How to be Discovery and Demo Ready with Bruce Scheer and Ray Schloss

Key Topics

  • Prioritizing discovery before any demo
  • Tying features to quantified value
  • Creating emotional impact and memorability
  • Tailoring and personalizing presentations
  • Moving from novice to expert selling behaviors

Episode Summary

In this episode of the ValuePros Show, Bruce Scheer talks with enterprise sales veteran Ray Schloss, who spent seventeen years at Microsoft and led enablement for over a thousand sellers, about how to be discovery and demo ready. Schloss argues that a demonstration only succeeds when it delivers both value and memorability, and that the fastest way to lose a deal is to show features without ever tying them to the customer’s real needs.

The pair contrast novice and expert behavior, from the classic "so what" demo crime of listing features to the discipline of quantifying outcomes and painting a picture the buyer can see themselves in. Schloss shares vivid stories, including a demo that failed because it used generic bicycle-shop data for a medical device company, and stresses that discovery, effective listening, dry runs, and genuine passion are what turn a forgettable pitch into one that connects with both the heart and the mind.

Key Takeaways

  • A demo only works when it delivers both value and memorability; missing either one means you will not get the result you want.
  • Never show a feature without tying it to a quantified benefit that maps back to what you learned in discovery.
  • Prioritize discovery first; the rule of "no discovery, no demo" protects you from wasting time on deals you cannot win.
  • Tailor and personalize every presentation to the customer’s industry and needs rather than defaulting to generic demo data.
  • People buy on emotion, so build genuine connection and tell stories that make your message land and stick.
  • Become an effective listener who asks great questions, then rehearse with dry runs and an objective observer before presenting.

Quote-Worthy Moments

“So what can you do as a presenter to create value and generate emotion?” – Ray Schloss

“The novice is going to just show the feature with no benefits. The expert is going to show the feature, describe the benefit, but also tie it to value.” – Ray Schloss

“All things being equal, people will buy from people they like.” – Ray Schloss

“Find something that you can tell a great story around that’s got passion, that’s got emotion, that’s gonna be fun.” – Ray Schloss

“An expert prepares, and they tailor, and they make it relevant in that buyer’s eyes.” – Bruce Scheer

“You tied that feature into value, circling back to the problem that you stated you wanted to resolve.” – Bruce Scheer

Full Transcript

View full transcript

Bruce Scheer: Welcome to the ValuePros Show where value pros get value ready. Hi. This is Bruce Scheer, your host. And in this episode, we are talking with Ray Schloss about how to be discovery and demo ready. Ray is an enterprise sales veteran with over 25 years of experience, including 17 years at Microsoft where he served as the global technical sales director for Microsoft Business Applications. Ray started an amazing community there where he served as head of enablement over a 1000 sellers at Microsoft. So talk about at scale. Ray is known for his impactful presentations that touch both the heart and mind of his audience.

Bruce Scheer: He brings a wealth of knowledge on how to conduct effective discovery and deliver memorable demos. Whether you're new to sales or a seasoned pro, you're in for some valuable insights on how to stand out in your next customer engagement. Let's dive in. Alright. Well, Ray, welcome to the show. I'm so excited for our conversation today. How to be discovery and demo ready. So just for a little bit of context for everybody, you know, we put together a framework, a value readiness framework, and it follows 4 key phases.

Bruce Scheer: And, miraculously, it ties together with the buying journey. Now there's 10 value ready dimensions, 3 under build trust, 2 under understand needs, and then 2 under deliver insights, and 3 under drive execution. And Ray is a master, an expert, I should say, at being discovery ready and demonstration ready. He spent so much of his career doing that across the Microsoft and other very large organizations. So it's really fun to have Ray with us to talk about this. Ray, welcome to the show. So grateful that you're doing this with us.

Ray Schloss: Bruce, happy to be here. Thank you.

Bruce Scheer: Awesome. Well, Ray, why don't we talk about why is it so important to be discovery and demonstration ready? What's the big win behind that. And I know you got so much experience, whatever you have to say, man, bring a poll.

Ray Schloss: Yeah. Well, I mean, so much would have to do with the very mission statement of value pros, Bruce, because without demonstrating 2 key things, I think one is, is value, but 2 is memorability. The client is not going to choose you for whatever you're doing and whether that's in multimillion dollar software discovery process, or if it's just speaking to a local chapter of your first responders or something, it's really having the impact for the people in the audience to be able to say, getting value out of this. And it's memorable. If you don't check both of those boxes, you're not going to achieve your expected and desired results.

