Most deals slip when everything depends on one person. One champion goes quiet, priorities shift, or a new stakeholder shows up late, and the whole deal slows down.

James Buckley, Krysten Conner and Monica Stewart broke down a simple, repeatable way to multithread early without looking desperate or going around your champion. This is about building alignment and reducing risk, not adding people to a thread.

You will learn how to map the buying group fast, open new threads with a clear reason, and turn the right contact into a real champion who sells internally when you are not in the room. They will cover what to say to your champion, what to say to new stakeholders, and how to ask for intros without making it awkward.

You will leave with practical scripts, a straightforward framework for keeping multiple threads warm between meetings, and clean re engagement moves for when a thread goes dark in mid market or enterprise deals.

You'll Learn:

• When to start multithreading and how to map the buying group early so deals do not stall on one contact
• How to build a real champion, spot the difference between a champion and a friendly supporter, and ask for the right help
• The plays to open new threads, run stakeholder meetings that move the deal, and keep momentum when people go quiet

The Speakers:

James Buckley, Krysten Conner and Monica Stewart

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Thank you to our sponsors: ZoomInfo and Quotivity

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James Buckley: What is poppin'? What is crackin'? Y'all know what's about to happen. It is me, it is I, we are back. James, say what, Sales Buckley with Sell Better. I give you guys a second, you know…

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James Buckley: Deep breath, woosah! Come into the room, take your thinking cap and put it on. You're probably coming off of some cold calls, maybe you're coming out of a one-on-one. We've got some great experts in the room for you today, and they are gonna show you some cool stuff. So, be ready, and get your, get your questions geared up, because we're gonna leave some time at the end for Q&A. Let's kick things off proper. Welcome back, everybody, to the Sell Better Daily Sales Show.

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James Buckley: Where we bring you daily sales advice to help you sell better. Today, we are here to talk about multi-threading that builds champions. You guys know that I like to get a feel for who's in the room, so I'm gonna launch this really quick. Identify yourself. Are you an SDR? Are you an AE? Are you an alien in the wrong room? Also, change your chat settings down at the bottom to everyone, and tell us where you're tuning in from. Shout out to Jeff Pearson.

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James Buckley: From Jacksonville, Florida, I see you. What's going on? The two ladies that are in the room, proper introductions. Kristen Connor, the founder of Kristen Connor. What is happening? It's been too long since you've been back to the show. I think last time we had you was last year at some point, if I'm not mistaken.

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Krysten Conner: I know, it's crazy, but delighted to be here again. Thanks for having me.

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James Buckley: Absolutely. And then, of course, Monica Stewart, you've probably seen her content on LinkedIn. She is definitely showing up in my feed more often. Founder of MSP Consulting, it is great to have you here. Thank you for joining us.

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Monica Stewart: Thank you so much for having me, James. I've always been a huge fan of the show and really excited to be on.

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James Buckley: Alright, well, I love it when fans of the show turn into.

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Monica Stewart: Yes.

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James Buckley: show, that makes me super happy. For those of you that are not in the know of what a nerd I am, it is International Tolkien Reading Day, so for all of my Tolkien Middle Earth nerds out there, I'm showing love to you today by rocking this shirt. Scan this QR code, check us out at SellBetter.xyz, and while you're there, hop over to the YouTube channel and subscribe to get all the latest, greatest tips, techniques, tactics, and takeaways from our YouTube channel.

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James Buckley: Check out who is in the room, ladies. We got SDRs in force.

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James Buckley: and AEs by a hair, just a little bit more AEs, but 15% senior leaders and 5% frontline managers. We need more folks in there. Yeah, second breakfast, I hear you on the second breakfast.

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James Buckley: Great folks in the room today, so get ready for a lot of learning. I want to give a big ups to my friend Jed Marley, who just launched an incredible modern prospecting course. We are going to drop that in the chat. This is a great course if you need to step it up and update your prospecting game. Jed puts some incredible content out there, so make sure that you grab that course from us. And I want to give a big thanks to our longtime partner, ZoomInfo, for being a part of this episode.

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James Buckley: You guys know the biggest question in sales, how do I do this at scale? So ZoomInfo put together an amazing guide for you, and we're gonna drop that in the chat for you right now. And then, you may have noticed the green background, that is to celebrate our newest and one of my… one of the best quote in HubSpot solutions I've ever seen, Quotivity. Now.

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James Buckley: Put a 1 in the chat if you have ever had an issue or struggled to get a quote.

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James Buckley: Quotivity. Alright, multi-threading. We're gonna talk about that to kick things off. These things stall, and it's usually because we have just one conversation going. We're gonna talk about real champion and what that actually means in the modern age, and then, of course, you can't come to a Sell Better show without getting plays that you can take away and start using right away. So, ladies, let's kick things off proper, and right now, I want to start with this.

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James Buckley: You guys suggest that multi-threading equals faster and higher win rates

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James Buckley: Defend your position. Did we start with Monica on this? We did, right?

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Monica Stewart: Yeah, I can go ahead and start. So, James, there's been a ton of studies that have been done on this over the years, and generally, the stats are, like, between 32% and 37% higher win rates if you multithread. My favorite one is Outreach just came up with something in Q4 where they showed that cross-department multi-threading can increase your win rates by 56%. So, it's like, baseline is you should at least be talking to a couple people on the same team.

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Monica Stewart: But if you're bringing in people from multiple teams, 56% higher win rates.

