The Sales Hacker Podcast
The Sales Hacker Podcast

Episode · 1 month ago

192: The Holiday Mailbag - Sales Hacker Style

ABOUT THIS EPISODE

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 twentyone, and we're going to do something a little different and we'll see howit goes because it's the first time wherever doing it. We're going to takesome questions from the salesacker community and I'm alone here, so I'm just goingto be riffing for a fifteen to twenty minutes and then will let you goon your way. But we're going to be answering questions from the salesacer communityreally on everything related to sales, everything related to the functions that are importantsales, which is sales development and account executives, and maybe a few tipsand pointers for how to close out the year strong from yours truly. Sowe will see. If it's absolutely horrible, don't worry, it'll be over soonand if you love it, great, let us know and maybe we'll dothis 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 willof 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 ADLIBSthat may or may not happen over the next fifteen minutes. Now, beforewe 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 togetting more out of your career. Our private membership gives you access to thousandsof like minded peers, dozens of courses and schools through Pavilion University and overOnezero Work Books, templates, scrapes and play books to accelerate your development.This December, pavilion is partnering with Ecology to Plant Up to fiftyzero trees andtry and remove some carbon from the atmosphere. For every member that joins that's referredby another member, will plant two hundred and fifty trees per person andoften will have partners such as incredible companies, including outreach in Loupio, planting anothertwo hundred and fifty tree. So sometimes we'll get as many as fivehundred trees for every single person that joins the community. So help us plantfiftyzero trees this holiday season and sign up using a friends referral link. Oursecond sponsor is outreach. outreaches the first and only engagement and intelligence platform builtby revenue innovators for revenue innovators. Outreach allows you to commit to accurate salesforecasting, replace manual processes with real time guidance and unlock actionable customer intelligence thatguides you and your team to win more often, traditional tools don't work ina hybrid sales world. Find out why. outreaches the right solution at Click dotoutreach. That io forward thirty MPC and finally, vide yard. VIDEYARDis the best way to sell in a virtual world, whether you need toconnect with more leads, qualify more opportunities or close more deals. VIDYARDS videomessages make it easy record your Webcam, your scream or both to make prospectingvideos, 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 postedon the sales hacker community. If you haven't signed up for the sales hackercommunity yet, you might want to go to sales hackercom, you can haveconversations just like the one we're about to have with thousands of other like mindedprofessionals. It's a really incredible platform and it is the place from which wesourced these following questions. Now, Connor Morello, Connor Morello, if you'reout 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 gotan 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 driveour statistics on emails and phone call separately and they are kept in different siloswhen reporting on success. What unbiased statistics can you supply me with that demonstratesthat 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 rightin 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 sequencespace, including outreach, which effectively define...

...the sales engagement space, and itonly stands to reason that doing something against. A plan is probably better than justone off emails or one off call. Certainly persistence is going to be moreimportant. This is something I think probably Jeremy Donovan has some amazing insightson. I wonder if he commented on this post and I don't see anycomments. But obviously it would seem to me that coordinating your messaging is really, really important, though. The quat the conversations we've had recently, andand 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 areeffective? The traditional sequence, you know, they call it like an eight byeight, 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 eightdays or eight at actual eight total touches. There's other people that run a sequencefor, you know, three weeks to four weeks. What's the realfocus here? I think the real focus is how do you develop messaging thatdivent, that demonstrates true empathy and that really shows that you understand where yourprospector 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 askedConnor this question, but I don't think sending a one off email or oneoff phone call has anything to do with success. I think we're a petitiondoes relate to success and everybody, more people than me, have the dataon it right in front of them. But I think the real issues personalizationand empathy and demonstrating that you understand the buyers problems and that you are comingat 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. Iget a bunch of emails, I get a bunch of phone calls. Sooften they're like, hey, did you see my last message? Do youwant 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 youinteract with your prospect try to give something a value, and I think thisguy, Jason Bay. I think he says teach, not take. Ithink that's one of the things that that he talks about. So that's reallythe main issue of sequences is that they're so generic and all they are isabout you there, about you asking for the meeting. They're not about yougiving some kind of insight