99% of Deals Die From Bad Discovery (Not Bad Luck)

We've all been in that situation where we've forecasted a deal from someone else because of someone else's confidence and then something slipped. It has happened to every single sales leader out there and the rep is like, "Dude, it slipped. So what?" The rep doesn't understand that they're about to get their ass reamed by the board or by the CEO of like, "You forecasted this and you're not even close. Like too many eggs in a basket or whatever it is."

There's thousands of books written on the black swans and of the different landmines that can kill a deal and take it sideways. And you know what has never ever solved that problem is better damn notes.

So Woody on GTM Uncensored, we always like to start with a scenario and kind of put you in the hot seat, man. So I'm going to give it to you and would love your thoughts.

North Beacon Software closed about 40 deals a month. They have 12 reps. Last quarter, three of those 12 deals slipped at the final stage. Their VP of sales pulls guess what? Their call recordings to figure out why. And all the commitments are there. The discounts promised, the security review the champion said was already scheduled to take place. Competitor name that came up twice that we already overcame. But no one actually went back and looked at any of this since after the calls. So the deal slips, VP goes to the CRM, deal showing a negotiation. It doesn't say whether the discount was ever applied or not. There's no indication whether the security review ever took place. And the fix from the postmortem was quote from the VP of sales, "Y'all need to take better damn notes."

Now, you and I both know and Dale knows nobody in the history of sales has ever taken a damn better note. It does not happen. You ran sales team for over a decade before Ask Elevate. You've built a CI tool to handle this. You've watched this gap play out for years before you actually built something for it. What the hell is broken here? And where are you starting as a sales leader?

Oh my gosh, that feeling from the sales leader standpoint as well is just like heart-wrenching. We've all been in that situation where we've forecasted a deal from someone else because of someone else's confidence and then something slipped. It has happened to every single sales leader out there and the rep is like, "Dude, it slipped. So what?" The rep doesn't understand that they're about to get their ass reamed by the board or by the CEO of like, "You forecasted this and you're not even close. Put too many eggs in a basket or whatever it is."

There's thousands of books written on the black swans and of the different landmines that can kill a deal and take it sideways. And you know what has never ever solved that problem is better damn notes.

When we're talking about better notes, we're hoping for better insights. We're hoping for better signals. And we're somehow hoping that a note in Salesforce is going to make it so that I randomly see something that tells me that hey, this deal lost momentum or something happened.

And so the way that I start to solve it is obviously you should always do postmortems. Even with the best AI tools in the world, you're not going to win every deal. There is still something that happened. The question is, is it important to fix? You got to be able to take an L and be able to move on. If you can't move on on some deals and there's other problems now, for your scenario that you're talking about is like they actually were blindsided. There was something that happened that go through that. I'm going to talk about more of the principle behind it and then we'll talk about how people should be doing it.

One is understanding engagement signals. An engagement is a calendar event. An engagement is a text message, an email, a phone call that does or doesn't happen. All of those things can change the customer journey on how it's flowing or what's happening with it. And so at this company that you talked about, hypothetical company, it most likely was the person their champion was excited but they didn't have the right decision maker or the champion thought they were a decision maker and they didn't click in and ask more questions about what other decisions that person's made and have done on their own and gone through that.

99% of deals are lost because of shitty discovery.

And there's so many coachings and trainings that go on that, but people don't actually really, really, really click in to say, was the full discovery done to understand? They like, well, there's BANT. I put my BA notes in Salesforce, so I know they have. That's not even close. You have to actually truly look at all of those signals.

So what I would do, I would go look at the data. Now because of the tools that you know and Ask Elevate that we built, I already have all those insights and data and the second someone forecasts a deal where a deal AI is forecasting a deal, it's checking to see those black spots. It's checking to see did it go through DICTATE, which is the discovery process. We have a lot more letters than BANT. But Woody, all I need to know is do you have the budget? Do you have the authority? Like come on. BANT is such [expletive].

I'm going to go on a slight tangent here and Dale knows where I'm going to go, but I feel like of our 30 some odd clients we've worked with over the past 18 some odd months, what do you think, Dale? A third of them were on BANT when we started.

