Ask Andy Whyte: What to Ask a CRO on a Cold Call
Andy Whyte shares what to ask a CRO on a cold call, how a Value Pyramid shifted an RFP, and why good salespeople make strong entrepreneurs.
February 03, 2025
9 minutes
NOTES
GUESTS
TRANSCRIPT
KEY TAKEAWAYS
- Preparation can flip a buying committee. A vendor shortlisted as the also-ran used a value pyramid to map their value to the customer’s goals, strategies, and initiatives. The customer said it completely changed their perspective.
- Questions should create urgency, not just extract information. Walk a CRO into an uncomfortable truth: how confident are you in this forecast? How many deals slipped? Skip canned scripts and arrive with a point of view.
- Good salespeople make strong entrepreneurs. They already run a franchise, taking a product they didn’t build to market in their own territory. If you have the itch, scratch it. Consulting first, then productizing, is a proven route.
Andy Whyte
CEO & Founder of MEDDICC
Andy Whyte has helped companies big and small grow and prosper as both a quota-carrying Account Executive and a Revenue Leader. His passion for helping sales teams succeed led him to become founder and CEO of MEDDICC and author the five-star-rated “MEDDICC” book. Known for his mantra “Nobody ever regrets qualifying out” and his expertise on the science and art of sales. Away from the day-to-day, Andy practices many skills as a chef, sports coach, taxi, and cleaner in his most important role to date - Dad.
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00:00:01 Andy Whyte: Producer Nick tells me we have some new questions. Let’s jump in. Okay, so it says question one. It says, “From Producer Nick, in person.” 00:00:12 Nick: It’s me. I always get the first question. It’s like I’ve deliberately messed with the running order or something. But my question to you was: what’s your favorite success story from a customer that’s implemented one of our products or solutions? 00:00:30 Andy Whyte: Favorite customer story? It depends how you define customer. If we talk about the customer being the business, the company, there are quite a few of those. I can think of one instance where one of our customers told us that after their first full quarter of implementing MEDDPICC, their average contract value went up 240% in their enterprise team, which is pretty epic. But for the benefit of giving an interesting answer, one of my favorite stories was recently, when a salesperson reached out and said they’d been invited to participate in an RFP. Off the back of their response, three companies were shortlisted, and they were one of the three. They went to the first meeting and used a value pyramid, which is one of the structures, or frameworks, you can use as part of the playbook. As part of our playbook, we have a program on the value pyramid. And because they’d been through that program, they used the value pyramid to position their value alongside the customer’s goals, strategies and initiatives that they’d learned from the RFP. 00:01:35 Andy Whyte: Although they haven’t won this deal yet, it’s still in play. I believe it might have moved on a bit since I last heard, which was only a few weeks ago. But what they told me was that the customer’s feedback was that they were actually the also-ran vendor in the mix. The customer said they had to take three through, and they had two favorites, and they’d brought this vendor through because they’re a well-known company in the industry. But they certainly weren’t the preferred vendor for the buying committee. And the customer gave the feedback that, because of their approach, particularly the value pyramid in that first meeting following the RFP, they had completely changed their perspective and had started to really strongly consider this vendor. I mean, if the customer is telling you that, you’ve probably got a pretty good potential champion. So that’s a great story. It just goes to show the power of preparation, the power of the tools and the playbook, and all that kind of good stuff. Okay, so question number two says “mystery external guest.” Let’s play that. 00:02:31 Madison: Hey Andy, it’s good to see you. It’s your friend Madison. I have a question. How did you make the decision to start your own business and leave behind a really successful career in enterprise software? The reason I ask is that I often feel the urge to scratch the entrepreneurial itch myself. While I feel like, quite frankly, the great opportunities I have keep me from doing it. 00:02:54 Andy Whyte: What a great question. Thank you, Madison. I think there are a couple of parts to this question. The first is that I actually didn’t intend to start a business this way. The reason I ended up on this, you could call it, career line was that I wrote the book, MEDDICC, and I actually did that to improve my chances of getting a better job. My goal was to be a CRO. I thought, if I can improve my brand and get myself out there a little bit more, my chances of getting the job I wanted would improve. So that’s the first part. But, in the nicest possible way, it’s ended up with this: all these great people I get to work with every day, and being able, as a team, to create our own destiny, if you like, which is really, really cool. So I would encourage anyone listening to this who has that itch to definitely go and scratch it. And what I’ve learned, to give the second half of that question more value, is that if you’re a good salesperson, you’re very often a brilliant entrepreneur, because what you’re effectively doing is running a franchise. 