It’s a new year and a new decade. It’s also no coincidence that 2020 also refers to vision with perfect clarity. In this very special episode of INSIDE Inside Sales, Darryl goes solo to recap the best sales tips from 2019. If you want to be equipped with some solid, proven, and powerful advice, then this episode is an absolute can’t-miss! Reviewing the lessons learned in 5 episodes from 2019 (featuring industry experts such as Andy Paul, Jason Bay, Benjamin Dennehy, Randy Riemersma, and Mike Weinberg), Darryl will discuss easily actionable steps to intentionally invest in yourself, as well as provide you with some effective tools that will help transform you into the Rockstar Sales Leader you know you can be! Make it a truly Happy and Prosperous New Year by starting off listening to this highly impactful episode of INSIDE Inside Sales!

Not in the mood to listen? No problem, you can read the transcriptions below.

[bctt tweet=”What were the best tips and tactics from 2019? 🎧 Listen as @ohpinion8ted shares lessons learned from 2019’s top 5 INSIDE Inside Sales podcast episodes. #SalesTips #prospecting” username=”VanillaSoft”]


Host:  Darryl PraillVanillaSoft


Moving Ahead by Looking Back

How are you doing folks? It is another episode of Inside Inside Sales. Funny story, often when I go speaking, those of you who listen to the podcast, like you’re doing now, and know me, will introduce me and mention the podcast, and then they’ll turn to me and they’ll say, “Hey, Darryl, can you talk about Inside Inside Sales, “the way you do on the podcast?” I feel like a little dog who has to bark or play dead on demand now, but you know what, I’m cool with that because I like saying it and I like that you guys like hearing it. If you are listening to this in series, then you will know that this is the first episode of 2020 and if you’re listening to this on demand and you’re playing catch up, welcome to the year 2020. There we have it.

We’re gonna do something a little differently today, something we have never done before. We’ve talked about doing it but we’ve never done it. So, this is gonna be you and I, we’re gonna experiment on this together, this format, and see if we like it and if we like it, maybe I’ll do it again in the future and if you don’t like it, well then tell me that, too. And what is that? Well, it’s very straight forward. I actually have no guests today on the show and that’s intentional. I intentionally chose to have no guests and let me tell you, I’ve got a gazillion guests lined up. 2020, it’s gonna be stellar. I’ve been getting all the yeses and the affirmations and I’m in emails all this week. I think next week alone, I’m doing four podcast recordings. It is out of control.

All of this is building up to the sponsorship, where, you may not know this, VanillaSoft is the title sponsor of the OutBound Conference, and if you haven’t been to the OutBound Conference, well, you should, but what’s so relevant about OutBound 2020 is the fact that you have amazing speakers who recognize the importance of outbound, all right. So, marketers will tell you that the holy grail is inbound and a lot of sales reps are busy following up on inbound leads but the truth of the matter is, sales is just as required to do outbound activity, where you identify your own list and your own targets, especially something like account-based marketing, for example, account-based selling, target account selling. Without marketing, marketing’s there to support you, not to lead you and so, the four individuals actually sat around in the very beginning and they said there’s this huge conference called InBound, which of course is put on by HubSpot, but no one’s doing outbound and that’s where the OutBound Conference came from, not sure if you know that. It was originally founded by the four horsemen, which is Mark Hunter, Jeb Blount, Anthony Iannarino and Mike Weinberg.

And this year, for the first time ever, they’ve had a change in leadership. Very dramatic, very dramatic, but nothing evil, nothing to be worried about. It’s all good. Mike Weinberg has just gotten too freaking busy and he’s stepping back from the OutBound show, still a huge advocate, still pushing the product immensely, and he’s been replaced by Victor Antonio, and if you don’t know Victor, of course, he’s got over a million followers on YouTube. He’s the man. These four people have led the charge, along with Mike Weinberg, have led the charge on the OutBound Conference and they’ve got some amazing speakers. So, they are there and they bring in the best of the best. All right subject, Andrea Waltz, Amy Franco, Bernadette McClelland, Brynne Tillman, Colleen Francis, James Muir, Jeff Bajorek, Kendra Lee, Kenyetta Gordon, Larry Levine, Luigi Prestinenzi, Meridith Elliot Powell, Shari Levitin, and that’s just the highlights.

