The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 1 year ago

192: The Holiday Mailbag - Sales Hacker Style


In the final episode of the Sales Hacker Podcast for 2021, Sam Jacobs digs into the “mailbag” of great questions found in the Sales Hacker Community. Join us for holiday cheer and some great new ways to look at how you can excel at sales in 2022.

What You’ll Learn 

  1. Do sequences actually work?
  2. How to create a high performing sales team.
  3. Sam’s method for managing 1-on-1s
  4. Managing a role change for an underperforming sales manager
  5. Creating scaffolding images for your future projects and growth 

Show Agenda and Timestamps 

  1. One off emails vs sequences[3:18]
  2. Creating a high performance sales team [6:32]
  3. The importance of filling up sales days for all team members and creating a winning culture [7:09]
  4. Sam’s method for managing 1-on-1s [10:22]
  5. Managing to “want the red bicycle”[14:25]
  6. Sam’s piece of advice for 2021 and into 2022 [17:31]

One, two, one, three, three. Hey everybody in Sam Jacobs. Welcome to the sales soccer podcast. This is our last episode for the year, for two thousand and twenty one, and we're going to do something a little different and we'll see how it goes because it's the first time wherever doing it. We're going to take some questions from the salesacker community and I'm alone here, so I'm just going to be riffing for a fifteen to twenty minutes and then will let you go on your way. But we're going to be answering questions from the salesacer community really on everything related to sales, everything related to the functions that are important sales, which is sales development and account executives, and maybe a few tips and pointers for how to close out the year strong from yours truly. So we will see. If it's absolutely horrible, don't worry, it'll be over soon and if you love it, great, let us know and maybe we'll do this again at some point. But this will be the last episode. We'll take a break until two thousand and twenty two and then after that will of course come back with you regularly scheduled programming. So should be interesting. Stay with us, you'll be able to listen in on all of the ADLIBS that may or may not happen over the next fifteen minutes. Now, before we get to the show, we've got a couple sponsors, three in fact. The first sponsor for the show is pavilion. Pavilion is the key to getting more out of your career. Our private membership gives you access to thousands of like minded peers, dozens of courses and schools through Pavilion University and over Onezero Work Books, templates, scrapes and play books to accelerate your development. This December, pavilion is partnering with Ecology to Plant Up to fiftyzero trees and try and remove some carbon from the atmosphere. For every member that joins that's referred by another member, will plant two hundred and fifty trees per person and often will have partners such as incredible companies, including outreach in Loupio, planting another two hundred and fifty tree. So sometimes we'll get as many as five hundred trees for every single person that joins the community. So help us plant fiftyzero trees this holiday season and sign up using a friends referral link. Our second sponsor is outreach. outreaches the first and only engagement and intelligence platform built by revenue innovators for revenue innovators. Outreach allows you to commit to accurate sales forecasting, replace manual processes with real time guidance and unlock actionable customer intelligence that guides you and your team to win more often, traditional tools don't work in a hybrid sales world. Find out why. outreaches the right solution at Click dot outreach. That io forward thirty MPC and finally, vide yard. VIDEYARD is the best way to sell in a virtual world, whether you need to connect with more leads, qualify more opportunities or close more deals. VIDYARDS video messages make it easy record your Webcam, your scream or both to make prospecting videos, follow ups, product Demos and other communications that drive virtual selling. trive vid yard for free by signing up at vidyardcom. Forward slash free. Now let's get to the mail bag and to the questions that have been posted on the sales hacker community. If you haven't signed up for the sales hacker community yet, you might want to go to sales hackercom, you can have conversations just like the one we're about to have with thousands of other like minded professionals. It's a really incredible platform and it is the place from which we sourced these following questions. Now, Connor Morello, Connor Morello, if you're out there, over seven hundred and thirteen people took a look at this question, which was do sequences actually work? Here's what he said. I got an objection in question from a prospect today that I couldn't confidently deliver on. I am not convinced that the concept of a sequence actually works. I drive our statistics on emails and phone call separately and they are kept in different silos when reporting on success. What unbiased statistics can you supply me with that demonstrates that a sequence, sequence or string of emails, phone calls, etc. Are More effective than one off tasks? It's I don't have any data right in front of me, but it's sort of seems to stand to reason, given that there are a quite a few multibillion dollar valuation companies in the sequence space, including outreach, which effectively define...

