In the age of AI, how do you future-proof your sales career? In this episode, Mark Cox and The Delusional Founder author Dave Hanley tackle the pressing questions currently hitting our digital mailbag.
We break down how to stop viewing AI as a replacement and start using it as your ultimate sales assistant. We also dive into actionable strategies for two of the toughest hurdles in sales:
● Ending the Discounting Habit: Why your team reaches for price cuts—and how to build true negotiation leverage through better discovery.
● Hiring World-Class Talent: Why attributes like humility and drive often outperform experience, and how to conduct reference checks that actually reveal the truth.
Whether you're a leader looking to coach your team or an individual contributor wanting to elevate your game, these insights will help you focus on the human connection that AI can't replace.
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Watch the episode here
Listen to the podcast here
ITF Office Hours Podcast - Episode 2
We’re back again with another episode. As always, we’re joined by my pal Dave Hanley, who’s the author of The Delusional Founder. If you’re out there running a startup, or you’ve got a smaller sales team, anybody, anywhere near the SaaS industry, you need the book, The Delusional Founder. It’s a fantastic read. It’s in the mode of The Wealthy, or The One Minute Manager , where it’s a shorter read, packed with great information, and super interesting. Dave would never do this for himself, but I’m doing a little commercial here for The Delusional Founder. Dave, good to see you again.
You, too. I appreciate the shameless plug there, right here at the top.
It’s got to be done. That’s how you sell these books on Amazon. Good news on the mailbag. The digital mailbag keeps filling up.
That’s piling up, Mark. We got a lot of good questions. We got some good responses from our first episode. People sent us in a few more, so we can keep the ball rolling here and answer a few more questions.
Let’s jump in. I’m looking forward to it.
Let’s look at question number one here. We’ve got Jim. Jim says, “I’ve been in sales for twenty years in the enterprise software industry. I’m getting a little bit concerned about the future with all of the hype around AI. My company seems to be embracing it. They’re even experimenting with AI-based SDRs to help with lead generation. How concerned should I be about my future as a seller? What can I do to stay ahead of the curve?” It’s a good one from Jim there. Hot topic off the top here, Mark.
The ITF Office Hours just became an eight-hour show based on the response here. First of all, Jim and Dave, thanks for the question. This is on everybody’s mind. Jim, this is on my mind too. As with anything, I still am a believer in the atomic habits approach to things, which is lifelong learning and always trying to get 5% or 10% better. I don’t worry about trying to get 30% or 40% better in any short period of time on anything because it’s not going to happen. You’ll just feel bad.
On the AI front, the future we’ll talk about in a second, but the first message to anybody out there is get in the game a little bit. Whether it's ChatGPT or Claude, start to think about, “How do I get in there? How do I start to have conversations with AI versus just asking for research?” A great pal of mine, Mike Sparling, who’s an AI thought leader, suggested in my commutes in and out of Toronto, “Try to have a conversation with AI instead of just asking for one question or some piece of research. You can make use of the dead time commuting.”
Using AI As A Strategic Assistant
I thought that was a great idea. First of all, let’s take brass tacks here. Everything will change, but it’s a great opportunity. It’s not a tool. It’s a great opportunity, but it only works if you understand your sales playbook. The truth of it is, you do have to go back to the fundamentals. He brought up SDR work. Let’s think about that. We look at our sales playbook. First, we have to understand our value proposition and our value proposition messaging. We have to understand our target market, which means starting with your ideal client profile and then understanding your buyer persona.
If you do not understand those two things, AI can’t help you. It’s going to spray and pray the way many companies do. Dave, this is a huge problem still with many of the companies. We hear from thought leaders like you all the time. Many of the companies out there don’t spend the time to truly define their ideal client profile. They go after everybody. They waste too much time on smaller deals that have no impact on their business. It creates a lot of noise.
