00:00 Revisiting the Sales Kill Box
02:39 The Evolution of Buyer Behavior
09:05 The Role of the Selling Sherpa
11:11 AI as a Selling Sherpa
14:47 Navigating AI’s Impact on Buyers and Sellers
20:11 The Changing Landscape of Buying Behavior
23:10 The Role of AI in Sales: Enhancing or Hindering Humanity?
27:08 AI as a Multifaceted Tool for Sales
30:04 Measuring Success: AI’s Impact on Sales Metrics
37:52 AI as a Sales Sherpa: Guiding the Buyer Journey

Jason Mlicki (00:01)
So Jeff, ⁓ today we are actually bringing back one of our most popular guests I think we’ve ever had. ⁓ And we’re both excited about it. So we’re going to revisit the sales kill box. So Maria Bolden is with us. She coined, I think she coined the phrase. Maria, I assume you coined the phrase, the sales kill box. ⁓ We talked about this three and a half years ago now, which I actually find really hard to fathom. ⁓

And in some ways, I feel like the world has changed so much in the last three and a half years. ⁓ In other ways, I feel like it hasn’t changed at all. And so I want to just kind of first off, let’s start with the biggest thing that changed, which is you’re not at Gardner anymore. So let’s talk about that. Maybe first thing we do. And then let’s talk about the sales kill box. And we’re to talk about AI and its impact on buying B2B buying and selling. ⁓

Maria Boulden (00:52)
We do.

Jason Mlicki (00:56)
Talk to us. You left Gartner, we’ll start there, and then we’ll jump in.

Maria Boulden (01:10)
It’s.

Mm-hmm, absolutely. Yeah!

I So I left Gartner in August of 2024. Probably one of the best jobs I ever had. An incredible company that treats its employees with incredible care and resources and really a great job that I absolutely loved with people that I adored. But I got to the point in my life where I…

I realized I was at Gartner for five years. I had only planned on two. I turned 60. I had hit the 45-year milestone of employment, and I was trying to manage my schedule one day to see my kids or even get to the beach with them. And I had a very full calendar to which my youngest son replied, Mom, why are you still doing this? How much do you really need after you’ve

Jason Mlicki (02:25)
you

Maria Boulden (02:26)
built the house you talked about for 35 years and can look out your window and walk to the beach anytime you want. And I couldn’t answer it. And life’s too short not to be able to walk to the beach whenever you feel like it. And it’s too long for regrets. So I made the decision to leave Gartner. And I miss my friends. I miss ⁓ the work we did because I was proud of it. I still do some of it on the side on a part-time basis for myself.

Jason Mlicki (02:34)
You don’t even have to fly to the beach anymore. you know, it’s…

There you go. You don’t even need the miles anymore. Okay, so let’s start with the sales kill box, you know, because this was a phrase that at the time when we were talking about this, we were coming out of COVID and you were talking about how buying

behavior had changed and selling behavior was falling behind. Sellers weren’t keeping up with buyers. ⁓ So let’s just kind of revisit that for a second. What is the sales kill box and

Maria Boulden (02:56)
But I don’t miss that full calendar. And I don’t miss an airplane, although I do travel occasionally for some of the clients I advise.

I don’t even have to drive

to the beach.

Jason Mlicki (03:08)
what do you mean by that? And

then I want to get into how it’s changed.

Maria Boulden (03:11)
But

I know I’m very pale, so…

Yep. Yep, yep.

you

So back in 2021, what I meant by Killbox was sending a 2019 seller into a 2021 buying environment. And it’s still a Killbox to send a 2024 seller into a 2025 buying environment. And yes, I did deliberately shorten that time window because the rate of change has continued to accelerate. But to me, the actual Killbox

is being toned after your customer needs, regardless of the reason.

That’s where it came from. It also came from, I had the privilege of leading a pretty broad swath of the DuPont sales organization. And part of that included the Kevlar business. And we were honored to hire a lot of veterans who not only served our country, but knew what it was like to wear the product and what it did. And some of them would talk about Killbox as a reference to what they experienced, but applied to a commercial environment.

Jeff (04:20)
Tone deaf, tone deaf covers many a sin in metaphors. When you say tone deaf, what does that mean to you?

Maria Boulden (04:46)
I took it.

Who? Who?

Yep.

