Hall of Fame: Kevin “KD” Dorsey Ep. 8

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Everybody. And welcome to this episode of 30 Minutes to President's Club. My name is Armand Frohk and I'm here with my co host Nick Sigelski. Today we have the one and only KD Kevin Dorsey, inside sales top 10 sales leader, sales Dev Exec of the Year and currently VP of Inside Sales.

Over at Patient Pop Over.

A legend in the SaaS sales space. Nick, why should people listen?

Armand, we got a clinic today on really good questioning skills, which is where we spent most of the episode. But Katie's also got a pretty cool take on why understating your value and backing off actually can make you a more effective salesperson. Let's get into this thing.

Awesome, guys. Killer episode for disco and for cold calling. Three, two, one.

Roll it.

Today's show is brought to you by Outreach, which helps you increase seller productivity. Coach calls more precisely and forecasts more accurately using a platform powered by AI agents. If you're running a tape review, you're going to stop at three different points. Number one, when the prospect monologues ask your reps what did we pull out that was important? From there, ask your reps what should we say or ask next? And then click play and recap what did the rep do versus what we thought they should do? Our friends at outreach built a 30 NPC resource hub where you can grab this play and an unreasonable amount more links in the show notes Today's tactic is brought to you by Attention which uses AI to capture all of your sales interactions. Automate sales busy work like CRM updates and flag hidden deal risk. So if you want to avoid ghosted deals, end every discovery call with these three questions. Number one do you want to buy AKA validate if the deal is real? Number two when do you want to buy? Validate if it will close this year. And then number three how do you buy validate that they will get you in front of power. We put together a guide on how to unblock the three biggest deal blockers in your pipeline. There's a link to get it down in the show notes.

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Kd, welcome to the show. Every single show starts with three tactical actionable tips. Let's get your three. What's number one?

Sales reps. You gotta talk to more customers. You have to talk to more customers, not prospects. So every rep that I have, we do this onboarding. You have to talk to customers, ask them a bunch of questions. I'm gonna give you three real quick. Why did you buy the product? How would you describe what this product does for you and what were you afraid of before buying? You'll learn a lot on how to do better scripting if you answer those three questions.

What's number two?

Number two, something I really love to talk about is eight miling objections. So this is something that I've been teaching for a while now called 8 Mile. The objection, if anyone ever watched the movie 8 Mile of Eminem, his final battle round is the epitome of how to handle objections. And he spends 45 seconds saying all the bad about himself that the other person could say. It takes away all the power. Eight miling works the same way in sales. If you're afraid of an objection, be the one that says it. It keeps you in control and takes the sting away from the prospect.

Great. Round us out. What's the last one, Katie?

So the last one is have better problem based questions. So this comes from the interviews that you do earlier in terms of learning what problems your product solves. But stop asking discovery questions, or even worse, qualifying questions to your buyers early on. Ask them problem based questions that exposes a problem that they maybe didn't have. So asking them how they do something that you know they can't do exposes a problem. And it also makes you look like more an authority to them when you're talking to them.

One thing that I'm still hung up on is oftentimes you start a call asking basic situational questions, right? How many people are at your company? How many people do you plan to hire? And it's tough for someone super junior to just jump into, like, are you going to miss your targets? Does this mean you get ousted by your board? So how do you make that transition? Especially as somebody who might not be an expert in the space.

I believe in starting with the problem questions. What you were talking about is impact questions. And I also agree with you. You can't come out and just ask someone impact questions. They don't know you and they don't trust you. But you can ask problem questions. And the reason why is because even by asking the question, it elevates your authority, right? If I ask you right, you guys are hosting a podcast and let's say there was a software out there that allowed you to automatically trim the podcast and clean up the audio and it can do it quickly. So if I asked you right, hey, this is Kevin from Podcast Inc. Real quick question for you here. How are you able to edit your podcast like under 15 minutes? Like, is that something you're able to do right now? Is it taking you a lot of time? That question is one going to expose a problem like, wait a minute, I can edit a podcast in 15 minutes? Like, and that's what builds curiosity. So the problem question is what bridges the gap? Situational questions I believe should be happen later in a discovery call, later in the process because you're wasting the prospect's time. You get me on the phone and you're asking me things that you could have figured out on LinkedIn. That's a waste of my time. You need to establish that you're even worth talking to.

