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Free Cheat Sheet Reveals:
Ultimate List of Sales Questions That SELL

“These 39 Sales Questions Will Help You Create Urgency and SELL In An Economic Meltdown"

​​​​​​​Learn how over 50,000 tech salespeople are closing more deals with these proven questions.

50,000+ tech salespeople growing their skills at companies like:

"These questions help you create urgency"

Specific, word-for-word questions that help you uncover the business problem a customer is trying to solve. They help you find problems that customers are willing to fund, and create urgency by opening your client’s eyes to the full scope of their problem."
- Oliver Bailey, AE, Ebsta

"Best questions and phrases for maximum impact"

Chris's approach to discovery led me to start asking questions I would never have thought - or dared - to ask. And I know WHY I'm asking and how to best phrase questions for maximum impact. 
- Nathan Easom, AE, Demostack



CEO of Former Head of Sales (Growth) at

The guy who helped grow Gong from $200k to $200M.

 Chris is a 'been there, done that' tech sales leader who's both DONE it himself, and trained 10,000+ sellers:

  •  Grew Gong from $200k to $200M in five years
  •  Grew personal income from $36k to $1.7M in tech sales
  •  On a mission to teach YOU how to become an 'outlier success' in tech sales

"Too much sales content is too high level, way too complex and take days to complete without walking away with any concrete tactics you can use right away. These questions and tips are completely tactical. The tips explain the concepts in a super easy-to-understand manner"."

-Mark Baskin, AE, Hubspot

“I learned more from Chris than I did in the last five years of my sales career. Full of actionable info, guaranteed to make anyone a better tech seller. Chris completely transformed my approach to selling SaaS, especially in a competitive environment.”

-Stephanie Alberti, Sales Manager, Figma

"These questions are impactful and get results. Once I implemented what they taught, my deals got bigger and closed faster. I’ve been in sales for 15 years and have done a lot of sales training.'s content is the best. Results came quickly when I implemented what I learned."

-Lauren Wesley, AE, Gong
39 Questions That Sell

Here's What's Inside

12 Questions to FIND Deal-Closing Business Pain

Uncover the REAL challenges facing your customer's business... not the 'shiny objects' they'll forget about a day later.


🔑 Unlock 39 Questions That SELL 🔑

13 'Negative Impact' Questions to Build URGENCY

Build the 'cost of inaction' and create urgency with these 13 'negative impact' questions.


🔑 Unlock 39 Questions That SELL 🔑

7 'Vision' Questions That Make Them WANT Your Product

Ask these 7 questions, and build a 'buying vision' that rigs the deal in YOUR favor (and boxes out competitors)

🔑 Unlock 39 Questions That SELL 🔑

7 'Decision Process' Questions So You Don't Get BLINDSIDED.

Ask these questions, and you'll know EXACTLY how to navigate the deal to get it done.



🔑 Unlock 39 Questions That SELL 🔑


 Plus, I'll send you a quick video on how to run deal-closing discovery... even in an economic downturn.

Start closing more deals.

Unlock the 39 Questions That Sell Here

Hey friend...

My name is Chris Orlob. And I'm thrilled to have you join the community.

Over the course of my tech sales career, I've asked and tested THOUSANDS of sales questions.

And let me tell you... there's was LOTS of trial and error. Most questions are garbage!

But these 39 questions? They're proven. Among the thousand I tested...

They're the 39 questions that WORKED. As in... closed deals.


If you're frustrated with deals slipping and stalling...

If you're under pressure to make your number...

If you're stressed and anxious about your pipeline...

Then this is the most important investment you can make in yourself right NOW.

And the best part?

It's free.

If that sounds like a good deal to you... Then let's get started together.