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#613: Master Parallel Selling Strategies to Speed Up Every Deal | Sam Mckenna | 30MPC Hall of Fame

from 30 Minutes to President's Club | No-Nonsense Sales

31m 57s

#613: Master Parallel Selling Strategies to Speed Up Every Deal | Sam Mckenna | 30MPC Hall of Fame

Sam McKenna, a top sales leader and founder of Sam Sales, emphasizes a fundamental shift in outbound sales: from cold calling to warm, relationship-based prospecting using network data. She highlights that understanding a buyer’s decision process—whether they present, ask, or tell the board—is essential for anticipating pushback and preparing for tough questions. A key strategy is parallel processing, where sales teams initiate cross-functional engagement (procurement, legal, CS) early and simultaneously, rather than waiting for sequential approval. This builds momentum and accelerates deal timelines. She advises sellers to identify key influencers, competitors, and internal stakeholders to gain deeper insights. By asking open-ended, uncomfortable questions—especially those buyers don’t know the answers to—sales professionals uncover hidden concerns and foster trust. Early actions like NDAs or demos trigger internal reviews and create visibility. Recurring meetings and proactive coordination with internal teams maintain momentum. Crucially, she warns against sending calendar links in emails, as it’s presumptuous and undermines buyer autonomy. Ultimately, top performers don’t just close deals—they close them faster by building relationships, anticipating objections, and working across functions from day one.

