Part of The B2B Sales Process
Earn Trust
In order to be able to ask many questions during the discovery stage, you need to ensure the prospect will open up to you.
The more they open up and you learn, the more likely to close the deal and build a strategic/long-term relationship with the client.
For them to open up, they need to trust you.
In order for them to trust you, there are 2 approaches, which can be combined:
Personal connection
This is what a lot of traditional people (including my mother) think great Sales is about.
Connecting with the prospect on a personal level.
- Be friendly
- Be genuine
- Be interested in them
- Be interested in their personal challenges
- Be interested in their personal goals
- Be interested in their personal pain points
- Be interested in their personal success
- Be interested in their family
- Be interested in their hobbies
- Be interested in their business dreams/aspirations
Expertise showcase
Based on experience (working with clients in same industry), or research (eg early days of startup/product):
- Show them you know what you're talking about
- Show them you know their industry (macro trends, competitors, etc)
- Show them you know their business ()
- Show them you know their challenges (based on ICP)
- Show them you know their pain points (based on ICP)
- Show them you know their goals (based on ICP)
The reality
No one can master all of the above.
It's a combination of elements, from one or both.
I fare far better with the Expertise Showcase approach, being an introvert geek. And this has led me to great success in Sales.
Do what works best for you, using as many elements of the Personal Connection or Expertise Showcase approaches as you can.
This will kindle the Trust for the prospect to understand that it's in their best interest to open up to you.
Like with a doctor.
Questions to ask in the discovery process
Why questions are the most important ones, and can be chained together to get to the root of the problem.
Business pain questions
● What are the challenges you’re facing that you’d regret not solving six months from now?
● Why would you regret not solving that six months from now?
● Help me understand the most nagging challenges you face when it comes to x?
● How satisfied are you with [pain area your product solves]? How top of mind is that?
● How highly does [x problem] rank on your “priority slide”?
● Just to confirm… is this “THE” challenge we should be discussing? Or are there others that are more top of
mind for you?
● If you could wave a magic wand and solve anything when it comes to [pain area] what would it be?
● I want to be sure I’m clear about [challenge they’re talking about]. Can you tell me more about it?
● Can you give me an example?
● How long has this been happening? How often does this happen?
● What have you tried in terms of solving it? How did that work out?
Cost Of Inaction questions
See also Cost Of Inaction (COI)
● Can you walk me through the ripple effects this {challenge} is having on the rest of the business?
● How is this challenge impacting the business as a whole?
● Who else does this challenge impact (function, person), and how?
● How much would you estimate this challenge has cost you/the business?
● How does it impact you personally?
● What’s driving you to solve this issue now rather than later?
● What are the downsides when it comes to…
● What effect does that have on…
● How often does that cause…
● What does that result in…
● How often does that lead to…
Solution questions
● To what extent is it important for you and the business to [solve challenge just discussed]? How would
you prioritize it among your other priorities?
● What do you think you to need to solve this challenge? How do you see that benefiting you?
● Have you thought about [insert your unique product capability here]... to what extent do you think that
would help?
● What advantages do you see from the desired capabilities you just mentioned you need?
● What are some of the ways you see [benefit your product delivers] benefiting you?
● What business outcome would that most move the needle on? How much would that be worth?
● Mind if I ask an awkward question? Why is that meaningful to you?
Decision process & closing questions
- What progress has been made on your side since our last discussion?
- What’s changed since last we talked?
● Can you walk me through the steps you and your company need to take to make a confident “yes/no”
decision on this?
● Who are the people that will be involved in each of those steps? How is each person involved? Can you tell
me about each person’s decision criteria?
● How are you thinking about funding this project?
● What circumstances need to be met for us to execute a commercial agreement by x-date?
● What would derail us from getting things done from here?
● Is there any reason for us to not move forward with this now?
Social
"We have 512 features, I'm not sure which ones to demo exactly that would make sense for you. Can you help me understand more about what is important for you, so we focus on the right things during our limited time together?"
.. and/or use the product demo to drive discovery, as per Matthew Darrow ... ie a "choose your own adventure" demo style.
Sources & References
- Chris Orlob / Linkedin
- MEDDICC
Queue
the 1 truth about discovery calls no one is talking about
27 Apr 2025
Subject: the 1 truth about discovery calls no one is talking about convert 70% of disco calls —> qualified opportunities
Hi Nic, Discovery calls are the foundation of every deal you'll win (or lose) this year. Yet most sellers continue to run them ineffectively, focusing on the wrong elements. After analyzing thousands of discovery calls across my career, I've identified exactly where most reps go wrong - and what top performers do differently to achieve exceptional results. Generating over $50M in revenue for companies like MongoDB, Qualtrics, and LaunchDarkly taught me a foundational truth: Great discovery has very little to do with the questions you planned and everything to do with earning the right to ask them. Here's what I've discovered after coaching thousands of discovery calls: Most reps waste 20+ minutes (70% of the call) on uncomfortable surface-level questions Buyers immediately check out when asked things like "where are you based" or "describe your day-to-day role" The best sellers don't show up with questions - they show up with a point of view I've developed a 5-part framework that consistently converts 70% of discovery calls into qualified opportunities: Understand why they took the call and what would be a win for them Confirm or adjust your point of view (based on pre-call research) Learn their current state relevant to their stated priorities Balance questions with insights (make it a conversation, not an interrogation) Sell meaningful next steps based on their needs This approach transforms discovery from painful interrogation into valuable conversation - and it works across any industry. I break down the entire framework in my latest video below: Drop a comment letting me know which part of the framework resonates most with you - I read and respond to every comment. Here's to discovery calls your prospects actually enjoy, Kyle Unsubscribe | Update your profile | 113 Cherry St #92768, Seattle, WA 8104-2205
None
- Focus on Earning Trust: Successful discovery calls prioritize earning the right to ask questions, not simply delivering a prepared questionnaire.
- Avoid Surface-Level Questions: Reps waste time with questions like location or daily roles, which immediately disengage buyers.
- Top Performers Offer a Point of View: Successful sellers present a relevant perspective before asking questions.
- 5-Part Framework: The framework includes understanding buyer motivations, confirming/adjusting perspective, balancing questions with insights, and suggesting valuable next steps.
- Transformation: The approach shifts discovery calls from interrogations to engaging conversations.