Ep 37: Sales Emails, Proposals & Generational Challenges

BuzzSprout Audio

“Create mutual accountability for your customer. Your customer wants something from you. Well, that’s a give. And you should create some sort of get in return.” – Taylor Barnes



Josh Sweeney: Hello, my name is Josh Sweeney, I’m joined by my co-host, Taylor Barnes Taylor. How are you today?

Taylor Barnes: I’m doing great today, I’m doing fantastic, and this is one of these subjects where instead of coming up with a catchy, funny, like punchline right here, I’m ready to get right into: Do Not Email That! Whatever you’re about to send. Wait and let’s talk about it before you email it.

Josh Sweeney: Don’t send it! So, every sales leader has had this challenge where your rep somehow didn’t know when to email and when not to email or in some cases what not to email.

Taylor Barnes: Yeah.

Josh Sweeney: So let’s talk a little bit about why people end up sending things they shouldn’t and then we’ll get into some solutions. So, Taylor, what’s the first reason that people end up sending things that they shouldn’t via email?

Taylor Barnes: Well, I think the natural reason is that it’s just become the easiest thing to do, the easiest form of communication and the rep or the manager or whoever, internally or externally will simply send a note. You remember you remember the old AOL probably aging ourselves here, but the AOL

Josh Sweeney: Yeah.

The New Sales Email

Taylor Barnes: Instant Messenger. Well, I’m sure there’s different chat features and a lot of these, you know, Zoom’s and teams and all that nowadays. But we have evolved email into the new chat, which is absolutely what it was not designed to do. And more importantly, I think it’s because the management team doesn’t really reinforce any difference. And so the salesperson will just simply hit the easy button or the management team or whoever is wanting to communicate will just hit the easy button. You know what I mean?

Josh Sweeney: Oh, Yeah.

Taylor Barnes: The number one reason.

Josh Sweeney: Yeah, it’s easy, it’s quick, it’s comfortable, you know, you could just fire off and forget and come back later. There’s not a lot of effort. And, you know, I know from a culture perspective, we instituted a piece, a culture change that we’re constantly trying to reinforce. But it’s this concept of pick up the phone culture so everything

Taylor Barnes: Like that.

Josh Sweeney: Shouldn’t be emailed. You know, we actually want to reinforce picking up the phone.

Taylor Barnes: Mm Hmm.

Josh Sweeney: So I think, the easy button is why it happens. But there’s a lot of other reasons it happens. You know, another one is generational.

Taylor Barnes: Yeah.

Josh Sweeney: Yeah. So for example, you know, if you just started and generationally, you’re used to email, you weren’t around, you know, when people picked up the phone.

Smiling and Dialing

Josh Sweeney: I was doing a podcast the other day and, somebody who’s had their business for 30 years and they talked about how in the early days of sales, they dialed for dollars. And now if you dial for dollars, you never talk to anybody,

Taylor Barnes: That’s it, Smiling and Dialing.

Josh Sweeney: Yeah, but that’s totally different when it comes to it should be different, at least in somebody you’re engaged with. Right. You’re already having a conversation. You can pick up the phone and use a different option. So I think it’s a generational challenge. What else do you think around, like the generational change and things like that?

Taylor Barnes: Yeah,

Josh Sweeney: Email.

Taylor Barnes: Right, and I think you’re dead on. I mean, there’s you know, we hear regardless if you’re you know, you’re a younger Gen X or a Millennial or whatever the names of the new ones are, I think that we’ve you know, and maybe not we’ve not the age ourselves here, Josh, but maybe some of the some of our younger colleagues have grown up in that, you know, in that electronic world where information is available at their fingertips. And if you want something, it’s right there. If you need an answer to a question, it’s right there. And I guess it just doesn’t take and this is going to sound meaner than I mean it to sound. So whoever is listening out there, this is not personal, but I think a lot a lot of things are easier now in terms of getting information or contacting people or being able to reach out and touch someone. It’s as simple as cooking a couple of buttons. And people have just developed such a kind of natural relation. Well, it’s not a natural relationship. They’ve created such a path to relationships electronically versus getting on the phone and discussing or, you know, traveling out or driving over to someone’s house or whatever it is. And it doesn’t feel impersonal to them. It doesn’t. So why would you change it? It feels plenty personal to them. And and honestly, it’s one of those things, Josh, which kind of cracks me up depending on who the customer is. I mean, we’re the ones getting older. Customers are getting younger, too.

