Standing Out in the Inbox: The Art of Sales Outreach

Summary

The Advanced Selling Podcast: Episode Summary Episode Title: Standing Out in the Inbox: The Art of Sales Outreach
Hosts: Bill Caskey and Bryan Neale
Release Date: March 3, 2025

In this engaging episode of The Advanced Selling Podcast, hosts Bill Caskey and Bryan Neale delve into the nuanced art of personalized sales outreach, contrasting it sharply with the impersonal, mass-produced communications often facilitated by artificial intelligence (AI). Through a blend of personal anecdotes, professional insights, and practical strategies, they underscore the importance of authenticity in building meaningful client relationships.

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1. Setting the Stage: Personal Anecdote on DIY Challenges

Start Time: 00:29 – 03:56

Bill Caskey kicks off the episode with a relatable story about his recent attempt at a DIY project—installing curtain rods. Despite his best intentions, the task unfolds into a two-hour ordeal fraught with tool mismanagement and unforeseen complications:

Bill Caskey [01:37]: "I must have made 100 trips to the garage to get first, you know, first a saw and then a screw driver."

This anecdote serves as a metaphor for the broader topic of the episode: just as Bill's well-meaning but unprepared approach to DIY leads to inefficiency, so too can sales outreach falter without the right strategies.

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2. The Essence of Personalized Outreach in Sales

Start Time: 04:17 – 07:55

Transitioning from personal stories to professional advice, Bill and Bryan address the core theme: personalized outreach versus AI-generated mass messaging. They highlight a growing concern in the sales community about the over-reliance on AI, which often results in generic and inauthentic communication.

Bryan Neale [06:08]: "If those words are in your pitch to us, I know it's AI, and I know it's not authentic."

The hosts caution against the sterile efficiency of AI-driven emails loaded with buzzwords like "delve," "skyrocket," and "game change," emphasizing that such language can signal insincerity to recipients. Instead, they advocate for a more human-centric approach that resonates on a personal level.

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3. Strategies for Authentic Outreach at Scale

Start Time: 07:39 – 11:58

Bill and Bryan propose actionable strategies to maintain personalization without sacrificing scalability:

• Humanize Mass Emails: Even when sending to large groups, incorporate elements that reflect genuine personality and intent.

  Bill Caskey [07:22]: "Be yourself and be authentic."

• Leverage Direct Communication Methods: Utilize voice memos or personalized scripts with variable elements (like first names) to add a unique touch without being overly time-consuming.

  Bryan Neale [11:32]: "You could even mass produce those. They don't have to necessarily be custom, but if you're only doing 10 a week, you can do it custom pretty easily."

These approaches aim to bridge the gap between efficiency and personalization, ensuring that outreach efforts feel both sincere and effective.

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4. Real-Life Example: The Blind Zebra and Wise Rhino Connection

Start Time: 12:03 – 17:52

To illustrate the power of personalized outreach, Bill shares a compelling interaction with a contact from an intriguingly named company, Wise Rhino Group:

Bill Caskey [12:04]: "A blind zebra and a wise rhino walked into a bar, dot, dot, dot. It's very clever."

This lighthearted and tailored message stands in stark contrast to the impersonal, formulaic approaches they critique. The immediate, authentic response he receives underscores the effectiveness of genuine engagement.

Further emphasizing this point, they discuss how such personalized connections can lead to significant business opportunities:

Bryan Neale [17:14]: "Little gesture can go a long, long way."

Bill adds that maintaining these authentic connections can open doors to unexpected ventures, such as podcast appearances or strategic partnerships, ultimately driving business growth.

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5. Key Takeaways and Conclusions

Start Time: 17:05 – End

Wrapping up the discussion, Bill and Bryan distill their conversation into several key principles for effective sales outreach:

• Authenticity Over Automation: Prioritize genuine communication over AI-generated templates to foster trust and rapport.

• Personal Touches Matter: Even small gestures, like personalized messages or thoughtful responses, can significantly enhance connection quality.

• Consistency is Key: Regular, sincere outreach efforts can compound over time, leading to substantial business growth without the need for overwhelming scale.

Bill Caskey [17:05]: "Less is more... it's calm, calm, calm, you know, on that."

