What Engineers Taught Me About Selling
Recently, I was re-reading "How to Win Friends and Influence People." I may have read this book a decade ago when I first became a founder and found it great. This time while reading it, I pretty much questioned everything and found it confusing.
Why? I read this quote > "How can I make this person want to do it?" with a bunch of examples for salespeople. And it really baffled me. Isn't this what manipulation is like?
This reasoning came from when I started working closely with engineers in the last few years. People generally say selling to them is hard.I get it. All these techniques we're taught - "find their pain and press on it," "create urgency with fake deadlines," "always be closing," "don't take no for an answer" - are pretty much BS.
And it doesn't just apply to engineers - we're all humans. Why do we have to play games to get people to buy things? There must be better ways.
I'm writing this blog to share some things I've learned and as a reminder to myself.
Late Medieval. Source: Internet
The AHA moment
When I started giving demos for my product, I was on a call with an engineer. I launched into my usual pitch about how our platform would "revolutionize their workflow." He stopped me mid-sentence: "Look, I just need to know if this handles 10K concurrent requests with consistent latency." He'd already done his research. He knew what he needed. He didn't need me to create desire - he needed me to provide information.
But here's the thing about engineers - they're natural contrarians. Tell them something, and they'll argue with you even if they secretly agree. Most smart people are like this. So I learned to stop making statements and start asking questions. Let them tell you what's broken.
This applies to everyone, not just engineers. CFOs, lawyers, doctors - they all know their domains better than you do. Let them be the expert.
Respect their homework
By the time someone contacts you, they've probably researched for weeks. They've read reviews, compared features, maybe even tried your competitors. Most salespeople ignore this and start from the beginning.
Find out what they already know "What solutions have you already looked at? What did you think of them?"
Ask what's still unclear "What questions are still unresolved for you?"
Fill in the gaps Now you know exactly where you fit in their evaluation and what specific information they need. This will help you to have targeted discussions about their actual decision criteria.
Start with their constraints
You don't need to make people want your product. They already want solutions to their problems. Your job is to figure out if you can actually solve those problems within their specific constraints.
Understand what they're working with Every buyer has technical, financial, and timeline constraints. Start there. "Walk me through what needs to work for this to be successful."
Show how you fit (or don't) Don't lead with features. Show how you work within their limitations. "Based on what you've told me, here's how we handle your scaling requirements..."
Be honest about mismatches This is the hardest part, but it builds massive trust. "For that specific use case, honestly [competitor] might be better suited." People are so used to vendors claiming they're perfect for everyone that honesty stands out.
Build real credibility
Engineers trust other engineers. But the principle applies everywhere - experts trust other experts.
Bring the right person If you're selling to finance people, bring someone who understands their world. If you don't have that person, become that person - start reading books, watch videos, talk to people in that space.
Let them teach you "I'm curious about your approach to [technical thing]. How did you decide on that architecture?" Now you're learning their actual decision-making criteria.
Build on what they know They know their domain better than you ever will. Your job is to show how your solution fits into their existing knowledge, not educate them about their own problems.
Respect their timeline
"This offer expires Friday" is manipulation and I hate it, and everyone knows it.
Find out what's really driving them "What's driving the timeline for this decision?" Real urgency comes from budget cycles, implementation windows, compliance deadlines - not your quota.
Work with their reality If they're a startup, they might move fast. If they're enterprise, they might need quarterly approvals. That's the reality, Respect it.
Don't create fake pressure "This is an important decision. What timeline makes sense for you?" You might lose some deals to more aggressive salespeople, but the customers you get will be better.
When you're too busy to overthink
Sometimes you don't have time for elaborate approaches.
Here's my simple process when I'm stretched thin:
Ask one good question about their current situation. Listen to their actual answer (don't wait for your turn to talk). Respond with what you can and can't do for their specific situation. Let them decide if it's worth exploring further.
Works surprisingly often.
The bigger truth
People still buy from people. And they want to buy from people they trust, not from people who try to manipulate them.
Look, maybe I'm wrong about some of this. Maybe there are situations where these "traditional" sales tactics actually work better. If you think I'm being naive or missing something important, I'd genuinely love to hear from you.
Or if you've tried any of these approaches and they backfired spectacularly, please tell me that story too. Let me know what you think on my email.
Note: Written from my own experience, with Claude helping me structure my rambling thoughts into something readable