Crucial Business Deals: 18 Negotiation Tactics That Seal the Deal

Negotiation is a daily part of our job in M&A, but one experience that stands out involved a lower-middle-market company where the seller’s valuation expectations were far above what the financials supported. Instead of pushing back directly, we reframed the discussion around shared goals — speed, certainty, and legacy — then built a structure that met those priorities without overpaying. By introducing an earnout tied to post-close performance, we bridged the valuation gap and kept both sides aligned. The deal only came together because we shifted from positional bargaining to problem-solving.

The tactic that proved most invaluable was simple: separate what the other party wants from why they want it. Once you understand the underlying motivations — security, recognition, continuity, risk reduction — you can craft terms that satisfy their real needs without conceding on price or fundamentals. In M&A, that’s the difference between a stalled negotiation and a signed LOI.

One of the most important negotiations I’ve handled wasn’t actually about price — it was about risk. We were trying to move forward with a product line that had real potential, but the numbers only worked if our manufacturing partner was willing to take on some shared responsibility. They were hesitant, and understandably so.

What shifted the entire conversation was slowing down and asking real questions instead of trying to “sell” them on the idea. I wanted to understand what was actually stopping them, not what they were comfortable saying on the surface. It took a bit of patience, but eventually the real issue came out: they were worried about labor planning and sitting on unused inventory if our volumes didn’t hit right away.

Once that was clear, the negotiation got a lot easier. It wasn’t us on one side and them on the other — we were jointly solving the same problem. We built a structure that gave them predictable production windows and gave us the flexibility we needed as demand grew.

If I had to highlight one tactic that made the difference, it would be this: ask the kind of question that forces both sides to think together, not defend their position. Something as simple as, “What would make this work for you without putting you in a bad spot?” opens a door that hard bargaining never will.

That approach has stayed with me. Most people don’t resist the deal — they resist the uncertainty around it. Clear that up, and the negotiation becomes a conversation instead of a battle.

One notable thing that happened to me was when I was negotiating an Enterprise contract with a company who wanted our AI tools but insisted on excessive discounts. The deep discount would have looked great on paper but would have hurt us as a business over time.

So rather than talk about price, I changed the focus to value and risk, by getting the potential price associated to continue operating without the problem our system resolved (missed leads, manual hours, compliance exposure). After that number was presented, I noticed an immediate change to the conversation — it shifted from, “What’s the lowest we can get this for?” to “How quickly can we deploy?”

The key tactic that changed the entire conversation was silence. After presenting the value, I stopped talking. No longer justifying, filling the silence with additional information, or being nervous about making the deal, I sat in silence allowing them to “sit” with the reality that the price matched the impact.

They accepted the full price. They later told me how much they respected me standing my ground and not giving in or overselling. Sometimes the strongest thing you can say during a negotiation is nothing at all.

Pre-stating the other side’s arguments.

This might be the most counterintuitive trick of all in dealing with sellers that you either really want to sell to or are really sophisticated.

I’ve used it in several acquisitions. Basically what you do is start the conversation by saying everything the other side would say to justify the price or terms they’re seeking. For example, when I negotiated to buy a commercial portfolio, I started out by saying everything the seller could say to justify a premium price:

• “This portfolio has been a strong cash flow performer historically.”

• “It’s only going to become more valuable as these anchor tenants renew their leases.”

• “This is like buying a hot stock, because of all the development that’s planned in the area.”

Not only does this put you on the other side of the table, facing yourself, but it also has the effect of immediately disarming the other side. The first thing they say is, “Wow, you understand our position!” So they have less defensiveness and move right into a valuation discussion. One of these sellers actually said, “Well, that’s my whole pitch!” and then I pointed out that since I’d acknowledged that, we could start negotiating.

