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The Habits and Skills that Accelerate Your Success w/ Bridget Gleason [Episode 309]

On this week’s episode, Bridget and I discuss, among other topics, the priority of habits before skills; time management habits and skills; and the superiority of sales conversations over scripted presentations.

Welcome to another Front Line Friday with my remarkable guest, Bridget Gleason. Join Bridget and me for this episode of Accelerate! to learn some foundational sales habits upon which productive sales skills can be built.


Andy introduces the topic — Sales Habits — and suggests that learning skills, without basic habits, is ineffective.

Bridget offers the first habit — organizing your calendar into blocks of planned activities.

Andy asks for ideas on how sales reps can improve their ability to engage with prospects.

An exercise you practice to learn how to lead with questions.

Why practicing skills and habits is an iterative process. It’s not a ‘set and forget,’ but a learning process to revisit and work on constantly, if you want to remain relevant and effective.

Andy and Bridget discuss the pitfalls of scripted questioning, and how opportunities may be lost by presenting, rather than engaging in conversation.

Why sales reps need to provide something of value, in every conversation with contacts and prospects, to help move them closer to making a decision.

Bridget recommends reading A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas, by Warren Berger, for learning questions to ask to extend the conversation.

Andy mentions learning keystone habits, such as responsiveness, from The Power of Habit, by Charles Duhigg.

Andy guarantees that if you commit yourself to being absolutely and completely responsive to your prospects and your customers at all times, you will find your level of success will go up.

Episode Transcript:

Andy Paul 0:56

It’s time to accelerate! Hi, I’m your host, Andy Paul. Join me as I host conversations with the leading experts in sales, marketing sales automation, sales process, leadership, management, training, coaching, any resource that I believe to help you accelerate the growth of your sales, your business and most importantly, you. 


Hello and welcome to Accelerate. And this is another episode of Frontline Friday with my very special guest, Bridget Gleason. Bridget, how are you today?


Bridget Gleason 1:28

Andy, I am doing great, and you?


Andy Paul 1:31

Good, good. Very well, as a matter of fact. Yeah, actually we’re recording this from the island of Kawaii. Or I am on the island of Kawaii.


Bridget Gleason 1:44

Wah, wah, wah, wah, wah.


Andy Paul 1:46

Yeah, I know, right?


Bridget Gleason

It’s a hard life you’ve got. It’s a hard life. 


Andy Paul 

Life is rough today. Yes, it is–  I have to admit, it is raining here which was great this morning when I went out for my run. I love running in the rain. So got that one checked off my list on this trip. But yeah, it’s not bad. How about you? Where are you today?


Bridget Gleason 2:06

I am in Bridget Gleason headquarters in Redwood City, my usual. I don’t move around as much as you do, Andy. I don’t move around as much. I’m boring.


Andy Paul 2:17

That’s not entirely true. We just got through talking about two trips you just took, that both were out of the country, so.


Bridget Gleason 2:21

But I don’t do my travel like–  I don’t do my recording like you do all over the place. 


Andy Paul 2:29

Okay, yeah, you’re always at World Headquarters. So I thought today we would talk about sales habits. Because, you know, it’s just been one of these topics that keeps coming up and up when I talk with more and more executives and sales professionals and so on. It’s one of those proponents of focus on, gosh, we want to train our sales team on skills and so on and so forth. 


But if you look at a pyramid of things that you need to master to really become successful at sales, at the bottom is our behaviors, fundamental behaviors and habits that you have to master. And you can have some skills, it’s just really almost irrelevant if you can master some skills if you don’t have some of these fundamental habits and behaviors perfected as well. So I thought it’d be something good to talk about today.


Bridget Gleason 3:23

Excellent. I love it.


Andy Paul 3:25

So in your mind, what are one or two of the most important sales habits that– well, I’ll say sales professionals broadly. Whether you’re a sales rep, an SDR, account exec, or whatever, what ones would you say are important that you look for, that you want to make sure that your people work for you have mastered, have locked down tight?