It could be anything. It could be I’m too comfortable with my own skills to adapt them to the buying environment. It could be a leader who says this process works fine. We’re beating last year. It could be a CRO that says I can’t afford to restructure my sales team. Just get them, push them out the door and get them flying more. ⁓ It could be a seller that says I just care about hitting my number.

Jason Mlicki (05:26)
I want to hear you talk about that acceleration. You talked about, you know, use the 2019 to 21 and one, now you’re saying 2024,

Maria Boulden (05:33)
and I’m going to hit it and quit it. pick your pick. Could be any of those and could be others. to your point, it covers a multitude of sins and unfortunately there’s more than the ones I just rattled off. But bottom line, any seller that’s not laser focused on their buyer needs,

Jason Mlicki (05:33)
2025. I think what you’re telling us is that buyer needs have changed even faster in the last six to nine months than maybe they did in a two year window just a couple of years ago. So like talk to us about what’s going on there.

Maria Boulden (05:49)
whatever distracts them is a problem.

Yeah, and without question, they’ve accelerated. And frankly, if you’re thinking about buyer needs, zoom out, not just to the commercial ecosystem, but to overall business environment. I am big on scenario planning, and I do a lot of scenario planning and risk assessments with my clients. did a lot of it at Tupan, I did a lot of it at Gartner. I can’t emphasize enough how critical it is to do scenario planning.

and risk assessments in the current environment because take the many different factors that are affecting business conditions today, whether it’s geopolitical or other economies or some of the political nuances that are affecting a corporation’s ability to do business ⁓ globally. You know, we’re not all based in the United States and ⁓

a myriad of other things, whether it’s DEI related and how it affects our people or not. ⁓ There are a million things in our environment professionally, corporately, personally, globally that have changed that are things we can’t possibly control but affect our ability to do business, which affects our ability to commercially execute, which affects

Jason Mlicki (07:19)
So would you describe it as that buyers are distracted? Or is it more they’re they’re pulled in so many ways.

Yeah. Yeah.

Maria Boulden (07:42)
affects our ability to sell or buy.

think they’re distracted. I don’t think they’re distracted. I think they’re bombarded more than they ever have before, not just with information like they were when we talked in 2021 and 2019 and 2017, but bombarded with both information and shifting sand under their feet because of the conditions around them that are out of their control.

Jeff (07:54)
Yeah, you need to look no further than tariffs for, you know, chaotic operating environment. How many different scenarios would you have?

Jason Mlicki (08:08)
Well, that’s what came to mind for me too, was just this idea that like how much intellectual capital, Jeff, has been consumed in scenario planning tariffs, something that

wasn’t even on anyone’s mind, you know, nine months ago, and now all of a sudden,

Yeah.

Maria Boulden (08:29)
And dynamic.

Jason Mlicki (08:30)
Yeah. And so there’s all this gray matter kind of being deployed in a different

direction. So ⁓ OK. So ⁓ we’ve gone past information overload. That’s yesterday’s news. buyers were at information overload. ⁓ And now there’s just so many other things going on.

Maria Boulden (08:50)
And it’s not just supply chains,

it’s every function.

Jason Mlicki (08:53)
And as a seller,

you’ve got to understand that. You have to understand the context and all the different scenarios that the client is finding themselves in. ⁓ Let’s talk about this notion of a selling sherpa. This was actually a phrase that you coined, at least I think, in our podcast last time. You described yourself as much as a selling sherpa. What is a selling sherpa and what are we?

Okay, Brent, a Brent coin.

Okay, what was it?

Maria Boulden (09:38)
Yes. I didn’t. That’s a Brent Adams did.

So ⁓ if you’ve read the Challenger Sale by Brent Adamson and Matt Dixon, the concept of a sherpa was introduced there. what they shared, by the way, they have a follow-up to that book coming out in September that I can’t wait to read. But what they conceptualized in 2013, or what they shared, what they made clear in 2013 is because of this information overload at the time.

Because buyers were overwhelmed with the amount of things, information that they could consume online and from digital sources, they didn’t know how to sift through what was real, what wasn’t real, the many complexities they had to navigate. Buying groups had tripled in size. There was a sales process that, a buying process that looked more like a spaghetti bowl because so many…

constituents had a hand in the process and it was hard to navigate. So what the Challenger sale introduced was the concept of a Sherpa who could help guide anyone who makes a B2B purchasing decision to the type of decision that solves for a confidence problem. Not a confidence problem in the seller, not a confidence problem in the supplier.

