Leadership Lessons from North London: Nice Guy or Tough Negotiator?

“The ability to walk away is important, but the ability to build a bridge is essential.” - William Ury (Co-author, Getting to Yes)

When Daniel Levy stepped down – whether voluntarily or otherwise -  as Tottenham’s long-standing executive chairman, many wondered: who could fill the void of one of football’s fiercest negotiators?

The answer came in the form of Vinai Venkatesham - former Arsenal CEO, known not for confrontation, but for empathy, collaboration, and relationship-building.

This contrast between Levy and Venkatesham offers a powerful lens on leadership and negotiation that extends far beyond football. It also demonstrates a view that a more confrontational style can only take an organization so far.

Combative vs. Relationship-Focused Leadership

Levy built Tottenham into a financial and infrastructural powerhouse. But his combative style in negotiations left rival clubs feeling drained, resentful, and reluctant to return to the table.

Venkatesham, by contrast, is praised for humility, inclusivity, and a calm authority. He delegates to experts, makes people feel heard, and creates goodwill - the sort of leadership that builds sustainable partnerships.

“In negotiation, it is not what you can take from the table, but what you can build around it that determines lasting success.” - William Ury

Valuing People as a Performance Strategy

During the pandemic, Venkatesham was described as a source of comfort and reassurance at Arsenal. He combined tough decisions with empathy, showing that valuing people is not “soft” leadership, but a strategic lever for resilience and productivity.

Research - and common sense - tell us that people who feel valued give their best work. It’s true in football, and it’s true in every organisation.

“Successful negotiators are empathetic. They can see the situation from the other side’s perspective as easily as their own.” - Herb Cohen

The Hidden Cost of “Winning” Deals

Negotiation isn’t just about securing terms today - it’s about reputation tomorrow. A combative win can sour relationships and close doors. A collaborative approach, even when firm, leaves counterparts open to future business.

The question for leaders: are you creating conditions for repeat collaboration, or leaving people relieved the engagement is over? Just because you've done the deal doesn't mean you've been successful. If your counterparts feel resentful and/or exhausted, they're unlikely to want to do business with you again, and they're likely to tell others about their experience!

“The most dangerous negotiation is the one you don’t know you’re in.” — Chris Voss

Strength Doesn’t Have to Shout

Being “nice” isn’t weakness. Venkatesham proved this by making decisive calls - from sacking a manager to backing bold appointments - while maintaining trust and respect. Describing someone as nice is frequently an indication they’re perceived as weak. However, demonstration emotional intelligence, discernment and respect has been shown repeatedly to generate better results, and higher levels of commitment and performance.

True authority often comes not from being the loudest in the room, but from being the leader who builds trust, empowers others, and ensures people leave the table wanting to work with you again.

“If you want to make peace with your enemy, you have to work with your enemy. Then he becomes your partner.” — Nelson Mandela

The Takeaway for Leaders and Negotiators

• Short-term wins vs. long-term trust: A deal secured with resentment attached is rarely a win.
• Valuing people multiplies performance: Compassion isn’t the opposite of performance - it fuels it.
• Quiet strength endures: Empathy, clarity, and inclusivity can achieve more than aggression ever will.

“Win-win is not a technique. It’s a total philosophy of human interaction.” - Stephen R. Covey

Whether in the boardroom or on the pitch, the lesson is clear: Yes, we want to win, but how we do it is important, and understanding the consequences of our approach equally so. Leadership is less about beating opponents and more about building partners.