(888) 815-0802Sign In
revenue - Home page(888) 815-0802

How to Improve Selling, with Bridget Gleason [Episode 757]

Bridget Gleason, Head of Sales and Customer Success at Tidelift, joins for the final episode of the Accelerate! podcast. What!? That’s right. We have some HUGE changes coming to show next week. Tune in today to learn what’s happening.

Key Takeaways

  • Bridget has been a guest on Accelerate more than 100 times! Andy and Bridget discuss A Mind for Sales, Daily Habits and Practical Strategies for Sales Success, by Mark Hunter. Curiosity is a great fit for sales if you do the work.
  • Bridget wasn’t satisfied in her career until she got into sales. She desired to talk to customers. Andy brings up hard parts of sales. Bridget doesn’t know of a job where every aspect of it is enjoyable. Make your calls first.
  • Bridget refers to Brian Tracy’s Eat that Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time. Do the hard things first to get to the fun stuff.
  • How do we enable sellers to perform to the best of their ability? Andy lists five factors: skills, behaviors, mindsets, mentors, and experience. What skills enable you to perform at a higher level? How did you learn that lesson?
  • Andy considers listening and asking great follow-up questions to be top skills. The right questions help you to understand the buyer’s needs. That provides great value to the buyer.
  • Bridget shares one of the worst sales phone calls ever made to her; it angered her! It takes lots of practice to make good calls. Show reps how to ask questions and get needed answers without using a scripted checklist.
  • Bridget wasn’t allowed to make a sales call before taking weeks of training. Investing in training pays off in making sales reps more effective. If SDRs were paid more, would they stay longer?
  • Bridget describes Tidelift’s team-selling model. Each member is comped on the total sales number, by their experience. The work is more interesting for everyone. Bridget describes the levels of sales roles at Tidelift.
  • Andy would like to see highly-skilled senior prospectors on a career path starting with SDR. Bridget talks about the professional BDRs she saw in Israel at Logz.io. Would it ‘take a movement’ to have those in the U.S.?
  • Andy says you learn to sell from your customers, your peers, your managers, your mentors, and books. Some of Andy’s mentors were CEOs who were his customers. He recalls the video training he received, which he laughs at.
  • Bridget’s training was very valuable. At Wang, the top reps taught the new reps. Andy visited a retail CEO who mentored Andy to sell to him. Cultivate the relationship before asking for the order. We sell human-to-human.
  • Andy has told customers when his product wasn’t the right fit. Years later, he did business with some of them under more appropriate conditions. Bridget says it’s also the right thing to do. Be trustworthy.

Episode Transcript

Andy Paul  0:00  

Welcome to Episode 757 of Accelerate the sales podcast record. Joining me on the show today Bridget and I are going to focus on how to enable improved sales performance. Let’s get into it. Bridget, welcome back to Accelerate.


Bridget Gleason  3:26  

Andy. It feels like old times.


Andy Paul  4:01  

Yeah, I mean for more recent listeners, Bridget was usually on at least once a week, if not more sometimes. And for a period of  three and a half years, something like that. 


Bridget Gleason  4:19  

It’s amazing. We had so many things to talk about, but maybe not. I think we can recycle over a lot of topics just fine.


Andy Paul  4:31  

Well, actually, you know, when you go back and look at the statistics, many of the episodes that Bridget and I did together, we call them frontline Fridays, because they came out on Fridays, and we’re talking from the frontline of sales. They’re still some of the more popular episodes over the history of the show over 755 episodes, so.


Bridget Gleason  4:55  

You know, I think maybe being on the front line, misery loves company. And I shouldn’t say misery because I love what I do. Like I choose to be on the front line. But there is a lot of intensity, a lot of pressure, there’s a lot of things happen in the frontlines. So you need your people around you as you’re going through it. So I think there’s probably part of that, that it’s kind of the collective community coming together.


Andy Paul  5:35  

All right, so a question for you. So I just read a new book by Mark Hunter. Yeah, and called A Mind for Sales. So do you have a mind for sales?


Bridget Gleason  5:55  

Been doing it for so long. 


Andy Paul  5:57  

You know, intuitively does it feel natural or it’s something that takes more that you got to think about that too. You know, I’ve sort of thinking about that myself is, if I have a mind for sales.


