Hi Reader,

This week on the Gentle Power Podcast (GentlePowerPodcast.com), we sat down with Daniel Imberman, a friend from the Sandbox community who now runs his own consulting firm out of Mexico City.

Daniel spent years as an engineer. He was employee #10 at Astronomer, the company you might know from a certain Coldplay kiss cam moment, and he helped scale it from 10 to 300 people. He then left to build a business where he himself is the product.

Much of what we discussed revolved around how the frequency in which Daniel engages in negotiations drastically changed. As an employee of a company, you might negotiate once or twice a year, usually around a job change or a raise. As a self-employed consultant, Daniel negotiates every week now, and his last six months have been a crash course where he shared lessons learned that apply whether you’re pricing a project or asking for more at work.

Here are some good takeaways from our conversation, and links to our conversation with him here: YouTube | Spotify | Apple​

1. Negotiation is a muscle, and it atrophies.

Daniel mused how rarely most people actually negotiate. Every year or two, you push for a slightly bigger raise. Then maybe every three to five years a new job comes along, and the offer you sign sets your salary for the next few years. Outside those windows, you're barely negotiating at all, and this muscle naturally weakens.

His life looks nothing like that today. “I negotiate every week now,” Daniel told us. “It’s wild, the crash course in negotiation I’ve had to take in the last six months.”

You don't have to become an entrepreneur to know this. Negotiation rewards reps, and most employees barely get any. So when the comp conversation finally happens, one of the highest-stakes conversations of your career, you're usually walking in cold and out of practice.

Where can you build this muscle? We recommend a few things: try negotiating something small every day, almost as a social experiment. You’ll see how many times you actually get a yes. Or you’ll get comfortable with hearing no, so you’ll be less afraid to negotiate next time.

Alternatively, try to improve on something in every deal, conversation, or meeting at work, no matter how small, by learning what’s most important for the other party and exploring if you can make them and you better off. There’s a lot of hustle and creativity that goes into negotiations. You just need to take many shots on goal.

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2. Sell like a gardener, not a hunter.

We loved this quote that Daniel shared: “I’m a gardener, not a hunter.”

A hunter wants the kill: walk up, name the price, and close the deal. Daniel prefers gardening: planting a relationship and waiting for it to grow. As he put it, “Let’s establish a relationship. Let me understand your pain points. Let’s talk in a couple months when you really need me.”

He treats every new lead like something to nurture, on the understanding that some sprout on their own schedule. He’s found that the ones who say “not now” in January tend to come back in May.

We’ve seen this same pattern in our own business. Some of our clients first reach out months, sometimes years, before they decide to work with us, so the relationship was already established once the timing lined up.

3. “Too expensive” usually means “I don’t trust you yet.”

Interestingly, price is rarely the actual objection. Daniel said, “People will say it’s too expensive when what they really mean is, I don’t trust you.”

He used to take “too expensive” at face value and assume it was about the number he was charging for his service. Over time, he saw that price was not always the true blocker. If he told a brand-new prospect that he charges $50K for a promised $200K return in a month, they wouldn’t take him seriously since they had no reason to trust him yet.

Instead, show the other side you understand their pain and what a real solution looks like. “If you believe that I understand your pain and that I’m the person who can solve it, well then I’m not too expensive,” he said. “It’s just a matter of what ratio of that outcome you want to pay.”

This happens all the time in job negotiations too. Companies don’t quote you the top of their budget upfront. They haven’t been sold on your value yet, so your job is to make that value obvious well before you start discussing numbers.

4. Daniel’s hot take: the best negotiations are when both sides are sitting on the same side of the table.

“A lot of people have a fundamental misunderstanding of what negotiation is,” Daniel said. “They think of negotiation as you versus the person you’re negotiating with.”

If you assume that framing, you’ve turned the conversation into a confrontation, which means eventually butting heads. Daniel instead asks himself a different question to guide his negotiation strategy: what does each side actually want? Get clear on the shared goal first and the rest gets much easier.

