Hi Reader,
We recently had Pri Upadhyay, the talented product management coach behind "Product with Pri", on the Gentle Power Podcast (YouTube | Spotify | Apple). Pri spent 18 years in tech, including time at Google and Salesforce, then built a coaching and training business for product managers, helping senior PMs, directors, and VPs navigate job searches and transitions.
Pri is a career coach who's come to believe negotiation is one of the most underrated skills in her field. Her clients often don't even use the negotiation support that comes with her program.
We covered the psychology of leverage, the mindset traps that silently tank offers, and two personal stories (a grade negotiation at Columbia and a divorce mediation) that both leveraged the same principle: you have more power than you think, even when everything says you don't.
1. Negotiation is underrated, and most people prove it by ignoring it
Pri's clients often come to her exhausted after months of a brutal job market. They've finally landed an offer, and the last thing they want to do is risk it by negotiating.
Pri observed that people don't just fear rejection, but actually don't believe negotiation is worth learning. It's a skill they've categorized as advanced, optional, or only for people in a strong position.
"Even if you can get just $10,000 more, the bare minimum, why would you leave that money on the table?" she said. We hear this from our own clients too. The fear of losing the offer usually far outweighs the actual risk of asking for more.
For what it's worth: we've helped hundreds of people negotiate offers. We've never seen someone lose an offer from negotiating. How you ask matters, of course (a cordial, well-timed, strategically framed ask is very different from a poorly handled one), but the fear of asking itself is almost always bigger than the actual downside.
2. The "beggars can't be choosers" trap
After months of searching with few interviews, candidates start to internalize a story: "I should be grateful for whatever I get."
Pri sees this pattern clearly in her product management clients. They'll say things like, "I've been a principal PM for five years, but I'm happy to take a senior PM role." Maybe that's intentional, and if it is, fine. But often it's just exhaustion wearing the costume of flexibility.
"If you go into the job market seeing yourself as a beggar, others will see you that way too," she said.
We think about this a lot in our own work. The norms of the job search have largely been written by employers. When a company asks for your preferred salary on an application, that's not a neutral question. It's a move designed to reduce their own workload. Candidates tend to comply because the norm feels inevitable, but it isn't.
3. The company isn't optimizing for the cheapest hire
One of the things candidates get backwards: they assume that if they ask for less, they'll be more attractive.
But companies trying to fill the right role aren't choosing whoever will accept the lowest number. They're looking for fit. "They're not optimizing for whoever will take the least amount of money," Pri said. This is especially true at the senior PM to director levels she works with.
We'd go further: asking for what you're worth, clearly and professionally, often signals something good. It shows that you know your value, that you've done your research, and that you communicate directly.
4. Information gathering is most of the negotiation
A lot of people think negotiation is the moment you make an ask or push back on an offer.
But the conversation around what the company actually needs (why they're hiring, what their urgency is, what matters most to them) is where the real leverage comes from. If a company needs to close this role in the next month because of a product launch or an investor deadline, that changes what you can ask for and how you should frame it.
"Crossing the river to the other side," as Pri described it, i.e. understanding your counterpart's goals before you make any ask, is the move most candidates skip entirely.
In compensation negotiations specifically, the back-and-forth over numbers isn't where you win or lose. It's the information that comes before it that will set you up for success.
5. Negotiate your grade. Then your divorce.
Pri shared two personal stories around negotiations:
First, as a 24-year-old international student at Columbia, she received a grade she disagreed with from an adjunct professor. She ended up negotiating the whole thing over email, carefully mapping out how the grade had been distributed and making the case that one component was being overweighted relative to what was originally stated.
Second, when navigating her divorce, she found a mediator rather than going straight to court, partly to protect her energy but also because litigation felt like giving away something beyond money. She chose a male mediator intentionally, based on advice she received about her specific situation.
"I didn't want to give away my power like a lot of women do in divorce," Pri said. "Just take all the money, just sign the papers. I'm like, no. Negotiate."
The thread connecting both stories: she had less institutional power in each situation - as a student, an immigrant, and a woman navigating divorce. And in all cases, she found leverage anyway.
7. Know what you're actually negotiating for
Pri's third hot take was the most personal: get clear on what matters to you before you start.
For one client, the most important thing wasn't base salary, it was flexibility.
Different people at different stages of their careers are negotiating for different things: income, impact, speed, flexibility. The negotiation strategy follows from knowing which one matters most.
That's where the work actually starts.
Listen to the full episode here: YouTube | Spotify | Apple
Learn more about Pri's work here:
Best,
Gerta & Alex
Founders, YourNegotiations.com
P.S. Are you job searching or have upcoming negotiations?
Book a free call with us, where we’ll learn more about your situation, offer some free tips, and explore if we’re a good fit to work together: https://calendly.com/alexhapki/call
P.P.S. Know someone interested in negotiations?
Send them our way and we’ll thank you with $250 for each person who becomes a client. No cap.
A quick intro or an email to alex@yournegotiations.com works.