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Sellers cold outpound socks for both you and your prospect. It takes an insane amount of effort. Reply rates are in the tank and you are fishing in the same pond as everybody else. I literally wrote a book on cold calling, but Sam McKenna, who's the CEO of #SamSales, completely changed my mind about what I thought social-selling and great outbound prospecting is. Sam literally has broken 13 national sales records. She was recruited by LinkedIn because she was so good at LinkedIn sales navigator and she built her business from scratch into a multi-million dollar business using exactly what she teaches in her social-selling course that she built in partnership with 30MPC. Go to 30MPC.com/Sam and her new course teaches you how to use relationship data and your network's network to get warm introductions into your dream accounts that would never answer your cold call, respond to your cold email, or open the gift that you sent to their office. If you go to 30MPC.com/Sam, we are giving away all of Sam's favorite LinkedIn sales now, reports, alerts, and scripts that you can use to break into more accounts with less effort. Over the next four weeks, everything 30MPC is dropping is going to be focused on either social-selling or one of our best ever Sam McKenna episodes. And the reason for that is, at the end of the month, we are launching our social-selling course with Sam. Today's episode is one of my favorites with her. We talk about parallel-selling strategies to move you deals faster and create momentum in them. I hope you enjoyed the episode. If you want to pre-order Sam's course, you can do that in the show notes. Enjoy the episode. Good morning, everybody, and welcome to this episode of 30 Minutes to President's Club. My name is Armand Froke, and I'm here with my co-host, Nixie Gelski. Like today, we have around two, with the one and only founder of Sam Sales. It's Sam McKenna. Nick, why should people listen? So Sam has some phenomenal stuff around parallel processing next steps in deals, how you should be thinking about getting to power and involving multiple parties, both very early in the deal, but also late stage to accelerate the vendor review process so you are not stuck trying to get a contract signed on New Year's Eve. This was a very good one, Armand. Three, two, one. Let's roll. Welcome to the show. We start every single episode with your top three action and we'll take away, so let's get your three. All right. Thanks for having me. Let's talk about first, are they presenting, asking, or telling, who are we talking about? This is something we're talking about when we're specifically talking to a buyer that says, hey, we're going to go in front of a board, and we're going to talk about your deal, right? So we can't get your deal done until we present to the board, that's going to happen in a couple of months. We'll let you know after that happens. Most people say, okay, that's great. You know, nothing I can do until then, that's it. But here's the thing. You've got to think about what is actually going to happen when that person goes in front of the board. So one of the uncomfortable questions you have to think about when you're asking your buyer about this deal is number one, are you going to be presenting, telling, or asking the board for permission? Are they presenting and waiting for feedback? Are they asking for permission to spend money with you? Or are they saying, hey, this is what we're going to do? That's a key differentiator in thinking about how your deal is going to move forward. And then on top of that, really quick, has this person presented a deal of this kind to the board before? Is there pushback? Are there questions that usually come up? Is there something that you can help them prepare for? Because if this is the first time they're doing it and they're presenting, not asking or telling, you're going to be in for a different story for your deal, then you probably thought. What's number two? Number two, thinking about parallel processing with procurement. So let's say for the same deal, person comes back to you and says, there's nothing we can do. So let's say it's August and we can't do anything until this presentation happens in December. Great. Let's start talking about curin. Can we get in front of procurement and get our MSA done? Can we go and do red lines? Can we understand how they buy what the processes are? What stamps we need? What bind thresholds happen? Can we do all of that? And the buyer says we could, except we don't have approval yet to move forward. We won't have until the board meeting happens. And because procurement is outsourced, we can't do anything with them until we have these levels of approval internally. So again, most reps would say nothing we can do. We can't touch procurement until then. So two things I would tell you to do here. Number one, make sure you have the meeting scheduled with procurement directly after that presentation happens, right? There's absolutely no harm in getting the meeting scheduled. Not only will this help you make sure that you get on their calendar now before everybody else is trying to do it, but make sure that you get on your own legal and procurement teams calendar right now, again, before everybody is rushing. The second thing asked for a standard MSA, you've done this before buyer presumably, right? So what are non-negotiables? What do you guys never agree to? Do you have net 45 terms, net 16, net 90? Do you only do litigation in Delaware, Texas, California? What does that look like? Because here's the thing, whatever they want, we're not going to ultimately agree to. We're going to have to go through our own legal procurement, rev-up, sales apps to get certain things done. So do that all in advance and have all that documentation ready and the meeting scheduled way before you ever nature. Round us out, Sam. What's number three? All right. Let's think about who are the VAs. Now the grammatically incorrect sentence makes a lot of sense. So I want you to think about whether you are leader or whether you are a rep. Every single time you hear