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James Buckley: Yeah. 56 is no joke. I mean, I could definitely use a 56% boost in my win rates. Kristen, thoughts on that number, or additional thoughts, additional data?

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Krysten Conner: Yeah, I hadn't heard that stat, but it makes complete sense. Sometimes we get tempted to multi-thread just in one department, right? Because we have one, maybe, primary use case, but that number makes complete sense to me. The more departments you have that's coming to a CFO asking for money, the less risky it is for everyone, including the CFO, and I've seen multiple,

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Krysten Conner: just going back to the studies, one of the ones I think about the most is outreach to a study.

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Krysten Conner: While I was there, it was, like, 5,000… across 5,000 deals, 40% higher win rates, but the deals also closed faster and.

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Monica Stewart: Closed.

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Krysten Conner: bigger. So, I think it's… it's… all of those are worth talking about.

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James Buckley: That's interesting. I always like to have fun with the audience here. Let us know in the chat if you know what is the average timeframe of a deal for you? Are you selling enterprise and it's like a year? Are you selling mid-market and it's like, you know, 90-day cycles, 6-month cycles?

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James Buckley: You know, maybe it takes you, you know, 10… I just closed a deal the other day, small deal, in 10 days.

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James Buckley: Right, so that's how long it took. Nishant says 15 days, 2.5 months. Monica, any thoughts off the top of your head? What are some things that you think of when you think of, like, time from start to finish, you know, first meeting to close on a

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James Buckley: deal versus a single-threaded deal. How often do we start over? I feel like it's Chutes and Ladders or Candyland, you know, you're, like, right back to the beginning.

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Monica Stewart: All the time. So it's like, if you think about, even in a mid-market deal, right, if you're single-threading, you have your discovery call, you have your demo, and then what usually happens if you're not multi-threading? You end and the person's like, this looks so great, send me some information, send me the recap, and I'm gonna go talk with my team, I'm gonna go discuss internally and get back to you. And you're like, cool, amazing. And then there's, like, this gap.

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Monica Stewart: Which is, like, weeks.

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Monica Stewart: Could be months, where…

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Monica Stewart: your deal has gone into a black box, and what's happening is that there are conversations that are happening on the other side. They're happening without you. You don't know who they're happening with. And I just don't know where we get this idea that the, you know.

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Monica Stewart: the, the, the VP of Product.

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Monica Stewart: Or, like, the head of e-com, or whoever it is that we're selling to, is all of a sudden gonna know how to sell our product, when we have to learn how to sell our product, and we're professional salespeople. And so I think, like, you know, multi-threading has always been something that has always been pretty much table stakes in enterprise, but I'm seeing now that even people who are selling to smaller companies where there's, like, 3 to 5 people that are involved in their deal, which, when you think about it, it's the person that's signing your contract.

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Monica Stewart: It's, like, one or two users, and it's the CEO or the person who's in charge of finance who's gotta… who's gotta sign off on the budget. That's three to five people right there. That's definitely happening in every single deal that you guys are selling.

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Monica Stewart: You're going to lose deals because you're putting all of the work on your customer, unless you're helping them proactively manage that conversation.

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James Buckley: I like that you act as a conduit between all of the stakeholders, because it's very, it's very octopus-like, right? I need all these

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James Buckley: Kristen, I see you shaking your head. Thoughts on the number of people, the number of channels, I think, is a very interesting conversation as well.

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Krysten Conner: Yeah.

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Krysten Conner: I think that's a good call, because people prefer to communicate in different ways. I have had VPs that will… that have never replied to an email, even while a deal is ongoing, but if I send something to their LinkedIn inbox, they might reply in 5 minutes. They might never respond to an email, but they will send a Slack or a text. Like, you just…

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Monica Stewart: It's important.

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Krysten Conner: ask and to notice. How do you prefer to communicate? And I think that's why we have to… to me, the big three of sales are connecting the dots, what's in it for me, and reducing friction, and under the heading of reducing friction, that means messaging people in multiple channels to see what works the best for them.

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James Buckley: Yeah.

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James Buckley: Yeah, I agree, and I've got a great question here from Donna Robb, and I'm gonna wait until we get to the next slide, Donna, because that is a perfect segue question into the next slide. Before we do that, I want to talk about the number of channels that we're using when we're multi-threading.

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James Buckley: This can sometimes get a little bit overwhelming, right? Because when you think about the amount of channels that it takes a typical salesperson to run through, I think about LinkedIn, obviously. Then there's email. Then there's calls. Do I leave a voicemail? Do I not leave a voicemail? Is voicemail considered a channel? Then there's the video aspect of it. And then there's the voice note aspect of it after they accept it. When you think about the number of channels, Kristen, that you're using every day to multi-thread your accounts.

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James Buckley: How many channels are being played into here?

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Krysten Conner: I would say, like, I see the… I see the pole, I would say I hit him up everywhere, right?

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Monica Stewart: So it's… you're one of those.

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James Buckley: I'm difficult to ignore people, because every day it's something different, right?

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Krysten Conner: pleasant persistence, right? And, and yeah, you just, you don't know until you try.

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Krysten Conner: what… where people prefer to communicate. And also, if you think about just marketing data, we can borrow from our friends in marketing, like, how many… it takes, like, 20 touches or something for.

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Monica Stewart: for people to.

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Krysten Conner: become aware, right? Like, you want to be everywhere.

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James Buckley: Yeah.

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James Buckley: Yeah, and I think it helps to be everywhere, but it also helps to be everywhere that your prospect is, if that lines up.