There’s more still being added to the list. And all of these people are amazing rock stars when it comes to selling. So, what we’re doing is we’re actually gonna be bringing you a lot of these people, as we build up to the event in May. So, that’s my way of saying, if you’re thinking of going to the show, sign up, If you’re not sure about the speakers, just listen to Inside Inside Sales and you’re gonna hear them over and over again. So, that’s kind of the teaser. Second thing that I want to talk about why I’m doing this solo today, beyond a give myself a heart attack and see if I can do it and put my producer through hell, is because I wanted to reflect. I wanted to reflect back on what we accomplish. You and I together in the year 2019, I had a ton of amazing guests online. If you haven’t seen it, you can go to

Hopefully you’ve subscribed and let me do one requisite request here. Can you please go to Apple or Spotify or whomever and like us and review us? That would be fantastic. It really helps the show. What I wanted to do today was I actually wanted to physically kind of revisit five episodes that I thought resonated with me. So, what does that mean for you? If you listen to the show, that means you’re gonna be hearing the highlights of shows you may have already listened to. So, maybe I’m sorry for that a little bit, but in the same breath, the reason I bring these five up, was because it’s a good recap. What these experts taught us are as applicable today as when we interviewed them way back when, so think of this as a refresher. And it’s also to remind you, go listen to the episodes in their entirety if you like anything we have to say about here. So, that’s kind of the gist of where we’re going from.

Looking Back, Going Forward!

So, let’s go on a little journey together. Back in May, we had the chance to interview Andy Paul. He’s with the Sales House, but even before The Sales House existed, Andy Paul himself was a legend, best selling author, world class sales trainer, and he’s just a humble, nice guy. Slender fellow and just got a great voice. He’s got a voice for radio, if you haven’t ever listened to Andy, listen to his stuff. His podcast is always right up there in the top one, two or three. So, Andy’s a great guy and we work with Andy here at VanillaSoft. We actually sponsor a lot of his stuff because we like his stuff. It’s about giving back to the tribe. And what Andy and I talked about, was about the importance of learning.

So, each of you here are in a profession. You are sales professionals. Maybe you’re an account exec, maybe you’re a sales development rep, but one of the reasons you do this job is because it’s the opportunity to earn a lot of money if you’re good at your job, perhaps more money than any other profession out there. So, how do you become good? Well, of course you should listen to this podcast, but this podcast is an example of actually investing in yourself and learning on your own. So, I guess the question I would say to you is are you intentionally, as you reflect seriously about your own abilities, are you investing in yourself?

Do you intentionally do any of the following: are you going out and buying or borrowing books on sales from the best-selling authors, for example, Mark Hunter, I mentioned him in the OutBound Conference. Best selling author, right. All these guys, best-selling author Mike Weinberg. I had him on the show a little while ago, best-selling author. Are you reading those books? The last book I read was Sales Truth by Mike Weinberg and all I kept on doing, I was reading on a weekend, and I just kept on taking pictures and sending it to my VP of Sales, my CEO, and then say, “Oh, this, we need to do this,” or “Oh, that, see I told you we need “to do a better job over here.”

And what it goes to show you is even though we’re a sales engagement company, you would think we’d be really good at sales, but even we can improve. So, the point is, books are awesome. Now, here’s the catcher, a lot of you think I don’t like to read, I don’t have time to read. I get it. Guess what, they come out in audio, all right. They come in Audible or any of those other places out there. Again, I was talking to Mark Hunter a couple weeks ago and where was he? He was actually in Nashville, in studio recording his book with his voice, which is kinda cool. So, books, podcasts. Podcasts are huge, like this one here. And there’s so many that are out there.

We sponsor David Dulaney of Tenbound, we sponsor his podcast. We sponsor Luigi Prestinenzi ‘s podcast. We are committed to the podcast because we know that it is brilliant. One of the things you forget about, when it comes to learning, is that the more you learn, the more you earn. So, that’s a huge reason alone on why you should be doing it. Now, I mentioned podcasts, I mentioned books, of course there’s YouTube videos of all your major influencers. So all those people I just mentioned at the OutBound Conference would be examples. Go look at their YouTube channels. The next thing of course, is social media. So, especially LinkedIn on the B2B world, LinkedIn. Follow those people and they’re always dropping soundbites.

