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Index/Sales/Higgle: The B2B Sales Club
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The Hidden Advantage of Tactfully Handling Difficult People with Alex Sobol, Part 2

Higgle: The B2B Sales Club · 2026-06-22 · 34 min

0:00--:--

Key moments - from our scoring

Substance score

53 / 100

Five dimensions, 20 points each

Insight Density10 / 20
Originality8 / 20
Guest Caliber13 / 20
Specificity & Evidence12 / 20
Conversational Craft10 / 20

Alex Sobol, co-founder of Millennium Alliance - a premier C-suite community with 12+ years of experience connecting enterprise technology vendors to executives - diagnoses why most B2B technology salespeople underperform despite looking polished and professional. The core problem isn't product or pitch, but hiring and approach: companies recruit for pedigree and polish while missing tenacity, rejection resilience, and emotional maturity. Alex argues that entry-level tech salespeople often waste discovery time asking scripted P&L questions to executives who already committed to the call, when they should spend 30 minutes demonstrating genuine value. He critiques the prevalence of obvious questions ("Would that be valuable?") and ChatGPT-generated prompts that signal time-wasting. His hiring process - a rigorous 4-6 round funnel culminating in founder conversation - filters for likability, work ethic, and ability to handle difficult personalities without ego. Alex contends modern B2B selling requires speed (C-suite roles turn over every 2-3 years), specificity, and comfort with forcefulness - traits American culture often discourages in favor of appearing non-salesy.

Key takeaways

  • →Hire for tenacity, rejection resilience, and likability rather than just prestigious credentials - work ethic and personality fit matter more than resume pedigree.
  • →When a prospect takes a 30-minute call with you, you're past discovery; they've already self-qualified, so spend time demonstrating value instead of asking obvious questions.
  • →Stop asking generic ChatGPT-style discovery questions; ask only questions where you genuinely need the answer to advance the conversation toward next steps.
  • →C-suite executives rotate frequently (CIOs rarely stay 3+ years), so lengthy sales cycles and over-caution cost you deals when your contact leaves before closing.
  • →Rigorous multi-round interview processes for hiring aren't just stress tests - they signal fit to candidates and protect company culture from difficult personalities who drain resources.

In this episode

  1. 1Introduction to Alex Sobol and Millennium Alliance
  2. 2Hiring the Right Salespeople: Beyond Resume and Pedigree
  3. 3Building a Rigorous Interview Process to Assess Fit
  4. 4What's Changed in B2B Selling and C-Suite Engagement
  5. 5Common Mistakes: Economy Headwinds and Executive Turnover
  6. 6Discovery Done Wrong: Asking Questions That Waste Time
  7. 7Effective Sales Approach: Demonstrating Value Over Scripted Questions

Mentioned

HiggleMillennium AllianceLinkedInAlex SobolMike LandaIndiana UniversityDuke UniversityUniversity of ChicagoChatGPT

Guests

Alex Sobol

Topics in this episode

LinkedInDiscovery callsMillennium AllianceB2B sales hiringC-suite salesTechnology salesSales interview processesEnterprise technology procurementSales team managementTenacity in sales

Questions this episode answers

Why do technology salespeople struggle despite good interview performance and exceeding targets?

They often lack the soft skills that separate great from mediocre sellers: tenacity, ability to handle rejection without taking it personally, emotional maturity with difficult people, and willingness to be persistent despite discomfort. Many are hired for intelligence and school prestige but miss the character traits required for sustained success in the space.

What's the biggest mistake salespeople make in discovery calls with C-suite executives?

Spending too much time asking questions when they only have one opportunity with the prospect. Alex says executives who take the call have already done basic homework; instead of 30 minutes of discovery questions, salespeople should spend most of the time demonstrating why their solution genuinely benefits the prospect and addressing their stated interests.

How does Millennium Alliance's hiring process identify the right sales fit?

Through a 4-6 round interview funnel where interviewers assess likability, work ethic, ability to handle rejection, ego level, and how candidates respond in difficult situations. If any interviewer is on the fence, they pass, because a poor fit affects not just the hire but drains energy and resources from the entire team.

What questions should salespeople ask during product demos instead of obvious ones?

Ask questions where the answer genuinely informs the conversation - like "What specific value does this solve for you?" or "Why haven't you solved this problem before?" rather than obvious questions like "Would this be valuable to you?" that feel like time-filling and signal you don't understand the prospect's needs.

Why do C-suite roles turn over frequently and how does that affect selling strategy?