But a confidence problem in the buyer and the buying company that says, not only did I make the decision properly, I asked the right questions, I analyzed the right risks, and I’m confident in the process I used to arrive where I am. That’s what a Sherpa does.

Jason Mlicki (11:09)
All right, so let’s talk about that. I know that the working hypothesis on this episode is, can AI be that selling Sherpa? And is it functioning in that way? I guess, what’s your take?

Maria Boulden (11:43)
Mm-hmm.

Well, you know, I think that begs the question of is it really helping ⁓ make things clearer? Is it just faster? Does it just pump things out? And I worry right now that it’s not necessarily making things clearer for most companies. In fact, Gartner Data, and I’m still a big Gartner nerd that loves the data they’re cranking out. Gartner Data shows that more than 75 % of Gen. AI projects will fail.

at least initially. So a lot of companies are claiming victory that they’ve deployed something, but do they know what they’ve actually deployed and what it’s doing for them? And frankly, whether it’s helping or not, I don’t want to poo poo AI. I see incredible potential. We all do, especially in the commercial space. there are a multitude, talk about bombardment. There are multitudes of companies out there selling the turnkey and solution and

I’m a little sus. And I think CROs should be too. And to be clear, I’m not saying the DIY version is good either. I think that’s fraught with risks as well. So I’m both fascinated by the use cases for AI in the commercial world and careful about how, where, and how fast I see it deploying when done right.

Jeff (12:56)
Ooh, how fast it’s being deployed when it is done right. Say more about that because I would think if it’s right, give me more, give me more.

Maria Boulden (13:24)
Mm-hmm.

Fair, but how do you get it right? So I, with all respect to C suites everywhere, you know, this is tough market and you’ve got to move at a pace where… ⁓

Jeff (13:43)
Mm-hmm.

Maria Boulden (13:47)
your customers and your company are ready for them. And I think there’s pressure on a lot of C suites from investors, from boards to get into AI. mean, arguably, whether it’s a public company or a private company, every CEO is saying, we’re in AI, we’re deploying, we’re in. Nobody’s saying, oh, no, no, no, I’m not still not sure about that. I’m not touching it. They’re all deploying it. But again, are they claiming that they’ve deployed it?

I mean, they’re even saying we’ve deployed it and it’s doing great things for us. Exactly what are those great things, not just articulated, but quantified? And what’s the data behind them? This is another area where I think people are claiming victory that they’ve thrown it out there. But is it really making a seller’s world easier? Because in 2024, believe Gartner did a study that said 72 % of sellers.

are overwhelmed by the number of skills, tools, and processes they need to do their job. So more isn’t better. Are we deploying AI to use as a tool or as a partner? And I worry that it’s a tool in a toolbox that’s already too heavy.

Jason Mlicki (14:47)
Overloaded toolbox, you know, I’m gonna go a little bit up script. I mean Do you get the sense that AI is having a bigger impact on the buyer or the seller? Is it changing buying behavior? faster or is it changing selling behavior faster or

Maria Boulden (15:13)
Mm-hmm.

that’s a good question. I don’t know. ⁓ I think everybody’s enamored with it. We all use it. And we all love when that AI agent pops up, whether it’s in Google or someplace else to kind of summarize that long list of things. And again, I’m not saying that’s a bad thing, but despite it speaking with conviction and carrying a lot of references,

Jason Mlicki (15:32)
Yeah

Maria Boulden (15:56)
The reality is there are very few LLMs out there that won’t give you something that’s either taken out of context or just not with enough data available to be right. And those kind of hallucinations lead us astray whether you’re a buyer or a seller. So I’m not saying not to use it. I’m not saying not to dive in and

Jeff (16:21)
That’s ⁓ the mentioning the hallucination to

Maria Boulden (16:26)
and talk about what you’re doing. But I am saying be careful where you deploy it and how fast you deploy it and verify the heck out of the output with something that you can actually use as a reliability indicator.

Jeff (16:27)
me is a great opportunity for both buyer and seller. Because if you’re talking about a Sherpa guiding people through the hallucinations, helping them delineate when it is a hallucination is an incredible opportunity. ⁓

But I wonder how many buyers are willing to be vulnerable and say, hey, this kicked out. I think it’s a hallucination. I’m not sure. And ask sales for support or for sales to be brave enough to say, dude, that’s a hallucination and you need to be really careful or X is going to happen. Right. And pulling back from a brink, if you will.