One of the people I wanna talk about here is Randy Riemersma. I saw Randy Riemersma for the first time on LinkedIn because I saw one of his videos and I brought him on board. So, you need to have a plan for that. Do you have a plan? Have you booked time in your calendar to learn? That’s the first thing.

Improve Sales with Sales Training and Coaching

Now, one of the discussions that comes up is that many reps feel it’s the company’s responsibility to train them, and it is, but if they’re not gonna pay for it, then you’re not gonna learn and I’m gonna tell you this, that’s a huge mistake. Benjamin Dennehy talks about when he goes in and tries to sell his services and they’ll say, “I can’t afford you,” he’ll say, “Well, why don’t you get your reps “to help pay for my time?” And so, when they go to the reps, they’ll say we wanna bring him in, they’re like, yeah, and we want you to help cover the cost, they’re like, no.

I get it but the reality is if you could drop, I don’t know, a couple hundred bucks into your own time and your own skill and your own profession, is that not worth several thousand dollars in return for having more success? It’s like continuing the education, folks. You have to have the right mindset. You have to be intentional. You have to physically focus on what ways you learn best and you have to actually make an investment in that. The next thing is A/B test your learning. So, whatever you’ve got, Brian Smith, Jr. and I talked about this, how he A/B tests what he’s good at and maybe this script works better versus that script so I’m gonna practice that over and over again.

So, all of those are good, but my point of the lesson here is Andy, in this episode, and it was, if you’re wondering, it was episode number 26, talks all about how you can increase your earnings if you just increase your learning. So, go check that out. That’s Andy Paul, follow him, by the way.

Tips for Better Sales Emails

Moving on, then we had a great conversation on June 25th. This is episode number 32 and I was with Jason Bay. Now, Jason’s with Blissful Prospecting and he talks about turning up the heat on your cold calls, but we had Jason on both a podcast and one of our webinars, which the webinar basis was all around stop sending shitty emails ’cause too many sales reps are literally just firing off emails that aren’t converting.

Now, you know this and often your excuse is, I’ve heard this over and over again because I’ve called some of you out on it, is well, it’s a numbers game Darryl, I know they’re shitty but if I send enough out, I’ll get enough responses that I can feed myself. And the reality is, what you’re actually doing is you’re destroying your own base that you should be selling to because it’s like a one and done. You can’t go back to that well ’cause you’ve already angered and frustrated the person with your bad emails way too much, plus your bounce rates and your spam are gonna go through the roof and your deliverability is gonna suck so you don’t wanna do that.

Jason talks about the whole concept of the REPLY method. Now, the REPLY method is a really, really interesting approach. He says structure your email this way: R is for results. So, if it was VanillaSoft, my opening line might be, “Many of our clients using VanillaSoft “can triple their sales pipeline “with no additional investment in processes or people.” E in the REPLY is for empathy. “Is this of interest to you? “Because I can imagine you’re frustrated “with the results your reps are giving. “Most reps are struggling to hit quota.” P is for personalization. “I know at VanillaSoft, it’s real to us. “We feel it in our bottom line. “We’ve had the stress and anxiety. “I imagine you feel this, too.” L is for laser focus. “If you give me just a couple minutes of your time, “I can explain to you exactly how we do this “and you can determine if that’s something “that you can apply to your processes.” And then Y is for you. “I want to help you succeed. “Let’s talk, here’s the link to my calendar.” All right, so, R-E-P-L-Y. If you follow that method, it’s as simple as that.

You’re gonna do amazing emails. The biggest thing in that whole methodology is stop making it about you. “Hi, I’m Darryl, I’m with VanillaSoft. “We do this, we do this, we do this.” Nobody cares. It’s about them. So, it’s not about Y is not for me, Y is for you, the recipient of my email. So, that’s the REPLY method. In that, we go through a number of emails and talk about how they’re so lame. We talk about how templates that are non-personalized and don’t follow this format stink. We talk about some other stuff, right. So, you should assume that your emails are always being consumed on a phone, a mobile phone. If you assume that, versus a desktop, that’s gonna really help you keep them short and tight, so the layout is critical. How do you format them? Small, tight paragraphs, bolding your call to action, for example, personalizing it. That’s massive. If I can skim it, so that I can quickly determine if I have an interest in this or not, and it’s not too long, I don’t have to swipe too many times, I will read your email.

