the details and the clicks rather than the story and the narrative and why it should matter.
And I think it’s like I feel like oftentimes, especially when it comes to products, we get into this we get into this, like, oh my gosh, I have to show everything because the product will sell itself. Right? It’s because it’s so amazing.
And you’ve been drinking too much of your own champagne. And you realize, like, okay, cool. I only needed to see two parts of this because what really matters is how is this all going to work in my world? And why should I make this change right now? And how do I actually sell this internally, to the other, you know, 20 people that we talked about earlier?
Brian Cotter:
Yeah. Doug, you and I talked about this in the past, but, you know, I like the facts fade, stories stick.
And, you know, one of the things that on my team, we talk about a simple formula actually based on Hollywood, and it’s I plus E equals M. You know, if we can learn and share information from each other, we build connections and those connections open up the doorways to trust where then we become more emotionally connected.
We understand the motivation of what we’re doing at that point in time and then we become memorable regardless of the tech bit or bite or feature or function. It builds a relationship that says this person is looking out for my best interest.
It actually helps elevate and drive the authenticity of why you’re there, but it gets away from just showing a bunch of bits and bites. But Justin, to your point, you also need to walk them down through where they are, their problems or their initiatives, the solution that you’re going to present that gets them to the outcome that they want because there has to be that buy in that goes beyond emotion.
People buy with emotion, but they justify it with the numbers. And I think that is a critical part about software as a service or technical selling, not going purely down the technical wormhole.
Because people are like, yep, yep. And people might not sign the check, and that’s what we need to do in sales.
Stories that sell is what we’re hearing.
Justin McDonald:
Yes. They do.
Is and even more so when they’re authentic, genuine, and real. Right? So, moving on to kind of this next section, we’ve already stepped into the why storytelling matters.
What – talk to me about the audience. Because I feel like for me, when I’m walking into a room, the situational awareness or even walking into a deal, understanding the audience, what makes them tick, what they care about, it’s everything to telling the right story or knowing how to adapt correctly.
So we’d love both of your thoughts on how the audience plays into great storytelling.
Doug Landis:
I mean. It is directly connected to probably one of the most important reasons why most people suck at telling stories, one, we’re not really clear on who.
I fundamentally believe most people suck at telling stories, which is really sad because, you know, we think we do this well, even at parties. But the reality is we’re at parties and we realize, you’re that person in the corner that nobody wants to talk to because you ramble all the time, and you never really know where you’re going with your story. The reality is you have to be really thoughtful about who you’re telling the story to or who you’re talking to, what matters to them.
So be really thoughtful about your audience, and make sure you’ve got a story that is relevant to your audience. But more importantly, be really, really clear about the point you’re trying to make.
And that point must be relevant to that audience person, to that audience member. Now the challenge is and Brian, I’m curious your thoughts on this, what do you do when you’ve got a mixed audience? You’ve got a CEO, CFO, CTO, you’ve got some architects, you’ve got some business analysts, you got a whole bunch of people in the room.
What story do you tell? How do you adjust when you’ve got multiple audience members in the room?
Justin McDonald:
I would argue that’s probably the single greatest challenge in storytelling and software sales is multiple audience members that care about different things. So yeah.
But I’d love to hear Brian’s thoughts on this because this is something I see software folks struggle with every single day.
Brian Cotter:
I laugh and I joke we don’t have enough time in the week to actually walk through this particular topic, you know, it’s a big one. And kind of just at the high level, the values that we’ve instilled in our team. Doug, you know, I kind of have a modified version of the good old fashioned v two moms.
The value, the vision, the methods, the obstacles, the metrics or the measures. And the values are, like, know your team.
We sell as a team. We need to go to battle together.
Know your stuff. I talk about being unconsciously competent on your material, your customers, your segments.
So you can do discovery, have conversations, and all your product stuff is back in the brain, but you’re having a human conversation. And unconsciously competent is one of the 4 stages of adult learning theory.
And just means that you don’t have to think about what you know. And the next one is know your audience.
Know who you’re walking into the room with, understand as much as humanly possible who you’re selling to, who’s a champion, who’s someone you might have to mitigate – like techie dictators that might take it over. You have to figure out how to just mitigate them versus sell them.
And then the last part is know their outcome. Knowing where they want to go is critical.
And kind of getting into a room, one of the things that I created was a one pager. So, Doug, when I go into a room, I’ve done the due diligence.
I have the confidence I know my stuff. I have the conviction that I believe it, and I have a superpower called situational fluency. There’s not one thing that I can’t go and bring it back.
I call it the yoyo, kind of, approach. Like, you’re on your thing, you’re on your story line, you go down, you answer, you come back.