It amazes me how many people are on BANT. And it amazes me how when you get rid of the old school methodology from the founder who found BANT on Google or the legacy sales leader that has been doing this way too long and has never worked in the startup and has never changed and you explain other methodologies regardless of what it is, they're like, "Oh yeah, BANT sucks."

Mr. Founder, have you ever been on a call where someone's like, "So what do you tell me? Do you have the budget to approve that?" No one has budget. Budget doesn't exist. You're fighting for budget every time.

I digress and we could talk about DICTATE too, but yeah, BANT is a very sore subject.

The funny thing is is like when it first came out and when people start using it, it's these are things you should check, but it's like a level 0.1.

And I think one of the things that you were talking about, Woody, which I want to double click on, is the first couple of answers that you get can completely derail how you do a sales cycle. That's why you cannot create like a BANT or even like DICTATE or SPICE like they're guidelines. They're not rules. And so if we define these as rules, you're never going to get to the place of execution of them because you have a bunch of robots. You might as well have AI running all your discovery calls because it's like if you do this and you do that, like that just doesn't work because the little micro decisions that are made in that process could completely derail your discovery.

And so I think the first couple of questions can be scripted. It's like a football. It's like the first couple series of a football game. You can script those out, but then after that is complete chaos. The defense is getting better. You don't know what's happening on the field. And I think those are the parts where we lose it. And if we're trying to train AI or we're trying to train people to do these processes, then they have to use strategic thinking to say, okay, this is happening in this deal, in this scenario. Either I have a map to that or I don't. And if I don't, how do I get help from my leadership on this? I don't think enough sales people come to leaders and say, I need help with this, or enough leaders do enough coaching to get out why they have a problem within a deal. Can you talk a bit about that?

Oh my gosh, I love that you're bringing that up, Dale. There's something that happened and I would love if you guys know when I would love to try to put a timing towards it where reps got so afraid of their coach, like reps of their insecurity to go to their boss and say I need help so I can provide for my family so I can provide for your family. My whole job as a sales rep is to get everyone else paid. If I am doing my job right, the engineers are making more money, the CEO is making more money. Like you are in the most valuable spot and they're afraid to ask for help.

And so many leaders are not focused on helping them. Everyone else's job is to be empowering the sales team to go build more and get more revenue. That's why we pay sales people so much. You know, I got after one of my reps like two weeks ago. He lost a deal and I got after him and myself a little bit when I said like why did you not ask our CFO to talk to their CFO? And I'm like our head of finance, like when we they're running into some budget concerns, like why did you not multi-thread with our head of finance? And he's like, well, I didn't want to bug him. And I'm like the finance guy cares about money.

Every single one of our deal reviews and like as we're talking through it, it's like okay, not just how are you multi-threading? How is the us as a group multi-threading?

Working with the head of CS, my head of CS is getting a message, "Hey, I need you to reach out and become friends with this person." If it's a large enough deal, you multi-thread with the people and their peers in those roles. So I digress.

Reps need to be more confident to realize if they don't ask for help, they're actually hurting everyone.

And I think the sales leaders and the executives in the room need to be vulnerable and bring that out. They have to enable people to do that. It's okay to ask for help, not like pushing them down if they're asking for help. You should know that, and I see that happen a lot. Some sales leaders are like, "No, hey, that's your job. You should do it."

A good coach is not out there showing the quarterback how to throw the ball during the game. But it is like coaching them. "Hey, you didn't see that guy coming in on your left. We're going to have this person block over here, but watch this corner because there's a different vantage point from those leaders." But I 100% agree. Sales reps need to start asking for more. And so we actually put it in our one-on-ones where I'm asking them, "Who are the three people you ask for help from this week?" If they know I'm asking it, it just keeps it top of mind.

I love that. That's great. That's a really good question. How often do people have three people that they asked for help from? And how do you coach and instill that behavior? Because most sales reps, as much as they don't want to admit it, are very much lone wolves, and there's a fear of asking for help. I don't think it's a fear that they won't get the help. I think it's a fear that they're going to be challenged on what they're doing and they're not going to like those answers.

Usually, it takes the second or third time. The consistency and the questioning of them is actually one of the things I'm most passionate about. I think that's one of the things that I see with good sales leaders. They coach once, they don't follow through themselves. They walk into a room and they do an amazing training and then they go back and everyone does the exact same thing they were doing before.

