


27 Aug 2026 · 42m · 12 chapters

Enterprise deal acceleration by partnering with executive assistants (EAs), validating the executive sponsor/champion, and mapping both the visible org chart and the “power base” (influence network) to manage blockers.
Laura McDonald is a three-time President’s Club winner who sells technical analytics/data products to very large enterprises (about 20,000–30,000 employees in her patch). She focuses on consensus across buying committees and long enterprise sales cycles.
Prospecting via LinkedIn “People” tab to find EAs by title; build EA relationships first and CC the EA; use “two birds with one stone” questions to confirm the exec sponsor and whether the EA/champion has access/influence; map org chart with a champion using Miro; identify whether blockers are “savable” and whether they can veto; neutralize blockers with technical resources or crowd out their influence.
She recalls losing a deal by overlooking a lead analyst who had a strong personal/professional relationship with CTO/CIO; she would have mapped earlier and “baked brownies” for that analyst/EA to build access.
Written by AI. May contain mistakes.
Learn effective strategies for reaching out to executive assistants in sales prospecting.
“How are you finding the EAs that you're reaching out to?”
Laura McDonald shares her top strategies for engaging with executive assistants.
“Okay, so number one, two birds with one stone.”
Explore how to locate and connect with executive assistants effectively.
“Navigating the org chart with your prospect.”
Understand the components of a compelling email to executive assistants.
“How are you finding the EAs that you're reaching out to?”
Learn how to handle follow-ups and different responses when engaging with EAs.
“and like, it's not like a burden on them.”
Learn effective strategies to nurture relationships with executive assistants.
“And you, with the executive assistants, too, I think you've mentioned, like, they're pretty overlooked.”
Discover how to leverage relationships with EAs to gain access to executives.
“to give you an advantage over competitors, help accelerate the deal, give you access to people you might otherwise not get access to, because you're putting all this effort into these people.”
Learn how to map both the formal and informal structures within organizations.
“And you can't really tell that second one from LinkedIn or anywhere else.”
Explore strategies to identify and address blockers in sales deals.
“We're a little shy of 30 ,000 people just a touch, but, you know, so we're probably out of segment for you.”
Learn how to identify and deal with blockers in the sales process.
“there's a, we talk a lot about with them, what's in it for me.”
Explore strategies for handling champions who may not be effective.
“We got to this point in the deal, and I was like, anything, it's like, no.”
Learn how to ask better questions during sales presentations.
“They're not just the most important person to be a champion.”

Get the gist, explore an idea or ask about something said.
On 30 Minutes to President's Club | No-Nonsense Sales, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Prospecting via EAs. How are you finding the EAs that you're reaching out to? Are you just typing in EA General Electric? Are you using Sales Nav? Give me a sense of like how you find the list. It's really simple. It's just the LinkedIn company page on normal LinkedIn, not even Sales Nav really. And in the people tab, I'll just type Executive Assistant to the whatever executive I'm trying to get to, to the CIO, to the CRO, to the CEO, whatever. Usually they'll come up straight away and it will say in their own title who they are. If there's just like 10 general EAs and I can't work out which one's which, I'll just pick one that looks the most senior and I'll email them saying, hey, I'm looking for the EA to Sarah, the CIO.
0:40And then I will put in like two random EA names. Is it Jane or Mike? Because you know, there's that reverse psychology on people want to correct you if you've got it wrong. And so I'll do that and usually I get a response and they'll say, oh no, it's so-and-so. And they'll often CC them in as well.
0:58Good morning, everybody, and welcome to this episode of 30 Minutes to President's Club. I'm your host, Nick Segelski, with my co-host, Alex Murphy. And today, we have a not one, not two, but three-time President's Club winner, Laura McDonald. Laura is a freaking badass. She sells to massive companies. Literally, her patch is between 20 ,000 and 30 ,000 employees. And she is selling a fairly technical data product. And so if you are sick of all the content that's just sellers selling to sellers, giving sales advice, you're in luck because this is not that. And this is a phenomenal episode. Alex, why should people listen?
1:36We could have done 60 minutes of President's Club on this one, honestly. And, you know, we get into really nitty gritty on how to get to consensus across a whole buying committee. So Laura Brooks broke down how to do executive assistant outreach, how to leverage EA relationships, how to really pressure test champions, understand the entire buying committee, deal with blockers, all this stuff that is hitting me every day in my sale. And I found the takeaways super, super tactical, and I'm going to go use them. All right, Laura, welcome to the show. We start every single episode with your top three actionable takeaways.