Maria Boulden (17:07)
Mm-hmm.

Agreed.

Jeff (17:26)
Mm-hmm. Mm-hmm. Mm-hmm.

Maria Boulden (17:41)
couldn’t agree more and some buyers aren’t doing this on purpose. They really believe it. mean, again, the ability, when you think about technology, this technology has been around a while. The difference that put chat GPT on the map and started this ramp of AI awareness is the conversational aspects of the outcome.

input that enabled a human coupling that we had never seen before. So buyers are reading something saying, well, this just assimilated the 50 different references that I pulled up and thought were relevant. And it did a really nice job explaining it and referencing the data. But again,

They’re not educated enough to know where the gaps are, or even what to ask or how to spot a hallucination. So this is no different than what we had to do in 2021 to help buyers sift through available data, be aware of the risks and misconceptions out there, and guide them as the sherpa to finding the best out

come for them, not necessarily for you because this is part of what we have to do as a Sherpa.

But what was basic math in 2021 is now differential equations in 2025. So what we have to be able to do is say, I understand what the AI gave you. And here’s the typical hallucinations and out of context output that we often see. Here’s what it really means. And here’s how it’s manifesting in the marketplace.

As a seller, as a sales manager, as a CRO, we are burdened with glorious purpose to do that homework ahead and be able to know where are those pitfalls. I know the buying journey well enough to know they’re going to run something in there or some, know, agentic AI is going to give them this output. And I need to be able to show them why that maybe isn’t wrong, but it’s not quite right.

Jason Mlicki (19:48)
Well, it’s funny as you’re talking, for about the last, I don’t know, 12 months, I’ve been trying to change the conversation with our clients around AI, because a lot of, in the world of thought leadership and marketing, a lot of the energy in the room went to how can we can use AI to produce

content faster, cheaper, quicker, Like it’s faster and quicker sometimes.

And I kept telling them, you’re having the wrong conversation because the conversation you need to be having is how is AI changing buying behaviors? ⁓ And what I think is fascinating is my gut says there’s a lot of firms. So 15 years ago, there’s a lot of firm leaders that I met that just couldn’t possibly believe their clients would ever use Google for any meaningful level of buying curiosity.

Maria Boulden (20:27)
Good.

Jason Mlicki (20:35)
And my hunch is there’s a lot of firms in the same boat right now saying, clients would never go to a tool like Chat Cheap BT and ask it questions and trust those answers. They would, of course, dig beyond the surface answer that’s provided and go deep into the sources. And I guess my take is that’s not true. And I’m just kind of curious. Well, I don’t know what my question is. think my question is essentially like, ⁓

Maria Boulden (20:38)
Oop.

Jason Mlicki (21:01)
How do you combat that? At least that’s what I see in lot of firms is just a reluctance to believe that buyers are moving to these new ways of learning and buying. Which means you can’t even arm your salespeople or your doers sellers or whatever model you use to have those conversations if you don’t believe them that it’s happening.

Yes.

Maria Boulden (21:41)
Yeah, this to me, this is an old answer to a new problem. And I’m going to sound like a one trick pony because any of my clients or anybody who’s ever heard me speak is going to say, oh my God, she’s on this soapbox again. It’s a buying journey issue. Where are your customers and prospects learning? What are they viewing? Where are they going? How do they make decisions? Where do they hit pinch points?

How do they learn about you? How do they learn about your competitors? How do they learn about the environment in which they are attempting to make progress? And as a commercial organization, as a CRO, if you have a privilege of leading the revenue engine for your company or any piece of it, you got to be able to know that journey with clarity. Because the minute it drifts or the minute it changes or whenever you have gaps,

Jason Mlicki (22:28)
I always try to tell my clients, be mindful of the canary in the coal mine. it’s every firm that I deal with, I can think of, they can reference at least one client that found them on

ChatGPT that said, oh, I did a query on ChatGPT and I found you guys. And that’s how we got working together. And I always say, that’s your canary in the coal mine. Yeah, it’s only one, but you don’t think there’s going to be more of them. You know that there’s going to be like five years from now, like, I don’t know, 10, the same way Google percolated the real thing. OK.