It's annoying sometimes. I'm even annoyed. I meet with my team and I do morning huddles every single morning and I ask, "Did you do your 8 by 8? Tell them about your 8 by 8." Everyone knows that means before 8 a.m. you did your eight prospecting calls. Because if you don't start your day with prospecting, you'll actually have a worse day. So every single morning, tell me about your 8 by 8. Who'd you reach out to? How did it go? What happened? And every single morning, one person's like, "I got it done by 8:30." I'm like, "Okay, what are you going to do better tomorrow to make sure it's done by 8?" And it's annoying. I'm not going to lie. I'm sick of asking about it.

Yeah, and the consistency is important. If they know you're going to ask, you don't want to be the person coming in to say, "I didn't get it done till 8:30." We want to create all of these great AI tools and data pieces. In reality, we see the basic fundamental foundational elements are what will move the needle. This has nothing to do with AI. This has everything to do with human interaction and having a conversation. Because you're not saying, "Hey, put your 8 by 8 in Slack and I'll take a look at it." You're talking to each one of these people. Which in reality, at some point will not scale. You can't scale that as you get a big enough team. But if you push it down to leaders to then ask them how did your team do with the 8 by 8, and they're not answering the questions like that, then that structure and process needs to come out of Woody into the sales leader and down to the organization.

Take it for everyone. I mean, I'm even thinking of our own. So Woody, we have an internal working on the business meeting every Thursday. I'm literally sitting here thinking the first question we should ask ourselves is, who are the five companies you've prospected this week? You, me, and Jake. All of us. Because it's the accountability. And I won't speak for Jake because he's not here. I will speak for Dale because I've known him longer and he's here to refute it if I say otherwise. Neither one of us would want to get up in front of our two partners and be like, "Well, I didn't have time or I didn't." Like, I can't imagine looking Dale in the eyes and being like, "Sorry, it was too busy to grow our business."

You're right. That's a dead answer.

It's so important where you kind of force those things. And we should do it for ourselves. These are the three things I do every single morning huddle, and then I'll talk about the one-on-ones. The questions they're going to get is, tell me about your 8 by 8. I don't care if you're an AE or an SDR. Get your ass out of bed. I hope they listen to this because I'm not embarrassed about it. We had someone quit because they got sick of it.

Great. Wrong environment.

Yeah, they literally said the morning huddles are too intense. I said great. And so they went to a large company where they're not going to be managed and they're

Oh yes, where you get managed by spreadsheets.

It's 8 by 8 every morning. Goals, gratitude. Goals for the day, goals for the week. Always goals for the day. What does a great day look like? If you can't decide before 8 a.m. what a great day looks like, you're not going to have a good day.

I agree with that 100%. Dale actually taught me that. By 8 a.m. you did eight prospecting calls or eight prospecting things. Right now they're LinkedIn messages or that's where most of them are. Then there's the goals and then gratitudes. We have to stay humble. We have to know that we are in the greatest country in the world. We are blessed to walk into an air-conditioned building that has a golf simulator, that we have free energy drinks. My car drove me to work and I got to listen to an audiobook. I got to work out, eat a full meal. We have to stay humble and people like to buy from humble people.

I love that. I talk a lot. I travel a ton, right? I've done Thailand and Vietnam and, you know, even when we go to bigger countries, we try to go outside of the cities. And I tell my kid all the time, we're doing Morocco in December. You don't realize how good you have it. You are an upper middle-class white kid who lives in Wellington, Florida, dude. Which is Palm Beach for everyone listening. You don't realize how other people live. And I think what you just said is so important. Whether you're that 15-year-old kid, the 30-year-old sales rep, the CEO of a company, we all have stuff we're dealing with, right? Is sales and business and everything hard? Yes. But at the end of the day, I know where I live. I know where most of the people I work with live. You are not living in a 12 by 15 non-air-conditioned box with your toilet, your mattress, and your stove next to each other. You hit the nail on the head.

I want to shift gears. Right now, everyone's AI pitch is the same damn thing. Your own launch language says, and I'm pretty sure I'm quoting here from my research, "AI should empower customer-facing teams, not replace them." Every vendor in this category is saying somewhat the same thing. Other categories, you'll hear people—I forget the name of the company, Dale, I don't know if you remember, or Woody, if you know, in San Francisco—they actually have these big giant billboards that say "AI should replace your people." How do you stand out from everyone else who's saying this and actually do it differently where we are empowering teams and the goal is not to come in and say we're going to replace your seven of whatever name your type of rep here?