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Krysten Conner: Right, yes, exactly.

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James Buckley: Monica, I see you shaking your head. When you think about the channels you're using, is it like everybody else? Is it the ones that I mentioned mostly, or do you have, like, a secret channel that you find to be super helpful?

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Monica Stewart: Actually, WhatsApp, I'm seeing more things move to WhatsApp, which is pretty cool. A lot of my clients are also European, or they have, you know, they're selling to people in Europe, and, you know, WhatsApp for business is much more of a thing outside of the US, but I'm seeing that happen more and more. You know, you can also think of, like, not every touchpoint when you're multi-threading has to be an ask.

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Monica Stewart: if you're working in a longer deal cycle, sometimes it's just kind of, like, continuing to do value drops and stay in front of people, and you can do that by inviting them to a webinar. Like, there's, like, you can get creative about thinking about the ways that you're continuing to develop the conversation and stay top of mind, but I'm with Kristen. I hit people up everywhere, and my friend Leslie Venetz calls it channel of choice, right? Here's all the ways that we can connect, and then you'll let me

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Monica Stewart: You know by responding where you want to respond, where you want to be communicated with.

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James Buckley: Yeah.

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James Buckley: Yeah, I don't care which channel you choose to engage with me on, but once you engage with me on that channel, that's where I'm going.

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James Buckley: We're there!

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James Buckley: Yeah. And I'm a big WhatsApp fan, too, and I think people sleep on WhatsApp. Let us know in the chat, yes or no, are you selling internationally, or is it all local, where you are? Just curious. We've got great questions rolling in. Keep them coming. Let's move to answer Donna's question, because I think it's such a great segue into the 3x3x3 method. The question that was asked is.

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James Buckley: How do you get started multithreading? Do you make those calls? I sell RFID equipment and tags to event rental companies, and I normally only talk

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James Buckley: to the champion. And I think, first of all, Donna, you gotta talk to more people than just your champion, and I also want to talk later about how you're talking to that champion. Let's talk about the 3x3x3.

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Krysten Conner: Yeah. Yeah, I think that concept of where we're talking to the champion to begin with, where we're talking to end users, or managers of end users, that's a pretty typical first

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Krysten Conner: conversation, right? And that's… that's normal, and we don't want to stay there. So that's why I like this 3x3x3, and this happens before that, ideally, before that first meeting, where we reach out to 3, what we might call above-the-line or VP-level users. So whenever I was selling to school districts, that would have been…

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Krysten Conner: VP of HR, VP of IT, VP of Finance or Operations, and say, hey, I've scheduled… somebody reached out to me, and we're scheduling a meeting to talk about

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Krysten Conner: XYZ business problem. Executives aren't always involved in every conversation, but wanted to put this on your radar in case it's of interest. Here's the invite to join the call. If you can't, no worries. I'll send you the readout afterwards.

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Krysten Conner: Because, that puts it on executives' radar, which either gives us a boost, because now we have awareness at the executive level, or it gets us a quick no, meaning this is not a priority for us as executives, this is someone who's just reached out.

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Krysten Conner: We hate… we hate no, but a slow no is so much worse than a fast no.

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James Buckley: Yeah, I love that. You know, John Barrows, a good friend of mine, has always said, it's not the worst thing in the world to lose a deal.

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James Buckley: But it is the worst thing in the world to take a very long time to lose a deal, and I… that resonated so hard with me when he said it to me, it always stuck with me. Monica, thoughts on the 3x3x3, and what methods are you putting in place that work for you?

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Monica Stewart: I… huge fan of the 3x3x3, and I would agree with John, it's like, when you think about it, in best case, like, let's say you've got super high win rate, 35 to 40% win rate, you're still losing the majority of the deals that you go after selling. So, like, it's not a bad thing to lose a deal. You're actually going to lose more than half of the deals in your pipeline, and we just want to know what those deals are as early as possible, so that we can

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Monica Stewart: keep it moving. So, I would say that, like.

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Monica Stewart: I am 100% on board with coming in with a plan. So, especially these days, and we always talk about all the account research that we can do, and, like, all of the research that we can do with AI tools, and all these signals that we have coming into a call. There's no reason why you should be going into a call and asking people, like, oh, so who else should we be talking to? Who else is on your team? Like, you know who's on their team. You already knew that. You've known that for years, it's on freaking LinkedIn.

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Monica Stewart: And so, like, coming in with a hypothesis about what the buying process is going to look like, knowing that you, as the AE selling that deal, are the expert in the room about what it takes for a company like that to buy your product.

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Monica Stewart: Like, how often, like, let's say you're selling something like outreach.

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Monica Stewart: any customer that you're selling to, how often do they buy a new sales engagement platform? Like, every couple years? How often do you sell outreach to a company like theirs? A couple times a month. So, like, you know exactly how this is gonna go down and what it needs to look like, and I think that it's part of the value that we bring as salespeople is helping

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Monica Stewart: to kind of show them, like, so here's probably how the process is gonna go, and here are the things that people usually need to know at different stages, and I'm gonna help you have all of those conversations. And so, you're mapping the buying circle, but you're also mapping the buying process.

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Monica Stewart: You're coming in with a hypothesis about what that's going to look like, and then you're validating that hypothesis and building out the close plan with your champion.

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James Buckley: Anytime you can build out your conversation, whether.

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Monica Stewart: It's with your.

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James Buckley: champion, so that you're arming them to go and sell internally in an effective manner, not in the way that they think is best. Right. A caveat there, we'll talk about that later.

