5 Questions to Ask Every Customer

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By Kristen Hayer

No Success on the Road post this week, although I had a blast traveling with one of our consultants, Amy Mustoe, to Atlanta and Seattle. Instead I’m taking on our main blog post, and I’d like to share my perspective on a topic that has surfaced many times over the past few months: Good questions to ask customers.

We teach a class that offers a research-based framework on questions called, as you might suspect, “Asking Great Questions”. During those classes and workshops, I’m always asked, “What is the best question?” or “What are the right questions?” I think it’s challenging to come up with questions that fit any scenario, so we tend to focus on each of our clients’ specific scenarios. That said, I do think there are common questions that can benefit you in many situations. So, here’s my list of all-time favorite questions:


If only we could all be 3-year-olds again and ask why about everything! When you’ve worked for a company for a while, you tend to buy into all of the marketing rhetoric you’ve heard over the years. “Customers are interested in X, Y and Z.” or “Customers fall into these 3 profiles.” Marketing teams need to bucket prospects and clients and hit them with the messages that resonate with the most possible clients. By asking “Why?”, as in “Why do you value our product?” or “Why do you want that feature?” we are able to move beyond the marketing messages and into a discussion about what matters most to each of our customers. Every customer is different, when you know how you can use that to demonstrate value.

How does this impact your business?

Most CSMs are really good at discovering problems they can solve for their clients. Indeed, most CSMs spend way too much time solving technical problems, instead of looking at the business issues that truly effect their clients. Go beyond questions about problems, and ask questions about the impact those problems are having on a client’s business. Questions like “How much is that costing you?” or “What stresses does that place on your team?” or “Are you under pressure to hit numbers?” are much more meaningful to clients, and will give you important information to help tailor your messages to each customer.

What do you value most about our solution?

We make a lot of assumptions about what our customers value. Money? Of course. Everyone values adding to the bottom line. Saving time? Sure. Who doesn’t want a lot more hours back in their day? I’ll point back to my first question: Why? Why does this matter to them? And how much does it matter to them? Money? What is your customer going to do with the money you save them? How will that help their company grow? Is that meaningful to them? Time? How much time will be saved? Is it enough for your customer to care? What will they do with that time instead? The answers to these questions that dig a little deeper will help you understand the priorities and goals of your customer.

What are your biggest initiatives right now?

This is such an easy question that it’s almost like cheating. When a customer tells you about their biggest initiatives (and you ask good follow up questions like “how does this impact your team?” or “what will this initiative do for your clients?”), you’ll learn what your customer cares about, what their priorities are, and how you might fit in. Teams that ask this during executive business reviews or annual renewal meetings will get the information they need to develop goals that demonstrate ROI or talk about the renewal in a way that truly resonates with customers.

What is the best way for us to partner on this?

Customers have a variety of different needs, and some of them may fall outside of your expectations of structure and timeline. While you shouldn’t bend your company to fit all customers (that way lies madness and a business that doesn’t scale) you might be able to adjust a bit to better meet their needs. In addition, positioning the relationship as a partnership, instead of positioning yourself in a service role, also requires the customer to have some responsibility for the outcomes. Asking and discussing this question puts you squarely in the role of strategic partner.

I don’t want to oversimplify: Questions should always be tailored to your knowledge of and relationship with your client. The questions on this list are simple, but also very powerful. Use them to kick off what will be some amazing, strategic discussions with your clients.

The Success League is a customer success consulting firm that offers a comprehensive CSM Certification Program which includes the Asking Great Questions class referenced above. For more information on this training program and our other classes and workshops, please visit TheSuccessLeague.io

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Kristen Hayer - Kristen believes that customer success is the key to driving revenue, client retention and exceptional customer experiences. Her areas of expertise include developing success goals and metrics, designing the optimal customer journey, selecting technology, training teams, and building playbooks. Prior to founding The Success League, Kristen built and led several award-winning customer success teams. Over the past 20 years she has been a success, sales, and marketing executive, primarily working with growth-stage tech companies. Kristen has her BA from Seattle Pacific University and her MBA from the University of Washington.