2:12So let's get your three. Okay, so number one, two birds with one stone. And I'm using this to validate two things. Do I know who my executive sponsor is? So I sell analytics solution, our exec sponsor is usually the CIO or the CTO, and validate as is the person I'm talking to a potential champion here, access and influence over said exec sponsor. Now, I will do this usually on my first call with a prospect, not a quick disco call on a cold call, but like the first proper meeting. And I'll research on LinkedIn using the people tab who I think my exec sponsor is going to be. And I will get their name.
2:49And then when I'm meeting with my prospect and they're telling me about their initiatives or their current tooling, I'll thread in questions like, say, the CIO is called Sarah. I'll say, hey, what does Sarah think this initiative needs to deliver for the organization? And the reason I say Sarah and not Sarah and surname is also to make it sound like I actually know Sarah. And then the prospect doesn't kind of question me on why I'm asking about their leadership. And their answer will tell me two things. Either they will correct me and say, no, this isn't under Sarah's org. It's actually Jeff's org on the CAIO side of things who's sponsoring this.
3:25That's clue number one. And then whatever their relationship is with this executive will also give me a clue. So they might say, oh, yeah, in our weekly one to one with Sarah. And then I know that this person is high enough up and valued enough by Sarah that they actually have a regular meeting with them. Amazing. Well, I like the animal friendly version of feed two birds with one scone. But Laura, why don't you take me to actionable takeaway number two? So this is my favorite one, which is building a relationship with the executive assistant first. Again, I'm in the enterprise team at ThoughtSpot.
4:00So I'm selling to companies of 10 ,000, 20 ,000, 30 ,000, 40 ,000 employees. And usually the executives at the C-level, their EA manages their calendar, their agenda, their priorities, and who they're meeting with. So I want to build a relationship with that person first. So I might do this as just pure cold outreach, PGing into an account. I'll PG into the EA first if I want to get to that executive first of all. so again I'll go on LinkedIn I'll search EA to the CIO usually they have that title in their profile and then I will send the EA a personalized outreach email so I'll have a personal thing at the beginning something I've researched about them and then I will have a full-on proposed agenda little briefing about who my executive is that I want to connect them with what the outcome of this meeting is intended to be and maybe some time suggestions as well and then I will usually also CC in the EA to my executive.
4:57So it again, just adds even more credibility to this meeting proposal. I love it. Round us out, Laura, what's number three? Navigating the org chart with your prospect. And this is both to understand the actual org chart and also what we call the power base, which is the kind of invisible political org chart behind just who's who on paper. So what I'll do, and I'll do this once I've established an actual champion who I have a good and trusted relationship with. I will build in Miro the org chart for the different teams who I know I need to sell my product. So at ThoughtSpot, we call this a three-legged stool.
5:31We know we need kind of tech, data analytics, and business to be able to sell our product. So I'll build this all out. And then I will literally screen share with my champion and ask them to help me navigate and ask them to advise me on, hey, have I got this right? Are these people in the right place? and many other questions on top of that as well. All right, so I want to go deep on this prospecting via EAs stuff that you're doing because we've had almost 600 episodes of 30 MPC right now, and I don't think anyone has ever covered this before. So let's talk about first how you are finding these people.
6:09Are you just going on LinkedIn? You talked about using the People tab. How are you finding the EAs that you're reaching out to? Are you just typing in EA General Electric? Are you using Sales Nav? of give me a sense of like how you find the list it's really simple it's just the linkedin company page on normal linkedin not even sales nav really and in the people tab i'll just type executive assistant to the whatever executive i'm trying to get to to the cio to the cro to the ceo whatever usually they'll come up straight away and it will say in their own title who they are if there's just like 10 general eas and i can't work out which one's which i'll just pick one that looks the most senior and I'll email them saying hey I'm looking for the EA to you know Sarah the CIO and then I will put in like two random EA names is it Jane or Mike because you know there's that reverse psychology on people want to correct you if you've got it wrong and so I'll do that and usually I get a response and they'll say oh no it's so and so and they'll often cc them in as well assuming you found the right person you talked about like what is in that message that you send to them.
7:18Can you actually give me an example of what you would write in that email? Because I understand you're telling me the components of that message is an intro of who you are, research you did on the EA, why you're reaching out, and who you want their exec to meet with. I guess break down the outbound message you send to the EA for me. Yep. So the first part, just as we would do with any other prospect, I'll say something personal, whether it's, you know, we went to the same university or, hey, I see you're interested in whatever animal welfare, just like a little nugget that I can get from their LinkedIn.