00:04:01 Andy Whyte: Me as the CEO of this company: we’re a software company, and of course I don’t have any technical expertise. I’m not a coder, I’m not a developer. And if you look at what a great salesperson does, they take a product that, a lot of the time, they’ve had no input into, and they take it to market in their territory. So salespeople have a lot of skills, and they probably don’t get enough credit for being entrepreneurial. My advice would be, if anyone has got that itch, definitely go and scratch it. If you can find something you’re deeply passionate about, where you have a voice and people value your input, that’s obviously going to help a lot. And I would recommend the consulting-to-productizing route. It was a really good route to go down. So yeah, that’s a cool question. Thank you for that one, Madison. Good to see you, as always. This next one is from Naomi Chu, and it says, “Hello to Nick behind the camera.” 00:04:56 Andy Whyte: I’m glad you put “behind the camera” on there, because, you know, he could be anywhere in this room, but there you are, behind the camera. Thank you, Nick. You just never know with me. You never know. So the question from Naomi was: if you could only ask three questions on a cold call to a CRO, what would they be? Really? Oh, wow. This is going to show how I need to do some more cold calling. So some of these are off the top of my head. I guess I’d be thinking about how I can implicate pain with my questions. I always think about the questions you ask the customer. In our industry, we think about discovery questions, or questions in general, as a means to extract information, which is obviously important. We want to understand what’s going on in the customer’s business. But for me, an equally important, or bigger, opportunity in asking a question is not just to extract information, but to walk that customer into that moment of uncomfortable truth, where they have to live the pain they might be experiencing in their business. 00:05:54 Andy Whyte: That increases the urgency in their heart. So if it’s a CRO, and I’m assuming the question is about me selling our services, I’d ask questions around things I think are pain points for our customers, which is going to be around forecast accuracy. If it’s timely, I’d probably look to understand what the company’s financial year is prior to my call. If it was leading up to a quarter end, I’d ask how confident they feel about their forecast. If it’s just after a quarter end, obviously I’d ask them how accurate their forecast was, how many deals slipped, and whether they think those deals will still close. I’d be trying to get to whether it’s just a case of the process not being managed well, or whether they just don’t have any idea what’s going on. So those are the kinds of questions around confidence. I’d also ask a question that I think is quite strong at the moment, as we’re in a time of efficient growth, which would be around the efficiency of salespeople. I’d be thinking about productivity, about making sure salespeople are spending their time on the right opportunities. 00:07:12 Andy Whyte: I’d be talking about ramp times. So those are the kinds of questions I’d be asking. But I’m not a massive fan, and I think people know this, of canned questions, like, “Okay, I’ve got through, I’m going to do my pattern interrupt, and now I’m going to ask question number one.” I like to go into a conversation with a point of view, based on research I’ve done, experience I have, and working with similar peers. So it’s going to be very particular to the person I’m trying to talk to. Doesn’t time fly when you’re having fun? This is the last question. 00:07:38 Caleb: Hey Andy, it’s Caleb here. A quick question for you, and one I’ve always been curious about. In your role as CEO, you’re pulled in so many different directions. How do you prioritize and manage your time as efficiently and effectively as possible? 00:08:00 Andy Whyte: I’ll tell you, I find that one a struggle. I’ll be honest with you. The best way I’ve found of doing this is that in the morning, I write down my top three things. And sometimes I forget to do this. I’m not going to be one of those people, you know what they’re like: “I get up at 5 a.m., meditate and do yoga,” or whatever. But if I can remember, which is most mornings, I’ll be honest, I write down the three most important things I want to get done that day. I tie it into journaling as well. So I take the time to think about things from a broader perspective: what would make today good, what I’m grateful for, and all that kind of good stuff. But yeah, I tend to pick out those three things. And what you find is that it helps you plan the day, because you can say, “Okay, what’s the most important thing? What should I do first?” And you can reflect on the day before and anything you didn’t get done. So yeah, that’s how I do it. 00:08:55 Andy Whyte: No, nothing particularly groundbreaking there, I don’t think. So that is episode number three. Thank you so much again for your questions. And please, please, please, if you have any questions, get in touch. I really enjoy this. Let me know any questions you might have. The best place to put them, I learned from the last episode, is down there in the comments. Please let me know any questions you want me to answer in the comments below. If you’re shy and don’t want to write them down there, you can get me on LinkedIn as well. I look forward to hearing from you. Thank you.
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This is a lightly edited transcript. Some sections have been condensed for readability.
ABOUT THIS EPISODE
SHOW
ASK ANDY WHYTE
EPISODE
S1 | EP 3
DURATIONS
9 mins
PUBLISHED
2025
Video
Andy Whyte
Ask AW
CHAPTERS
00:12
The Value Pyramid That Turned an Also-Ran Into a Contender.
02:31
How Andy Ended Up Starting a Business Without Planning To.
04:56
Three Questions for a CRO on a Cold Call.
07:38
How Andy Manages Time as CEO.
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