Bridget Gleason  6:18  

Okay, so yes. I feel I have a mind for sales. And yes, I think it also takes work and cultivating Hmm, I think, for me, I’m curious about things. And sales is one of those things I’ve always been curious about. I think sales has been interesting to me. It’s the human part of it. It’s the problem solving aspect of it. It’s, you’ve got something you think about other people can benefit from, how do you make those connections? So I think it’s that part of it. I think it’s just really interesting. There’s a lot of psychology in it. A lot of I don’t want to say drama.


Andy Paul  7:28  

I agree with you on those first two points. I’ll just interject for a second. For me, I came out of college with, I like to say, no discernible job skills whatsoever. And all I had was this sense of curiosity. And sales seem to be a great fit for that, right. I mean, if you’re sort of almost curious to learn about other people and what they’re doing and how you can help them to your point about problem solving. Yeah, serve a great fit in that part. I still cultivate the mindset. Hey, make those calls, get cold calls, do all the things you had to do to get the opportunity to be curious about somebody.


Bridget Gleason  8:11  

So you know what’s so interesting? So my father was an entrepreneur and his background, I think, was kind of economics, probably accounting and that. But my father always encouraged me to either go into the military, which I do, okay, because he said I could travel. Okay, I’ll find other ways to travel and the other was he always wanted me to go into sales and I told them, no to both. So I graduated from UCLA with a degree in English in business, although I taught at an engineering school. And my first job out of school was in marketing. So I’m clearly going squarely in the face of my father’s recommendations. And it was probably a year in, I was in the computer and networking division at Xerox and I was doing a lot of competitive benchmarking. And I started thinking I should be talking to customers, I know how to talk about this. I feel too disconnected. And that’s when my understanding of sales shifted and so having a mind for it was different than what I felt my father was proposing. I thought, I don’t want to be like a car salesman knocking on the door. I don’t know why. But once I understood it in a different context.


Andy Paul  10:17  

So for me, it was more like the parts of sales that I didn’t like or didn’t come most naturally to me. I needed to do it and get to the parts I really liked. And so that was sort of the motivation right? I mean, to be able to talk and have a great conversation with somebody learn about their business be able to help them know then to go do the things I didn’t really enjoy which is going out and making cold calls and prospecting.


Bridget Gleason  10:43  

I don’t know of a job, maybe there’s one and I just don’t know of it, where every aspect of it is enjoyable and you feel energized by every facet of the job. Have you heard anybody say that? And I think sales is the same. No, I don’t wake up in the morning thinking, Hey, can I get up and make some cold calls today? But there are certain parts that are, by the way also as a VP of Sales. There are a lot of things I don’t like either that have to do with often spreadsheets, but that’s part of the job.


Andy Paul  11:28  

Yeah. But there are people, you know Mark Hunter who is, you know, very motivating, self starting. His book is full of, Hey, wake up your calls. I think there are multiple paths to success. As you said, none, there are parts of every job you just don’t enjoy as much as others. But yeah, you sort of pay the price to get the parts you really like.


Bridget Gleason  11:55  

Maybe it was Brian Tracy which most people won’t even know who he is because he was decades ago, regular people all right. I think one of the books he wrote, correct me if I’m wrong, Eat Your Frogs First. But basically the book says do the hard things first. 


Andy Paul  12:42  

Well, another question for you. So I have this theory. And that’s not really a theory, I think that’s borne out, in fact is that we don’t spend enough time thinking about how do we enable people to perform sellers to perform? I mean, in that let me restate that is that, you know, we have this sort of big trend going on and sales about sales enablement. But that seems to be so narrowly focused. It’s like, how are we just bringing people sellers to the table in order to sell as opposed to saying, how do we help them perform to the best of their abilities? I think I sort of five things that that are enable performance. So now, we have to enable skills, behaviors, mindset. And then there are, I think there are other things that enable performance are mentors, and experience. So I want to explore for you, it’s like, what was the single most important skill that you think that you learned at one point in your career that really enabled you to start performing at a higher level?


Bridget Gleason  14:48  

A skill that enabled me to perform at a higher level and what triggered them? Actively listening, you’re going to miss things and you’re gonna you’re gonna miss cues as to what a prospect wants or doesn’t want. If they’re really a qualified prospect or not. I think it was just a lot of trial and error. If I was really listening, and actually really trying to solve their problem. First of all people can pick up on that when you’re really listening or when you’re just nodding but you’re not really listening. You’re just waiting right for the other person’s mouth to stop moving. People can tell So I think listening, I think listening is such an important skill to have in sales.