Bridget Gleason 3:49

Well, I look at things, I see habit and discipline as being sort of joined at the hip. So I look for good habits as I look for good discipline. So for example, a good habit would be blocking your calendar and being really organized with how you spend your time. And the great sales reps that I’ve known and worked with have made it a habit. At the beginning of the day, they look at their calendars. And they run their calendars, they don’t let their calendars run them. 


So they’re the ones that they may have meetings sprinkled throughout the day. But they’ve blocked out time where they’re perhaps cold calling where they’re following up on opportunities, where they are doing research, where they are in meetings, whatever it is. But they run their calendars as opposed to letting their calendars run them. And so it’s having good time management and really turning that into a series of habits if that makes sense.



Andy Paul 5:06

Yeah, it’s interesting. I just heard a little ding right there, too, to emphasize that. I like that.


Bridget Gleason 5:10

Oh, I know, those special dings that I put in.



Andy Paul 5:14

Yeah, I love the way you edit those in. So yeah, well, I mean, there’s a couple different points there. One is, is a discipline the same as a habit, which we can certainly come back to. But specifically the point you’re talking about is managing time as opposed to having time manage you or managing your calendar. I think that’s absolutely essential. 


You know, I think that whether you’re doing it at the end of a business day for the next day or you do it first thing in the morning is–  If you don’t have time set aside for specific tasks, they don’t happen. We’re all too busy. At any level of an organization, there’s always more demands on our time than we have time available to fulfill them.


Bridget Gleason 5:58



Andy Paul 5:59

And so if you’re not specifically blocking out the time, prospecting is a great activity, especially if you’re a sales rep and that’s your job. It could be for follow ups. It could be for spending time with existing customers in terms of maintaining your connection with them and taking the next steps with them. Yeah, it’s gotta be on the calendar. I do that for myself in terms of–  because we record this podcast and I put up six new episodes a week. I’m writing a new book. I’ve got all these things that I’m doing, working with clients. If I’m not blocking out I’ve flunk, I’ve lost.


Bridget Gleason 6:46

What else do you hear, Andy? I mean, you interact with a lot of different companies and people and coaches. and what do they talk about as the habits that they look for?


Andy Paul 6:57

Well, I think one of the key areas, just broadly, that’s not a habit, but it’s an area of concern has to do with – and we’ve touched on this before – has to do with how do we improve our ability to engage with our prospects? And, you know, really engage with them, have meaningful sales conversations with them. And I think there’s several things that sort of fall into a habit category that play into that. 


And one of them is, I call it ask don’t tell. When you first meet the prospect, don’t fall into giving your pitch. But ask questions. Show your level of interest in them first. Now, this is actually a nice behavior to have in general, both in your personal life and in business life, when you meet somebody new to demonstrate interest in them as opposed to making it all about yourself if you want to make that connection. And so this is one that to me is a habit. 


If you get into the habit of leading with questions, demonstrating interest in the other person, you’re gonna go farther in life, you’re gonna go farther in your sales career. And this is a habit that you have to acquire. Acquire you can call it discipline, but acquire through practice the habit of doing this.


 I remember a conversation I had with Mark Roberge, formerly of HubSpot, who talked about an exercise he does when he meets new people. Not taking it to annoying extremes, but when he meets somebody new to see how many questions he can ask of the other person before he has to say something about himself.


Bridget Gleason 8:34

God, that’s a great test. That’s a great test. I love that.


Andy Paul 8:40

Yeah. So if you think about, you know, you go to a wedding, go to some social event where you’re gonna be meeting new people outside of the business context. There’s all these opportunities to practice this. And so it becomes, like I said, it becomes a habit to practice both on the personal and on the business side. 


But the impact for a potential buyer that you’re meeting with the first time is–  I think they all sort of brace themselves when they first meet a new rep is it’s like, oy,  I’m gonna get the pitch, right? It’s sort of like the pain I have to go through in order to get to the substance of what we want to talk about. But geez, what if you surprised them by getting to the substance more quickly by talking about them, asking about them?


Bridget Gleason 9:24

And I like that Andy, to be considered. This is something that we think about as a habit, which is also a skill. But also think about it as a habit, something that we do regularly.


