HOW TO ASK THE TOUGH QUESTIONS THAT WILL WIN THE DEAL

Got a great one for you today. This is one that you want to save, and unfortunately, I should be charging for this, but I'm giving this one away for free. Great guest, great topics. Now imagine trying to sell process improvement software to huge banks down on Wall Street. Sounds easy, doesn't it? You're right, it doesn't sound easy. Sounds pretty difficult. So you got a couple of things. You got laggard accounts, meaning that these are big, large banks, 100-year-old banks in some cases. Got all kinds of legacy infrastructure, huge number of people, lots of money at stake, no room for error, and you're trying to change the way they do business. Now, you may not have this problem, but you may have it in a much lower altitude, maybe a smaller company, smaller change, but the same principles apply. The default is always going to be, let's push this off, let's wait, let's try and do it cheaper, easier, or simpler, slower. The killers of our deals. So I've got a guest today who is selling into that exact environment. She has got an enormous amount of experience and skill. So it's the perfect combination of intelligence, hard work, determination, and a lot of great experience that she is openly sharing with us. So get your notebook out. This is one that you might want to listen to when you're not on the treadmill. You can listen to it the first time on the treadmill, but maybe later in the week, sit down with a piece of paper and really write down what you hear, and then listen to it again, because there's a lot of things in here. I'll sum it up at the end, but what you're looking for is— what I get out of it is And what I'm getting out of a lot of these interviews that I really never thought about this year in my whole career was about asking the hard questions. And I did a whole office hours on this yesterday. So if you're in Closing the Complex Sale, make sure you listen to that office hours. It is gold because I, I use a couple of different types of questions That will get the client to give you the information without you asking the direct question that usually gives you the wrong information. Like, what's your decision-making process? I hate that question because I used to ask it all the time. And it's a trap because they feel like they should know it. So they give you some answer that has nothing to do with what the real decision— they don't know what the decision-making process is. That's our job, not theirs. That's why deals go to, uh, uh, no decision 80% of the time on these new accounts. Let's get into this interview. I'm excited for you to hear this one. Also, haven't you checked out brevitypitch.com yet? This product, it's the most exciting sales tech product I've seen. Certainly in the last few years. You know, most of the stuff I see, yeah, it's easier, you know, get contact information, get background information, get org charts. All that stuff is great, but it doesn't make us a better salesperson. It's mostly information. But how do we become better? You know, how do we take training and then apply it and treat this like what it is? A performance profession where we need to practice. We need repetition. We need to develop our skills. And we always wish we had that partner. And maybe you have had that at one time in your career when you both have free time and you do a little role play, or how did you do this? But we really have to Do it out loud talking. And I was talking to one of the founders this week and he shared what one of the customers— and the customer is a podcast listener, so that I won't mention the name because that's probably not appropriate without their permission— but they're saying it's amazing when you get the reps warmed up with it. Builds up confidence, develops skill, and it really increases your likelihood of being better when you do get a live person on the phone in that important meeting. So, check it out at brevitypitch.com. Tell them Brian sent you.

Here we go.

Hey, Teresa. Thanks for joining us today. As a way of getting started, give us a little background on yourself.

Oh, happy to do that. We'll keep this with sales. So I've been selling for, believe it or not, I actually had to look this up because I couldn't remember how many years, but it's been about 30, 31 years since I've been in the sales capacity. Clearly, it's something I'm very passionate about to be sticking around for as long as I have. But I do enjoy it. I'm in the Northeast. We relocated from California to Cape Cod. It's been a really fun transition and it's great to be here with you today.

Great. And what are you passionate about sales? How'd you get into it? What do you like about it? What keeps you involved?

You know, it's funny, a lot of people had said many years back, you should really get in sales. You just have the right personality. You're approachable. You like talking to people. It wasn't on my radar. I think when I was in college, I told all my friends the last thing I will ever do is go into sales. And yet here I am.

30 short years later.

Yeah, exactly. I think I love it because it stretches your skill set as you start to move up in the role. It's very challenging. That keeps it interesting. And, you know, obviously there's a huge reward at the end of the hard work that you put in. So all of those things are probably why I continue to do it.

And you've had a great track record selling some pretty hard stuff too, right?

Yeah. Yeah.

What attracts you to the hard stuff?

