As an M&A lawyer, I saw this play out daily. Companies often deploy their lawyers as the "attack dogs" in negotiations, taking hard positions while protecting client relationships. The lawyers hash it out, the clients stay friends, and everyone goes home happy.

But stepping into the startup world (I left my job as an M&A lawyer to join what was at the time a small legal technology startup as their Chief Revenue Officer) stripped away this luxury. Suddenly, I couldn't be the buffer anymore – I had to build lasting relationships while still getting deals done. This transition taught me something valuable: the principles of interest-based negotiation I learned in law school matter even more when you can't hide behind legal intermediaries. And so I wanted to share how these principles, anchored in the practice of law, can transform your approach to enterprise sales.

From legal shield to deal closer – learning to operate without a buffer

In M&A deals, lawyers often reduce negotiations to a zero-sum game – winning points against the other side by getting them to concede contract terms. It works because lawyers can take aggressive positions without damaging the underlying business relationships. The clients can always maintain plausible deniability.

But in B2B SaaS, where customer value accrues over 2-5 years or more, that adversarial approach is poison. You need to build trust and show empathy from day one. This means completely reframing how you approach negotiations – moving from winning positions to understanding interests.

Beyond "it's too expensive": the real stories behind deal-blocking positions

When I was drafting M&A agreements, we'd often get stuck on specific terms because both sides were taking hard positions without revealing their underlying concerns. Now, when a potential customer says "that's too expensive" or "we're not sure about the ROI," I know from my legal training not to take these statements at face value.

These are positions, not interests. The real story usually lies in organisational dynamics – maybe budgets were set six months ago, maybe your contact is worried about their reputation if they have to ask their CFO for more money, maybe they've been burned by vendors before. Just like in complex legal negotiations, you need to understand the constraints and pressures shaping the other side's position. So ask the questions that lead you there.

The art of strategic discovery – asking better questions

I have spent many hours of my legal career in discovery trying to understand the full context of a dispute. In tech sales, you need to do the same through strategic questioning. My favourite opener is simple: "Have you ever introduced software into this company before?" This immediately tells me whether someone needs hand-holding through internal processes or is ready for a more direct approach.

Other questions I've found invaluable to reveal real interests from buyers:

• "Can you explain how you arrived at that number?" (Understanding their logic rather than challenging it)
• "What questions will your CFO ask about this?" (Surfacing internal hurdles)
• "When does your budget renew?" (Finding timing flexibility)
• "What would make you look like a hero internally?" (Identifying personal motivations)

These questions help reduce information asymmetry –  the imbalance of knowledge between parties that often derails negotiations – and show you're interested in solving problems together rather than just pushing your position.

Due diligence 2.0: how modern tools are changing information asymmetry

Speaking of information asymmetry – it has traditionally defined negotiations. In law, we spent countless hours on due diligence to understand the other side's position. Usually, one party knows their constraints and pressure points while the other operates partially blind. Modern tools might be changing this dynamic.

Today, AI can analyse earnings calls, conference presentations, and annual reports to give us this context before conversations even begin. While this doesn't replace human interaction (people still buy from people), it helps both sides start from a more informed position – much like good legal due diligence did in M&A deals.

Building solutions, not taking positions

The most successful M&A negotiations happened when lawyers moved beyond fighting over contract terms to understanding what each party really needs to achieve. The same principle applies in tech. Once you understand the real interests at play, creative solutions emerge naturally - for instance, splitting payments across fiscal years, tying payments to success metrics, or structuring proof-of-value periods.

Most people you're negotiating with aren't trying to be difficult – they're operating within constraints, just like parties in legal negotiations. The key is separating the people from the problem and working together to find solutions that address underlying interests.

The new negotiation playbook

For tech founders and sales leaders coming from technical or product backgrounds, it's natural to focus on your solution's value and wonder why everyone doesn't immediately see it. But my legal background taught me that successful negotiations rarely hinge on the actual product or price – they're about understanding and addressing the human and organisational dynamics at play.

When someone brings untested technology into a large organisation, they're staking their reputation on it. Understanding these personal risks and organisational constraints is the difference between closing deals and wondering why great technology isn't selling.

Every position hides an interest, every stance masks a concern, and every "no" contains the seed of a possible "yes" – if you're willing to dig deeper. Master this understanding, and you'll build the kind of lasting relationships that drive real growth.

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