Why You Can’t Sell to C-Suite Executives

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This is a podcast episode titled, Why You Can’t Sell to C-Suite Executives. The summary for this episode is: <p>Have you ever had a meeting with a CXO and completely bombed? You asked the right questions, or so you thought... New data reveals the sweet spot for how many questions you should ask a c-suite exec and how to use them to uncover money-making deals. Join Ian Koniak, Strategic Account Director at Salesforce to unpack the sobering truth when selling to the c-suite. </p>
Data: The correlation between the number of questions asked and the close rate when selling to executives
02:28 MIN
How to make the most of your conversations with C-Suite Executives, without asking too many questions
02:44 MIN
Is there an order to asking discovery questions?
02:36 MIN

Devin Reed: What's going on everybody? Welcome back to another episode of Gong Labs Live. Hope you're having a fantastic Friday. If on the West Coast, hope your day is just getting started on a good note. If you're on the East Coast, hope you're hanging out at lunch. I don't know international timelines, or time zones, too well, so whatever time it is if you're elsewhere, welcome to the show. My name is Devin Reed. I'm the head of content strategy here at Gong, and I'm really excited for today's episode. But before we get into it, always like to share a quick icebreaker question. A little something to get the comments section going, to get your brain going. I've got a real simple one for you. It should be a knee jerk reaction. You should know the answer here. Which is, what's your favorite holiday? What is your go- to holiday? What's the one that gets you the most excited? I'll share mine. I'll tell you my least favorite is Halloween, never been a big dress up guy, never been a fan. But I really love Diwali. My wife's Indian. My family, now, is Indian, and Diwali is fun. It's around that Christmas time. It's a fantastic event. Go and drop your favorite holiday in there, and we'll get going here. Okay. If you're new to Gong Labs, welcome. Thanks for hanging out with us, really excited to have you here. And if you're returning, we love you too. We're very grateful that you're here week over week, hanging out with us on a Friday morning. Here's what the show's all about. We bring sales data and real talk on sales together. And every week I get to interview a sales expert, and we share some entertainment, hopefully. Laughs are up to you. But we also make sure that we share some actionable tactics that you can take with you to make you more effective in your role. Maybe you're in a leadership position looking for a way to make your team more effective. Maybe you're an individual contributor looking for one way to get 1% better today. Or maybe you just want to shatter records, make more money, whatever it is that motivates you, we're going to make sure that we deliver that every week. All right. Now, speaking of delivering, giving, holidays, Christmas, we got a gift for you. We have a Gong Labs Live Dad Hat. Now, it's just called a Dad Hat. I say this every week. There's nothing really about it specifically for dads. You can be a mom, you can be a pet mom or day, or you can have no kids, at all. But if you want to get your hands on the hat, all you have to do is tag your best friend in sales. Tag them in the comments section, let them know the show exists. And it can be someone you're rivaled with. It can be your manager. It can be your best friend on your sales team. Whoever it is, go and give them a tag, and someone from our team will reach out and make sure we send it over to you. All right. Now, we're also going to drop a quick link into the comments section for all of the on- demand episodes of Gong Labs Live. This is episode eight, so there's seven more waiting for you. If you want to go ahead and check it out, we'll go ahead and drop the link in there. All right. Let's get into the show today. We are with a fantastic individual, Ian Koniak. Ian Koniak, welcome to the show my man.

Ian Koniak: What is up? Great to see you again, Devin.

Devin Reed: Always a pleasure. Ian, you're a special breed, because you're both a top shelf sales pro. You got, I think, 18 years consistently being a top performer, at least, 18 years in the game.

Ian Koniak: Yep.

Devin Reed: I'm looking at my notes here. I had to write it down you've got so many accolades here; 100 million in sales at Fortune 500 companies. And the other thing that really sets you apart, and that we got to know each other on, Reveal. You're on Reveal: The Revenue Intelligence Podcast, is that you're really vulnerable and transparent about your journey. And you're really big on helping others, and helping others accel, which is exactly why I wanted to hang out with you again. It's uplifting and I'm really grateful that you're on the show.

Ian Koniak: I'm glad to be here, man. And appreciate everything you're doing, as well, to support the sales community.

Devin Reed: Thanks, man. Aside from our mutual love for sales, that's obvious, we have another shared passion. We're both coaches. We love coaching and helping others. I coach my team. You've got teams that you coach, as well. And so, I'm curious, in your years of coaching, what have been some of the big sales takeaways, maybe, those big learning moments?