Yeah, I don't think I know that it's hard till I get in it, but it goes along the lines of I think if you're passionate about sales, you don't like hearing no, and you really wanna make yourself relevant to the folks that you're selling to. And in order to do that, you, you know, you've gotta be challenging. You've gotta be selling something that's kind of breakthrough technology. I'm in the software industry, and that's what people ultimately want. They want something that's gonna take them and their business to the next level. So, you know, there's nothing short or boring about it. So I just happen to continue to follow that.

And you've sold to a lot of different personas too, haven't you?

I have. I sure have. Yes. Great picking up on that one. Yeah. And I'd have to say, you know, I'm probably at the top of my game here in terms of the level that I'm at selling. I sell to the banking industry and we really are at the executive level. You know, a lot of people say I work with executives and they might be VPs, but, you know, we're at the C-suite and it's truly fascinating and you see a lot of passion at that level and it's more of a business discussion and it's not about the product you're selling and I truly enjoy that.

Well, let's dig into it. What's the title of the person that you most commonly want to talk to?

So typically when we start out, we want to be, you know, these would be managing directors. So an MD, somebody who oversees all the operations and is focused on process improvement or process optimization. That's the solution that we position in the banks is to help them really, you know, move faster, scale faster, but more than anything, be innovative. And a lot of banks are really striving for what's called the T+1 trades. And we have a huge success track record in that particular area.

And it's got to be competitive.

Right?

Super competitive.

You wanna know what's funny? So the company I work for, am I allowed to drop the name?

If you'd like.

Alright. So the company's called Celonis and we trailblazed this space for process mining and what that has done. And so you wanna talk about hard, it's very hard in the beginning to get people to understand what is that. So you have to be quick and to the point when you're explaining and educating, right? So that it's not overcomplicating the definition. But in that, because so many companies, not just in banking, really, it was picked up by manufacturing first, which, you know, they're often sailing into the sunset. Those of us who have been working with banks, it's taken a little bit longer. But we've created a need. And so now there are a lot of competitors in this space. And quite frankly, that's a good thing. Yeah, that means we've done our job.

Yeah.

Right.

You know, because I sold that type of thing on the development side. Okay. So I kind of sense, and what we always ran into, there's a lot of ways to skin the cat.

Yeah.

And everyone's got a different way and a different value set. How do you keep them focused on your value set?

That's a good question. I hear how other software vendors are positioning themselves. And I certainly don't want to sound the same way they do on this call. But it's really Actively listening to what the banks need today. They're all focused on, you know, either risk avoidance, risk management, cost takeout is a big thing, and growing their top-line revenues, you know, wallet share. All of that is really important to them. And that's what we play into because we have, again, many other stories that we can share. where we've impacted all or maybe one or two of those specific strategies that they have. And really, at the end of the day, it's about us showing them proof before they jump on board and really take on the product across their firm and showing them that all of this waste in your business process is costing you this much money. Wouldn't it be great if you could roll that back into the organization, create capacity by eliminating all this manual intervention? And, you know, we're talking hundreds of millions of dollars, and that gets their interest immediately because who doesn't want to save in the millions, if not, you know, much higher than that? And that's on an annual basis.

And how do you keep that sale progressing? Because it sounds like you could have a lot of great presentations, demos, proof of value, economic discussions, and I bet the product is well worth its value, which means it's expensive.

It's got some value. You know, I think you have to have a framework and you clearly know the sales motions with what you described. But that doesn't mean that everybody follows the framework. Some people probably wing it. I've seen people wing it. I think it's about being prepared, being an active listener, being very relevant to what their needs are. And I think one of the best things that I love is pivoting in a meeting when they've decided, okay, we get all this stuff, we want to know about X, and not being afraid to move to that discussion. I've seen people make the mistake of, well, we'll get there in a minute. Let me continue to tell you how great I am.

Yeah.

And I think you've lost credibility at that stage. You know, that's part of, I think, why some of us have higher success than others. And then of course, um, I like to put like a sequence of events together and make it a mutual action plan with the prospect and show it to them. Hey, here's this sheet of all the things we have to do from, you know, kicking off the POV to getting you to sign an agreement. Is there anything else in here that I've missed? And of course there will be. And they're like, this is fantastic. I don't even know all the answers. Let me go get those for you. That doesn't make it go faster because there's a lot of stuff that happens once you get to legal review. But it certainly expedites the process if you didn't do something like that. Do you know what I mean?