Josh Sweeney: All right.

Taylor Barnes: They might appreciate the communication like that more than they appreciate getting on the phone. So I’ll be the first to tell you that this might be the new way. I don’t know the new way necessarily, but it might be because it’s so common in this generation whether you’re on the sales side or you’re on the customer side or whatever. It just is such a normal way of communicating right now. So it’s so not only is it easy, quick and comfortable, it’s just normal. And the normal is why I think a lot of people don’t necessarily understand when or when not to use it.

Josh Sweeney: Yeah, most definitely, I mean, you just get used to that rhythm and it makes it harder to do something else where, you know, there’s lots of reasons, kind of like what we were talking about, you know, when not to email. I mean, there’s a lot of times when I’ve gone through and seen emails going back and forth and it’s like, hey, you guys just spent, like, all this time emailing back and forth. And you could have picked up the phone and it would have been done in 60 seconds.

Taylor Barnes: Mm hmm.

Josh Sweeney: And I’ve done that myself. I’ve gone back and forth on two or three emails. I’m like, this needs to be resolved and I’ve even done it on slack. Or it’s like this is not a this is not a chat communication. This is not an email communication. This

Taylor Barnes: Exactly.

Josh Sweeney: Is a pick up the phone moment. And I think that’s what we have to realize as leaders, is how do we train people to recognize the pick up the phone moment

Taylor Barnes: Hmm.

Josh Sweeney: Or, you know, switch mediums moments so that they know what to do when and on what medium?

When to Email, When Not to Email

Taylor Barnes: Yeah, and, you know, I mean, the real challenge, as you mentioned, is when to and when not to email, while to play devil’s advocate here, one of the reasons when to email they do is something like audit trails that they need to be able to have an audit trail of the communication. So that’s the reason when to email. So I want to be clear, there are plenty of great reasons to do this. And, you know, one of which is an audit trail, one of which is putting an actual document in a mailbox that people need to go back and reference historical versions of different proposals. You know, how many times do you hear this, Josh, that? Well, they’re asking for a six version, a seventh version of it. And then what happens if you don’t remember what the first five are? Well, then you could jeopardize what the scope used to be. You could jeopardize some sort of pricing consistency and ultimately make a bad impression on a customer. So there are plenty of good reasons when it is appropriate to email. What we want to discuss on this show is kind of some good ideas of when and when not to.

Josh Sweeney: Yeah, and the interesting thing is here, I know sales leaders are like, do I really need to talk to my team about what medium to use and when? But it’s important to keep in mind, like when we think of these episodes, they come from real world scenarios where things went wrong. So this came up from a real world scenario where we’re like, huh, maybe we need to be training people a little more on when to email, when to use other mediums, what not to email

Taylor Barnes: Mm Hmm.

Josh Sweeney: And just be a little more diligent about that.

Taylor Barnes: Exactly. And just to touch on that one more time, and because I think that’s such an important piece here, you know, we might talk about our opinions here and there. But what we’re coming out with is real world experience. I mean, I can tell you that. And Josh, I know you and I are about the same age in 2000 when we would sit there and call people and tell how much things cost. And then we would wait by the fax machine for the purchase orders to come through and we would line up at the fax machine and say, if there’s that or is it is that yours? And, you know, tear off the sides of the paper and then move on. And then obviously, we are nowadays a whole lot more evolved, you know, technologically. So it’s not to say that one was right or the other, but there is absolutely still a need for people to understand when maybe a little more, I don’t know, a little more human touch, a little more personal touch, a little more. You know, a vocal touch is needed versus someone that, you know, sits behind a computer all day long and really has no clue what their customer may look like, may sound like it’s simply put a little bit more challenging to develop an adult professional relationship. If you don’t switch up the way that you communicate and know when or when not to.

Josh Sweeney: Yeah, most definitely, and I mean, another example just popped into my mind, like one of my pet peeves is somebody prepares a proposal and then emails off that proposal.

Taylor Barnes: Yep.

