How should sellers run discovery conversations?

Sean Murray · Jan 24, 2024

A seller doesn't need to know the buyer's specific business better than they do — the insight comes from reframing the problem using patterns seen across many similar accounts

Talking to 30 firms in a persona each month gives you a view of the community that any single buyer lacks

18:33 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Brendon Cassidy · Mar 8, 2024

Reps should know the customer's problems and psychology before ever getting on a call; long discovery calls conducted for the rep's own benefit are disqualifying

You are supposed to be an expert talking to these people every day; their problems aren't infinite — there are only about three or four paths, and you should know every turnoff on them in advance

10:18 20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

Brendon Cassidy · Mar 8, 2024

A salesperson should know their buyer persona's pains and opportunities as well as the buyer knows themselves, so nothing on a call ever comes as a surprise

The set of problems a given persona has is finite — usually three or four paths — and every great team he's been on had them mapped in advance

Scope: applies to teams selling to a defined persona (VPs of sales, VPs of marketing, CFOs)

11:54 20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

Ben Fiechtner · Aug 2, 2024

Sellers should show up with a strong executive point of view built from qualitative and quantitative research on the client's business, rather than just asking questions

Arriving with an opinion on where the client should go and how you uniquely get them there gives you a disproportionate chance of a seat at the table; it's the same as bringing your boss a problem plus a proposed fix

Scope: you won't always win the deal

5:50 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

John McMahon · Nov 28, 2025

The best reps spend their time preparing for customer meetings and, like lawyers leading a witness, ask leading questions they already know the answers to.

Having sold many deals, they already know the pains in the customer's process and can steer to them via reference stories.

Scope: applies to reps with a year or two and many deals under their belt

19:44 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Harry Stebbings · Mar 21, 2026

Buyers today are unwilling to spend their time being qualified, so sellers should already know the customer's situation rather than discover it in the call

people are cautious and hesitant with giving their time to anything

6:04 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Lori Jimenez · Aug 2, 2023 · hedged

Curiosity is one of the most important characteristics of a great salesperson, and active listening means letting each answer inform the next question — including listening for the answers you don't want to hear

You need to hear the red flags and misalignment, not just confirmation, so you can build alignment through the sales engagement

Scope: stated as her opinion

24:51 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Lori Jimenez · Aug 2, 2023

A bad sales call is one where the rep marches through the enablement question list as a checkbox exercise instead of pausing on where each answer leads

You waste the customer's time and your own because you learn nothing from the conversation

Scope: question lists are fine as a guide

26:22 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Doug Adamic · Sep 8, 2023

Great listening in sales requires being fully in the moment and discarding preconceived notions, so you can judge whether you can genuinely help the customer.

Being centered and mindful is what lets you connect with people from all walks of life and levels, and genuine interest in improving their business is what makes the connection real.

4:21 20Sales: Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

AJ Tennant · Oct 23, 2024

The skill today's junior AEs most struggle with is being creative, flexible and adaptive inside a live conversation rather than running a prescriptive script

They prepare a structured approach and stick to it instead of actively listening and morphing to the customer's specific situation, which is what the best sellers do

Scope: about more junior sellers

3:45 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

John McMahon · Nov 28, 2025

Reps should listen with the intent to understand rather than the intent to reply, asking five or six layers of questions before talking about their product.

If you're planning your reply you aren't getting to the bottom of what the customer is actually saying.

24:07 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

John McMahon · Nov 28, 2025

The single most important thing in sales is becoming a great listener and centering the customer rather than yourself, including preparing extensively and staying reluctant to discuss product capabilities until the right moment

It's not about you, it's about the customer — you should understand as much about them as possible before pitching capability

Scope: framed as the distilled 60-second version of all his advice

65:03 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Lauren Schwartz · Oct 19, 2022

The best skills a salesperson can develop are insatiable curiosity about what's possible and the instinct to ask forgiveness rather than permission — treating rules as suggested guidelines.

Selling requires going outside the box and taking prospects into uncomfortable territory, which you can only do if you don't wait for permission.

4:54 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Kim Graves · Jun 27, 2025

Sales can be practiced as a data-driven, therapist-like discipline of asking questions to find the real pain, rather than the stereotypical version people imagine

Learning this from Dannie Herzberg showed her sales could be done differently and turned it from a stepping stone into a long-term career

66:31 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Ron Gabrisko · Aug 4, 2025

Failure to sell often means the founders aren't listening to customers; even today, good salespeople are the ones asking good questions to learn what the market wants from the product

Two ears, one mouth — market understanding comes from listening, not pitching

24:48 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Shaunt Voskanian · Mar 21, 2026

The most important skill in sales is curiosity — genuinely understanding the buyer's situation and circumstance

5:53 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Doug Adamic · Sep 8, 2023

The purpose of discovery is to gain unique information competitors can't access, and then use it to change the customer's buying criteria toward your solution.

Thoughtful preparation gets you to information others can't reach, which is what lets you position your solution as the unique way to solve the business problem.