I gotcha.

Yeah. Yep. So I think when you start to show them that you know their business, that you understand what they need, that what you have can help address those needs, and that you actually have a real plan in place to help them get there. That's a game changer.

Yeah. And what's the hardest part of this sale? Oof. Um, we should ask what's the easiest part.

Everything, right? Exactly. It's tough, especially in the, the you know, conditions of the market, this has been a tough year. I'll be the first to say, you know, out loud that it's been the toughest of my entire career.

Right.

So looking at these 30 years, it's been really tough. Now, having said that, at the same time, I'll say all the days and weeks that you're thinking, what am I doing? Am I— is this the end of it for me? Because I just don't feel like anything's happening. Then I plug into your podcast, I get what I need from it, and it kind of fires me back up. And it's, you know, you're gonna go through times where it's gonna be tough. But what I love, one of my favorite podcasts is when you talk about get creative. And that's a lot harder than anyone can imagine when you sit down and think, well, how can I be creative? It's tough.

Yeah.

But when you can figure out another way around where you might be stuck. And, you know, in my case, I figured out a faster way to make my engagement more meaningful and deeper within one of my banks. And they partnered with me to help broker introductions. And as a result of that, we went from kind of a flat discussion to an executive alignment meeting. And I think that's being creative. You have to step back and think, God, I've done everything here, but there's something I'm missing.

Well, because buying your product is not a natural event.

Correct.

It's an unnatural event.

That's right. Yeah. Yeah. Even if they say, and there's many people today that are focused on process optimization, but it means something different than applying our product. So there's still some level of education. For sure. Um, the market has changed the speed at which people are ready to pull the trigger, right?

Yeah, because they've lived up until now without it.

Yeah.

And you're trying to create a compelling event that would trigger the selection and the execution of a purchase order.

Exactly.

And I gotta believe whoever has to approve that Number one on their list is wait. Nothing against the product, nothing against the ROI or anything.

Right. That's right. It's understanding early on, where are we on your list of priorities, the projects that you have in your, you know, view, where do we sit? And then you have to figure out how can we elevate and take that number one spot, which everybody's fighting for.

Everyone wants it.

Yeah.

Especially this time of year.

Yes.

And you bring up active listening a couple of times. What does that mean to you?

Listening to you?

Active listening.

Oh, active listening. Sorry. You know, some people, I've seen them sit back and they're ready to say the next thing. And they've kind of missed the meat on the bones in the conversation. And if you miss that, that could make or break an executive meeting because you've suddenly not become relevant to them. And it's not just listening to what their needs are, but listen to the words that they're using. Bring that language into your presentations, into your talk tracks, into your engagement with them, because then it's kind of like mirroring. You sound like they do, and you're both actively listening now because there's a partnership in your language. And I think that's really important.

Do you have a particular way to dig deeper? Because, you know, these polished executives, you know, there's probably 3 levels before you get to any meat on that bone, right? It's a lot of fluff and politics and—

Yeah.

You're looking for the meat. You're looking for that problem that's bugging them now.

Exactly. Yeah. So I have an example. We have an existing customer. We want to do an early renewal with an expansion on the current agreement. They're not ready nor near ready. And we've had to create urgency. And it's— that is a lot of work too.

Yeah.

So that's when you really have to tune in and you start to see where some of the gaps are and maybe what you know. And we've spent the last, you know, let's call it half a year really helping them utilize all the capabilities in the platform and make us not only stickier, but attach ourselves to other key programs that they're focused on. And in that, you can lose sight of what the goals are for them. And you get lost in, have we done this, this, this, and this? Well, yes, we did. Okay, now let's put the proposal together. And I think a lot of strategic AEs are honest with themselves. I try to be, eyes wide open. And when we put the proposal together, I said, we are missing some stuff. I don't think we know what they want anymore. I don't think we understand their goals because we've been in the weeds to help them use the platform.

Right.

Now we need to go back up and understand what are their business goals and how can we tie ourselves back into it? Because what we tied into, you know, several years ago is not what they care about today. And so you really have to evaluate what you know.

Yeah. And look at it from their perspective because that's what I heard you say.

Yeah.

Yep.

