Databricks is raising over $4 Billion in Series L funding.
NEWS TO KNOW
Their numbers are staggering – $4.8B ARR, 55% YoY growth, and 140% NRR.
Can’t wait to hear about their Series W round.
📚 – 7 Observations from a VP of Sales
BEST FROM LAST WEEK
📝 – Hot take: Perfect length for cold calls
💸 – The hold technique – favorite tactic on demos
The Best Sellers Don’t Persuade.
Here’s something most reps get backwards: they think their job is to convince their prospect to buy.
It’s not.
Your job is to change how someone sees their world, not to change what they do about it.
When you try to persuade, you’re pushing.
When you push, buyers get defensive. Especially since it’s coming from a salesperson.
When you reposition, you’re guiding someone to a new vantage point where the decision becomes obvious. The conclusion feels like theirs because, well, it is.
The difference? Questions, not statements.
Bad selling sounds like: “You need our solution because X, Y, and Z.”
Good selling sounds like: “Walk me through how you’re thinking about this problem.”
The first creates resistance.
The second creates reflection.
A Real Example: The Sales Methodology Conversation
Let’s say you’re selling to a VP of Sales who’s rolling out a new methodology across their team.
After learning this, most reps would jump straight to: “Our platform helps with methodology adoption and gives you visibility into execution. Without it, you’ll have no way to measure if your team adopts this, let alone it actually works.”
That’s persuasion.
Here’s repositioning:
You: “So you’re rolling out MEDDICC across the team. That’s great. Walk me through your rollout plan.”
Them: “We’re doing training over two weeks, then having managers coach to it in deal reviews.”
You: “Got it. And how are you planning to measure whether it’s actually sticking? Like, three months from now, how will you know if reps are really using it in the field vs. just in internal meetings?”
Them: “Uh, good question. Probably through manager observation and pipeline reviews?”
You: “Sure. And when you do those pipeline reviews, what’s your current process for knowing whether a rep actually asked the economic buyer questions versus just filled out the field in Salesforce after the fact?”
Them: “Well… we kind of have to trust what they’re putting in the CRM.”
You: “Right. So if I’m hearing you correctly, you’re investing millions in this whole methodology rollout, but you don’t really have a way to verify if reps are doing it in real conversations or just checking boxes. Does that feel like a gap at all?”
Them: “Yeah, actually. That’s a real problem.”
You: “And when you think about ROI on this training investment, if you can’t see whether it’s changing actual buyer conversations, how do you tie it back to deals won or lost?”
Them: “I mean, we can’t really. We’d just be hoping it works.”
See what happened there? You didn’t pitch anything.
You asked questions that exposed a gap between their plan and reality. Now they’re feeling the problem viscerally.
They’re arriving at the conclusion that they need visibility into actual conversations, not because you told them, but because they reasoned their way there.
The Trap: Don’t Get Happy Ears
Here’s where 90% of reps blow it.
The prospect says “Yeah, that’s a real problem” and immediately the rep thinks “Great! Time to show them how we solve it!”
Wrong.
That’s happy ears. You heard pain and got excited.
But you don’t have the full picture yet.
If you jump in now with “Well, that’s exactly what we do!” you’ve just derailed the entire repositioning.
Why? Because you haven’t gone deep enough. You found a pain point, not the pain point.
You don’t know how big it is, who else feels it, what they’ve tried, or what happens if they don’t fix it.
So you stay in the pain funnel. You go deeper.
You: “Talk me through what happened the last time you rolled out a methodology or major sales initiative. How’d that go?”
Them: “Honestly? We spent $200K on training and six months later maybe 30% of reps were actually using it.”
You: “Damn. What do you think caused that?”
Them: “Partly manager bandwidth. Partly reps just reverting to what’s comfortable. We had no real way to reinforce it.”
You: “So you lost the investment and didn’t see the behavior change. What did that cost you? Like, if those reps had actually adopted it, what would’ve been different?”
Them: “Probably 10-15% higher win rates on enterprise deals. Maybe $3-4M in revenue we left on the table.”
You: “And this time around with MEDDICC, what’s your plan to make sure that doesn’t happen again?”
Them: “Well… I mean, we’re hoping managers will be more on top of it. But honestly, I don’t know how we prevent the same thing.”
NOW you have the full picture.
Not just the surface problem (“we can’t measure adoption”) but the deeper pain (“we’ve failed at this before, lost millions, and we’re about to do it again with no real plan”).
The key: You didn’t connect any dots for them yet.
You didn’t say “We can help with that.”
You just kept asking questions until they fully articulated the problem and its consequences.
The pain is now real, specific, and expensive in their mind.
Only after you have the complete view do you connect it back.
Their idea > Your idea
When someone reaches a conclusion on their own, they feel true ownership of it.
Their brain doesn’t trigger the same resistance because you didn’t activate their “someone is trying to sell me something” defenses.
Plus, their idea always beats your idea. Even if you guide them there. Especially if you guide them there.
The methodology prospect above will now go into your demo thinking “I need to see how this shows me real conversation adoption” rather than “Let me poke holes in why this won’t work.”
You’ve repositioned what matters to them.
The Bottom Line
Stop trying to convince people your solution is great.
Start helping them see that their current approach has a gap.
The best sales conversations don’t feel like sales conversations.
They feel like really good strategic discussions where someone asks questions you should’ve been asking yourself.
And yeah, maybe at the end of that conversation, they realize your product is the answer. But it’ll be their idea, not yours.
Win the week!!!
