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20 Questions For Introducing (Good) Friction Into Your Deals​
Generally speaking, you want to try to remove friction in your business... faster funnels, fewer clicks, frictionless onboarding etc.

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But in enterprise sales, friction can actually be a tool for driving deals.

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This is by no means a new concept. SPIN Selling used implication questions to create tension. The Challenger Sale made “constructive tension” mainstream. And frameworks like MEDDIC all push the same thing: ask the tough questions, force clarity, test commitment.

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Why? Because friction filters out fake deals.
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If your champion can’t answer questions about budget, decision process, or exec alignment, you don’t have a deal.

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So to that end, I thought I'd share a list of 20 questions I ask to introduce friction in my deals.

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This should go without saying, but just in case...
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These questions are meant to be asked (and re-asked) over the course of the deal cycle, which is usually weeks or months in MM or ENT selling.
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DO NOT use these to play "20 questions," in your first call or there WON'T be a second call.
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​So, in no particular order, here are the 20 questions:

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1. What's driving this project? - Ask this in your first meeting.​
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2. Is this a sponsored project? - This is a better way to ask about budget or funding.​
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3. Who would need to sign off on it? - This will provide insight on key stakeholders and decision makers.​
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4. Who else will need to be involved in this evaluation? - This will help you map out who needs to participate in things like demos, pricing conversations, InfoSec review, legal etc.
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5. What happens if nothing changes and you stick with your current setup another 12 months? - Consider the response to this carefully. If this can't be articulated by your champion, more discovery is needed. ​
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6. Why not just stick with your current solution? - Similar to the above, why make a change? Get a clear response and rationale or you might be column fodder (i.e. you're being used to make a business case to renew with the incumbent solution).​
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7. When would you like to go live with this? - Helps establish a solid timeline.​
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8. Where do we stack rank against other vendors you are looking at? - I love this one, especially when you get a good honest response.​
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9. Why is this a priority now? - This will likely involve some deeper level questioning after they respond. This will help you build your business case and drive urgency. ​
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10. What's the best way to engage [EXEC] and/or [IT LEADER]? - This will help you begin to plan your process for exec peering.
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11. When do you plan on making a final selection? - Helps create urgency in the process and manage to milestones. ​
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12. If the vendor selection deadline were today, would we be vendor of choice? - Loaded question, but if they decline to answer, prepare for impact.​
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13. What's in it for you? - You'll need to build some rapport before you plant this one on your champion.​
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14. Who signs the paperwork for this? - Get a name!​
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15. What would it take to get this done by [DATE]? - This is a trial close, the answer will tell you a lot about​
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16. What has killed deals like this internally in the past? - Story time, pay close attention to the response.​
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17. Who on your team is likely to push back on this purchase, and why? - Uncover the detractors early and work on addressing their concerns.​
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18. Which other initiatives would get delayed or deprioritized if you move forward with us? - Competing priorities are a silent deal killer.​
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19. What legal or procurement roadblocks have slowed you down on similar projects in the past? - This will help you plan ahead so you don't get stuck waiting months for a signature.​
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20. How will your team measure the success of this initiative? - Uncover the North Star in terms of metrics and then you can build a strong business case for your solution.

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I hope this list helps you pinpoint which of your deals have the most potential, so you can focus on the 20% that will get you to 80% or more of your target.

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If you'd like this in a printable format so you have it handy, you can grab that here.
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Now I want to hear from you. What are your go-to questions?
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What would you add to this list?
-Jesse

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