And you can completely keep the audience engaged, answering questions, but being able to figure out your audiences, figure out when you have to park a lot of stuff or when you have to answer a question – as far as who they are. And the one page that I created for myself, literally I’m coming in completely prepared and on the top, it looks like a table.
And I literally – whether I know them or not – going around, I understand every single person. Because inevitably, you get a C-level person that just drops in and you got to pivot.
Hey, Doug. Thanks for coming. How long do we have you for? Good. What’s the most important thing for you?
You know and you let everybody in that room know that person needs to kind of hear what they need to hear in the first 5 or 10 minutes after they’re there.
But you still are going to address the different topics that’s important to each one. So by going around that room and it’s called the 4 box where I basically identify who are the initial people, what are the quotes that they said, what are the areas of the business they’re trying to fix, and how I can actually insert that into my original flow.
So going in being prepared, understanding your team, your stuff, your audience, and your outcomes, then by taking a couple minutes in the front to kind of know what has changed gives you the ability to deploy that situational fluency. Easier said than done.
And one thing I’ve realized is doing this for as long as I have, some of this stuff is just something I do. You need to look at you and your teams and the different people in your sales organizations to help level them up. Because a lot of these things are just experience and getting involved in practicing it.
Doug Landis:
I love the concept of situational fluency.
I think that’s something that everyone needs to adopt. I think along with that, though, Justin, to the original question about audience and how important they are.
There’s two things that I wanted people to take away from this. One, not only situational fluency, but two, fundamentally, what we need is, hey, marketers, if you’re listening, this is on you right now. You need to sit down and build a story library for your teams. Help them understand what stories they should be able to tell by persona and by stage. Because you’re typically talking to the same persona, similar audience members, over and over and over again.
So you should have some stories already kind of built out that they should be able to tell quickly at the drop of a hat. And then reps, SEs, AEs, that’s on you to know those stories because you got to have them at your fingertips.
Secondarily, I think it’s also really important just to know that, I know part of this is a discovery conversation, but I think it’s also really easy for you to go in with a hypothesis about someone’s role, their world, and what they’re likely trying to accomplish. Because, again, you talk to the same personas on a fairly regular basis.
And with that hypothesis, you can actually develop a story line. Right? So based on your hypothesis, you can develop a series of stories that are aligned with that hypothesis.
By the way, the hypothesis doesn’t have to be right. It just demonstrates that you actually put a little effort into this.
You gave a shit, and you kind of put yourself in their shoes to try and determine what you thought was important, what problem they’re trying to solve, because you’ve heard it and seen it before. And then based on that hypothesis, guess what? You now have a slew of stories that you can tell in that moment.
And when you have stories, kind of at your fingertips, it starts to feel more natural. You know, the one thing that I think is also really important from this conversation is we need everyone to become better at storytelling, but I will never tell you that storytelling is a way in which you communicate 24/7 because that’s just weird.
Like, you got to know how to get into and out of a story. Right? You got to know when is a good opportunity to tell a story, and when’s it a good opportunity just to spew out some data points, some facts. Right?
Justin McDonald:
Yeah. I think just to augur in on that, because just combining the concept of situational fluency with being in story, when to break out with audience members that may change.
And to Brian’s point, the CEO or the leader may pop-in midway through. Right? So I think the reps that have done it the best that I’ve seen in my career are those that have the fluency to know when to break out, to address the actual people, the different stakeholders, the different interests that have popped in, to be able to break out of the story, recognize them, drive engagement, and then come right back to it.
So I think the fluency and then the clock speed. Right? Those are the fluency and the clock speed to be able to pick up on it.
Know when to pull an audible, know when to pivot, and no one to get back in and reengage. So I think it’s a hard skill set to learn, but something everyone’s been trying to double click on.
Brian Cotter:
On know your audience and if a CEO or a C-level person showed up either in the beginning of the meeting or the middle of the meeting, I’ve seen it a couple of times where the sales team was in there and someone walks in or we’re going around the table and the question is like, oh, so Doug, what do you do? And they’re like, oh, I’m the CEO. So, lets talk about first impression not really landing. Being unconsciously competent and really for a presales professional, you know, not an AE, really demand that your AE gives you the full list of who’s there and also the executive suite. Because you need to be able to pivot in that moment, not only pivot to say, oh I need to present this to a c level person, but you need to know their name.
Like, go in there well prepared. And I’ve seen a couple meetings where it literally was like, oh, I’m the CEO. I’m the person that’s going to sign the check. And the AE was like, uh-oh.
So, it’s just really the nuance part of this. It’s the little things that make the biggest difference.