Andy Paul  16:09  

I probably agree with listening. I think it’s coming. I mean, it’s paired with this idea of being able to ask great follow up questions. And so I think those two go hand in hand. They’re asking great questions. It’s not the first question that’s most important for me. I feel like one of the things I learned from an early boss was, have a great follow up question, but you don’t know what to ask. Unless, to your point, you’re listening. I think the thing that a lot of sellers don’t really understand, we talked about creating value for our buyers, and I believe one of the biggest sources of value we can provide to a buyer is to understand them.


Bridget Gleason  16:52  

Yes, understand them and the context in which they’re operating.


Andy Paul  16:57  

We think what empathy is. I can feel what you’re feeling, right? I feel I understand what’s not understanding how they feel to understand why they feel the way they do. That’s true empathy. Oh, it’s what cognitive empathy, which I think is the most important thing to have in sales as opposed to compassionate empathy. And so not that you don’t want compassion and compassion, but it’s the cognitive empathy, which says, Yeah, I now understand them more fully. And this is a real source of value to the buyer to feel understood. I mean, it leads to increase levels of trust and the way things are smooth the path actually getting the business.


Bridget Gleason  17:42  

I would agree with that. It’s the cognitive empathy. Sometimes, you know, getting back to asking the right questions sometimes getting the right questions, also help them to have a better understanding of both the problem and potential ways that they can solve it. So I think great salespeople help to clarify issues and clarify potential paths to a solution and help bring some of that together. Also, the best way to do it is just to know what questions to ask that surface that bar.


Andy Paul  18:27  

But that can vary from situation to situation. That’s where listening becomes so important. I mean, if we’re too scripted, we miss those opportunities to ask those great follow up questions, which may not occur to you till you hear what somebody has to say, really hear what someone has to say.


Bridget Gleason  18:42  

You know, Andy, I was on the other end of a sales call recently, and I won’t name the company. It was one of the worst I’ve ever been on and I felt so angry. And part of it just to set the stage. They had, they’re obviously the ones that initiated the call. There were two of us on the call and seven on their side, which is a huge imbalance. There were never any introductions. They just launched in and said, so Bridget, tell me what is your job? What’s your job? First of all, I thought did you do any research on who I am and what I do, because it doesn’t sound like it. And I had said it after I responded to that. Can you let me know who was on the call from your side. It’d be really fun for me to know. And then she went into what felt like an interrogation. Just a list of very scripted questions. What are your goals? Do you have one on ones with your team? Of course, I have one on ones with my team. Are their goals for the team? Some of them were so basic, and I guess to your point of being stupid. Okay, I’m going to take this list here. I’m going to ask this person, again, x comma s. There was absolutely no value that I derived from it. I don’t think they got a lot of value either because I wasn’t as warm and friendly as normally.


Andy Paul  20:44  

Well, it certainly wasn’t a conversation.


Bridget Gleason  20:47  

Joe was in a conversation about there right there. interrogation. All that was missing was a bright light shining in my face, and like being in a dark cell.


Andy Paul  20:59  

So why don’t people still do that? I mean, it’s not like we haven’t talked about this as an industry as a profession and sales for decades. Why is this behavior still persist? I mean, I’m going to presume that all people on the other end of the call have been exposed at some point or another, to a book or piece of training something, a webinar or something that’s seen, that’s a you gotta be smart about how you handle these calls. These are conversations, not interrogations. But you know, connecting and engaging the interests of the buyer. And yet, the situation you described is not unusual. And we’re here now, we experienced that many forums. I get it, either in sales calls, like you talked about, or, you know, when people approach me on LinkedIn, I mean, again, there’s been no shortage of of books and resources written about how to try to use LinkedIn effectively. And maybe 5% of the interactions.