Maria Boulden (22:38)
you will have blind spots that you’re going to get surprised with in a not so good

Mm-hmm.

Jason Mlicki (23:02)
There we go.

Exactly.

Jeff (23:08)
So Maria, yeah. So in your mind is AI helping salespeople be more, not just effective, ⁓ more human or is it making them less human? Like, ⁓ chat GPT said, send the email that says this. I’ll just send it.

Maria Boulden (23:09)
For sales, that’s a bluebird.

Jason Mlicki (23:10)
All right.

Maria Boulden (23:14)
I didn’t create that business, they just found me on ChatGPT and I now have money on my cheat.

Let’s cap the quota!

Jeff (23:38)
and not thinking through the connection.

Maria Boulden (23:44)
Mm-hmm.

this is great question.

SUE!

I think right now it’s making sellers confused, sorry, or trust too much without verifying. I am hopeful that AI can really help organizations thrive by enabling human sellers to focus on the things that only a human can do. So freeing up sellers from the mundane and

Keep in mind, a lot of sellers find comfort in the mundane because they mistake activity for productivity. So, you know, it’s important to be focused on are they just busy or are they actually moving the ball forward? But the ability for an organization to free up time for sellers to focus on the parts where they can do what AI can’t do, and that’s be.

more human. AI can be very human. But the context, the humanity that your buyers are seeking and pulling the minutiae and the mundane away from the seller laser focus them on the parts of the buying journey that are fraught with risk for the buyers and where that decision confidence matters most aided.

with AI, aided with the information that it shares and the right data that creates it. Not to bombard, but to guide. AI will give you something, but I still firmly believe that as long as humans are still buying from humans, and there are lots of examples where they’re not, but in the places where they are,

I think it’s important to let sellers do what sellers do after they have been guided by the right data in, the right transforms to give the right information out. Let AI enable sellers to be more human. Right now, I worry, and every company is different.

Right now I worry that it’s just making sellers confused. Now there will be the 1 % or probably more than that out there that actually is using it to free up sellers time and to make them more effective and they’re claiming victory because they really are more productive and they really are more profitable. That message isn’t for you. That message is for the ones who still can’t figure out how to have a functional CRM.

Jeff (26:28)
But there’s none of those companies left out there. Everybody’s figured out CRM by now, Maria.

Jason Mlicki (26:40)
Sorry,

can’t laugh loud enough. So, you know, it’s funny as you were talking, I kind of want to run a scenario by you. It’s like, when I model out how all the different ways that we’ve explored using AI from a sales perspective, and I think about the ways you could use it, it seems to me there’s a couple of different ways you can think about it. There’s sort of like, layer number one is just a…

Maria Boulden (26:44)
And that’s the majority.

Next question!

Jason Mlicki (27:08)
is a research tool, a tool to do more research faster about a buyer and their needs and their priorities and decision makers and kind of get a dossier in place. Two is like an Intel tool, the tool that like, know, marketing automation always gave you this promise that you’d be able to know who was in the, who was in demonstrating buying signals, digital buying signals. And it’s always been kind of ridiculous because it’s never really worked, but I suppose AI should be able to really actually sift through the data and really tell you who’s got buying signals.

And then suppose third would be like, imagine, know, know, the, the pitch man or whatever, the QVC guy that used to sell on, sell a live television and he had a little earbud in his ear and they would, they would coach him while he’s talking like, well, this is really selling. So, so talk about this more. ⁓ move on, move on. This isn’t selling. They had real time data. So, so my thought is like, you could AI be the third? So what’s your gut say? Like is AI, which of those three things is AI best used for?

and a B2B selling environment? it the research tool? So is it a research tool to kind of make you smarter, an Intel tool to kind of just deliver you, tell you who’s in market, or the voice in your ear telling you what you should do, what you should say, when you should say it, how you should say it?

Maria Boulden (28:20)
Give me the three again, sorry.

Mm-hmm.

First of all, that’s not a choice I have to make because it can do all of those things. And this is going to sound like a wishy washy answer, but I believe in it. The answer to that is situational based on what the company needs the most. It could be one of the three, it could be two of the three, it could be all of the three. But it’s an it depends. If I were doing it, I mean, there’s a whole myriad of things I would do with it. But I would start small with things that I can verify and build confidence in.