I can’t remember a deal where this tactic hasn’t worked. Negotiations usually go 30 to 50 percent faster, with less rounds of counteroffers, and you often end up paying 5 to 8 percent less. For tech founders and b2b founders, this same tactic will be even more effective at dealing with sellers who expect to play long games. Instead, they feel acknowledged and respected and are thus more likely to make concessions in order to get a deal done, rather than just feel that it’s a game of posturing.

If you’re negotiating acquisitions or partnerships, write out your counterpart’s best arguments for their case and read them out at the top of your conversation. You’ll skip fencefighting.

Early in my time at my business, I was negotiating terms with a major client in the cannabis industry. They wanted legal coverage across multiple jurisdictions for a fee that didn’t match the work involved. I went back and forth for weeks, adjusting timelines and scope to try to make it work. The turning point came when I stopped negotiating and clearly stated what I needed to deliver quality work: a specific fee structure and realistic deadlines. I was prepared to walk away. That shift, moving from accommodation to clarity about my boundaries, changed the entire conversation. They either accepted my terms or we didn’t work together. We worked together, but on terms that actually made sense for both of us.

What proved invaluable wasn’t aggressive posturing or clever wordplay; it was knowing my actual limits and being willing to step away from a bad deal. Most people negotiate because they fear missing out on the opportunity. But when you remove that fear by genuinely being okay with walking away, you negotiate from a position of strength. You stop scrambling and start communicating. Clients sense that. Decision-makers respect it. The best deals I’ve made happened when I was clear about what I wouldn’t compromise on and had the backbone to mean it.

One negotiation that really shaped my leadership was securing a long-term transportation partnership with a major event-management company in Los Angeles. They needed dependable, luxury-level service for high-volume events, but their budget expectations were far below what it would take to maintain our standards.

Instead of pushing back immediately, I used a tactic that has saved me many times: silent listening. I let them explain every concern, every fear, every number without interrupting. Once they were done, I walked them through how reliability, vehicle quality, and trained chauffeurs directly impact their client experience — and ultimately their brand.

That calm, patient approach shifted the conversation. They ended up expanding the scope and accepting a higher rate because they felt genuinely understood. Sometimes the strongest move in negotiation is simply listening long enough to see the real issue.

Yes, one moment stands out. I was negotiating a three-way agreement to co-implement a large, high-profile project. The challenge wasn’t just aligning deliverables. Both other parties had been burned in past collaborations, so they came in guarded and already anticipating failure.

I didn’t push for consensus. Instead, I tried to create room for people to voice their fears without the whole thing falling apart. I said the thing no one was saying. “It feels like everyone’s trying to be polite, but we aren’t there yet on trust — what would failure on this project look like for you?” The questions landed and we were able to start sharing what had destroyed partnerships in the past and see that we had perspectives in common.

I also did quiet work outside the room, reaching out to each party to understand what they were protecting, what they needed to feel safe re-engaging. That gave me a map of the unspoken dynamics and let me help rebalance things, even without formal authority. For deals that are meant to build long-term engagements, building the relationship is crucial to the outcome.

One of the most important negotiations I handled was with a retailer who wanted to purchase our ethnic wear collection but insisted on very low margins and extended credit terms. Instead of jumping directly into the price discussion I shifted the conversation toward their actual needs.

I walked them through actual sales patterns from other stores that we supply and showed how some salwar suit collections sell consistently month in and month out. Once they understood that reliable turnover reduces dead stock and improves profitability, they became much more flexible on both margins and payment terms.

The negotiation tactic that proved invaluable was this: Never negotiate only on price, negotiate on value and risk reduction. When the other party clearly sees how a deal helps them make more with less risk, they become much more open to agreement. This approach has helped me to secure several long-term wholesale partnerships.

For me, negotiation is one of the most important parts of real estate, and one experience that stands out is a deal I handled for a buyer who was competing against multiple offers. The home was in a highly desirable neighborhood in Southern California, and the seller already had strong offers on the table. My client loved the property but didn’t want to overstretch financially, so I had to find a way to make our offer stand out without simply raising the price.