CIOs and executives rarely stay in roles longer than 2-3 years, so long sales cycles work against you. Salespeople must capitalize on interest immediately rather than taking time egregiously, because the decision-maker may leave before you close the deal.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

10 / 20

There are a handful of genuinely useful ideas - C-suite tenure shortening deal windows, the leverage-flip when a prospect is already bought in, and the danger of scripted discovery on a limited call - but they're surrounded by a lot of conversational padding, repetition, and generic encouragement. The rate of novel, actionable claims per minute is moderate at best.

the C suite community, it's rare that you see a CIO that's been there for five years. It's almost rare to see. It's not that common to see people there for three years
salespeople are so obsessed with getting the win that they don't realize that higher price deals, like, it's better for the long term relationship to stay strong and defend what you've pitched as value

Originality

8 / 20

The core arguments - hire for grit not pedigree, don't discount, be in the trenches as a CRO, SPIN selling is transparent - are well-worn sales orthodoxy. The negotiation anecdote with the live demo in front of 20 reps is a nice storytelling device, but there is no genuinely contrarian or first-principles framing anywhere in the episode.

the cat's out of the bag on spin selling. So if you think spin selling is what's going to get people to work with you, like people have been through this
The chief object of education is not to learn things, but to unlearn things

Guest Caliber

13 / 20

Alex Sobol is a genuine operator - co-founder of a real 12.5-year-old business with a 75-100 person sales org and 20 seven-figure annual clients - so he is speaking from earned experience rather than theory. However, the conversation stays at a fairly general level and doesn't extract the depth that his background could justify.

we have about 27 figure clients a year, right? we have 20 companies that spend over a million dollars a year with us
it's got to be 75 to 100 people now

Specificity & Evidence

12 / 20

The episode includes several concrete anchors - 20 million-dollar-plus clients, a $1.4 - 1.6M deal held at full price, a 10-year LinkedIn tenure, a named university negotiation class - but key claims about email cadence effectiveness and market trends are attributed to unnamed 'prominent businesses' and stay vague, limiting credibility.

It's $1.4 million deal, $1.6 million deal. I said, it's not going to happen. It's not going to happen if I'm professional. And I got on the call and just like I predicted on video
my wife went to Indiana University and she had a tough time getting a job there. And fast forward her getting the job there from her persistence. And she was the top seller every single year in her department for 10 years straight

Conversational Craft

10 / 20

The host occasionally pushes usefully - challenging discovery methodology, prompting the SPIN selling critique, and injecting his own procurement-side perspective on discounting - but the conversation is dominated by agreement and affirmation, and most of the host's follow-ups finish Alex's sentences or validate rather than probe.

So why don't you like spin as a methodology?
as a buyer, if you offer me it's 100 grand, and I say, Ah, no, I can't do 100 grand... If the salesperson says, can't do 60, but I could do 75, two things happen in my mind

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Alex Sobelguest74%
  • Mike Landahost26%

Most-used words

selling24salespeople23sales22alex22trying17questions16type16part15call15best12feel12back11technology10doesn9millennium9interesting9

Full transcript

34 min

Transcribed and scored by The B2B Podcast Index.

Alex Sobel: And I always say, I don't wanna tell you how to do your job. I said, just with me, you're not gonna get very far. If you think asking me questions about what are the things that keep me up at night, what are the big objectives I'm trying to hit financially, like all these stupid P and L questions that an entry level tech salesperson doesn't even know what they're talking about. I think it's people are doing this dance and like a lot of them are doing it, right? A lot of them are doing it.

Mike Landa: My name's Mike Landa and you're listening to Higgle, the B2B Sales Club podcast where we bring you actionable insights about sales, RFPs, negotia and difficult procurement discussions from sales leaders, brand leaders and procurement leaders. Please subscribe to get updates when new episodes are released. Alex, welcome Back to part two of Higgle the B2B Sales Club podcast with Alex Sobel. Alex, great to see you again.

Alex Sobel: What's going on? Mike, nice to see you again.

Mike Landa: Really good. So for people listening, obviously I'll ask Alex to introduce himself, but if you want to know what his favorite song is and why, you better listen to part one because he's not repeating it. Part two. So Alex, for the new listeners, who are you? What do you do?

Alex Sobel: So, yeah, and thanks for having me again, Mike. My name is Alex. So I'm one of the two co founders of a organization called the Millennium Alliance Global headquarters in midtown Manhattan, New York City, uh, European operation based out of London. Essentially we're a premier invitation only community for North America and Europe's leading C Suite executives. Essentially, we've become one of the more faster growing platforms for C Suite engagement globally. Now, 12 and a half years later, we've evolved into an international multimedia company that provides access to the enterprise technology community through a combination of digital properties and high impact in person events for businesses of all sizes looking to reach that audience. In a nutshell, that's pretty much who we are.

Mike Landa: Brilliant. And again, this bit wasn't definitely rehearsed, Alex, but I have to say you're a really, really just decent, interesting, nice person to talk to.

Alex Sobel: Oh, thank you.

Mike Landa: That makes it just so much easier.

Alex Sobel: I appreciate that. I think, I think the same to you, Mike. That's why we seem to have a good flow.

Mike Landa: Yeah, exactly. Because the questions and the kind of responses seem to just flow and we jump down some rabbit holes. So for the listeners, part one, Alex kindly talked about the kind of the millennium origin story where they came from what they learned, what were some of the success factors? One thing we touched on in part one, and definitely go back and listen if you have missed it, was about actually how do you recruit people, particularly salespeople, and about how do you spot the right kind of people. And in part two, we're going to talk about the kind of the approach, the secret sauce a bit more. Biggest things that people need to understand about selling. So part two, Alex, is about B2B.C suite sales. What's working and um, why. Just give us some context. What's happened to B2B selling in the last five years? And uh, is the old model dead? By the old model, I mean kind of like there was this big thing about cold outreach at scale. It wasn't personalized. AI came along. Now it's mass personalization at scale. Mass outbound automation. Has that world changed? Is it dead? What's changed in B2B selling?