AI is fraught with the same challenges that you have with any other ⁓ system or process, and that’s garbage in, garbage out. So start with something you can verify and validate. It could be pipeline, it could be CRM related, it could be data cleanup, it could be anything. I like using it, you develop something and then you put in ⁓ old data.

where you already know the answer, you already know how the market responded, you already know how your sales responded, and see if you get the same answer before you apply it to what’s coming. So I think it’s any of those three depending on who you are and where you are. Sorry, wishy washy, but I think real.

Jeff (29:42)
That’s a great, I love that answer because I think you’re spot on. And it really is, as you were saying, what you were saying, I had

this image of sales being, you know, three dance steps, if you will. It’s, it’s stimulus or catalysts, right? Something happens, response, and some outcome from that response.

And.

But no, ⁓ I’m, yes, yes. But we don’t want to digress into buyer’s journey and all that stuff because you’re spot on. ⁓ But what I’m saying is when you break it down, what AI is helping us do, and Jason kind of talked about this, is the intelligence. Who’s in market, who’s not in market, how are they responding, how are they not responding? And then helping us as humans respond

Maria Boulden (30:23)
There’s actually a lot of steps in there. I think there’s about 10 steps in there, starting with awareness and sending it all the way to advocacy. But yeah, let’s go with this.

Jason Mlicki (30:23)
I think she’s making fun of you

Maria Boulden (30:36)
Everybody makes sales and marketing so simple.

Jeff (30:51)
to that and is that encouragement or direction from AI making us more human, less human, more critical thinkers, less critical thinkers, more emotionally intelligent, less emotionally intelligent? It’s really, I think, important to understand because having that thing in your ear, you know, your brain goes out the…

out the window, you’re like, I’m not gonna be fully present. I’m gonna wait till somebody’s here. And then to your point you made earlier, there has to be some measurement of the effectiveness of it. Did you get to the outcome that helps the buyer make the right decision for them?

Maria Boulden (31:38)
Great.

Absolutely, and as a board, as an investor, as a PE owner, as a whatever, I’d be darn interested in. I don’t want to see activity. I want to see outcomes. And I think that’s, depending on your circumstances, that’s the question every leader needs to ask. Don’t pound your chest because you deployed something. Pound your chest when you can show with credibility and actual data that you made a difference.

Jeff (32:07)
So in your mind, what would the right metrics be in an AI world for outcomes? Do the outcomes always stay the same

regardless? Or are there some AI specific types of outcomes or measures that people need to be aware of?

Maria Boulden (32:35)
You know, this is a great question. ⁓ I think I’m going to show the fact that I’ve been in it. I am sure, I am sure there are AI related ⁓ measures that will show that it’s been effective, whether it’s some digital image that say a buyer engaged the AI suggested output and they actually followed or

⁓ went along the journey, did it shape the journey of the buyer as it was suggesting and guiding them to the human seller that shepherds them through the pinch point. ⁓ I’m sure there’s things like that, that very elegant, sophisticated companies can do. ⁓ I’m probably always gonna go back to the motherhood in apple pie that a

aged and maybe not as ⁓ edgy sales leader could do. ⁓ Pipeline metrics with obvious things like volume, weighted revenue, stage velocity, customer engagement, time spent for the sellers, you know, the usual leading indicator. I’m sure there are more elegant and more sophisticated ones than that. But if those, that’s as lagging as a leading indicator can get.

You’re talking about the leading, leading indicators. I’m not going to be able to articulate what those are without getting into a lot of depth with a specific company. But to me, if a company can’t deploy AI ⁓ in the commercial space and show with clarity that the pipeline metrics they use

to predict their success and potential pitfalls are better because of AI without overwhelming the sellers with information and that those correlate with top and bottom line growth.

Jason Mlicki (34:41)
Yeah. It’s funny because, you know, when we started this conversation, I think about, no.

Yeah.

Maria Boulden (34:53)
wait, I’m sorry to interrupt you, Jason. I’m sorry, one last thing. And they did do that in a way that shows seller time spend before and after deployment is improved. It’s less. Yeah, deal size, win rate, cycle time important. But did you just grind your sellers into the ground or is their life better, more effective so that they can go get more deals? Sorry, please go ahead.