the word "they" from your rep or from your buyer, you want you to ask yourself, do you know who is in that day? Is it they, the competition you have, is it they, the buying circle, is it they, the influencing committee, who are the days? Because I think about every time I've heard that from a buyer, the buyer says, hey, we're going to look at this proposal, we're going to take it back to the team, and then they're all going to decide together. And I say, that sounds great, thanks. What I really need to say is, that's awesome. Do you know who's in that buying committee, who makes up those days? And I ask, because I wonder if part of those are people who have been our clients before, they have mutual connection with our executive team, if they've worked with our CS team before, if you buyer are serious about working with us, tell us who those days are, because man, we'll be able to figure out who they know what experience they have and help this deal move along. Same thing on the competition, when we hear they about the competition, they are submitting their proposal, they are going to answer the questions that we have by COB Friday. Who are those days? We have to find that out, because if we don't know who the competition is, we're aiming on the dark, and imagine if we're selling, I don't know, a $250,000 car, and they say, we're going to look at the competition, we don't know who that is. And then we later find out, I don't know, it's a Prius, and maybe a 1989 Honda. Great cars, maybe not good competitors for our quarter of a million dollar car. Figure out who those days are, you'll open up a whole series of information that you need to know to get your deal done. Sam, that first takeaway is amazing. When someone's like, I'm going to the board, how do you suss out if they're presenting asking or telling? I think what you need to think about is, change the lens of how you look at this partnership with your buyer. We are so uncomfortable in asking uncomfortable questions, because we don't want to upset anybody, we don't want to step on toes. If you inside about, think and said that it's you versus them, think it's you to encourage. They want your software solution technology, whatever it is. As much as you want, let's be honest, they're money in the revenue, right? When you go into this work meeting, is this the first time you've done this, and two, are you presenting, do you have to ask for permission? Are you telling them like, because you have authority to do this, tell me about that simply by asking this, right? You're hopefully going to open up the conversation for them to be honest with you, tell you exactly what's going on, and for you to think about those questions that are forthcoming, those objections that they're going to get, you can build an ammo list for them. You are going to make sure that they are prepared as all get out for this presentation, or hopefully this. If you think about that advice, and you're like, oh, it makes me cringe, it may also be a sign that one, you don't feel like this deal has as many likes as it does, or two, that you haven't built the relationship enough with this buyer, well, we talk about it all the time. Understand your buyer, who they are, not only as a wallet, shareholder, with somebody with wallet share, but also who they are as a human being. Get to know them, build that rapport, and then you can earn the right to ask those questions. Could you give an example of a deal, or maybe a story where you sent some hesitation in their response? This is something that happens when we listen to discovery calls, and we listen to calls that move further along all the time. We hear the hesitation, because the rep is really just pushing and pushing a particular solution that hasn't been vetted correctly, so maybe that buyer just says, you know, we're making our presentation of the options on December 12th. A person hears, you know, happy ears, I think that this is going to move forward. They throw it and commit. We hear the hesitation there from the buyer to give any additional information, because they're probably not, right, sure that that's the opportunity that they're going to go with or the solution they're going to go with. Again, this is why just in the very beginning, right, the discovery works that you do, asking open-ended questions, broad questions about the true business pay and they have is so critical, so we can really understand who we're dealing with, and if this opportunity is worth our time. Sam, let's make this real. I sold accounting software to law firms for a very long time, and very often the CFO or the CFO of the law firm that was looking at our solution would be making a presentation at the quarterly meeting of all of the partners of the law firm. I'm in that conversation with CFO, and they're like, hey, on December 12th, we're going to be giving a presentation of the partners of all of the options. They tell me we're going to be presenting options. What should I be asking them and what are some of the other questions I should be asking them to help them have a better presentation and help sway the deal in my favor? The first thing I would do, especially because you sold accounting software to law firms, and you understood the law firm and the professional services space, which is one that I specialize in. for a very long time. The first thing you should do is make sure that they understand your expertise in their space. So you could leverage that to earn the right to ask these questions. So number one to say, you know, the last time I worked with K&L Gates, the last time I worked with Scadden, right? One of the things that came up was partners always seemed to ask this. Then managing partners to the buying committee, right? The executive committee asked this and this and this. Have you guys heard those questions before? Is that important to your firm? Tell me about that. The second thing that often comes up and I know every firm is different, but when we think about this, is this all within your authority or is this something that needs a majority vote in terms of spend volume, right? What does it look like for you