Alex Sobel: I think the main thing comes down because, you know, I think about this a lot. I think companies are just hiring the wrong people. A lot of organizations, I'll give you an example, right? My wife worked at LinkedIn for a decade, right. And phenomenal culture, phenomenal people, and obviously phenomenal products. There's not a B2B organization in the world that can operate effectively without LinkedIn, in my opinion. I think that's pretty much a fact. And at least when she was applying to work there, they very much were very focused on how good the resume looked, how good the university was ranked. A lot of kids from Ivy League colleges in the states, Duke University, Chicago type people. And my wife went to a decent school, she went to a good school, she went to Indiana University and she had a tough time getting a job there. And fast forward her getting the job there from her persistence. And she was the top seller every single year in her department for 10 years straight. And I noticed that a lot of the people that they hired, they just weren't the right type of people to be selling a technology platform. I think I use that as an example because I think a lot of these companies, they're just hiring, they're falling into this trap of hiring the wrong types of people. Not that there's anything wrong with those people, they're just wrong for those type of roles you need in today's age different than it was 15 or so years ago. In selling in general, you got. I think the baseline is two things. You have to have a good work ethic, you have to be someone intelligent. So. So I understand the desire to want to hire from prestigious schools because you will get someone who's intelligent. But what I think they're missing is they might get the work ethic right piece, they might get the intelligent piece right, but they're missing the piece that separates mediocre or sub average salespeople from the great salespeople, which are all the things that we talked about in episode one that make salespeople certain salespeople special, which is tenacity, being able to handle rejection, never taking anything personal, being able to deal with difficult people, not approaching things in a way because you're, you know, someone that you're talking to has a certain type of title, not getting concerned because someone's getting annoyed with you a little bit. I think in the technology selling world especially. And again, we don't when we're starting to sell technology, but it's not core to who we are historically. The technology salespeople I see and I've seen thousands of them, they look the part, they dress the part, they present really well, but they're missing things that are causing for them not to be as successful at their companies as they can be, which is why you see a lot of them move around from time to time.

Mike Landa: Now then, let's dig into Alex again, completely unprepared. It's always the best. It's really hard. And, uh, none of this for the listeners makes these kinds of salespeople bad. So don't think this is a judgment thing. It's a fit thing. The problem with interviewing salespeople is, well, if they didn't present well, then they'd on the whole be bad salespeople in the first place. So you've got a problem, which is most salespeople will show up well and interview well and that have done their research because it's kind of part of selling. So the problem now is like, well, how do you distinguish, how do you find the people that will be a great fit for your company and a great fit with your clients and prospects? What is it that you do beyond the yes, they've hit target or they've exceeded quota and they understand the broad ICP that you're targeting and by all means repeat what was in part one, Say something different. How do you. How does anyone go, yeah, that's all kind of table stakes. I expect that. Now let's find out if you really are right for us in your experience. What is that thing that for Millennium, makes it the right fit?

Alex Sobel: Well, I think baseline putting someone through a rigorous interview process is a good thing because at the foundational level, they will test their endurance, and it will test to see how many people liked them. Part of anything in life is, in my opinion, but especially in selling. People buy from people they like. Right. They may not like you initially because you're very persistent and you're annoying, but they grow to like and respect you. So in regards to the interview process, if you get to me, which is usually round four or sometimes round three, even if it's for 15 or 20 minutes, the two or three people that you spoke to previously liked you enough that they thought it was worthy for the founder of the company to have a talk with you. Every now and then, I'll send some. A message. Surprised that person got to me. Um, because the types of people that we have at Millennium now understand, as they spent more time with us over the years, what we're looking for, and they're that type of person. They're kind of looking for people that have similar traits to themselves. So I think just going through a rigorous interview process by itself is a good stress test. And then, you know, when I talk to them, I'm curious to know why they made the decisions that they did. Curious if they say anything that is sort of unorthodox to say on an interview. I'll give you an example. You may think differently. This. I'm actually curious what you think. I interviewed someone, this happened a few times over the last couple of years. And I like to talk to people about their families and see what they say. One of the reasons I do the interviews is not just because I think it's good for the business. I actually genuinely and everybody knows this about me inside Millennium and friends of mine. I like to talk to people I've never met. I actually thoroughly enjoy it. My wife gets annoyed when we go on vacation because I like to talk to. I like to know where everyone's from, and I like to talk to them. And person said to me it was a young guy, and he made it to point where I talked to him on the interview, when I was talking to him about his family, he made a point to tell me how much his mother was his best.

Mike Landa: Okay.