7:51Because I think a lot of the time the EAs are, they're kind of in the background. People don't treat them with the respect they deserve. Like they don't just, you know, book meetings for their exec. They are such a strategic partner. So I always want them to make them feel like, you know, I'm interested in you as well as the exec that I'm actually trying to get to. So something just personal in the subject line. And then I'll say like, this is a meeting request for your CIO, Sarah Murphy, to meet with our chief data and AI officer, Cindy Housen. So just upfront what it is. And then I'll say like a quick reason why.
8:30So reason being, your company is investing heavily in whatever AI and analytics. Sarah recently spoke on XYZ podcast about this subject. this is what our company helps xyz of your competitors do and cindy howson over at thought spot is a strategic advisor to our customers on these topics uh seems like a timely um you know moment for them to connect have a conversation and then i'll put proposed agenda and i'll just put three bullet items like you know discuss your ai strategy this or this learn about how thought spot is helping companies deliver this and achieving xyz outcome align on next steps for whoever Sarah wants us to work within her team.
9:12Time and date suggestion, blah, blah, blah. In copy of Cindy's EA, et cetera, et cetera. Thank you so much in advance for your help. When you first said this, I thought, man, an EA is probably going to delete a prospecting email faster than you can blink. My perception is a lot of EAs are just full on, I'm protecting my executive's time. We're not worrying about all that. But what you're really doing here is offering to facilitate a principals meeting between them and their counterpart. And there's, you know, we talk all the time about like, you need to sell the meeting, the meeting itself needs to be valuable.
9:42I would assume some of the value there is there's like a networking thing happening. Hey, our CIO at this big, we're a big shop. You're a big shop. Do you want to talk to get talk AI strategy? Like, you know, that is, I would say, I'm assuming that's pretty compelling. And you're like looping in the, the, the EA on your side as well to kind of demonstrate like we're serious I am curious how are you setting expectations with your executives executive assistant on like hey you're gonna get some emails from me you're gonna get cc'd on those they're not all gonna get responded like what does that conversation look like so on we use slack here at thought spot so I have a little section in my slack you know like organized channels which is tseas so I just have one-to-one slacks with all of our exec eas and so So I'll just ping them saying like, hey, you're in this email, no need to respond.
10:35Like I'm waiting for the prospect to respond first. So just giving them a quick heads up so that they know they're not weirded out and like, it's not like a burden on them. So they know that you do this. Oh yeah, yeah. I'm curious about if you can help coach us through the types of responses that you get. I'm sure there's some, you don't get a response at all. So I'm curious what follow-up looks like. Are you cold calling the EA? Are you sending follow-up emails? Are you hitting them on LinkedIn? in? Are you mailing a package to their office? Then I'm curious about rejections, pushback, objections.
11:06And then I'm also curious about when they do say yes, how that typically plays out. Maybe we can start with the least appealing response, which is total and utter silence. What does your follow-up look like? I will cold call the EAs as well. Like I'll use whatever tool we have, Zoom Info or whatever, to get their number from LinkedIn. And I will cold call them. Just as I would do with anyone, you know, hey, I sent you this email. Do you see it blah blah have you forwarded it um and usually the a's are really nice people they don't get cold called a lot either so it's not as if their phones are blowing up all the time with sales people trying to call them so it's not as you know angry a response as sometimes it can be when you're cold calling people get cold called all the time and then it will just go into normal follow-up like if they haven't forwarded it yet i'll just say oh you know just polite reminder and i'll just mark in my calendar to call them again in three days time for example i usually leave about three days when dealing with execs just we all know they're so busy they have so much on their plate i don't want to be seen as that person calling them every single day at the exec and the ea level so i usually do two to three days wait time if i'm just not hearing anything um obviously if like weeks go by and i haven't got anything back then i'll probably just use the same email template tweak it a bit and just send it to the exec if i get a response which is like hey thanks for your email lovely to meet you I forwarded this to Jim we'll let you know what his response is again I'll say thank you so much and I'll leave it two or three days and then just follow up did Jim get back to you any ideas and then either they'll say yes we want to have a meeting and then obviously I can coordinate it from there the other response that I'll sometimes get is Jim is too busy to have this meeting but he would like Cindy to meet with x person and so you get a natural bounce which is always arguably even better because it means that the exec knows exactly the person who is running these kinds of initiatives and so you're introduced to arguably who might become your champion at the end of the day in that scenario so you've gotten bumped down a level are you still connecting them with your executive or do you also go down a level and bring in whoever the the counterpart is like what's your move right there It depends who.