By integrating these principles, sales professionals can navigate the delicate balance between efficiency and personalization, ensuring their outreach efforts resonate deeply with prospects and clients alike.

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Conclusion

In "Standing Out in the Inbox: The Art of Sales Outreach," Bill Caskey and Bryan Neale effectively argue for a return to human-centric sales strategies amidst the rise of AI-driven communications. Through personal stories and practical advice, they inspire sales professionals to embrace authenticity, thereby enhancing their ability to connect, engage, and ultimately succeed in building lasting client relationships.

Transcript

[A]

Foreign. Welcome everybody to the Advanced Selling Podcast. The longest running sales training podcast in the history of podcasting. My name is Brian Neal.

[B]

My name is Bill Caskey.

[A]

Here every week for your listening enjoyment. Two things we always remind everybody to do. Go join our LinkedIn group and join the Insider program. Monthly live training with my friend Bill Caskey and biggest bank your bucks. I always say in sales training, coaching, live stuff. Great community too. Great people.

[B]

It is a good community. A lot of back and forth between the members and if you haven't, if you haven't checked out the calendar for the year, we have a March episode training coming up. You can go to advanced podcast.com insider. The whole year is laid out for you.

[A]

That's great. Yeah. What's coming.

[B]

I had, I had a funny thing happen. You know, we've laughed on this show about how I'm not a, a DIY guy. Yeah, just look at my tool chest kit out. I wouldn't even call it a. It's a thing on rollers that has a lot of crap piled on top. And I kind of know where it all is though. So if you say, look, I need some caulking, okay, I can find that. But I'm just not, I'm just not cut out for that. So yesterday we had everybody over. Yesterday was my birthday.

[A]

Oh, happy birthday.

[B]

I forgot.

[A]

I had that all queued up. Dang it.

[B]

Everybody came over and the idea was Cody, my son in law, Kara's husband, was going to help us put up these curtain rods because we got some new blinds and they had to be pulled off the wall a little bit. Anyway, it's not something that I, I mean, I could do it, but you know, when you have a young person who's in construction, he can do it in probably five minutes. It would take me an hour.

[A]

Right.

[B]

And. But Kara had a kind of emergency trip to the hospital. Everything's fine. But she had some real bad, just a real bad stomach issue. She gave birth about two weeks ago. It's pretty normal, you know, constipation and stomach stuff. Anyway, so they took her. So. So obviously not only was I concerned about her, but I was concerned this job was not going to get done. This curtain job was not going to get done because I could see he wasn't. His mind was somewhere else than it should have been. So I thought, you know what, I'll tackle it. So after everybody left, I'm upstairs and I'm, I must have made 100 trips to the garage to get first, you know, first a saw and then a screwdri driver. And then I'm so unprepared for stuff like this. You know, the ideal thing is to think through, okay, what are all the tools I need? Go to the toolkit, bring them up, put them on my belt, my tool belt, and then go up and go to work. So anyway, I got it done. But the, the argument was with Jane was she goes, you got to find a stud. You got to find a stud to put this in. And I'm like, well, aside from the sophomore comedy of studio, I'm like, well, there's three brackets and only one, the middle is in the stud because it's in the center of the window. And that's where the stud goes. And I said, she goes, oh, yeah, it's got to be in a stud. Well, that's her father. Her father was a stud guy. I mean, you know, he never put anything up. The problem with that is that studs aren't always conveniently located right. Totally within the wall.

[A]

Yes.

[B]

And so then we looked at the studs and you'd have to. I would have to have gotten a rod to extend the rod. It was way far out. And so final. And then fact is, the one that was up there was non stud, so. But I did have a little trouble with the anchor. You know, you put those anchor bolts in, shove them in, if they're not shoved in properly, they'll just turn. And so anyway, it was, it was a good two hour project. That should have been 10 minutes. And then I had to, I had to move something. I'm like, do I want to do this tomorrow? Nope, nope. Do it right now while you got all the tools. So eventually, project completion number. Do it DIY number three in the last 25 years.

[A]

Are the shades up and hung properly?

[B]

Shades up. Yeah.

[A]

Sun is out. It worked.