Andy Paul 9:38

Yeah, well, I look at the skill as a different level, right? If I get into the habit of leading with questions, I’m gonna develop the skill of asking better questions by practicing this habit, right? Through experience I’m gonna learn through the feedback I get from the prospects or people in my life better questions to ask. And so I think you need to have the habit before you can acquire the skill. 


And I think this is actually where sales training oftentimes goes off the tracks for so many companies. It comes in and says, look, we’re gonna teach you how to ask better questions. And it’s like, okay, that’s our sales training. But they don’t even have the habit yet of asking, leading with questions, the people they’re training. And so there’s, in my mind, a huge misalignment there. And so to me, I want to focus on let’s build the habits first. Then you can master the habits, and they turn into skills.


Bridget Gleason 10:39

Yeah, I would challenge that a little bit in that there’s also a school of thought which is, you don’t want to have bad habits. And if you don’t have the skill developed, you may develop a bad habit because you don’t have the skill. So in some ways, I’d rather get the skill and start to develop the skill. And when that’s perfected, turn that skill into a habit.


Andy Paul 11:10

Yeah, I mean, I think it’s a matter of perspective, right? Repetition of a skill to master a skill requires repetition, right? And you get the repetition by turning that into a habit. And so that’s why I think it’s sort of one before the other. And this is where, again, I think that oftentimes we do a disservice with sales reps. 


We don’t do enough to work with them to say, okay, here are some really core habits. If you can integrate this habit into your day to day of work, into your day to day process, then wow, the ripple effect throughout the rest of your selling is pretty substantial. Because as you continue to master it and ask better and better questions, then wow, you just become more and more effective.


Bridget Gleason 11:58

Yeah, I agree. Like you said, it could be a little bit cart before the horse. And I guess the two– it’s an iterative process, skill and habit, skill and habit. It’s never a set and forget. So I think skill building and even looking at habits, it’s not a set and forget. It’s something that we constantly need to revisit and work on if we’re going to remain relevant and effective.


Andy Paul 12:27

Yeah, no, I agree. I mean, I think we’re sort of talking somewhat about the same thing, which is in terms of me and my experience, and when I’ve worked with sales reps, it’s like, yeah, let’s get this building block in place first, right? The same thing is, gosh, another one that I love as a habit is once you’ve asked your questions, one of the habits I get people to train on is to lead with questions. Then the next habit is to have to learn how to listen to the answers.


Bridget Gleason 13:05

And why do people have such a hard time with that?


Andy Paul 13:08

I think that that part of it is that, and this is not new by any stretch of imagination, is as sales professionals, we tend to be a little scripted in how we approach, right? We know the five questions we need to ask. And so when we ask the first question, then we’re already looking for what the next question is, right? We’re thinking about what the next thing we’re going to say is. And we’re not really listening to what the client has said.


I’ll give you a perfect example as I was just listening to some recorded call. It was a SDR and account exec. It was actually a handoff. The SDR started it, handed it off to the account exec. And in both instances, and these are experienced SDR and experienced AE, is they’d ask question of the customer. The customer would answer it. And there would be this silence. They’d say yes, and they clearly then would step to ask the next question that was on their list as opposed to asking a question in response to what the customer said. 


And that’s a huge missed opportunity, right? To broaden and deepen the engagement, to maybe start differentiating yourself from all the other sales reps that are talking to that potential buyer that are just lockstep following their script. And when I hear this time and time again when I either attend calls or I’m listening to calls like I was with these is just they’re not really paying attention to the answer. They might be writing some notes down. 


But then instead of having the habit of saying, yeah, I want to ask a follow up to that, I’m sort of listening without judgment I call that, right? I’m eliminating my filters. What’s the next great question to ask? Now we just go to question number two on our list. And to me that’s a bad habit that you need to change.


Bridget Gleason 15:11

Yeah, and it reminds me of sort of a pet peeve of mine, which is people forget that sales is a conversation. It’s not a presentation. And in order to have a conversation, a conversation requires active listening. It’s a building on what’s happening. When it’s a presentation, it’s just, okay, I need to say this, and I need to say this, or I need to ask this. 