or some kind of practical piece of knowledge back toyour prospect and I think that's the important thing. All right, so Ipicked one where I didn't have any great data in front of me. Buthere's a question from a guy named Jordan duty. Jordan says, how doyou create a high performing sales team? What is your plan to create ahigh performing sales team? Answers are always different. So to kickoff, I'dbe 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 createsa winning culture? I say, here's what I say. The best wayto create a winning sales team is to have a great product. You mightnot 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 whenyour sales teams day is full with meetings, then those meetings, some percentage ofthose meetings, are going to convert into money. And when those salespeople don't have any meetings at all, they are going to be pissed offand frustrated and it's going to be a Shitty, losing culture. So whatis the thing ultimately that creates culture? The thing that ultimately creates culture isproduct market fit. This is somewhat of a controversial opinion. That's why thesiren just started going off in the background. I'm in New York City as Irecord this. Here's what creates a winning culture. Is a great productthat people love. Here's the mistake that people make now, and so that'swhat I now. There are other things. You can fuck it up. Youcould mess it up if you have a great culture but you have abunch of jerks running the team and you've designed, perhaps you know, someportion of your compensation philosophy wrong. But but I think it's going to beunlikely. I think culture, specifically a winning culture, is the exhaust ofa 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 andI've led losing sales teams. And what's the common theme? The common themeis whether the customers actually want the product and whether, I guess, thesecondary the follow up point to creating a winning culture is that you have effectivelymanaged capacity. So the other thing that can create a winning culture. I'vebeen at there was one company where I was a chief for evno officer andthey'd gone through a period where they had a winning culture and then they hada terrible culture. What was the difference? They had a winning culture when theyhad a small number of sales people and all of those sales people wereall equipped to close deals. They had a losing culture when they hired thirtymore sales people, because they had a revenue model that delivered revenue based onhow many people you hire, not a waterfall model based on how many opportunitiesyou create and need to hit your revenue targets. So they hired a tonof people, but they didn't have meetings to fill those people's bellies and asa consequence, a bunch of people were sitting around doing nothing. All ofa sudden, the sales floor was quiet, everybody was drumming their fingers on theirdesks and going for walks and it didn't work. So, if youask me, and if you're thinking, if you're a rep, thinking abouthow 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 manypeople that are hiring right now. There's so many people out there, Ithink, and compensation is way up. So if you're evaluating, you knowyou're out there in the market and you're evaluating different companies, I think oneof 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 giveyou some and then maybe the secondary question is how many people they've been hiringrecently so you understand. Did they just go you know, have they hiredtwenty people over the last six months and still it's eighty five percent or ninetypercent, 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 ashitload of money. So tbd on that. But if you ask me, theway to create a winning culture is to have a great product. Andthen, of course you do all the other things. You you empower yoursellers with craining tools and enablement, you give them all the resources they needto succeed. But fundamentally the main resource of Salesperson needs to succeed, inmy opinion, is a bunch of meetings to fill up their day. Andif you do that you're going to have a great culture and the thing thatwill create the meetings is a great product. So, Jordan Doady, thank youfor 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 thisis 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 protip 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 plusthe employee, oneonone, so you know and you seem my vp of peopleare doc is salmon and oneon one. Okay, Great. Every week shetypes in what she wants to talk about and I type and what I wantto talk about, but we always do it at the top so that younever have to scroll to the bottom and you type in your notes as youhave your one on one. And of course, one of the things thathappens as you create an artifact in a document that you confer back to whenyou're writing reviews and doing things like that. So, first of all, Ijust 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'mfocused on is I'm having them tell me what they want to talk about andand having them dictate the agenda, because really I view myself as a resourceprovider to my team, and so they tell me what they need and wherethey'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'smy personal philosophy. So I think first of all, every every wrap,every person at your company deserves a weekly oneonone. That's my opinion. Shouldbe forty five minutes to an hour. Okay, Great. Now what dowe 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 notsuper helpful. But and sometimes you want to do a big pipeline review infront of the bunch of people, but call it pipeline dissection, pipeline review. Right. So that's one, one of the three. Your this isyou know, this will happen once every four weeks, right, that becausethere's three different types of one