Am I multi-threading?
Does this initiative have C-Suite visibility
What’s a comfortable communication cadence for your team moving forward?
Is there a true compelling event that started this initiative?
How can I stand out from the competition? (paperflight, quick responses, being a human being)
How are you aligned to their North Star Initiative?
Obtain information to create a business case
Please let me know whether [DAY/TIME] is the easiest time for us to connect.
Is there a day this week that’s easier for you than [DAY/TIME]?
Would you like to meet on [DAY/TIME]?
Does a call on [DAY/TIME] work for you?
Can we make a plan to get together on [DAY/TIME]?
How’s [DAY/TIME] look on your end to chat?
Do you have 30 minutes to hash this out on [DAY/TIME]?
Are you available to connect on [DAY/TIME]?
How about a quick call on [DAY/TIME]?
Do you have time on [DAY/TIME] to meet?
Are you available to discuss on [DAY/TIME]?
Is [DAY/TIME] open on your end?
How’s your calendar look on [DAY/TIME] to meet?
Let’s cover everything you want to know about [X] on [DAY/TIME]. Does that work on your end?
If I can deliver [X] at a meeting on [DAY/TIME], will that work?
Would getting [X] by [DAY/TIME] help you move things forward?
What are the challenges you’re facing that you’d regret not solving six months from now?
Why would you regret not solving that challenge six months from now?
Help me understand the most nagging challenges you face when it comes to [Domain you sell in]?
How satisfied are you with [Process or Solution in place]? How top of mind is that?
How highly does [initiative you’re building] rank on your “priority list?”
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 [domain], what would that be?
Earlier I asked what challenges you were facing that would derail you, and you shared this with me. Can you help me understand how this would derail you?
Can you walk me through the ripple effects (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?
Mind if ask an awkward question? What kind of ripple effects is this having on YOU?
What's driving you to solve this issue now rather than later?
How is this challenge affecting your [insert specific implication your problem-area creates??
What are the downsides when it comes to...
What effect does that have on...
How often does that cause...
What does that result in...
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?
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?
AT THE END – Pull up one slide that gives your company social proof