The best way to understand customer motivation (aka pain aka desire aka wants, etc) is to study human behavior and human nature.
For a VERY simple model study the lowest levels of Maslow's Hierarchy of Needs.
For more detail study Evolutionary Psychology and Neuromarketing. Type those words in to the amazon.com search box and you'll find plenty to read.
Good marketing is grounded in a firm understanding of human nature. Once you have a good grasp of these concepts you can begin to apply them to your specific market. It's part science and a good bit of art. The key is to, as Steve Blank says, "get out of the building."
It will likely take time to develop this skill but the investment and effort are well worth it.
The "shortcut" is to work with a consultant or coach who has already studied and these things and mastered this skill. They will not only assist you in specifically finding YOUR customer's "pain points" but they will effectively lead by example. And you will no doubt shorten your learning curve significantly. Consider that there are 237 responses in the amazon search for "neuromarketing" - and then consider that a good coach can direct you to the highest impact 3 or so books.... How much time and money would that save you?
Let's talk if you'd like some direction and assistance. I wish you massive success!
From a Customer Experience perspective, where there's a failing or underperforming product or service causing the pain, there are definitely some tried and true questions. I've asked these questions on almost every engagement I've ever had across the last 25 years, and they hold true to any kind of organization. The key to identifying pain points isn't necessarily asking stakeholders what they are. It's more a matter of asking the right questions, some of them seemingly indirect, that will paint a picture for you of what's happening. And it will also clarify what's happening to your CLIENT as well.
From startups to Fortune 100 organizations to Government, the "strategy" phase of any engagement I've taken on includes the following approach:
FIRST: Identify every stakeholder, even the less obvious parties, and make sure they have a seat at the table. Or that you speak with them individually.
in addition to wanting to know how what's happening affects the business, you also need to know how it’s affecting each of those people – and their departments if it’s a large organization – individually. Who has decision-making authority, and who doesn’t? Who has the most to gain or lose? What happens to each person’s world if the project succeeds? If it fails?
Remember, success for one stakeholder may not be the same as success for another. And should those goals be diametrically opposed, you may find yourself caught in the middle of a political battle. And when that happens, you want to be absolutely sure you have the lay of the land so you know how lightly to tread, or, in some cases, whether you are fighting a losing battle that will only end in tragedy for all involved. I’ve been involved with a few of those. They last forever, and the mental and emotional stress lasts even longer.
NEXT: Ask the right questions.
The questions you ask, obviously, should be specific to the client’s business model, market, product, industry, etc. But there are more than a handful of questions that you should ask of every business stakeholder, every time. Here are the most important of those:
1. WHO ARE YOUR CUSTOMERS/USERS?
You want to get to know the people that use this product or service right now. What do they do with the product? What do they like about it? What do they expect from it? This is where, if possible, you want to involve folks who work in the call center or are directly responsible for interfacing with customers. That’s because you want to know what they complain about and how often. And you also want to know if the organization can draw a straight line from any of those complaints to lost revenue, or to customers choosing a competitor over them.
2. WHAT SHOULD THIS (PRODUCT/SERVICE) ACCOMPLISH FOR THE BUSINESS?
How does each person in the room define success, and how will each person measure that success? The measurement part matters, because any goal that can’t be measured is probably also one that can’t be achieved. And even if it can, no one will know when that’s happened!
3. WHAT'S THE LARGER, BIG PICTURE BUSINESS STRATEGY?
No man is an island, and inside a business, no product or service is either. Among all the things the organization does, there will be multiple pieces that will impact what you’re doing. You need to know what those things are so that they don’t sneak up and derail you later. In heavily regulated industries, for example, changes to the law can have a profound effect on how data is collected, accessed, manipulated and stored. Whatever you’re proposing has to be in line with those external constraints.
4. WHAT TECHNOLOGY OR SERVICE DELIVERY DECISIONS ARE SET IN STONE?
The existing parameters around technology have a profound impact in what you recommend or design or ultimately build. So you make sure IT is present and accounted for, and you ask this question up front. Every time. Otherwise you may be in for a big surprise in 3 months, part of which includes a very angry client who was looking to you to figure all this techie stuff out.
5. WHY DO CUSTOMERS CHOOSE YOU/USE YOUR PRODUCT/SERVICE?
An obvious question, to be sure. But believe it or not, in the mad rush of day-to-day pressures, tasks and activities inside a corporation, it’s not often that people to step back to consider, well why do customers care about this? When you ask the question, it often prompts people to re-examine their preconceptions. I’ve been in rooms where after 40 minutes of what sounded like a solid list of reasons, the conversation devolves into twelve people thinking WOW…we thought we knew, but, er…ah…maybe we don’t know.
I also want you to notice how open-ended that question is. That’s purposeful. You’re purposely leaving a very large gap that the ensuing conversation will fill in. And in most cases, some incredibly important things will come to light.
That's the place to start. Obviously you also want to ask about competitors who may be stealing their thunder, but that's a deep well in and of itself. I can assure you that the things I've described above simply do not change. They're universally relevant and appropriate.
Remember that as long as you're asking questions, you're on the right track. Keep things open-ended and let them paint he picture for you. Listen more than you speak. Don't concern yourself with solutions; spend time making sure you understand the depth and breadth of the problem first.
I hope that's helpful! Please feel free to contact me if you'd like to talk in deeper detail about this; I'd be more than happy to jump on a call and work through it with you.
Most of the startups that I have mentored have gotten to their customer discovery/value proposition phase where they are required to prove or disprove their value proposition and they freak right out because they want a list of interview questions.
I always tell them to ditch the questions. Approaching customer discovery with a list of questions will completely limit your responses by setting their thinking around a specific solution and then you miss understanding if your solution is even an answer to the problems they *really* have.
Instead, go back to what is prescribed in the customer validation approach and do a "day in the life" analysis. Don't assume you know what the problems are. Start with a hypothesis and then go to your customers and ask them to describe their work processes, or their buying habits, or whatever it is in the context of your product, but let them drive. Most times, they will quickly get to describing what's challenging about this process and the first things they will describe are the biggest pain points. Of course you want to be armed with some questions you can ask to drill down further, as described in some of the responses above, but listen, listen, listen. Guide them and let them talk. People will complain more than they will rave and with a skilled facilitator or business analyst, you will be able to maneouver the conversation to discover whether they actually care about the problem you think you are solving or whether you need to pivot your offering/value proposition to address what they are *really* struggling with.
Bottom line - ask them to describe their life in the context of your offering. Don't lead them to focus specifically on your solution right off the bat.