Ten Questions to Ask Your Clients Every Year

A client of mine dodged death twice. The first instance involved serendipitously avoiding what turned out to be an infamous plane crash caused by a terrorist bomb. The second time had to do with a seemingly innocuous spot on his arm. It looked like a odd-shaped mole, and he ignored it. As the CEO of a successful, global company, he was incredibly busy and hadn’t seen his doctor in several years. He felt fine and was in peak health by almost any standard measure.

His doctor looked at the mole-like spot on his arm and told him to see a dermatologist immediately. It turned out to be a large melanoma that was on the verge of metastasizing—it was going to kill him if it hadn’t been removed immediately.  

Here’s the point: Your client relationship can seem healthy. Even radiant. But there may be something small bothering your client. It may be a benign issue—for now. But over time that concern may grow and fester, and it may even get conflated with other concerns. In other words, without regular communication and a regular, thorough relationship review process, you risk losing a client because you were unaware of their true feelings or worse, you were aware of them but didn’t take them seriously.  

A small, unspoken dissatisfaction may grow into something more deadly. By the time you react to it, the relationship may be too ill to recover.

Here are 10 questions you should ask each of your clients, every year. You don’t have to necessarily ask them all at once–in fact, 10 may too many for one sitting. And, your firm may have its own year-end institutional review process. So think of them as a way to create a healthy conversation, or series of conversations, any time of year:

Questions about the quality of your relationship

1. Could you share with me your overall assessment of our relationship and the work we’ve done for you?

This is a general question that can help kick off the conversation in a non-threatening way.

2. What have we done this past year that you have found particularly valuable or useful?

We think we know what has “added value” to our clients. But often, they have experienced value from things we’ve done that seemed minor or insignificant. You need to find out, so ask!

3. If you could change or improve one thing about our relationship, what would it be?

If a client is not very forthcoming about the first two questions, this might spur a response.

4. Are there any individuals in your organization with whom we should invest more time and build a better relationship with?

This question is especially important if you work with large clients where you need to be developing relationships with multiple stakeholders

5. Can you give me any suggestions for improving the amount, timing, or format of our communications to you and your organization?

Ideally, you should co-create–that is, collaboratively define–the type of relationship management that suits the client.

 Questions about your client’s plans and priorities

At this point, you may want to shift the conversation using several “agenda setting” questions to better understand your clients upcoming issues and challenges. After all, while asking about the state of your relationship is important, it’s`backward-looking. But asking about your client’s plans and priorities is future oriented, and most client executives are more excited about the future than gazing in the rear-view mirror.

6. What are your plans for…? How are planning to deal with…? (Tailor these to your client’s business and markets, and the challenges they face)

Remember, you don’t just want to ask open-ended questions about your client’s “issues”–you want to consistently demonstrate that you understand your client’s business environment and the key trends that are affecting them.

Another way of formulating these is to use the format of a “credibility-building question.” You state an observation and then flip it into a question. For example, I might say, “With other clients I’ve observed, there are typically three barriers to the internal collaboration required to serve clients…” I’ll list the barriers, and then ask, “I’m curious, in your organization, what do those barriers look like?”

7. As you look ahead to the next six to 12 months, what issue or potential challenges are coming up that we might helpfully think about for you?

This question may uncover more about your client’s agenda.

8. What are your most important priorities for next year?

This is a perfectly acceptable question, but it’s a bit general and clients get asked it all the time. A more personal version is,

“How will you be evaluated by your leadership at the end of the coming year? What are the key goals you’ve been asked to accomplish?”

9. As you think about the future of your business, and your various initiatives, what are you personally most excited about? On the other hand, what are you most concerned about?

I like this because it’s a “right-brain” power question. It touches on the right side—the personal and emotional side—of the Power Questions Matrix. It will help you understand what your client is truly excited and passionate about, and it can lead to a very interesting, engaging conversation.

10. Is there anything we could improve upon or change that would make doing business with us easier?

“Ease of doing business” is an underrated quality, and you might close your conversation with this one. I’ve even said to a busy top executive, “Is there anything else I can do to make life easier for you?”

Additional questions

There are a few other questions you might also ask, depending on the circumstances. For example, if this is a firm relationship and you have a designated relationship manager and team, you need to find out how the client feels about them. 

  • Could you give me your assessment of our team? What have they done particularly well? Are there any areas for improvement or weakness I should be aware of? Are there any skills we should be adding to or strengthening in the team?
  •  Could you give me your assessment of our relationship manager/account executive? What are their strengths and weaknesses?

What if the problem with the relationship is the relationship partner or account manager? This doesn’t happen every day, but I have witnessed this a number of times. An incompatible or poorly performing team member is certainly not good, but the wrong relationship manager can sink the whole relationship.

This question is also important in a B-to-B relationship:

  • If you need something from our organization, do you always know who to go to?

Do clients know how to navigate your organization? Do they know exactly whom to turn to? This question will help ferret that out, and what you learn may be critical information.

Some questions not to ask

Don’t ask “What’s keeping you up at night?” It’s a lazy cliché that salespeople have been using with clients for years. Plus, it’s a “problem” not an opportunity question. Other worn chestnuts include “What will success look like?” and “What question haven’t I asked that I should have?” Don’t ask leading questions, either—e.g., “Don’t you think you need more innovation in your organization?”.


There are some structured methodologies out there to help gage client satisfaction and enthusiasm—for example, NPS or “Net Promoter Score.” These can be very helpful. But nothing substitutes for a personal conversation with your client about your relationship, their priorities, and how you can have an even greater impact on their organization in the coming year.

copyright 2023 By Andrew Sobel

Back to top