...the sales engagement space, and it only stands to reason that doing something against. A plan is probably better than just one off emails or one off call. Certainly persistence is going to be more important. This is something I think probably Jeremy Donovan has some amazing insights on. I wonder if he commented on this post and I don't see any comments. But obviously it would seem to me that coordinating your messaging is really, really important, though. The quat the conversations we've had recently, and and you'll hear an episode from a guy named Jason Bay who runs blissful prospecting, what is it about sequences and how do you make sure that they are effective? The traditional sequence, you know, they call it like an eight by eight, I've heard. I've heard somebody call the most common sequence, which is two touches a day over four days. That's a total of eight days or eight at actual eight total touches. There's other people that run a sequence for, you know, three weeks to four weeks. What's the real focus here? I think the real focus is how do you develop messaging that divent, that demonstrates true empathy and that really shows that you understand where your prospector buyers coming from? The problem with sequences isn't that? Everybody's using them. And you know, all all respect to whoever this person was that asked Connor this question, but I don't think sending a one off email or one off phone call has anything to do with success. I think we're a petition does relate to success and everybody, more people than me, have the data on it right in front of them. But I think the real issues personalization and empathy and demonstrating that you understand the buyers problems and that you are coming at it from a perspective where you understand what they're dealing with every day. And so many people these days are not doing that and that's the problem. That's the problem. So when we see, when we see people that are well, I mean, here's the point that I'm trying to make. I get a bunch of emails, I get a bunch of phone calls. So often they're like, hey, did you see my last message? Do you want to follow up? And the last message doesn't have anything of importance. The thing that you'll hear from people that are professional prospectors is every time you interact with your prospect try to give something a value, and I think this guy, Jason Bay. I think he says teach, not take. I think that's one of the things that that he talks about. So that's really the main issue of sequences is that they're so generic and all they are is about you there, about you asking for the meeting. They're not about you giving some kind of insight or some kind of practical piece of knowledge back to your prospect and I think that's the important thing. All right, so I picked one where I didn't have any great data in front of me. But here's a question from a guy named Jordan duty. Jordan says, how do you create a high performing sales team? What is your plan to create a high performing sales team? Answers are always different. So to kickoff, I'd be happy to have the view of other sales leaders. And somebody says this. John Van City says, I think it starts with creating a winning culture, and that is exactly what I was going to say. Now what creates a winning culture? I say, here's what I say. The best way to create a winning sales team is to have a great product. You might not have. That might not be surprised to you and it's pretty straightforward. But when you have product market fit. When you have more opportunities and when your sales teams day is full with meetings, then those meetings, some percentage of those meetings, are going to convert into money. And when those sales people don't have any meetings at all, they are going to be pissed off and frustrated and it's going to be a Shitty, losing culture. So what is the thing ultimately that creates culture? The thing that ultimately creates culture is product market fit. This is somewhat of a controversial opinion. That's why the siren just started going off in the background. I'm in New York City as I record this. Here's what creates a winning culture. Is a great product that people love. Here's the mistake that people make now, and so that's what I now. There are other things. You can fuck it up. You could mess it up if you have a great culture but you have a bunch of jerks running the team and you've designed, perhaps you know, some portion of your compensation philosophy wrong. But but I think it's going to be unlikely. I think culture, specifically a winning culture, is the exhaust of a great product. That's what I think.