[B]

Looks great. Yeah, it looks.

[A]

That is the stud.

[B]

Yeah.

[A]

And I don't do it. I'm like, you even worse. Probably at this point, I won't even try anything. But this stuff. I know the guy or the person who you gotta be on the studs. Like you said, the studs have been set for 25 years behind the wall. We're not moving the studs. So either gotta have a curtain rod that goes four feet exactly the window or just do what you did, which is anyway.

[B]

Or the way these brackets came, they came with little anchor bolts, which tells.

[A]

Me, oh, they're expecting that you can't find stud. Yeah.

[B]

So I finally.

[A]

And God bless Don.

[B]

Finder stud finder out there.

[A]

And there, I'm telling you, there's not a man on the earth, regardless of age, who doesn't take that thing, turn around, point at himself and go, there's one. One. Every guy talking about, if you have a stud finder, we can turn it and goes, oh, babe. So we had a little conversation. We get requests all the time of people to be on the show, and usually we don't have people on the show because it's me and Bill talking. And it got us talking about just personalized outreach. And so from a topic standpoint, today, we want you to think about what is your voice? What does your voice sound like in your outreach? And by outreach, we're meaning if you're in LinkedIn putting up video content, if you're put. If you're doing your own podcast, if you're on a podcast, if you're a CEO or VP of sales and you're a guest on a show, or your email outreach, or you're cold calling, if you do that, what does your voice sound like? And specifically, have we gone too far in the mass production of things using AI? And should we come back a notch to a more personalized outreach? What should we do about that for salespeople? How do we scale?

[B]

It's a good topic, and it's. It's fresh on our mind because we get a lot of requests to be on the show, and we just talked about one this morning. A young person or person emailed us, and the more we talked about it, you can always tell the emails that are either A from a PR firm.

[A]

Yep.

[B]

Or B, from a PR firm and AI generated. There's key words like delve, skyrocket, game change. If those words are in your pitch to us, I know it's AI, and I know it's not authentic. Now, I'm all for using AI on things, but you got to be really careful that it has your voice and it sounds like it's a real human being. And most of the time, it doesn't.

[A]

Yes.

[B]

So there's that, and then there's also this email blast thing where we just. We have gotten to the point where we got to get an email out this week. Okay, well, let's blast one out. And. And there's no personality to it. It's all very corporate vernacular and marketing jargon. And I think it's time. You're right, Brian. I think it's time we go back and say how even though it might be a mass email, it might be something we're sending to 300 people. How do we at least make it sound, make an effort that it sounds a little more personal?

[A]

Yes. Or what about this? This just popped in my head. If I'm truly sending a mass email out. Let, let's just call that what it is. Like we're sending this out to my entire list. You know, if you subscribe to anything from Bill Caskey in the last 20 years, you're getting this email. Thank you for however I met you then. It's real. Because that's real.

[B]

That's right.

[A]

Versus trying to personalize the thousand. Four thousand person outreach too much.

[B]

So yeah, when I say personalize, obviously you can't personalize to each person but it's, it's more just the, the cadence of language. You know, does it, does it sound like it came from a human or a machine?

[A]

Yes.

[B]

And, but yeah, if you, if you could just say, look, this is something that's going out to the, to the masses and I just wanted to be clear that that tells me that because an AI would never say that.

[A]

Yes, yes.

[B]

Trying to hide, don't try to hide it. Be, be yourself and be authentic. Yeah.

[A]

And I see this. I have a couple friends who have really big jobs in publicly traded companies and joke sometimes about their. And then one's in a company that's technically not traded but it's owned by really one of the wealthiest people on the planet who has a company in Nebraska that owns a lot of other companies. You can figure that out. And the joke or the kind of, the thing that I always ask them about or rhythm a little bit about is when they put stuff on LinkedIn, is it really them? And so two of my friends, it's never them, it's their marketing team is responding and you can tell, you can tell. It's so obvious, you know, it's so generic, it's so corporate, it's so machine oriented, it's so safe, blah, blah, blah. And then occasionally the, my other friend will, you know, he'll pop in, but it's very, very light and I just wonder what, what would happen if those people this decided to run their own account, so to speak. Yeah, you will, you know, and really get, you know, just get real on LinkedIn and make it your own. And I know some people that do that, you know, where it's them, you know, talking and I think you have to. I do too.