13:19If we're talking a Fortune 500 company and the CIO has bounced me to their SVP of data analytics and AI, that's still a pretty important person. So I'll probably still keep the same exec on our side. if they bumped us way down into like senior director or something yeah I'd say I'd ask Cindy hey who on your team should should meet with this person just so again it protects me so that then later on I can have Cindy send a note to the exec saying you know our team's met had a conversation about this you know really exciting sounds like there's a next step looking forward to connecting with you later down the line so I always want to maintain like enough space between the right people so that later in the sales cycle, I can bump back up to the exec in a natural way.
14:09Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed 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, This Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist.
14:36Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't? And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now, we built a toolkit with our friends in Ambition on how to actually use data to coach your team.
15:02Get it for free in the show notes. Today's show is brought to you by Pipedrive's easy-to-use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple-choice question, which sounds like typically when I'm talking with folks like you, they're focused on A, B, or C. Which is it for you? Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes.
15:30And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes. Yeah, amazing. Amazing. And you, with the executive assistants, too, I think you've mentioned, like, they're pretty overlooked. Oftentimes, people are sort of like, get out of my way. I'm trying to get to the executive. Is there anything else that you do for, like, because you're running enterprise sales cycles that are probably quite long. I imagine it's not a one-time interaction with this person. How are you keeping that relationship fresh? Because they may be in the meetings, maybe not.
16:00How are you nurturing that relationship over the course of a whole sales cycle? Yeah, I wish our sales cycles were short, but that's definitely a place. It's a mixture of things. So I will treat them just as kind of anyone that I want to build a good relationship with. So that looks like every Thanksgiving and every Christmas, I will email all the EAs I work with, even EAs who are in a company that we didn't sell to. Like I have a list in my big Excel PG spreadsheet, which is it's a tab that says EAs and it just has who they are, their email, who are they the EA to? And then I have like notes about them.
16:38Oh, they're interested in this. They have two kids. They are really good at answering the phone, blah, blah, blah, blah. So I just keep that kind of memory bank. And then yeah, every Christmas, every Thanksgiving, I'll send them an email. well, thank you so much for all you do to help. I know your role is extremely complicated. So thank you for prioritizing our agenda, blah, blah, blah. Every onsite I go, well, not every onsite, but if I'm meeting their executive and I'm bringing some kind of personalized gift or I bake. So a lot of the time I'll bake like brownies and bring them to an onsite.
17:11I will always ping the EA saying, hey, I'm going to be onsite at this time. I'm bringing brownies. Would love to give you one. and then I'll you know I'll give them a brownie so just those little things to make them like understand I know how valuable they are and how important they are and then the more practical things like if we've had a meeting with their executive that they helped facilitate I'll loop them into the follow-up I might send them a one-on-one saying hey had a great discussion with Nick thank you so much again for helping facilitate blah blah blah are there other ways that you are leaning on the EA during the deal cycle to give you an advantage over competitors, help accelerate the deal, give you access to people you might otherwise not get access to, because you're putting all this effort into these people.
18:02And I know this is not just altruistic of you want to give away brownies so you don't eat them all yourself, although that's what I end up doing. But I'm curious about how you then leverage the goodwill that you have generated other than just being a good person. Definitely. I mean, it's always I want to be first in line to get time with the executive. So it's kind of like with a champion, like I want to make the deposits first and build that relationship and have that trusted bond between us. But then if ever I need time with the exec, I know I can ping the EA saying, hey, I really need 15 minutes for Nick to meet with Alex on our side.
18:40Can you help us find time this week or next week or whenever it is? So it's usually about just getting time on the exec's calendar. And I mean, 99 % of the time, it works. Like if I put this effort into the relationship, we always get time with that person. And you also know that behind closed doors, if they're talking about, you know, the vendors that they work with, you know, that the EA is also going to give their opinion. Oh, I love working with Laura. She's great. She's like good follow up and professional and blah, blah, blah. And she bakes nice brownies. it's also about like all of those channels into the exec like who is speaking well of you or i'll ping them saying you know has so and so got any upcoming holiday if we're like trying to work on getting a contract done and i know that the site now and i need to know are they in the states or are they in india over the next two weeks and it's going to be really hard to track them down yeah this actually kind of transitions into one of your other takeaways which is like mapping the org.