Bruce Scheer: Absolutely. Yeah. So you gotta hit those bars for sure, Ray. I would guess the prize in doing that well would be better buying experience. You'll stand apart from other sellers big time if it's a competitive situation, and you should increase your win rate if you do these steps really, really well.

Ray Schloss: Yeah, absolutely. And it was something that I recently just kind of semi retired, and at 17 years at Microsoft. And as you mentioned, I had a number of years at other large software organizations and companies. And we would be in situations where there may be even a scripted demo that would be 3 days long and the client would be evaluating a combination of financials and supply chain. So, we would have to go through screen by screen and prove to them, oh, here's how we do three way matching for invoice processing or this is general ledger posting, right, or this is how you're gonna depreciate a fixed asset. Thankfully, I was the technology sales consultant. So I got to talk about more exciting things like web APIs. Like, there's someone as if he was supposed to be an accounting major that dropped accounting on the 3rd day of accounting 101.

Ray Schloss: So there were people that we had that were usually CPA level who who back to CFO is about going through that kind of a presentation where it's dry. Right. And you're like, here's how you take sales order and the invoice. And you can't do something to make the audience feel like they have an emotional action. When Oracle comes in the next week and the week after that, and you're all showing three way invoice matching. No one's going to remember anything you have to say. Right? So what can you do as a presenter to create value and generate emotion? Remember it. And it goes very much to what my Angelo shared about.

Ray Schloss: People will remember what you tell them, but they will remember how.

Bruce Scheer: Absolutely. I love your point about having that emotional connection through the process. So critical. I was just speaking with the former president of Gong. Io and Tableau in our backyard. She was a chief revenue officer there, and we're both agreeing in this world of data and digitization. Data's king and really important, but people still do buy on emotion. And especially as you're doing the demonstrations, Ray, just making that an emotive experience. How smart is that? I don't know if people think that way a lot.

Ray Schloss: Yeah. Well, part of that too, Bruce, is you've got to be willing to be almost foolish, right? You have to do something above and beyond just giving information. And you can even think of how many presentations have we seen. Obviously you and I are both involved in a national professional speakers organization that you can watch someone give a good presentation that may have good information and data and a week later or 48 hours later, you can't really remember what they said. One of the best presentations I've seen in quite a while was from the CEO of a company called Youdly and they do AI generated sales training. So it's actually an avatar and you have this conversation with it. And then at the end of your pitch, it gives you a whole rundown of what points you hit. Where were you weak? What do you need to improve on? Very, very cool.

Ray Schloss: And I remember walking out of that presentation and I couldn't give you all the data points of what she said, but her passionate description and demonstration of the software and painting the picture of where this can take a sales organization. I was absolutely floored and it created that emotional kind of impact that great presentations are capable of delivering.

Bruce Scheer: So cool. Well, let me, have you talk a little bit, Ray. And again, you are serving thousands of sellers when a sales enablement type of capacity. So I know you've seen things. Could you talk about, Ray, just the things that you saw at a novice level juxtaposed against behaviors you saw at an

Ray Schloss: expert level in terms of how

Bruce Scheer: to be discovery and demo ready? Level in terms of how to be discovery and demo ready. What have you seen and what should we be looking out for versus what looks really good from what you've seen?

Ray Schloss: Yeah. Well, Bruce, one of the things that really helped clarify points regarding not novice versus expert, it demoed to when they call them demo crimes. And what are the main ones that's just, so what, so a novice typical behavior in a presentation or a demo is giving information that doesn't tie to value. So, you could think, oh, wow, let's just go back to the three way invoice matching a very bland, boring voice object. Right. And you're just going through, oh, look, this is the line item, so we can change the quantity here and we can do this and we can do that. And you're just going through information and it's just droning on and it was just going on. And we also changed the song and then you're losing the audience.

Ray Schloss: So what that you can do that you're not tying. How is this going to change it? If you have done discovery correctly, you understand where the win statements are, what their real needs are. Not just, we want to have better systems, but well, why do we want to have better systems or what? So you go back to, oh, we can change the quantity on this line item in a purchase order By doing so, we're going to decrease the amount of time it takes you to complete each and every invoice by 28%. That's what we found with our customers. We've extrapolated that over one fiscal quarter of your current workload, and it is going to save you 28 human hours per week. And then that extrapolates with average salary. Boom. You're going to pay for the total cost of this software purchase and implementation within the next 18 fiscal months.