One thing is that you're not asking is your question was, how are you able to edit that episode under 15 minutes? You're not asking me how I'm able to edit my episode period, or how do I edit?

That's the difference, right? Do I want to find out how you're doing it? Yes, I do. But I'M going to find out after you already know your way isn't the right way. These are the problem questions, or some of the gap questions that I've created. Slightly different than Keenan's is, how are you blank so that blank doesn't happen? So how are you editing your podcast right now in a way that doesn't have you tied up in front of the computer for five hours? And then you use something, what's called the illusion of choice. You suggest options for them, which one makes it easier for the prospect to answer, but it also plants the seed. There's another way to do it. So if I asked you the question, how are you editing your podcast right now in a way that doesn't have you tied up for hours late at night? Like, do you outsource it? Do you have, like, a software that, like, just gets it done in a snap? I mean, I know a lot of people, like, it just takes them weeks, and that's how they work on it. Like, how are you doing it? If I can also leave that question a little bit and show you that I know the most common ways people handle it, again, I'm trying to elevate my status. So now, even if you say, well, yeah, I outsource it, of the options I gave you, that one little seed of, like, do you have a way just to click button. Done already. Is planting some curiosity, like, wait, there's a click button way to do this? Right? And then here's a little tactical tip for you guys, downtones instead of Uptones. This is massive when it comes to psychology. Women are a lot better at this than men, by the way, too. We, as salespeople, we ask a problem question and then we use our favorite filler words. What do a lot of reps use as filler words for answers? Someone says, oh, this is how I do it. What do we say back? Ah, yeah, cool. Good. Sweet.

Beautiful.

Beautiful. All we just did was confirm their status quo. That's good. Great. Awesome. Beautiful. So what you do is you intentionally downtone. And again, massive amounts of curiosity. If you responded back to me and said, well, yeah, I outsource it, I go, oh, okay. I had one rep. They called it what they call it the bacon and eggs. Called the. That sizzle, right? Oh, you outsource. Okay. And then what do you do? You move right along, right? Oh, yeah, we outsource it. Oh. Oh, wow. Okay, well. And you move on to the next question. What does that build in the prospect?

Well, you're building some doubt, some insecurity. Like, wait, am I doing something wrong here?

And I didn't tell you you were doing anything wrong. I didn't immediately hop in and say, oh, well, I bet you outsourcing is costing way more money than our software. Let me tell you what it is. I just hit you with a little bit of, oh, okay, and move on. Now your wheels are spinning a little bit. Like, well, wait a minute, what's wrong with that? That's what I want you thinking about.

That's fascinating. Like, I do this all the time. The common response is, cool, beautiful. I'm affirming it because I don't want to get into this confrontation with the buyer. But in reality, like, you do have concerns about it, and you're expressing it in a way that they're like, wait a minute, Katie, why did you say that? Like, what was that noise you just made?

And I want to be clear. Like, you're not a right. Like, you don't go, oh, my God. Hey, hey, Jim, you hear this guy? Yeah, over here. He said he's like, no. Like, you're not about it. It's the subjects. Because, like, the way the subconscious works with some of decision making, you saying, good, great, awesome is reaffirming what I'm doing. And the whole point of selling is to unsell them on what they're doing now to sell them something new. If the whole discovery process, you're telling them, good, great, awesome, okay. Even without realizing what you're doing, you're making me feel good, great, awesome, and okay with what I'm doing right now, get to downturn. Subtle. Like, interesting. Okay. Huh. All right, I guess.

Okay.

That's what you're trying to do.

You talked about the formula for these problem based questions, and can you just break down that formula for me so that the listeners can go and actually build this on their own?

Yes. So what you do is you look at your product first, say, what is something that your product does very well that you know your prospect probably can't do? Right. So what's something your product does very well that your prospects probably can't do? Then you form a question asking how they're able to do that thing. So my earlier example was like podcast editing. Like, let's use a real example. You guys sell something. Who's got a product for me?