Bridget Gleason  22:26  

I’ll ignore the LinkedIn one right now and just talk about the combo of conversation versus interrogation. People don’t know how to do it. You know, they’re told look at your eyes getting really large like a bow, you know? Yeah. How could they not know how to do it? They don’t know how to do it. When you tell them well, don’t interrogate here a sales manager will say these are the questions that I need answered because you know, a lot is automated, we’ve got templates to fill out. And here’s what you need to know, this will be helpful, you’ve got little script. It takes a lot of practice. And I don’t always know think they know what that means. And they need to have it modeled. You need to hear someone do it. To be able to see the difference between asking a list of questions and getting those same questions answered, but in a way that doesn’t feel like you’re being interrogated. I think it’s training. 


Andy Paul  23:35  

Well, it isn’t some but also the pressure. I gotta get a certain number of dials a certain number of conversations, you know, that that they’re feeling pressured by some of the metrics perhaps so they, you know, the first victim of that is quality.


Bridget Gleason  23:56  

I would say that’s true. There’s much more of a velocity to get a whole bunch in and I don’t think that works so well.


Andy Paul  24:12  

It’s funny that again, sort of the root of my earlier questions, we still struggle with some of these basics. And you know, you wonder, okay, why are we still struggling? After 120 years of professional selling in the United States. I can go back and look at Neil Dale Carnegie from 1936 and say we still have the same problems. Yeah, we haven’t learned a thing.


Bridget Gleason  24:37  

I know they’re going to be studying this philosophy. That’s it that you know what, you can have a podcast just called, Why don’t we learn anything? It’s not just in the sales realm. It’s not limited to salespeople.


Andy Paul  25:02  

It’s not? Absolutely, because I’ve been thinking about this a lot in the US, we have this pressure to do more, right? But doing more by itself doesn’t get you anything, right? Unless you want to turn sales, don’t go to a game of chance, right? It’s like, we’re just playing the outs at that point. If we do enough of something, we’ll get X amount coming out of it. Right seems to be the way so many people are going but the better way is say, well, man, this again, doesn’t apply to sales if you want to do more of a certain thing.


Bridget Gleason  25:36  

The first thing you need to learn is how to do that thing better. And then you can do more of it better. Andy, I am sure in one of the hundred plus episodes that we have recorded. We’ve talked about this, and to an earlier comment that you made about sales enablement, salespeople don’t get the same training that you and I got in the dark ages. They don’t get the same training, we were privileged to have weeks and weeks of training. And I was not allowed to make a sales call until I had completed two weeks. There were certain criteria before they would even let me have an interaction with the customer. Today, it’s like alright, week one be on the phones by Friday for BDR. And it’s a hallmark of success if they can be on the phone by Friday.


Bridget Gleason  26:55  

So I think they don’t get they don’t get the same amount of training.


Andy Paul  27:00  

Yeah, for sure. I mean, companies have varying levels of attention to onboarding and training and so on. Absolutely. But then we just perpetuating the problems that we’ve had. That’s why but let’s go back to the topic, why we don’t learn anything. Like, how come? I don’t feel like we do enough training at tide lift, right? No, I have new people. In fact, it’s one of the things I actually wrote down this morning about something that we need to invest more in right now is professional development for the team.


Andy Paul  27:58  

So what’s the trade off? I think calculation that many people haven’t done is, yeah, we extend onboarding x period of time. Give people more training or to give people an opportunity to ramp up in a way that that when they start finally making calls that are a little more effective, or alternatively, and I see a very small trend of companies hiring more experienced SDRs. I mean, that’s the alternative, right? Just hire somebody with 5/10 years experience. 


Bridget Gleason  28:44  

I don’t know where you find those people that have 5 to 10 years of experience as an SDR. Typically, they’ll be in the SDR role for five months and they’re ready to go to a sales role. It’s hard to find experienced SDRs that want to stay in the role any length of time; it’s not impossible. 


Andy Paul  29:06  

How do we pay them, to compensate and the roles we give them, right? I mean, if you’re looking at like saying a complex enterprise selling complex enterprise product, and you’re basically on a team and with an SDR X number of eight years with an SDR to capture these big accounts, why wouldn’t you pay the SDR the same amount that you would pay the AE’s.


