How to ask better questions?

I've observed some CS executives ask amazing questions to C-Level executives and decision makers that gets them talking about their problems, not only in relation to the product but their overall business. I understand 'Asking Good Questions' is a skill that takes time to master. I also believe it is a science.
How should someone approach this? Any reading materials that come highly recommended, or a podcast that helps with this?

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Jared Orr

Honestly, I just got in the habit of asking anybody about anything. Family, friends, LinkedIn connections, colleagues, classmates were all people I would ask questions to. I'm sure many of my questions were dumb or simple but it got me in the habit of asking a question and then listening with the intent to learn rather than just respond. When I listen with the intent to learn, my response is usually more genuine and the conversation is much better.

Vasu

Thank you, these recommendations help. I'm slowly learning that Customer Success is part consultation and part sales skills. Debra Calvert's Discover is on my reading list now.

Cheers,
Vasu

Vasu

Thank you Jeff. This goes into my weekend listening bucket.

Vasu

Yes, I'm constantly reminding myself of that.
Asking open ended questions is a great, it has worked for me in some conversations, however - this approach doesn't work with a few executives. They just give really short, tempered answers. How would you approach such conversations? What needs to change here to get them engaged and conversing?

Thanks,
Vasu

Vasu

That's a great recommendation. I've read and shelved Dales's book. Will definitely go back to this.
Regarding active listening - how did you consciously start practicing it? Any tips on getting started with this would be great.

Thanks for the reply. Cheers.

Sidd

Great question @Vasu , Adding to what other mentioned, I also think practice makes perfect. The more you invest time on actually talking to customer, understanding their perspectives, you will eventually get the questions. Key is to be engages & involved in the conversation. One more thing is to focus on asking Open Ended Questions (What does success mean to you? How do you see the CX team transform within the next 2 years?,etc)

Jared Orr

@Vasu How to Win Friends and Influence People is a fantastic book that takes a deep dive into relationship building.

In my experience, my questions have improved as my listening skills have improved. The better I get at active listening, the better and more though-provoking my questions become.

Cheers!

Marijn Verdult

@Vasu I would tap into the knowledge of the sales profession here. For example the book Never Split the Difference talks a lot about tactical empathy and also try the book DISCOVER by Deb Calvert

[Deleted User]

@Vasu this is a great prompt - we've been looking into this a bunch recently. We recorded an episode for the Gain Grow Retain podcast that highlights some questions to be thinking about. @Bob London joined us and talks a lot about asking strategic questions.

https://podcasts.apple.com/us/podcast/gain-grow-retain-b2b-saas-customer-success/id1476256054?i=1000478192263