But, knowing your audience, I think, is more than just doing discovery with them. It’s also understanding who’s going to be part of that decision making team and who could drop in at any given time.
Doug Landis:
Yeah. I’ve totally done that before. I’m like, so wait, sorry. What’s your role?
Justin McDonald:
That’s when you pull the old self deprecating card and just back up.
Doug Landis:
Yes. I’m like, you know what? To my credit, I didn’t actually know what you look like. You know. So.
Justin McDonald:
Well, speaking of discovery, and Doug, I know you have some thoughts on this. It may not be what you think.
Right? And I think it’s changed in this world of buyer enablement and, to see information that people have access to, the time that you have with the buyer. So let’s talk about discovery, what that looks like traditionally, as well as maybe what it looked like now, in the actual sales process, along the way and maybe not as deep initially, but done sequentially, and with a different approach.
So we’d love both of your thoughts on this. And, Doug, I know you had some really good insights on one of our calls prior that I’d love to hear.
Doug Landis:
Yeah. You know, if you know me, you know that I’m so anti-discovery it’s kind of funny. And it feels like I’m sure everyone’s going to be like, wait, what that doesn’t make any sense. But it really does because, look, at the end of the day, discovery is so much more for you the seller, than it is for me the buyer, and that is something that we just have to be really careful about.
This is why I have some strong and quite provocative thoughts about it. I think, first of all, a lot of people suck at it, because you view it as just a laundry list of questions that you need to go ask in order to validate whether or not it’s a real opportunity, whether or not we should continue to have a conversation.
I’m cool with that. But you know what? You put way too much work and onus on the buyer in this process than you do on yourself.
This is what I mean. Discovery, to me, is trying to help us to understand. Is there a real problem here? Do we understand the depth of the problem? Is this something that we can potentially solve?
Because the truth is we may not actually be the right fit for you, because I don’t even know if we can really solve your problem, because we’re not really aware of the problem itself in your words that we’re trying to solve. My whole thesis is discovery should be about building a hypothesis and a point of view.
This is not rocket science, it’s something that’s been talked about for a long time. I call this hypothesis selling.
But your job as a rep is to go into every conversation with a hypothesis about the situation, about the person, about what problem they may be experiencing, what they’re really trying to solve, and what value means to them. Because the truth is you talk to people like this all the time.
And so discovery shouldn’t feel like this Spanish inquisition. So you should never ever…
There’s certain words out there that just give me, it’s like writing on a chalkboard, It’s like, tell me about. No. I’m not going to tell you anything.
You tell me. You tell me what you think, and my job is to then to validate or refute that.
I don’t want to tell you anything because I got enough shit on my plate to think about to and the last thing I want to do is just answer a bunch of questions that you just have and this list that you need to ask in order to validate whether or not there’s a real opportunity.
Justin McDonald:
Yeah. Boy, you’re upsetting some sales managers out there, Doug.
That’s a discovery. That’s right.
I think there’s some really good points in there.
Doug Landis:
I mean, Justin, if you’re buying software, Brian, you guys buy software. You guys have sellers sell to you. What do you want to hear from them? Why do you think, so often as buyers, we say, show me a demo.
Just give me the pitch. Why? Because I don’t want to go through this whole narrative, not even narrative. It’s the script that you have, which is like, here are all the questions I need to ask. It like, no.
I’ve already thought about this. Just show me what you got, because I’m going to put it all together in my own mind.
Justin McDonald:
Yeah. I think something that you said about coming in with the hypothesis, I’ve seen it done really well.
It was called something different, but you’re essentially reinforcing your hypothesis throughout the journey to get further buy in. Right? It’s repetition of our assumptions of what we know about you.
Right? And you continue to get buy in from your buying committee from those 5 to 11 particular stakeholders on the buyer customer side. So I think it’s continued reinforcement of the hypothesis, as well, that really drives a consistent narrative internally, because you have less control internally.
You don’t know what the buyer is talking about. Right? You don’t know who has the most amount of power or the most amount of influence.
So continuing to reinforce, reiterate that particular hypothesis is important.
Brian Cotter:
So I agree with Doug and going back to the word discovery, what does it really mean? I mean, 25 years ago, I worked at BMC. The seller owned the whole process.
And if you want to buy anything, you had to call them. And we would say we’re coming in for 2 hours, and we didn’t have the Internet or access to the information. I mean, how many sales reps do you know that went to the library and did research? We’re barely getting them to, you know, go on the computer and use generative AI with prompts to do some stuff.
And I’m joking and I have a tendency to have the Irish gene in me of humor, but, you know, the reality is discovery has changed from 1999 until today. And it’s because of the access to information. Justin, you’ve heard me talk about this a lot.