19:37And I think you, you've got the, I really liked the framing of there's the org chart and then there's like the shadow org chart. There's the power base, like who's actually working it. And you can't really tell that second one from LinkedIn or anywhere else. So maybe I'm curious, like, would you walk us through, like, how do you actually structure that conversation? I understand you're like displaying an actual org chart that you write out. what is the key info you're trying to get? And when do you deploy that? Like you've, I'm presumably you've got a champion who is now like partnered with you.
20:10So like, how do you frame that conversation? And then like, what are the questions you're actually asking during that? Yeah. And the power base, um, I didn't adopt that term. So, uh, it's actually a book called the power base, which I recommend everyone to read. It's on Amazon. One of my great friends and sales mentors recommended it to me and yeah it totally changed how I think about the org and then the invisible org and as you said it's once I've built a relationship with a proper champion and we trust each other and then you know that obviously they're invested in bringing your solution in as well so they are going to help you and so once I've got to that point you know regardless of when exactly that is in the cycle I will build the org chart myself in my row I'll just use LinkedIn.
20:55I'll just research the types of people who I know are needed to sell ThoughtSpot to. Do we have the analytics team, the data team, the different business teams? Who are the execs that I know are going to need to sign off on this? I will build that out in my row. And then I will have a call with my prospect and say, hey, I feel like we're not with everyone who's needed to buy ThoughtSpot or sponsor bringing it in. Can I just walk through my perspective on the org chart and you can let me know if I've got this right. And we can just talk about who else we need to bring on board. And then it's just, I'll just share screen.
21:30And the first question I ask will just be, hey, have I got this right? And they will say, no, so-and-so reports into so-and-so. So-and-so got fired last week. They're not here anymore. They'll rearrange it for me. And then I'll go deep into, okay, we need to get the VP of data platforms on board. I have no relationship with this guy. You know, what's he like? Does he know about this project? Is he attached to the current tool? Et cetera, et cetera, et cetera. So I'll do that for each person who I know is important. And, you know, they'll advise me on different things. And then that can spin off into a number of actions.
22:08Like if it's people that our champion is friendly and has a good relationship with, of course, the next action is, hey, can you broker an intro so that we can meet with them and start to bring them on board? If it's someone who is really going to be a blocker, then I would have a conversation about, okay, how typically have you got around this kind of scenario when you've brought in technologies in the past? Or who does this person listen to? Maybe it's some random engineer in their team. You haven't met, but this is back to the power base. Like, you know, some people can be really low down on the org chart, but they are actually really a trusted advisor to someone else.
22:43So then you can kind of get some actions around that as well. it's always that person with like nine years at the company whose title doesn't make a ton like you're like what is this title and it's like oh yeah that's just like the person who just knows where all the bodies are buried and like kind of has the ear of the executive that's i mean not that you might not have title you know your title might go up but like yeah i know if i want to go change armand's mind on something i'll like say alex you know you should mention this to armand the next time you exactly you won't listen to me laura now you know how to sell us thought spot so So there you go.
23:14We're a little shy of 30 ,000 people just a touch, but, you know, so we're probably out of segment for you. Well, I mean, listen, we but we do this, too, though, like we use a different tool, but it's like a virtual whiteboarding tool. And this is exactly it. We we have a two legged stool. You know, so I sell our training and enablement partnerships. And in order for that to go, you have to have enablement. You have to have sales like you have kind of have to have them both on board with this. Sometimes you start in one spot and you need to get to the other. So like, I would assume that's the same for you is the way in is not always the same.
23:44But then like you do need that like stability of multiple people buying in. And like, I wonder how many deals I've lost where I didn't do this and I didn't understand. It just fell through like so often when we lose a deal. It's like, I don't know why. I don't know what happened. Something's weird. Something changed, but I don't know what it is. I would imagine you're not feeling that way too often in the cycles where you're having these conversations. If I'm doing this really well, then no, you just feel so much clearer. It's like being underwater and putting gobbles on, you know. And sometimes we forget to just ask our champions for this kind of help.
24:19Like we're sitting there in a deal review and we're being asked, you know, have you got this stakeholder on board and what are they thinking about it? And you're like, well, I don't know. I don't know what they care about. And it's like, this is what champions are for, is to ask them to help you with this kind of stuff and doing it early as possible. I think, you know, deals I've lost and things like this, I've done this way too late. And the competitive champion has been way stronger or we didn't identify. Like I literally lost a deal once. I remember when I was in ThoughtSpot UK, we had CTO, CFO, like CIO all on board.
