How SDRs and AEs Should Prepare for an Uncertain Career Future, with Bridget Gleason [Episode 790]

Today, my friend and erstwhile co-host, Bridget Gleason (Head of Sales, TideLift) joins me on Sales Enablement Podcast #790 to talk about what SDRs and AEs should be doing NOW to prepare themselves for an uncertain career future, and how to improve onboarding new sellers and upskilling more veteran sellers.

Episode Transcript

Andy Paul: Bridget. Welcome back to the show.

Bridget Gleason: Andy, Andy. Great to be back.

Andy Paul: Yeah. So I have, I’ve lost track of how many episodes this says that you’ve joined me on over a hundred. So,

Bridget Gleason: I know it makes me feel old.

Andy Paul: It makes you feel old.

Bridget Gleason: Oh, so many, so many old, but honored, honored, but old

Andy Paul: Well, it’s nice to be old and honored

Bridget Gleason: that’s true.

Andy Paul: respect for your elders.

Bridget Gleason: That’s right.

Andy Paul: have respect for my elders.

Bridget Gleason: That’s right. I like it.

Andy Paul: So what’s new in your world with everybody working remotely. And, um, first of all, how’s that? How’s that going? I mean, everybody staying healthy, sane.

Bridget Gleason: well, we tied Lyft. We’ve been a remote company, so working remotely isn’t new to us. So that part isn’t new. But having a lot of our customers and prospects remote has obviously disrupted things as for everybody. I would say, though, so far everybody’s healthy spirits are good. You know, it starts to take a toll, but I think all in all, you know, we’re, we’re taking it day to time and I think healthy spirits.

Good. Starting to look like spring here in Boston. So that’s nice. We can get outside. Even with face masks, we can get outside.

Andy Paul: No, I forgot if I asked you before, are you running with your mask on.

Bridget Gleason: I am running, I don’t have my mask on. I wear a, like a, a neck Gator that can be pulled up. So if I, I go early and I don’t usually see anybody. Um, but if I see somebody, I can always pull it up, but I’m not running. I’m not running with a mask on

Andy Paul: Okay. Yeah, I was out a couple of days ago and I hadn’t been running since the shutdown. I’ve been riding my Peloton alone, inside the apartment, but went out and did a short run wearing the mask and it was, it was harder like, uh, you know, running it altitude.

Bridget Gleason: Yeah. It’s harder. It’s harder. It’s just it’s it’s yeah, it’s not very comfortable. But, you know, if I go early enough that I haven’t had to, I haven’t had to worry about it too much.

Andy Paul: Yeah, you’re out four 30 in the morning or five 30 in the morning. Some crazy time like that.

Bridget Gleason: yeah. I’m usually up at four 30 up by five 30.

Andy Paul: Jeez, Louise.

Bridget Gleason: I know. It’s crazy. It’s crazy. You’ve known that nothing’s changed.

Andy Paul: Yeah. I mean, I, I. I don’t mind running early. It’s just, I usually like it to be the light.

Bridget Gleason: Yeah, there’s something about like pitch black isn’t as fun, but there’s something about still a little bit dark and the sun coming up. That just feels good. Like I’ve gotten a jump on the day and it’s still quiet. There’s something about that solitude that I really, really appreciate because the rest of my day isn’t.

Andy Paul: It doesn’t for anybody. I think now it’s I raise wall-to-wall zoom meetings these days.

Bridget Gleason: Oh, I know. I know. I know. And we were, it’s funny, Andy, because we’ve always been remote. But it seems like the, I don’t ha how can I have more zoom meetings? I guess that’s possible because I was able to go in person to certain meetings, which I’m not doing anymore. So that’s that sort of

Andy Paul: how big is your sales team,

Bridget Gleason: got about 15 people total on the team sales team.

Andy Paul: don’t have any one place where you’ve got a concentration of people who are all

Bridget Gleason: Mmm. Yeah, we have, uh, we do have a concentration in Boston, so I had most of the time I was going into a coworking space where we are, uh, everybody doesn’t go there every day, but we have a place where we can go, which is great to get the team or a good number of the team together. But we’re, we’re geographically dispersed as well.