Alex Sobel: And I think that's great that his mother's his best friend, but it was a big piece of the interview for him that he wakes up every morning and all he thinks about is his mother and he wants to give back to her. And they have such a unique bond now. I don't think there's anything wrong with that. I'm not judging that, but I Thought that was a weird thing to go very heavy into in an interview process. That just like hit me in the gut that there's something odd about that. Not odd, uh, that it was mentioned somewhat, but the depth that someone went into. So you know, I'm going down a rabbit hole here. But it's just, I guess I'm getting a feel for a couple of things I'm trying to get a feel. One, is the person likable? Does the person have a good work ethic? What other people thought of them? Do I think they're the type of people that someone would want to get a beer with and how they kind of check the boxes of do you think they'll be good in difficult situations? Do you think they'll be able to handle rejection? Do you think they'll go back to a prospect multiple times that's rejected them? Do you think they have any ego? Do you think they care what necessarily people think about them in the setting that we have? But I also am trying to assess that they've got a lot of baggage. There's no easy way to write the formula. But by the time you get to me and then we converse on someone, we're all kind of looking for the same things. And if we're all in agreement that we think they're a good fit, they usually work out. And if any of us are on the fence, we usually pass because we want to feel really good about ah, who we bring on.

Mike Landa: Exactly. That's not me and Alex judging anyone. That's just about making sure that they're the right fit. And that's, I think that's good for the candidate and good for the company because bluntly joining a company and then finding out within three months that actually you're a bad fit, that's bad for everyone. No one wins in that situation at all. It's really draining. And I think that's one of the reasons that you have a four or five or six part process. Some candidates complain it's too long winded, but it's done for a reason. And actually if it's a five part process on one person out the five says no. Well, you have to take that really seriously because that person just may not be right for this business.

Alex Sobel: You know what I think about it also it's not just right for them, but it's not right for the people at the company.

Mike Landa: Exactly.

Alex Sobel: Someone who's not a good fit and they're a tough personality, for example, it's got a knock on effect for everybody else. And the truth is, I'm not just saying this to say it's really not fair.

Mike Landa: Yeah.

Alex Sobel: When you put someone in a department or on a pod with someone and they're not easy to work with, they're difficult or they're not getting it and they're draining resources, it's a negative effect for everybody. It has nothing to do with money and paying someone. That's not going to work out. It really is the time, the energy and the knock on effect it has for the people around them.

Mike Landa: Definitely. So in terms of what works in B2B these days, just go back and kind of like just headline. What do you think works? You talk to C suite executives all the time from, you know, large, medium sized companies all the time. What do you think has changed in the way that they want to buy and be sold to as customers?

Alex Sobel: Well, I'll talk about things I see from salespeople from technology companies that I find interesting. I think they all think they're playing a different game than each other. Right. When I go to events of ours, I don't get to go to too many of them anymore. But when I go to events of ours and I talk to companies, they all make it a point. The sales team, not all, but majority to say, yeah, we take a different approach than everybody here. We're not really selling to these people, we're just getting to know them, educating them on the market. And they think there's some unicorn, but they're mostly all taking that approach.

Mike Landa: Yeah.

Alex Sobel: And I think what people in the selling world, I guess in the technology space, which is, you know, an exciting space, and there's so many companies and there's so many people trying to get into it and I'm speaking as an observer of it, like a front row seat to it. I think they just got to be more cognizant of what's working against them. Right. There are things they cannot control that are already putting them in a tough position. Right.

Mike Landa: Like for example, what they be.

Alex Sobel: So the ebbs and flows of the economy. Right. The fact that the people that are trying to target don't stay in their roles for that long a periods of time. You know, the C suite community, it's rare that you see a CIO that's been there for five years. It's almost rare to see. It's not that common to see people there for three years though. This dance that people play about being very delicate with their approach, especially after someone has shown some interest. You got to capitalize on that and on the surface, a lot of people products look the same. And the time that you get with people, you got to spend explaining why you wholeheartedly think it will benefit them. I think two mistakes people make, Mike. The first one is, again, not realizing what's working against you. That's out of your control. And one big thing is that people move around a lot. And by the time you get somewhere very far, get in a far stage with someone, they could be gone. And you're kind of in a very tough position. So taking your time or taking your time egregiously is not a good thing to do. And the other thing is, is that I think what a lot of people get in these type of conversations with the C Suite or with anybody, they're asking them, like an abundance, uh, of unnecessary questions.

Mike Landa: Right, exactly.

Alex Sobel: And that feels a lot of the time like maybe I'm very fortunate because what we do, I know, is beneficial for the masses. And if you're selling a technology product and it's an IT security product and you think it's beneficial for most companies in every industry, you should go in not avoiding questions, but spending more time than you are explaining why and using certain selling skills for people to understand why they should be really considering you. When I get on a call with a, you know, we have a really cool sales tech stack inside Millennium. I'll take a demo. I like to take them. And the salesperson gets on the call and they want to spend the first 30 minutes with me. I only have 30 minutes, and they want to spend 30 minutes with me asking me questions. Because that's how they were trained.

Mike Landa: Because they were trained that you have to do discovery. And they're right. You have to do discovery. But they're following a script. Yeah, they've kind of missed the point, really.