And run it by a couple of people. Maybe you, you know, If you're gun-shy about running it by the economic buyer or the executive sponsor because you don't want them to know what you're ultimately preparing for, you know all the people around them and you know the people that are the closest to them. Ask them and they'll tell you exactly what you're looking for. And I think that helps when you're trying to do something sooner than the customer wants to do it.

And what do you think is your strongest sales characteristic?

I don't know. I mean, you know what people call me? Machine Gun.

Really?

They call me Machine Gun Theresa. I think because—

I was thinking that when I first turned the camera on.

Yeah. So my initials are MGT. Oh, and so when we are— not my real initials, these that they've given me, right?

Just a tattoo on your—

Exactly. That's right. So I think I've earned, gained, been given that because I can get a little bit bullish about what I believe in. And I'm not your typical sales rep that's gonna sell you a bunch of crap. I'm not gonna sell you something if it's not gonna work. If I don't believe it, I'm not gonna position it. And a lot of times you're not talking to the right person at that point anyway, right?

Yeah.

I get bullish and passionate and I get kind of intense and I don't know that, you know, I've never really known that that's been serving me, but according to people around me, They think that's what has really been unique about me as I go after it, and not in a jackass kind of way, but more firm, authoritative, um, confident, and convincing. And confident. Yeah, confident.

Because I gotta believe that in these meetings there's questions that are just itching to be asked. And you may not have asked them 10 years ago before you became the machine gun, right?

Oh, yeah, most definitely.

But you probably learned over time, you don't want to waste your time.

I don't. And, and that's a good point. Because there's also an area where I'm a little bit fearless. And that is God, we really need to get to the CIO. If we can't get to that CIO or COO, things just aren't going to move. All right, let me make the call. Let me send the emails. Ooh, let me send the LinkedIn note. I care enough that I don't care, if that makes sense. What have you got to lose? You don't have anything to lose because you don't have anything right now anyway. And, you know, if we have bankers, those are the people who, you know, want to engage with us and obviously be a part of us going public. I've met some of them along the way. And a lot of people are a little bit afraid to talk to them. And I just, I'm not.

And this is something you've developed, I assume, or were you, were you like this as a teenager?

No, I would say that's developed. Yeah, I would say that's developed, right? You as a young salesperson, the strong ones are always fearless. And yeah, they could pick up the phone and do those same things. Do they know what to say to get their attention? You can tell the difference And positioning between where we are today and where they are just starting out.

And that ability to ask those tough questions is a critical skill. Because, you know, how long did it take you to get into that room with them face to face? Long time, right?

Yes.

And you leave without the answer that you want. Or answer to questions that you need the answer to.

Right. Yes. And leveraging your champion. A lot of champions are also coaches. And we do a lot of prep with them and want to know any and everything about who we're going to be meeting with at the executive level with our executive team. And you definitely cannot be afraid to ask them questions no matter how obvious it may seem, if you don't know the answer, you gotta ask it. Because if you don't, your leader's gonna ask you about it. And if you don't know the answer, they're not gonna think you're doing your job. Yeah.

And what kind of gave you this skill? Was there a deal you lost early in your career or you saw someone else do it? Or you just got sick of not asking the tough questions and standing up for yourself? And because let's face it, we work on commission. We're here to sell to people who need our product.

Right. Yeah. I think it was more about, look at those reps that are crushing it. And as a younger salesperson, how are they doing that? What are they doing? And I want to get to know them. But I think also, you know, getting close to your own leaders, you know, no matter how wide or how high you want to go in that, and others in your organization that are just wildly successful, the way that they present themselves, the way that they position things. I always wanted to learn from those people, and it may be inactive learning. We could all be in a room, and they're not necessarily coaching or teaching me, but I'm picking things up as they talk about whatever they're covering. Oh, that's— I need to do that. Okay, that's a good one. So it was more about, I want to be really successful. And I'm gonna listen to the people that already are, that are genuine. I think, you know, there's a difference between the credible, genuine sales folks versus the ones who will sell you anything and they could care less about you as a person.

Yeah, kind of the empty suit who might have the backbone to ask for the meeting but doesn't know what to say in the meeting. So they bring an engineer with them and they Yeah. They're totally dependent on the other person to ask any legitimate question other than how many and when.

Exactly. That's right.