Armand's a sales king.

Let's use Carmine Armand. Let's rock.

You made me do this in the last one, too. We sell a product that allows people to manage their equity electronically instead of on spreadsheets. Which saves them time, billable hours and errors.

So let's go one layer deeper there and just like, what's like something specific? It does, right? So that's like the elevator pitch. Like what's something that your product actually allows me to do with my equity?

So for example, if you wanted to issue a stock option to an employee, normally you'd have to go to your attorneys and call them up and pay 300 bucks and have them draft up this agreement and then mail it in the mail and get it signed. You can essentially click a button, issue an option, do it in 30 seconds there.

So that would set up a great gap or problem question. Hey Katie, you're a startup, so I assume you guys issue a lot of options. How are you issuing options right now to a new employee? Like, is that something you have to work through your legal team and HR to get done? Is it something that you can only do quarterly so you can do the bandwidth? Or like, do you have like just a push button solution? Just like click and go, like, how do you do that? And then to make it even more powerful, you add the. So that blank doesn't happen. So if we build this all the way out, we say, hey, Katie, so how are you issuing options to your employees right now so that they know when they're getting them, you know they've got them and it's very clear when they're vesting. Right? Like, how are you doing that? And then you go into your options.

That's huge. Because right now that's actually the standard discovery question that we'll start with. But it stops before the. So that. Can you walk me through what it looks like to issue an option today? But you're saying, hey, can you walk me through what it looks like to issue an option so that you're not doing this every single day in those billable hours?

So why this works and is so much more powerful if I don't know what your product does or I don't know there's a better solution. When I answer that question, I believe I'm right. And then again, the leads are important. This is what makes you see, because if you call me, I'm a VP of sales and you go walk me through your sales process right now? What? No, I'm not going to do that. How are you interviewing your people right now? It's actually too open ended. This is what's interesting about salespeople. Most salespeople don't know what it's like to be sold to. When's the Last time you were cold called, like really cold called. When's the last time you were put through a cadence? When's the last time you sat through an SDR's call? When's the last time you sat through a 35 minute discovery session before you even got to see the product that you were asking to be in? When's the last time you sat through a demo and went through a follow up and had to get approval from finance salespeople don't know what it's like to buy. If they did, they would stop asking some of these super open ended questions because it's actually hard on the buyer. Like, I don't want to answer these questions.

What you're doing here is the. So that X doesn't happen. It's giving the. You're almost leading the customer. You're saying, hey, this is an open ended question. I'm not just sitting here asking how many employees you have and you just give a number. Like, I want to get a conversation going. But if you don't have a great background on what I'm selling and what my company does, I kind of need to point you and be like, hey, we want to talk about this. And so you're helping them out for sure.

It's so much easier on the prospect to answer those questions. And again, it does establish you more as authority. Right. Ahmed's the way they're answering it. Like, if you answer it and you're suggesting things that they know of, it makes you look smarter. Like, okay, he gets it. He knows what this world is like a little bit like, all right, we're good there. I like to reverse it. I did this in the two other ones on a demo. I asked the problem questions first, then some of the qualification questions. This is something Keenan I are very. If they don't have a problem, the other doesn't matter. It just doesn't. Right. And you're less likely to get the problem questions answered if you start with budget authority, need timing, decision making process. Like, okay, now tell me about your problems. Yeah, okay, not going to happen.

How do you turn the corner once you've asked 1, 2, 3, 4 problem questions? Because eventually it's going to be like, well, dude, you're just making me sit here and wallow. How do you transition to the next piece of the call? Is it a pitch? Is it trying to identify why that's happening? What does that look like?

