Pragmatic Optimism

Combining a Positive Outlook With Practical Realism

A few years ago, a leader in our company shared with me that one of our team members was leaving for another opportunity.

My response:

“I’m not worried about it; I’m confident we’ll be fine.”

It wasn’t until a while later that I received feedback on this and other situations where I came off as dismissive and lacking concern, negatively impacting the team during challenges.

While that was not my intent, I had yet to realize, accept, and embrace the understanding that perception shapes reality, and, therefore, precision in language and responses is critical.

It’s not just about what I think—that’s not leadership.

As leaders, if we don’t acknowledge that truth, listen, and meet people where they’re at, no amount of confidence or optimism will be well received because others won’t be able to see the same future.

One of the most important lessons I’ve learned since then is the concept of pragmatic optimism. In other words, maintaining a positive outlook while leading with a practical realism to empathize with the current state.

Operating on the spectrum of optimism/confidence and empathy/humility is a fundamental dichotomy we must be mindful of and lead ourselves within.

It’s about harmonizing perspectives to remain resilient and empower the team to take steps forward while not losing sight of the need to lead with emotional intelligence—after all, leadership development is human development.

Here’s what I could have done differently in that situation (or any other where challenges arise):

Acknowledge the Impact

Start by recognizing the implications for the team. Show empathy and understanding of the circumstances and listen to those closest to the action. Our view from the top likely overlooks essential perspectives and daily impact.

Express Gratitude

Show appreciation for the departing team member. A team founded on trust is built on genuine relationships. Don’t overlook this, as it significantly contributes to how the team will feel and perceive the dynamics of the required near-term adjustments.

Convey Confidence

Share confidence to reinforce the trust and belief in the team’s ability to handle the transition. A major component of leading a team through adversity is aligning on collective steps forward. The only way for a team to “figure it out” is together, leaning on each other’s characteristics and strengths.

Encourage Input

As such, quickly gather the team to acknowledge the situation's impact, collect feedback, and ensure all necessary information is surfaced to collaborate and align on a plan.

Show Support

Offer support to the team during the transition. This isn’t about grand gestures; it’s about the intention of showing up for the team in a time of need, no matter the scale of the obstacle. It can be as simple as, “How can I help?”

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If I could return to that moment, I’d take a different approach in my response, regardless of how I felt the outcome would be. All together, it might look like this:

“Thanks for letting me know. That’s tough—they’ve added considerable value. I understand this is a challenging time for the team, and I have full confidence in our ability to adapt and figure it out together. Let’s meet as a leadership team and discuss the impact, what we may need moving forward, and a communication plan with the rest of the team. I’ll support however I can.”

I was genuinely not worried about the dynamic. Ultimately, that person's departure didn’t drastically impact the company, but that’s not the point.

Leadership is not about being right or wrong. It’s about sensing, understanding, and responding to how others perceive a situation—empathy and compassion.

Empowerment doesn’t happen without first balancing confidence with humility and courage with curiosity.

Leading with pragmatic optimism is not for us; it’s for them. It’s taking a practical approach to sit alongside others to convey belief in the team while ensuring they feel seen, heard, and supported rather than dismissed.

Sometimes, that may take longer than we’d like. However, our role is not to convince but to lead so that we align a group of individuals who inevitably have different perspectives.

Maintaining trust requires navigating incredible nuance and fine lines, so mindfulness and intention are common values to lead by. Remember, every decision, action, behavior, and response is being watched.

“Optimism emerges from a faith in yourself and in the people who work for you. It’s not about saying things are good when they’re not, and it’s not about conveying some blind faith that ‘things will work out.’ It’s about believing in your and other’s abilities.”

—Bob Iger, CEO of Disney

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