guys, right? Is this ultimately your decision or do we need to get some buy-in? The other thing to think about is how can I help you prepare for that meeting? As you guys have presented, you know, software that you want to purchase before, what questions come up, what objections come up. I know sometimes firms have one or two very persecutive and skeptical partners. Do you guys have that in your group and how can I prepare you for their questions to make you look like a star? Use in the language that feels authentic not only to you, but then also that fits the personality of that person. But again, you are helping your deal get across the line, but at the end of the day, you're trying to make them look better by being prepared as they can be. So there's also going to be some scenarios where somebody goes, "Hey, I'm not going to be presenting. I'm not taking these options back on December 12th. I'm going to be telling them this is my recommendation for us moving forward. How does the conversation differ there with your champion?" Hey, I think you asked them the same question that you're later or that you should be asking yourself, "Why won't this deal get done?" What's your perspective, right, after you say, "We're going to buy the software. It's a multi-year deal and we're going to buy it for five million bucks over the course of three years. Why do you think that won't get done? Any objections that you can anticipate? Any pushback you can anticipate? Are there relationships maybe that others have with particular software firms that we need to think about? What can I do to prepare you for this? Maybe knowing what you've known from presenting options like this before? The other thing I would focus on again is thinking about the procurement process for whatever spend volume you're getting at. Some people don't think that this is something that they have to go through depending on the size of the organization and the price of the software. But let's say even if you are presenting to a multi-billion dollar organization of Fortune 500, oftentimes it's the opposite of what you'd expect. Percurements, tougher spend thresholds are lower and you need 16 different stamps from 14 people who are all going to be on PTO at varying times to get your deals done. So ask those questions as best as you can. I thought one of the other things that Sam does really, really nicely there is you're not just asking the, "Hey, what's Matt going to ask you when you go in the room?" You are suggesting for them, "Hey, might it be that there's others that have relationships with other software firms that might sway their opinion on things?" You're almost giving them a couple options because if you just ask the big high level question of like, "What resistance might there be?" It's hard for them to do the full search of every possible combination and permutation. But if you say here's some common resistances, they can pick some of those and you can talk about them, but it also starts to jog their thoughts. I do want to double down on what you just said Nick, really quick because I think it's important. This is part of every single part of our sales process is that suggestive capability. If you just said, "What are the questions that are going to come up?" You're going to get what's already been in their buckets or what's in their minds right now. We lose deals all day long and we know why we lose deals all day long, right? We have that basket of here, the 78 reasons I lost deals this year. So think about those things as they would apply to this vertical, this buyer, the size of deal and suggest that stuff, right? People say all the time, "How do I multi-thread without being salesy?" Next, the ultimate decision maker I'm talking to Armand, "How the hell do I get to Nick without stepping on Armand's shows?" Start asking questions that Armand can't answer, instead of being like, "What's Nick or the Care about?" Think, ask these very specific questions that you know a buyer like Nick would care about and that Nick probably would be the only one to answer. What are the priorities for this year? What are you guys forecasting? What's the growth? How are you? What's the roadmap? How are you going to get there? Ask these specific things that Armand is going to say, "You know what? Nick's probably a better person to answer those questions. What do I bring him at?" And it would be like, "That would be super." So how do you broach that conversation? Because, ever once in a while, you're champions of a buffoon. And like, unfortunately, you're selling to a buffoon. And it happens. And I've sold to a people leader where I'm like, "I know this head of people has to be the person that's going to talk to the CFO. It's there not a champion. They're just a champion that I know has no political clout." So I'm asking them all these questions. They're like, "I don't know. I don't know. I don't know. How do I get them to hold me into that meeting instead of taking it alone?" One of the things that I think is really cool about sales is that you can use language to your advantage. So we talk about this all the time, hashtags, semantics matter. So one of the things I love to do there is to say, "Why don't we do this?" Armand, I probably filled your head with all these questions and you're probably frustrated with how often you're saying, "I don't know." Do you think Nick would have a better sense of these answers? It could be Luke Permanner. I also wonder if your SDR leader would have some great things to share about their frustrations, what they want to do differently. "Why don't we do this? Why don't we grab another time to chat?" I've got a couple things I want to mention. I said, "I'm going to actually include our CS leader. I think we'll have some really great perspectives on this." And then why don't we grab Nick and buffoon number two over on your SDR side to come over on or call? How does that sound to you? This will also give you a good temperature check. Are you talking to somebody that's just going to buffoon your buns off and be a gay keeper the entire time or do they actually have authority to help make decisions here to bring in