Sometimes asking for more gets you less
The uncomfortable truth about negotiation, and what to do about it
Hi there, my friend.
You’ve probably heard this advice before: Just ask. Negotiate everything. The worst that can happen is they say no.
Ask, Save, Earn readers know that I’ve said versions of that myself over the years. To be clear, I still believe that asking questions and advocating for yourself is one of the most powerful ways to pay less, earn more, and keep more of your hard-earned money.
However, the unfortunate truth is that “the worst that can happen is that they say no” isn’t always true. We don’t talk about that enough, and that needs to change.
In writing my book, I spoke about this with Stefanie O’Connell, author of “The Ambition Penalty: How Corporate Culture Tells Women To Step Up And Then Pushes Them Down.” (Preorder it now here!) She has spent years studying how people actually experience negotiation, especially when it comes to jobs, raises, and promotions, and one thing she told me really stuck:
“Everything people hear is that the worst they can say is no… but what I kept seeing was that there actually is downside risk.”
That’s a pretty big shift from the conventional wisdom, but it is incredibly important to recognize.
Understanding the risk
In real life, asking for more doesn’t always just get you a polite “no.” Sometimes, it gets you less. As O’Connell told me, people get labeled as difficult. They’re seen as too aggressive or pushy. In some cases, they miss out on opportunities they might have gotten if they’d stayed quiet.
That’s uncomfortable to hear. It runs counter to a lot of what we’ve been taught about negotiation. However, ignoring that reality doesn’t help anyone. We have to understand it to deal with it.
What makes this even more important is what happens next. O’Connell said that when people have one of these experiences, they don’t usually chalk it up to a flawed system or a bad environment. They internalize it.
“People think it is something wrong with them,” O’Connell said. “and that sticks with them for the rest of their careers.”
That’s the real cost. It is not just the missed raise or the lost opportunity. It is the hesitation that shows up the next time they should speak up and don’t.
So does that mean you should stop negotiating?
Of course not.
You should absolutely ask for more. You should question charges, negotiate bills, and advocate for yourself in your career. That never changes.
What should change, however, is how you think about risk, O’Connell said.
The people who benefit the most from asking aren’t just the ones who ask the most. They’re the ones who can afford the answer.
That’s a big distinction, and it leads to a smarter way of thinking about negotiation.
3 things to remember before you negotiate
First, lower the stakes before you ask. When everything is riding on a single outcome, every conversation feels high-pressure and high-risk. One job offer. One promotion. One client. If that’s your situation, even a small downside can hit hard.
When you have options, the entire dynamic shifts.
“If you have multiple opportunities… it lowers the stakes when things go awry,” O’Connell said.
This is why it pays to keep your LinkedIn updated, to have conversations even when you’re not desperate, and to stay open to new opportunities. It is not because you’re looking to jump ship tomorrow, but because having alternatives gives you leverage. It lets you ask without feeling like everything is on the line.
Second, pick your battles. Not every negotiation deserves the same level of effort or intensity, O’Connell said. Sometimes it makes perfect sense to push. Other times, it doesn’t.
If you’re dealing with a credit card company, a bank, or your cable provider, go ahead and ask. Those are the kinds of places where a simple question can save you real money.
“A big telecom company doesn’t need more of my money,” she said.
But if you’re dealing with a small business owner or someone providing a service where margins are tight, you might make a different choice. That’s not about being soft. It’s about being intentional. It’s about understanding when negotiating serves you and when it’s just about winning for the sake of winning.
Finally, and maybe most importantly, know the environment you’re in. Not every company, manager, or situation responds the same way to negotiation. Some places reward it, some tolerate it, and some quietly punish it.
You won’t always know which is which upfront, but there are clues if you’re paying attention, O’Connell said. Who gets promoted? Who’s in leadership? Do people like you advance there? Those signals can tell you a lot about how your ask is likely to be received.
Risk doesn’t mean that the ask isn’t worth it
At the end of the day, this article isn’t meant to scare you away from asking for more. It’s meant to help you do it more effectively.
You should absolutely ask questions. You should push for better deals and better opportunities. That’s how you save money and earn more over time.
Just don’t rely on the idea that there’s no downside. The unfortunate truth is that sometimes there is.
The goal isn’t just to ask. It is to ask in a way that protects you. You do that by building options, lowering your risk and picking your spots.
Now go out there and get what you deserve.
Until next time!
Matt