on ones. The second type of one on oneis a sort of a roleplays skill development, so specifically about like somepart of the sales process that you feel that REP is working on or strugglingwith. That's what that's what you talk about in the second one. Sothe first week is pipeline review and really just trying to understand where they're forecastingfor wherever they're going to end up for the quarter of the month or whateverit may be. The second is skill development, focusing on discovery, focusingon asking great question Ustions, focusing on closing, focusing a negotiation, anyof those things. And then the third is not related to any of thosethings. It's really how are they doing? It is really, you know,sort of emotional balance, psychological safety and making sure that they, ashuman beings, are okay and that they have an opportunity to talk to youabout 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 detailsabout your personal life. It doesn't mean that, you know, they needto know everything, everything about your personal life, but managers, you shouldhave a close enough relationship with your reps that you that you understand what yourreps are going through, where they are in their life journey, what theirgoals are, what their motivations are. You know, it's still amazing thatyou know a lot of sales people are not just motivated by money, buttheir managers don't know that. If your reps aren't managing or specific reps arenot motivated by specifically by money, then a new complant might not be asexciting to them as really giving them another day off so they can deal witha family situation or just understanding if they're having a you know, a mentalhealth crisis or whatever it may be. So that's that's my framework, coralarm strong, for for oneonone's. The first one is pipeline review, thesecond one is skill development and role play and the third is really just howyou doing and making sure that that person feels embraced by the organization, caredfor by the organization and that they're doing okay from a personal perspective. Allright, a few more questions. How to manage a role change for anunderperforming sales manager. So this question as from somebody that has a you've apseudonym. It's like there's two names here. There's a listed name and then there'slike an at name, like a twitter handle. Their handle is GeorgeT eighteen one thousand nine hundred and eighty five, but their name is seagullssale, so maybe they run like some sellemn company called seagulls sale. I'ma leader for a very small team in my first management role. One memberthe team is underperforming. We like this person. I'm sort of paraphrasing theboss and I have agreed to keep this rep on as an attitude and companyfit are good, but a justice role to focus just on Legen meaning makehim 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 tipson how to manage a change like this. In general, Seagull sale the mostthe the the vice and the feedback I have for you is if isfocused on there's an old saying right, if you got your kid at yourchild a red bicycle for the holidays, for Hanaker Christmas or Quans or anyother seasonal holiday, the trick isn't. The trick isn't to figure out whatthe kid actually wanted, what your child actually wanted. The trick is tomake them believe that they are the ones that wanted the red bicycle. Sopart of the job of transitioning people into neurals is and is a little bitof inception, as a little bit of leading them, creating a structure sothat they can realize that this is the best outcome for them to part ofthat is is, of course, feedback. Part of it is sometimes that peopleknow that they're struggling, and so sometimes you're surprised when you can createan outcome and, you know, an off ramp for somebody, as longas you do it from a place of compassion and consideration and as long asthe 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 anopportunity for you to really play to your strengths, to reduce the pressure alittle bit, because the other thing that happens, and and some reps understandor 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 towhere you need to get to in terms of quota attainment, you will getfired, 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 seegullsale, 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 thatyou 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 toyou, that you're actually really really good at and we can create a longerramp time effectively for you at this company so that you can grow into theother skills that you'll want to develop over time without having so much pressure thatit ultimately impacts your ability to even be here at all. I think that'sa 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 theircompensation. So this might help the other reps because this person is moving intoLee generation and creating new opportunities, and might help them because they're doing somethingthat they're getting good at and, at the reducing the likelihood that they actuallyhave to leave the company. So that's my advice to you. Now wewere almost at the end of our time together. So what's my last pieceof advice? What we are at the end of the year right it's twothousand and twenty one. So what's my piece of advice as we think aboutreflecting on two thousand and twenty one and looking ahead to two thousand and twentytwo? Here's one last piece of advice. We do this exercise at Pavilion onthe executive team. I do it personally, and I just actually taughtthis practice to a group of people that are taking our rising executive program andit's all about a visioning, visioning right, manifesting the future. So here's thedeal. 