Ian Koniak: I think what I come across constantly. I started coaching before I ever got to Salesforce. I ran a team of 80 employees. I had 10 sales managers and I had 70 AEs, and I did all the training and coaching. And before that, my favorite job was a frontline sales manager, so we had our team. My proudest accomplishment is getting everyone on my team over plan, 100%, on a team of eight. I did a lot of coaching.

Devin Reed: Might just be me, I think Ian might have froze. I'm going to wait a second here. Maybe it's I'm froze. We've had this happen, where I think the other person is froze. Really, I'm the one that's frozen, so we'll wait a sec, and there we go. I'm getting a note. Ian's unfroze, so we'll refresh. We'll get him back on here. Well, let's do this, let's jump into the poll for today. We'll just skip ahead a little bit here, and we've got a poll for folks. Because today what we're going to talk about with Ian, when we get him back on the line, is selling to the C- suite. Ian is phenomenal at executive conversations, and we'll hopefully get him back on here to share. But we have some Gong Labs data that I wanted to share with you, as well, to help you have better executive conversations. We ran the numbers, and there is an ideal number, a little window, of questions when it comes to discovery questions with executives. Why don't you go ahead and jump into the comments, and put in what you think is correct. We've got, A, three to four questions is how many you should ask, B, five to seven, C, eight to 10, or D, 11 to 13. So ahead and punch it in there, A, B, C, or D. I'll know which one you mean. We'll just hang out for a second. I jumped back to the comments, I see Ian is froze, so thanks everyone for jumping in and letting me know it's not just me. All right. We've got a bunch of As, some Bs. Thanks, Diana, Amanda, Jeff, Travis. I'm just giving you shout outs. I'm not telling you if that's the right answer, quite yet. I'll wait another moment or two, let folks jump in here. Lot of As and Bs, love it. Okay, we finally got a C in there. No one's D. I haven't seen any Ds, yet. All right. Let's get into the answer. I'll go ahead and flip the slide here. There you go. And there you go, you have your answer. The answer is three, four, so the answer is A. Answer is A. Here's what we did. Here's what we did. We looked at... My man, Ian, you're back. Can you hear me?

Ian Koniak: Yeah, I can. Sorry about that, I just changed rooms, because I work in the back studio. And, of course, the one time I'm live this has to happen. Can you hear me okay? I'm in my son's playroom now.

Devin Reed: I can hear you great. If the son's back there hanging out, he's fine. We can't hear him, at all.

Ian Koniak: We're good. He's still in the house.

Devin Reed: All good. You did warn me before the show. You're like, " This is probably going to happen," and, hey, when you do a live show, you're not looking for perfection. It's like a demo. You get to the big moment, you're like, " This is the screen that's going to change your day," and you get the 404 error, right?

Ian Koniak: Well, this is real time, right?

Devin Reed: Yeah.

Ian Koniak: You've got paintings and playroom in the back. But as long as I'm live, I'm good.

Devin Reed: All good. You're set. Hey, we just ran the poll and asked people how many questions they should be asking discovery call questions for executives. And so, we just got to the reveal here, which is the data. We ran the numbers, and we looked at the correlation between the number of questions asked and the close rate when selling to executives. What the data showed here was a very small amount is ideal, so around, what, four, five, six, in that ballpark is the ideal number. And you start to see a solid taper off, or a decline in close rates the more questions that folks ask. I've got a bunch of thoughts on it. I've discussed this before, but, Ian, I'm curious what your knee jerk reaction is when you saw this slide for the first time?

Ian Koniak: It makes sense. Executives, when you're selling to executives, you do not want to interrogate them. You want to spend time learning about what's important. I always have my questions laid out in advance before talking to executives. The key thing you're looking for, and for me it's usually around eight is the magic numbers, so that aligns really well. You want to learn about their top three strategic initiatives for the year. You want to learn about why those are important. You want to learn about the challenges today that are potentially impacting the ability to achieve those initiatives and the cost of those challenges. And then you want them to think about value. You want to think about success. You want them to imagine and fast forward a year from now, and what success could possibly look like for them, if they were to achieve that. And what that would mean for them, for their companies, and their employees. That's about it. You really just want to understand what's important, what they're trying to do, and get them imagining the possibility. And then, finally, you want to get them to identify their right hand person. Every exec, every CEO, every CIO, every executive I ever sold to, I call it yo- yo selling. And it's I start at the top, I learn what's important, and then I find out who I can work with on their team to get the deep process information, the system information, the product type discovery I'm going to need, all of the people, the department interviews. I don't want to do that at the C- suite. I want to do that at a level below them, so that I can go back and then bring all that back up. That's why I call it yo- yo selling to the executive to report my finding.