And do you have like a mental model of these deals that kind of works for you? Some people look at it as projects or puzzles or challenges or battles or Challenges.

I'd say challenges. You know, I'll, at this level, we don't have, you know, lots of accounts. So it makes you dig deeper and try and figure out, well, how can I break into, you know, this account? Who do I need to talk to? Who do I need my team to Start leveraging relationships, engagements with. And honestly, sometimes when you get that first meeting, it's like, oh my God, this feels like an order because it takes a long time. You said it yourself. It takes a long time. You have to date. In today's business economy, you have to date that account for a long time. Before they're ready to say, all right, we trust you.

Not Tinder.

Definitely not Tinder. No, Tinder does not write the checks. But you know what I'm saying? Like, they really need to see that, A, you're committed, you're invested, and you really want to do business with them.

Right, because it's such a big decision. It involves so many people and so many things, right? Keeping that momentum moving is really challenging.

It is.

You know, because I don't think anyone will say, oh, the product doesn't work or we don't need it. Well, you can figure that out long before you get in there, right?

Right.

But once you're in there, there's a lot of reasons why they won't do it. that have nothing to do with you, your product, even budget.

Right. That's right.

What do you think is the most important skill you've learned that you don't see in other people, other than that's the backbone and asking the tough questions?

And I really think it's active listening. I don't think a lot of people do it. Listen to all of them. I think many, um, it's that 80/20 rule. I would say 80% really don't. They aren't present in the conversation entirely, or maybe they don't know how important it is to sit back and be quiet and listen. You probably know this. Sometimes you ask one question and, whoo, They could go on and on and on, and you just get your notepad out and keep taking notes. And there, if if you don't get to the line of questions you thought that you needed, it's going to come out in the information that they're sharing. And I just feel like people are ready to ask their next question, ready to talk about them, as opposed to sort of taking a deep breath. And being quiet.

Yeah, because we know about us, we don't know about them, right?

That's right.

And yeah, I'm getting the sense that being able to empathize and understand what they're up against and what they will end up doing is something that's going through your head in that meeting.

And sometimes you don't even return any kind of information. You want to take it away, digest it, give them enough to keep the excitement. Obviously, you have your next call to action or meeting ready to go. But you take all that back, and then prepare what your next positioning conversation is going to be with all of your, you know, asks in mind.

Yeah.

Um, it's, you know, observing, listening, collecting. It's kind of like a doctor. When you go into the doctor's office, they want to know a lot about, oh, your stomach hurts? Okay, so are you feeling this? Are you feeling that? They're trying to diagnose you. And then even if it's, well, we need to do some more imaging, They're not going to tell you what they think it might be, even if you ask them, well, what do you think it's going to be? That's why we're doing the imaging. It's kind of the same thing. They take it, they collect the information from the images from you, and then they present, here's what's going on. That's how I like to look at it. I've spent a lot of years in, uh, with some life-threatening stuff. So.

Yeah.

Cool.

Hey, Theresa, appreciate your time today. Where can people go to connect and follow you?

Oh, on LinkedIn, Theresa Babolero.

Also known as the Machine Gun.

Right, exactly.