And so to your point, Andy, about being too scripted, it’s a conversation. And if it’s a conversation, it’s about exploration. It’s about asking, it’s about learning. It’s about inquiring, it’s about listening. And it’s really trying to get a deeper understanding. 


And I think you’re right that too often sales people mistake what they’re doing, and it looks a lot more like a presentation. You have the other person there and you ask a few things. But really, all you’re trying to do is say things. And you only want to push things out as opposed to things coming back in. And that’s not very effective.


Andy Paul 16:17

No, no. And yeah, as I said before, you miss opportunities to deepen the engagement. 


Bridget Gleason

So much.


Andy Paul

Because in this one call, the SDR asked a question about, without revealing who the vendor was, how many of this certain thing do you need, right? Like how many seats do you need, let’s say, for this software service they’re selling. And the buyer gives an answer. And he never comes back and says, well, okay, why do you need that many? Where are they gonna go? Who’s gonna use it, right? What’s the profile? What is the application? 


None of that. Just went to the next question. And it’s just like, oh, that was such a missed opportunity. So that’s one.


Bridget Gleason 17:04

And Andy, when that happens to me, when I’m on the receiving end of that, I have to tell you, I feel hostile. Like I don’t like it. I feel so–  offended is not the right word. Really, hostile is the right word. I’m not proud that I feel hostile, but I do. I feel not valued when it’s just this they’re not really listening. It’s not a good use of my time. And I don’t  take it very well.


Andy Paul 17:38

Yeah, well I think it reflects badly on multiple levels. I think part of the perspective on the part of the buyer is, oh, okay, so we’re just gonna be sort of superficial here as you start talking. We’re just gonna be sort of super superficial. Well, they’re sort of projecting that out into the future, right? How’s that gonna play out in our long term relationship? Are you always gonna have sort of a superficial level of interest? Like if I have a problem, if I buy from you and I have a problem, are you really gonna dig into it. Or are we just gonna do what’s most expeditious?


Bridget Gleason 18:10

Yeah, and I and I think it’s too bad when a sales rep presents him or herself that way. Because then the company, by default, is also perceived that way. And so as you said, if you’re not digging into my problem, then I’m going to carry that and extend that feeling about the whole company. 


You may have other parts of the company that are excellent at caring for the customer once they become a customer. But if the sales rep is presenting something different, that’s what’s going to be carried forward in the mind of the prospect. That, oh, they’re not going to dig in. They’re not going to listen. If I really have an issue, this is how it’s gonna get handled. 


So the sales rep can do a huge disservice at the early stages of misrepresenting where other parts of the organization may actually be quite different and quite customer oriented. But if the sales rep is not demonstrating that early, there’s no way for a prospect to get that sense.


Andy Paul 19:18

Well, okay. So I mean, sort of along the same lines, to me another key habit is for sales reps to consciously, deliberately say, every time I’m going to interact with a potential prospect or potential buyer that I’m gonna have something of value I’m gonna provide them during that interaction. There’s something that’s gonna help them that I’m gonna provide them that’s gonna help them move closer to making a decision. Otherwise, why am I consuming their time?


Bridget Gleason 19:53

I couldn’t agree more violently than I am agreeing in my head. Yes, yes! Time! We can never get time back.


Andy Paul 20:05

And this, to me, this is a habit.


Bridget Gleason 20:08

It is a habit. It’s a habit and it’s a courtesy. You need to be able to provide something of value. You need to bring something to the table. Otherwise– 


Andy Paul 20:22

You’re not respecting their time.


Bridget Gleason 20:24

That’s right. 


Andy Paul 20:26

Yeah, and as you said, it is a courtesy. It’s very obvious to customers if you’re not respecting their time.


Bridget Gleason 20:35

That’s right.