You know, the pandemic created nothing but accelerated everything. And really what that means, the buyers are in control of their own journey.
They want it when they want it. They want it where they want it. They want it digital.
And you as a group need to kind of reimagine how you’re going to engage with that buyer.
But the second part is generative AI, kind of the last 5 years with it since the pandemic has literally created Albert Einstein out of every one of our buyers. To your point, Doug, they’re smarter. And they’re not smarter like they’ve done more research. Like, they know their problems better, if not better than you do yourself.
So when we kind of look at that, I really do believe we have access to technology. We have access to information. We have access to come to the table with a point of view or what I call a brush fire. You might not know everything, but you need to earn the right to either politely validate their thinking or politely challenge their thinking.
And the reason why I bring that up is I’ve had 2 hip replacements in my young life and 3 hip surgeries in 4 years. When I went into the doctor, I could basically go in saying, I went to WebMD, I need a hip replacement, Thursday, the lateral incision, we’re good to go? The doctor’s going to be like, no way.
He’s going to go through the medical history, the physical exam, some blood work, put me in a machine, and come back with a point of view. The reality is the world we live in sales, you have a lot of buyers that are doing research on WebMD and coming to you and saying I want to fix this.
I can’t see one buyer going in and saying I’ve solved the problem for a $100,000 and self you learn to where they spend a $1,000,000. The art of sales is in each one of us where we need to figure out new ways, to Doug’s point, to understand their business as good if not better than they know themselves, because we’re the experts.
We need to guide them through. It starts with a hypothesis and you can do 85% of your research before you even meet with one person from that company.
So discovery is still needed. But when I say discovery, it’s understanding the world that your buyers are in and how you can help solve it.
The techniques and the tools that we have are very different, and our buyers are just more evolved. Like, the B2C world is coming into the B2B enterprise selling space, and we need to adapt to that.
So on that front, I do agree with Doug. We need to rethink, reimagine this, and I don’t think discovery is an interrogation where you go in and you just fire questions.
You’ve got to earn the right for them to share information with you.
Doug Landis:
Totally. By the way, an important word that is – I’m a I’m a weird linguist at heart.
The really, really important word in this whole exercise is the word might. Because the last thing I need you to do is to come into me in my world and say, oh, I know what your world is like.
No. You don’t.
You have no idea. You have a perspective, and you have a point of view based on talking to other people like me, but you don’t really know what’s going on in my world.
And so it’s important to use that word in the conversation, in the context of having this business discussion. Justin, as I was thinking about this conversation, you know, it led me to kind of consider some of the other CEOs at early stage software companies that I’ve spoken to.
And it got me thinking that your role might be pretty similar to theirs. Let me kind of paint a picture of some of the things that they shared with me that they’ve struggled with, that I think might be a similar challenge.
Might just, all it does is it deflates the defense mechanism that we immediately feel as buyers when you start, you know, kind of talking at us.
Brian Cotter:
I’m taking something away. I mean, Doug, the reason why I like that, why I love it, is I’m very interested in moderate endurance events, and it’s not the first 97% that your body can actually do whatever you’re doing. It’s the last 3% that causes your mind to lean in.
And something like that, the might, it’s subtle, but yet it’s so powerful and it unlocks a lot of things. Especially if you can connect with someone that’s coming in with their arms crossed, like, nope. There’s nothing you’re going to teach me.
Like, uncross their arms and lean in a little bit by kind of coming into the point of view and saying, well, you might be like these. We would like to learn a little bit more. You can physically see.
And I think one of the questions here, you know, how do you understand when someone’s actually changing or getting that story? There’s the physical nuances that we all have, there are tells, like on a poker table.
You know when people are getting interested and you know when they’re not. And I think I’m just taking that away, Doug.
I appreciate the might word. It’s a small little thing you brought up, but it’s very powerful if you can apply it in the right situation.
Doug Landis:
Well, here’s the other thing that it does too is even in telling a story, but, you know, the story might resonate with you. Right?
I don’t know. I mean, it may or may not.
But what it does now is it empowers them to correct you.
You know? As human beings, we also like to be right, unfortunately. Hate that, but we do.
We like to be right. And so if you’re telling me something about my world that might be off, guess what? You automatically give me permission to correct you.
And in doing so, I just learned so much information that I probably wouldn’t have gotten before if I just asked you a straight question. Point blank, direct, to the point.
And so, it reduces people’s defense mechanism of, like, oh, this is just bulls**t. I got to go through this process again.
It’s like, no. Actually, you’re almost there.