This happened with every new technology that comes out. There's a lot of people trying to figure out the right way to say it. It's been really cool to watch us and other companies where we launch a page, then two days later they launch the same story and I see someone else say something. I'm like, "It's actually pretty good. Let me see how I can bring that in." So I think it's been really hard. Where we've been winning it starts off with the right customer support, the right customer success, the right conversations where we don't have AI SDRs every single message, every single thing we do on LinkedIn. Yeah, there's things that we do to have AI make it a little bit easier, but we are humans talking to humans. And I think they see that in a lot of just the branding, not the story, but the feeling as people did it.

We just redid a brand relaunch. I literally looked at every single one of the AI companies in our space and they were this blue, purple blur. I was like, "How do we go the furthest away from that?" So we went after more human colors versus this futuristic astronaut in the sky feeling, where it's like, no, people are looking more for that grounding feeling.

# Transcript

Went from the elephant to the tusks, too.

That's actually a funny story. When I started the company three years ago, it was actually October of 2023 when I was picking my first logo. I hired someone to do it, and then like a year ago, someone sent me something like someone else owns that logo. I paid for that logo. It looks like they didn't, though. I had to switch. I was like, "What a waste of time." That's honestly where we start.

Now, when we talk about the technology, even though the word is "Ask Elephants," where you can come in and ask it anything and it does all those other things, it really has been where it's more proactive and where people are not having to think about what to do next or how to do those things. And yes, it automates admin work, but that automation—that's not AI. AI is part of the automation for them. It's really about being proactive. How do we make it so that they ask themselves a question? And Ask Elephant is more about us asking you questions than you asking it questions.

So that's very interesting, and I've been reading a lot of articles around how AI is making us as human beings dumber. Because you're surfacing these things and going back to the earlier conversation of like, when you get into a sales motion, like after the first couple plays, there's many different directions it can go. Are we now taking away the ability for the sales rep to have those conversations because we're surfacing them proactively through an AI tool?

What we have seen is that one of the things that are proactive is like after a conversation is happening, we have an agent, and anyone could do this. You could take the transcript, you could build out a workflow that then has the methodology included or whatever it is. The technology makes it so everyone can now do everything. It's just who's going to maintain and get those things up and running.

We do a deal intervention where we Slack the manager and say, "Hey, Dale, Adam just had a call with this. He missed the opportunity to connect with Beth this way. Here's how you can coach him." And every single week we're hearing about people who closed additional deals that would have silently died because they didn't have AI watching the humans to get the human in the room with the right information at the right time so they can do that coaching. They can step in and do that.

I love what you were just saying. I just want to ask one question here. Would it be more viable? Would it be more the ability to make people think more if Ask Elephant would send a note out and say, "Hey, Adam just had a call. He missed X, Y, and Z. How would you go about solving this?" Because it sounds like we're identifying it and we're trying to solve it for them without having them think.

You know, that's a good question. The thing that we're noticing is actually causing a different issue where people are experiencing notification fatigue.

One hundred percent. They'll just ignore it. Most of the time, it doesn't matter if you're like, "Hey, your house is on fire." They're like, "Ah, it's fine. Someone else will take care of it."

So we do ask a question at the end of all the things like, "Hey, what would you do here?" But we do guide them maybe too much. But they still have to then go execute. They still have to then decide how to do it. Adam could have won this deal or didn't discuss this customer's pain the right way. Dell now has that coaching opportunity. We're telling the manager, "Hey, this is where Adam needs to be coached." I think that is super important because we will not ever have time to go through every rep's calls and find out all the things. That's where Gong failed when they were building out their thing. There's a hypothesis that people are going to go listen to all this stuff. So I think surfacing that part up, but then we have weak sales leaders across the board. So are we creating weaker sales leaders by surfacing like "you should go do this" versus "here's a problem"?

Are you taking the critical thinking out of it?

Well, yeah. You have to respond to the AI now. The AI can learn on how the human is thinking through the process. And if you don't do that, then it gets escalated to Woody because I, as AI, asked you the question, but you didn't answer it. And now there's an escalation process.