Alex Sobel: I don't care about the script so much. But I say to people sometimes, guys, listen, you're not going to get me for another 30 minute call.

Mike Landa: Correct. You have one shot. The fact that you took the call, Alex, that surely most salespeople would go. The fact that the founder, uh, took a call for 30 minutes means we're way past. Hi, who are you? Let me explain where I'm from. You know, Alex, you look like a nice guy, but I'm an ex procurement director. I can kind of tune into this. I'm like, the fact you've got my time means I've already done my homework. Uh, so let's get to the chase really quickly to see if there's anything here or not.

Alex Sobel: Yeah. I always tell people respectfully, like, I'm interested in what you guys have to

Mike Landa: say or else I wouldn't be here 100%.

Alex Sobel: And I always say, I don't want to tell you how to do your job. I said, just with me, you're not going to get very far. If you think asking me questions about what are the things that keep me up at night, what are the big objectives I'm trying to hit financially, like all these stupid P and L questions that an entry level tech salesperson doesn't even know what they're talking about. I think it's people are doing this dance and like a lot of them are doing it, right? A lot of them are doing it

Mike Landa: because they like experience and uh, they like emotional intelligence.

Alex Sobel: Yeah, it's just like, you know what? I also, I think it is, Mike, different than the uk. I'll give you guys credit, right. I think you guys care less about what people think than they do in the States. I grew up in an environment, I'll give you an example when I was graduating College, all in 2007. So a year before the big global financial crisis. This sums it up really well. I remember two out of the eight of us got jobs in sales and the other six predominantly got jobs in like big banks, you know, because that looked good, that felt good. And I remember just people in America. I don't know if it's like this as much now because technology sales is kind of elevated selling in terms of prestige. But just like this notion that you're going to have to ring people up and cold call and prospect, there's like a, a lot of people think that's beneath them type feeling. And I think what happens is that when people get into a sales role because they essentially didn't necessarily want to do it, but they didn't have any other options and they got a shot to be a seller when they get to the job and they get any type of friction from a prospect or they get told that yo, like, you know, leave me alone, or they're getting to feel uncomfortable. They let the uncomfortableness dictate how they continue to do their job. So I think it's a combination of a lot of things, but I think that people are afraid to like, be the type of forcefulness they need to be to get to where they need to go. And you know what's interesting is that a lot of these people, they're doing the same things over and over again. They're getting the same results and they're not changing Their behavior. How I learned this was on the job training. I saw that the approach that I was taking initially, because it made me feel better as a person, not as salesy, wasn't working.

Mike Landa: Yeah, but you kept repeating it and you're like, uh, hang on a minute.

Alex Sobel: I don't live in that world. I live in the world that I don't care how it makes me feel. If I'm trying to hit an objective, I'm going to hit it. And I think there just needs to be more of that kind of thinking.

Mike Landa: Exactly. And again, take that real example. They get you on a call for half an hour. There's been some kind of precursor. Either you, one of your team, someone has had an email exchange somewhere with the vendor and you've gone through some basic stuff in order to say, yes, this is worth a call. And so again, just interested in your view. I was taught discovery. I've done lots of discovery calls. I've helped people with discovery, blah, blah. But the key thing I'll be going is like, Alex, what's on your mind? We've got half an hour. What's the key thing that we need to talk about on this call for the next kind of 30 minutes that's going to make you want to go, yep, let's do something. Next steps or no, let's kind of like, it's not going to work for us. I'd speak into the moment there's something on your mind, but I'm not a mind reader. Well, I'd ask you 100%.

Alex Sobel: 100%. And the thing I want to be clear about for your audience is definitely ask questions.

Mike Landa: Yeah.

Alex Sobel: But don't ask questions where the answers are relevant to what we're talking about. Yeah, like asking questions. Like, I'll be on a demo with someone and they'll be like, they'll say, hey, I'm just curious, like, what did you see that you liked about this that you thought was good? And that's a great question to me because I'm like, well, listen, like, I'm not really tech savvy and this is what how I thought initially it could be good. Like, can you show me? Like, am I on the right track?

Mike Landa: Does it do that? Am I right? Am m I wrong? Does it do that thing that I think, yeah, exactly.

Alex Sobel: When someone starts asking me questions that they got from chat gbt, I'm just like, this is such a waste of time.

Mike Landa: So let's follow that thread, yo, blah, blah, blah. It's because. So I said to you, well, what's of major interest? And you go, well that thing that I think your platform does, that's kind of interesting to us because it kind of solves this problem. And I'd go, fine, ok let me, let me show you that. For me a natural follow up question would be, well, what's the value of that? So I've proven that we can do that. How valuable is that? I don't mean give me a hundred thousand dollar. Yeah, whatever it is, but how valuable is it? And um, why haven't you managed to solve that problem before? They're reasonable questions, aren't they? As a follow on.

Alex Sobel: Yeah, I guess it's the way that you phrase it, right? Like there are questions that people will ask, like our guys and we have a huge sales team in the US and Europe. I mean it's got to be, it's got to be 75 to 100 people now. And the one thing that we always talk about is that what are they called? They're called um, the type of questions where like the answer is obvious.