Defining The Ideal Client Profile
Let’s say we did go through The Delusional Founder and learned to love selling. We understood our ideal client profile. What I can do is I can use the AI that’s embedded into a lot of the sales enablement tools out there to help me with firmographic data. There’s the size of the company, revenue, employees, technographic data, and what their tech stack is. I can help with trigger event monitoring. For sales training, a trigger event is when they have a new chief revenue officer. We want to reach out to them. They got funding. We want to reach out to them. On LinkedIn, they’re hiring nine or ten salespeople. We want to reach out to them.
We don’t want to reach out to everybody. It’s only helpful for my team if we have gone through that effort of understanding who that ideal client profile is. Will it take over a little bit of the work of SDRs? It’s going to take work off the table of SDRs for sure because those three things that we do research on that I talked about, which are firmographic, technographic, and trigger event monitoring, take 30 to 40 minutes per prospect. If I can get that in two minutes, or I can walk in every day, and that’s already done for me, that’s interesting.
If I have AI leveraging all of the data, the attributes I’ve talked about, when I walk in, it’s already been through my database. It’s gone through this. It said, “Mark, if you only have time to reach out to ten people today, these are the ten people you should reach out to.” I got one other thought, Dave, but does some of that resonate? Do you think that’s helpful?
Talking directly to Jim’s concern, he’s in the enterprise software space. That’s a very much relationship-based business. I was in enterprise software for fifteen years. I don’t think Jim should be too concerned about an AI agent taking over his complete sales process, and he’s out of a job. Going forward, the salespeople who are going to win in this more AI-based environment are the ones who use AI as a tool to do their job better and as an enabler.
Also, it’s those salespeople who are going to be the most human, the ones who connect with their buyer, help them solve problems, and talk to them. “What are you concerned about here? How can we help get over that?” It’s connected, because people buy from people. A key thing going forward for Jim is to lean into that because that’s not going to get replaced by AI anytime soon.
We always say on the show, “B2B sales is management consulting.” Management consulting is where you’re having that authentic conversation with a client or prospect. You’ve got a point of view as to how you can help them because you have experience and expertise. It’s not about pitching. It’s about helping. That’s absolutely right.
If there are folks out there who are SDRs, who’ve been trained to do nothing but pitch or be talking brochures, AI speeds up the removal of those folks from the ecosystem. You’ve got to elevate your game to get to that point where you can add value, insight, and knowledge in a live conversation dynamically with empathy. I love the idea that this will help the best get better, and it might bridge a gap between the best and the rest.
Jim should start to think about using AI as a sales assistant, frankly. For example, even in my roles, instead of sitting there after a sales conversation and putting a PowerPoint slide together to present at the next meeting, I pull up Claude. I go there. I have all of the brand assets. They’re already loaded. It knows how to formulate this. It’s like, “Here’s what I’m thinking.”
Hammer that in, and you get something back that you’re not just going to turn around and send. You can certainly use it as a good baseline and then modify it. Think about asking it like you’ve got a junior sales assistant. “Put this slide together. We need this for the next presentation.” Use it like that. That’s going to be super valuable and save you a ton of time that you can spend prospecting or talking to existing customers, and spend your time better.
Your answers on both of those were probably better than mine. I’m learning, too. I love it. Thank you.
Mark, we got another one here from Cheryl. Cheryl says, “I lead a sales team of sales reps who are quite autonomous, but I feel like too often, they’re jumping to giving a discount to a prospect to try to get a deal over the finish line. What can I put in place as a sales manager for them to let them do a better job with negotiations?”
Discovery As Negotiation Leverage
What a great question. Thank you, Cheryl. Dave, you default to discounting if you don’t understand the true value of your offering to that particular client. When we think of our sales process, we always talk about the most important parts of discovery. We’re trying to figure out what’s going on with them and their business, and the desired outcome they’re trying to achieve. The reason we’re trying to do that is we’re hoping to add some value, insight, and knowledge.
We’re also trying to figure out, can we help them achieve that outcome? Can we collaborate and work with them, not pitching a product, but figuring out the impact of that product on that prospect’s business? As part of discovery, we want to collaborate. If we can drive a desired outcome that’s meaningful for you, great. As we go through this process, it highlights that this won’t help you. I’ll tell you that, too. The idea is, let’s just figure out what’s right for the client.