Devin Reed: crosstalk.

Ian Koniak: It really is. They're going to get deal fatigue very quickly, if they just get grilled. And frankly, they're not going to know the answers, and they're going to be somewhat embarrassed, or they're going to say that's for someone else, and they'll start pushing you to someone else, if you've been down to that level. You've got to keep it high level. You've got to keep it strategy. And you've got to have the right questions for them.

Devin Reed: I like that. What's the phrase? Basically, you get pushed down to the person you sound like. Delegated, you get delegated to the person that you sound like. That's the phrase I was looking for. But you probably get one of those, right? One or two is okay, because someone's like, " That's not me, that's my right hand person," or someone else. But if you go down that road too much, I think their brain shifts to like, " This whole thing is not for me. This whole conversation isn't for me. It's for somebody else," and that's something we want to avoid as sellers. And I like that you called it out. It's discovery fatigue. That's what we're looking at here is constantly peppering people with questions, making calls feel more like an interrogation than a conversation, if you're just constantly asking questions. It sounds like, Ian, with your yo- yo selling, which I love that name. You're saving a lot of those questions for the champion, or their right hand person. Is that how you prepare for those meetings as well? You go into it knowing some information? I guess the question, which I imagine a lot of people are wondering, how do you get information from a C- level person and make the most of those conversations, if you're not supposed to ask too many questions?

Ian Koniak: Yeah. A couple things, number one, is you have to come with a point of view. You have to add value first. Executives aren't just going to go and share their initiatives, and tell you how they're measured, or what specific challenges they have, until they know it's worth their time. So the way to show executives that you're worth their time is through extensive and quality research. What I like to do is I like to look at that executive. I'll listen to podcasts they've been on. I'll read their interviews in Entrepreneur, or Forbes, or wherever they've been published. And I will come and pull some quotes on what they said, and I'll start asking questions about what they meant, or how their doing this thing. Because in those interviews, they tend to speak at a high level, so that's number one is come prepared with the executive questions that are relevant. And then they'll start opening up. Number two is come prepared with a point of view on how your product or service can tie back to whatever they're talking about. So it's not just a matter of, " Hey, I've done my research on you, tell me more." It's, " I've done my research on you, and I think I can help. And here's an overview of how I think I can help, but I'd love to get your thoughts and see if we're on the right track. Is this really where you're focused, or is there something else that we should be thinking about that's top of mind? I want to give you the opportunity to share what you're thinking." Just by doing that, and having really giving value first, gives you the permission to then ask those questions. That's number one. The second thing is I break my discovery questions into four buckets. And this is what I coach people on, specifically. There's the executive questions, which is the high level goals, priorities, challenges, and vision of an exec. Then there's the process discovery questions, which is how do you do things today? What systems are involved? How many steps? How many people? That's really where you're trying to show more efficiency or an automation from what your software can do. The third question is the product questions. Those are what they're using today. What the integration inaudible. It's helping you qualify and quantify what you're going to propose to them. And then the fourth bucket, which really is for finance, is the value discovery questions. And that's like, literally, what you're paying employees? How long it's taking? What your financial goals are? Your profitability, so you can back an ROI that ultimately is going to go into finance. The key is to ask the right questions, to the right audience, to the right persona in that sales cycle. Really, when I'm with executives, I will, at the end of the meeting, I'll pitch, " Hey, here's what we need to know to help you get what you want. We need to know the technical, who's that person? We need finance for value. And we need process. Is there one person that can help me, or we do a few interviews?" Typically, they'll have one person who's their go- to, SVP, or VP that's going to then be handed off, and then will walk you through getting the rest of the information. But you want to keep that exec in the loop, so that's typically how I do it.

Devin Reed: That's interesting, Ian. You say up front in the call, almost, here are the questions I'm going to ask, but you put it in the way of here's what we need to know to make this conversation meaningful. So you're prefacing, there's some discovery questions that are coming, but you've given them why, right? It's not just like I'm running through my discovery script. I'm not just going top, bottom on these 10 questions. There's a real specific reason I'm going to ask these questions. Last question I have for you is, do you have a certain order that you put those questions in, because you had mentioned future state. And then the last one you mentioned was current state. I'm wondering if you do that specifically, or if that was just your talk track?