Mike Landa: Right?

Alex Sobel: Yeah, yeah, we try not to. Like in a situation like this with a product demo, like, hey, this is actually what it does. Would that be valuable to you? Makes sense in my business, right? If I know the company's trying to sell to the enterprise, asking them how valuable would it be to be able to access these people? Like there's a way to frame it where the person doesn't think you're just trying to fill time and be, and be corny. It depends on the sale. The value question is the sale in the situation I'm giving you with the demo. Like, yeah, like he doesn't, the person doesn't know a lot about me. I said what I was interested about the product he's showing me or she's showing me other pieces about the product, understanding if I think those pieces are valuable. That's an appropriate question. So sometimes questions are appropriate or not appropriate depending on the situation.

Mike Landa: And this is because a lot of people will have been taught, for example, spin selling. Oh, I thought you might say that. So why don't you like spin as a methodology?

Alex Sobel: Because it's. Even though a lot of situations feel the same, they're usually not right. I'm like, if people think that you're trying to use a sales tactic on them, yeah, you're doomed.

Mike Landa: Yeah, you'll run a mile.

Alex Sobel: Or even if, like I'll give you an example. Even if you're reading a script, which I have no problem with scripts or outlines, the goal is to not have people not think you're reading a script.

Mike Landa: Exactly.

Alex Sobel: Even if you're trying to spin sell, the objective is for them not to think that you're spin selling. Like the cat's out of the bag on spin selling. So if you think spin selling is what's going to get people to work with you, like people have been through this. If spin selling, it just, it was a new idea a month ago and not a lot of people have been exposed to it, then yeah, you can try something that a lot of people haven't experienced. With us. When we talk to people, they're experiencing something they're not experiencing from any other type of conversation with someone that eventually is trying to sell them something. So I think the experience of being different, we stay away from doing things that are what most traditional organizations do. Spin selling being right at the top of that list.

Mike Landa: Interesting. Very interesting. So what are the three biggest things any kind of enterprise CRO sales director should focus on to drive sales growth in this market? So on the supply side, they've got big targets, big challenges, big numbers to hit. Especially if you're in the SaaS market, which is really challenging right now with kind of SaaS apocalypse, as they called it, and valuations. What are the three big things you think enterprise CRO from maybe tech and other companies should focus on?

Alex Sobel: Well, don't spend enormous amount of time with your marketing department trying to get old school lead sourcing tactics like getting bogged down in the details of how are my email campaigns, how are my salesforce cadences, how are my webinar strategy, how many trade shows are we going to. You got to meet people where they are, right? So if you're able to define the people you need to meet to get things in motion, right, you can do all of that. And I'm not saying not to do that, but one don't expect a lot from it because the stats prove out from very prominent businesses that track this type of stuff and explore this type of stuff, investigate these things that less and less are legacy lead generation tactics like, you know, all the traditional digital things people do to try to get access, even the trade show stuff. I just think that, uh, you got to try to meet people where you are regardless of who your audience is.

Mike Landa: And by meet them as in in person, um, have a face to face. The quicker you can get to a face to face, the better you got

Alex Sobel: to get access to them as best as you possibly can. Now most of the enterprise community is trying to get to the C level or like C level minus one Persona. So again, like I said to you previously, right, you got to deal with things that are out of your control. One being that these people move around a lot. So when you get in with someone, you got to stay with them because if you give it enough time, you're going to end up probably losing out, that they're going to go somewhere else, so they're going to get promoted or go to a different role. The second thing that you got to realize is that a lot of these tactics that you use, the email cadences,

Mike Landa: the lead generation stuff, the sequencing, nurturing, all that kind of stuff, I mean

Alex Sobel: you should do it because you may get some benefit from it at some point, but you can't just rely on that being the main thing that you do. Because most of these people at the levels that the enterprise are trying to sell to, they don't even look at their own inboxes.

Mike Landa: Right.

Alex Sobel: Their assistants are weeding through their emails and looking to delete people like you. That's why if you're going to do that stuff, you got to figure out ways to try to catch your attention. So I would say the first thing CROs should not do is not get so bogged down in the things that they can't control, like how much output they're getting from their marketing stack. Right. I think also the next thing they have to do is they got to make sure that they're looking for the right people throughout the interview process. I wouldn't judge every book by its cover. Right. I know it's easy because even when people come across my desk and they went to University of Pennsylvania, which is one of probably the top 10 schools in the world, you know, it's, it's easy to get excited to talk to someone because you know, to have done well at a school like that, uh, you had to have worked hard, you have to be intelligent and there's a lot of good attributes, but you got to be really careful about who you bring on board. And third, I would say especially in an earlier to mid stage company, as a CRO, you got to be in the trenches with your guys. If you're just spreadsheet focused, accountability focused in terms of data, and you're not getting into conversations, giving advice, getting on calls with people, meeting people in face to face with them, then you're giving up a huge opportunity and you're setting up yourself more to fail.

Mike Landa: Exactly right.

Alex Sobel: You people who want to go to war with you.