[B]

I think you have to. I think as, as AI becomes more, more, you know, ubiquitous.

[A]

Yeah.

[B]

There's a word for it.

[A]

I like it. Put that in an email. It's very ubiquitous.

[B]

I don't know how to spell it.

[A]

But I don't either.

[B]

Ubiquit. We. Us.

[A]

Yeah.

[B]

Our sixth sense becomes better, becomes stronger. It's going to become super strong. Even when we see something today, even if it's a video, we still have a sixth senses. I'm not sure that's right. That just. There's something about that. It just doesn't seem right. So your prospects are the same way. They are. They're. They're. Their shackles have been risen and it's. And they will. They can tell. So, yes, point one of one. Point number two is if you are trying to get on a podcast or on a YouTube channel or trying to be interviewed by somebody, you know, that's one of the things that I'm recommending to all of my clients who are in the business, to business space is chances are there is a podcast or alternative media outlet in your space that interviews people like you.

[A]

Yep.

[B]

Why wouldn't you be on those shows? They're looking for content. You're looking for promotion or for spreading of the word of your message. You should be on those. Those. And then the question is, okay, once I find those, how do I land a spot? How do I get invited in as a guest? And that's where this email comes in.

[A]

Yes.

[B]

And this is where you have to. If it sounds like everybody else, if you're hiring a PR firm, I wouldn't do that. I would just send an email, say, hey, I listen to your podcast. I'm in this space. I'm. I really am glad you're doing this. Would it make sense for us to have a conversation to see if I can bring any value to audience?

[A]

Yes.

[B]

It's simple. It's not 17 paragraphs about how great you are.

[A]

I know, it's so easy. And people that they want to. And again, nothing against the PR firms, but they want to, like, mass produce, mass scale this thing. So they blast it out and then they turn off some people that could really be good, you know, a good connection for them. And what you said, Bill, is so true. It doesn't take a lot of effort to leverage this thing up. It takes a little discipline on your calendar. And if you spend, you can sit down and spend. Send three or four of these out these outreach things to podcast people three times a week. If you do three per setting three times a week, that's nine times four, that's 36amonth times 12. Now we're getting a big math. You're going to get on some shows. That's right. And that is not a lot of time. It'll take you 10 minutes to do, you know, some direct outreach. And if you're doing it on podcasting, do a voice memo.

[B]

Absolutely.

[A]

Like, why would you do a voice.

[B]

Absolutely. That's exactly how I would do it. Even if a video might be overkill, but a voice memo on your phone to the person, you can get, you can get phone numbers or you can email. You can email the voice memo. Yeah, that's exactly what I would do. You could even mass produce those. They don't have to necessarily be custom, but if you're only doing 10, you know, 10 a week, you can do it custom pretty easily. It's the same script, just have a different first name.

[A]

Yes. Can I give an example of something that's just easy and easy to do?

[B]

Yes, sir.

[A]

This came from in my LinkedIn inbox. And my. My company's called Blind Zebra. And this guy's company is called I Gotta get it Right. Wise Rhino Group. Okay. So I saw him connect, you know, I sent him in a connection request cold or something like this. He responds almost immediately. A blind zebra and a wise rhino walked into a bar, dot, dot, dot. It's very clever.

[B]

Yeah.

[A]

Win sense. Took him two seconds to write that. I immediately write back, lol. Too easy. I was thinking, I was thinking I had to send a connect. Saw you tagged in Brit Anderson's post. They're great people. You wrote back immediately. Ha. Cannot resist the other great people. Put on a great conference. Cheers to unique company names now.

[B]

Yeah.

[A]

He goes, okay, so what? Where does that go? The point is, this guy runs an M. A firm, seems like a pretty big job and just takes a little time out of, you know. And now I'm thinking, oh, gosh, if I, you know, could I connect with him? I follow him now. It's. That's so engaging versus the ones that come that are automated. You know what I mean?

[B]

Absolutely.