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James Buckley: Right? A little carrot in that one. Right? But anytime you can build out the conversation, you're creating what we refer to internally here as forward momentum with your deal.

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James Buckley: That is always a progressive thing to do. When you're thinking about full-cycle sales reps, you know, it's not about booking meetings. Booking meetings is, like, second nature to them. It's about getting a meeting and then having consistent forward momentum. Multi-threading achieves this.

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James Buckley: on an epic scale. So, Samantha, I loved your question. Please put your question in the Q&A. It is down below at the bottom, and you'll see an option there that says more, and then there's a Q&A option there. That's a great conversation I want to have.

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James Buckley: Quick question for the audience here, we can play a little bit in the chat. I see a lot of people using 3 to 4 channels. What's your most successful channel when you're multithreading? Is it an email?

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James Buckley: I figure, like, lots of people are probably sending multiple emails. For me, I like to start multiple DMs on LinkedIn. I think that's a really, like, special move. People don't… people don't do that most of the time, and I think it makes me stand out. Kristen, what's your most successful channel when you're multi-threading?

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Krysten Conner: I wanted to speak about two that actually weren't called out, because these, especially in, longer deals, so like 6 months plus, can be something to think about, and whether you sell those kind of deals now, or you aspire to sell them in the future, this is really something important to think about.

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Krysten Conner: One is the good old U.S. mail.

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Krysten Conner: When Monica talks about value-added touches, I had two six-figure deals that were stalled. They needed it, they had built the business case, they wanted it, and it was stalling, and I'm like, what is happening here? And I realized they did not know how to do the change management that was going to be required in their company.

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Krysten Conner: And so I sent that… there's a book called Switch by Chip and Dan Heath that talks about how to do

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Krysten Conner: like, change management, and it's a very accessible book. I highlighted some sections for them, sent it in the U.S. mail. Oddly, both of them, independently, two different companies, set up, book clubs in their company around how to do that.

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Krysten Conner: and then bought a couple of months later. So, don't underestimate the mail. And also, if you are doing longer-term, like, more complex deals on-site.

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Krysten Conner: If you can get in person, that is the best… that is the best multi-threading. A happy hour, a lunch and learn, like, don't… don't neglect that whenever we're accustomed to doing so much via Zoom, but in-person is the best.

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James Buckley: Go ahead, Monica.

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Monica Stewart: Oh, I was just gonna say, I love the book idea, and I love the level of detail that you went to there. Like, how could they not say yes to that? And I also am a huge fan of onsites. If you can't get an onsite, doing a Zoom, but not making it a sales call. I've had a lot of success with my clients recently who are selling, like, bigger mega enterprise deals to, like, banks, insurance companies, big logistics, like, you know, Fortune 500s.

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Monica Stewart: They need to get technical buyers on board, and they need to get business process owners on board, and those people don't want to do a demo or a discovery call. They want to know, like, how this is actually going to apply to their business, so having some sort of a workshop that you can come in and do and get people in the room, and then, it feels valuable, so you'll get, like, you know, ideally 5 to 15 people invited to that.

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Monica Stewart: If you're selling across multiple departments.

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Monica Stewart: And then after that, you come out with a ton of great feedback and a ton of use cases, and then that can help to fuel your multi-threading with your executive sponsors who aren't going to go to the workshop, because you can give them feedback from their team.

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James Buckley: When your decision makers miss key calls.

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James Buckley: that it's a reason to reach out. That's the thing we always need when we're trying to build that forward momentum, and I think every time you get the chance to build a specific use case that's relevant to that decision maker's role.

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James Buckley: you get to win with that one stakeholder. That's… that's probably the biggest payout when we discuss multi-threading. Ladies, I have so many good questions in here, and we've kind of… we've kind of hit a little bit of a head time here. Do you want to answer some questions off the top?

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Monica Stewart: Sure.

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Krysten Conner: By the way?

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James Buckley: Amazing. This one comes from MH. It's the most upvoted question. Are you reaching out to these folks at the same time, or are you staggering the outreach? For us, sometimes we reach out to smaller companies and organizations.

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James Buckley: And I'm worried about burning through all the contacts that I have available. I think that's a real concern for multi-threaders. What do you guys think? Kristen, we'll start with you.

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Krysten Conner: Yeah, I mean, I think the frustrating sales answer is it depends, right? Like, it depends on the size of… if you're… if you are working with, like, you know, small 10-person marketing agencies or something, like, yeah, you… do you want to burn… burn up the phone and email lines to all of those people? Like, probably not.

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Krysten Conner: So you have to, you have to…

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Krysten Conner: be judicious about it and understand, like, who you… who you have. Let's say, like, as I looked through, kind of, the averages, if we see the average deal cycle that I saw on the chat is, like, 3 to 6 months. Right. Yeah, you want to… you wanna be reaching out to them, and I would say, on a cadence of maybe, depending, like, if it's that cycle, like, every 10 days to 2 weeks.

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Krysten Conner: And…

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Krysten Conner: like, and you want… I mean, at the beginning, when the deal is starting, I would say, yes, you want to reach out to people that you think are… should be involved at the very beginning. There… because there should be… they should be, like, forwarding that around, saying, hey, did you get this message? It sounds like our team is meeting with them, like, you want that to be…

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Krysten Conner: like, at that at the beginning, but I mean, you also, like, you have common sense for a reason. You don't want to be obnoxious about it. So I think if you feel like it's obnoxious, it probably is. So, you know, just

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Krysten Conner: just base it on the size of team and the length of your deal cycle, is what I would say.