When I've been at winning sales teams, and I've been at them sometimes and I'm I've been part of and I've led losing sales teams. And what's the common theme? The common theme is whether the customers actually want the product and whether, I guess, the secondary the follow up point to creating a winning culture is that you have effectively managed capacity. So the other thing that can create a winning culture. I've been at there was one company where I was a chief for evno officer and they'd gone through a period where they had a winning culture and then they had a terrible culture. What was the difference? They had a winning culture when they had a small number of sales people and all of those sales people were all equipped to close deals. They had a losing culture when they hired thirty more sales people, because they had a revenue model that delivered revenue based on how many people you hire, not a waterfall model based on how many opportunities you create and need to hit your revenue targets. So they hired a ton of people, but they didn't have meetings to fill those people's bellies and as a consequence, a bunch of people were sitting around doing nothing. All of a sudden, the sales floor was quiet, everybody was drumming their fingers on their desks and going for walks and it didn't work. So, if you ask me, and if you're thinking, if you're a rep, thinking about how do you evaluate a great team, think what you really want to do, and this is sort of a related question for you. There's so many people that are hiring right now. There's so many people out there, I think, and compensation is way up. So if you're evaluating, you know you're out there in the market and you're evaluating different companies, I think one of the things you want to ask about is quote attainment percentage. Right, how many reps are actually hitting the quota that set, and that should give you some and then maybe the secondary question is how many people they've been hiring recently so you understand. Did they just go you know, have they hired twenty people over the last six months and still it's eighty five percent or ninety percent, or is it just that they've had they've only got four people, but they're about to embark on this big hiring spree because they just raised a shitload of money. So tbd on that. But if you ask me, the way to create a winning culture is to have a great product. And then, of course you do all the other things. You you empower your sellers with craining tools and enablement, you give them all the resources they need to succeed. But fundamentally the main resource of Salesperson needs to succeed, in my opinion, is a bunch of meetings to fill up their day. And if you do that you're going to have a great culture and the thing that will create the meetings is a great product. So, Jordan Doady, thank you for asking that question and we're going to move on to the next one. Coral Armstrong, ask this question one on ones for management or coaching. Do you have a structure or a method? Yes, I do. So this is two things here. So first, I'm a CEO and I manage executive. So what I do, which is not what coral is really asking, but if you if you want a little pro tip, here's the pro tip that I learned from Jesse Hurtzberg, who is my CEO at live stream. Every employee gets a Google Doc. The Google doc is named you plus the employee, oneonone, so you know and you seem my vp of people are doc is salmon and oneon one. Okay, Great. Every week she types in what she wants to talk about and I type and what I want to talk about, but we always do it at the top so that you never have to scroll to the bottom and you type in your notes as you have your one on one. And of course, one of the things that happens as you create an artifact in a document that you confer back to when you're writing reviews and doing things like that. So, first of all, I just think that's a good practice. Now for executives, you know, I sometimes have feedback that I want to give them, but really what I'm focused on is I'm having them tell me what they want to talk about and and having them dictate the agenda, because really I view myself as a resource provider to my team, and so they tell me what they need and where they're coming up against challenges and I try and provide it to them. Now, if you're a REP, here's here's and if you're managing reps, here's my personal philosophy. So I think first of all, every every wrap, every person at your company deserves a weekly oneonone. That's my opinion. Should be forty five minutes to an hour. Okay, Great. Now what do we talk about? I rotate three things. So the first thing is pipeline review, right, but you can't do...

...this every time because because that's not super helpful. But and sometimes you want to do a big pipeline review in front of the bunch of people, but call it pipeline dissection, pipeline review. Right. So that's one, one of the three. Your this is you know, this will happen once every four weeks, right, that because there's three different types of one on ones. The second type of one on one is a sort of a roleplays skill development, so specifically about like some part of the sales process that you feel that REP is working on or struggling with. That's what that's what you talk about in the second one. So the first week is pipeline review and really just trying to understand where they're forecasting for wherever they're going to end up for the quarter of the month or whatever it may be. The second is skill development, focusing on discovery, focusing on asking great question Ustions, focusing on closing, focusing a negotiation, any of those things. And then the third is not related to any of those things. It's really how are they doing? It is really, you know, sort of emotional balance, psychological safety and making sure that they, as human beings, are okay and that they have an opportunity to talk to you about what's going on in their life. And one of the one thing that, you know, we always talk about coral is your manager should know details about your personal life. It doesn't mean that, you know, they need to know everything, everything about your personal life, but managers, you should have a close enough relationship with your reps that you that you understand what your reps are going through, where they are in their life journey, what their goals are, what their motivations are. You know, it's still amazing that you know a lot of sales people are not just motivated by money, but their managers don't know that. If your reps aren't managing or specific reps are not motivated by specifically by money, then a new complant might not be as exciting to them as really giving them another day off so they can deal with a family situation or just understanding if they're having a you know, a mental health crisis or whatever it may be. So that's that's my framework, coral arm strong, for for oneonone's. The first one is pipeline review, the second one is skill development and role play and the third is really just how you doing and making sure that that person feels embraced by the organization, cared for by the organization and that they're doing okay from a personal perspective. All right, a few more questions. How to manage a role change for an underperforming sales manager. So this question as from somebody that has a you've a pseudonym. It's like there's two names here. There's a listed name and then there's like an at name, like a twitter handle. Their handle is George T eighteen one thousand nine hundred and eighty five, but their name is seagulls sale, so maybe they run like some sellemn company called seagulls sale. I'm a leader for a very small team in my first management role. One member the team is underperforming. We like this person. I'm sort of paraphrasing the boss and I have agreed to keep this rep on as an attitude and company fit are good, but a justice role to focus just on Legen meaning make him a nasty are as. This seems to be a strength of this rap. I'm concerned that the REP may be devotivated by this change and e tips on how to manage a change like this. In general, Seagull sale the most the the the vice and the feedback I have for you is if is focused on there's an old saying right, if you got your kid at your child a red bicycle for the holidays, for Hanaker Christmas or Quans or any other seasonal holiday, the trick isn't. The trick isn't to figure out what the kid actually wanted, what your child actually wanted. The trick is to make them believe that they are the ones that wanted the red bicycle. So part of the job of transitioning people into neurals is and is a little bit of inception, as a little bit of leading them, creating a structure so that they can realize that this is the best outcome for them to part of that is is, of course, feedback. Part of it is sometimes that people know that they're struggling, and so sometimes you're surprised when you can create an outcome and, you know, an off ramp for somebody, as long as you do it from a place of compassion and consideration and as long as the emphasis is on, Hey, this is going to be good for you, this is going to be a way for you to succeed and thrive. Maybe we put you into this role too soon. So maybe this is an opportunity for you to really play to your strengths, to reduce the pressure a little bit, because the other thing that happens, and and some reps understand or don't understand, is that there's there's...