24:53We had their leadership on board. And there was one like lead analyst guy who I'd kind of overlooked. And And he had such a strong relationship with the CTO and the CIO at like a personal level, a professional level. They'd worked together for years and years and years. And I didn't think he was important. And that was a big lesson in like this whole power-based thing and just mapping out way earlier and not thinking I know like who's important in a company just from a title. Should have baked him some brownies. I mean, just give you got to leave those guys some brownies. Could have been a whole different ballgame, you know?
25:31I should have done. Yeah. Laura, let's assume you had a chance to rework that deal. And let's say you're working with Alex here. Alex is your champion. You pull up the whiteboard and Alex tells you, hey, this analyst over here is going to be critical. And I think they're a blocker in your deal. If you could get a redo on the deal, what action would you have taken to save that deal? So I would have firstly wanted to understand why. So I would have asked, why are they a blocker? What don't they like about ThoughtSpot? What are they hesitant about? And I think a lot of the time there's maybe job fear.
26:09You know, people have done the same thing with the same tool for a long time. They don't like change. They are strategically placed within the company because they know how to use the existing tool.
26:20Laura McDonald: And that's when it runs off. So it's usually more of a kind of personal thing. So I'd want to find out the why, first of all, from my champion. And then I would ask, you know, are they so far onto the blocker side that they are literally, you know, best friends with the AE on my competitive tool? Like, are they unsavable or are they are they savable? Because that also determines what actions you take. Most of the time, I think they're savable. And so then it would be, OK, what does this person care about? What motivates them? What do they love about their job? What do they hate about their job?
26:56and after I've understood all of this then I would think about okay who from my side can I get on maybe a one-to-one with them where I'm not in the room because you know what it's like sales can be seen still as negative and salesy and then some people don't like that kind of persona on cause so if it's like a super technical person like this guy was I'd get one of our like really techie not even solution engineers like principal solution architect kind of person yeah who can go like super deep on on these kinds of topics and I would get them to reach out to this person either over email or if we have a joint Slack channel with the customer and I would phrase it in a way of like hey you know I know you're not very happy about xyz part of our platform we're thinking of improving it in these ways I'd love to get your opinion on this so something like that to just get them to open up and just get on a call and then that's how I'd kind of start trying to break down their walls and show them like, hey, there's value in this solution for you.
27:59And we want you to, you know, be a partner with us here and make them feel like there's a, we talk a lot about with them, what's in it for me. And so it's all about finding out what is that for that person. And then how do we help bring them out and show them that ThoughtSpot can help them achieve whatever they want to achieve. Let's talk about the other route. So you find out there's a blocker, you figure out why they're a blocker, you ask if they're savable or not, and they are not savable. What is your plan of attack from there? Then I think, shit. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal.
28:36When 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 3x. 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 Ambition, the coaching and performance platform helping sales leaders turn metrics into action.
29:05Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't? And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now, we built a toolkit with our friends in Ambition on how to actually use data to coach your team. Get it for free in the show notes. Today's show is brought to you by Pipedrive's easy-to-use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple-choice question, which sounds like, typically, when I'm talking with folks like you, they're focused on A, B, or C.
29:38Which is it for you? Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes. And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes. Laura, this just, just happened to me. We got to this point in the deal, and I was like, anything, it's like, no. And this person is absolutely, has the power to veto it, and they're unsavable.
30:09And that's what I was wondering. Do you just kind of go like, all right, well, going to focus elsewhere? I mean, no, ultimately, I won't give up that easily. But then I'll go into understanding, okay, how much influence do they have over people that need to say yes, the C level or whoever else like they, are they a blocker that's just going to be annoying when we do an implementation? Or are they a blocker that actually is going to tell our exec sponsor, do not buy ThoughtSpot. So I want to understand again, like what level of blocker even are they? If they're the latter, which is like the red zone, then I mean, I'll also ask my champion is like, is this a lost cause then?
30:47Should we even continue running our POC or whatever and get their advice? And I'll also ask, okay, who else has influence over CIO Alex? Because if there's, you know, four people that he really listens to, one of them is a blocker, then the natural next step is, okay, these other three, are they engaged with us? Are they potential champions? Are we building a relationship with them? because then in the room that we're not in at the end and it's three against one, then our blocker is going to be overruled. So I'll still try and find out again, like what kind of blocker are they? How bad of a blocker are they going to be?