Ray Schloss: If just by implementing this one feature. Now that is a completely different story than, oh, we can change the quantity on this line item in an invoice. Right? So the novice is going to, is just going to show the feature with no benefits. The expert is going to get show the feature with describing the benefit, but also tying it to value. And if you map it back to Bruce, when we were going through discovery, one of the things that you shared is that we've got to reduce the number of hours it takes to really effectively process a fiscal month's worth of invoices. This is how we're going to get it done for you. Do you see how that worked for you, Bruce? Like, I mean, that is just, that's a completely different way to go about it. So these are the kinds of things that we would try to move the needle of a sales organization being from a more novice out of the box standard way of just giving a presentation to actually developing it into something where there's an expert level of value and emotional impact.

Bruce Scheer: Absolutely. No. That makes sense. And as you were speaking, my hunch is that buyers' confidence in you as a seller and the solution you're showcasing goes up because you're doing that full circle effect. I listened to you. I tied that feature into value, circling back to the problem that you stated that you wanted to resolve. That whole circle, just building confidence back to your point of creating that emotional experience that, hey. Ray's straight up. That person's a great salesperson and just nailing it. I feel good about what they have to say. My confidence goes up.

Ray Schloss: When, you mentioned about people still buy from, you know, we're buying from people and Zig Ziglar, who I think we both love. He was an amazing guy, a real groundbreaker in human performance and sales optimization. Although he wasn't really dealing with international complex situations like enterprise businesses competing for global deployments. He was a lot of his experience came through selling pots and pans door to door, but it's still the same. But one of his axioms was all things being equal. People will buy from people they like. And that's another thing that we would really try to help move the needle from novice to expert on is what's your personability. Like, if you can't find those connection points with the audience, you will just be a talking head.

Ray Schloss: And if your competitor comes in after you, and they're more personalized than what they do, you're going to lose. And I'll give you an example of this. We had a situation at Microsoft one time. This is a number of years ago. Microsoft Elvis goes to market with partners. So this was a sales opportunity in New Zealand. I wasn't there on-site, but I had to do the debrief on it with some of the sales consultants that were involved. And this was a surgical device manufacturing company that made replacement joints.

Ray Schloss: Okay. So they made artificial hip joints, artificial knee joints, etcetera. So our team went in and they use the default Microsoft demo data at that time, which was built around a bicycle shop. So it was supposed to show how you could do supply chain around bicycle parts, right? The customer was so offended that nothing was tailored towards their industry, their own personalized needs. They literally stopped the presentation, said, get out. Everybody left their director who was responsible for the evaluation, contacted Microsoft directly and said, never bring that partner back. And if you can't bring someone in who knows our industry, we don't even want to talk to you. We're done.

Ray Schloss: We're going Salesforce. And that Bruce was just like one of the most ointment examples of novice versus expert. They obviously didn't prioritize discovery to really tie the presentations and the messaging around the needs of the customer. They did it based on what was easily accessible and comfortable and had nothing to do with what the customer really needed. So the good thing is I actually don't know what the second round of that ended up. I didn't hear any more about it. So hope, I guess it went better the second time, but they did get a different partner and went in and obviously tried to tailor everything to the needs of the customer based on discovery. So that's the kind of thing that can happen when you're not paying attention to these issues that we're about.

Bruce Scheer: I love it, Ray. Yeah. So I guess the big point is an expert. They prepare, and they tailor, and they make it relevant in that buyer's eyes. You make me think about I did a project, Ray, a while back with IBM. And, do you remember WebSphere? You probably competed against it. Yeah. Yeah.

Bruce Scheer: So, yeah, Ray, you'd probably dig it too. This guy, what was a business value guy, really dyed in the wool business value guy, but he was a leading WebSphere at the time. And they built a WebSphere look alike software application that they would use to custom before some of those demonstrations for clients. So it wasn't really WebSphere that they were demoing software that looked like and behaved like WebSphere, but it had the client's logo. It had the client's information in there, that prospect where they could go, oh, wow. You know, that's us. Oh, this is sweet. We want it.

Bruce Scheer: Yeah. So, it was such a smart investment in a sales tool that they could do that. Of course, WebSphere is too complex and hard to do that on its

Ray Schloss: own. Yeah. So they

Bruce Scheer: had to build out a a fake WebSphere to customize, but very, very powerful on getting the customer to fall in love with it.

Ray Schloss: I've never done anything like that ever. Bruce.

Bruce Scheer: No, no,

Ray Schloss: no. No, I mean, to you, we, we flat out absolutely did that. If we knew that like the solution had the capability of doing, but in getting it to do that in a short timeframe to prepare for a presentation was not technically feasible. Did I use Photoshop and mock up screens? The thing like, oh, this is it. This is dynamics 365 for, you know, yes. Yeah, I did that. You know, but, and then it would be like every once in a while, because before I was the global technical sales director, I was a technical sales consultant for 7 years on the front lines with the customers doing all this. And every once in a while, later on, get a call from somebody from Microsoft services going, Hey, I just want you to know the customer's saying that they saw something in the demo and I'm not sure how we're gonna reproduce that.

