Negotiating Offers
Offer negotiation isn't adversarial—it's a conversation about mutual value. The best negotiations happen after you've established your commitment to the role and demonstrated what you'll deliver. Most people leave money on the table because they never ask. The data is clear: 87% of the time, when you ask for more money, you get it.
The Guide
4 key steps synthesized from 3 experts.
Negotiate for success conditions before compensation
Before discussing salary, negotiate for the resources and authority you need to actually succeed in the role. Identify blockers during the interview process—tech debt, headcount gaps, budget constraints—and ask for commitments to address them as part of your offer. 'I'm excited about this role. Before we talk about money, let's align on what will set me up to hit the OKRs we discussed.'
Featured guest perspectives
"I want you to go and talk to the hiring manager... I want you to say, 'This is great. I want to talk about money, but before we do, I want to think about some of the things that will set me up to see succeed in this role. I think there's like $10 million of tech debt here. Does that sound right to you? And are we on board that that'll be priority one to eliminate the first day I start the job?'"— Phyl Terry
Use collaborative language when asking for more
Frame your ask as a collaborative conversation, not a demand. Use phrases like 'Are you open to...?' or 'Is that something we can talk about?' This lowers the perceived risk and keeps the negotiation constructive. Conduct the conversation live (phone or in-person) when possible so you can read reactions and adjust.
Featured guest perspectives
"87% of the time, Lenny, when you ask for more money, you get it... I want you to say, 'Hey, are you open to 450? That was really what I was hoping for. What I think I'm worth, are you open to that? Is that something we can talk about?'"— Phyl Terry
Understand what you're actually optimizing for
Compensation is often a surrogate for other needs—respect, learning, autonomy, title. Be honest with yourself about what actually matters. Sometimes a lower-paying role with exceptional learning opportunities or a great mentor is worth more than a higher salary at a company where you'll plateau. Know your trade-offs.
Featured guest perspectives
"I can actually pay people less if I give them better experiences... I pay them fairly well, but I know they can make more money elsewhere. And ultimately I want them to be attracted to go. So if they need more money, they should go somewhere else. But if they're here to learn, that's what I want people who are here to learn."— Bob Moesta
Consider non-traditional arrangements
Don't assume the offer structure is fixed. If you need flexibility, propose alternatives: contract work, reduced hours, or a transition period. Many employers are more open to creative arrangements than you'd expect. You might turn your current full-time role into a 3-day contract while you explore other opportunities.
Featured guest perspectives
"A big move that a lot of people do is turn their current job into a contract job, which a lot of employers are a lot more open than people would think... You say, 'Hey, I want to work three days a week. I want to be a contractor. Here's exactly what I want to do. Are you open to this?'"— Paul Millerd
Common Mistakes
- Negotiating compensation before establishing your value and commitment to the role
- Never asking at all—most people leave money on the table out of discomfort
- Making it adversarial rather than collaborative
- Focusing only on base salary and ignoring equity, signing bonus, or role scope
Signs You're Doing It Well
- The hiring manager stays engaged and collaborative throughout the conversation
- You've secured commitments on the resources you need to succeed, not just your compensation
- You feel confident that the package reflects your value
- The negotiation strengthens rather than strains the relationship with your future employer
All Guest Perspectives
Deep dive into what all 3 guests shared about negotiating offers.
Bob Moesta
"I can actually pay people less if I give them better experiences... I pay them fairly well, but I know they can make more money elsewhere. And ultimately I want them to be attracted to go. So if they need more money, they should go somewhere else. But if they're here to learn, that's what I want people who are here to learn."
- Identify if a candidate is prioritizing 'features' (salary/title) or 'experiences' (learning/autonomy).
- Be transparent about trade-offs, such as lower base pay in exchange for high-growth learning opportunities or mentorship.
Paul Millerd
"A big move that a lot of people do is turn their current job into a contract job, which a lot of employers are a lot more open than people would think... You say, 'Hey, I want to work three days a week. I want to be a contractor. Here's exactly what I want to do. Are you open to this?'"
- Propose a specific 3-day-a-week contract structure to your current employer
- Highlight the reduced risk for the employer (ease of firing) as a benefit of the contract arrangement
Phyl Terry
"I want you to go and talk to the hiring manager... I want you to say, 'This is great. I want to talk about money, but before we do, I want to think about some of the things that will set me up to see succeed in this role. I think there's like $10 million of tech debt here. Does that sound right to you? And are we on board that that'll be priority one to eliminate the first day I start the job?'"
- Identify critical blockers (e.g., tech debt, team training, headcount) during the interview.
- Ask for specific budgets or authority to fix these blockers as part of the offer negotiation.
- Frame these requests as necessary to achieve the agreed-upon OKRs.
"87% of the time, Lenny, when you ask for more money, you get it... I want you to say, 'Hey, are you open to 450? That was really what I was hoping for. What I think I'm worth, are you open to that? Is that something we can talk about?'"
- Conduct the negotiation live (phone or in-person) with the hiring manager if possible.
- Use the phrase 'Are you open to...?' to lower risk and keep the conversation collaborative.
- Establish your 'job mission' and value first to make the salary request a natural follow-up.
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