multi-threads and move it forward? Because we have talked to those people. And if you talk to just that person again and you don't figure out how to multi-thread, you are going to do nothing but waste your time. So come hell or high water. Why don't we do this and suggest the other people to bring in? Can we go to the suggestion that you made which was asking our buyers questions that they don't know the answer to? This is something that I've struggled with in my career. I sell all of our sponsorships for 30 minutes to President's Club. And usually we need someone who's at least a VP level, maybe even a CMO, to approve our level of spend. Usually our deals start with a marketing manager. And that person wants to collect a lot of information from us. They want to know about our audience and our demographics and our pricing and the activations. And nine times out of 10 when I give them all of that information, they take it back to their boss. And I have a closed-lost deal that Armand is yelling at me about. And go back and go higher. But foods can sell too. Who would have known? How should I be running those initial conversations or two with the manager level folks in these deals? I think help educate them on the objections that you're already going to get. So let's say the objection. What's the most common objection that you get? Sometimes we get we don't have budget for this. Our budgets are already allocated to whatever. Now I would argue right a lot of the time that from a budget perspective, it's just because we didn't prove value. So let's say we get on with the marketing manager and we say I'm going to run you through our demographics and things like that. I want to ask you just a couple quick questions. So when mostly around budget, right? Sometimes we get pushed back from our buyers who say we don't have budget allocated for this and we have to get creative with them about where to pull budget from. When you think about your sponsorships or even thinking about all the different buckets where your marketing dollars go, what's your sense on what's been the most successful? What hasn't had great ROI? Like tell me a little bit about that. Oh well, I really only see sponsors overseas sponsorships. Tell me who does your syndicated third credit content. Tell me who does your paper click campaigns. Can you talk to me about that? Should we bring them on the call? Because I think, right, one of the great conversations we can have when we work with your broader team is thinking about the places where ROI just isn't clicking and pull budget from those places to help you get sponsorship of our podcast. Any thoughts there? Just start to think about those questions, right? If you want to work with us, we got to get creative. I think it's so smart what you're doing is you are raising that roadblock and you're not afraid to have that uncomfortable conversation of like, hey, usually this is an area that and you're saying this really, really, really, maybe even before you've proven all the value of what you do, you're saying we're probably going to have to get creative and we might need to pull from some of these other areas and I feel like you're also helping them expand their scope in their mind of like who actually gets impacted by something like this. You mentioned the folks running the paid ads, the folks doing syndicated third party content, which isn't normally folks typically have a far more narrow lens in terms of how they're thinking about whether it's a sponsorship, an accounting software, or whatever people are buying. The way you have to think about all the time is that people are coming to calls with you not for their health. There's an actual challenge that they have to solve that there's something they're looking to accomplish. So what is that? What's the budget that you have available for it? What are other budgets that we can pull from it? And I think just an important takeaway, especially even for our senior sellers, the amount of time that we hear back again, budget was a concern or budget wasn't allocated for this. Well, no ship budget wasn't allocated for this, especially if it's something new that you're selling, but you have to figure out how to partner and multi-thread to pull from different budgets. And it may not even be what you think. Perhaps, right? You're thinking about how to sponsor something, 30 minutes to president's club as a great way to attract new talent. Can we talk to HR? Can we talk to your chief people, officer? What are you guys doing to bring in fresh young minds? Because I'll tell you, our demographic may be a 6% VP, but the BDRs that are really investing in themselves, the AE's to better themselves, they're listening to our podcasts. So think about that, right? What are creative places where you can get money? I was running into this issue the other day. We're founder was about to multi-thread. So they were about to go from champion up to power. And they actually got to power on the second call. And the problem was the champion wasn't convinced yet. So literally the champion was, they still had both vendors in their head, two or three vendors in their head. They're like, this one's more expensive, this one's less expensive, whatever it is. And what he actually ended up doing is for future deals who are like, let's delay multi-threading up until we can at least say that we have one or two people bought on board. And so I want to get your reaction on that. At times does it make sense to slow down that presentation of power to get your ducks in a row? Or do you want to get in front of power as soon as possible? - I would always start with power if you can. So maybe just a quick caveat there, right? Don't be afraid to go up the food chain. And again, one of the things we talk about with our show me you know me methodologies that you have to basically put in the effort to do research right a great subject line. People are like, well, who does it school to 400 marketing managers? It doesn't. You just go to the CMO and you say here's what we can do for you and then work your way down. The part just by the way that I love about that is if I, let's say