Hanging out recently with a few friends, we were choosing top tunes to play. There was additional kudos for an unexpectedly super song. One that fit that bill was Kenny Rogers’ classic The Gambler.

It contains the refrain:

You’ve got to know when to hold ‘em

Know when to fold ‘em

Know when to walk away

And know when to run

I tend to relate such poignant moments to leadership experiences. Because clearly, this song isn’t just about poker – it’s about wisdom, timing, and judgment. Leaders face such situations every day.

How do you relate your leadership wisdom to those four points?

1. Know When to Hold ’Em

Sometimes leadership means standing firm.

• Backing your team when the data supports them.
• Holding onto a vision, even when others doubt.
• Staying the course through early setbacks in a product trial or transformation.

Great leaders don’t abandon convictions at the first sign of friction or a misstep. They know to hold steady when conviction outweighs a comfortable and convenient exit. When they tune into their feelings of worry and translate that signal into meaning.

The meaning that by transforming anxiety to resilience – holding firm and convincing others of their perspective – pays the longer-term dividends.

Think Steve Jobs when countless people inside and outside Apple volunteered, ‘What does Apple know about mobile phones?’ The fact that he envisaged the iPhone as both a computer and a phone in your hand, helped him stand firm.

Or Malala Yousafzai, who, in spite of being shot in the face for her belief in education for girls, stood true to that value.

2. Know When to Fold ’Em

Not every idea is worth pursuing forever.

• A project may not deliver the expected ROI.
• A strategy may no longer fit changing market realities.
• A point of view may be disproven by better evidence.

Strong leaders aren’t stubborn – they have the humility to let go of what no longer serves the mission.

They relinquish their position when the sunk costs are – and will continue to be – heavier than the potential benefits. They draw on their courage and humility to recognize reality and rally others around the revised way ahead.

Netflix was a successful DVD rental business – yet pivoted to streaming – to position itself as a global on-demand content provider. The vision of online had always been a motivator, which may have supported the ability to move – albeit gradually – from one success in the creation of another.

3. Know When to Walk Away

Some situations call for grace and restraint.

• Stepping back in a heated negotiation.
• Leaving the stage for others to shine.
• Ending a partnership that’s “good” but not “great.”

Walking away is not weakness – it’s wisdom in action.

They walk away when continuing on the path would create a loss that no amount of value could justify – and that loss could be financial, strategic or the loss of a trusted relationship.

Satya Nadella exited ventures that drained resources, such as the Nokia phone – and instead focused on cloud computing to transform Microsoft. Even though this meant writing down $7.6 billion of that investment. It was a difficult, but defining moment in his tenure as CEO.

4. Know When to Run

Sometimes the healthiest decision is a decisive exit.

• Escaping toxic workplace cultures.
• Saying “no” to a deal that compromises ethics.
• Leaving when values on the wall don’t match behaviors on the ground.

Leaders protect themselves and their teams by recognizing red flags early – and exiting projects, partnerships and organizations that compromise integrity, safety and all-round well-being.

In these scenarios, running doesn’t equate to quitting, it’s finding a better future.

Susan Fowler was an engineer at Uber who spoke up about the toxic culture. Her conviction to stick to her values, leave the organization and go public to challenge the culture forced a leadership change – and a culture shift.

Knowing when to hold, fold, walk away or run isn’t about luck. It’s about judgment. Tuning into values and the wisdom of emotions helps inform decisions beyond the data in your hand.