This is also how we coach our clients. When a client drafts something like “Can you do this number?”, we have them reframe it to “Can the team…” rather than “Can you…” That small change in language changes the dynamic from “me versus you” to “the two of you versus the constraint”. The budget becomes the third stakeholder in the room, the thing you’re both working on together to solve.

When it comes to salary, remember that you and the hiring manager are usually on the same side. Interviewing is a slog for the company too, they chose you and made you and offer, and if the negotiation falls apart they’re back to booking hours of calls with other candidates. This far into the interview and offer process, nobody wants the deal to fail.

5. Tie your pay to the other side’s outcome.

Daniel hired a coach named Dan, partly to learn how a skilled salesperson sells. Dan’s offering was what convinced Daniel to hire him. “It charge this much, and you can book as many one-on-ones with me as you want until you’re happy.”

Daniel uses this same logic to structure his AI enablement work, keeping a Slack channel open so his clients can reach him whenever they need him. His pay rises and falls with their results.

Our pricing is similar. A big chunk of what we charge is a success fee, a percentage of the gap between your offer when we start and where it ends up. We mostly earn on the increase we actually help you win, so our incentives are aligned with yours.

6. When comp comes with milestones, take control of the conditions for hitting them.

Milestone-based pay came up in our conversation too, and we’re flagging this because we’re seeing more of it recently in client offers. We’re seeing really big comp packages even in this employer’s market, but sometimes a big portion of the comp (even in the seven-figures) is tied to hitting specific targets.

This looks great on paper, but the real question is whether you’ll actually hit those numbers. What if your hiring manager leaves six months into your role, leaving you to make your case to someone new who wasn’t there for any of it? At LinkedIn, Gerta had four managers in two years, a new one roughly every six months. This made it difficult and tiresome for her to advocate for herself anew with every leadership shuffle. Plenty of milestones stay fuzzy too, vague enough that meeting the bar often comes down to one person’s interpretation.

Daniel does plenty of milestone work himself, and he advised that if your pay hinges on a milestone, explicitly lock down what you need to reach it. For a freelance consultant, that might mean data access or a proper development environment. He boiled it down to: “How can I make sure that the company is as aligned as possible towards me reaching these milestones?”

If you don’t set the conditions for your own success, it may get too murky and you could be missing out on big payouts.

7. In an internal negotiation, the person who brings the receipts wins.

Early at Astronomer, a certain product Daniel worked on (we’ll call it “Alpha Feature” for confidentiality/privacy sake) was in rough shape. The CEO came from sales, sales looked strong, so from where he sat everything seemed fine.

But Daniel saw a problem brewing. People online were starting to call Alpha Feature a dying product, and Daniel was aware of how dangerous this was from a public opinion standpoint. “Memes are easy to squash in the beginning, but once a meme has set, it’s impossible to squash.”

He also knew that internally, a raw complaint from an engineer could get waved off as griping about hard work, so he came with evidence. He pulled together Reddit threads and Hacker News posts of people writing off Alpha Feature and brought all this to the CEO to show that this sentiment was spreading publicly.

Daniel's approach worked. The CEO was convinced, he directed more resources to rebuilding Alpha Feature, and Daniel was later awarded an equity refresh for this work. His team even took a competitor’s article titled “Why Not Alpha Feature” and turned it, point by point, into the Alpha Feature 2.0 roadmap. Daniel said, “If two people propose ideas and one person has receipts or a demo, that person is going to win.”

The same is true for any internal ask. Whether you want a raise, a promotion, more budget, or a change in direction, the person holding evidence is much harder to dismiss than the one arguing based on “vibes”.

Daniel’s career arc is a case study in controlling the things most employees leave on the table, from how often you negotiate to how your pay is built. Give this episode a listen if you’re weighing a move into starting something of your own, or if you just want to handle your next offer better.

The full episode here: YouTube | Spotify | Apple​

Learn more about Daniel’s consulting work at imberman.ai.

Warmly,

Gerta & Alex​
​Founders, YourNegotiations.com

P.S. Are you job searching or have upcoming negotiations?

If you have an offer coming or are mid-process, we’re always happy to help you think through how to approach it. Book a free call here: 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.