So it depends on what call you're on. So on a cold call, you only need two problem based questions. Like you really do. Because all you're trying to build is enough curiosity on why they should show up to a discovery or show up to a demo. Right. But the formula is very similar. And this is what I teach to my reps. It starts with, I think this might make sense. I think this might make sense. And then here's your fill in the blanks. You're struggling with X and with Y, which is leading to Z. My company solves it by abc. We set up a time to show you how it might solve it for you. Do you have X time, blank or blank? Right. Because now, right, like, what's the point of the meeting? Did you catch it? What's the point of the meeting? Solve the problem to see if we can solve the problems that we now clearly know that you have. It's not to learn more, it's not to learn about the product. It's not like, it's not like, hey, in two questions, I already know you're not in an ideal state. Two questions, I already know you're not in an ideal state. This might be worth looking into. Now, if I'm on the demo, same idea, like, okay, problem, problem. You get to dig in a little bit more because you have a little bit more time. But again, you don't do all your discovery up front. Save some of the discovery for the demo to keep it engaging. If you ask all your questions up front, not only does the prospect feel interrogated, but then all that. And this is what sales reps do all the time. What's the check in question they asked throughout the whole demo?

Does that make sense?

Does that make sense? Any questions like, right, like, no, you do. That's like, so how does that compare to the way you're doing it now? So earlier you told me this is how you're doing it. How would you use this feature for yourself? Right, so. But the transition is the same. Discovery questions build up the problem, get a little bit more into, like, why. That's where you get some of the impact. I like to save the impact for when I'm showing them the opposite. That's when I like to get the impact right. It's like, hey, like, what's that causing up here? But then impact when I'm showing them, but I do them might make sense even in the demo.

So what's that line you said? I think that might make sense when you're suggesting setting a meeting, you're using it in the demo. Can you just give me the quick psychology on that so I can use it more effectively.

Yes. So first you're starting with a pull statement, not a push statement, right? When you just say, tell people something's going to be better for them, it pushes them away. They still don't know you. Right? Oh, this is going to be great. You're going to love this. This is the best product you've ever seen in your life. Okay. It's pushing them away. So when you start with, I think this might make sense real quick, if I stop there, where does your brain go? What are you wondering?

Well, what are you thinking? Tell me a little bit more.

Okay, so I'm building curiosity, right? Like, the way we teach is almost like a lean back, right? Like, you know, I think this might make sense. Okay, so we're starting with a poll first, right? Where it's like, all right, like, I'm listening a little bit. Then we put the problem in front of them. This takes away the not interested objection in a big way. Like, you'll always get not interested, but it's really hard to not be interested in your own problems. So I think this might make sense. Like, you're dealing with X, which is causing Y, right? So you can put that right in there. So we use the podcast example. It was like, so I mean, you're having to outsource your editing just costing you a whole lot of money, and you probably got to send it back a few times. Plus, you got to do a whole different system to do this Podcast Inc. We solve that, we automate it, we streamline it, we clean it up for you in, like, 10 of the time. I think this might be worth you just taking a look at. See, it might be worth it. Like, do you have 30 minutes today or tomorrow to hop on another call? How does Tuesday or Thursday look? So now I'm giving you choices, but again, it's on your problems, right? And notice how long was the pitch on Podcast Inc. 15 seconds. Not a lot.

You're focused on the problem more.

Podcasting solves your problems. Can I show you how?

That's the flow for a cold call. You're doing a poll statement, and then you're saying, we can solve your problems. How is that different for a discovery? What does that transition look like?

I ask all my reps this. I drive them nuts, and so they'll avoid me on it anytime a rep comes and asks me for help on a deal. If we were on a live session, it'd be hilarious if people could call in. I was like, hey, for 500 bucks, what's the question? I ask all my reps every single time of the deal. They'd all ring and call you. What's the problem? They agreed they had. So now when we get into discovery, it's like you have to get them to agree they have a problem, and you do that with a bucket question. So let's use the podcast example again, right? I don't know why we're using podcasts. None of us sell podcasts. But whatever. Say, hey, so I'm talking to podcasters all day long. They generally fall into two different buckets. Either they're not able to produce enough content, or their content isn't getting enough downloads. Which one do you fall into within the first five seconds? What have you already agreed there's a problem?

You gave two problem options, and I'm falling in one of them.

Right. And if I know my industry for you guys, which is it? As podcasters, which ones do you have a harder time with getting enough content produced or getting enough downloads?