This is where strategic negotiation matters more than anything. Instead of jumping straight to numbers, I focused on understanding the seller’s true priorities. Through conversations with the listing agent, I learned the sellers were relocating out of state and needed flexibility more than anything, specifically, extra time after closing. With that insight, I crafted an offer that gave them a comfortable rent-back period, clean contingencies, and a timeline that aligned with their move.

That negotiation tactic, identifying the real motivators behind the deal, proved invaluable. Most people assume negotiations are always about price, but I’ve learned that the strongest deals happen when you listen closely and position your offer to solve the other side’s problem.

The result? My client won the home without having to match the highest offer. The sellers were thrilled because the terms made their transition easier, and my client felt like they got a fair, strategic win.

This experience reinforced a key lesson: successful negotiation isn’t about pressuring or outbidding; it’s about uncovering what really matters to the other party and building a win-win structure around it. That approach has helped me secure better outcomes for my clients and build a strong reputation.

I had to negotiate a multi-year licensing deal with an edtech distributor wanting to white-label our flipbook engine for over 300 school districts. Their team pushed hard on volume-based pricing, but I knew the real leverage was support. I offered deeper integration and onboarding in exchange for less discounting on unit price. That reframed the conversation from pure cost to long-term stability.

The tactic that worked for me was anchoring around shared risk. I showed them a side-by-side comparison of projected support tickets with and without our onboarding, using real numbers from past rollouts. That grounded everything in operational impact instead of just arguing about margins.

Basically, when the other side sees you’re actively managing their future headaches, it changes the tone completely. They stopped pushing so hard on price because they realized cheap upfront could cost them way more in chaos later. We closed the deal at 92% of our original ask with a tighter relationship than if we’d just caved on pricing.

One strategy that has yielded one of the biggest returns for me is to avoid what I call “internal self-negotiation.” When I was negotiating pilot deals with our first enterprise customer or trying to figure out partnership terms with a major AI infrastructure company, I noticed I was sabotaging myself by internally deciding that the other side would never agree to certain terms.

“They wouldn’t accept that price,” “They’re probably restricted by a non-compete,” “They’ll never agree to that.” I was mentally ruling things out when I hadn’t even brought them up yet. An example may help. We nearly lost an important partnership last year due to internal self-negotiation. We were trying to establish a co-marketing relationship with a platform that was much bigger than us. My default tactic would have been to propose a very small co-marketing campaign. I was going to propose the smallest plan that seemed reasonable because I assumed they would reject anything more ambitious. Instead, following negotiation literature, I consciously decided to offer them the whole menu: various sizes of joint marketing campaigns, plus featuring on their front page. And because I wasn’t internally pre-filtering proposals, I ended up mentioning ideas that felt huge to me. And guess what? The biggest package didn’t scare them off. In fact, they were sitting on marketing budget they were burning to spend, and were looking for the riskiest new ideas. So we ended up with a deal 3x the scale of what I would have proposed.

Now, what does this mean for founders? The upshot is tactical: Don’t internally pre-negotiate or self-negotiate during conversations. Present possible options in the room. I’ve not only gotten better deals out of this, but it also makes the conversation more natural and collaborative. That’s because the other side feels like you’re searching for solutions together instead of throwing fixed offers back and forth.

There was a time when my team and I were working on a project with the client trying to cut costs, and my immediate response was not to argue over a number but to deal with the matter of value and options. So what I did was to present the proposal in three different groups — must-haves, nice-to-haves, and future upgrades — and ask the customer, “Which ones do you think are extremely important for you now?” Managed to transform the atmosphere: on one side, they got the feeling of being in power, on the other, we managed to keep our profits and still got them excited about what we had developed. My best practices are: establish your hardest deal-breaker in advance, let your questions be more than your talking be, and in case you offer a lower price, do it by means of scope and/or terms so that you are not simply losing money.