31:22And then are there other people who can override the blocker just in pure numbers wise and equal levels of influence over the EB? Yeah. I'm curious about all of this depends on having a champion who knows what's going on, can answer the questions, can get you in the right room you mentioned one of your takeaways was the two birds one stone whether we're feeding them a scone or slinging it at them one way or the other what do you do like if you're a little bit deeper into a cycle and you start to realize like your champion's not really getting it done for you how do you handle that wow you do a whole podcast on that um i could use it that's the place where you really don't want to be but i think firstly just in terms of how do i know i'm suddenly with someone who i'm doubting whether they're a champion i mean it will show up in things like if you're asking them to help you with something and they stall on it or they won't do it or they say they will and they they never actually do it um if they won't introduce you to other people is one of the biggest red flags i think um so there's the signs like that along the way which can start sending off kind of warning bells in your head um so a couple of things firstly i will want to get away from that person as quickly as possible because i think we've all been there i've been there when you you've like built a relationship with someone over a few weeks and months and you it's like kind of hard to just stop talking to them it's like the seinfeld episode when he's dating the one woman and he wants to date a roommate instead and they stay up all night going how do we pull this off where you can you know like date the room like that's tough to do it's awkward it's kind of awkward and often this person is still going to be involved in your deal.
33:06They're still important. They're not just the most important person to be a champion. So I'll just pretend, you know, everything's fine. And, but I'll start asking them questions like if, and if I haven't done this already, I'll do things like say the CIO is called Alex and I want to find out like, okay, who else does Alex listen to? I'll say, okay, Nick, when you're in, you know, your meetings with Alex kind of talking about these kinds of analytics initiatives like who else is in the room with you and then they'll wheel off you know some other random people and then i'll ask oh cool okay so you mentioned um nick like what's their involvement with analytics and so i'll just start again doing discovery on other people in in the org around them um and then i'll either do one of two things like if if they know the these people and they have a good relationship I'll say oh it's it's kind of weird like you said this person also is responsible for analytics projects but how come they haven't been involved in our conversations and then they might say something like oh well you know they don't get involved until you know much later in the cycle and I'll say okay but um if they're going to be part of the decision like surely we should bring them in now to make sure that we're not wasting time if it's not also aligned with their vision and just like leading the way to basically try and get them to make an intro to this person.
34:31Again, if they don't want to do that because they're not a champion and they're not influential enough in the org, then I'll just PG on my own into these people. Oh, I'm fired up. I'm so fired up that we're going to end the interview right here. We're moving to the last question, Laura, because the clock is ticking and we're running out of time. So last question for you. You've been a three-time President's Club winner, and we've talked about a lot of great habits that I know you have used to make it to the top of the leaderboard. Now I got to ask you about a bad habit. So my last question, what is one bad habit that you see a lot of reps exhibiting that you think is hurting them more than it helps and they should break it?
35:07I hate the question, any questions. And you hear this all the time. Like AEs will do a demo and then they'll say, so any questions? Or they'll show a pricing proposal. So any questions? And it's such a waste of time because inevitably, especially after demos or things like this, you ask any questions and some techie in the audience says a random question that's totally unrelated to anything of value and you just go down an annoying rabbit hole. so there are so many different ways to ask any questions that actually gets you inside the prospect's mind so the one I use a lot of is what's going through your mind as you're watching this demo what's going through your mind as you're looking at these numbers and usually people tell you exactly what is going through their mind and so then it's like okay now I know now I know how you really feel kind of thing so that's a great one to ask or the other one is on a scale of one to 10.
36:08Like on a scale of one to 10, how do you feel this feature that we just showed is going to help solve whatever problem you just told us about? Or a scale of one to 10, like where is this pricing? Are you falling off your chair with hate? Or are you like, oh, this is actually better than I thought. So there's just so many other ways to find out what your prospect is thinking. And if I had a pound or a dollar, I live in the States, but every time I said to my SEs, is like, just stop saying any questions. Just delete it from your vocabulary. So sales and SEs, it goes for both. Thank you for joining us.
36:43Everybody stick around for a 60 second recap. Coming up soon. Alrighty, Alex, it's time for your two by two recap. What do you have for your two? Honestly, where do I start? I think the big one for me is the three-legged stool. So, you know, Laura talks about this idea that in her sale, she needs a three-legged stool, like three different parts of the org need to be bought in. That is similar for my sale as well, but I haven't been thinking about it in those terms. I've been thinking about it linear. So we start here and then we get there. But in reality, in order to get a stable deal, most of us have, I mean, in smaller business sales, maybe not, but a lot of the time, most of us have multiple different kind of stakeholders that we all need to be at a green.