Andy Paul  20:36

Much like leading with a pitch. So I think another one, we sort of talked about questions, another yes or follow up to that to me is a great habit to have. And it’s not like you need to have all of these habits. But ideally it’d be great, but not everybody does. Ask the extra question. And you know, several people have written some good stuff about this.So I wish I could claim credit for it, but I can’t. 


But it’s, you asked a good question to the customer, they give you a response. And then, and we’ve talked about this before, then you say, okay, well that was interesting. So what else can you tell me about that? Or, hm, interesting, tell me more. It’s that being able to extend yourself that one step to ask that extra question, especially that one like, tell me more or what else can you tell me about that. That, again, immediately deepens engagement with the customer. They’re gonna take you to places where they’re not necessarily going with your competitors.


Bridget Gleason  21:48

It’s interesting that you’re bringing this up. I read this great book, I’m actually in the middle of it, The Most Beautiful Question. And it’s all about the importance of questions. 


Andy Paul

Interesting. That’s the name of the book? 


Bridget Gleason 

Yeah, The Most Beautiful or The More Beautiful Question. And it’s all about asking how to keep moving forward in business, in your career, it’s not about having the answer. But it’s about knowing the questions to ask, and extending the conversation, and thinking about things differently. It’s a really provocative, very interesting book.


Andy Paul 22:36


Okay, so it sounds like a book people should– 


Bridget Gleason 22:39

A More Beautiful Question by Warren Berger. 


Andy Paul

Warren Berger, okay. A More Beautiful Question. All right. So there we have a recommendation. We got Frontline Friday. We have to have a book recommendation.


Bridget Gleason 22:52

I know. I’ve always got recommendations. I know. I always have them, don’t I?


Andy Paul 22:56

Oh, that’s a good one. I like that one. That’s going on my list.


Bridget Gleason 23:00

It should go on the list. It’s a good book.


Andy Paul 23:01

Excellent. And it’s a relatively recent book, too.


Bridget Gleason 23:03



Andy Paul 23:04

All right. Very good. Any other habits on your front that you think are important people should master?


Bridget Gleason 23:10

I think those are good ones to start with. I think those are pretty basic. And, you know, I find that typically if we just pick one or two things, we’re more likely to dig in and be able to do them than if we pick a whole bunch of things. And I think those are basic, very important ones.


Andy Paul 23:29

Well, you bring up a key point, which is, and this is a topic that I plan that we’ll discuss more and more in the upcoming months, is that yeah, there’s no shortage of things you can do within your daily routine, these habits and disciplines that perhaps could help you improve. 


But to your point is, yeah, there’s no shortage of them. You can’t can’t master all of them. You can’t incorporate all of them into your routine. So it’s really important to pick some number, start small, the ones that will have the biggest ripple effect throughout everything you do.


Bridget Gleason 24:06

Right, pick one.


Andy Paul 24:07

Yeah, yeah. Well, you’ve got to start somewhere. So start with one. But yeah, big believer, if anybody’s read the book called The Power of Habit by Charles Duhigg, It talks about what’s called keystone habits. These are the habits, could be one habit, that does have the sort of pebble in the pond effect where you get the ripples that has an impact on everything you do. 


And you know, one of my favorite ones, favorite habits is responsiveness. This is one, to me, that if I was gonna choose one – we didn’t have a chance to talk about it today – but that’s one that if you commit yourself to being absolutely and completely responsive to your prospects and your customers at all times, you’re gonna find your level of success will go up. I guarantee you, your level of success is going to go up.


Bridget Gleason 24:57

Yeah, that’s a great one.


Andy Paul 25:00

Okay. Well, Bridget, we’ve come to the end of this particular show. I want to thank you for joining me. I want to thank our friends who have joined us listening to us today. I really appreciate you taking some time out of your day to spend with us as we talk about habits today, but sales in general. So thank you very much. And Bridget, I look forward to talking to you next time.


Bridget Gleason

And likewise.


Andy Paul 25:20

Alright, bye now. 


Thanks for listening to the show. If you like what you heard and want to make sure you don’t miss any upcoming episodes, please subscribe to this podcast on iTunes or Stitcher.com. For more information about today’s guest, visit my website at andypaul.com.