top of page

Podcast Recap: How To Ask Strategic Open-Ended Questions (with examples) PT. 1

Updated: Jan 31

“How to ask customers better questions”

“How can I be more strategic with my questions”

These are some of the common questions that I see posted on places like LinkedIn or in Customer Success communities. We want to ask better questions!

And we want to master this because it does two things:

  1. Gives us insight directly from the customer

  2. Builds relationship and credibility

Now, I’ve been searching around for a podcast episode that didn’t just cover the surface of asking better questions but that actually provided real tactical examples. And I didn’t find one... I found two! This is a two-part post in which Bob London takes us to school on asking better questions.

The details

In this post, we are recapping an episode from the Gain Grow Retain podcast called “Customer Success Managers can get more strategic” with Bob London.

Bob London’s tagline is “listening first, market better, grow faster”. Bob is a career marketing executive and at some point, as a consultant, he felt like there was so much guesswork going into the strategic process. You had every voice – CEO, Founder, Head of Marketing, and Head of Sales saying “here’s what we should do” and the voice that wasn’t present was the customers.

Bob decided to approach things differently, before starting the marketing, he first wanted to talk to customers to uncover insights because listening to your customers is so underrepresented in what organizations do. He’s the Founder and CEO of Chief Listening Officers which helps b2b companies develop marketing strategies by putting customers first.

The Gain Grow Retain podcast is hosted by Jeff Breunsbach and Jay Nathan. They focus on sharing conversations about growing and scaling subscription businesses with a customer-first approach.

Let’s get into our 3 takeaways for this 2-part post:

  • Five strategic questions to ask

  • Get a seat at the table by asking your customer this question

  • Building confidence with practice

Five strategic questions to ask

Because of the pandemic, we’ve probably heard thought leaders and CEOs saying things like “this is the time to hug our customers tighter”.

Companies are seeing a slow down in new revenue and they’re turning to Customer Success. Finally, the light has been shining on Success and Bob sees Customer Success stepping up.

The pandemic has also brought about some changes in how we communicate with our customers. For example, we can’t force a QBR on a customer that’s working from home with kids running around and a whiteboard with more tasks on it than ever before. The truth is that our customers are distracted.

Instead of going about a typical QBR, we need to carve out time where we really want to understand what’s on their whiteboard. The whiteboard is just a fraction of what’s going on on their brain. It’s important during a regular business review to say things like “I just want to see how things are going... I’m not asking if you’re staying or leaving, I just want to know how your industry is doing”. This is going to help you empathize! If your customer serves the hospitality industry, you need to know that! Make time and space to talk about what’s going on with them.

There’s no reason that this exercise doesn’t continue past the COVID-19 lockdown.

Moving away from the checklist approach

Our goal should be asking more questions that are geared towards getting to know their perspective rather than asking them how your software is doing. The best conversations start and end with “let me just hear what’s going on with you”, ask them what’s on their whiteboard now that wasn’t there 30-60 days ago.

It’s hard for the customer to open up about their perspective when your agenda makes them feel like they’re filling out a checklist. To get away from this, ask a lot of open-ended questions and then use tiny phrases that accelerate the conversation. These phrases could be things like “what did you mean by that?” “Why did you say that?” and “can you explain a little bit more about that”. When you ask these questions, it shows that you’re listening. Because there are so many interpretations of terms that mean one thing to a vendor and what thing to a customer, you have to get rid of any misunderstandings.

Another point that Bob brought up a lot is the idea of agenda-less listening––check out his slides on what it means., It doesn’t mean don’t have a plan going into the call. It’s a way of getting insights from a very strategic positioning/brand exercise but in the CS world, have an agenda for your meeting. It’s not an interview and while you have a list of questions, lean into any discussions and emotions your customers show.

*side note, here are some tips to follow when asking open-ended questions

“What did you guys talk about after I left the room?”

If you ask cliche questions, in cliche situations, you’re going to get cliche answers.

Bob was working with a company where he built a relationship with the CEO. The first meeting he attended was with the leadership team, it was the kind of company that was very deliberate and cautious about decision making. They were also very reserved so Bob wasn’t getting much feedback from them. The meeting ended and after getting home, Bob sent the CEO an email asking for a 5 min meeting. Instead of saying “how did the meeting go” Bob asked, “What did you guys talk about right after I left the room”. When you ask questions that have a specific edge that they’re not used to hearing you get better insights. When the CEO responded it wasn’t all good things but it’s important not to debate, instead Bob tried to address anything that he could.

So as a CSM, after the QBR, it’d be great to ask “what did you guys talk about right after that meeting?” and their answer might be, “we’re busy and moved on to the next meeting” but you’re sending them the message that you’re willing to ask a courageous question because it may be a negative response. There’s a freshness to this question because it breaks through the noise of day to day business talk.

Hypothetically speaking

Another question Bob likes to ask customers comes in the form of a hypothetical scenario:

“Imagine you’re on a plane and you strike up a conversation with the person next to you and it turns out, they’re a global renown expert in your field. What’s the first thing you’d ask them?”

The customer may say “what do you mean an expert? In CS, software, etc.” this is where you say “you can decide what they’re an expert in” because you don’t want to give them any guardrails. The question they ask is something that they’d ask a thought leader and it’s YOUR area of expertise too. This lets you know that they are looking at you as a vendor, not as a resource.

A lot of times conversations end up being about the software instead of the job they are trying to accomplish and the industry they’re a part of. This sort of question can get you away from talking about the usual. Jeff, one of the hosts, weighs in to say that the more value you can bring to the customer outside of your product, the more credibility and value you bring to the relationship.

It’s your obligation as a vendor to find out what’s on their mind and how you can help them.

Get a seat at the table by asking this question

What gives CS a seat at the table is not the job title, it’s the insights that they can bring to the table.

Another question that requires some courage is this one:

“If a competitor contacted you tomorrow, how likely would you be to engage on a scale of 1 - 5. 5 you’d be interested in meeting them and 1 being you’d ignore the email.”

To dig deeper, once they give you the rating, ask them why and then the next question is “if you did talk to that competitor, what’s the next question you’d ask them?”. Their response gives you the delta between how you’re positioned in the customer’s mind versus what they’re missing, seeking, or curious about.

If you ask multiple customers and your average ends up being 3, this is the insight that you need to bring back to your team––they want to know this! You are able to put together strong qualitative data points when you ask better questions.

Getting better with practice

So how do we build the confidence to ask these questions?


Effective roleplaying and recordings are crucial. Within your team, find the space to roleplay asking open-ended questions. You should also be recording your calls and listening to them to help you identify improvements.

There’s no question that people under prepare, whether it’s a QBR, etc. and it’s not their fault they are busy but really who gives a speech without practicing?

Jay, one of the hosts, shares that before they give any external presentations, they give a presentation internally and you get some harsh feedback in those meetings because they trust each other. But when they skip that step, they end up making those same mistakes in front of their audience.


  • Follow up open-ended questions with tiny phrases to accelerate the conversation

  • Gather insights from open-ended questions that can help you score a seat at the table––even without the leadership titles

  • You need to build confidence around asking open-ended questions so practice by roleplaying and listening to your recorded calls for opportunities

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.

Here’s an extra golden nugget from Bob you may find helpful:


bottom of page