5:38 20Sales: Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

Sean Murray · Jan 24, 2024

Reframing the problem the buyer thinks they have is what unlocks deals that product features alone cannot

The Dentsply case: 500 reps failed to sell ergonomic drills until one rep researched hygienist carpal-tunnel absenteeism and quantified it as ~$700k of lost business a year for a dental practice, reframing the purchase

19:46 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

John McMahon · Nov 28, 2025

The commonly skipped step is failing to understand the customer's process — its individual steps, the pains in each, quantification of those pains, and how your differentiators align to them so they enter the decision criteria

Whoever locks down the decision criteria locks down the deal, so you win by getting the customer to test against your differentiators

11:45 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Matt Rosenberg · Oct 4, 2023

Buyers only open up honestly if they see you as a trusted partner with insight to share, so you should open discovery with an insight from research rather than questions

Sharing that other similar customers struggle with the same issue makes them feel not alone or isolated, which gets them talking

26:41 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Sean Murray · Jan 24, 2024

Teaching the buyer something about their own business should be the first stage of the sales process, and reps who open with basic researchable questions shouldn't bother calling

If you can teach a buyer something they aren't already thinking about, they will engage with you

Scope: He has run 'teaching hypothesis based selling' as stage one at three companies

14:12 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Sean Murray · Jan 24, 2024

Discovery as traditionally practiced is dead and should be replaced by teaching

Technology lets a seller learn almost everything about a buyer within minutes before the call, so asking questions you could answer yourself is lazy

17:47 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Shaunt Voskanian · Mar 21, 2026

Being great at enterprise tech sales today requires being prescriptive — bringing insights and teaching the customer — while still mixing in curiosity

buyers are busy and what they really want is to know what your best customers are doing that they haven't figured out yet

Scope: enterprise tech sales; curiosity and prescription must be done simultaneously

6:28 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Lauren Schwartz · Oct 19, 2022

Effective discovery follows an outside-in sequence — current state, negative consequences of inaction, imagined future state, then the positive business outcomes — using only open-ended questions rather than yes/no ones.

Yes/no questions cause you to miss what the customer is truly experiencing, and pushing past the technical solution to 'so what, and then what' surfaces the real value drivers: revenue, cost saving, risk mitigation, time to market.

6:20 Structured outside in discovery sequence with open ended questions surfaces value drivers

Sean Murray · Jan 24, 2024

Teaching and reframing works for horizontal products too, by going persona-based and carrying insights across industries, though it is not easy

Within a function like talent acquisition the problems are largely the same across retail, tech and biotech, so you can teach one industry how another approaches, e.g., diversity and inclusion hiring

21:49 Persona based teaching transfers across industries for horizontal products

Ron Gabrisko · Aug 4, 2025

A sales pitch should be a series of discovery questions about the customer's challenges and goals rather than a presentation, and should lead with value and time to value rather than technical detail

The point is to find where you can add value; Ron demonstrated this in his own Databricks interview by answering 'give us the pitch' with questions, and found the existing deck was heavy on technical content and light on value

11:26 Pitch should be discovery questions not a presentation leading with value

Ron Gabrisko · Aug 4, 2025

A successful sales meeting has four components: generating rapport/trust, generating interest, identifying challenges, and driving to a defined objective

Without a game plan and a specific objective (next meeting, POC, introduction) the rep has no way to know if the meeting worked

50:04 Four part framework rapport interest challenge objective

Jordan Van Horn · Aug 17, 2022

Asking every prospect 'why did you take this call?' surfaces a small set of reasons, and those reasons why people engage turn out to be the same reasons they eventually buy

At Monte Carlo there were three reasons people got on the phone, and those became the three reasons they bought the tool; they map back to the problem you actually solve

11:17 Ask why they took the call to surface true buying reasons

Shaunt Voskanian · Mar 21, 2026

A sales rep's core job is to map the customer org, define what a best-in-class deployment looks like, and close the gap between that and where the customer is today

That gap, worked through discovery, new business meetings, and champion-building with insights and a point of view, is what creates opportunity

19:59 Define a best in class target state and sell the gap

David Schneider · Sep 11, 2024

Salespeople should spend at least as much time listening and asking questions as talking

Questions, not talking, get you closer to the customer's motivation and their real reason to buy

27:12 Listen and question at least as much as you talk

Kim Graves · Jun 27, 2025

Without psychological safety, customers and founders will withhold the real answer.

A fear-based environment makes people hold back instead of telling you the truth.

11:05 Psychological safety enables honest discovery answers

Kim Graves · Jun 27, 2025

Sellers who love their own product suffer from premature pitching syndrome and blow the discovery stage by talking about features instead of asking questions.

Both at Slack and Notion the product is loved and customers enjoy hearing about features, which makes it hard to stay in pure question-asking mode; good discovery talks about the company, the person, their challenges and risks without mentioning the product at all.

11:34 Product love causes premature pitching that undermines discovery

Matan Grinberg · Jun 13, 2026

You should never go into a sales conversation trying to sell; you should try to understand the buyer's problems and see whether your solution actually fits

Engineers in particular shut down if you come in selling, whereas genuine curiosity works and lets you assess real fit

44:44 Enter to understand the problem not to sell especially with engineers

Matt Rosenberg · Oct 4, 2023

Deals are won or lost in discovery: bad discovery leads to long, drawn-out losses while good discovery leads to quick wins

Salespeople move too fast once they hear something they can sell against; understanding the value of solving it gives you a business case and close plan

23:57 Discovery must quantify value before pitching