Nick is the CMO, right? And I go to Nick and he says, go to Armand. Now when Armand either blocks me, doesn't respond to me or whatever, not only can I go back to Nick, but I can also just keep Nick abreast of what's going on because Nick introduced me to Armand. So go up first and then work your way down. The part I love about sales is that it's an art, right? It takes your EQ and account. It takes you really understanding the dynamic of relationships and people to get ahead. So take each opportunity that you have in a different way, I would just say, like think about what that person's like, what you need to do if they are skeptical of you, if they already have relationships with other vendors, you've got to really suss that out. But more than anything, show up to the call to solve a challenge. So don't come and say, tell me about the landscape that you guys have going on over there. Tell me about your challenges. Tell me that the issues you're trying to solve. What are the initiatives you have ahead? I'd love to hear about you guys first. Let them date a dump on you and really look to solve their challenges because if you make that investment in them, like no other reps do, truly, they're going to take you to power pretty quickly, hopefully if they're the right buyer to begin with, but start there and then feel it out. I say more often than not, faster that you can multi-thread and get to power the better, even if it's not power, multi-thread, double the quantity of the people that you have in the call, get two marketing managers on the next call instead of just one, doesn't always have to be out. Yeah, the way that I think about it as well is you might have to multi-thread us before you multi-thread up. And to me, that's the more conservative path, but you shouldn't just stick with someone who's not inst for 20 steps and wait for them to be convinced. That might mean you don't send them to the board on day one, but you should actually still go and try to get some other allies in your deal cycle. The last to go back to is actually your second takeaway, which is all this has been talking about getting to power, getting approval, and there's another step that can slow down the deal that happens after this, which is a three-month vendor review with procurement and legal and security, and everyone knows or many people know that the best reps are parallel processing vendor review during the evaluation. And so talk to me, when is the right time for me to start parallel processing vendor review? - I think again, as soon as you have what you need to know that this deal is going to move forward, so whether you subscribe to Bantan, you've got all that figured out, whether the buyer has said we are moving forward with you, I am telling the board what I am doing and it is going to happen on December 12th. Whatever it is for you to need to know and for your leaders to know that this is a 90% commit deal, 75% commit deal, whatever it is. Once you get there, you've got to think about how do you speed up that process, right? Because by the time, if you're parallel processing this paperwork, by the time the decision happens, by the time the person comes back from vacation that's going to sign your MSA, whatever that is, you're going to have 95% of the paperwork done. I also just think about the personal pride that I have as a seller of being able to go to my leader and say, here's what we need to do. It's August deals not gonna happen until December, but I've gotten this checked off, I've gotten our MSA's online, I've gotten 17 people on our side to prove the nine things that are not going to be doable on their end that I am as locked and loaded as I possibly can be. And then I'm still working with my leader to say, why won't this deal happen? What else haven't I thought of, right? The last deal I needed to get to my first president's club was with Teva Pharmaceuticals. And it's when I learned that there was a stamp that was needed by some obscure procurement team. And I didn't know this, right? I mean, this was going to cost me my first president's club. So even making sure, talk with your peers, talk with cross-functional leaders. If your leader is a phone, talk with other leaders and say, what am I not thinking of, right? Also the importance of sponsorship internally and mentorship internally, go and meet with a top performer. What have I thought of? Make sure you figure that stuff out. So you can be thinking about all the stuff, right? Before you get to that end goal, where you, instead of going back and be like crap, I wish I'd thought to do that, you know, put in the work. Other than late stage vendor review, let's actually go backwards to earlier in the deal. What are some common places that you recommend? Sellers have parallel next steps rather than sequential next steps? I think one really great thing is to think about the other cross-functional teams that you'll be working with. So even as you think about, you know, we're gonna move this up the ladder. We're gonna talk to our leaders about it and get that approved. Let's see, we're talking about a multi-year deal and we know that as soon as we sign, our CS team is going to kick in or our AM team is going to kick in. Are you also multi-threading across those teams? Have you brought in your CS, your AM team? Have you brought in an AM manager? Have you gotten your executive leader to get a meeting with that executive leader? Let's say on the other side. These are all things that you can do to start their multi-threading, but also to build those relationships. I think the other thing, just as we're waiting on other next steps and people really miss this for enterprise deals, is to make sure that we have recurring meetings happening. So again, if we're in August, let's say and we're still forecasting this for a year and December, what I want you to think about is how much work and continued poking and prodding needs to happen to get that deal done. So do you have a meeting with legal and procurement on your teams every week, every other week? So they're holding ourselves accountable too. These are all things you can be doing again to