Finally, the last thing is the subject line, okay. Too many of you are using subject lines that are too long. You want five words or less, that’s the first thing. Next thing is, what you wanna do is you ideally, you could get it even shorter, maybe three words, and in fact, one or two words, believe it or not, converts the most. But you also want to personalize it. So, you wanna start with like, “Darryl,” oh now see, I’m blanking again. Triple your pipeline. “Darryl, triple your pipeline.” So, it’s gonna speak to a pain or it’s gonna be provocative, I’ll probably open that. It’s short, it’s sweet, I can see it on the phone. So, it’s personalized and it’s relevant to me and my pain. So that’s your subject line. Do those things and you will be far better. Stop sending out the bad templates.

Stop not proofreading your stuff. Finally, invest in tools that will make you more effective, such as Grammarly, all right. Grammarly is a fantastic tool. It’s very affordable in the big picture, again, going back to investing in yourself, that you can check your grammar, check your spelling, check all that wonderful stuff, so you actually sound as smart as we all know you are because after all, if I’m gonna get into a transaction with you, I’m gonna make sure that we know each other, we understand each other and that I trust and respect you. So, the image you project is so critical. If you can’t spell and you can’t structure a sentence, I’m moving on and that’s huge. So, that was with the great Jason Bay, follow him on LinkedIn. He’s with Blissful Prospecting, episode number 32. With that, let’s take a break and we’ll come back and hit the next three episodes I want to hit upon and we’ll wrap up this show and see how well I fared. We’ll be right back.

Tips for Cold Calling Success

Okay, so the next show was one of the, if not the most downloaded show of the year and it actually goes way back to March. And what you may see here is I’m actually working, not chronologically, I’m working kinda through a sales process. So, first, you learn in yourself and invest in yourself and your own knowledge. Then you might be sending an email to a prospect. Now, this one, episode 18, we talked about the science behind the cold call. So now, you know, maybe they didn’t answer your email, now you’re gonna reach out and you’re gonna call them. So, logic of flow here. And I did this one with Benjamin Dennehy.

Now, if you don’t know Benjamin Dennehy, he is the UKs most hated sales trainer, self-professed, self-declared. He wears a hat, a very red hat a la Mr. Donald Trump and it says, “Make Salesmen Great Again,” and it doesn’t say salespeople, it says salesmen, and he makes no apologies about that and that’s just him being provocative. He’s actually a good guy. He’s got his suspenders. He’s got usually his plaid button-up shirt. He’s got his brand down pat. He pulls no punches, so in that episode, if you missed it, listen to it ’cause you’re gonna hear him and I get into it and some of the stuff he says, you’re gonna go wow, that was bold. And then you’re gonna say but wow, he’s right.

And it was really kind of interesting, in this one he was really kind of saying, and you’ve probably heard this before, the cold call, you’ve gotta agitate a little bit. You’ve gotta up front acknowledge that this is a cold call. So, too many of you are out there saying, you know, someone answers the phone, A, you’re shocked and B, you’re going, “Uh, hi, it’s Darryl. “I’m with VanillaSoft, we’re a sales engagement vendor. “How are you today?” So at that point in time, you’ve lost them. They’ve already tuned out. Too many of you are worried about the cold call. You’re thinking that you’re interrupting them and you don’t wanna be their interruption. You’re worried that they’re gonna get angry with you or they’re gonna just yell at you for doing what you’re doing.

Guess what, when they pick up that phone, they gave you permission right then and there. They could have let you go to voicemail. They could have not answered the phone at all. They picked up the phone, knowing they don’t recognize the number or the name on the display, so they already know that this is probably a cold call, so don’t worry about, don’t feel bad. The next thing is when you get through to the actual, you know, they’re beyond the gatekeeper and you finally got the right person, you don’t mess around. His point is just admit. And the first thing he says is, “Hi, just to be clear with you, this is a sales call.” So, right away, you’re being forward but honest and ironically, what that does it two reactions, one of you, you’re worried the caller’s gonna go, “Oh man.” They already knew that.