Ian Koniak: Yeah. The first thing I'll tell you is, I never tell them all the questions I need answered up front. What I position is here's our process. We need to look at your systems, your step- by- step process. We need to, ultimately, look at some costs and show you an ROI. Who's the best person to work with, and can you make an intro? I usually get them to hand off, send an email, if they don't want to, I'll just draft it for them. Literally, we'll kick off a discovery process. It's really helping them understand what's entailed to actually get whatever it is that you talk about that they're interested in. That's the key thing is, is a clear and concise delivery of what your process is to help them, and then getting their confirmation to come back and actually do a readout with them, once you've done your discovery. Because they don't want to be in the weeds for that discovery. As far as the order of questions, what I typically like to start with is what's top of mind for you? What are your top priorities? And then I go to challenging, specifically, because everyone knows what they want to do, or what they're working on, but when you ask for challenges first, the context is in the challenges that align to those specific priorities. Because you don't want them listing off a bunch of random challenges, or pain points that are irrelevant to the priorities. What I ask, specifically, is what are the top challenges or pain points today that might get in the way of achieving those initiatives? Then we can think about the current situation. Then it naturally flows into, " Okay, what's the cost of that challenge? What's that costing you today? What's the impact of those challenges?"

Devin Reed: Impact questions, right?

Ian Koniak: You really want to align. The other thing is, you don't want to do that with every initiative. You only want to do that with the initiatives that you can actually support. If they have a big initiative about consolidating their call centers from eight to one into a global area, and I don't have anything to do with call centers, then I want to move and find the one that I can actually align to or support. That, I think, is the natural flow of it. And then the final flow is to take the value questions at the end. After you understand the priorities and the challenges, then you go to the value and say, " Okay, I understand what's challenging, let's fast forward for a year," and this is my favorite question with all executives. I ask it every time. Fast forward a year, let's say you've accomplished everything that you've wanted to, that you set your heart out to today. What would you have accomplished a year from now, if you had the best year of your career?

Devin Reed: The aspirational question, I like that.

Ian Koniak: Yeah. Then you're getting him thinking about the possibility. And then I ask, " Well, what would that mean to your employees, if you're able to do that? What would it mean to your company? What would it mean to you, personally?"

Devin Reed: I love that. I like that, because I'm thinking about my goals. I'm like, " Man, in a year, if I accomplish everything, I'm going to be on top of my game. I'm going to be very happy." And so, now, anything that you're like, " Well, this is what we have to do to get there." I'm fired up and ready to go. It's almost like an emotional crosstalk.

Ian Koniak: You are literally getting them to imagine a better future. It's 100% emotional. It's 100% psychological. And it's 100% effective, because no one's asking them that. You sound like everybody else, if you show up and talk about features, or products, or what you can do. Talk about them. Be interested in them. Get them thinking bigger for themselves. You are trying to activate something bigger in them. That's the key, and that's what really connects you with that deeper human level. And makes you, as a sales rep, really want to care about their own success when they've opened up and told you what they want. Man, I am vested in helping them get it, and it really feels good.

Devin Reed: I can tell. I can tell. Well, that's fantastic advice. I really like it. I'm going to steal that last question, for sure. And to our listeners, we're on a short time schedule today. This is a short show. So if you want a little bit more on selling to the C- suite, we have an on- demand webinar you can check out, where we go even more in- depth here. You'll learn conversations that drive urgency. Hear some real life examples. And so, we're going to drop that into the show notes, or the comments rather, here. Ian, you brought it. Now, it's time for the rapid fire round, all right? Are you ready? You've got five questions. Excuse me, well, there's five questions. You have five seconds to answer each question. I don't have a shot clock, it's an honor code. Are you ready?

Ian Koniak: Let's go, baby.

Devin Reed: All right. Who is a sales expert that we have to follow on LinkedIn?

Ian Koniak: Joe Caravana.

Devin Reed: I've not heard of Joe Caravana. We'll have to check him out.

Ian Koniak: He's one of the most consistent top performers. I don't think he puts content out on LinkedIn, but he is one of the best guys at Salesforce, the best. For content, Marcus Chan. I love his content.

Devin Reed: Marcus is cool, yeah. I love Marcus.

Ian Koniak: Yeah.

Devin Reed: All right. What is your favorite podcast, sales or otherwise?