Bruce Scheer: So I'm like,

Ray Schloss: okay, well, let's talk about this.

Bruce Scheer: Yeah. But I I think the important point, though, is just creating that relevance where the customer can see themselves using that and the value of it and then tying it back to the problems that you're solving for that you discovered during the discovery process. It's just absolutely critical that full circle and that relevance within there. And then I like what you were talking about, just making sure you're personable in in that demonstration and really connecting with them. It's kinda funny, Ray. Another time, LinkedIn was selling to me wanting to sell our agency on LinkedIn. And I was having this wonderful conversation with the seller that he said, Hey, Bruce, I want to show you some stuff. And I'm like going, okay.

Bruce Scheer: We could do that. Are you sure? And he goes, yeah, yeah, yeah. It'll be worth our time. And then he went into this one way train of presentation with slide where just and feature based, you can do this, this, this, and this, and this, and just lost me. I had to kill the call with the guy. Wasn't connecting anymore at all. It just went into a one way train mode. Okay. Not good. Yeah.

Ray Schloss: That's like just going back to all these demo to win sessions that we did in preparing people during onboarding at Microsoft with in demo to win, literally, we would get these signs and would say, so what, as I mentioned earlier, and people in the audience were instructed that like, when they hit that point that you just talked about where it's like, you've lost me. So what pulled that up? And there were people who saved their, so what signs and put them like in their cubicles or their offices is just a reminder, whether you're doing it, just an initial phone call or if it's your 15th one, or you're preparing for the presentation, can't tie it to value and make it relevant to the needs of the customer. You're just wasting time.

Bruce Scheer: Yep. True, true, true. Well, great. If you could just think about some of the key step, if you wanted to move from novice to expert, what would be some of those steps or I guess, building blocks, thoughts that you would have to get you to that high level?

Ray Schloss: Yeah, I'd say one thing starting with discovery, right? Because you're not going to have a truly effective presentation. If you don't do the discovery work on the front end, we used to have a thing where we would say no discovery, no demo. And because how many times, especially if a client is looking for column fodder, because their purchasing process says that they have to have a minimum of 4 bids before they can take 1. And it's like, oh, Bruce love your stuff. Listen, we just need, can you just give us an hour demo on how you do financial management or whatever? Like, well, Ray, really, because we want to get to know you as a partner, not just a customer who's going to buy some of our software. We really want it. And I'm like, ah, Bruce wouldn't have time for that. Right.

Ray Schloss: So anyways, you're not going to win. So, if there was no discovery and they're not willing to invest the time to really help you understand their situation and their needs, you're not going to succeed. Right. So, prioritizing discovery. So, the first thing is just making sure that you get the opportunity to do discovery. The second one is I would highly encourage people to listen to audible or read books. If you prefer, I'm a listener, not a reader, but one way or another hearing from subject matter experts on how to become a better listener. How do you give pause? How do you understand the underlying message below? What really might just be the surface dialogue you're hearing and getting to the absolute key points.

Ray Schloss: What is that single message that you can walk away with that the organization is identified? If we don't accomplish this through this presentation, We're not going to succeed, find that. And then you build your presentation around it. So becoming an effective listener who also knows how to ask great questions to get down to the core issues is the primary step of being able to then set up to have a great demo. And then for the demo and the presentation, sometimes I've seen where doing dry runs are absolutely essential, but I've also seen very, very seasoned sellers and technical sellers that didn't need to do that because they were so comfortable with their craft, that they knew how to get into the flow and do it without a dry run. But as a general rule, getting the team together, doing a dry run, and especially if you can have like a sales manager or someone be an objective observer so that they can give that presentation feedback. It is a great step to being demo ready. Also, you could have that person role play being the devil's advocate that we've all run into presentations. How many times will really Bruce, is that really how that works? What if we don't want to use that database structure and like bringing up the questions that may come along the way in your presentation.

Ray Schloss: So I would say those are 2 great steps you can take to being, really discovery and demo ready.

Bruce Scheer: Awesome. No, I'll take it. I sent you another episode that we had done, Ray. This woman in Joy Raines talked about how to be mindful and discovery, and that really anchors what you were talking about, just being a great listener, really finding those issues that are gonna compel someone to act and respond to those in your demonstration. So very savvy. Well, Ray, it seems like we're kinda rounding out here. Any other points of advice that you'd have for anybody and how to be discovery and demo ready?