Isn't it nice to hear 30 years of sales experience kind of condensed into about 30 minutes? Now, there's so much in this that we could talk about. We could talk about the creativity and the mindset. But what I would suggest is thinking about what characteristics you need to get to your next level in sales. And it kind of starts with a little bit of confidence. Because it's hard to be creative if you're not confident. But I think a lot of salespeople today are making this huge mistake. They're trying to learn as little as possible to get the next step within a deal. How do I get my email opened? Okay, now how do I get it read? Now how do I get them to reply? Now, this is okay, but what happens is you don't understand the whole game. You don't understand what they're thinking when they receive it. You're not thinking how they think. Now, empathy— I'm starting to think that you need empathy to be creative, because how do you create something that works if you're not thinking Hmm, I don't know. And what I heard was a lot of those hard questions, you have to understand how deals progress and how companies buy so that you can think about what that next step is and guide your champion through the process. And maybe even act like your own champion. We had an episode a couple weeks ago talking about that, and I did a couple of office hours on that. Because what happens if your champion isn't that strong, like in the case of the rep acting as his own champion where he sells to even-keeled buyers? He becomes his own champion. He looks at the deal, these large deals, as a project. He references different groups within the company, no single-threadedness. And I think today we are only doing things when we have to instead of preemptively, proactively. And a lot of reps are acting like service reps. Where it's all about knowing about the product and giving the client what they want and not understanding where it is and just following up, following up, following up with no value. All of these things are skills that you need to learn, and frankly, you need to learn them early in your career before you've got bad patterns and habits. And today I think we've got this real challenge because a lot of the managers grew up in this activity-based selling. And activity-based selling works when you're order-taking. It does. It's retail. Okay, people are coming in, want to buy. Activity-based, reactive. It can work if you get that kind of inbound. But most of us don't. Most of us get no inbound or bad inbound, because bad inbound is worse than no inbound. Because you have to process it. You have to mark it up in the CRM and pretend that this Gmail account is a worthwhile lead. And this is where marketing has really done a disservice to sales by focusing on just getting contact information instead of interested people in the product and the problem that you solve. These are challenging times for salespeople. But they don't change our comp plan because we have challenging times. They probably make it a little harder. Treat this like the profession it is. Go to b2brevenue.com, and I solve 2 major problems for sales reps like yourself. How to get meetings and conversations started with strangers. Start the conversation, get the meeting. The second is, how do you close a complex sale? Not just participate, not service it, Close it. Because unless you close it, it's just academic. There's no commission on no decision. Try and talk your payroll department into paying you for your pipeline. All that stuff is to keep your manager off your back and have them create pretty slides and meetings that you're not invited to. What we care about Is closed won. And to do that, you have to understand how companies buy. Anybody can service an opportunity, update a proposal, hound people, but that's not selling. You might have some opportunity where that's enough. Most cases, we have to do a whole lot more. We have to know How to get this done. And your manager's not going to teach you this. Your manager's only seeing the best of the best deals. So they think it is easy. They think it is just activity. And I got into this argument with a manager this week who says, you can have both quantity and quality. And I go, you're an idiot. I go, and I drew an— and I don't know why I spend time with these people. This is free consulting I was doing for him. And I go, look, you get an axis. You've got time on the bottom end and quality on the top end. And as quality goes up, it takes more and more time. So you can either do a lot of no quality or low quality activities or a few high quality activities. You can't be in 2 places at once, even though you'd like to. Even you say you can doesn't make it possible. So, he kind of acquiesced after I showed him that. And I go, well, you know, the right activity— and everyone kind of rationalizes that insane amounts of activity drive revenue. It does only in the case where it's really a simple sale. Once it becomes complex, more than one decision maker, it's over $5,000, $10,000, where you can't buy it on a corporate credit card, if it's a new product that people don't understand and there's no paperwork already in place, those things increase the complexity of the sale, which requires Better planning on our side. And the problem is today everyone's focused on the quantity, but you don't get paid on quantity. You only get paid on the deals that close. So being busy with a whole lot of pipeline that doesn't close doesn't pay. And this eludes people because We like being busy. We're distracted from the scary thing about our income is so low. And I fought this my whole career. It's just, there's a lot of dumb people get put up into leadership and they don't understand sales. But that doesn't mean that they're going to change the comp plan to fit their mental model. They expect us as salespeople To sell their way, but get the results in a whole different way. Because I remember so many times managers, you know, they fly you up to home office and tell you how to sell and where to sell and how big the deals should be and how little support you should give. And I would be like, well, if it doesn't work, are you going to pay me? Of course not. And if it doesn't work, who are they going to blame? You, the sales rep, not them and their bonehead strategy. They'll reference one case where it did work, where the, you know, the golden territory where somebody got a big deal fell on their head, and they say, well, that's because it worked there. It's up to us. We own our own training. We own our own skill set. We own our own outcomes. Boy, I get passionate about this, don't I? If you're serious about sales, go to b2brevenue.com. Sign up today. Uh, there's 2 major videos on it. There's how the courses work logistically, and then there's how to pick which course. And it should be pretty simple. Do you need meetings? Do you have like zero pipeline, zero inbound? Then you need meetings. You need conversations started. Or you got a lot of stuff started, but nothing's closed, or it's not closing fast enough or big enough. That's closing the complex sale. We'll see you next time. Check out brevitypitch.com, and if you see my stuff fly by on LinkedIn, give it a little like, a little comment, a little share.