If we spend enough time in discovery, then price doesn’t matter because chances are you’re working. You’ve defined a return on investment that is significant, with a 5X or 10X return to that client. Because you worked on it collaboratively with them and built it bottom up in their financial language, they’ll believe you. What happens, particularly in the SaaS world, is that you’re going to get a sell sheet that says, “This gives a 378% return on investment.” The buyer doesn’t believe you.
If you work with them and build that business case, then you know what the impact is going to be. If we do that properly, when they come back and ask for a discount, then I feel like I have a little more negotiation leverage because I know the impact of the solution on their business. If I don’t, I have all the negotiation influence. They’ve got all the weight and leverage. That would be my advice to Cheryl when she’s managing the team.
When she’s doing an opportunity review in the next sales meeting or the next one-on-one, first ask, why is this the right thing for the client to do? How do they build a business case to cost-justify the investment? If the salesperson has done that, that in itself is going to become negotiation leverage for them. If they haven’t done that, they’ve got more work to do. What do you think, Dave?
As you said, Mark, this is something where a lot of times, less experienced salespeople, a little bit more of SaaS churn and burn, get the deals in the door type of thing, fall victim to this. I learned this years ago. It was from two sources. 1) You, because you’d always ask these questions in our sales meetings. 2) I did a two-day negotiation course. It was Karrass.
I did the same one, except I did mine in 1929.
Yours was done by Karrass. It was super interesting. First of all, we went to this course. I’m like, “How do you do negotiation training for two days?” It was insane. What you learn is that a lot of people don’t ask the right questions to determine what’s important to the other side of the table in the negotiation, in this case, the prospect. They always assume its price when half the time, if you ask the right questions, you’re going to say, “What’s important? Let’s prioritize this stuff. Is it the price? Is it the features? Is it the time frame?”
People often assume it’s about price, but the right questions reveal what truly matters—price, features, timing, or something else entirely.
When you ask the right questions and prioritize that in terms of what their top-to-bottom priorities are, you’re like, “Price isn’t that important. They want this thing implemented before June 1st. We can rejig a couple of things and charge full price. It doesn’t mean anything to us to bump them up our priority list, but it’s huge for them.” A lot of salespeople don’t ask those questions.
From Cheryl’s perspective in a sales meeting, it’s like, “What are their priorities in terms of all of these categories?” Get the salesperson to think about that. Half the time, as you said, they haven’t even asked the question, so they don’t know. Once Cheryl starts to probe into that, they’re going to say, “I’m on the sales call. I’d better ask them what the priorities are across the board here for all these areas.”
It’s so funny about Karrass. Only another thought. We also have to think about it out of empathy for the sales team. If they’re doing a larger SaaS deal, they’re probably getting negotiation questions from business leaders. That’s where the things you and I came up with apply. Eventually, they’re going to get negotiation questions from purchasing agents or buyers.
That’s always a fun one.
You have to understand who and prepare appropriately for whom we’re speaking. Also, try to understand the dynamic between the two organizations. Sometimes, the economic buyer, the business buyer, and the purchasing group are not that well-connected. One of the things I did pick up from Karrass is that buyers get more negotiation training than sellers do typically. They are trained very tactically to ask for a discount two or three times.
Those procurement people have been through these courses more than any salespeople. That’s their job.
Part of that job is to ask three times. You have to get a few no’s. They’re taught to ask two or three times. At some point in time, you just have to be comfortable and say no. That doesn’t mean that kills a deal because there are always these escalations that might take place, but just thinking through that. Somebody comes back and says, “That’s unacceptable. How can you take that position?” That’s what a purchasing agent might say. They might come back because again, they have good questions on their side.
You need a response for that, whether you point to the market, whether you point to if they’re trying to negotiate things like cost, escalators, industry trends, market trends, or even pointing to educating the purchasing agent as to how their business operates. For example, in SaaS, we have an annual price increase of 7% or 6%, and you’re selling to a large bank. They come back and go, “That’s unacceptable.” You might just say, “What did your fees increase by last year?”