keep that deal moving and to keep the relationships building in parallel. I love how you're pulling so many of these plates earlier, the cross-functional aspects, the procurement aspects, the legal aspects. And folks, oftentimes, I have the exact same rule Sam, which is I start trying to parallel process the moment I feel like we're selling on the same side. So the moment I'm like, okay, we're on the same side of the table and it's not, I'm trying to win you over anymore. It's like, all right, that's when we start parallel processing. But sometimes that happens later than you want. And so there are still things you can do early in your deal cycle to sort of get sneaky and start vendor review. For example, you can get an NDA signed early in your deal cycle. And that will usually at least get you on the radar of legal. Oftentimes what we would do is we would like spin up a trial portal or we would spin up a demo instance for someone and that oftentimes kicks off a lightweight security review. And it just like gets the IT review started earlier than you would need to. So get creative and figure out all these ways that once you get good at closing deals, if you're good at closing a deal in four months, your next task is not to just figure out how to close all those deals and close more of those deals. It's figuring out how to close your four month deals in two months. And that's where the best sellers actually make it to club. - I think you just said something else. I think that also might perk up some ear security review, right? So depending on how you're moving through the organization, if you just got promoted, let's say from us and be a commercial enterprise, you might have never heard of something called an InfoSack Review, right or security review. You, there might be the very first time you're hearing an afternoon like that. So again, I think the importance of working with cross-wemchial partners internally why won't this deal get done? If you went to Armand and he was like, what did you do InfoSack at? And you said, what is that? Just easy ways for you to learn to be proactive about the way you chase this. - Wow, Sam, we're gonna need to have you back. This was one of the best ones in a long time and sadly we are running out of time. So we gotta move to the final question. Final question is this. We've talked about a lot of really great things salespeople should be doing. Now I gotta ask you about a shouldn't. And so the last question is, what is one bad habit that you see a lot of salespeople exhibiting that you think they need to break because it hurts them before that it helps? - Sending calendar links in your outbound emails. Dear God, don't do it. Two quick things on this. Number one, if you send a calendar link, it is presumptuous. Number two, you're putting the onus on that the buyer just scheduled time with you. If you really, really wanna be selfish in the way to think about this, as you object and say, but it's so convenient, Sam, here's what you wanna think about. Instead, you are letting a buyer circumvent all of your personal stuff on your calendar. Your one-on-ones, your daily massage, just me. All the things that you have to do, you're making then circumvent that instead of saying, you tell me when you're free and I will make that time work some way, come hell or have water, don't do it. - Artinik, it's time for a two-by-do recap email from this episode with Sam McKenna. What do you have for your two? - The first is the recurring meeting. You will eventually in complex deals get to a stage where you and your champion are selling together and you are probably going to need to meet with them on a regular basis to get intro to multiple different parties to cover different questions and items on their list. Number two is set next steps in parallel, not sequentially. You do not need to just have one next step on the book if the next next steps are not contingent upon that next step. The example Sam shared was if you have next steps the different cross-functional groups. customer success, the technical team, the attorneys at the law firm that you're selling to. If those aren't dependent upon each other, get them all scheduled now because now you start to create some momentum in your deal and everything moves faster. Number three, you need to figure out if your prospect is going to present to the board, ask the board or tell the board they're buying this thing. And if someone is presenting to the board, that means you have a lot of work to do with your champion and you need to unpack their concerns and prepare them for the questions they're going to get from their financiers. Number four, if you want to get access to power, you can start asking your champion the questions that they don't know the answer to. All of the things that plus CFO or a board member is going to bring up prompt those to your champion. And when they don't know the answers to them, you like, hey, is this something that Nick might know the answer to? And that's your end. Today's show is brought to you by Proposify, the Proposal Management Software Design to make every deal a close deal when you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion. You want to make it easy for those other people to digest and you want to be able to control the narrative with your presentation. And bonus, Proposify Data shows that when buyers watch the video, it increases your chances of winning by over three acts. So do not let your proposals become a disappointing plot twist. Get our Proposal Success Guide free in the show notes. Today's show is brought to you by Responsive, which help sales teams respond to RFPs, security questionnaires, and buyer requests faster so deals don't die at the last mile. One great way to drive your deals faster is to run parallel processes instead of linear processes. For example, in vendor review, work with your buyer to kick off legal security and procurement review simultaneously instead of doing them one by one sequentially. You built a playbook with our friends at Responsive on different proposal accelerators that you can use to close deals faster, grab it in the show notes.

