Leadership Optimism: Ten Tips for Choosing an Alternative to Pessimism

Years ago, one of the teams I led created something that didn't work. For as much as I talk about the importance of cultural awareness, we created something that didn't resonate with our target audience. We simply missed the mark.

What it was and why it didn't work aren't important. But it was a big deal for us. Years later, it still gets joked about. The jokes are actually pretty funny. But, even though the team most directly responsible for its creation is able to laugh about it now, I can tell that it still stings a bit.

That team (and its leader) had two choices: they could have gotten frustrated, mad, and angry. After all, they worked tirelessly and put all of their creative energies into something that bombed. No one would blame them for being upset. But they didn't do that. Instead, they chose to say, "We're going to let this experience make us better. We won't let this happen again. We'll learn from it. We'll adjust processes. We'll do whatever we have to do so that we create content that resonates with our audience."

They're achieving that goal. The team's work since then has been getting better and better. Not because of what it is (although it is fantastic), but because it has hit the mark with our people. And because they made a smart choice. I consider it leadership optimism.

It's amazing how much power lies within a simple choice. What if we consciously started choosing to look at difficult situations through the lens of what we could learn from them? What if we chose leadership OPTIMISM instead of leadership PESSIMISM? What if we started drinking from a glass that was half full of opportunities for growth, refinement, and increased cultural awareness instead of the half empty cup of anger, bitterness, and regret?

Here are ten practical steps I think we can take to shift our perspective:

Acknowledge missteps and misses.
They're bound to happen and they give us the best opportunities to learn. When we acknowledge the times that we fumble the ball, we gain credibility. 

Identify the potential for good in every situation.
It's easy to see the bad. Do the hard work of searching for and identifying opportunities where something ugly can be turned into something beautiful. 

Always give the benefit of the doubt and believe the best of people.
You want it from others, right? So do unto others as you'd have them do unto you. Imagine how different team environments would be if people did this for one another all the time.

Work hard.
There's no substitute for hard work, especially after a "miss." Your leaders will respect your efforts. The people around you will take note. The things you create will be better.

Ask for feedback.
The proverbial definition of insanity is doing the same thing over and over and expecting a different result. Asking for feedback is one way to make sure you're not repeating mistakes of the past.

Ask questions.
Find out where you went awry. Gather information and file it away. And be bold about it. Create an environment where people feel safe sharing honest, respectful, constructive critique with you. Ask for it and then thank the person who shared it with you.

Celebrate successes.
Make sure you mark moments. Recognize when you've achieved a "win," especially if it's in stark contrast to the miss. Celebrate your teams and their efforts in meaningful ways.

Embrace humor and don't take yourself too seriously.
If you can poke fun at yourself, you'll put everyone around you at ease. Sometimes, a little dose of well-placed self-deprecating humor goes a long way.

Don't hold grudges.
It's destructive and the only one you’ll hurt is yourself. Regardless of how wounded you may have been in a particular situation, do your best to offer forgiveness.

Keep the vision and goals in mind.
It's easy to get pessimistic when you're unclear about what you're trying to achieve. Remind yourself (often) of why you're doing what you do. Remind those around you, too. And run everything you create through that filter. 

I'm convinced that the more optimistic our outlook is, the healthier our teams will be.