Bridget Gleason  29:35  

That is a topic it could take an entire hour. I’ll tell you what we’re doing at tide lift. We have implemented this team with the selling model that is an enterprise seller, a more sort of middle market seller and a BDR. And the three of them have different functions within. They’ve got a number of target accounts. We sell a lot to very large enterprises and institutions, regulated industries. They’ve got target accounts, they’ve got some geography that they work. And they work as a team and part of their comp plan. They’re all comped on the total number, on the total quota. So they don’t all get paid the same. I mean, they’ve got really varying levels of experience. But it’s a way for them to learn a lot more quickly. Because they’re exposed to a lot more and I think it makes all the roles more interesting. So a BDR is more likely to stay in a role for longer because there’s not just $50 a day, right? Doing this some research, right? 


Andy Paul  31:05  

In that environment, if you were to pay the SDR roughly equivalent to what he gets paid, you could find yourself 5/10 years down the road as somebody who’s really good at that senior level. Think of the first initial conversations they’re having. Yeah, why wouldn’t you pay them that much money?


Bridget Gleason  31:24  

So I would say we don’t call them BDR’s anymore when they get to that next level, but sort of the mid level account executive that I described. At least one of them that we have, is a very recent BDR. So he does tons of the outbound but he gets to sell. The most senior do some outbound prospecting and cold calling also, everybody does. Everyone shares in that so while it’s not three people all getting paid the same amount. Which I’ll tell you I would love to have a sales team that’s not even commission based. Just they work and they do the job.


Andy Paul  32:28  

Well, to the point if you’ve got this team and you’re probably paying the AE most. The AE, he or she couldn’t get that job done without the roles, the contribution of the other two people. So how do you establish a relative value other than by tradition that says yeah, AE’s get paid more?


Bridget Gleason  32:50  

I don’t think it’s tradition. I think there is the, you see the skills that they’re able to bring to the table. And based on a different experience. They’re able to add a lot more than the most junior people.


Andy Paul  33:25  

Sure, but we’re talking about a case where maybe you have a senior prospector, who’s, that’s all they do. That’s all they’ve done their whole career. They’ve got skills like a business acumen, they can be on those initial contacts and source conversations, high value conversations. They can actually qualify a prospect. Yeah, this is I think what we want to get to, right instead of using the SDR and BDR role. Just sort of this, you know, cannon fodder that we throw out for entry level jobs as we turn these into a career. If that value is demonstrated by the fact that you know, your accounting or enterprise account sellers have some skills that are unique. But by the same token, they wouldn’t be where they are. If they had to go back and do all the prospecting that Senior SDR does, they wouldn’t be as capable as that person generating new leads and so on for them. And we need to look at these career paths as being roughly equivalent. And then we start avoiding some of these issues like that call you had, if you’d had a really senior experienced person leading the call, that you’re on the receiving end of might have been a very different experience.


Bridget Gleason  34:41  

So I agree, I think part of it is the number of the effort that’s required to get to one call. Part of it, just looking at the economics of that, there’s still something to be said for this specialization of roles. And yeah, I’m saying make it more specialized just raise the comp to an enterprise AE comp.


Andy Paul  35:24  

Keep people in that role that are good at it. They want to keep doing it. I think there are people that are good at it naturally, that want to keep doing it. And we foreclose that option.


Bridget Gleason  35:36  

We saw that more actually was when I was at Logs IO and we had our team in Israel. And in Israel. There were professional BDR’s Hmm, that was that was a career. Not everybody. Some of them wanted to move into sales roles. So we saw it. They were typically paid better. Not necessarily the same as an AE role.


Andy Paul  36:09  

I was just speaking in sort of extremes but like certainly, with it could be valued as professionals.


Bridget Gleason  36:17  

And they were definitely valued as professionals. 


Andy Paul  36:19  

In which I think we don’t see enough of a specialized thing. We’ve got these SDR, BDR’s. But really the intent is we don’t expect them to stay in these jobs very long. We treat them somewhat badly. It’s well know if it’s really specialized are people really good at it? Let’s reward it and encourage them as a career perspective, like it is a real specialized role.


Bridget Gleason  36:51  

So I don’t think we treat our BDR’s badly. Maybe we should talk to them to see. Maybe that’s my view.


Andy Paul  36:58  

Go to Glassdoor and find out.


Bridget Gleason  37:00  

Yeah, good idea. I think part of it though, is by having them in these pods. I mean, they’re really celebrated at our company. We don’t have that professional sort of categorization and I think they would feel it’s career limiting. You know that if they don’t go to the next level. So I think that will take a movement. So maybe, okay, there’s another I don’t know why I’m finding jobs and things for you to evangelize. But I figure you’re the one with the microphone. So I think that would be interesting to have professional BDR’s that get paid. I like consider in another lifetime. Like it promoting that evangelize.