Jason Mlicki (35:11)
No, where my head went as you were talking was, I wonder if AI creates the opportunity to actually

start to measure what you really wanted to measure. Because what you talked about in the sales kill box is the idea that we have to get buyers to the right outcomes where they’re confident that they’re going to achieve what they want. What do we measure? We measure pipeline and velocity. We measure our stuff. We measure what we care about, not what they care about.

Maria Boulden (35:40)
Mm-hmm.

Jason Mlicki (35:40)
So like

maybe with AI, it’s the chance to measure what they care about, indicators that they’re feeling confident about their decisions, you know, and getting to that place. So.

Maria Boulden (35:53)
totally.

I couldn’t agree more. And we’ve spent the majority of our time together talking about the applications of AI in sales and the commercial space. To me, we could spend triple the amount of time talking about impact on sales-related data, the role of sales operations, and the opportunity to really harness the power of data in a way that we’ve never

seen. So I, if you’re a sales operations leader out there, this is like Christmas.

Jason Mlicki (36:26)
Yeah. Well, what comes to mind too, is I think about what’s the, and you’ll laugh at this, know is I know you’ve seen

it. I can’t tell how many clients I’ve had firms where the pipeline turns out to be garbage. Right. And what, what is it? Well, this deal was $2 million. I got a 60 % chance it’s going to close. I believe pretty strongly we’re going to get this deal. They have no idea. They have literally have no idea. There’s making up numbers. Right. And, then whole I’ve seen whole we’ve had clients that almost failed because they had just bad data in that pipeline.

Maria Boulden (36:54)
Do it. ⁓

Jason Mlicki (36:56)
and

Maria Boulden (37:02)
yeah, the weighted pipeline is wrong. Marketing just, it’s like a bingo card. know, the weighted forecast is completely misrepresented. Marketing just dumped a bazillion leads that don’t really have any basis into the top of the funnel. And you’re just thinking, ⁓ bingo, you got all five. Yeah, no, it’s true.

Jason Mlicki (37:04)
Yeah!

Hahaha

Yeah, look at all these leads. We’re to kill it next quarter. ⁓ so I know where I’m going with this, Jeff, is I was thinking about just all

the conversations we’ve had with known well around client retention and all the intel that they’re bringing to that. And that same mirror on client acquisition and getting real signals, like, mean, real meaningful signals that the client really is likely going to hire you versus maybe someone else and not just the opinion of the practice leader who’s like, yeah, they.

We go way back. They’re totally going to hire us. They’re totally wrong. Or the random percentage. Yeah. Oh, 80 % chance of close. What are we talking about? it’s interesting. Let me stop. I’m taking us off track a little bit. But let’s start to kind of lean into a wrap up. I guess.

Jeff (37:52)
Ha ha ha ha!

Maria Boulden (38:00)
I hope your quote is not based on that.

Jason Mlicki (38:18)
You know, and maybe this is the logical question out of that whole discussion is, you know, if AI were truly our selling Sherpa, what would we be training it to do? Like, what do you think is the most important things that we should be ⁓ looking to AI for ⁓ if we’re leading a sales organization or we’re leading client acquisition at a firm? What should be the things we’re thinking about?

Maria Boulden (38:51)
Well, clearly, this is another great question. I think there’s at the macro level, profitable revenue growth is motherhood and apple pie. We know that. We are all under tremendous pressure to grow. And in the current environment, we are all under tremendous pressure to go grow profitably, because there are so many challenges to our profitability in the current environment. So

If I’m trying to imagine, that has to be the basis for all of it. If it doesn’t help us grow profitably, why do it? ⁓ At the end of the day, no matter how innovative we are, no matter how efficient we are, no matter how altruistic or sustainable or connected we are to our world, if we can’t be profitable doing it, we can’t continue it.

So, you obviously the underlying ultimate measure has to be profitability growth. But if I were to think about, you know, where do I want this? Where would I deploy it? What am I trying to be? My holy grail as a commercial leader or former commercial leader would be to have this, you know, dynamic customer journey map that adapts ⁓ the revenue engine in real time as it changes ⁓ so that any

places that manifest real-time as a pinch point or confusion or whatever, you have a means to both identify it and to do something about it. whether you decide, whether it’s digital or human AI helps you in that decision and is it virtual in person, know, help give the seller and the sales manager next best actions, recommend content, recommend no content, recommend guidance on how and when to engage.