So when I think about implementing AI or any kind of automation workflows—I mean, a lot of what we're calling AI, they're not AI, they're automated workflows. This has been a problem for a long time. I do believe we're getting to some generalized AI pieces, and I do believe that's happening. What we're not identifying in any given structure is what the human should be doing and what the AI should be doing, and having clear delineation in any given task for that to happen. So now we're just saying the AI should take care of it, and we're cutting the human out of it. So I don't know, it's something to think about.

I know. I love that thought process because I now can think about more things because I can have more lanes going, and then when I need to, I can go deeper in something. And our AI that we use, we use something called Grill Me, where it's like it asks you questions until—and sometimes I get annoyed because I'm like, "Dude, we're on our 30th question." The most important thing is to not stop thinking, but to have it help us think.

Right? You have to have AI as a thought partner and not as the thought leader.

Here's something I keep seeing with sales teams I work with. Generic sequences don't work anymore. We've all gotten so good at tuning out the noise that even your own buyers are ignoring you. The problem isn't your reps. It's that your sequences are static and your signals are somewhere else entirely. That's why our clients use Nooks. And the thing that stuck with me is that their sequences actually stay fresh because the signals update them automatically. Right buyer, right moment with no manual babysitting. If your outbound feels like it's shouting into a void, go check them out at nooks.ai. AI back slash bridge the gap.

Can I piggyback on that for a second then? Because I agree with you, but let's use a real example, one that's super common with CI. So churn alerts, right? Woody, I would imagine Ask Elephant has a way to capture churn alerts, capture a risk signal likely weeks before some human's going to notice it. Maybe they go into Pendo and look, maybe they look at account stuff. All of that's great. So the rep or the manager, they get that alert. They do nothing with it and the account still turns. How much of the tool, how much of AI, still depends on the person doing the thing that you, the AI, Ask Elephant, Gong, whatever the hell it is, just can't control? I think that's the part that Dale said is like it needs to say, "Hey, this human didn't do the thing. We need to now notify the next human. This human didn't do that thing. We need to notify the next human."

Are you guys doing that? Not to put me on the spot, but I just haven't seen them with anyone yet.

Yeah, we do it for some things. I wouldn't say that we're—I just don't think we've built the entire workflow. Like, I think we've built fragments of workflows, but we haven't brought it all the way through that process. And so I don't think it's a matter of if we can do it. It's a matter of have we thought all the way through it? And if we thought all the way through it, where are the gaps in it so that we don't lose the strategic thinking part of this process?

There's a really interesting thought of what parts should you outsource and what part should you retain. I actually outsource a lot of research. I outsource some thinking in some areas, but not the strategic decision-making. I need to prove myself. I have AI always argue with me. I tell mine to be an ass. My favorite thing is "You are the devil, and your job is to make me feel like shit."

Your AI's name is Dale.

Devil.

Wow. Dale. He cloned you, my friend.

Wait till I show you the skill that I created.

And that's what it should be, where you have it because AI wants you to keep coming back. So it's going to try to give you answers to make you feel good. Your job is to make it so that I actually know what I'm doing, why, and why I'm doing it in all of those things. So why is something a good email? Why is something the right thing to say? Why was that a good discovery? Why wasn't it a good discovery?

And so when we look at like, when right now people think about updating their CRM, like the notes, just like how Adam started the conversation, it's like, "Well, I want to have medic updated in Salesforce, so I will never go read it." And so like, that to me is just like the biggest problem because it's now just more data that doesn't actually get used. Even structured data that's not taken action off of is usually wasteful. And so every single thing we do is first we have to score it, and then we have to justify the score. So when we're talking about a discovery score, that's not just looking at one transcript. It has to look at the whole thing.

Experience, the whole journey of the customer that then can be able to give you a score and then it says why it will happen, why it won't happen and it starts to have those different things. Now the thing that we're still struggling with, Dell, and I'd love for you to tell us how to solve it is humans are still the spot where it's failing.