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James Buckley: I like that. Is it too soon? If you feel like it's too soon, it's too soon.

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Monica Stewart: In my feet.

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Monica Stewart: I would also say, like, think about, think about the length of your deal cycle, and then think about the phases of their decision process. So, like, phase one is gonna be…

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Monica Stewart: the executive sponsors, because no one's going to be able… no one's going to want to talk to you unless they feel like there's some sort of willingness to go forward with the conversation. So that would be first thing. And then second thing is, okay, once there's some level of interest from, you know, the people who are going to be able to say yes, then they want to know, is my team actually going to use this? So then you want to engage the people who are going to be your end users and get validation there.

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Monica Stewart: And then the third step is going to be, you know, non-BPO approval, so, like, finance, legal, and then you would want to start to engage those folks. Like, obviously, you're not going to reach out to finance after you have your discovery call.

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James Buckley: Yeah, I think reaching out to finance before you have the green light to reach out to somebody anyway, like, even if it's not finance, like, you can't… and this is a great segue into this other question that Samantha had that I wanted to talk about.

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James Buckley: you know, interested in stepping on toes. And, you know, this is the part where… Huge question. Yeah, huge question, right? Kristen, do you want to jump in first? I have a lot to say, but you guys are the experts in the room.

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Krysten Conner: Yeah, this is always the question, this is always the fear. So…

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Krysten Conner: number one, when we are not at power, that's why I like reaching out to executives early, because if we have… if the meeting is set, but we have not yet had the meeting.

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Krysten Conner: the… we haven't even met with them yet, so we can't… it's very hard for them to be a super gatekeeper if we haven't even had a conversation with them yet, right? And if they mention it on the call, I think we need to be prepared to calmly and not get flustered about it, but calmly have a conversation.

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Krysten Conner: To be like, where they said, you know, I think you emailed my boss, or I think you emailed, like, the head of HR,

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Krysten Conner: And…

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Krysten Conner: you know, very… the calm, like, response to that is, you know what, we have been reaching out to folks in your company for about the past 6 months, so I have been reaching out to Monica, you're a head of HR, James, your COO, and Alex, your head of finance. I've been trying to get in touch with, or I've been messaging them for quite a while, because we think we can help with XYZ.

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Krysten Conner: that getting executives involved early means your job can be much, much easier. So, that's something that… that we do to help people that want to bring this on. And while, you know, like I said, we've been reaching out to multiple folks in your organization, but we are excited to talk with you today.

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Krysten Conner: Right, so the understanding is, and part of that messaging comes from Jamal Reimer, super smart, where it sets the expectation that is, I have already been reaching out to specific people, I know their names, I'm excited to talk to you, and I won't just be talking to you.

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Monica Stewart: Monica? Yeah.

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Monica Stewart: Completely agree with all of that. Like, we… it's easy to forget that one of the superpowers that we have is that we are not bound by the same, like, political considerations and hierarchy as the people that we're selling to. Like, their boss is not our boss.

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Monica Stewart: And so, just like Kristen said, we know that we're going to have to reach out to and engage a certain number of people within that company, and we are actively engaged in doing that, and will continue to do so. And I think that helping them

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Monica Stewart: Feel bought in, and giving them the opportunity to be part of the process to the degree that they want to, or to the degree that they feel comfortable.

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Monica Stewart: Is really key here. And it's like, on the flip side, we're actually not doing someone a favor by saying, like, okay, we're gonna have a meeting with you, and then we're gonna throw all this information at you in a recap, and then we're just gonna follow up and say, like, did you talk to your boss yet? Did you talk to your boss yet? Did you talk to your boss yet? That's actually not creating a really good buying experience for our champion either. Like, that's

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Monica Stewart: we can't be asking them to do our job. And so…

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Monica Stewart: I love that approach at the beginning of the call. One thing that I will also do at the end of the call, once you've, you know, they've mentioned some names, they're like, probably the owner's gonna want to be involved, or whatever it is. Again, we've done our research, we've mapped the buying committee, so we know who those people are.

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Monica Stewart: And we can also then bring up names that maybe they haven't said, and we're like, oh, you know, it seems like because this is something that would touch your marketing funnel, your marketing director would probably also want to take a look at it. That's Kristen, right? Is her… I can go ahead and reach out to her and see if she wants to come to our meeting on the 23rd. Is that just kristen at outreach.io?

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Monica Stewart: Or whatever it is. And yeah, subtly letting them know, like, I know who the people at your company are, we know who we're probably going to want to talk to to get this deal done, I have their email address, I can send them a DM too. What is the best way to

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Monica Stewart: do you think for us to loop them in? Like, do you want me to CC you on that email? Or should I just, like, reach out to them directly? Should I mention your name? Yes or no? Totally up to you, but either way, like, that line of communication is going to happen.

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James Buckley: Yeah.

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James Buckley: Yeah, and he… Go ahead.

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Krysten Conner: I say there's two things, there's two additional points there. One is, the stuff I've been talking about, it's like, it's a bit easier to message this if it happens before the first meeting, but if there are folks kicking themselves down and going, gosh.

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Krysten Conner: I wish I'd done that, but now I have these people involved, and now I feel like I'm stuck at this level. One way, that…

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Krysten Conner: that you can successfully navigate around that. I call it the Bart Simpson, which is, remember Bart Simpson's line about, I didn't do it, nobody saw me do it, you can't prove anything?

