What Founders Ask (and What They Should Be Asking Instead)
- Raj Mahajan
- May 7
- 2 min read
Updated: May 8
When founders first start thinking about selling their business, one of the first questions I usually hear is:
“What would you pay for my business?”
It’s natural to start with price. But after buying, operating, and selling a software company myself, price is just one piece of a much bigger decision.
Here are the top 5 questions most sellers ask and what I believe they should really focus on instead.
1. “What would you pay for my business?”
Price matters, but it’s not the full story. Value also depends on:
What’s the deal structure?
Will I share in future upside?
What happens to my team and customers?
Value is more than the headline number, it’s about the details to get there.
2. “What happens to my team?”
For many founders, their team is the company.
When I look at a business, I’m not just buying software; I’m investing in the people behind it. A good buyer will value your people as a core part of the deal, not just as a cost center.
3. “What’s your experience?”
You want a buyer who’s been through the hard stuff, not just someone who talks about It.
The right buyer will have lived through mistakes, course corrections, and growth and will bring that experience to what happens next.
4. “Why now?”
Good buyers won’t pressure you with urgency tactics like “this market might disappear. A thoughtful buyer understands that selling is a big life decision and respects your timeline.
Selling should be driven by your goals, not anyone else’s urgency
5. “What will I do after I sell?”
This is one of the most overlooked questions.
Many founders focus on the transaction, but not on their life post-sale.
Without a clear role or next chapter, post-exit life can feel disorienting or unfulfilling.
The right deal should leave you energized for what’s next.
Better Questions to Ask:
Who is this buyer and how do they behave when things go sideways?
How do they make money, and does that align with your values?
Will my team and customers still thrive?
Do I have control over how I’m involved afterward?
Selling isn’t just about exiting; it’s about setting up the right future for yourself, your people, and your company.
I’ve sat in your seat. If you’re thinking about what’s next, I’d be happy to be a resource even if I’m not the right buyer for your business.