Josh Sweeney: All of a sudden that’s that same rap that’s going to email it for convenience and then complain that now they’ve been ghosted and they can’t get that person on the phone because they’re deliberating, they’re deciding at the price. Right. The pricing is way off from what they discussed. Whatever it is. But they don’t know what it is because they can’t get that person on the phone. Whereas if you would have just emailed and said, hey, we’re scheduling a meeting to go over this proposal,

Taylor Barnes: Mm hmm.

Josh Sweeney: We need to talk about this. You know, we want to walk through it with you. That solves all sorts of other downstream issues. So there’s all kinds of instances where just emailing and choosing, hitting that easy button causes downstream problems.

Taylor Barnes: Absolutely.

Taylor Barnes: Yeah, yeah, and I think that’s a really good segue into some of these solutions. So, again, the challenge, your sales reps don’t know when or when not to email some of the points we went over. You know, it’s an easy board. It’s quick, it’s comfortable, possibly generational. They’re more likely to kind of accidentally addicted to that option as some of the the reasons that they do, but they maybe not should. And then, of course, the reasons that make perfect sense around, you know, things like audit trail proposals, keeping track of different versions of proposals, which is really good in terms of, you know, business continuity. So, Josh, in terms of the solutions, right. You mentioned earlier that you’ve got kind of a high touch culture as part of what you’ve, you know, experienced in your day. Give us an idea of one of the solutions that you think might, you know, resolve these challenges.

Over-Communication is Key

Josh Sweeney: Yeah, so we start with solutions that are like value based and how do we reinforce those philosophies and values onto the team? So one of our values, our founders scale, is called uniquely better relationships. And it’s all about how do you go above and beyond to continuously build a better relationship than any other company would. So whether that’s picking up the phone, whether that’s meeting them on their terms, on how they want to be communicated with, whether that’s sending them thank you notes and postcards. And there’s all kinds of things we can do to have a uniquely better relationship. Another way that we build that and it’s not a value, but it’s something that we reinforce constantly in our organization is what we call overcommunicate. So we tell people overcommunicate, you know, pick up, pick different channels to communicate it on overcommunicate, make sure that the client, the customer, the prospect has everything they need and go out of your way to even provide more.

Taylor Barnes: Mm Hmm.

Josh Sweeney: More than what they need, whether it’s an introduction or anything else during the sales cycle that we can provide, go do that. So reinforcing that high touch culture and the uniquely better relationships drives the the constant goal of, OK, well, how do we do that? Well, you pick up the phone, you write a postcard, you know, you reach out in different ways. Here’s how we do it.

Taylor Barnes: Mm hmm, yeah, I like that, and high touch culture, you know what you just mentioned a lot of that I think comes down to, you know, educating them when and when not to use it. So, you know, I can tell you when I’ve got 50, 60 sales guys and girls on our team. And I can almost see a lot of them when they want or just reach out and say, hey to a customer. They’ll send Jim an email that says, hey, man, what’s up? How’s it going? It’s like,

Josh Sweeney: Yeah.

Taylor Barnes: Oh, my goodness. OK, this isn’t that. And look, I’ll be the first to admit that.

Josh Sweeney: Sounds like they should have been showing up with, like a six pack of beer to see how they’re doing, right.

Taylor Barnes: Exactly.

Josh Sweeney: Yeah.

Taylor Barnes: That option, you know, 8:00 a.m. you want to show up with your customer. That’s better than sending an email.

Josh Sweeney: Bring a coffee, Let’s chat.

Taylor Barnes: Yeah. And so what we say is, you know, it’s very important that you be intentional with your email communication. And again, there’s a lot of different ways where this is very, very important in real world, a real opportunity, real delivery, where you need to keep audit trails of activity and notes and meeting minutes and to publish things like that. Guys, you’ve got plenty of excellent uses for email, so I’m not trying to bash on it. But when small talk, when relationship building, when touch points, when simple responses when. Yes, no, I mean all these different little things understand that that’s not being really intentional with email. All that’s doing is being just kind of casually conversational. And that’s something in our opinion, as leaders in business. And I can tell you, this comes from a lot of feedback from a lot of leaders out there in the world. It’s understanding when and what not to use it based on communication. So as sales leaders, just think of it as a yes and no chart. And in your business, regardless of what industry that you’re in, one is a good time to use it. Is it when we propose, is it when we change? Is it when we send meeting minutes? Is that when we’ve got true audit trails? When is it not a good time to use it? When you’re saying hi, when you have an argument, when you’re disagreeing on something, think things like that. And gosh, I could go down a rabbit hole on the disagreements. How many times have you seen an email fight?