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James Buckley: I only remember Eat My Shorts, that's the one that I remember.

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Krysten Conner: that too, that'll work too. But if you have your… if you ghostwrite a note for your boss to send to the executive that you want to reach, and your boss sends that note without you on the thread.

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Krysten Conner: That gives you some plausible deniability, if it does ruffle some feathers, to be like, where if, like, oh, well, your boss emailed my boss, you can say, like, oh, wow, gosh, that seems like that came as a surprise. You know, also, you know, those bosses, I really can't control everything my boss does.

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Krysten Conner: you know, just like you can't control everything your boss does, but executives reaching out to executives is something that happens all the time here, so that's probably why you saw that. Just, like, making that normal. And here's the… here's the key, like, caveat to remember, are people like, oh my god, what if this burns the deal?

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Krysten Conner: My mentor said something to me that is burned in my brain, which is, real deals aren't fragile.

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Krysten Conner: If one email, or one phone call, or one DM is enough where somebody just says, I'm walking away, they were never a champion. A point of contact does not equal a champion. If they're gonna walk away because someone sent an email.

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Krysten Conner: They were never an advocate for you to begin with.

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James Buckley: Alright.

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Monica Stewart: Go ahead.

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James Buckley: I love that. No, you.

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Monica Stewart: I supported.

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James Buckley: I'd say I've never heard that before.

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Monica Stewart: I just love that line that your point of contact is not a champion. Just because they agreed to take the first meeting, they were the first person in the company that raised their hand and said, I'll meet with you, does not mean that they have agreed to shepherd us through our 3-6 month deal cycle, and I think that that is…

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Monica Stewart: so important to remember when we start to get this anxiety that, like, oh, like, I don't want to step on my champion's toes. It's like, are you putting somebody in a role that they're not even aware that they have?

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James Buckley: Yo, we do that all the time. Now, we've touched about champions a couple of times in the last few minutes, so let's just get right into it. I wanna know, in the chat, have you ever had a champion give you the impression they were really pushing to move your deal forward, and you were working with them only to find out…

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James Buckley: Nothing that they told you was happening was really happening, and they are not a champion in any way, and they're actually kind of, like, lost on how to help you get this deal over the finish line. I think that this is the most common outcome when you work with a champion.

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James Buckley: for the first time, second time, and probably the third time, and then maybe on the fourth time, if you're lucky, you get it right. Anyone ever had that experience? Let's talk about it a little. Kristen, I think you had a lot to say about who owns the deal? The champion or you? Or is that you, Monica? I think you might have said, you know, who actually owns the deal.

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Monica Stewart: I did… I did talk about that, I think, and I'm happy to expand on it a little bit.

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James Buckley: Yeah, yeah.

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Monica Stewart: Yeah, I mean, ultimately, whose deal is this? Who is the person that… I mean, if you're doing outbound, or if you're doing inbound, who's the person who decided that this deal was worth selling in the first place?

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Monica Stewart: it was you, and you are ultimately accountable for the outcome. And so I think that, like, you know, there's something that's kind of seductive about this idea of, like.

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Monica Stewart: selling through a champion, because in a way, it makes us a little bit less accountable and, like, allows us to abdicate a little bit of the responsibility. Like, I've heard, you know, I've had sellers say to me, like, oh, well, we can't win a deal unless we have a good champion, and I'm like, well, that sounds hard. Like, you can only sell to companies where you're able to magically find somebody on the other side that's gonna…

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Monica Stewart: help get your deal done for you? How are you gonna hit your goal that way? And, I mean, I think the way to think about it is, like, your champion, if you're lucky, they invited you to the party. They put you on the guest list.

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Monica Stewart: But you can't,

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Monica Stewart: you can't, like, rely on them to… like, you're not gonna follow them around all night and only… only speak to people that they introduce you to. Like, you're in the room, this is your chance, go build relationships with the people that you need to build relationships with. And then, of course, you know, collaborate with them and develop your relationship with them at the same time, but, like, be a good plus one.

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Monica Stewart: And go and, like, you know, have your own conversations with people, is kind of the way that I think about it.

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James Buckley: That's not bad. And I appreciate the Be Your Own Plus One. I used to work the door at nightclubs in Miami, and people used to think that just because they were there in line waiting, that they were still going to get in. No, no. You have to be dressed a certain way.

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James Buckley: you have to have a certain amount of, you know, class about you. Those shoes are not acceptable in this club. Like, I had a lot of rules that I had to follow, you know?

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James Buckley: a count. We have a… like, I hold a counter, and then only a certain number of people can be in here at a time, right? So, I think the same thing happens. Just because I have a champion, just because I'm in the queue.

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James Buckley: Doesn't mean I'm gonna get to my stakeholders, doesn't mean I'm gonna get this deal over the finish line. Kristen, thoughts on your champion? How are you… how are you… how are you helping champions

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James Buckley: Pull your deals over the line.

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Krysten Conner: Yeah, I… in my mind, the principle here is,

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Krysten Conner: We have to teach them how to buy.

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Krysten Conner: Right? Just like Monica said, like.

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Krysten Conner: These people are experts in how to do their job. They are not the experts in how to buy our thing. When they became Director of Marketing or chief human resource officer, nobody laid a book on their desk and said, well, here's how to evaluate all the software or all the solutions that you will ever need. Nobody did that for them.