It’s an interesting thing, but we have to understand them in the business. One of the overarching themes is always to prepare for these things. When you’re going through that kind of negotiation, your teammates have been through this before. You’ve been through this before. Your sales leaders have been through this before.
Coming up with the 5, 7, or 9 questions you know they’re going to ask, be ready for the answers, so you don’t look like you’re caught in the headlights when it comes up, and you’re trying to dance or respond on the fly because we don’t tend to do well that way. We should and could do an entire show just on negotiation. Team, keep your questions coming in. It’s probably high time for us to find the global thought leader on negotiations to figure out, “How do we all keep current with this and keep our training current?” I still have those Karrass materials.
I might have them somewhere, too. From Cheryl’s perspective, if she hadn’t taken some negotiation training, as I said, it was a two-day program. That’s something to look into, more in-depth on that, because it’s pretty eye-opening. They set it up to be at the end. I remember it’s like, “This is very eye-opening, just the way their program is.” You’ve got to ask the questions. You have to know what’s on the other person’s card because you don’t do all these role plays. That was the whole thing they were trying to teach you there. It was cool.
Strategies To Expand The Pie
Back in the days of the billion-dollar deal, when I did that deal, first of all, helpfully, two years prior, I’d been to Harvard for their two days of negotiation training. One of the big things was trying to expand the size of the pie. Rather than thinking of the pie and I’ve got my piece, and I’ve got their piece, it’s our way of making this pie a little bit bigger for all of us. The split between the two of us doesn’t matter as much. It’s always understanding through negotiation the difference between a position and the interest.
If you can build that trust where somebody says, “I want a discount, I want this, or I need unlimited liability.” Say, “I understand the position. Why?” The more they start explaining why they’re asking what their real interest is, the better off you’re going to be. I’ll use one super quick example without boring folks here. Back in the day, when I did those huge deals, we were always negotiating check processing, meaning processing checks. Dave and I bet. Back in the day, he’d write me a check, and then I’d cash that check.
What they would always negotiate is liability if you make a mistake. I’d say, “Keep telling me more.” The more they explained it, they’d say, “If Dave writes you a check for $10 million and Mark, you cash it, and then you guys make a mistake on that one, we’re out $10 million, so you have to pay us back.” The more I explained it, the more comfortable I felt in my counter position, which was, “You’re paying me $0.03 to cash that check.”
You want me to take unlimited liability.
I’m going to take unlimited liability and kill my company. By the way, that type of mistake is an inherent risk in the business you’ve chosen to be in. We’re not taking over your risk. We’re processing the check better than you did. At least, I feel like I have a response. I still have scars from that one because I probably spent two months trying to negotiate that particular point.
Mark, talking about one thing that came to mind in terms of making the pie bigger, a lot of times, salespeople can get a little bit more creative in terms of how they deal with this stuff. This is something we talked about many years ago. If the prospect is pushing you for a discount, expand the size of the pie.
It’s like, “If we’re going to give you this 10% discount, we’re going to ask you to do a case study with us so that we can share that in our marketing. For us, that’s worth probably more than the 10% discount.” All of a sudden, they’re like, “Sure, why not? That doesn’t cost us anything.” Think about that. Get more creative. What else can you put on the table? There’s the whole concept of if you have to give something up, make sure you get something in return.
Two-year deal, give me a five-year deal. You don’t have to answer. You can always have a collaborative conversation. Cheryl, this is the one I always loved. Dave probably did this to me back in the day when we were helping his companies. He was like, “Mark, can you give me a discount of 15%?” First question, I go, “I totally get it. I’m not sure. Dave, how did you come up with 15%? Why didn’t you come up with 12%, or why didn’t you come up with 17%?”
I was getting into this level of detail. Dave had a partner whose name will remain protected. His name’s Dave Da Costa. He used to nickel and dime everything. He couldn’t squeeze enough juice out of our lemon. Eventually, you just have to say no. Sorry, DC. We love you, buddy. Shall we try to squeeze one more in here?