That is such an interesting comment and I'll tell you why. So we're just doing a GTM audit for a client yesterday and we were going through this process and the client said it's the humans that are failing us. Like we are moving into an AI world but it's the humans that are failing us in the process. My hypothesis is two things. One is we haven't built out the entire jobs to be done and identifying the jobs to be done by the human and the jobs to be done by the AI. So we just start putting all of the jobs we've done on the AI and then the human is an afterthought. So I think we need to flip that and find out what parts of the AI can help the human. The second part of it is the data part that you were talking about. Yes, we have way too much data happening. The bigger challenge is how do we get the same data structure or the same data components digestible by different constituents. So the salesperson needs the same data sent to them in a chunk of digestibility that they can work on. The sales leader needs that same data probably elevated and chunked in a different way for them to digest. And then Woody as a CEO needs the data from the sales leader plus maybe something from the CS leader to then make a different decision. The data is all the same. It just needs to be chunked and digested in a different way for each of the constituents. That's the problem. And that's why I created Ask Elephant. When I was running Divvy and then Bill, like I had 350 people on my team, you know, I had five VPs that were over, you know, all these departments. And so if I had a question, I'd Slack someone who would Slack someone who would Slack someone who would then make up an answer who would then Slack someone else that would filter it because they didn't want their rep looking like they messed up, that then would send it to someone else. That person would be like, "Ah, that's probably not good enough." And they would maybe add some little things. And now we're playing the game telephone and we're making billion dollar decisions off of telephone.

Whatever you said in the beginning is not what ends up on the backside. And so because there's political things and landmines that happen inside of organizations, and so that's why a lot of times we get brought in because we don't have any political affiliation on any side. And so that political affiliation will taint the information that's coming through. Once again, we have the data. The data isn't the problem. It's the digestibility and the framing of the data that we always change up when it comes to making decisions. We're human beings. Like back to your gratitude conversation, we do not want to be called out on our mistakes. And so without wanting to be called out on mistakes, we will defend it and we'll say, "Yes, this deal is stalling, but I spoke to them. I texted them. They told me they're going to get it done. They said the decision maker..." And then like no one coaches them. It's like, "Okay, like let's go through the email that you sent them." Oh, the email you sent them says just checking in. Well, okay. That's not an email. There's no value exchange in that conversation. Dale, I just wanted to follow up and make sure that we're still good to sign on Monday. 100%. Right. And so us as leaders, back to the strategic thinking pieces of this because this is very interesting and a full circle moment, AI would tell us to then follow up, right? So send them a message, follow up with the customer, and it's like, here, put this information in the email, and hey, ask them like, send them this marketing brochure, slick, because they're in stage three of the funnel. Now all of a sudden, the salesperson's doing that stuff. You look at the email, it looks AI written. You have content in there because no one's strategically thinking, how do I actually deliver value at this stage in the sales process to someone that wants to buy from me? We're automating too much.

We are automating too much of that extra thought process of like meeting the customer where they're at, where it's adding them value to get them to their next step because I have never bought a car or a software in a discovery stage, a demo stage, a negotiation review stage. That's not how I buy things. It's so interesting that we try to force customers into our pipeline. It's a completely wilderness map that you have to go figure out where they're at, figure out where they're trying to go, and then help them get there.

Let's switch it up just a little bit here. So you've run 500 plus teams, rating 5.0 on the HubSpot marketplace and 100% growth quarter over quarter off of a six million dollar seed round. Other big players are racing towards a similar market. What does a winner have to do like above the other ones, the other ones that aren't going through this process? Because there's so much of this happening. Back to the information that we were talking about earlier on the messaging side, how is that differentiation happening?

