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Last night my friend, Steve Woodruff, asked an interesting question on Leadership Chat. Steve asked if a leader could lead with a negative attitude or belief system? Can a leader be a pessimist? The answer is no, a leader cannot lead well with a negative attitude and cannot lead as a pessimist.

But first, a little note on what is not negative.

Sometimes a leader is perceived as being negative because they are forcing the organization to face a cruel, harsh, and unrelenting reality. They may be perceived as being pessimistic because they see a reality that the rest of the organization doesn’t yet understand. The leader may be putting the organization on a more challenging path. I am certain that the men who served Cortes weren’t thrilled to see their boats–their only way home should they fail—caught on fire. It wasn’t pessimism that lit that fire.

Sometimes leaders are perceived as being negative when they challenge what others believe to be good ideas. The devil doesn’t always need and advocate (the status quo usually does a good job taking care of that). But sometimes a leader can seem negative when they push back on ideas. In my experience they do so not because they are negative or because they don’t like the idea. They push back to make sure you have done your best thinking about the idea, and because they want to see how committed you are to the idea. If you cave the first time you are pressed hard on your ideas, a leader suspects you’ll give up when you deal with the challenges that you’ll face making your idea a reality. It’s not negative. It’s a test of your beliefs.

Now, to optimism.

Vision Requires Belief

An organization’s vision is provided by it’s leadership. If the leader is pessimistic and full of doubt, the organization will share those beliefs. This is why a leader must have a positive belief system, a deep sense of optimism. Their beliefs are the beliefs their followers will adopt. Leaders infect the organization with their beliefs, for good or ill.

Great leaders have a steely-eyed, pigheaded optimism that allows them to maintain a belief that they can face the harsh, cruel, unforgiving, and unrelenting realities their organization faces and win. They believe, regardless of the circumstances, that they will still succeed. They will overcome.

Jim Collins, author of From Good to Great, would argue differently. He would point to Admiral Stockdale, who said that the optimists in the Vietnam prison camp he occupied didn’t survive because they expected to be rescued too soon, and so they never faced the harsh reality of what it would take to survive. It may be optimistic to believe you are going to be rescued soon, but it’s equally optimistic to believe you can face the harsh, cruel, unforgiving, and unrelenting realty of a Vietnamese prsion camp and survive.

Optimism provides the foundation for the belief that you will prevail.

Leaders Pick Fights

Leaders pick fights. They decide what battles must be fought. They decided what realities their team must face and what path they must take to move forward. Most of the time they can’t know with certainty that they will win, but without the steely-eyed, pigheaded optimism that supports the belief that they can in fact win, the organization would doubt their future.

Doubt is the slippery slope to fear, fear to scarcity, scarcity to desperation, and then ultimately, to failure.

Face reality. But do so as a pigheaded optimist.


Do you know any great leaders who weren’t optimistic and hopeful about the future?

Can one who is negative and pessimistic lead successfully?

Can you be an optimist and still face reality? Is it required?

Can you pick the fights you need to pick if you don’t believe that you can succeed?

Post by Anthony Iannarino on April 4, 2012

Written and edited by human brains and human hands.

Anthony Iannarino

Anthony Iannarino is an American writer. He has published daily at thesalesblog.com for more than 14 years, amassing over 5,300 articles and making this platform a destination for salespeople and sales leaders. Anthony is also the author of four best-selling books documenting modern sales methodologies and a fifth book for sales leaders seeking revenue growth. His latest book for an even wider audience is titled, The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear, and Boost Success.

Anthony speaks to sales organizations worldwide, delivering cutting-edge sales strategies and tactics that work in this ever-evolving B2B landscape. He also provides workshops and seminars. You can reach Anthony at thesalesblog.com or email Beth@b2bsalescoach.com.

Connect with Anthony on LinkedIn, X or Youtube. You can email Anthony at iannarino@gmail.com

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