Ian Koniak: Ed Mylett Show. Yeah, it's the Ed Mylett Show. It's called, Max Out. He's just motivational, gets the most successful people from in and outside of sales, all walks of life, just those common success habits. By far, my favorite, Max Out.

Devin Reed: Got it. I will check that out. You're currently on pat leave, so thanks for joining by the way while you're on pat leave. What's the biggest learning you've had from being a parent, so far?

Ian Koniak: The biggest learning is you have to lead by example. For me, I think I shared about this, but I've been, now, sober for 17 months. I've had some addiction in my family. And, for me, it's be the person, be the father, be the example for other people that you didn't have. I just want to model the right behavior, the right attitude, and how I show up, and just be loving, be kind, be good. Kids light up. You're a dad, you know this. It's the biggest joy to see the smile on your kid's face when you get in. And that, for me, is just be a good person, and model the behavior that you want to see from others to your children.

Devin Reed: 100%. I am a new dad. I'm nine months in, so quite a rookie, but that's something I learned very quickly, as well. The importance of patience has never been higher, and leading by example is huge. Okay, last one, since we're talking about executive conversations today. What's one thing sellers can do to increase their business acumen?

Ian Koniak: Well, I have a... I'll plug myself shamelessly.

Devin Reed: Do it.

Ian Koniak: On my YouTube, I've been interviewed and I did a 60 minute presentation for Sales Hacker called, Impactful Executive Conversations. It was all about how to get into the C- suite, and how to communicate with the C- suite. Number one, watch that. I'd say number two, you need to know that you are worthy, and I mean that. The reason people don't speak to executives is because they don't think they have any value to add. They're intimidating, intimidated. What do I have to give? This person's so successful, they're so high up. At the end of the day, we all put our pants on the same way. The higher I go, and the more executives I meet with, the more I realize they are the nicest people. They are direct. They are concise. They are transparent. And they are the best the work with, in my opinion, because they'll tell you what they want and need, and save you a lot of time. Power compresses deal cycles, so it starts with knowing that you're seeing yourself as an equal, and just going out and doing it. Get it out of your head, and start having these conversations, and start reaching out to the executives, and you'll see they're just like you and me and your deals are going to move a lot faster. It's the head game of just knowing you're worthy to actually have the conversation in the first place that's most important.

Devin Reed: Absolutely. Ian, thank you very much, man. Fantastic advice. Really appreciate your time, especially, while on pat leave. I'm going to tell folks to follow you on LinkedIn. Is that the best? It sounds like, maybe, LinkedIn, and you've got a YouTube channel, if you want to give it a quick plug so folks can find you.

Ian Koniak: Yeah. Hit me up on LinkedIn. Hit the connect button. I'll send you a link to my newsletter. I send out sales videos every week. I'll send you a link to my YouTube. You can subscribe. It's just youtube.com/ iankoniak. LinkedIn it's Ian Koniak. I put out a lot of content very week, would love it if you follow me, and I'll help you wherever I can. If anything resonated, shoot me a DM and I'll see where I can support you if you have questions.

Devin Reed: Love it. I follow you, Ian. And for everyone listening, genuinely enjoy Ian's content. That's why I want him on the show. Thanks, Ian. For our viewers, we have two offers for you. You might've missed the first one at the beginning of the show, but I want to give it a final plug, Gong Labs Hats. We're doing a giveaway. We actually sold out of them, the first few, so I went to the CFO asked for a few more bucks. I said, " Hey, we've got this show going on, some great people are showing up, I want to make sure we can give them some swag." All you have to do to get the hat, tag a friend in sales in the comments section, and someone from my team will reach out and make sure you get it. Offer number two is on Wednesday, Gong is hosting Celebrate Together, The Revenue Intelligence Summit. It's an online virtual half day event. I'm going to be there talking about how to close six figure deals using team selling. There's going to be some great networking, panels, more giveaways. We'll drop a link there. You can go ahead and register for free. Thanks for hanging out with us on Gong Labs Live. Hope you have a great rest of your day, and we'll see you next week at Friday. See you next Friday at 9: 00 AM Pacific.


Have you ever had a meeting with a CXO and completely bombed? You asked the right questions, or so you thought... New data reveals the sweet spot for how many questions you should ask a c-suite exec and how to use them to uncover money-making deals. Join Ian Koniak, Strategic Account Director at Salesforce to unpack the sobering truth when selling to the c-suite.

Today's Guests

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Ian Koniak

|Strategic Account Director, Salesforce