Context
I wrote this post through the lens of B2B SaaS since it’s more relatable to you than my context of selling sales training.
However, the underlying purpose of each question in this post remains the same regardless of what you sell. It’s the Framing of the question that changes based on your context (in this case, SaaS)
Question #1
🐲: What's an ideal outcome for this meeting?
There’s good ambiguity and bad ambiguity.
Good ambiguity = I’ve done what I needed to and now need to wait and see what happens
Bad ambiguity = I’m missing critical context
Asking this at the start of a meeting clarifies the buyers position.
Where are they at in terms of readiness? What are their expectations? This is critical info to know when you don’t have a lot of context.
You can follow up their answer by asking:
🐲: and assuming you get [recap what they tell you], what happens next?
or
Asking these questions helps you to avoid wasting time by understanding their buying / evaluation criteria upfront.
Chad note: notice how I didn’t ask “what would you like to get out of this meeting?” .. this wording suggests an unfair dynamic where the buyer will be doing all the taking.. and what do you get in return? NOTHING.
Asking “What’s an ideal outcome for you?” sort of creates this giant Frame and invites the buyer to fill in the details with their expectations while you sit back and look at how you want to deal with that Frame
Question #2
🐲: What would need to happen for it to be clear that implementing our solution was successful and justified the investment?
Define their success metrics upfront. You’ll quickly know if you can get them there or not. Why wouldn’t any seller want to know this in the first meeting is beyond me. Too many are addicted to Hopium.
I want clarity. Always.
Asking this question also reframes the conversation from ‘cost’ to ROI / Value. The buyer will define success from their perspective to which you can reference later in the sales process as the sort of North Star to keep things on track. You’re not just the seller, you’re also the quarterback of your deals.
Whatever they tell you can also be used as a nice Moral Authority frame:
🐲: At the end of the day/Bottomline/What’s most important here is you are trying to do [their definition of success] with your business so everything should be in support of that goal.
Question #3
🐲: Why can't you do that today?
This questions reveals the perceived obstacles to achieving the success metrics in question 2. Many times your buyer will give a long winded answer to this question revealing which challenges are both significant and emotionally relevant to them. It’s all about paying attention to the non-verbal cues as they speak and knowing which thread you want to pull next.
If you are a true domain authority, you know 9/10 times the problem the buyer tells you is never the real problem to be solved.
This sets you up to challenge them and take control in this part of the meeting.
FEW.
Question #4
🐲: Why now? What happens if you wait?
This question is best asked indirectly. Asking straight up “Why now?” is riskier as many sellers robotically follow their MEDDPICC frameworks ask this question so bluntly which raises buyers defenses.
Variations:
🐲: Why can’t it wait?
🐲: Why not 6 months from now?
🐲: Nobody wakes up one day saying they need new software. What happened / What is going on?
The objective here is to see if there is any compelling event / urgency. This can be any sort of internal / external pressures driving the buyers need to change.
You need to be feeling out the vibes here. There should be enough energy behind the buyer that’s led them to this point of needing to take action.
‘Feel’ their answer in your body as your source of truth. Can’t rationalize this.
If you’re not convinced by their answer, you need to gently press for more context.
Question #5
🐲: What is it about [feature/solution] that you believe will be right for you?
You can emphasize the solution early in the meeting.
or You can emphasize the feature if discussing the product.
The Framing of this question gets the prospect selling themselves on the feature / solution.
Pay close to attention to their answer as they will be indirectly telling you how to Frame your solution back to them.
Weave in the points they tell you are important to them into your demos as you hold the mirror up.
Question #6
🐲: The investment range to work with us is anywhere from X to Y depending on your requirements... any issues with those initial numbers?
Reframes ‘cost’ to ‘investment’ while also addresses logistics in the first meeting.
‘Depending on your requirements’ is a different way to say ‘because’. It creates a strong justification. i.e Because pricing depends on your requirements, I need to do more Discovery in order to understand your requirements.
'Initial' numbers is disarming & non committal yet enough context to quickly Disqualify out tire kickers
There is no sense in continuing if the buyer isn’t able and willing to buy what you have.. unless of course you just want to make new friends. Have fun with that.
You can argue that one should wait until value is delivered first before talking numbers. In complex deal environments selling to well funded companies where the range varies greatly, sure.
But the vast majority of salespeople aren’t selling into these segments. So why dance around the talk of commercials? You do realize many of your buyers aren’t even paying attention to your demos because all they can think of is how much this will cost them.
Dumb tactics enforced by incompetent management.
When in doubt, talk commercials early. Give a range of pricing. Something. And if the buyer is budget sensitive, then deal with it then. Don’t try to convince them to justify the cost by showing them a demo. Waste. of. time.
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