I don’t know if this one’s going to take too much time. The negotiation topic is so huge. We could do a two-day show on that. This one’s a little more to the point, hopefully a little more tactical. This one’s from Ryan. Ryan says, “We’re building out our sales team. I’ve been doing quite a few interviews lately. When it comes to reference checks, I feel like they aren’t very useful because references aren’t that keen to open up and give me the straight goods. What do you recommend to help make reference checks effective?”
Conducting Effective Reference Checks
What a great question. Thank you, Ryan. First of all, a couple of thoughts. One reference source I would point to, which I still love to this day, is a book called Who by Geoff Smart and Randy Street. This is a tip I picked up from reading that book, whether it was ten years ago or fifteen years ago. When you’re doing a top-grading interview, some of the questions you like the candidate to speak to when they’re speaking about their different roles.
There are four questions when they’re telling you the story of their career. What were you hired to do? What stands out as accomplishments you’re most proud of in that particular role? What were some of the more difficult parts of that job? Why did you move on? If we go to the third one, what were some of the more difficult parts of this job? That’s where on their CV. I take notes when we’re talking about this. I’m interviewing Dave Hanley.
He’s telling me that ten years ago, he didn’t love the management style of a particular company at a particular time. I keep track of those because three weeks later, I might be calling Dave’s reference. When you’re speaking to a reference, they wouldn’t be a reference unless they’re going to say great things. Sometimes, putting some distance between the conversation and the candidate is helpful to the person you’re speaking to.
I might say, “Peter, Dave mentioned ten years ago, when he was working with you, he had some difficulty with the sales reporting and the management cadence. Can you tell me a little bit about that?” Two things happened with Peter. First of all, he doesn’t feel like he’s throwing you under the bus because this is ten years ago. Secondly, the fact that I said, “Dave told me about this,” Peter opens up a little bit.
I might ask a question, saying, “What were you coaching Dave on back in those days? I know that was a long time ago.” Again, he’s never going to say something bad about Dave, but he might highlight one or two things that I’ll consider if I noticed it because clearly, we understand that Dave Hanley has a problem with authority. Anybody who knows Dave Hanley knows that’s the case.
It’s hypothetically speaking.
This won’t change my opinion, but this might give me some help for anything different I might push on a little bit. It might give me some insight into how to best work with Dave. I don’t think it’s going to change whether we move forward with a candidate, but it might be helpful insight in terms of how I best work with a candidate. That would be one thought. What do you think, Dave? You can use me as the example. Get me back.
By the time you make that reference call, usually, you’re pretty convinced that this person is right for the role. Part of the issue might be that it sounds like they’re doing a lot of hiring on Ryan’s team there. Part of the root problem with a lot of these hiring processes is that they’re using the reference as validation when they’re making the right decision here. It’s tough. It’s sometimes hard to find the right people for the role, but I’ve always thought that if it’s not a hell yes, it’s a hell no.
If I’m not super excited to hire this person, the reference check is not going to make much of a difference. I’m like, “I’m not quite sure. Let’s see what the reference says,” because they’re not giving us references that aren’t going to give great feedback. In terms of references, one thing that I’ve always found useful is when you talk to them, it’s like, “The person’s good. They’re good at this. Yes, great to work with.”
I like to ask straight up. This is helping you dig in and try to figure out, as you said, not necessarily am I going to hire them or not, but give me something useful that when I do hire them, I can figure out how to maybe manage them. On a scale of 1 to 10, where would you put this person? No one’s going to tell you a 1, 2, 3, or 4, but if it’s a 10, it’s like, “Great. I thought they sounded amazing.” If it’s a 7 or an 8, it’s like, “Thanks, but what do you think could get them to a ten?” At least, they’re like, “Good question. They could be a little better at prospecting, or they’re a little sloppy with contracts.” That leaves you like, “Good to know.” Tuck that one away for later.
I got one more question for you on this, but Team, just a couple of thoughts when you’re doing reference checks. Do them even though it feels self-evident because we’ve heard this with some folks, Dave, where they say, “They’re only going to get people who love them.” Double check. Secondly, the reference should be somebody they reported to not appear. You want to check.