And, I’ll tell you, this is also why whiteboarding is so fun because if you get on the whiteboard and start mapping out what you think the world might be like. And then all of a sudden, they’re like, well… Because you’re like, it may be like this.
I’ve done my homework, and I’ve talked to people like you.
Well, yeah, actually, it is, but these things are different.
You’re like, oh, cool. Come on out. Draw it up.
Justin McDonald:
Yep. I couldn’t agree more. In going back to the genesis of that question it’s reading the room. Right? There is nothing worse than thinking you’re right and then not resonating.
So I think reading the room, gut check with the actual audience, and, just a straight up question of, hey, does this aspect make sense? And maybe a portion of it does, or that did, or no it’s not – we’re totally off base. Now you can pivot, now you can move on. Right?
So I think reading the room, a gut check with the audience, just – it provides participation, which if you’re doing a Zoom meeting, if you’re virtual, nothing beats engagement because it’s very easy to multitask and drift off into Zoom land and surface 50 minutes later and not actually see what was discussed.
Brian Cotter:
It’s harder on Zoom to do this, but, Doug, I just want to kind of double down on the whiteboard.
I’ve been doing this presales role for 23-25 years. I’ve yet to have someone ever come up and grab my mouse on the demo and start clicking around.
I can tell you without a doubt, 1 in 10 people – when you’re doing a whiteboard – will get up and actually grab the whiteboard and they’ll start literally correcting you or drawing your discovery.
Coming with a point of view and validating it, Doug, but doing it with a whiteboard, it’s a lost art form that unlocks so much stuff, but then you leave there not just with your notes. You leave there with a picture of their writing.
And I think it’s one of the things that I can’t stand with the Zoom world we live in. That power is not as widely used because it’s hard to do a whiteboard on a Zoom meeting.
But if you are in a meeting, kind of like your might word Doug, if you’re in a real meeting getting to know people and you have the opportunity to come to a point of view, think about leveraging a whiteboard. It will get people talking, and it will validate so much, in a shorter amount of time.
Justin McDonald:
Yeah. I was talking to the young SDR, up and comer.
Good kid. And, we were talking about doing whiteboard sessions and doing demos on-site, and they’re like, wait, people do demos on-site? Like, that’s a thing? It took me back. That was the only way to do demos, was on-site.
I know we talked about discovery and just some more pragmatic tactical approaches. Brian, what have you seen work well and I think, honestly, when you’re talking about changing how discovery is done, it comes down to friction.
Right? There’s too much friction in the sales cycle that the buyers or the prospects don’t want to endure. So what are some tactics that you have used or think are really good takeaways for the audience of how to streamline discovery. You know, discovery demo or disco demos, kind of do an all in one and learn along the way through the lens of the product.
What’s worked well? What can the audience take away?
Brian Cotter:
Well, the interesting thing is to Doug’s point, you know, depending on who you’re meeting with in the different stages, you’re learning about the business as you’re going through the sales process.
So, if the statistics are right, 83% of the time the buyers are alone, from Gartner. 17% of the time they’re with vendors. And if there’s 5 vendors to start off with, you have 3.4% of time to actually make an impression.
So some of the things, like, anything you can do to preamble. Justin, you and I have talked about this. To educate them through some sort of experience, like, interactive product tour or sharing information, depending on what communications that you’re having.
Like, somehow sharing your point of view when you’re not with. I mean, Doug, you kind of mentioned marketing.
I think marketing needs to really make sure that they’re starting. It’s kind of like onboarding for an employee starts the first call with the recruiter. It doesn’t start when they’re hired.
Like, a customer is not a customer when they actually give you the money.
Yes. Technically by contract, but you’re working on them to be a customer long before you’re actually selling them or showing them anything.
So, you know, Justin, any chance you can get where you can share information with them that they’re interested in, that you can get some sort of feedback as you’re in the early stages of qualification, I think is great. And I have a lot of deep thoughts about that in the world we live in. I call it the consumerization of the B2B enterprise selling space. People want a B2C experience when they’re buying a million dollars of software.
We need to take those learnings and apply it when they’re shopping, when they’re kicking the tires. Once you get to them, to Doug’s point, you have to be prepared.
Preparation is everything. Preparation isn’t discovery.
Preparation is: you know your stuff before you go in there, which will unlock so many different things. The end point of a proper preparation, to Doug’s point, you have a point of view or hypothesis that you can come in.
And you need to have in your quiver, you have to have multiple arrows. Like, can I do this for a conversation? Can I actually do a whiteboard? Do I actually need to do a discovery demo? And the problem with the discovery demo, you’re tight roping a razor blade.
You go too far left or right, you’re going to get cut. And you will be in the weeds that you can never pull yourself back up.
