Using Kevin O’Leary’s Advice on Deal Making Inside the Organization

Staunch American capitalist Kevin O’Leary once said, “the very best deals are when you feel you left something on the table, and the other side feels the same way”.

He made this statement back in 2020, and it has stayed and resonated with me since, but we don’t need to be making 25 million dollar business deals to heed this advice.

In business and in the workplace we are negotiating and agreeing on ‘deals’ all the time. We’re negotiating a path forward, making decisions that impact other people and their work, etc.

Organizations are complex eco-systems with various factions each applying their own amount of political pressure. When working to establish a path forward we need to please sponsors and stakeholders, and we rely on people to execute and complete the vision. We need to motivate and execution is paramount.

Workplaces will also struggle with the added bureaucracy of hierarchy. You can reasonably say that people in higher levels of authority need the support of other teams and subordinates. Unlike a business deal, where one party can walk away if they aren’t satisfied with the terms, the nature of the relationship is different within an organization. Unfortunately, this could make it easier to deploy management anti-patterns if one isn’t careful rather than align and negotiate with a win/win.

The win/lose proposition may yarner short term results at the expense of the long term. The win/win proposition ensures everyone’s value and validates their long term commitment to the vision. It’s more work, and it requires patience and skill, but it’s ultimately what sets apart, as Kevin would put it, the good deal makers from the bad deal makers.

Taking Kevin’s advice and applying it to ‘deals’ within an organization, may lead to the following:

  • People might not get exactly what they want, or the exact terms they want, but they leave feeling good about the path forward knowing that their input was valued and that their input influenced the agreed upon direction
  • Accountable decision makers leave feeling satisfied that they’ve come to a better decision knowing that everybody has been listened to. The initial approach may have changed due to taking the input from everybody and applying it to the ultimate decisions being made.
  • Details of the approach were adjusted to give everybody more of what they want without compromising on the ultimate objectives.

Just like with Kevin’s deals, if everyone gets most of what they want, it makes for a smooth ride. A ‘deal’ that seems great for one party but is bad for another party isn’t going to work well – there will be a lot of friction when it comes to execution and all the baggage of human emotion that ultimately sabotage long term relationships and execution.

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