Andy Paul  38:08  

All right, I added to the list. So here’s a question for you. Who really taught you how to sell? So I think there’s four ways you learn how to sell. You learn to take what you learned through your customers will say we’ll say three. You learn from your customers. You learn from peers, you learn from your managers, or mentors. And, yeah, books and reading and so on. That could be the fourth path to self education, but you have to apply it to your customers and so on. But I mean, I, I looked back and there were several customers I dealt with, like my first 5 years of my career. Customers are really like CEOs of these companies. They took me under their wing and taught me lessons that I remember to this day that influenced how I sell or mentors, managers, similarly, that influenced me. And you said we had great training but quite frankly, when I would go back and look at some of the training that we got they relied heavily on this video based training. 


Bridget Gleason  40:12  

I learned a lot from the training we had. I love school. My sister and I, before we went to school, played school. I wanted to be at the top of the class. For me, the sort of instructor and somebody that has a lot of knowledge and the thing that they did. Well, there’s a lot that’s self directed. I am very used to bringing in as people to do the training the top reps in the field had to come in and do a rotation they got paid the same as if they were 100% of quota. I remember going to this two week training in Lowell Massachusetts. And Bernie was their top Rep. And I think I wrote down every word like I watched how he did it. I watched how he moved, I learned so much so that was sort of a peer.


Bridget Gleason  41:41  

Sort of peer but instructor as well. But certainly my customers probably more than any just this feedback.


Andy Paul  41:57  

Mad customers, giving stories. To this retail chain in the Bay Area, this was selling a computer system and, and the CEO and I had a great relationship, but he just wasn’t giving me the order. And, and finally, he just sort of took me aside and he you’re not thinking this through at this point, you’re just acting surely on the emotion you want to get the deal. And he sort of points out here and says, Yeah, this is great, but this is one point in my head. Now, this is what you’re gonna be using. And I was right, I’d sort of forgotten some of the basics, you know, wasn’t cultivating the relationship the same way is all about getting the order right. And he deliberately held it back. And it drove me crazy. Because I knew I was gonna get it. But it was just teaching me a lesson. And it’s an incredibly valuable lesson about, you know, when you get into these situations, you can’t forget that you have to still work on the relationship yourself to work on the connection you have. Work on continuing to discover and ask questions and make sure you understand that never sort of just focus so much on getting the deal.


Bridget Gleason  43:28  

That was a real kindness. That was a gift. There was a desktop. Yeah. Good time to explain the lesson.


Andy Paul  43:58  

Everything starts after that connection. If you don’t have that connection, you’re not gonna be able to learn the lessons.


Bridget Gleason  44:07  

Andy, it really goes back to that people can we still sell last I checked to humans, as long as we’re selling human to human. That connection in the people is really important. It can’t be all of it like your customer taught you. You’ve also got to use the cabeza. But we’re still selling to humans. So just having that rapport and the connection and being genuinely interested, that they have a good outcome that you’re doing right by the customer. I think that’s probably the most important thing that they know that you want to do right by them for them. Whether it involves you or not, you know whether it involves you getting a deal or not I think one of the greatest lessons I learned and this was Xerox, luckily they really held this as part of their value system. We weren’t looking to get deals, we were looking to get customers. And sometimes you may not get a deal. But by acting with integrity, in that you end up winning a customer and kind of prove itself out in my career over and over. 


Andy Paul  45:30  

Those are the instances where perhaps you’re not the right fit. And you back away from do you tell a customer Hey, I think we’re not the right fit for you at this point in time. And, yeah, I’ve done that. And I’m more than one occasion that came back to me. Later, either the customer went to another company or later at that company’s history. It became the right time to do business. We all represent our character, and people are buyers’ sense. First thing they sense about us is our character. That’s what their perception of us is initially who we are as a person. And yeah, if we don’t operate with integrity if we aren’t considered trustworthy.


Bridget Gleason  46:36  

Yeah, things don’t go very far.


Andy Paul  46:42  

Well, Bridget, I know you have to head off to a meeting here shortly. It’s been a pleasure to talk to you and we can do this again before too long. Until the next time.