Podcast Summary

Key Points:

  1. Sellers should shift from cold outreach to warm, relationship-driven strategies using network data to gain introductions to high-value accounts.
  2. Understanding whether a buyer is presenting, asking, or telling to the board is critical for anticipating objections and preparing effectively.
  3. Parallel processing—initiating cross-functional engagement (e.g., procurement, legal, CS) early—accelerates deal movement and creates momentum before formal approvals.
  4. Identifying key influencers, decision-makers, and competitors within a buying committee enables smarter targeting and reduces decision-making uncertainty.
  5. Asking buyers questions they don’t know the answers to builds trust, uncovers hidden concerns, and reveals opportunities for multi-threading.
  6. Early parallel steps like NDAs, demos, or trial portals help trigger internal reviews (e.g., legal, IT) and build momentum long before the decision point.
  7. The best sales strategies involve recurring meetings and proactive coordination with internal teams to maintain consistent progress.
  8. Avoid sending calendar links in outbound emails—this is presumptuous and undermines the buyer’s autonomy and scheduling control.

Summary:

Sam McKenna, a top sales leader and founder of Sam Sales, emphasizes a fundamental shift in outbound sales: from cold calling to warm, relationship-based prospecting using network data. She highlights that understanding a buyer’s decision process—whether they present, ask, or tell the board—is essential for anticipating pushback and preparing for tough questions. A key strategy is parallel processing, where sales teams initiate cross-functional engagement (procurement, legal, CS) early and simultaneously, rather than waiting for sequential approval.

This builds momentum and accelerates deal timelines. She advises sellers to identify key influencers, competitors, and internal stakeholders to gain deeper insights. By asking open-ended, uncomfortable questions—especially those buyers don’t know the answers to—sales professionals uncover hidden concerns and foster trust.

Early actions like NDAs or demos trigger internal reviews and create visibility. Recurring meetings and proactive coordination with internal teams maintain momentum. Crucially, she warns against sending calendar links in emails, as it’s presumptuous and undermines buyer autonomy.

Ultimately, top performers don’t just close deals—they close them faster by building relationships, anticipating objections, and working across functions from day one.

FAQs

When a buyer says they'll present to the board, they may be asking for permission, telling the board what they'll do, or presenting options for feedback. Understanding which model they're using helps you anticipate objections and prepare them effectively.

Sellers can begin parallel processing early by signing NDAs, spinning up demo instances, or scheduling meetings with cross-functional teams like legal, procurement, or customer success—even before the deal moves to the next stage.

Knowing who is in the buying committee—such as key influencers, executives, or past clients—helps sellers tailor their approach, build relevant relationships, and anticipate objections that could delay or derail the deal.

The seller should proactively ask about the board’s process—whether they're presenting, asking, or telling—and prepare the buyer for potential questions by identifying common objections and building an ammo list for their presentation.

Sellers should ask about current budgets, ROI across marketing channels, and where funds might be reallocated. This helps uncover hidden budget flexibility and positions the seller as a strategic partner, not just a salesperson.

Early multi-threading with legal, procurement, CS, or AM teams builds momentum, ensures alignment, and reduces delays. It also establishes relationships that accelerate deal progression when the decision to move forward is made.

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