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

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?

"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