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Ask the right questions
Daily Sales Newsletter April 25, 2025 |
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In today’s issue:
Salman Mohiuddin: Unlock sales magic with connections
Kyle Asay: Smart discovery that earn better answers
Marcus Chan: Closing discovery starts with numbers
Mor Assouline: Asking the right questions every time
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Unlock sales magic with connections
Salman Mohiuddin’s post walks through a high-impact discovery call that hit all the right notes.
1. Research about your prospect
I knew they had just moved cities, so I asked what inspired the change.
⇢ This sparked a meaningful connection.
↳ Show them you’ve done your research.
2. Ask on their company model
I walked through my understanding of their company:
“Looks like your business model is [insert insight], how are you driving growth?”
⇢ Show curiosity, not ignorance.
↳ Let them share pain points first.
↳ Understand their current solutions before proposing yours.
3. Uncover a compelling event
“What’s causing you to take a serious look at solutions right now?”
⇢ They had a product launch next quarter. Timing is key!
↳ Find out what’s driving urgency.
4. Talk about possible solutions
Once I understood their needs:
“Here’s how I think I can help with [their challenge].”
⇢ Focus only on what matters to them.
↳ Align your solution with their actual needs.
5. Shared my personal cost
“Mind if I walk you through a range of what the cost might look like?”
⇢ Transparency is critical.
6. Acknowledge their efforts
“What have you tried to address these gaps?”
⇢ They’re getting the job done without you—understand how.
↳ Don’t show up blind—be informed.
7. Don‘t offer things right away
Instead, I asked:
“So, tell me more about your sales team. Where do you think they need to level up?”
⇢ Uncover the real challenges.
↳ Respect their time—be clear about expectations.
8. Know the business risks early
“You’ve got other co-founders and a Sales leader involved. What would stop them from moving forward?”
⇢ Better to uncover objections now than later.
↳ Address potential risks upfront.
↳ Make sure it’s a meaningful next step.
9. Open doors for locking in time
Rather than leaving it to chance, I said:
“Let’s lock in time for a follow-up with your co-founders.”
“What’s the best time for all of us?”
⇢ Always secure the next step before ending.
Smart discovery that earn better answers
Kyle Asay challenges outdated sales thinking with practical strategies rooted in real human behavior.
1. Ditch the shallow mindset
Stop asking questions you could’ve Googled.
⇢ “Where are you based?”
⇢ “How does your company make money?”
⇢ “Can you describe your day-to-day?”
↳ These signal you didn’t prepare—and kill trust early.
2. Carry a strong point of view
Not having a POV makes your discovery forgettable.
Instead, build your take using this 3-part framework:
• Company Objectives – What’s the org trying to achieve?
• Team Objectives – What’s the department focused on?
• Priorities – Leave this blank → fill it with customer input during the call.
↳ Even a wrong POV is better than none—it invites correction and creates momentum.
3. Do the work (before the call)
Use tools like ChatGPT or just their website/LinkedIn to prep.
⇢ Ask AI for key company/team goals using this prompt (screenshot it!)
⇢ Turn that into a one-slide POV to share early in the call
⇢ Use that POV to skip the fluff and get into real conversations fast
↳ Preparation = Permission to go deep.
4. Start with their own reason
Whether inbound or outbound, open strong:
• Inbound:
“What led to you reaching out to us?”
“What’s one thing you want to get out of today?”
• Outbound:
“What made you say yes to this meeting?”
“What’s one thing you want to walk away with?”
↳ Simple, clear, and makes them feel heard.
5. Validate your POV live
This step cuts 20 mins of surface-level conversation down to 5.
⇢ Share your slide:
“I did some research. Here’s what I came up with. What’d I get right or wrong?”
⇢ Let them add, correct, or rank priorities.
↳ Now you know what truly matters to them—from their mouth.
6. Ask on their current state
Once you know their top priority, the questions get sharper:
• “How are you trying to accomplish [insert priority]?”
• “What are your biggest challenges in getting there?”
• “What’s working and what’s not right now?”
↳ You’re not fishing for problems—you’re aligning on what’s worth solving.
7. Make it a conversation
Discovery shouldn't feel like a survey.
To keep it balanced:
⇢ Use customer stories:
“Another client of ours ran into that same thing…”
⇢ Use context bridges:
“The reason I ask is…”
→ Eases the pressure. Makes your question feel relevant, not random.
↳ This keeps the tone collaborative and builds trust.
Closing discovery starts with numbers
Marcus Chan reveals why most discovery calls fail and how to fix them.
1. Seek pain points first
Start with what hurts—because pain drives urgency.
⇢ Forget features, forget solutions.
⇢ Ask: “What’s keeping your team from hitting targets?”
↳ You’ll open a real conversation, not a script.
2. Go multiple levels deep
Don’t stop at surface-level answers.
⇢ Use:
• “Can you give me a specific example?”
• “How exactly did that affect your team?”
• “Tell me more about that…”
↳ Keep peeling the onion. That’s where the gold is.
3. Quantify everything
Vague = weak. Numbers = power.
⇢ “It’s frustrating” → no deal.
⇢ “We’re losing $250K a quarter” → game on.
↳ Their metrics make the pain real.
4. Trigger emotions
B2B is still human to human.
⇢ Ask:
• “How has this made you feel personally?”
• “What was your boss’s reaction when this happened?”
People buy with emotion, justify with logic.
5. Expand your impact
Make them confront the cost of doing nothing.
⇢ “What happens if this continues for another year?”
Their answer should scare them more than your pitch.
6. Multi-thread the pain
One person’s pain is good. Multiple people’s pain = movement.
⇢ Ask:
• “Who else is affected by this?”
• “How does this impact their goals?”
Now, it’s a team-wide issue—not just one department’s.
7. Don’t pitch instantly yet
Found serious pain? Don’t jump into solution mode.
⇢ Stay curious. Keep digging.
The more they feel understood, the less you’ll need to sell.
8. Use a deliberate sequence
Your questions should build tension, not wander aimlessly.
⇢ My go-to sequence:
• “How long has this been going on?”
• “What have you tried so far?”
• “Why didn’t that work?”
• “Which metric is suffering most?”
• “Where is it now vs. where it needs to be?”
• “How has this impacted you personally?”
• “Who else is feeling it?”
• “What happens if this goes on another year?”
TO-GO
Samantha McKenna: Improve your sales tactics now
Martin Roth: Win the close by owning the discovery
Brian LaManna: Your secret formula needed for calls
Mor Assouline: Asking the right questions every time
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Big Desk Energy: Startup stories and vibes
B2B Whales: Proven B2B sales strategies
The AI Report: Learn AI in 5 minutes a day
The Follow Up: We talk about Sales like your friend
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QUOTE OF THE DAY
"Start working with your prospects as if they’ve already hired you."
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