The most common question I get from aspiring entrepreneurs is: "How do you negotiate well?"

It's the right question to obsess over.

If every opening in business is a sale: recruiting, fundraising, pitching, then every close is a negotiation: hiring, investment, signed deals. And the biggest mistake I see most professionals make is chasing the wrong North Star.

Amateur negotiators care about winning. Defeating the other side. Coming out on top.

Expert negotiators know that "winning" is a fool's errand.

In negotiation, the goal is to first expand the pie to create maximum value, then capture as much of it as possible. The best deals don't feel like battles. They feel like construction projects.

So how do you do that?

My Negotiation Framework: The 3+3 Approach

The 3+3 has two components: Substance and Process.

Substance focuses on the core elements of a negotiation — price, terms, structure. Process covers everything else. Here's the counterintuitive part: most deals fall apart not because the substance was impossible to align on, but because the process was managed too casually.

I've used this framework to close M&A transactions, lock down strategic partnerships, secure executive talent, and find my way into oversubscribed fundraising rounds. It works in any high-stakes situation. Here's how it breaks down.

SUBSTANCE

I. Define the Outcome Spectrum

Before you walk into any negotiation, explicitly map three outcomes: (1) great, (2) acceptable, and (3) bad. Place them on a spectrum.

Then ask yourself: What are the probabilities of each outcome? What variables drive those probabilities? How interconnected are they?

Understanding your boundary conditions at the outset isn't pessimistic; it's essential. You can't navigate without a map.

II. Expand the Variable Set

Most negotiators fixate on price. That's a mistake. Terms and conditions are often more consequential.

Once you've clarified your own variables, flip the lens. What matters to the other party? Think beyond price: time, leverage, brand, access, coordination, reputation, risk. Don't assume your priorities mirror theirs — they rarely do. The negotiators who find creative deals are the ones who took the time to understand both sides of the table.

III. Break the Box

When negotiations stall, it's almost never because a term is truly unmovable. It's because both sides are arguing about the term itself rather than the conditions around it.

Reframe. Use guardrails like contingencies, performance parameters, and phased commitments to create alignment where none seemed possible. If you can't agree on a price, maybe you can agree on a price given certain conditions. Structure is your friend. Nearly anything can be structured.

PROCESS

I. Build the Relationship

Deals are negotiated by humans, not contracts. Trust is the foundation of any value-generating agreement.

Early in the process, invest in finding common ground. What are your shared interests? Mutual connections? Aligned priorities? The sooner both sides see each other as collaborators rather than adversaries, the more creative and durable the outcome will be. People make concessions for people they trust. They dig in against people they don't.

II. Communicate Appropriately

How do you prefer to communicate — text, email, phone, in person? More importantly, how does your counterpart?

It sounds like a minor detail. It isn't. Communication mismatches kill deals that had every reason to get done. At the outset of any meaningful negotiation, ask your counterpart directly how they'd like to stay in touch throughout the process. A simple question that prevents a lot of unnecessary friction.

III. Accelerate the Velocity

Time kills all deals.

Not because anything goes wrong, but because it increases the probability that external factors take over. Market shifts. Budget cycles. New priorities. Personnel changes. None of these have anything to do with the merits of your deal, but all of them can derail it.

Keep the momentum going. Set clear next steps after every conversation. Follow up promptly. Move the ball forward. A deal that drags is a deal at risk.

The Bottom Line:

Remember: negotiation isn't about winning. It's about building something bigger than either party could create alone.

It's always better to get a slice of a watermelon than to eat an entire grape.

Have you lost a negotiation because you came out too strong? What would you do differently? Hit reply - I read everything.

See you next Thursday!

— Ahmad