Incito Leadership and Executive Coaching


The Dark Side of Optimism


I think successful CEO’s are often Chief Executive Optimists and I’ve worked with a lot of these  leaders who are charismatic, visionary and able to rally people behind a dream of a compelling future. One of my favorite authors, Simon Sinek, in his book Start with Why tells stories of many leaders and CEO’s who have mastered casting a light on a vision for the future and connecting others to believe in that future. While I believe that optimism is an essential trait that sets the best CEO’s and leaders apart, there can be a dark side to optimism that isn’t often spoken about and it has been a derailer of effective leadership for a number of my executive clients. Optimism is hopefulness and confidence about the future or the successful outcome of something and emphasizing the good parts of a situation, or a belief that something good will happen. It has great advantages as it encourages us to take risks, expand horizons, reach goals, innovate and create. It helps motivate us to pursue and achieve our goals, creates hope, keeps our mind at ease and develops resilience.

In his 1990 book, Learned Optimism, Martin Seligman warned that optimism “may sometimes keep us from seeing reality with the necessary clarity.” According to Tali Sharot optimism can create a tendency to overestimate our likelihood of good events happening and underestimate the likelihood of bad events happening. It can lead you to ignore life and business dangers. And it doesn't mean that we think things will magically turn out okay, but rather that we have the unique ability to make it so. Unfortunately that’s rarely true.

If you are the kind of leader that never wants to talk about hard truths, potential negative outcomes and roadblocks then there are some challenges you may encounter in your leadership:

  • Approachability Your bias may make you appear unapproachable by some of your team. How do you relate to the defensive pessimists on your team? Do they feel they can share their concerns and ideas with you?
  • Decision Bias The more optimistic you are, Tali Sharot found “the less likely you are to integrate negative news into your view of the future.” This can lead to bias in your decisions and taking greater risks that you intended and faulty planning. Further, people around you might stop telling you bad news assuming you don’t want to hear it if you gloss over difficult news or dismiss it.
  • Erodes Trust If you take the stance of “trust me” when talking about the future when those around you want to explore evidence that may prove otherwise, dismissing it erodes their trust in you. And, if you’re not willing to talk about negative outcomes, your team may start thinking “Its worse than I thought if you’re not willing to talk about it.” They become even more worried.
  • Building Buy-In and Disconnection Failing to acknowledge tough realities can leave some feeling you don’t understand their struggles and are unwilling to listen which creates disconnection. Your push for others to quickly embrace your optimistic view can leave both of you frustrated and limit buy-in.
  • Overpromise and Under Deliver Those around you can become stressed, worried and frustrated with the potential or perception of over commitment or overly ambitious goals and deadlines.

So how does a leader balance their optimism?

  • Develop Self-Awareness Tali Sharot tells us that raising awareness of your optimism bias is an essential first step and to come up with plans and rules to counter that bias. Accept that not everyone sees the world as you do.
  • Acknowledge their reality Talk about hard and ugly truths in the past, present or future and the challenges that you and your team may face on the road to creating the future. This doesn’t mean you have to dwell on them, but it does mean you must acknowledge they exist.
  • Ask for differing perspectives Allow your team to share their concerns and pessimistic perspectives with you showing you are open to considering all views.
  • Explain your thinking Explain to others your choice to look past the negative news and outcomes and your belief in an optimistic future and why.
  • Help Others See Your Perspective Move from convincing others your view of the future is right and paint a picture for them so they can see the potential for the future themselves. You are often a quick thinker and make fast connections. Not everyone around you will do so as quickly as you do. Be patient. Help them see what you see. It’s a process people have to go through.

With a healthy dose of reality checking practices you can move past your bias and leverage the strengths optimism brings to be a leader others believe in and trust.

UncategorizedJenn Lofgren