Mike Landa: I, uh, do a negotiation skill training program for uh, Clients, um, with salespeople. And uh, I did one recently and part of the negotiation skills training program is everyone gets a one on one with me. So they get a one on one negotiation session to coach them around deals. And what's interesting is I've now had, you know, 10 one hour sessions with the sales team. When I go and see the sales director, I've got all of this huge amounts of very granular data about what problems they're facing. And I can aggregate that, anonymize it so that no one's, you know, pointed out and say there are some really big, big things here that we need to get our arms around that will fix conversion rates or AOVs or whatever it might be. My view is, well, all of the sales directors should be doing that anyway, day to day. If you're not talking and coaching your team members, you'll never get the granular data. And without the granular data, you'll make assumptions at the aggregate level, which are normally a mistake.

Alex Sobel: You know what I find as well? The data is great. But what's also great is that how can you be seen as a domain expert in what you're teaching if you're actually not doing it?

Mike Landa: Yeah, like, exactly.

Alex Sobel: Like everybody knows at Millennium that if I do a training, it's like, yo, he's been through it. We watch him still. Like, I don't get the chance to sell much anymore, but I still make a point to sell some each year and so does Rob, because it keeps us fresh and it keeps us able to have street credit.

Mike Landa: Exactly right.

Alex Sobel: And we're not telling people to do things that we don't do. I think that goes a long way. You know what's interesting about negotiation, right? Back when, another time I had gone back to my university, University of Delaware, I, I went to a negotiation class, right? I happen to think I'm a very good negotiator. And one of the things I did to start the class, it was like 75 to 100 kids we took. I had someone come to the big board and on the whiteboard they wrote out, I said, what do you guys think are the do's and don'ts of negotiation? And it was kind of funny to see what they thought as college kids. And I said to them, I said, whether in your personal, your professional life, most people you're going to negotiate with more than 50% are not going to be honest with you because they're trying to get a better deal. And they kind of looked at me and they couldn't Believe it. I was like, it really doesn't matter what you're selling. Most of the time, the people that are going to buy from you, they're going to say mostly what they need to say to get a better deal. And one thing that I find really interesting in selling is I've had to work many years back in the early parts of millennium when I was way more in the trenches than I am now, unfortunately, where it was obvious that a person wanted to work with us and then asked for a discount. And then the person's knee jerk reaction was to say yes. And we would have the call recorded. And I would say at this point of the call, before they asked for money off, I would say, do you think this person's going to work with you? They're like, yeah, they're in.

Mike Landa: Why would you give them a discount? Why would you do that?

Alex Sobel: Because why would you do that? Salespeople are obsessed with. So obsessed with the victory that they miss the little things. Like so many people negotiating anything, they don't realize that how you negotiate. Like, you could want to work with me. Right. You could be like, I like Alex, I like the product. I got to do this. And then you could say to me, I'm going to ask him for a discount because one is, I may need one and it may help me, but I want to see what he says, because why not? You don't ask, you don't get how

Mike Landa: I handle that, uh, exactly. Is really important.

Alex Sobel: It may make you be like, that was strange. I'm actually not going to work with this guy.

Mike Landa: Or it may make you go, I absolutely want to work with Alex.

Alex Sobel: Yep.

Mike Landa: Because he understood we can trade things, but we're not discounting a premium product. Yeah, you want it, you're in.

Alex Sobel: We'll discount on situations. Like we're not opposed to discounting every now and then. But salespeople are so obsessed with getting the win that they don't realize that higher price deals, like, it's better for the long term relationship to stay strong and defend what you've pitched as value. Like, you know, back in the day, I remember at my old company, someone was on the phone, the person at the end of a call said, yeah, this is too much money. And the person said, yeah, I probably could do this for like 50% off.

Mike Landa: Off. Wow.

Alex Sobel: I want to literally run through the wall.

Mike Landa: Yeah.

Alex Sobel: I wanted to take the guy's head and squeeze it. And I think salespeople oftentimes are so obsessed with just getting the logo that they actually don't realize they're blowing out a lot of their own deals because of the way they handle negotiating.

Mike Landa: We could have an entirely separate episode about negotiation. My word. Whenever I train people, rightly or. And I'm cautious, Alex, because you've got 100 salespeople. So of all the people I meet, you absolutely know what negotiation is about because you've got 100 salespeople who are successful. But I've got mantra which I say to salespeople, which is, stop discounting and start trading. And I say that because as a buyer, if you offer me it's 100 grand, and I say, Ah, no, I can't do 100 grand. We're at the end of the sales cycle. And I'm like, look, I've talked to your competitors. I reckon the other market price for this is probably about 70, and your particular offering is below market. So I'll take 60 and I'm done. If the salesperson says, can't do 60, but I could do 75, two things happen in my mind. First thing, you were basically scamming me. You overpriced it in the first place. And secondly, you've gone to 75, you'll get to 55, maybe 60. So it's like it has completely the opposite effect that salespeople think it has. It's the really, really, really worst thing you can do, in my view.

