5 “W” Questions and Customer Success: How to Break from the Surface Problem to the Core

October 31, 2016

Burke Alder

Customer Success Strategist


As a customer success manager (CSM), you have a lot on your plate. Each day, you’re tasked with growing customer accounts, introducing new products and services to your contacts, building relationships, solving problems, and connecting dots across an organization. It’s easy to get caught up in the here and now and lose sight of the bigger picture. When problems arise – and they do often – it can be difficult to step away and discover the core problem. Here is a simple process you can follow to arrive at the core problem and quickly devise a strong. We call it the 5 “W’s”.

“W” Questions to Arrive Find the Core Problem

When you were in elementary school, you learned about the 5 “W” questions, including: Who, What, When, Where, Why? These simple one question words could be used to dig deeper into any situation, allowing you to evaluate the problem from all sides.

In fact as a child, you likely recall being asked these questions when a problem arose by teachers, your parents, or other supervisors. At the time, it probably felt like you were being interrogated. “Who were you with?” “Why did that happen?” “Where did you go?”

Asking Questions is Imperative to Finding a Solution

Even though you probably disliked being asked those questions as a child, the 5 “W’s” can teach us a lot about evaluating situations – whether positive or negative – from all sides to really dig into the root of the negative situation.

As a CSM, asking questions is an imperative skill to learn. And not just questions of your customer, but questions about the situation in general. Below are the 5 “W”, reframed as questions to ask to break from the surface problem to the core:

5 “W” Questions to Consider and Customer Success

1. Why

Why did it happen in the first place? Were there specific causes?

Why did the situation escalate into a problem in the first place? While the question may seem elementary, it’s important to start here – at the beginning. From your vantage point as a CSM, you have good insight into the people, the processes, and the surroundings of what may have led to the situation.

Is there anything that happened that may have triggered it, such as a product failure, an incorrect invoice, an unfulfilled commitment, or an argument? If anyone else internally was involved in the situation, be sure to ask for their perspective as well. Sometimes piecing an accurate puzzle together takes several different viewpoints.

2. What

What happened in order to cause the situation? Has it happened in the past?

Similar to asking why the situation happened in the first place, it’s important to ask what happened. What exactly is the situation you are digging in to? What were the key events that took place in order to escalate the situation? Equally important to ask is whether or not this is the first time the problem has occurred.

Perhaps your organization is going through a tough spot with a product or a service and several other similar situations have occurred with other customers or even within the same account. If so, compare the situations and determine if the problems are identical or if there are key differences. If the problem continues to arise across other customers or the same customer repeatedly, be sure that a manager or executive is aware of the problems, and offer a suggested solution.

3. Who

Who was involved in the situation? Is someone involved that shouldn’t be?

Using the analogy of sports, who were the players on the field? Who was involved internally and who was involved from the customer side? Often times, situations become problems when too many are involved – each with their own points of view. We’ve all heard the expression “too many cooks in the kitchen”. This applies to customer success, too. When too many are involved – no matter how good their intentions – it’s easy to step on toes and confuse others who are supposed to be involved. Were there individuals involved in the situation who should not have been? On the contrary, was someone missing from the equation? If a main contact is out on personal leave or if a key stakeholder wasn’t part of an important meeting, problems can also occur.

4. When

When did the situation(s) occur? Are there any patterns?

Do you notice anything particular about when the problem occurred? Was it after a long weekend, or late in the evening? Did it happen over a weekend, or while a main contact was out of town? Timing is everything, and that’s certainly the case when it comes to this question. Be sure to evaluate the time of the problem – even if it’s ongoing – to determine if perhaps “bad timing” was part of the problem. You can imagine that if a customer’s overseas vacation was interrupted by a problem back in the office, they probably weren’t too happy. Be sure to also look for specific patterns. For example: Do you often run into similar problems Monday afternoons? Are there product maintenance updates or scheduled downtimes during that particular window? Getting a clear view of the timing and corresponding patterns is critical for digging deep into the core of a problem.

5. Where

Where did the situation occur (ex: online, via phone, email, in-person)?

While this may seem unimportant, the communication channel used can mean all the difference in how a problem erupted. Some individuals are better communicators in person, while others communicate best via email. Did the problem unravel through a specific channel? If so, was it a new channel, or a channel that isn’t used as often with that customer? If you and your customer are used to speaking on the phone once a week, but you communicated about a challenging situation via email, it may be an uncomfortable form of communication. Be sure to evaluate the communication channels involved in the situation and look for red flags for how the situation may have escalated, or may have become worse simply because of the channel used.

What Questions Does Your Team Ask to Get to the Core of the Problem?

It’s inevitable that as a CSM, you will run into challenging situations with customers. Unfortunately it’s not a question of if, but rather when. In fact, some situations may escalate quickly for no apparent reason. How are you and your teammates prepared to tackle challenging situations and get to the core of the problem?

Asking questions is an important part of uncovering the core and resolving the issue – and perhaps even tackling future problems before they happen. What are some questions your team asks when the going gets tough?

Check out our resources below for more customer success best practices and insights for how your organization can approach customer success with the customer at the center:


5 Ways to Surprise & Delight Your Customers

Customer Success as a Culture: Customer Success Leaders Edition

Blog Posts:

The Golden Rule of Customer Success: 8 Guiding Principles

6 Listening Techniques of Great Customer Success Leaders

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