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The Art of Negotiating Equity: Lessons That Redefined My Leadership Journey
- Mark Evans MBA, CMgr FCMi
- Apr 14
- 5 min read
Updated: Apr 15
When I was 26, I thought I was nailing it, i started my first business at 9 and sold it at 11 and here was my next big deal.
I’d just secured pre-seed capital from a single Angel Investor, a well respected serial entrepreneur. Contracts were drawn up. Lawyers were involved. It felt official—like I’d made it.
But I was swept up in the excitement of the moment. The dream of turning a derelict Sealife centre on a Scottish beach into a unique entertainment venue, which I had nurtured for so long, was finally in motion, and I was filled with an overwhelming sense of urgency and anticipation to start this new chapter of my journey. I could hardly contain my enthusiasm and envisioned all the possibilities that lay ahead, the milestones I would reach, and the impact I could make.
However, in my eagerness, I failed to pause and negotiate the business terms that mattered most, such as critical elements like control over the direction of the project, the potential for dilution of my ownership stake, and the implications of voting rights that would affect my decision-making power in the future. Instead of taking the time to carefully consider these factors, it became a frantic race to sign the documents, an impulse driven by the thrill of opportunity.
I allowed myself to be caught up in the momentum of the moment, neglecting the necessary space for reflection and thoughtful deliberation that could have safeguarded my interests. The excitement was intoxicating, but it also clouded my judgment, leading me to overlook the foundational aspects that would ultimately shape the trajectory of my venture.
Four years later, I walked away broke, with worthless shares and no say.
That deal changed everything. It shaped the resilient leader I became, the mentor I am today, and the negotiator I’ve had to be across three decades of global business.
This article is my hand to hand playbook - built from ‘in the trench’ experience, tested under pressure, and designed for founders, executives, and emerging leaders navigating high-stakes conversations where equity, trust, and legacy are on the table.
Start With Tactical Empathy - Not a Pitch
Real leadership starts by listening, not performing. The most powerful way to lead a negotiation and more so negotiating equity isn’t through a PowerPoint - it’s through presence.
Before you sell your vision, show them you understand theirs:
“It seems like you’ve been through tough deals before.”
“It sounds like you want strategic influence without operational drag.”
When people feel understood, their guard comes down. That’s where real influence begins.
Use Calibrated Questions to Reveal Hidden Motivations
The best mentors don’t give answers - they ask the right questions.
In any negotiation, your job is to surface what’s not being said. Get beyond the valuation discussion and into what truly matters:
“What does a win look like for you here?”
“How does this investment fit your longer-term play?”
“What are you hoping to avoid?”
Calibrated questions like these slow the tempo. They force reflection. And they create space for shared understanding.
Conduct an Accusation Audit Before They Do
Leadership isn’t about avoiding conflict - it’s about heading it off with honesty.
Before they challenge your numbers, your intent, or your strategy, raise it yourself:
“You might be wondering if I’m overvaluing the business.”
“You may think I’m looking for fast money rather than a real partner.”
This earns trust immediately. It says, “I’m aware. I’m not naive. Let’s put the real issues on the table.”
‘No’ Is Where the Real Negotiation Begins
You’ve been taught to get to ‘yes.’ But experienced deal-makers know that ‘no’ is the turning point.
It gives the other party power - and once they feel safe, they tell you what they actually want.
Try this:
“Would it be out of the question to offer you board oversight without operational control?”
“Is it crazy to cap voting rights but maximise exit upside?”
They say “no,” and then… they talk. That’s when clarity shows up.
Stop Lizard Listening - Start Strategic Listening
At 26, I was deep in lizard listening - that primal mode where you’re not really listening at all. You’re just waiting to speak. To defend. To win.
Every conversation with my investor blurred into pitch-and-deflect. I missed tone. I missed subtext. I missed the chance to protect myself.
Strategic listening changed everything.
Here’s how I do it now:
Mirror their last few words: “Control dilution?”
Label the emotion: “It seems like that experience left you cautious.”
Pause. Let silence pull truth to the surface.
This is where real negotiation begins: not in the argument, but in the insight.
Always Look for the Black Swan
Every negotiation has a hidden variable - a pressure point, a personal driver, a strategic move you’re not yet seeing.
While negotiating with a prospective overseas distributor for a newly patented technology my company had launched, the party seemed credible. They signed NDAs and submitted a persuasive proposal, suggesting a real opportunity. However, after several meetings, it became evident that their main focus was on eliminating restrictive clauses concerning our intellectual property protection. Their ulterior motive was to obtain a demo unit for reverse-engineering a similar product circumventing any existing patents, which was quite underhanded!
You only uncover the Black Swan by staying curious and emotionally present. It’s not about paranoia, it’s about professional alertness.
Ask:
“What happens if this deal doesn’t go ahead?”
“What’s at stake for you personally?”
“How do you see this evolving in the next 12 months?”
These are the questions that can reveal the truth behind the posture.
Because the most dangerous move in any deal is the one you never see coming.
Define Your Red Line - and Be Ready to Walk
Years later, I was negotiating an exit with a global media player. On paper, they were perfect. But behind the scenes? Aggressive. Controlling. Bully-boy corporate tactics.
I had a red line: no surrender of IP, no handover of product roadmap in Year 1.
They pushed hard. Told me the deal would vanish.
So I walked first.
Two weeks later, they came back, with better terms and a different attitude.
Your red line is your identity. If you’re not ready to walk, you’ve already given away too much.
Final Word: You’re Not Just Negotiating Equity - You’re Shaping Your Legacy
Leadership is often measured in decisions we make under pressure. In negotiation, those moments define your credibility, your confidence, and your capacity to protect what matters most.
I use this playbook every time:
When advising founders
When selling a business
When entering new deals
When Investing
When entering new markets
Even when buying a car!
It’s not about tricks. It’s about clarity, courage, and the ability to sit with discomfort.
Because in the end, negotiation isn’t about control - it’s about alignment. And no deal is worth taking if you have to leave your voice behind.
Want to Lead Negotiations on Your Terms?
If you’re preparing for a deal, raising capital, or guiding others through high-stakes decisions, let’s talk. I help founders and leaders protect their upside and negotiate without regret.
Start the conversation at 360strategy
Or connect with me on LinkedIn and let’s talk about building something you’ll never need to walk away from.
Written by Mark Evans MBA Lead Strategic Consultant @360Strategy "I help SMEs navigate disruption, unlock growth, and build future-ready businesses through strategic transformation."
References & Sources:
Bazerman, M.H. and Neale, M.A. (1992) Negotiating Rationally. New York: Free Press.
Fisher, R., Ury, W.L. and Patton, B. (2011) Getting to Yes: Negotiating Agreement Without Giving In. 3rd edn. London: Penguin Books.
Kislik, L. (2017) Why There’s So Much Conflict at Work and What You Can Do to Fix It. TEDxBaylorSchool. Available at: https://www.ted.com/talks/liz_kislik_why_there_s_so_much_conflict_at_work_and_what_you_can_do_to_fix_it (Accessed: 11 April 2025).
Malhotra, D. and Bazerman, M.H. (2007) Negotiation Genius: How to Overcome Obstacles and Achieve Brilliant Results at the Bargaining Table and Beyond. New York: Bantam.
Stone, D., Patton, B. and Heen, S. (2010) Difficult Conversations: How to Discuss What Matters Most. London: Penguin Books.
Voss, C. and Raz, T. (2016) Never Split the Difference: Negotiating As If Your Life Depended On It. New York: Harper Business.