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Krysten Conner: And so, they… they need help, and it's like,

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Krysten Conner: There's a book called Into Thin Air by John Krakau that talks about summiting Everest, and the… and so I like to talk about us as Sherpas, right? Because, like, these elite climbers that go to Summit Everest, they are elite athletes. Like, they're smart, they're accomplished.

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Krysten Conner: And the Sherpa is the expert on that mountain.

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Krysten Conner: They… and it takes both. Could these expert climbers summit? Could they find their way? Sure. But is it much better and much more efficient to hire someone who has been there and done that a thousand times? Yes. That's the role that… that's the role that we should play.

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James Buckley: Steve put something in the chat here, Kristen, and when you were talking, and I think this is real.

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James Buckley: Those of you that have never thought of this, your champion could also be the champion for your main competitor.

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James Buckley: They could be comparing you, and you think they're your champion, but really, they prefer your competitor.

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Krysten Conner: champion for this… I mean, they could be the champion for a solution, right? Like, to getting this done. It doesn't… it doesn't mean, like… and I think different orgs define champion differently, and so I think you have to… you have to be really clear on what actually is a champion, like, in the organization.

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James Buckley: Well, with so many good questions, I'm gonna have a hard time not pivoting at this point to just answer as many questions as we can from the Q&A. Everybody's been really into this, which I love.

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James Buckley: So if you have questions you haven't asked, you've been teeter-tottering on it, throw them in the Q&A now, and you can upvote the ones that you like the most, and that's where we're gonna start. I think we talked about this a little bit when we talked about Samantha's question around stepping on toes.

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James Buckley: But let's talk a little bit about the risk of having a champion, coaching that champion.

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James Buckley: And then you reaching out to somebody who's their boss, right? Matthew Dosh, I think for me, the tip I would give you is, the moment you talk to your champion, you should be telling them who else

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James Buckley: that you are reaching out to, and then they won't feel surprised, there won't be a blind side. Do you do this, Monica? I see you shaking your head.

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Monica Stewart: Yeah, 100%. So, I think that, you know, part of good communication across the entire organization is not just… you're not just having, like.

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Monica Stewart: one conversation with this person, one conversation with this person, one conversation with this person. Your goal is to…

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Monica Stewart: create these multiple threads, and then weave the threads together into your little spider web of the deal that you're creating. And so this includes, you know, this includes horizontal alignment, and it includes alignment, like, both above the line and below the line. So, you know, I gave an example earlier of, like, doing use case workshops, and then giving that feedback back to

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Monica Stewart: the executive sponsors, so that they hear, like, real things from what their team is struggling with and where they see value, et cetera, et cetera, et cetera. You know, same thing when you're reaching out to people at the user level, you should let them know, like, I have been talking to your director of marketing, and they're interested in this because they think it'll make this easier for you guys. And then same thing when you're talking to your champion, you're always keeping them up to date on all the conversations.

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Monica Stewart: that you're having. Like, I talked to this person, they said this, I talked to James, he said this, and then the one person that I haven't been able to get ahold of yet

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Monica Stewart: is Steven really interested to ask him these questions based on what everybody else said, like, what do you think?

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James Buckley: Yeah.

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James Buckley: There's probably some level of…

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James Buckley: courage that it takes to be able to push the envelope here, and MH has a good question that is right on line with, like, that courage that it takes.

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James Buckley: To push that, and to really be transparent with what you're doing early in the conversations. What if… and this, Kristen, this is probably one that happens to you, I'd imagine, frequently. Probably happens to both of you, and I know it's happened to me.

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James Buckley: I'm okay with you reaching out to this person that's above me, but don't tell them that I said you should reach out to them, right? Like, this is like a break in the multi-thread, right? It's almost like there's multi-threads happening, but this one over here, it's dead, it's broken, right?

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Krysten Conner: I mean, I think it's more, like, indirect. So in that case, one of the things I like to do is say, okay, happy… yeah, happy to go and speak to the executive. It sounds like this is a problem. One thing that would help me is if you could tell me the names of two or three of your peers that are experiencing the same problem

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Krysten Conner: that you are. That way, if I talk to them quickly and just validate that this is a thing that multiple people are seeing, then it also helps anonymize it whenever I go to your executive and say, I've talked to people on your East Coast team, your West Coast team, and your LATAM team, and they all seem to be experiencing the same problem.

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Krysten Conner: That can be helpful, right? And if it's, like, you're helping… they can help you strengthen the case without them having to be named personally, because, like, if you're a rep, think about how comfortable you would be if you tried… if you took a look at a technology that you think would be super helpful, and they're like.

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Krysten Conner: okay, and I see that Alexa is your CRO. Can you go ahead and introduce me? And you're like, Alexa wouldn't know me from Adam. Like, I don't… I'm hoping to meet her at our SKO, you know? Like, how comfortable

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Krysten Conner: could you be with that? But you're like, but hey, use all the talking points, right? Go validate this. That is not… that's really valuable information to have. I think we just have to know what to do with it next.

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James Buckley: We have to know what to do with it in a tactful way.

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James Buckley: And the tact here can't be overstated, right? There is a level of professional courtesy we display when we are multi-threading appropriately, and a level of, like, carelessness when we're not. And that's an important distinction to make, because at that point, you've crossed over something that could potentially ruin your reputation, or even worse, get you blacklisted at some organization that.

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James Buckley: You know, you potentially may have lost your year there.

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Monica Stewart: I actually… I prefer to speak to… to Kristen's point, to the problem, and not… I prefer to not use personal references as much as possible.

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James Buckley: Really?