Andy Paul: so question for you from a. Yeah. Management standpoint, coaching standpoint. So on this is, yeah, this whole thing is covert thing is probably gonna disrupt some careers

Bridget Gleason: Hmm.

Andy Paul: I think if you were advising, let’s say someone on a, more of an entry level SDR role right now, what advice would you give them about how to prepare themselves for what comes next?

Bridget Gleason: what do you mean? Like.

Andy Paul: mean, this, the environments were be different. I mean, it’s, it’s, we don’t know what it’s going to be necessarily, but I can project we’re going to have more permanent or may have perhaps more permanent element of work from home work, remote, uh, certainly more virtual stuff. It’s hard to see what’s going to happen relative to field sales.

I know you don’t guys don’t really do as much of that, but, uh, field sales coming back, but. I just wonder, you know, do you think like there’s a different or enhanced a skill set people are gonna need in the long run to be successful in those roles?

Bridget Gleason: Yeah, it’s a really. It’s a really, really good question. And again, because we’ve been remote and we do actually have a field team we’re selling to very large regulated industries. So we do, we do have a field team as well. Um, yeah, I think there’s, the communication is going to need to be different where like we’re going to need to be.

Able to create connection and trust and relationship virtually better than we have before. Okay. So I think, I think that’s, I think that’s one.

Andy Paul: And I, I agree on that by the way, I think that we’re gonna have to use the word communication we’re gonna going to become. I don’t know, more precise maybe is the word in how we communicate. It was really a fascinating article that I read in New York times this week about, or admit the tail end of last week about, um, you know, they’re always doing research on the impact zoom has having on

Bridget Gleason: Hmm.

Andy Paul: of conversations people are having.

And it was interesting cause I was talking about, okay. Yeah. If you’re trying to communicate in a meaningful way. But actually zoom presents some disadvantages compared to being on the phone. Certainly disadvantages that don’t exist when you’re meeting face to face and talking about just the way the signal is processed and it sort of smooth out some facial cues and social cues we might otherwise pick up on in conversations. And that has an impact on how effectively communicate.

Bridget Gleason: Yeah, I read that article. I found that I found that interesting, Andy. I never thought I would feel this way, but there was a day last week when I thought. Let’s just bring back the conference call with no video and everybody on their phones and the Polycomm. Can we play, bring that back? Like I never thought I would want that back, but you’re right.

There’s something about there’s something about zoom is she is, as that article had pointed out that make the cues, they, they distort them somewhat. That I think is difficult. There’s also some things that when I’m in a professional setting, I don’t need to see all of the very personal living situations that people are in.

I don’t know.

Andy Paul: Aren’t you? Aren’t you curious?

Bridget Gleason: I’m not, I want to stay. I want to stay blind and have a beautiful image in my mind. I like the, the blank wall. I like the office setting. I think the zoom backgrounds are a lifesaver. Um, I know. Well, I don’t, but you know what I like least is. Uh, cans and dirty dishes in the background. I’m a neat freak.

So I get distracted, but I get distracted by the backgrounds that this, this says a lot more about me than the other person. We recognize

Andy Paul: you more with the customer? If you’re talking about yours, one of your sales team.

Bridget Gleason: Oh,

Andy Paul: it could be like a coachable moment

Bridget Gleason: Oh, Oh, I’m white. I’m I’m way past you. They’re like, yes, he was. Yes. I’ve already, I’ve already said blank wall or background. Those are your two choices, but we’re not seeing, I don’t want to see family members and dogs in the background. Like let’s, let’s just keep it neutral. Let’s keep it neutral. I know.

It’s terrible. It’s terrible.

Andy Paul: to see a dog. I mean,

Bridget Gleason: What’s that?

Andy Paul: I’m always game to see a dog, but I saw this video that was actually about my friend. I saw on TV last night as someone who’s on a zoom call or FaceTime call of some sort for business. And her husband who could be generously described as overweight. Uh, it comes, comes out wearing a, like a fake grass, skirt, and a, like a, a Samoan head dress and sort of semi hula dancing in the background.

