Cold email alone isn’t cutting it.
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Define “data-activated Salesforce” (and why it’s taking over outbound)
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OpenAI announced they plan to compete with LinkedIn.
In mid 2026, they will be launching an AI powered jobs platform.
Likely not the only industry / company they are coming for…
NEWS TO KNOW
📚 – Best Way to Close Out An Interview (new take)
📝 – What type of objection is it really?
💸 – What buyers remember after sales calls
BEST FROM LAST WEEK
Asking for hard things, in a soft way.
Krysten Conner had a LinkedIn post that stuck with me last week.
She’s a top enterprise seller and former rep at Salesforce, Outreach, and Tableau.
She talks about the art of asking hard questions, in a soft way.
Here are 5 of her favorite examples:
–> What kinds of things did you get hired to change or start? (For executive discovery meetings.)
–> Happy to answer … sounds like you have a specific reason for asking?
–> You just mentioned …. what’s causing that to be prioritized?
–> How widely felt is this pain across your whole organization? A few teams or all across the org?
–> How will others in your org feel about using something like ?
They’re effective because they dig deep while feeling collaborative rather than interrogative.
The pattern I notice is that each question:
- Uses curious, open language (“What kinds of things…” “How widely felt…”)
- Acknowledges what the prospect just shared (“You just mentioned…”)
- Focuses on organizational dynamics and real impact rather than just features
Here are some other hard questions that can be asked softly:
“What would stop a partnership?” Instead of “What are your concerns?” – this frames potential obstacles as conditions to understand rather than objections to overcome.
“Walk me through what happens if you do nothing here.” Rather than “What’s your pain point?” – this gets them to articulate the cost of inaction in their own words.
“Who else would need to feel good about this decision?” More collaborative than “Who are the decision makers?” – it acknowledges that buy-in often extends beyond formal authority.
The softness comes from positioning yourself as genuinely curious about their world rather than trying to qualify them or push toward a sale.
When prospects feel like you’re trying to understand their reality rather than change their mind, they tend to open up more.