Ray Schloss: Yeah. Be fun. Like find some way to make it fun. And the more you can have a message in your presentation, that is genuinely a passion point for you. The more effectively you're going to translate that to the audience. So I'll give you an example for anyone who's ever seen Willy Wonka and the chocolate factory. Right? We used to have this day. I worked for a company called Lawson software out of the twin cities.

Ray Schloss: That's been part of in for a long time now, but we had this feature called drill around, which was actually really cool. You could be on any screen and a number of the different fields on that screen had hyperlinks would allow you to drill into things. Most other companies call it a drill feature. So, if you're on a general ledger posting screen and there's a company and you want to click on that and find out, well, how much we spent with this company or whatever it, this was an amazing feature that would allow you to go anywhere within the application from a single starting point on any page. And I likened it to Willy Wonka and the chocolate factory, because at the end of that fantastic movie, Willie is completely heartbroken that none of the kids had the integrity to not take the everlasting Gobstopper from Sledworth. Right. So Charlie's the last man standing him and grandpa Joe, and they get to the end and they're in Willie's very bizarre little office space with everything's half of a statue and half of them clocks only ticking in one direction and everything. And Willie's like, get out, get out.

Ray Schloss: And grandpa Joe's all offended. He's like, why you're nothing but a cheat and a fraud and blah, blah, blah, blah, blah, blah. Then Willie turns around. He's so fizzy lifting drinks and you did this and you did that. And then, you know, and he's get your good day, sir. Right. And you're just like, oh my God, like, this is so painful. And then Charlie reaches into his pocket and he sets the everlasting gob stop on the desk and Willie Wonka reaches over and puts his hand on the Gobstopper.

Ray Schloss: And, and I can't remember the exact quote. Now I haven't done this presentation in years, but it was something like no greater deed than that from the heart of the child or something like just so well written. And then he turns around. He's like, Charlie, you won, you know? So they're all, there's all this excitement and he's like, come on. I want to show you around the factory. We're going to take the walk evader. And Charlie's like the walk evader, Mr. Wonka, why the walk evader? Well, an elevator goes up and down, but a walk evader goes inside and outside upwards and downwards and sideways and backwards.

Ray Schloss: And, and so they're in the walkabator and there's this one button that's got this red circle around it. Right. And Willie's like, Charlie, I've pressed every button in the walkabator, but this one, but if you press a Charlie, it's going to take you wherever you want to go. And that's Lawson drill around folks. Right. So I was like, it started that one point and it'll take you wherever you want to go. A lady literally came to tears one day, like in that. So my whole point in that, Bruce, was like, find something that you can tell a great story around.

Ray Schloss: Mhmm. That's got passion. That's got emotion. That's gonna be fun. And you will be way more memorable with those things. Nobody's gonna care about you being able to change the quantity on a line item and it's already down, but they will care that you touch their heart in some way. So in conclusion, find a way to make those heart connections. And there you go.

Bruce Scheer: Oh, powerful. Yeah. That's really wonderful. Storytelling is so key. Well, Ray, thanks so much for being on the show. This was a blessing for sure. Yeah. I do. Would you like to offer how to reach out to you with?

Ray Schloss: If you just go to ray schloss.com, I actually have that forwarding to my LinkedIn page. LinkedIn is the best way to get ahold of me. I don't do other social media really, but I'm a certified hypnotherapist. So, I work with people on that. And I also produce custom meditation music for a couple of companies that individuals as well. So, people are like, Hey, I need to hear something that's going to help me perform better. Get past this challenge in my life. I'm all about doing that. And you can just ping me on LinkedIn and I'll be happy to say hello.

Bruce Scheer: Far out. Excellent. Ray, thanks so much. Really appreciate the contribution here.

Ray Schloss: Absolutely. Thank you, Bruce. All the best, my friend. Namaste.

Bruce Scheer: And that wraps up our conversation with Ray Schloss on how to be discovery and demo ready. Remember, the key takeaways are prioritize discovery, become an effective listener, prepare thoroughly, and don't forget to make your presentations memorable and fun. Ray's story about Willy Wonka and the drill around feature is a perfect example of how to leave a lasting impression on your audience. If you found this episode helpful, please don't forget to like, subscribe, and share with your colleagues. For more resources on value based selling, visit valuepros.io. You'll be able to check out also our value ready assessment. It's under our resources tab. It's free, and it'll help you not only up your discovery ready and demo ready capabilities, you can focus on other aspects to up your game for 2025.

Bruce Scheer: This is Bruce Scheer signing off. Until next time. Keep focusing on value in every customer interaction.

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