And she served completely unaware of these, doing it for about 10 seconds and he’s shirtless. And I thought that was funny.

Bridget Gleason: That is fantastic. Now for internal calls. I don’t mind like internal calls, pets and dogs and kids and family and backgrounds. I don’t mind at all. Like, I don’t mind it for us internally at all, like that.

Andy Paul: standard was what your reps need to have when they’re talking to the customers.

Bridget Gleason: Right, right, right. Yeah. Yeah. If it’s, if it’s us internal, no, we should be able to, to bring our full selves to the, to the company. I just think when we’re interfacing externally, we’re, we’re sending all kinds of signals that we may not want to be sending. And I don’t know enough Andy, to know what those signals are saying.

So best to just be quiet and not send them blank background. Okay. Cause we don’t know what they’re saying and I don’t have time to go figure it out.

Andy Paul: we could make certain assumptions that if, if you’re calling on a new prospect and you’ve got dirty dishes in the sink behind you that are noticeable, then that they’re suddenly going to pick up on that.

Bridget Gleason: Yeah, well, yes, but I don’t know what that would. I don’t know what message that would send. Do whoever the receiver is like I’m on calls and yeah. You know, we’re, we’re talking to people that are working at big banks and other financial institutions and healthcare get like big companies and okay. I’m sometimes a little surprised at just, okay.

Andy Paul: they’re with the customer.

Bridget Gleason: I know, but that’s what I’m saying. So it’s okay when it comes that way, but I, I guess I’m recognizing my own surprise and I think, okay, but they’re the customer. They can do whatever they want, where the we’re we’re the seller. So we’ve got to be a little bit more careful, Andy, even if I, I mean, most days I have calls with, with customers at some point during the day, but even if, even when I don’t.

Even on the rare days that I don’t, I get dressed every morning as if I’m going to walk into an office. The only thing I don’t do, although I may start is I don’t wear the shoes that I would wear. That’s the only, that’s the only thing

Andy Paul: off. Yeah.

Bridget Gleason: I know, but you know what? I started to miss them as part of the. I don’t know it as part of the routine as part of the, the way that I signal to myself, I am, I’m going to work.

And I go, when I work my day, I only work in one part of my, um, I’m in a condo in Boston, only one part of my apartment. And I only work in that one place. And when I’m done. I put everything away. I changed my clothes and I go into, into a different mode. I even have a different computer that I use for work and that I use for personal.

And so when I’m done close up the work computer and, you know, I can get everything on all my computers, everything cause we are in the digital world, but it’s, it’s it’s signals that because I really, I, for my own sanity. I try not to let work bleed anymore, like, than it has, like give it, give it its space.

And then

Andy Paul: Yeah. Well, the boundaries have definitely been blurred

Bridget Gleason: yeah. And we were remote before. That’s what sort of that’s, what’s sort of interesting. Um, but it’s just when the rest of the world is blurred as well. It’s it’s created sort of a different experience. I would say.

Andy Paul: so are you finding a connection rates with, on calls different than before? You know, during normal times now they’re different now than they were before.

Bridget Gleason: I, you know, I should have our, my BDR manager look into that because I think the answer actually, I think the answer is yes. But I’m not sure because, um, we still get a lot of communication that happens Sunday night. And I think that’s always been the case. Hmm. But, and, and we’re not calling people on Sunday night, but they’ll respond to a LinkedIn request or an email, or that’s when they’re kind of checking, uh, for the next, for the next day.

Andy Paul: planning the week, right?

Bridget Gleason: Right. So I think that’s always been the case. It may be more maybe less now. I don’t know. I don’t know. It’s a good, no.

Andy Paul: Yeah. We’d had a session last week with, uh, Jeff Shelton. Who’s vice president of product and sort of lead data scientists at ring DNA about this. And yeah, the analysis of our data is that yeah, connection rates are actually up, um, during this period. We’re not exactly sure why yet, but just our aggregate basis and up for all types of titles.