Taylor Barnes: Most uncomfortable thing I’ve ever experienced.

Josh Sweeney: Right, Just get on the phone, get on a zoom, see it face to face, work it out.

Taylor Barnes: Exactly, and people I will tell you this, and I’m sure you’ve heard it, but let me reiterate this a thousand times over email communication is completely up to the perception of who is reading it. So if you’re trying to be nice. It is impossible for a human to think you’re being mean if you are if they are hearing your voice and looking at your face, if you’ve got this big smile on your face and you say, hey, what’s up? Well, that’s probably a very nice, generous, I don’t know, courteous conversation, whatever. But someone on the other end of that email could read this. And then it’s and then it’s just so down in the dumps. I don’t know, maybe he’s upset. Maybe maybe she’s worried about something. It is completely up to perception. And that’s why it’s really important that when your email communication goes out there, it’s very, you know, matter of fact, it’s, you know, updates and factual evidence. It’s history of activities, proposals, what have you. Things that don’t carry a lot of emotion. But if you’re in the middle of a disagreement, if you’re in the middle of trying to build a relationship, if you’re in the middle of touching base with something, then understand that the way that you communicate could possibly be perceived incorrectly on the other end of that email.

Josh Sweeney: Yeah, definitely, I mean, early on, you hinted at the education piece, right, so there’s all kinds of solutions where, again, it sounds like this isn’t a problem until it is a problem. Right. So you can proactively educate on what are your protocols versus internal versus external emails

Taylor Barnes: Exactly.

Josh Sweeney: What do you want? People like maybe internal you’re a little more loose with what you decide. Actually, maybe you’re tighter. I don’t know. You know, what do you want to do externally? What would you want to send externally? So there’s some kind of rules you can put in place and start to train people on and set expectations. You know, I know in my email sometimes I’ll see things going back and forth from the team. I’ll say, hey, you know, looks like this is too much for email. Let’s let’s jump on a zoom car real quick.

Taylor Barnes: Mm hmm, yeah.

Communicating on Multiple Channels

Josh Sweeney: Everybody available now? And try and preempt that. So there are ways that, you know, if you see that happening and you’re on the thread, you can guide them as a leader into the direction you want them to go and reinforce, you know, hey, different channel, different medium, different way to go about this.

Taylor Barnes: Yeah, and let me ask you a question on something that you brought up earlier, because I think this is really important for people to hear. I know just knowing you well enough at this point that before you’ve had a sales organization where you’ve sent a proposal and you’ve waited. But you mentioned earlier that one of the things that you educate on is sending is not sending a proposal until you’ve actually had a phone call or some sort of meeting. Can you tell everybody in terms of that specific solution, really what that’s done and the differences that you’ve seen accordingly?

Josh Sweeney: Yeah, I mean, the difference you see is a big impact to the sales cycle, because when I get when I send somebody an email and say, hey, this proposal is ready, I want to share with you what day can we get on a zoom? And normally they’re wanting to see it as soon as possible. They want that proposal. And so if we jump on a zoom or jump on a call or whatever it is, I get immediate feedback. Right. I can immediately see, like, oh, was this number. They’ll tell you, oh, well, this isn’t what I expected or this is more than I expected. Or, you know, I’ve had people that said, oh, well, did we leave this out? Like I thought this was I thought we discussed this and this was going to be in the proposal was actually they were adding stuff to the proposal, you know, which is a good thing,

Taylor Barnes: Mm hmm.

Josh Sweeney: You know, because sometimes you’re going back and forth on different solutions and you don’t get a clear answer. Right. So so automatically you’re getting all this feedback about the proposal. And I find that that just doesn’t happen when you email it. Normally, all of those things that they would say if you were alive, don’t ever come into play. They go off and they talk about it with the team and they have their own perception. They get busy and they get they get harder and harder to get in touch with unless there is a very, very strong need for them to get that closed in a time in a timely manner.

Taylor Barnes: Yeah.