37:22And that's me too. So that framing was really helpful for me. And then I think the way that she talks about just facilitating rather than just going to say hey i'm an account executive mr mrs cxo do you want to meet with me instead she's brokering an introduction right off the bat to a peer of theirs in her organization which is a much more appetizing ask for an executive so that's another one i'm going to steal so nick just watch your inbox because it's about to blow up oh lucky lucky me all right my first one was the whiteboard to multi-threading so what laura will do is when she's ready to start to expand access into the org what she will do is she will use she uses miro she takes the faces of the people that she thinks she needs to get access to and builds a sample org chart on miro and then what she does is she puts that in front of her champion and gets the champion to validate one is this right it never is but that's okay that allows her to get the real org chart and then two she can start to do some discovery of who she actually needs to get access to and what different people in the org care about.
38:31That then rolls into number four, which is at times you're going to find blockers in deals. And so Laura has a very structured process for dealing with blockers. Step one, when you determine there is a blocker, the first thing you need to do is ask your champion, why are they a blocker? What's going on? What don't they like? From there, you need to figure out are they savable or not. If they are savable, the first thing you're going to do is run a little bit more discovery via your champion on what that person cares about. That will then inform your next step, which is figuring out the best non-sales resource that you're going to put in front of them.
39:09Because oftentimes blockers are adverse to talking to salespeople, but they will talk to perhaps a more technical resource. Then what you're going to do is you're going to get that more technical resource in front of the blocker to maybe not swing them to be thumbs up, but at least neutralize them to neutral. Going all the way back, if they are not savable, you need to figure out via your champion A, how much influence do they have? If they're low influence, you might not need to deal with them. If they are high influence, you need to ask your champion, should we even be continuing on this? Because if they have the power to veto a project and they're not saveable, it might not be worth continuing.
39:46But if they are not saveable and they do think it is worth continuing, the last thing she talked about is kind of crowding them out. So you need to figure out whose ear the blocker has and then figure out how can you crowd out that blocker's voice. If the CFO listens to four people and one of those four is the blocker, you've got to get the other three bang in the table of we need this product to neutralize the blocker. So that's what I had. that was a fun episode Alex oh it was good can I tell you something fun Nick yeah I booked my third meeting of the week while we were recording this 60 second recap can I tell you that and you know what after after trying the EA stuff that we learned from Laura boy I'm gonna book a whole bunch more I'll tell you that right now but in the meantime Nick how can people help us out well we talked a lot about multi-threading and selling to executives in this episode and good news for you.
40:40We actually sat down a couple months ago with the team at Gong, and we did a data study and put together what we call the ultimate multi-threading and selling to the C-suite report. This talks through the type of language that resonates best with executives, the best time in a deal to get an executive involved in your deal, how you should be thinking about multi-threading, and all sorts of other data-backed best practices that our team put together in partnership with Gong and Jen Allen Knuth. And so we've got a link to that in the show notes, give it a listen, leave it a grab. We will see you next week on 30 MPC.
41:37Plot Twist. Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't? And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now we built a toolkit with our friends in Ambition on how to actually use data to coach your team.
42:04Get it for free in the show notes. today show is brought to you by pipe drives easy to use and customizable crm with built-in meeting intelligence my favorite discovery question is the multiple choice question which sounds like typically when i'm talking with folks like you they're focused on a b or c which is it for you now a b and c have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them now pipe drives built-in meeting intelligence helps you focus on your follow-up question not on scrambling to take live notes and we built a full Discovery Toolkit with them free in the 30MPC closers hub.
42:37There's a link in the show notes.
Our new Social Selling course with Sam McKenna is live! Save $50 during launch week, through October 25. Order here →
Laura McDonald breaks down how to multithread enterprise deals, reach the C-suite, and build buying committee consensus without getting trapped with one champion. Learn how to leverage executive assistants, map the real power base, and neutralize blockers before they kill your deal.
🎙️ ACTIONABLE TAKEAWAYS:
🪑 Build the three-legged stool: Get every critical stakeholder group to “green” instead of treating enterprise deals like a linear sales process.
🤝 Sell the executive meeting: Broker peer-to-peer introductions between executives instead of asking the C-suite to meet with another salesperson.
🗺️ Map the real power base: Whiteboard the org with your champion to uncover who matters, who has influence, and who you still need to win over.
🚧 Neutralize blockers fast: Find out why they’re blocking, how much influence they have, and either win them over or build enough support around them to overpower their veto.
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