They knew when they answered the phone it was gonna be a cold call. The second part is, you are establishing that you’re not misleading. You’re not trying to be something you’re not. You’re speaking truth and they’re gonna like that you’re being forthright and not wasting their time. Yes, there’s always outliers, I understand that, but they will actually appreciate that. The next thing, he goes on is he actually says you’ve kinda got 30 seconds.

More of the Best Sales Tips from 2019

We did an episode with Chris Beall, he says you have 27 seconds, but for simplicity, 30 seconds. And in 30 seconds, you need to be able to get your speil across. The other thing that Chris Beall mentions in another episode, when he talked to a hostage negotiator from the FBI, the FBI says you’ve got eight seconds to establish a connection with them.

If you don’t do it then, then you’re dead in the water. That’s why being forthright and honest with them is so important. So, his point of view is you need to really, really segment your list. You need to know exactly who you’re talking to. You need to know the persona. I’m talking to, I see it says the managing director or the CEO of a company, the company’s in this industry, and the company’s of this size. That’s my list I’m cold calling today. If I know that, then I need to know everything about that persona and the life they’re living and the challenges they’re having, so then you can say, “Hi there, full disclosure, “this is a cold call. “I just wanted to share with you “companies who use VanillaSoft “usually struggle with pain A, pain B, pain C, “and we can help them with that. “I’m assuming you don’t have that problem, “but can I have 20 seconds to talk about it, “in case you do?”

And then the next thing he says is silence is golden. So, just be quiet. Use silence to your advantage. They’re gonna say no or they’re gonna say yes but usually what they’ll say is, “30 seconds?” 30 seconds. “You’ve got 30 seconds, go.” And that’s what you want and now you can go into your spiel. So, that’s the whole thing. The science of the cold call is right there. And then you get in the whole objection handling and discovery and everything else. That’s a whole different conversation, which we did a wonderful episode with Michael Pedone late in the year on objection handling, so check that out.

But that was Benjamin Dennehy on the science behind the cold call. Now, you’ve got that call, you’ve connected with them, and now you’re actually trying to figure it all out. Well, that’s when we did the conversation with Randy Riemersma, as I talked about. He’s with Span the Chasm. Definitely follow him, he’s a card. I told you I found him on LinkedIn when I was educating myself. He had a video out there and it was literally about stop making this mistake. He just got out of a meeting, I guess, he was in his car or walking towards his car, and I saw it and I was like, he nailed in 90 seconds, exactly what I see over and over again. I’ve lived it, my reps live it, I get it. I reached out to him and connected. That’s how you should be using LinkedIn to grow your network, guys.

Don’t be just sitting there in awe and watching people. No, reach out and connect with them. And then if you connect with them, reach out the next step and say, let’s have a live call. He was talking about the whole disco process, right, discovery and how that can be a real pain in the arse. And in his conversation, it was really about the fact that you’ve got to know that you’re gonna screw up, so you need to take time to get better at your skills. Give yourself permission, first off. You’ve gotta be prepared. So, if you’re gonna have a discovery session with so-and-so, if you have your discovery session with me, you better know everything about me and my company and my challenges. If you are not prepared, you will lose this one and only chance to have a discovery call with us. So, that’s the big thing.

He and I then went and talked about various frameworks. He’s got a variety of frameworks, he recommended it. But it reminded me of the framework that I use that works so much and what the framework was that I use is called SPICED. So, if Jason Bay talked about REPLY, remember that was results, empathy, personalization, laser focus, and you, when you’re writing emails, SPICED is all about discovery. So, SPICED is what you want to drill down and say, what’s your situation, S. What pain is that causing you, right, and you’re looking for stuff you can measure, that’s demonstrable. Here’s where it gets really important, what impact is that having.

Again, more numbers, all right. What critical event is on the horizon that if you don’t address this, you’re gonna be snookered. So, that’s huge. And then, what’s the date you need this resolved for and that’s the other part. So, what you’re really playing on when you do this discovery session, is you’re trying to pull out of them emotions. You want them to be passionate. Numbers, so that you can physically actually measure stuff and show how you an improve upon the numbers, either the numbers for the challenges they’re having or numbers for what they want to achieve. And then goals, if I can get a solution that gets me here, then I’m in a winning position.

