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Podcast Recap: How To Ask Strategic Open-Ended Questions (with examples) PT. 2

Updated: Jan 31

Asking open-ended questions as a Customer Success Manager is a skill we all need to develop––but it takes hard work and practice.

The first episode of the Grain Grow Retain podcast with Bob London was a hit. It's true––plenty of Customer Success professionals found the episode so insightful that it left the podcast creators, Jay & Jeff, no choice but to bring Bob back (#tonguetwister)!

The details

In this post, we are recapping an episode from the Gain Grow Retain podcast called “Level up your relationships by asking open-ended questions” with Bob London.

If you missed the last recap, here’s a quick note on who Bob London is. He comes from a Marketing & Sales background and he's passionate about bringing the customer’s voice to the strategy table. He’s the founder of the Chief Listening Officers, they focus on helping companies listen to their customers.

The Customer Success community is growing and the creators of this podcast have a lot to do with it! They bring on guests in Success and outside of Success to help us answer tough questions with tactical insight.

Let’s get into the 3 takeaways:

  1. Building relationships with open-ended questions

  2. 3 real-life examples of open-ended questions

  3. Why are we scared to ask these questions?

Building relationships with open-ended questions

Bob comes from the Marketing/Sales side so the way it all started with him was meeting with companies and quickly finding out that they didn’t have a handle on what was on the customer’s mind. Asking open-ended questions was about getting the insights to reposition the company, getting the brand/messaging aligned, etc., but ultimately it is about the relationship.

The transparency has evolved from employers + employees––employees demanding more transparency––and moving into the customer realm. That transparency breeds trust and these sorts of questions make room for that.

Jeff jumped in to say that we hear a lot of noise around scaling––everyone wants to scale things. But he wants to do the opposite. Over the last 3-4 months, he’s sent personalized messages to every person that has joined the Gain Grow Retain community or followed their LinkedIn page and he’s gotten nearly a 75% response rate. That’s unheard of! And this is what Jeff believes will help grow the community.

It’s about building relationships by doing things that don’t scale and that includes asking open-ended questions. Towards the end of the episode, Jay asked about scaling open-ended questions (mainly wanting to know for the companies with much larger customer bases) but Bob argued against it. This is something you want to dig into and ask follow-up questions to get the truth from the customers.

3 real-life examples of open-ended questions

In the episode, Bob gave us 3 examples of open-ended questions so we’re going to go into each one but before that, a warning:

⚠️These are bold questions that you should only ask if you wanna hear the truth ⚠️

Let’s take it away!

Example #1: If a competitor reached out to you today would you ignore them or engage? On a scale of 1 -5. 1 being you’d ignore them and 5 being you’d reply and be interested in what they had to say (a continuation from Pt. 1)

This question we covered in the last post but we’re going to dig deeper:

The benefit of this question is that if the customer says “I would engage with a competitor”, that gives you the opportunity to ask “why?”, “what are you seeking?”, “what’s missing that makes you curious about what the competitor is going to say?”. In Bob's experience, the answers that you get will help you build the relationship.

On the other end of the spectrum, if the customer says “I would delete the email” this is great! It doesn’t give you much insight but it is better news. To follow-up on this one, you can ask “why wouldn’t you?”.

Jeff also added that if the score is 1, it can make some room for developing the customer into an advocate and/or a reference. Bob adds that if they say I would delete the email, another follow-up could be “is there something we’re doing well that you’re not finding elsewhere?”. This can help uncover the uniqueness or value prop of the product/service.

Not everyone agrees with this question though, Bob has had some of his clients say “why would we ask that? We don’t want them to know that competitors exist”. And that’s an okay reaction so Bob is okay with eliminating the question but does let his client know that they’re not going to know the truth that they need to know.

Example #2: Hypothetical speaking, what would you lose if we suddenly go away––we’re not going away, just a hypothetical but what would your job be like without us?

This hypothetical can go one of two ways:

  1. You may find that you’re indispensable - but you can’t rest on that, you need to ask why their life is hard without your tool.

  2. They’ll say “we’ll figure out another way to do it” - And this could be because there are plenty of alternatives in the market.

Either way, it gives you a chance to understand them. So if they say “it would be disruptive but just for a week” it gives you an opportunity to uncover what value they’re missing or just not getting.

Example #3: what would make you a customer for life?

This question is one that Bob leaves towards the end.

And by far, it’s the most insight producing question Bob has in his arsenal. Once he drops the question, there's usually a bit of silence and a lot of times the customer will say “that’s a great question”. And if they are taking too long Bob will say “Look, it’s a figurative question. I don’t mean sign a contract for the rest of your life”.

What they say a lot of times is “no one has ever asked me this before” and this blows Bob’s mind. We all want customers that never leave but we’re not asking what that looks like from the customer’s perspective, so just ask!

What you get from their answer is the delta between their current experience and the experience they need moving forward or how their business will be changing and how our product/service will need to align.

During the first 100 calls where Bob asked this question, he got a little anxious asking this question because it does require a different frame of mind from the customer, you’re really asking them to think. But here’s the thing, Bob has asked this question in nearly 2,000 calls and he’s never had someone misunderstand the point of the question.

Jeff mentioned that he’s seen that question before and has put it into practice. Some of the responses he’s gotten have been customers jokingly saying “keep the price the way it is”. But other customers would say “If you keep doing what you’re doing on the account management side––for context, this team was engaging with customers, were proactive, helped customers get what they needed––we’re gonna be happy for a long time”.

The thing Jeff loves about that question is that it is so open-ended that people will answer it in so many different ways. This gives you a chance to bring in any department to listen to the feedback.

People get scared of this question because they don’t even want to suggest that they’d go away but customers always seem to appreciate the context in which you’re asking these questions. They get it! They know you’re trying to think of ways to get answers that aren’t cliche and so the way to do that is to not ask questions that are cliche.

The importance of follow-up questions

The follow-up questions are what Bob describes as the logs on the bonfire of customer intimacy and the kindling for those questions go in between. It’s the “why did you say that?” or the “what do you mean by that”?. For example, one of Bob’s clients, a CEO, was talking to a prospect and the prospect said “oh yeah, I can see how this can help some of our customers with safety” and the CEO went on to expand on safety. It turned out that after 20 minutes, his definition of safety was totally different from the prospects. The follow-up question should’ve been “what do you mean by safety?, What does it mean from your perspective?”.

Why do you think people are scared to ask these questions?

Who really wants to rock the boat by asking these questions?

Bob isn’t suggesting that these questions aren’t good but what do we do with these answers? Sometimes the answers can go way past CSMs so we need a framework in which we decide what to do with the answers afterward.

Bob believes it goes back to the over “processization” of the way things need to happen in order to scale. It feels like we can’t do anything out of a certain swimlane.

A lot of it though is not knowing what the answer is going to be and that’s why Bob loves these questions. When we think about Sales, they’re always asking questions to listen, and then they’re good at positioning the product against what they just heard. But they’re generally looking to ask questions where the answers go down a certain path. With Success, it should be a little different.

“Don’t be afraid to be different, be bold, prod, and ask questions where it gets people to think.” - Bob London


  • Want to build a relationship with your customers? Ask open-ended questions!

  • When you ask non-cliche open-ended questions, be prepared to hear the truth from customers––and sometimes that hurts.

  • Sales asks questions to lead the prospect down a specific path, Customer Success is not like that.

Shout outs

Thanks to Gain Grow Retain for hosting Bob on their podcast! You can go follow Gain Grow Retain on LinkedIn. And if you want to hear more from Bob, follow him on LinkedIn.


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