...more pressure as a closing reps. a closing rep, if you consistently don't hit your number, can't get to where you need to get to in terms of quota attainment, you will get fired, and SDRs get fired too, but not at really the same rate. And so one of the things that you can say to this person, Mr Seagull sale or Mrs Seagull Sale, or Miss segull sale or they seegull sale, really your gender is not important to the to the my advice here. The advice is, Hey, let's reduce the pressure on you so that you can really develop at the right speed. Your compensation is not going to change. You're going to get to focus on the things that are important to you, that you're actually really really good at and we can create a longer ramp time effectively for you at this company so that you can grow into the other skills that you'll want to develop over time without having so much pressure that it ultimately impacts your ability to even be here at all. I think that's a really compassionate message and I think that that that people can respond to that, especially because, seagull sale, you mentioned that you're not really changing their compensation. So this might help the other reps because this person is moving into Lee generation and creating new opportunities, and might help them because they're doing something that they're getting good at and, at the reducing the likelihood that they actually have to leave the company. So that's my advice to you. Now we were almost at the end of our time together. So what's my last piece of advice? What we are at the end of the year right it's two thousand and twenty one. So what's my piece of advice as we think about reflecting on two thousand and twenty one and looking ahead to two thousand and twenty two? Here's one last piece of advice. We do this exercise at Pavilion on the executive team. I do it personally, and I just actually taught this practice to a group of people that are taking our rising executive program and it's all about a visioning, visioning right, manifesting the future. So here's the deal. You're going to set your goals for two thousand and twenty two, and the problem with how you do it initially is that you're going to present your goals definitionally as theoretical. I hope that I will. I hope that I will write in two thousand and twenty one, my goal is to my goal is to achieve this outcome. My goal is to make a million dollars in sales. My goal is to become, go to the president's Club. All of those things. The way that you're phrasing them literally, the way that you're saying those words, you're putting them into the future and implicitly making them theoretical. You're implicitly making them questionable, probabilistic fantasy. See Right, my goal is too means that it hasn't happened yet. By definition, my goal is to is to get to President's club, meaning you're not a president's club. That's how you've structured that sentence. Instead, try this, try a different practice. Put yourself in the future. Twelve months you're in December of two thousand and twenty two, and instead of looking ahead to two thousand and twenty three, you're looking back on two thousand and twenty two. And so you start off this little paragraph, for page or two pages or however many pages it is that you want to write, and you say, I'm so happy and grateful, I'm so happy and grateful that last year was amazing. I'm sitting here in front of a roaring fireplace and lake placid, New York, and I just went snowshoeing with my kids or with my wife or my girlfriend or my husband or my partner, or I'm alone, because I prefer to be alone. And you don't have to be in a couple to be happy. Fine, you're alone, I don't care where you are. The point is, this is your image. So you you don't have to do any of these things. But what are we doing when I say it like that? So first thing, I'm grounding it, I'm it's making it real. I'm in a real place, I'm putting details in the picture right, I'm hanging plants and I'm lighting lamps and I'm putting things on the table and I'm hanging a picture. I'm making it real, I'm imagining what it's really like, and then I'm reflecting backwards as if I've already accomplished it, so that it is not theoretical, it is actually already happened. I'm so happy and grateful that I'm sitting here in December of two thousand and twenty two, and man what a year it was, though. Fire is roaring, I'm in Lake Placid, New York. I B I'm myself because I don't need other people to be happy, but I really did an amazing job. I actually went to President's Club two months ago. We all flew off to Hawaii. I did that because I...