How do I execute in this environment with that entity that either wants to buy from me or needs to buy from me and they just don’t know it yet? And sadly, some sellers need to hear this point blank, ⁓ stay out of the customer’s face, it’s not time to engage them yet. So I want that to be really clear and there’s probably, I’m sure.

I know there are systems that do that right now. And as I said earlier, there’s people out there who are already claiming victory. They’re leveraging the dynamics of the marketplace. They’re keeping up with them. But frankly, I would love something. And I think we’re all responsible to find this Holy Grail. I want something that accurately anticipates market shifts, needs, risks, pinch points, so that you get there ahead of them and be the sherpa.

and does it reliably all the time. And frankly, you know, to whom much is given, much is expected. So there will be times that your offering isn’t right for the customer. And AI should help us with that go, no-go decision so that we can truly be responsible and buyer-centric. That means you help the customer find the best fit for them.

And a lot of organizations feel too much pressure or too much personal ambition to do that. AI should help guide us on that decision, recommend the best fit for the customer and help the organization position themselves well for future sales, but maybe not this one. And last thing I promise, while it’s Christmas and I’m giving my wish list, I’d also like to see dynamic forecasting based on pipeline velocities as

customer verifiers of all and and frankly in a way that it also helps out the sales manager because of all the sales manager time studies I’ve done there’s only one thing that wastes more of their time than coaching and coaching is a big time sink that is often not effective that’s another podcast ⁓ and that’s forecasting

Jason Mlicki (43:07)
Yeah,

all the bad numbers we threw out there.

Maria Boulden (43:10)
That’s my Christmas

wishlist. And that’s what I think we need to be. Those are my expectations for AI.

Jason Mlicki (43:17)
You know,

as you spoke and you laid that out, Jeff, where I headed out listening to Maria was I don’t think AI is the selling Sherpa we’ve been waiting for. I think it’s the Sherpa for the sale Sherpa.

Maria Boulden (43:32)
It will never be a sherpa, but it sure helps a person. Well, let me put it this way. I see AI as a selling, as a, don’t say selling. I see AI as a sherpa in getting from awareness to somewhere, maybe a third of the way to advocacy. But somewhere in there, people will start getting confused.

And in those confusion points, AI might be able to help the buyer or the prospect through a third of them. But somewhere in there, whether it’s a virtual agent or an actual in-person or whatever, again, as long as humans are still buying from humans, AI has to be to be smart enough to the difference between I can guide the target through this problem or

I need to pull in a human now. And I believe it can do that. But again, garbage in, garbage out. We have to help it learn to do that.

Jason Mlicki (44:44)
Thank you. Great to have you back, first off. It was just wonderful to spend time with you again. really fascinating discussion, I think, for all managing partners, CROs, marketing leaders that are really thinking about this. And I just love the evolution of your thinking in terms of… ⁓

Maria Boulden (44:49)
Thank you for having me. I love talking to you guys.

Jason Mlicki (45:09)
how we’ve accelerated from a world of information overload to the seventh gear or something. We’re in a whole new gear of issues here around buying and selling that we need to think about and ⁓ how AI can hopefully help us. So ⁓ thank you. It’s great to see you.

Jeff (45:25)
Well, Jason

and Maria, I have to say I’m incredibly disappointed in this conversation because I really thought we were going to get to the point where I could just simply say, I’ll have my AI people call your AI people.

Jason Mlicki (45:32)
Thank you.

Maria Boulden (45:42)
You can, but mine aren’t returning any phone calls.

Jason Mlicki (45:45)
But why would we have people involved? Why can’t it just be your AI called my AI?

Jeff (45:50)
⁓ well, Maria, it’s been a pleasure again. Thank you.

Maria Boulden (45:55)
This was…

It is a privilege. Thank you for inviting me on. There are so many unknowns out there, but boy, it’s a cool… And it’s daunting, but it’s a cool time to be in the space. So, may the odds be ever in your favor if you’re out there deploying.

Jason Mlicki (46:12)
Yeah, absolutely. Well, get back to the beach. What are you doing with us? Fair enough. Fair enough. All right, we’ll see you, Muriel.

Maria Boulden (46:18)
It’s cloudy. ⁓

Thank you. No, I’m serious.

This was wonderful. I’d talk to you guys on a sunny day, too.

Jason Mlicki (46:29)
Well, thank you. See ya.

Maria Boulden (46:33)
Thank you.