So you need to make sure, I hate the word harbor cruise, but you better have some sort of overview-intro-visual-thing that you can walk customers through and give them the main points of what you want to show them to get them talking. Because if you’re in a real product and the next thing you know, oh, what about that? You’re 7 clicks down and you’ve lost the meeting.
So, basically, preparation is everything. Going in with a couple of different quivers or arrows in your quiver that you can use to get them talking.
But also knowing your audience. You should be able to understand before you’re going in there, your audience and what might be important to them.
And the other part is, even in this meeting with us, I’m taking notes. I’m learning. I’m adapting, and that’s the situational fluency.
And if you’re prepared, you have a couple of different tools or arrows you could use, and you have that situational fluency.
All this is, in my opinion, just putting in the work. Practice the way you want to play and be prepared for something to go sideways.
Justin McDonald:
Yeah. Speaking of audibles here, I’ll just read John. He just asked a question. I think it’s a very astute question. “People confuse discovery with scoping of the solution. Where do you draw the line, and do you draw the line?” And, boy, just thinking back to some really complex enterprise selling I’ve done in the years, that’s a really, really thoughtful question.
I would say and, we’d love your thoughts on this, I don’t think discovery ever ends.
Like, I think that process never ends. Scoping of the solution, obviously, can end, at some point, but, I don’t think discovery ever ends.
I think you’re constantly learning. I think you’re constantly asking questions.
I think you’re constantly pivoting and adapting, and understanding. So not sure what you guys think.
Brian Cotter:
I agree with you one thousand percent on that. Discovery, the scoping, it’s a slippery slope, but also, Doug, love to get your take on this.
The world I live in, don’t confuse selling with implementing. There’s a point in time that you actually have to show them the value so they’re like, I trust you. Then you get into the details, you prove that trust, and then you can sell more.
But, I’ve seen many times where we get into discovery, like we’re implementing and we’re actually doing a dissection and we’ve completely missed the point of – They’re trying to solve the problem; they’re not trying to figure out how it all works.
Doug Landis:
But I mean, I think John asked a really interesting question, which is what is scoping? To me, scoping is: can we get through some technical components, some technical questions, so we can determine whether or not this is actually something we can do. This is something we can actually solve. This is something we can actually help with.
I feel like that kind of puts scoping under assessing, right? Whether or not this is actually something that’s a good fit for us, because it may not be.
And I don’t want to sell somebody something that’s actually not a really good fit, because we’re going to feel it downstream with churn. And as a former investor, churn is not good.
We don’t like churn. As sellers, we’re like, who cares? We’ll throw it over the fence. We’ll figure it out.
But, to the point of discovery, this is why I don’t like the word, because it’s just having a business conversation.
In conversations, what do we do? We ask questions of people, and then we share information. It’s a two way dialogue.
And it is ongoing. You’re always looking to learn more with the different people that you’re talking to. Right?
And so that’s why, if you create scoping as this single point in time, we’re going to answer a series of questions. And then discovery is something that’s just going to continuously happen.
It’s kind of how I think about it.
Justin McDonald:
Yeah. I agree, especially on the scoping.
It could be twofold if someone has multiple SKUs, multiple product lines. The scoping could be determining which one’s the best fit or if it’s a fit at all. So I think, present all of them, right, based upon the use case or needs to cross the org?
But, I’ve seen some traps laid as well, when you’ve got very astute or technical buyers that are forcing your hand to go far too deep to implement the product before they’ve ever bought it. So knowing how to have really good storytelling to give them credibility and confidence that you know what you’re doing, we’ll get to this point with the implementation manager, with professional services.
This is what this customer looked like. You look very similar to them. They’re very successful. This is why they’re successful.
So, I think it’s very easy to implement the software, especially with highly technical buyers before they’ve even bought, which is a trap.
Doug Landis:
It is a good trap. It’s a smart trap.
To be honest, as a buyer, you’re like, I’m just trying to throw you curveballs. How do you show up and respond?
It’s also a great opportunity to use story and to use narrative in the conversation.
And look, even when you’re scoping you can tell a story. And, again, throughout discovery, you can tell a story.
It’s a matter of knowing when to get into and how to get out of a story and looking for the signals.
Look, to become a great storyteller, just like doing great discovery – I use this loosely – it first and foremost starts with listening. You have to listen.
You have to be paying attention, to Brian’s point, taking notes, making sure you’ve done your homework. You’ve thought ahead of who’s going to be in the room? Who might show up? What do we think we are trying to accomplish? What might be important to everybody in the room? What’s our objective? Right?
I have this whole process called, purpose plan outcome.
