In his song “The Gambler”, referring to a game of cards, Kenny Rogers sang “You have got to know when to hold ‘em, and know when to fold ‘em…

Every time I heard it, I asked myself, “How do I know when to….” Thankfully, Whitney Houston sang “How Will I Know”, capturing what I was wondering, validating my dilemma. Thank you, Whitney.

As leaders, we often find ourselves in similar dilemmas. For example:

• Do I speak up (and possibly risk getting shot down), or do I stay quiet?
• Do we continue to invest in a team member, or do we let ‘em go?
• Do we continue to invest in this initiative…project…business unit with the hopes of it turning around, or do we finally shut it down and write it off, so that we can focus on more profitable portions of the business?

Is continuing to move forward an act of courage and confidence? Or is it an act of stubbornness, pigheadedness, and foolishness? It’s a delicate balance, for we must persevere to achieve anything of significance. But persevering for the wrong reasons can be very costly.

So how do you know…when to keep pushing forward, and when to pull back?

The most useful guidance I have found comes from Bill Walsh, Former Head Coach of San Francisco 49ers, in his book “The Score Takes Care of Itself: My Philosophy on Leadership.” Here’s what he states:

“A leader must be keen and alert to what drives a decision, a plan of action. And that one of the greatest leadership challenges is to recognize when hubris has you in its grip before it is too late.”

Based on this, Bill offers the following checklist to keep in mind when making critical decisions:

1. A leader must never quit
2. A leader must know when to quit
3. Proving that you are right, or proving that someone is wrong, are bad reasons for persisting.
4. Good logic, sound principles, and strong belief are the purest and most productive reasons for pushing forward when things get rough.

What do you think? How do you know? I would love to hear from you. Thank you.


Vinay Kumar

Vinay Kumar

Vinay Kumar is a Leadership & Executive Coach, Author, Speaker with Leading for Breakthroughs. Prior to entering professional coaching, Vinay spent more than 20 years co-leading a family business. Now his clients include private and public sector enterprises, including family businesses. Vinay offers leadership coaching, leadership education programs, and designs and facilitates leadership retreats. He also serves as Faculty in George Washington University’s Leadership Coaching Program. His most recent book is Language and the Pursuit of Leadership Excellence: How Extraordinary Leaders Build Relationships, Shape Culture and Drive Breakthrough Results.

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