Show Me Where It Hurts: the Customer Success Manager’s Diagnostic Guide to Business Pain

6 minute read

November 17, 2017

Show Me Where It Hurts: the Customer Success Manager’s Diagnostic Guide to Business Pain

I’ve written previously about the value of understanding the customer success manager (CSM) as something like a heart surgeon. A CSM is the consummate expert who cracks open a company’s chest, peeks  inside and wields his surgical tools (products and services) to perform the necessary procedures.

Today I want to press a little further into the medical analogy, but from another angle. We’re going to talk about how you, as a CSM, can go beyond your customer’s stated pain to identify the deeper disease and use your unique position to assist them.


The Difference Between Pain and Disease

My wife works in healthcare, and almost every day she has a new story to tell about patients who walk into the office and demand that she prescribe them certain medications.

These patients typically present a vague set of painful symptoms they think could easily be cleared up by an antibiotic or a bottle of pain meds. Rarely do they want to sit with her and talk at length about what might truly be going on beneath the surface.

They’ve got the pain, they “know” what they need and they want it now.

The problem with this, of course, is that pain never exists in isolation. It always bespeaks something more, an underlying condition in need of some resolution.

Treating the pain without addressing the underlying condition,  may mask it for a short time. But once the meds wear off, the pain will come  back— and with a vengeance!


A Threefold Taxonomy of Pain

Brian Norusis, COO at e-Builder, classifies three levels of business pain:

1. Tactical/Operational Pain

This is the most superficial level of pain. It often involves a specific operational complaint: “I’m tired of fiddling with Excel. I need a product that’ll automatically populate and spit out shipping invoices.” 

2. Motivational Pain

This pain is slightly more complicated. It involves external pressure, either from a customer or a superior: “Our COO is not pleased with our invoicing procedure. Worse, I’m getting complaints from accounting about uncollected funds. If I don’t figure this out, I’m going to lose my job!”

3. Emotional Pain

This is the most profound level; it cuts to the heart of why people experience pain in business: “My oldest is about to graduate from high school. If I lose this job, I might have to raid his college savings just to feed our family. He’ll be hindered, and I’ll be humiliated.”

Norusis’ taxonomy here is a helpful one, but limited insofar as it focuses on the individual rather than the corporation he represents.

Yes, as a CSM, you want to understand the pain behind the individual with whom you’re interacting. But, don’t stop at their pain alone. Your job is to penetrate beneath the first layer to identify what the organization needs, why it needs it and how you can solve its problems at a deeper level—one they may not even have noticed.

In what follows, I’m going to list some questions to ask and ways to dig deeper on both of these levels. As you work through them, keep in mind that these questions are diagnostic tools, not masters. Ask the questions, but let the natural flow of your conversation and investigation dictate what you talk about and when.

How to Identify Business Pain

Whether we’re talking about healthcare or customer success management, a practitioner’s most potent tool is the simple question. Sure, there will come a time for specific tests, measures, analytics and all that, but before you can even know what to measure, you have to start by talking to people on the ground.

These questions are designed to help you determine where the pain is in an organization. In the following section, we’ll look at questions designed to get you beneath that to the deeper and more abiding problems in their organization.


Six questions to ask:

1. What are your strategic priorities for the short, medium, and long term?

This is a foundational question. To help someone along their journey, you need to know where they’re going, right? The most significant pain points that a customer will experience are those that keep them from executing their strategy effectively.

2. What gets discussed most frequently at team meetings and corporate gatherings?

Similar to the first question, this one will help you tease out the explicit and implicit priorities of an organization.

3. What’s your biggest roadblock to growth?

Here’s where you can drill down on specific sources of pain. Anything that gets in the way of the company’s forward momentum is going to stick out like a sore thumb.

4. What’s the biggest thorn in your side right now?

This question is similar to the previous one but gets at it from a more emotive angle. The most personally vexing issues an individual will face don’t always align with the more serious ones on an organizational level. It’s important to identify both kinds, so that later, you can sort out which is more critical and prioritize accordingly.

5. What do you spend the most time and energy on?

Sometimes, businesses and individuals can be blind to their pain. A team may hammer away at a task for 80 hours a week, not realizing that they’re throwing good labor after bad. Asking where their time goes will help you diagnose whether that time is well spent and whether they should be feeling some pain when they’re not.

6. What does your boss get worked up about?

You’ll rarely interface with the top dog at your client company. That means the bulk of your work will be done with a mid-level employee. On one level, that means your success won’t just be tied to the organization’s success, but to that employee’s success. Leverage that to your benefit. It’ll not only gain you an advocate in that organization, but it’ll give you an insight into organizational priorities from an insider’s perspective.


Analyzing Client Pain

The previous section was designed to give you a set of discussion points and questions to  determine a company’s priorities and pain points. Answers to the above questions will give you specific insight into where and how an organization is suffering.

If you’re going to get in there and make a difference, however, you can’t content yourself with a surface level understanding of these things. You need to drill down deeper to the why beneath them.


Here are the follow-up questions to ask:
1. What is your gut telling you about the problem?

As I mentioned above, there will come a time for objective measurements and testing. But the best way to get there is through the subjective judgment of your client’s employees. Take time to listen to their gut-level sense of what’s going on. It’ll give you better initial insight than a spreadsheet ever could.

2. What would success look like at this point?

Clients often think they already know the solution to their problems (see the example of my wife above). Though they’re often wrong, you can learn a lot about the true nature of a problem by considering the client’s own perception of what’s wrong and how it ‘needs’ to be fixed.

3. If I solved your problem today, what difference would it make to your organization?

This is a variation on the previous question but worked out writ large on the organizational level. By asking this type of question, you can connect pain with the wider corporate picture. This will help you tap into the broad, systemic issues at play and allow you to prescribe more comprehensive solutions.

4. Do you have a plan to address this?

Perhaps the greatest value you can provide to your client is to help them develop a concrete plan to tackle the pressing issues in their business. This takes you beyond the realm of a ‘typical’ customer support person or account manager and puts you right at the heart of the client organization. From there, you’re in an incredibly promising position to make your product a must-have component to that organization. If you want to decrease churn and increase up- and cross-sells, this is exactly where you need to be.

5. Who on your team is already working on this issue?

This question will help you on a number of fronts. First of all, if the answer is ‘no one,’ then either the ground is fertile for you to dig in and get to work, or the client isn’t all that serious about the issue. Second, the answer may give you further insight into the key players you need to tap to further explore the issue.

When a patient walks into a doctor’s office and asks for an antibiotic, they’re not really looking for a small bottle of pills. They just want someone to take the pain away.

When a customer buys one of your products, subscribes to one of your services or engages you for consulting, they’re not just looking for something to spend money on. They m need you to take their pain away—to help knock down the barriers between them and their goals.

As a CSM, it’s on you to be an excellent diagnostician—to know what their pain is, where it comes from and how exactly to apply the healing balm of your company’s products and services.

So be a good salesman, consultant and customer support representative all rolled into one. Get to the bottom of that pain. Dissect it. Analyze it. Get to know it intimately. Then write the prescription that you know will take it away for good.


Share Your Thoughts

Your email address will not be published. Required fields are marked *

Kenny S.

Written by Kenny S.

Have an Article for Vanilla's Blog?

Send us an email to [email protected] with your topic idea and we'll circle back with our publishing guidelines.

Subscribe to the Community Corner Newsletter and get expert insight and analysis on how to get the most out of your online community every Friday.
[contact-form-7 id="5700" title="Newsletter Form"]

Request a Demo

Schedule a product demo now.

Contact Us