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Monica Stewart: Because it's tricky, because we don't know how closely people in large organizations work together, like, you're the GM of the West Coast office, and you're the GM of, like, Benelux.

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Monica Stewart: how often have you ever interacted? Like, maybe once, at an all-hands? And then the other thing is, is you never know what someone's reputation is within the org. And so, you might be like, I talked to Jeff, and he said that this was amazing, and this is exactly what they need, but then maybe you would go and reach out to other people on the team, and they're like, yeah, Jeff has that problem. But, like, yeah, we all know about that. That's, like, his thing. And so, it's… I prefer to validate the problem and not

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Monica Stewart: Rely on, like, the personal connection.

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James Buckley: That's fair, and I can… I can…

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James Buckley: I can tell you that I've lost many deals I thought were a shoe-in because of that personal connection.

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Monica Stewart: Great.

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James Buckley: And, you know, that's where Happy Ears kicks in, and multi-threading is like a feeder for Happy Ears. Each time a new stakeholder engages with you, as a seller that is very energetic, you get very excited about that. You're like, oh, this is moving, right? But, again, no guarantees. I'm at the door, I'm checking the boxes, right?

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Monica Stewart: Maybe an hour. Yeah.

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James Buckley: Yeah, this is a good one from Matt Webb. When the op is ice cold, is it a best practice to let each contact know that you've also reached out to the colleagues? Pros, cons on this? I think it's different when it's cold. Any thoughts on cold multi-threading from the two of you?

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Krysten Conner: and let's define ice cold. Does that mean, like, you… it's cold outbound, or does that mean it has gone cold?

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James Buckley: I think Matt is saying cold outbound, so multi… yeah, he got it in the chat. Matt is saying cold outbound.

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Krysten Conner: Okay, is it best practice to let each contact know you've also reached out to their colleagues? Yeah, I would say, I would say yes, and here's why, especially if you're dealing with organizations that I would say, like, 200 person plus.

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Krysten Conner: the larger the enterprise, the less likely it is that the left hand knows what the right hand is doing. Yep. Right? So, when I was selling to school districts, and these were, like, 50,000 person school districts, their, person in…

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Krysten Conner: their onboarding for HR, and their curriculum director, like, I have a solution that would help both of them. They hardly ever cross paths.

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Krysten Conner: But if I said, this person is looking at this solution, they have this use case, you have this use case, and typically what customers do in this situation is they both evaluate to see if they can combine their budgets to get something that would help them both.

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Krysten Conner: You have connected dots within their organization, and that is actually one of the biggest

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Krysten Conner: value adds that you can do in larger organizations is how… you would be astonished how little contact there is between department heads

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Krysten Conner: Even in organizations as small as, like, 200 people. So, it can… I mean, I can't tell you the number of times they'll be like, oh, we had no idea they were evaluating anything like this. I will go talk to them.

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James Buckley: We all have Slack, but not everyone uses it.

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Monica Stewart: I would also say, right, which also just goes to show that if you think that, you know, people that you're talking to are, like, talking you up within the org like they're not. I would say that if you're doing full cold outbound and you haven't had any conversations with people at the company yet, in that case, I personally would not mention it.

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Monica Stewart: For… it's kind of like a tragedy of the commons problem. They're like, oh, they're also reaching out to these 20 other people, I'm sure someone will respond. And then also, like, I prefer to keep the conversations…

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Monica Stewart: siloed until I have enough information that I have something of value that I can take to other people and be like, hey, this team is looking at this for these reasons, and I thought that it would be relevant to you because of this, and then I'll go and, like, jump over the fence and go talk to the other group.

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James Buckley: Yeah, it is, you know, there are triggers that let you know it's okay to go and move forward and talk to someone else, and I think if we're paying attention.

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James Buckley: we'll be able to pick up on those triggers really well. Alright, here is a quick recap for everybody that is interested in seeing the recap here. A lot of people reached out to us, they say they want to see quick recaps at the end of the show. The one that stands out to me here is not to rely on just one champion, and of course, start multithreading before the first meeting. If you guys, if you ladies had to choose

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James Buckley: one or two that stood out to you, what do you got for everybody?

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Krysten Conner: These are all really good. I would say,

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Krysten Conner: don't rely on just one champion, and get that executive alignment early. I think if you are selling to multiple stakeholders with deals of, like, over 3 months, like, that's gonna be critical.

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James Buckley: Yeah, yeah. Monica, which one crawls out at you?

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Monica Stewart: I would say, map the buying committee early, definitely get that early exec-to-exec alignment, and then one that we didn't get to talk about a lot is building your selling committee. So just remember, Kristen talked earlier about having your boss reach out to their boss.

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Monica Stewart: Think about… think creatively about all of the different people on your team that you can have reach out to people on their team, right? So, like, do you have a partnerships program where you work with agencies? Can you have, like, your agency contact reach out to somebody that's on the implementation side and talk about rollout? Just, you know, the more people you can have.

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Monica Stewart: And the more people you can have on their side, the better it's gonna be.

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James Buckley: Monica and Kristen will be back to talk more about multi-threading and possibly mapping out your buying committee. That sounds like a show unto itself. I don't know what happened there with that image, but check us out, sellBetter.xyz, you will all get a survey. Let us know what you liked about this show, what you want to see more of. Once again, shout out to our newest partner over at Quotivity, and our friends at ZoomInfo for making this possible. We'll see everybody right back here tomorrow for another stellar episode.

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James Buckley: of Sell Better. Have a great day, everyone!