What is the outcome that we’re all trying to achieve from our time spent together? And when you have been thoughtful leading into the meeting, then, my suggestion is, you also think about what stories you want to tell and to whom and when. We think about what product we want to show, how we want to show that, and what questions I want to ask.
I want to challenge you all to think about what stories are you going to tell? Because it’s that connective tissue that can pull together the questions you want to ask and even the product that you want to show. It can easily connect all that together and make things feel more, what I would call natural and relevant to me, versus it feels like you’re taking me through a process.
Brian Cotter:
Yeah. Just to Doug’s point, I one thousand percent agree.
It’s like, I don’t like giving people a list of 20 questions that they need to go do discovery on, because it’s going to be an interrogation. And I’m also not a big fan of scripts.
I like guidelines. I like flows. I like narratives.
But I don’t like on this screen, I have got to hit these four marks because, if you teach an environment of memorize and regurgitate, all you’re going to get is the same story over and over and over again. Versus creating a way to internalize and make it your own.
Like, hit this mark or hit that mark or look for this problem or that problem or this outcome or when a CEO says these things. It’s more or less the business acumen, the vertical acumen, or the unique environment of the product you’re selling and the problems you solve.
It’s less about the technology. The technology is the how – what we’re going to do or how we’re going to do it.
But I’m a big fan of Simon Sinek. People follow your why more than anything.
And if you have that purpose – why do you do this? Why are you going to buy? Why are you going to buy now? And why is this such a big problem?
You’re going to get to a more powerful story than if you get stuck in – what is it going to take to get the deal done? Or how is the implementation going to go? And the takeaway here is the AE’s answer the why question. The SE’s answer the what question and the implementation answer the how question.
Why are you going to buy? Why are you going to buy now? Why are you going to buy at that price point? It’s a joint effort to get to the why. Because if you get the why right, then you can say, what is the problem you’re having? This is what we might think the problem is, Doug.
And this is what the solution might look like and this is what we’re going to do and this is the outcome you should expect. And then to your point, Justin, about handing it down to the scoping, you then give all that information about the why and the what, and then the implementation team gets to answer the how.
This is the road map of how you’re going to be successful, how we’re going to guide you through this. And it’s just a mindset of a collective team that I call the five best friends and that is part of knowing your team.
The AE, the SE, the engagement manager, CSM and the value team member. And long ago, we didn’t have value teams. We had ROI teams.
But the point is you collectively are going there as a team.
And the more unified you are to that north star, that why you’re doing this, the better that experience is for the buyer. The more willing that they’re going to be sharing.
The more latitude you’re going to get to craft some of those stories that may deviate from the main reason why you’re there. So a lot to unpack there, but the why, the what, and the how are critically important for the way that we look at delivering something to our buyers, but also the way that we architect our teams to work together.
Justin McDonald:
I think it was a beautiful layout of the construct of the different roles and then their purposes and objectives of the how, the what, the why, and kind of speak to storytelling takes a village. Right? It really does.
The interplay between the AE, the SE, implementation services, it’s like revenue’s a team sport. Storytelling takes a village.
Doug Landis:
Indeed. It does indeed.
Well, since we’re talking about storytelling, can I add by the way, Brian, I love that why, what, and how, and who owns what piece of it? That is so great. If you’re a team of one at an early stage software company, then you’ve got to own the why, the what, the how, and it’s kind of tough.
But that construct is a really great way to think about what is it you need to accomplish in each of your conversations? Oftentimes, unfortunately, when we work in technology companies, we tend to focus too much on the what and the how.
Here’s what we do and here’s how we do it. And we forget a lot about the why.
So if you want to become a better storyteller, I’m going to leave you with a couple of tips here as we have a handful of minutes.
First and foremost, I want you to be really, really clear about the point you’re trying to make with every story. And it has to be relevant to the audience member that you’re telling the story to.
Secondly, you’ve got to understand the structure and the construct of what a great story is.
And Justin mentioned this before in the beginning, but at the end of the day, you’ve got to practice this muscle. You su*k at storytelling.
All of you do. I’m not going to lie.
You know, Benioff is a great storyteller because he practices like crazy. Aaron Levy practices like crazy. Obama practices like crazy. I don’t care who your favorite storyteller is. They practice like crazy, and they also understand what makes a great story.
Well, what does make a great story? Well, first and foremost, the most important element is you’ve got context to the story. So that’s a setting and a place. So if you’re going to tell a story, you’ve got to start somewhere.
Oftentimes, we just launch into the story. By the way, tip, don’t ever say, “Let me tell you a story.” Who cares? Just launch into the story.