[A]

Hey, Brian. I also have some mutual connections. I'm always looking to expand my network. Okay. Then an hour later, thanks for connecting. You've always helped one because you reached out with saving 30%. And here we go.

[B]

Here we go.

[A]

I just wrote back, no, thanks. It's like, I don't know, when you.

[B]

Start this relationship with this person. Wise Rhinoceros now. Whenever you. You're connected now and. But you're not just connected, you're connected with a little bit of rapport.

[A]

Yes, that's.

[B]

And so now when you create content and the Wise Rhino sees it, he sees it differently than if you were just a name and a, you know, in a barrel. It's, it takes on totally different. He feels like he knows you a little bit. So your video is going to get through and then he's going to refer that video to somebody else and before you know it, you're going to be sitting in a boardroom somewhere. But it all began with you taking the time to. Or somebody taking the time to have a little fun.

[A]

That's it. Yeah. In a sentence, less than an incomplete 30 seconds. And here we are talking about them on the podcast. How this works, you know, this business explodes.

[B]

Your business explodes.

[A]

Wise Rhino sells for 42x multiple after.

[B]

Two years due to a podcast.

[A]

You never know, though. And then someone listening is going, I work at Wise Rhino or I know those guys. That's what this works.

[B]

And he's got companies all of whom should be listening to the event selling podcast. Everybody wins here in this. And I think if we look too narrowly at it and we, we push focus in and just say, well, I don't have time to make fun of Wise and Blind zebras. You're, you're losing the big picture. You're losing the big picture because I, I think we resort to business and I'm guilty of it. Is business so frequently that we don't spend time with just the personal stuff? Hey, that's kind of cool. You got an animal, I got an animal. Huh? Kind of the same. All right.

[A]

Exactly.

[B]

Yeah.

[A]

And it's, it tells me he's paying attention to little things. He's not just like, look like, okay, now sometimes there's nothing there, but anytime there's anything there. I was going through one the other day. This guy there, one of my clients just got a new CEO and I'd heard news of that but didn't know. And so I'm like going to look at the new CEO and I just see that he was. I was a Beta as a fraternity, I was a Beta at Indiana and he was a Beta at mit. So there's no guarantee that he's we're going to love each other or anything like that. But we have this little. But it just get to scroll down to find it. And most people don't do that. They don't do that next level of just looking. And that's all it takes.

[B]

Yeah. One thing, here's something that I have found. I get, we get a lot of LinkedIn requests because of the podcast. And whenever someone requests to whatever connect I always ask, and if it looks like somebody that was legit, then I will always accept. But I'll always say in the acceptance, in my acceptance speech, I will always say, how did we, how do we know each other? Yeah. Or what, what prompted this connection or something. That's just very simple. And 90 of the time people say it's a podcast, but then I get a little bit more information. They say we've been listening for 12 years and we love it. And our. And then I can get back to them. It's not a long conversation, but sometimes if somebody's connect, wants to connect with you, just ask them how, how did this come about? You might me might surprise you about how these things happen.

[A]

Yeah. And so I think the lesson if you're listening to this today is you're asking yourself, how am I taking these little extra steps for personalization to, to delve a little deeper and, and I think shrinking. The other thing that was coming to mind for me too in my, I read my little exchange with the rhino guy is less is more. In this, you can start a little convo with a couple sentences and not this big, long, earth shattering idea, you know, world record, you know, four, game changer. It's like calm, calm, calm, you know, on that.

[B]

Yeah, totally agree. All right, good topic. So I, I think this, for me, the lesson is even a little gesture can go a long, long way.

[A]

Yes.

[B]

And if we look at everything like we've got to have 40 million subscribers and 10 million podcasts.

[A]

You don't, you don't.

[B]

You only need the one that's going to take you to the five, that's going to take you to THE 50. Yes, possibly. And you just have to, you know, treat this business like you would if somebody came up to you on the street and said, hey, Brian, you would say, hey, I'm sorry, I forgot your name. How do we know each other? And you would say, well, you were, you know, 17 years ago, you did a training for. Oh, forget, of course. Why did I not remember you there in the back row? Not remember you. Anyway, I remember that. All right. Okay, see you next week.

[A]

Bye.