Alex Sobel: It's rampant, too. Yeah, it's commonplace. Um, it's commonplace. And you got to work. You know, I live by this quote, right? The chief object of education is not to learn things, but to unlearn things. One of the reasons why we do hire experienced sellers, but we like people with not a ton of experience, is because they don't have any bad habits.

Mike Landa: Yeah, exactly.

Alex Sobel: And people, I see this with, my 5 and 7 year olds, I got to remind them of the same thing a million times. It's the same thing with salespeople because it's your gut versus your head. Your gut is what makes you feel good or bad. Your head kind of tells you don't necessarily like. It may feel good to not push back when someone's trying to ask for a discount, but if you know it's the right thing to do, you always, you know, you kind of think with your head. But, but listen, we have about 27 figure clients a year, right? We have 20 companies that spend over a million dollars a year with us. And I've walked through examples where someone is spending over a million dollars with us. And because they're at that scale, they do get perks. There is discounts based on scale. And then at the very end, I was in a situation where a client of mine for a long time was like, alex, I know you've given us the traditional discounts based on the volume we're taking, but I need another X off. And I knew that was the conversation coming. So I took that video call in a room where there were 20 salespeople around me, but they couldn't see them, the client. And before I got on the call, I said to them, the video, I said, let's map out what we know. Yeah, right. And basically I got them to see without me telling them that, well, they've worked with us for years. They've already gone through some of the discounting already. I know they want to work with me again. And I said, one is, I'm not discounting anymore because I've already been generous enough with them with the scale discounts. And two is even if I wasn't generous, I don't have to. And one person was like, but what happens if you piss them off? It's over a million dollars. It's $1.4 million deal, $1.6 million deal. I said, it's not going to happen. It's not going to happen if I'm professional. And I got on the call and just like I predicted on video, the person was going to like, was like, I can sign this today if you give me another 25% off. Yeah. And we still got the deal. And the reason I did that is because a lot of these guys are working on smaller size deals than million dollar plus deals. And I said, it doesn't matter the price of what you're selling. You have to know what you're working with and what you're not working with. And when you have them bought in the leverage flips and you have to

Mike Landa: know the value of what you offer. Alex, you should come back if you would, at some point, at your convenience. And we'll have a separate episode on sales negotiation.

Alex Sobel: I would love that.

Mike Landa: I will book that in with you afterwards, definitely. So we're at the end of episode two. There might be an episode three listeners coming up. What are the big takeaways here, Alex? Just give me a couple of things. Two or three big things that a listener, uh, would go, okay, I could try that tomorrow.

Alex Sobel: So one thing I would say generally, especially for younger people, is that, uh, when you're growing up and you're going to university or you're studying, there are options you can have that can give you a direct career path. Right? You could study accountant and be an accountant, you could study nursing law. But what a lot of people do is they study stuff and it doesn't give them an exact career path. And if you go down that road, the best thing that you could do is try to become a great seller. Because whether you stay in sales or not, whether it's in your personal or professional life, becoming the best salesperson you can be, as Mark Cuban likes to say, something like this, it's something that'll be with you forever. So I would argue even if you're going to go study accounting, you're going to have to deal with clients. So having some sales experience before that is good. But especially for the young people that are not having a direct outcome from direct things that they've done, which most people done. That's what I did. Most Fortune 500 CEOs have done. They studied history, you know, they weren't going to be a historian. The best thing that you could do is become the best seller you could be. And in order to see if you've got the type of personality to become the best seller you could be, put yourself in situations or jobs that most people wouldn't do because they think it's kind of beneath them. And the reason they think it's kind of beneath them because they deal with a lot of challenge and difficult people and asking people for things. And those are the type of jobs you should try to stress test. And I think that one thing for salespeople in general is you got to be really aware that if you're doing things that aren't working, no matter how good they feel, no matter how much they may make you feel better about a given situation, if something's not working, you got to change. And you should focus on what works, not what makes you feel better. Good. And I guess the final piece would be, is that selling, especially at the technology level, can be really a rewarding career. Selling in general could be a really rewarding career if you find the right company and the right culture. And it could be financially rewarding as well. But, uh, you got to know yourself and you got to make sure you work for a company that's doing things for the right reasons and has your best interest at heart. And you may not find that in the first couple things that you do. But, uh, even then. So it doesn't mean you should give up, because working in difficult environments can make you tough. But long term, you should seek that company that has got the right intentions for you, and it might take a couple companies and surviving at those companies to figure out what those are.

Mike Landa: Alex, it's been a real pleasure. A real, real pleasure. Thanks ever so much for joining me. Where can people find out more about you?

Alex Sobel: So I'm not that much seen on social media. I don't do much posting or anything like that. The best things for millennium mill-all.com mill-all and our LinkedIn page got everything that we do, all the time, internal and external stuff. So either of those two places would be the best places to find us.

Mike Landa: Brilliant. Alex, it's been a real pleasure. Thank you.

Alex Sobel: Thanks Mike. Appreciate it.

Mike Landa: Thanks for listening to Higgle, the B2B Sales Club podcast series with your host, Mike Lander. Please subscribe so that you'll catch all the next episodes.

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