But first thing, you’ve got to have a setting. Right? And so is that setting right now? Is this something that happened to you an hour ago? Is this something that might happen in the future? Where is that setting? Because that’s what sets the journey.
That’s why, you know: Star Wars, a long, long time ago, in a galaxy far, far away.
If you look at any story, there’s a setting.
Oftentimes, they go backwards. That’s like, we start today, but we’re going to take you backwards to how we got here.
So there’s a setting.
There’s characters.
So who are the characters in the story? Is it a story about you? Is it a story about Justin? Is it a story about Brian? Is it a story about all three of us? Is it a story about somebody else?
And then there’s usually in the story an “oh shit” moment. It could be a good thing, by the way. It could be that this amazing thing happened.
And then from there, is some sort of resolution in the construct of the story.
So it’s pretty straightforward.
It’s like, okay. So when someone’s telling a story, I want you to stop and ask yourself the first question.
When someone’s telling you a story, stop the story and be like, cool. What was the point of that story? I want to tell you what I thought the point of the story was.
This is a great exercise to do. Just have story time in your team meetings.
Someone tell a customer story, be like, cool. What was the point of the story? I’m willing to bet if you take one customer of yours and you have everybody tell a story, you’re going to get eight different points. And it’s like, alright.
Well, maybe you could do that with a story, but just be really clear, if you tell it this way, then the point of the story is all about implementation. If I tell it this way and I focus on a different character in a different situation, then the story is more about problem solving. Whatever it may be.
So exercise, get used to calling out what you think the point of the story is.
And if you’re telling a story and you got an important one to tell, go practice it with somebody and ask them. What do you think the point of the story was? And you’ll learn really quickly whether or not you’re actually any good at what you’re doing.
And then also be really clear about who are the characters? What’s their situation? Where’s the context? What’s my setting?
And then, by the way, every story has have an end, has to have an outcome. So don’t forget that.
Oftentimes, when someone’s telling you the story and then they kind of deviate – because we all have ADD, at least I do – and they go to another story. They’re like, what happened the last… what… where did we go? And then they go into another story and then another story, and they’re like, alright, this is fun for my ADD brain because I’m really active, but I don’t know, we’re not…
Yeah. Squirrel. What?
So, I think at the end of the day, it just takes practice. And becoming more acutely aware of what is actually a story and what is just a sequence of events.
It’s a very, very, very acute difference. A sequence of events is what we typically talk in:
This happened. This happened. This happened. This happened. This happened.
Or a whole bunch of facts.
Here’s what we do. Here’s what we do. Here’s what we do. Here’s what we do.
Like, alright. That’s not easy for me as a listener to really remember.
Brian Cotter:
Yeah. I agree with you.
I mean, there’s so many different kinds of story formats, outlines, and the way you should do it, like Star Wars, Disney, many different ways to do it. And, one thing I definitely want to just highlight is – Doug kind of touched on it – you never stop learning.
I mean, learning for your customers or your buyers, but also learning for different ways that you can actually get more information from them.
25 years ago, generative AI didn’t exist. Now I can do 80% of most of my work and research just by having the right prompts. But now I have to learn how to engineer prompts. The world we live in, you can get access to more information if you figure out how to unlock those secret areas.And that’s why I’d never stop learning.
In tying together what you just said, Doug, the thing that we kind of work on is framework, flow, and flash.
Once you’ve done your uncovering, you have a point of view, what is your framework? And I just view it as like an outline of a thesis in high school or college. You got a problem statement, you got some points, you’re going to deep dive, and you’re going to wrap it up.
In your mind, you have to think about it like a movie trailer. You have the journey that you want them to go through.
Then we go to flow. What is the narrative that’s easy to follow, easy to consume, and they can see their future on your platform.
But the key part of everything – and Doug you’ve made this comment – the flash. What are the 3 to 5 memorable moments that you need to leave with them so they sell on your behalf when you’re gone? If you don’t land that plane at the end of any meeting – when I say every meeting, I mean every meeting.
Because in every meeting, there’s only 3 ultimate outcomes. Decrease wallet share, running flat, or increase wallet share.
You have a 33% chance to land one point that someone says to someone else, “you got to look at these guys.”
And the framework, flow, and flash gives us structure about the outline, the framing, literally the flow, the narrative, and the flash – is why they’re going to buy from you.
And if you do it right, they will sell on your behalf when you’re gone.
Justin McDonald:
That was awesome. We’ll end on that because I’m not even going to try to come over top of you guys.
It was a fantastic way to end it. I have a feeling there may be some follow-up discussion and or a few blog posts from all the nuggets that you guys shared.
So, again, thank you enough for joining us. What a great layout of storytelling and some just amazing knowledge to share.
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