...was the top seller in the organization. I actually crushed my quota. In Two thousand and twenty one I did eight hundred thousand dollars in sales, and this year I did one point two five million in sales. How did I do it? Well, here's how I did it. I did it through preparation by bout buddy, bout it, and off you go. And here's the point. You are first of all putting real structural details. We call those scaffolding, images the roaring fire. What does it smell like? You know, what are you eating? What Book Are you reading? What are you watching? I'm re watching succession for the fifteen time. You're so you really feel like you're there, and then you're reflecting back on accomplishments that have already happened, as opposed to making them theoretical. So, and I will tell you quick final note before we head into the holidays. I did this a year ago and and I talked about how and and I had I put it into the future, I'd said, in December of two thousand and twenty one. I'm so happy and grateful. I'm on a boat, I'm welling, I'm wearing my villa Breckin swim trunks and I am reading my book and Music's playing and the dogs are here and I'm on a boat and I'm on a boat with my wife and I'm so happy and grateful because we closed a massive twenty five million dollar financing and this is how it was structured and this is how it went down. And so I did all of that. I did all of that and I had assumed that the you know, the reason I needed to have that a. The deal close in October of two thousand and twenty one was because the company, Pavilion, the company that I run, wouldn't be big enough by the time right to do it any sooner. But I constructed this whole image about the specific type of financing event. Twenty five million was the number. I was on a boat. It was beautiful. Well, in February of two thousand and twenty one I got an email from Peter Fowl and at elephant ventures and in April we close to twenty five million dollar financing. And actually not in not in December, but in August and September I was on a boat with my wife. The dogs were not there, but a lot of other friends were and we were celebrating this amazing event. And it all happened not exactly but very, very close, eer really close, weirdly close to how I would writ how I had written it when I was out at the beach by myself in Mont talk in the week between Christmas and New Year's in December of two thousand and twenty so I did it again for two thousand and twenty one. This time it's talking about how great pavilion is and all the great things were going to do and I could read it to you some other time, but this is a salesacker podcast and at the billion podcast. But the point is that try visioning. Try visioning, create scaffolding images, put yourself in the scene and then look backwards as opposed to looking forwards, because looking backwards means it is already happened and looking forwards makes it theoretical. Okay, all right, everybody. It's been an incredible year. I hope you've had a great year. It's been a lot of challenges. We may even be going back into another covid wave, but just stay strong, stay happy, tell your loved ones that you love them. I hope that you're with loved ones. Make sure that you do good things for other people. Try to find something every day that's not about you but about somebody else, that you'll find that it nourishes your soul and it feel. You'll also find that it pays dividends to you over the course of your career. But really, just try and be be good and have fun and enjoy yourself and be optimistic about the future, because optimism creates further optimism and abundance be gets abundance. And that's the show. That's the show and I really appreciate everybody listening. We got all of those questions from the salesacker community. So if you if you're not a member yet, you're missing out. Any sales professional can join as a member to ask questions, get immediate answers and share experiences with likeminded sales professionals. Jump in and start a discussion with more than seventeenzero professionals at sales hackercom. Of course, we want to thank our sponsors. The first is pavilion. Help US plant fiftyzero trees this holiday season. Sign up for pavilion using a friends referral link by December thirty one, of course. Also thinking outreach, the only engagement and intelligence platform built by revenue innovators for revenue innovators. Check out outreach at click dot outreach, dooh forward, thirty MPC. And finally, Bideyard, the best way to sell in a virtual world. Try vidyard for free by signing up at vidyardcom. Forward, slash free. I want to thank the team here that puts on the salesacker podcast. Samantha Hembury does a really amazing job. Rob...

Conlin over at sweet fish media. Thank you for all of your help and support. Thank you to all of our sponsors, everybody, from vidyard to ambition, to outreach, to pavilion to so many more amazing companies, Blue Board, all of you out there that have supported the salesacker podcast, we really, really appreciate it. Please consider giving us five stars and without that, with that, not without that, but with that again, try to try to take some time away from work, try to get some downtime, try to be with some loved ones, get some sleep, get some rest, but also have a few nights where you don't get any sleeper, get any respier, out there having fun, don't get covid wear. I'm asked, I will talk to everybody in two thousand and twenty two. Happy in year everybody.

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