In this introductory video of a five‑part series, Kevin McCann of the Executive Strategy Group explains that an accurate sales pipeline depends on asking the right, open‑ended questions to uncover genuine prospect pain. He introduces his "sales window of opportunity" framework—originally created in the early 1990s—and focuses on the first quadrant: industry events, company events, and the business consequences of unresolved issues. McCann walks viewers through a series of concrete, open‑ended questions designed to reveal (1) whether a prospect truly has a painful problem, (2) how that pain impacts the individual and the organization, and (3) whether the prospect is willing to pay to fix it. He stresses the importance of understanding industry‑specific challenges, board‑level priorities, upside/downside consequences, prior attempts to solve the issue, metrics of success, priority ranking, and compelling events that create urgency. The video concludes by summarizing the three key objectives for uncovering pain and sets the stage for the next steps in the pipeline‑fixing process.
Chapters
Hi, I'm Kevin McCann with the Executive Strategy Group. And in this video series, we're going to cover how to fix your sales pipeline now. And the information we're going to cover here is appropriate for both sales management asking questions of sales reps, and sales reps asking questions of customers or prospects. So I'll explain how that applies as we go through the videos. So the first question I have for you is, how accurate is your sales pipeline? Do deals typically look more optimistic in the beginning of the month than they do at the end of the month? Do your prospects mysteriously push out deals mid month or at the end of the month because they're too busy to buy your product or service right now? Or are you frequently surprised by any of these occurrences? So in this five part video series, we're going to give you some ideas to address all of these issues and how to fix your sales pipeline right now. In this video, we're going to discuss how to uncover the business challenges, issues and pains that your prospects feel. So to set the stage for this series, we want to make it clear that asking thoughtful and meaningful questions is a critical skill to master if you're interested in having an accurate sales pipeline and ultimately shrinking your sales cycles. So I know you were probably told as a sales rep starting out, or if you were coached by people in the past, that you need to listen more and talk less. Or perhaps you were told that God gave us two ears and one mouth for a reason. But unless we ask the right questions and interview our prospects and sales executives the right way, there really won't be much for you to listen to. So in order to come across clearly and as a thought leader in your market and to show your customers that you really know what you're talking about, you must become skilled at asking the right questions. So here are a couple quotes that I like to help drive this message home. We create our destiny by the questions we ask. The types of questions we ask determine the types of answers we receive. So a lot of the structure of the questions we're going to go through in today's video is to guide your prospect down a path that you want them to follow. So we can do that by asking particular questions. And the third one is the seeds of change are implicit in the very first questions that we ask. So again, setting the stage with the right types of questions. Another is we manifest what we focus on and we grow toward what we persistently ask questions about. So it's really key that you ask open ended questions as much as possible. Questions that can't be answered with yes or no. And the reason is that when you get the prospect to open up, they're going to share with you a little bit more about the struggles and the challenges that they're facing so that you can really build a strong value proposition or innovate your value around their particular need. So I'd like to introduce you to this concept called the sales window of opportunity. Now, this is something I created back in the early 90s when I was a sales executive for a high tech company and I went from inside sales to outside sales. I got promoted after being an inside rep for about a year and my first week on the job as an outside sales rep, I got a sense for what it was like to be dealing with a militaristic sales management where, where every week we sat around the table, me and my other sales rep peers and our sales manager would drill us asking questions of all shapes and sizes. And when you didn't know the answer to the question, you get a verbal beating, basically. So I decided very quickly I did not want to be the guy getting the beating. So I established and built this system to make sure that no matter what deal I was working on or what project I was working on, I, I had the answers to every single question. Not only for my manager, but for me to know where should I be spending my time. So we've broken it out into quadrants here, and for this video we're going to focus on the first quadrant and we call it the industry events and pain, company events and pain and business consequences if not resolved. So I tend to spend more time in this quadrant than any other. And ultimately your goal is to find out, does your prospect truly have pain? First and foremost, do they have an issue? Do they have pain? Is there a project for you to work on? The next question is, how is that pain affecting them personally and their organization professionally? Are they committed to paying to fix that pain is another one. There's a lot of people and a lot of companies out there that have pain, but they're not necessarily committed to paying to solve that pain. So in this quadrant, this is what you're going to try to figure out. Ultimately, if there's no pain, they're certainly not going to pay to fix it. But even more, if they do have pain and they're committing that to you and they're sharing that with you, then