Josh Sweeney: So I think it impacts the sales cycle very heavily. And your ability to overcome those objections

Taylor Barnes: Exactly.

Josh Sweeney: Quickly as a sales rep. Right. You’re already on the phone. Oh, no problem. I’ll get that fixed or. Oh, well, here’s what we meant by this section. Would you like me to add some verbiage to clarify it? Boom. Now I’m updating the proposal and SOW and everything’s aligned in one phone call instead of like ten emails in three weeks and whatever else goes into it. So those are all the different things

Taylor Barnes: Hmm.

Josh Sweeney: We saw.

Taylor Barnes: Think that’s I think that’s great. I also think a side effect of this is that you’re creating mutual accountability for your customer. Your customer wants something from you. Well, that’s a give. And you should create some sort of get. So maybe a good gift to get is just like this. If you’re very serious about taking this proposal, you know, if you’re serious about taking this proposal seriously, then let’s make sure that we get on the phone and walk through it and and you’ll learn a lot about some customers and prospects if they’re not willing to get on the phone and they just say, just send me the numbers, send me the number. Well, you might learn something that you might learn a thing or two about that specific

Josh Sweeney: Oh, yeah.

Taylor Barnes: Opportunity at that point. So I love the fact that that creates you know, I think that’s a really good just I don’t want to get too off topic here, but I do think that’s a really good step in the customer journey. To add to your sales cycle, if you don’t have one right now, is really establishing that at the proposal. Level one, the customer first sees the commercials. You want to be with them as close as you can to see and feel their reaction and hear their feedback and overcome the immediate obstacles. Just give your chance. Give yourself the best fighting chance at learning how your customer is going to react when they see some numbers. Right.

Don’t Send That Proposal Just Yet!

Josh Sweeney: Yeah, most definitely, and I mean, you make a huge point around when people in my experience, when I’ve had those clients that just said, send it to me, send it to me, send it to me, they generally have they don’t have a value for your time. And the work that went into that proposal and something’s something’s usually amiss. So I’ve had people where they said, just send it to me, just send it to me. And I complied. And I know, again, another rule, we don’t email proposals without having a conversation. And no matter how much they beg you to send it, we don’t we don’t comply because

Taylor Barnes: Mm hmm.

Josh Sweeney: Every time I’ve ever done that, it’s backfired. I mean, I’ve had people go I’ve had people go completely off the rails and follow up because they didn’t like what they saw or, you know, there was just all kinds of ways that that’s gone wrong, where we complied with them and

Taylor Barnes: Yeah.

Josh Sweeney: Just sent it, fired it over instead of having a chance to talk to them about it.

Taylor Barnes: I think it’s great. I think it’s great and you know, just lastly, one of the solutions you mentioned a second ago, internal versus external, I will tell you that I also have a rule, Josh, in my organization, especially when it comes internally, there are no more than two email responses allowed internally without pick up, pick up a phone call. So I don’t know how many times you’ve seen this in your organizations, but I see it daily.

Josh Sweeney: Oh, Yeah.

Taylor Barnes: Especially

Final Thoughts on Email

Taylor Barnes: With some of our younger folks. And again, I’m not trying to say anything bad about the younger folks. We love our people, but it’s just become so normal for them to communicate. So they’ll say, hey, are you working on this? And I’ll respond. Yes, I am. And the response back. Are you sure there is. Yes, I got to get on the phone. What you’re trying to establish in this communication could be solved in 10 seconds, but now it’s across the ether and it lives in the world of the Internet forever and most likely in your inbox for a long time, too. So just pick up the phone internally. I get that you need some back and forth. That’s very important to hold people accountable. Written communication update. There’s a lot of stuff that’s good about even the internal email. But if you’re going back and forth on something more than twice, it is time to pick up the phone. And that is a rule if you’re going to come work with Taylor Barnes, that that is my pet peeve. You’re going to pick up the phone no more than two.

Josh Sweeney: Yeah, I totally agree. I mean, I don’t know how many times I’ve seen things go back and forth again could have been solved very quickly. So

Taylor Barnes: Exactly.

Josh Sweeney: Our final question to you as sales leaders is how are you ensuring that your reps use the right communication channels at the right time?

Taylor Barnes: And this has been Purpose-Driven Sales with Barnes and Sweeney now go lead on purpose.

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