Ask my neighbor what I’m like. You’re going to get one point of view. You can ask somebody I reported to in 2016. You’re going to get a different one. Make sure it’s somebody you reported to. Dave, out there, you’ve done so much of this. When you’re interviewing, what are the attributes you look for in a new candidate?
It depends on the role. For example, I’m helping somebody hire an SDR. Those people don’t have a lot of experience. Often, they’re pretty early in their career, coming out of school in many cases. For those types of roles, I’m not digging into, “Tell me about your work experience working at Target before you went to college.” It’s more like, “Tell me about a time when you did something competitive.
Tell me about a time when you got some tough feedback. What did you do with that, and how did you improve? Tell me about something where you’ve gotten significantly better over the last several years.” It’s that type of thing. With a more seasoned salesperson, it’s very much, “Let’s talk about the numbers. What were you hired to do, and what did you do?”
Dig into the performance. Dig into problem-solving and tough deals. How do they handle that? It’s a situational type of stuff to figure out how they think. You’re trying to find somebody who matches your values and what’s been successful in your sales team. Different companies have different key values and what they feel is important.
Dig into performance, problem-solving, and how people handle tough deals. The goal is to understand how they think and whether they align with your team's values and success.
Culture is for sure a big part of it. I love that. I have a little checklist of things I’m looking for, which are intelligence, drive, humility, passion, and optimism. I rank them as having an interview.
Hiring For Humility And Drive
You can’t beat somebody with all those. It sounds pretty good.
None of that is industry experience or depth selling. If somebody’s got all of those things, I could probably teach them to be an SDR. Humility is a big one, no matter what stage of career. Humility means not shy or retiring. It means somebody understands they don’t know it all.
Here’s another quick story for you. You’ll like this one, too. We didn’t just hire people named Dave, but Dave Da Costa and I were interviewing another fellow you know quite well, Dave Pittman. Again, it’s a fresh SDR role out of school. We interviewed a guy who came in earlier. We asked him straight up, “Have you ever worked on the CRM system?” It was clear this other guy had never had his hands on a CRM system, but he started BS-ing us a little bit.
Dave and I are looking at each other like, “This guy doesn’t know what he's talking about.” That’s a massive red flag. Fast forward, the next interview is with Dave Pittman. We all love Dave Pittman. He comes in right out of school with no experience. We asked the same CRM question. He says, “You know what, guys? I’m going to be honest. I don’t know what a CRM system is, but I’m willing to learn. I’m eager to come in, sink my teeth into this, and be a great asset for the team.”
We’re like, “You’re hired.” That’s because nothing kills your credibility on a sales call more than a prospect asking you some technical question, and you’re like, “BS, this, that, the other.” It’s like, “You know what? I don’t know the answer to that, but I’m going to talk to the team, find out, and get back to you.” They’re like, “Perfect. Credibility, done.”
Humility, check. On the culture side, there’s integrity. Tell me the truth. With mature salespeople on that front, I do look to say when somebody left a role, “We agreed it was time to part company.” No, you didn’t. Ask me about my career, and I’m going to point out two or three major mistakes I made.
One, I took a job for money. That was a big mistake. Just be honest and upright because what you want with somebody is, can I completely trust them? Do I get the whole story? That transparency and authenticity are what we’re all looking for with people that we interact with in life. Dave, what a great discussion again. This is super fun. Thank you.
For all the followers and audience out there that have Mark on LinkedIn or any of the other social networks, keep sending us some great questions because I’m learning as much as you are here. It’s a fun conversation. It reminds me of a lot of things that I need to keep thinking about.
Me, too. Dave, thank you. Team, thank you so much for tuning in to this show. As Dave mentioned, whether it’s through LinkedIn, Mark Cox, or email MarkCox@InTheFunnel.com please keep filling our digital mailbag. We’ll take on all the topics you want to talk about in the show. Thanks for tuning in. Have a great week.
Thanks, Mark.
Thanks, Dave.