So it’s all about asking questions and talking way less than you’re listening. That are evoking emotions, numbers and goals. I use the framework SPICED. The next thing is you don’t wanna ask open-ended questions, I mean closed-end questions. You want to ask open-ended questions. How is that impacting you? There you go, it’s open-ended. And you want to let them talk. You’re excited to say, “Oh I hear you have this pain, “my problem can fix that.” Don’t. Let them finish their spiel. When they’re done everything, then you can go back and say, “We can help you with that. “We have these features. “Let me get myself together. “I’ll prepare a counter response. “I’ll come back to you. “Let’s schedule the next call now “and I’ll tell you how I can fix it all.” That’s the discovery session, episode 48. Emotions, numbers and goals with Randy Riemersma.

And rounding it out, I mentioned it already, I love this one. It was with Mike Weinberg,, multi best-selling author, world extraordinary sales trainer and coach. The man is a genius. He’s one of the original founders of the OutBound Conference. We talked about five keys to creating new opportunities. This was actually documented in his Sales Truth book, #SalesTruth. You’re gonna think some of these things are pretty soft and some of them are. He talks about you have the have the right attitudes. What this really means is mindset. You have to be prepared for failure. You have to be prepared for highs and lows. You have to be prepared that you can help them and if they reject you, it’s not on you, it’s on them. Move it along. So, the right attitude.

So, the next thing was intentional calendar management. You need to be able to block time to do your activities and you protect those. You do not let anybody else usurp that time for you. And, further, you want to put your activity time, when you’re best at your game. So, if you’re a morning person, put it in the morning. Or maybe you need to do some in the morning, some in the afternoon, but be self aware. Also, book time to do what you need to do beyond selling. You need to be on social.

You need to be doing maybe content creation. Book time. You need to own your time. Next thing he talks about is strategic targeting. In other words, know the sweet spot you can win. Know who your ideal customer profile is and relentlessly pursue them. Don’t go astray. Don’t react to the shiny object. Say no to it all. Only focus on the targets you know you can win and you can succeed and you can make an impact and you can close the deal on. Next one, compelling messaging. Don’t be wishy-washy. Know your value props. If you don’t know it, talk to those around you who are having success, but know the messages, know how to deflect, know how to frame the conversation, know how you’re different, know your scripts, if you will, in the end.

Finally, and this is the biggest part, it kinda goes back to the right attitude, the very beginning, the mindset. A commitment to prospecting. So, you have to be very intentional and say, “I know, I’ve gotta prospect. “Maybe I’m the rockstar here at the company, “maybe I’m making a million dollars a year, “I still need to prospect. “I got lots of leads coming in to me from marketing. “Wonderful. “I still need to prospect.” You own your results. That means you commit to prospecting. You do those five things and you’re gonna create massive volume of new opportunities. So, there you have it in a nutshell.

We’ve talked nonstop about five episodes that really resonated with me throughout 2019, from the very, very start where you’re physically investing in yourself to learning, to how to send the proper email, to how to make the right cold call, to physically how to do the right discovery process, to finally, how to have the right skills and attributes for you personally to be a killer, rockstar salesperson. Okay. If you liked that, go follow all those people. Go listen to the podcasts. If you liked that, share this podcast with your colleagues. If you liked that, tell me you liked it. Reach out on LinkedIn. Send me a message. I’d love to hear from you.

But with that, I think I’m through the time. I think I did it. I think I got through me talking all by myself. Hopefully I didn’t bore you. Hopefully you didn’t go fast forward. I apologize about that, but if you got value out of that, awesome. I had fun, this show was amazing. You guys make it awesome. Thank you for being part of my tribe. 2020’s gonna be killer. I’m looking forward to it. I’m getting all ramped up, back into the swing of things. Hitting the road shortly. Amazing speakers coming soon. Don’t go away, there’s more of this amazing content coming to you. In the meantime, thanks for joining me today, folks. My name is Darryl Praill. I am with Inside Inside Sales.