Bridget Gleason: Yeah. And it’s interesting. I wonder, you know, that people are there at their computer and they’re near your phone. They just are there. They’re not in a conference. They’re not out of town. They’re not traveling. They’re not on vacation. They’re not they’re there. They’re not in the meeting. They’re not down the hall.

They’re not at the water cooler.

Andy Paul: Yeah. I mean, the connection rates are sort of interest and they’re sort of, the curves are surf again, we’re making assumptions about causes for a lot of this, but it’s, it’s almost looks like a sort of, um, Track too, like, especially if somebody is at home with kids track to the, uh, school day, you know, the,

Bridget Gleason: right.

Andy Paul: in homeschool day, um, that, yeah, once the kids are got to sit in front of the computer, then people answer their phones more and then sort of two o’clock. Not so much anymore, but it seemed like it shifted earlier. So if parents were taking kids to school and then I came to the office a little bit later, cause they drop kids off at school. And so on, actually we’re still recommending that reps are start their day earlier to catch that earlier wave.

Cause it definitely wasn’t an earlier wave of availability.

Bridget Gleason: yeah. It’s I had forgotten about that influence that school’s being closed. Definitely disrupts. Uh, kind of the working cadence that had been in place.

Andy Paul: Yeah. I mean, can you imagine having done this when your kids were young?

Bridget Gleason: Oh no.

Andy Paul: to sell and manage groups, people and have kids at home and so on.

Bridget Gleason: now and you know what, Andy? I didn’t. As soon as you know, and I I’ve shared my story before, but, um, I was a single mom with my, from the, since they were one in three. So it wasn’t like I was, you know, it was a walk in the park for me. Um, it was, it was tough, but this seems harder. I don’t know why this just seemed, I guess yeah, this seems harder.

Andy Paul: Well, if you’re a single mom. mean, and I mean, teachers are trying their best, but I mean the of reason we send the kids to the classroom, I think it was either get socialized. Also, the teacher has some semblance of control and ability to focus them. But if they’re at home, you can imagine the kids are distracted and the parents are one of the distractions and yeah, it’s gotta be that’s I’m glad we’re past that stage, but it’s, it’s gotta be tough, especially. I said, if you’re working accounts, managing a team, whatever, um, yeah. Fairly are unpredictable. So kudos to those people who are, are making that work.

Bridget Gleason: Well, and I think Andy, just when you had asked earlier about, you know, BDRs SDRs, what’s. Just looking out to the future. What should they like be thinking about? I think at least for the next several years, we have to think about how to better accommodate the human element of selling you. And I’ve talked about it a lot, how important it is.

And I think now it’s even. It’s even more important because we’re all feeling it, EV people are stressed, they’re anxious, they’re worried. They’re, you know, they’ve got PR perhaps kids at home. And so how do you strike this balance of being, um, sort of empathetic. To that and acknowledging that and still continuing to move things forward.

I think it’s a different, it’s a different sort of, it’s a different kind of skill. And I think that the reps that are able to develop that and be sensitive around that, if that is something that will serve them well

Andy Paul: I agree that if you. I was assuming you were going to ask me my opinion on that. And that was number one on my list is never before. I mean, think about it. Has it been so obvious that you actually share a common ground with the people you’re talking with? Right. I mean, we’re also, and we haven’t maybe the 2008 recession, but people aren’t working from home and so on is here’s a shared experience. For basically everybody you’re gonna talk to. And so in terms of establishing that basic connection, as you said, having displaying empathy, well, you, it’s not a matter of putting yourself in their shoes. It’s a matter of singing it. I have empathy because I can, I understand why you feel the way you do cause I’m feeling it myself.

Bridget Gleason: And Andy. Okay. So one of the reason I didn’t reasons I don’t ask you the question, cause you’re used to me asking you the questions, but now, because we’ve done so many of these, I can just answer the question for you. So then I don’t even have to ask you asked and then I can just sorta sit here and have a conversation with myself.