ultimately we want to make sure they're willing to pay to solve that pain. So here's some questions I'm going to share with you that you can go through and ask your prospects or if you're sales management, ask your sales execs about every single deal in the pipeline. First question is what are the key industry pains, issues or pains that have impacted your business and how do you plan to address them? This will get you to open up the conversation and notice it's an open ended question. What are the key industry issues? And frankly, I'd recommend going into the meeting or having that first conversation already knowing what some of those key industry issues are. So for instance, if I'm selling technology to a healthcare company, I need to know that there's HIPAA issues, that there's meaningful use issues going on in the industry and how my solution might be relevant to those industry issues. So that when I start asking these questions, I'm sharing with them that I understand their industry. I basically understand what's going on from a challenge standpoint with their peers at other companies or other institutions. And it starts to set the stage that I'm not just, this is not my first rodeo, I understand and specialize in their market in solving the challenges that they're basically currently faced with. Another question, how does the board of directors see this industry issue impacting your business? Now the reason I would ask board of directors is that if you're dealing with a director level or a VP title or even the executive suite, frankly, you want to understand what are the directives coming down from the top, you know, from the top down and understanding what their priorities are. Because typically the marching orders are going to go downhill and this is going to create whatever the activities or the projects that your director level or VP level tit are working on. So how does the board of directors see this? Is this urgent? Is there a huge issue going on right now has to be solved or is it a Q2, Q3, Q4 issue? So that's a great question to start exploring that arena. Next is what are the possible business consequences that may develop due to this issue or this particular pain surfacing? So the goal here is you want to get a sense for what's the win in this for them, right? The upside if they solve this issue. And then conversely, what's the downside if they do nothing? If this pain stays there, is this something you and your company cannot live with? And if so, how quickly does that have to be solved? So I want to understand upside and downside of both elements of this particular challenge or scenario that they're faced with. And there it is, right? What are the upsides to your company if this issue is resolved. And then furthermore, has your firm or your company already attempted to respond to this industry issue? And if so, how did it go? Was it something that was a complete train wreck and we've got to start from scratch, or we're almost completed and you can help us push the football over the goal line? This will give you a sense for what's the sense of urgency and how close is it to being resolved in their mind. Next is how would the elimination or the reduction of this issue help your corporate goals this year? So what I want to get into here is metrics. I want to understand what to them equates to success. So how do they define success or how do they define resolution of this particular issue? So another secret tip is always ask why. This will give you the ammunition that you're going to need later. If they say that it's not important or we decide to push this project out in those first meetings, I want to understand why this is an issue and you want to plan for that black hole moment. I call it the time between you sending them a proposal and when the deal is closed. We deal with a lot of clients that have a challenge in this area. I had the first meeting, it went great. I sent them a proposal, we had a conversation, and then I haven't heard from them in the last three months and they won't return my call and they won't return my emails. We want to be very clear on what the pain is and why they have to solve this pain or this issue. So a couple questions around that could be how important is it for you and your company to resolve this issue? And when they say it's very important, say why? How does this stack rank among all of the other projects that you and your executive team have on their table? Another question is, as I mentioned, is where does the stack rank among your list of priorities? So not only do we want to know where it stack ranks among the list of priorities for the individual you're speaking to, but also from a company standpoint. So see, in some cases you're competing not against other vendors, you're competing against other projects that are going to cost money and require an investment. And they're trying to figure out should we do this one first or do your project first? Next question is, what is the compelling event that would help expedite this change? You know, if it's, well, if we don't do it, then our servers are going to crash or our, our web infrastructure is going to go down. Oh okay. Well what would the impact of that be? It would be huge. We would lose all of our customers or whatever the issue is. I want to understand what's the compelling event or the compelling sense of urgency that would help expedite us moving forward and helping you solve this issue. So in summary, when we're going through the pain your goal is to find out the following. Do they truly have pain that they can't live with? We want to make sure that they can't live with the pain that they have. Next is how is that pain affecting them personally and as an organization? And then third is are they committed to paying to fix that pain? So again it's not enough to know that they have pain. We want to understand why they consider it to be pain and that they're committing to paying to solve that pain. Thanks for your time. We'll see you on the next video.