Something that I'm constantly questioning myself on is one, we are seeing more and more markets that are breaking out to be smaller teams, smaller companies, and like there's like a lot more people. And something I'm actually very mindful of is, is there going to be one or two massive companies and then a bunch of tiny ones or is there going to be these other companies that go in and like we're going to have multiple billion dollar businesses in certain spaces? And so I believe the first most important piece that everyone is racing to is making sure that they capture the data because your AI and your insights are worthless without the data. And so there's going to be a lot of competition there. Every single person out there is going to throw together some sort of data capture tool that I can capture the data. A lot of them are then doing weird context stuffing where they're like the AI will just structure it. They're not thinking about actually how to structure data. Ask Elephant from the get-go, we were built off of the concept of building a structured data layer where we interrogate based off of a lot of deterministic things with a lot of AI to structure the data so you can actually get the same answer every single time. I think that's a smart move. I do believe a lot of people are racing to the wrong thing and so it'll be interesting to see the evolution of this process because philosophically I believe go to market decisions, any decision—forget about go to market for a second—decisions are made of a million micro decisions that generate a macro decision. The problem is no one remembers all the micro decisions that are made when the macro decision gets deployed. Then six months later you have another macro decision you need to make—messaging, ICP, new feature, whatever it is. It's like finding the email. It's like you're going through that process all over again. But you forget that you went through all these micro decisions. You made the decision, the best decision you can make at the time based on all those micro decisions. But then when you get to the next level, you're going back through all those micro decisions again. How do we get into a place where all the micro decisions are informing that we made this macro decision because of XYZ micro decisions today? We still have that intellectual knowledge and the time has changed, but the new decision—because we didn't make that micro decision before, we want to make that micro decision now to make your macro decision better. That's where I think this is going to happen.

So that's why I called it Ask Elephant for a reason because an elephant never forgets. And so we actually never built a data table. We built a memory graph. And so when people like, when you think about CRM hygiene, it's CRM data, where it's like that's actually one of the main reasons why people buy us is we actually have to have a translation layer from our memory graph into their data table. And it's not like a RAG system. It's not like all those other ways where they're just context stuffing and hope they can find it. Every single thing on that memory graph knows where it came from, why it came from, if it's still important, how long it matters, and then it can trace itself back to where it has those relationships between the other data that it came from. So when we interrogate a single email into right now, it's over 1,600 endpoints and that has a memory graph of every other aspect of it. If it's the first email or if it's the hundredth email, that memory graph is slightly different. When you're actually thinking about how we're going to work alongside AI, that to me is where there hasn't been a winner yet. I can record calls, I can take notes, I can connect my notes and transcripts to Claude that helps me make a decision, that coaches me on a call. But we use Gong as an example. We integrate with them and we also sometimes replace them. Gong's been around forever and they're a great integration, but it's like I need to know that who was the person that brought up Gong? Did my sales rep bring up Gong? Was it their sales leader that brought up Gong? Was it the RevOps person that brought up Gong? In my HubSpot...

Or my CRM, it might say competitor Gong. That doesn't tell me who brought it up or why they brought it up. Are they looking at contracts because they're frustrated about pricing? There's a thousand things that are related to that single data point. Context is where the future of AI is going. So when we make those micro decisions about, hey, we're competing against this person, how do we win against them? It actually can answer it. It should take out the guessing.

We are running on a clock. I hate it because I could go for hours. I want to switch gears. We're going to go triple M: Monday morning move. Practical takeaway. Listeners can test this week starting Monday. And your job, Woody, is to tell me what you'd add, change, or push back on, and tell me it's wrong. That's fine, too. Dale does it every single day. So here it is.

Open your CRM. Look at your last 10 closed won deals from this quarter or last quarter, depending on where we sit in the quarter. For each deal, check the actual next step from the final call, the economic buyer's name, your sales methodology fields, whatever that is, and most importantly, the specific reason the customer said yes. Now, what you're looking for is not the field from memory days later, but what was actually said on the call. Now, as the sales leader, I want you to go back and check the accuracy against the deals themselves and what you know from your handoff and the conversations you actually had. Figure out what's accurate, and now look at what else you can autopopulate so that your team can start driving deals consistently in the right way and your reps can focus on revenue-generating activity versus going and putting in their notes four days later when their manager tells them that the fields aren't there. Implement that. Thirty days later, go look at what your pipeline reviews actually look like with real data instead of remembered data.

There's a lot of those things that I believe—I don't know if Dale's going to agree or not—but which part of that should be automated because all of those questions, you don't want a human to put it through their lens. Now, the thing that I love about that is where AI can automate the fields, it's actually having more people stop and think through those fields. I'm actually more focused on having a battle room where you need to rearticulate and convince a group of people why that person bought. Who were the other people there? And actually, a deal review is no longer, where is it at? What's the next step? A deal review now should be more about why. Why did that person look at our website? Why did that person come in? Why did that person bring in the RevOps leader versus the CS leader? Who was the champion? Why were they the champion? Who was the decision maker? Why weren't they the decision maker? That process is going to make the human think more. That process is going to have them show up and be more aware of when they go onto that next call of how other pieces work together. As much as we do with updating the CRM to give you a pretty dashboard to help you with forecasting, as humans, Monday morning, start asking why. Why did that customer buy? And that is where a human working with AI can get those answers faster. But if you can't argue with someone and convince someone else on your team why it happened, then you actually don't understand it. And so spend your Monday mornings understanding your business. And I believe the best way to do it is by trying to convince someone else why something happened.