It's going to be the latter. We got a ton of content here. Everyone wants to be on the show. I mean, look at you. You're here.

But for the rest of the demo, what will I always bring back? You're not getting the downloads you want. Every feature I show you is going to be back to how to get you more downloads. You already told me content wasn't a problem. And this is where salespeople go wrong, is they still try to sell their whole product. I'm only going to sell the pieces of the product that I can tie back to your downloads problem.

All right, Katie, We've gone through all the depths of discovery and the things that we do well and how we should be changing our mindset, but we haven't talked a lot about a ton of the bad habits, and there are a lot of bad habits that we gotta break. And so if there was one thing that every sales rep out there needed to stop doing today to be more successful, what would that be?

Once I stop treating your job like a hobby? To me, most sales reps treat their jobs like a hobby. They don't treat it like a career. They don't treat it like this could actually change your life. They don't even treat it like they treated their high school sport. Most people put more time into their high school sports than they do to their career, which could pay them multiple. Multiple six figures. It's just something that you wake up and go do when you feel. Feel like it. Like, invest in yourself, spend money on yourself, buy the courses, buy the Books like block time to do these things just drives me nuts that, like reps don't take this serious because they can change your life. I have 10x my income in 10 years just by getting this sales and psychology down. I mean, going from making nothing on food stamps with a daughter and a wife in like a room with a roommate, right, like, to where I'm at now, all because of these stacks of books you see behind me and the mentors that I've reached out to and the courses that I bought. I used to sneak into conferences so I could watch. I would dress like the wait staff just so I could go in because I couldn't afford it. But oh my God, like, before I go too far on a rant, that's it. Stop treating your career like a hobby. Stop treating it just like something you do. Invest in it and it will change your life. Literally change your life.

That's on point, Katie. And we've got a lot of SDRs and BDRs out there, and Nick and I hit on this all the time, is if you look at the most successful people out there, they're 60 years old and they're still reading three books a month. And so go guzzle some books, go read something, go talk to people and get out there. Everybody hang on for a 60 second recap email coming in soon. Cheers. Today's show is brought to you by Texas, which helps you move your deals forward faster. When timing matters, the fastest way to move a deal forward is to AVO getting stuck in the inbox. And so my favorite way to get on a text basis is literally when your prospect requests a demo, just send them a confirmation text saying that you're looking forward to the meeting and that opens the text channel for you to call back on it later, folks. We put an entire guide on how to revive ghosted deals, Nudge next steps and use texting to keep deals moving forward. With text us, check it out. It's free in the show notes.

Today's show is brought to you by Nooks. Nooks is the AI powered pipeline engine that researches your accounts, builds your target list, writes your emails, and gets you more live conversations on the phone. Thousands of reps at companies like HubSpot, Seismic and Deal use Nooks to automate the busy work and prospecting so they can focus on closing deals. Reps that use Nooks daily have twice as much pipeline as their peers. And we put together a guide with our friends at Nooks on how to automate the busy work in prospecting and dialing so you can focus on winning. Go get it for free at the link in the show notes.

Our top four takeaways for the episode with Katie include, number one, use problem questions with so that blank and with multiple choice options. So for example, instead of asking someone, how are you doing X process today? The first thing you should insert is how are you doing X process today so that X consequence doesn't happen? And then the last piece is multiple choice. And so what you add on at the end of that is you make it a little bit easier to answer and you say, hey, is it through lawyers? Is it through a spreadsheet? Is it through some other provider? And it gets people more eager to answer and it also gets them to think about possible problems. Number two, use a slight downtone when you hear the response to that question. And so if I say I'm doing it on a spreadsheet, you might say, oh, and it gets them to lean in a little bit more. It gets them to be curious. Number three, use bucket questions to narrow down your prospect's problems so you can categorize them into one of two areas. And then number four, use I think this might make sense before throwing your value prop in their face. It's all about pulling one or two punches before you give your value prop. Nick, how can people help us out?

Best way give us a subscription. Nothing else. Thanks for listening. We'll see you next week on 30 minutes of President's Club.

Sam.