Ask for what you want. Most people will say no. A few will say yes.
The Power of Asking, Even When You Expect No
Why Asking Matters More Than You Think
Most entrepreneurs fail quietly—not because their ideas are bad, but because they don’t ask. They don’t ask for the sale. They don’t ask for help. They don’t ask for a seat at the table.
I’ve been in rooms where million-dollar deals hinged on one uncomfortable question. Sometimes it landed. Sometimes it didn’t. But when it worked, it was because someone took the shot.
Here’s the thing: rejection isn’t a risk—it’s the default. The “yes” is the exception. You have to get comfortable living in the world of “no” to ever find the “yes.”
The Math of Asking
In finance, I trust numbers more than pep talks. Let’s say you have a 10% success rate when asking for something—funding, a partnership, better terms. That means 9 out of 10 people will say no.
If you ask once a week, you might get one “yes” every two months. Ask five times a week, and you could get two “yeses” a month. Same batting average, different volume. The math rewards persistence.
In sales, this is obvious. In operations, marketing, or hiring? Less so. But the rule holds: the more you ask, the more you get.
Real Examples from the Field
The supplier discount that wasn’t “possible”
Years ago, we had a supplier who swore they couldn’t drop their price. I asked anyway. Got a polite no. A month later, I asked again—this time with a larger volume projection. They dropped 8% off the unit price. That 8% improved our margins for the year.
The investor who ghosted, then came back
An early-stage founder I know got brushed off by a VC. He followed up six months later with better traction numbers. The investor not only funded him but introduced him to two more backers. That happened because he asked twice, without burning the bridge.
The employee who wanted a leadership role
I once had a junior analyst tell me directly, “I want to lead the next project.” She wasn’t the most experienced, but her initiative got her the shot. She did well, and it fast-tracked her career. Nobody had ever asked me that before. Most wait to be noticed—they wait too long.
Why People Don’t Ask
Fear of rejection is obvious, but it’s not the only reason. Some people don’t want to “bother” others. Some assume the answer before they even speak. Others think their ask must be perfect before it’s worth making.
The truth? People are busy, not psychic. If you don’t voice your need, it doesn’t exist in their world. Your “bother” might actually be their next opportunity.
How to Ask Without Being Annoying
- Be clear. Don’t bury the request in ten paragraphs. State it early and plainly.
- Make it easy to say yes. Reduce the friction—simplify the decision.
- Give context. A little backstory helps them see why this matters.
- Know when to walk away. Not every “no” is worth pushing.
- Follow up—lightly. People forget. Remind them, don’t hound them.
The Mindset Shift
Think of asking as prospecting for gold. Most of what you pan will be sand. That’s normal. The gold doesn’t appear without moving a lot of dirt.
There’s also a strange side effect: the more you ask, the less rejection stings. You stop taking it personally. It becomes part of the process, not a verdict on your worth.
One of my favorite lines on this comes from Jia Jiang’s book Rejection Proof: “When you get rejected, you gain clarity, not shame.” It’s true. A “no” often tells you where the real opportunity isn’t—saving you time.
When Asking Backfires
Let’s be honest: there are bad asks. Ones made without doing your homework. Requests that are too big, too soon. These don’t just fail—they can damage trust. So, calibrate your timing and scale.
If you’ve built no relationship with someone, don’t open with a huge favor. Start smaller. Earn credibility before you make the heavier ask.
The Compounding Effect
Each “yes” you win compounds over time. The supplier discount you secure this year becomes your baseline next year. The investor who funds you once may back you again. The mentor who says yes to coffee might later say yes to a major introduction.
The habit of asking is really the habit of creating options. Without it, you’re stuck with whatever the market, your network, or sheer luck hands you.
Final Thought
I’ve been told “no” more times than I can count. I’ve also built a career on the few times someone said yes. Those moments didn’t happen because I waited for the perfect time—they happened because I asked when I had the chance.
If you’re an entrepreneur, here’s the simplest equation: No ask = no chance. Ask = some chance. And sometimes, that’s all you need.
Book Recommendation
Rejection Proof by Jia Jiang – A practical, personal take on turning “no” into a tool for growth.
What Do You Think?
When was the last time you asked for something big and got it? Would you have gotten it without asking?
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