I love it. I love it. Good pushback.

That's what it's for, right?

Yeah, 100%. We need to help people become better at sales, go to market, et cetera.

We did a training yesterday. We do a tape teardown where we bring a call and we go through and we are pausing it and talking about why throughout our tape teardown. One of the persons that started—it was his second one. He's like, "I've been doing sales for five years. I've never done this. I've never had a group of people go through and rip apart a call. It has to happen." Like, these are the things that are non-scalable that need to happen. And what I always call sales 101. This has been forever. This has been done 20 years ago.

This is called coaching.

Right?

We've done call teardowns forever.

We do managing.

Awesome. We need to wrap some stuff up. So let's get into some uncensored questions here.

All right. So we're going to do some GTM uncensored questions. Woody, what's the most expensive mistake a sales team makes with a tool in conversational intelligence? The one that shows up on the invoice but actually never gets its own line in the postmortem. The reality is most tools are bought like someone has a problem. They're not implemented to actually solve the problem. Every tool out there is probably only being used 10%. Like, I made that number up, but it is so low.

It's low.

It is so low. And so the thing that you have to actually look at with implementing any tool is one, don't buy a tool because your boss says you need more AI. Actually say, what am I trying to solve and can we solve that thing? And then to be able to work on it, the most expensive mistake people make is they are using a tool 5% of the way and they are not trying to actually solve problems. They show up to work to try to not get fired. So be willing to get fired, fail faster.

Awesome. If you had to kill one feature in your product permanently today, which one would it be and why?

You know, we're actually going through that exercise right now. We had something that was like a knowledge base where you set up a custom agent that had a knowledge base. It didn't get adopted. We're going to deprecate it. People can ask Elephant anything. So it shouldn't be its own feature. It should just be where you can ask a question. And we're recognizing that customers want to say they do it, but they're not doing it anyway. So we're trying to find other ways to be more proactive of that. But that's one of the features that just didn't get adopted.

Woody, you've built a couple companies now. What's the thing about building—and I'm going to use this term broadly—revenue automation company that no one really talks about publicly because it makes the pitch seem much harder than it actually is?

One, selling to salespeople sucks.

And we don't talk about that. We know we have these problems. When we were reps, we did one or two things slightly different that made it so we were good at it. But if we actually stop and look at it, sales is not a problem that needs to be solved. And so when you go after the full revenue cell thing, you accidentally get stuck between I need to help the sales rep, I need to make the manager feel good, I need to make the RevOps person feel like they can implement it and they have control, and I need to make the CEO feel this way as well. You just don't think through all of the people that are touching it when you start it because when you run a sales team or when you are a sales rep, it's like, I have this problem, I need to solve it. And most companies are not buying tools for their people. They're buying tools for themselves. I'm fighting like hell to fight for the front-line guy because they deserve to have tools that actually help with it, not make their RevOps person babysit them.

This one's super easy. Last one as we wrap up. Dream vacation destination.

I live here. Utah has the best places to visit. I can be in the desert.

Most underrated state in the country.

Well, don't tell people that. Don't move here. It sucks. We're always on fire. If you literally look at every single weekend, I'm within two hours of my home and I'm in a completely different climate doing something completely wild. So my favorite place is where I live. This weekend we're going boating up in Eden, beautiful mountain, small town, not that many people. And that's where we live. I just booked Utah for spring break this year for my kid because he loves to ski and I love Park City.

Hopefully we get to go back there soon.

Yeah, let's hope so. You know that story with the pivot from last year. Woody, Ask Elephant, thank you for joining the show. Thank you for dropping your knowledge. Thank you for sharing. Y'all go check out askelephant.ai. Look at those cool little tusks. Look at the platform. They're doing some cool stuff over there. Woody, thanks for joining the show.

Hey Woody, thanks, D. Thanks, Adam.