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 topresent your goals definitionally as theoretical. I hope that I will. I hopethat I will write in two thousand and twenty one, my goal is tomy goal is to achieve this outcome. My goal is to make a milliondollars 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, theway that you're saying those words, you're putting them into the future and implicitlymaking 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 apresident'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 inDecember of two thousand and twenty two, and instead of looking ahead to twothousand 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 howevermany 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 wasamazing. 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 wifeor my girlfriend or my husband or my partner, or I'm alone, becauseI prefer to be alone. And you don't have to be in a coupleto 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 haveto do any of these things. But what are we doing when I sayit like that? So first thing, I'm grounding it, I'm it's makingit 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 thetable and I'm hanging a picture. I'm making it real, I'm imagining whatit'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'mso happy and grateful that I'm sitting here in December of two thousand and twentytwo, 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'tneed 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 offto 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 dideight hundred thousand dollars in sales, and this year I did one point twofive million in sales. How did I do it? Well, here's howI did it. I did it through preparation by bout buddy, bout it, and off you go. And here's the point. You are first ofall 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 successionfor the fifteen time. You're so you really feel like you're there, andthen you're reflecting back on accomplishments that have already happened, as opposed to makingthem theoretical. So, and I will tell you quick final note before wehead into the holidays. I did this a year ago and and I talkedabout 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 trunksand I am reading my book and Music's playing and the dogs are hereand I'm on a boat and I'm on a boat with my wife and I'mso happy and grateful because we closed a massive twenty five million dollar financing andthis is how it was structured and this is how it went down. Andso I did all of that. I did all of that and I hadassumed 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 timeright to do it any sooner. But I constructed this whole image aboutthe specific type of financing event. Twenty five million was the number. Iwas on a boat. It was beautiful. Well, in February of two thousandand twenty one I got an email from Peter Fowl and at elephant venturesand in April we close to twenty five million dollar financing. And actually notin not in December, but in August and September I was on a boatwith my wife. The dogs were not there, but a lot of otherfriends were and we were celebrating this amazing event. And it all happened notexactly but very, very close, eer really close, weirdly close to howI would writ how I had written it when I was out at the beachby myself in Mont talk in the week between Christmas and New Year's in Decemberof two thousand and twenty so I did it again for two thousand and twentyone. This time it's talking about how great pavilion is and all the greatthings 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 thepoint is that try visioning. Try visioning, create scaffolding images, put yourself inthe scene and then look backwards as opposed to looking forwards, because lookingbackwards 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 hada great year. It's been a lot of challenges. We may even begoing 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 tofind something every day that's not about you but about somebody else, that you'llfind that it nourishes your soul and it feel. You'll also find that itpays dividends to you over the course of your career. But really, justtry and be be good and have fun and enjoy yourself and be optimistic aboutthe future, because optimism creates further optimism and abundance be gets abundance. Andthat's the show. That's the show and I really appreciate everybody listening. Wegot all of those questions from the salesacker community. So if you if you'renot a member yet, you're missing out. Any sales professional can join as amember to ask questions, get immediate answers and share experiences with likeminded salesprofessionals. Jump in and start a discussion with more than seventeenzero professionals at saleshackercom. Of course, we want to thank our sponsors. The first ispavilion. Help US plant fiftyzero trees this holiday season. Sign up for pavilionusing a friends referral link by December thirty one, of course. Also thinkingoutreach, the only engagement and intelligence platform built by revenue innovators for revenue innovators. Check out outreach at click dot outreach, dooh forward, thirty MPC. Andfinally, 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. SamanthaHembury 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 ofour sponsors, everybody, from vidyard to ambition, to outreach, to pavilionto so many more amazing companies, Blue Board, all of you out therethat have supported the salesacker podcast, we really, really appreciate it. Pleaseconsider giving us five stars and without that, with that, not without that,but with that again, try to try to take some time away fromwork, try to get some downtime, try to be with some loved ones, get some sleep, get some rest, but also have a few nights whereyou 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 twothousand and twenty two. Happy in year everybody.

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