Like me playing me playing. May me playing you, me playing me. Um, I, yeah, that’ll really put everybody to sleep. It’s good. It’s good. Yeah. Bedtime. But your, your point that nuance around that is so God, I, I wish I had said that, that you’re right. It’s we’re always looking for connection. And here in this time, we know we have a common ground.

We have it. They know we have it. We know we have it. And so being able, just to experience, you know, figure out how to experience that is, um, is a skill.

Andy Paul: Yeah, well, don’t be afraid to bring it up. That’s the thing that I was talking to a couple reps, um, individually a couple weeks ago, I was sort of like, wow. Yeah, everybody’s talking about it. It’s sort of been done. It’s like, no, no, no, no, no. Just now is the time. You know, learn, learn how to identify these, these areas of common ground that enable you to connect on this human level. That starts everything right, absent that connection. You’re not going to go anywhere with this buyer. They may talk to you, but they’re not gonna buy from you. Is this is a perfect time to learn the lesson about how we identify those points of commonality that we can use to establish the connection.

Bridget Gleason: Well and important to get used to talking about things that are either uncomfortable or feel awkward. You know, that’s, that’s also a good skill is how do you, how you bring up things that you may feel awkward talking about?

Andy Paul: Yeah, the vulnerability vulnerability, excuse me, as I muddle my words here, but yeah, that whole idea of don’t want things you’re uncomfortable with. Um, Yeah, get comfortable if you can sharing them. Because again, that unlocks so much in terms of the connection you can make with someone it’s a key to unlocking the ability to build trust with someone is that they see that you’re you’re human and they share things with you.

Bridget Gleason: And last I checked Andy, we are still selling to humans, say B2B, but it’s still H to H.

Andy Paul: Well, and I think more so than, than ever to your point you made before, because, and I know we don’t have a ton of time here to get into it, but just sort of raise it as interesting, seeing a statistics, government statistics over the weekend about how, um, economic productivity and how it really peaked in the early two thousands, our growth rate of productivity as an economy. And, and it was a Paul Krugman article, Nobel prize, winning economist, talking about how the, the impact of it tech driven productivity. We started past the peak of that and that, you know, the impact of adding more tech to increased productivity. It’s not showing the benefits. And so it’s fairly stark differences in productivity growth.

Right now we’re about one and a half percent per year. And 15 made the point it’s 15, 20 years ago. People forecasted that, Hey, I was still going to be at three, four or 5% a year because we’re continuing to innovate in tech, but it hasn’t happened. And so if you’re relying on tech in sales to help you take that next step up.

That’s not, what’s probably not. What’s gonna do it for you and what’s going to do for you. It was your ability to be more human and connect and have empathy and vulnerability and build trust. That’s still more powerful than any new tool you can use.

Bridget Gleason: definitely. And it’s, it’s helpful for your internal communications. With other people that you’re going to need other stakeholders or fail, that’s important, gaining consensus and having people help you and just getting the resources you need internally. And then as well as just the interaction with prospects and customers.

Andy Paul: Yeah, well, on another episode, we’ll talk about this idea of, of team that you brought up. Cause it’s so important and we’ve talked about some in the past, but I just want to keep coming back to it because yeah, whatever you accomplish those in sales that you do as a member of a team, and to your point precisely about your ability to build those relationships with people on your side are as important, oftentimes as building with the customers

Bridget Gleason: if you want to go fast, go alone. If you want to go far, go together.

Andy Paul: Oh, perfect.

Bridget Gleason: African proverb.

Andy Paul: Oh good. I like that. I like that.

Bridget Gleason: that’s my little list. That’s that’s my gift to you.

Andy Paul: Thank you. We’ll wrap up with that today. So, um, Bridget, tell people how they can connect with you.

Bridget Gleason: at Bridget Gleason on Twitter and my LinkedIn profile. Bridget Gleason. Very easy.

Andy Paul: Alright, well, Bridget, thank you. As always for joining we’ll look forward to again shortly.

Bridget Gleason: Sounds great. Thanks Andy.

Andy Paul: hello.