Leading Through Letdowns

Confidence check: Managing through disappointments

"Vulnerability is not about fear and grief and disappointment; it is the birthplace of everything we're hungry for.” - Brené Brown

This week I had three tough conversations. All were completely different, and none of them ended as I expected. There’s this very unsettling moment when you realize a mutual disappointment is occurring. The knot tightens in your stomach and then there’s the realization that the other person sees things completely differently — and you are not going to change their mind.

Disappointment is a pretty common occurrence when you’re in a leadership position. It’s just not ever an easy pill to swallow.

Flash forward to the emotional soup: a swirl of regret, frustration, resentment, anxiousness, or the overall feeling of unfairness. This is the aftermath. No matter which side of disappointment you’re on, you have all the feelings and so does the person sitting opposite you. And it doesn’t end when the meeting does. So, what now?

“In the wake of disappointment, we’re often told to roll with the punches and move on. But this advice underestimates the emotional impact we experience, the choices we face, and the potential for learning.”¹

Knowing what to do next— how to absorb what I need to—and move forward strategically, is what matters most to me. It’s hard to to get there. Managing myself becomes the immediate focus.

This is where a leader needs to pivot.

Call it what it is

Running from disappointment is exhausting and counterproductive. Pretending it doesn’t really matter isn’t helpful either - after all, I’m human, not a robot. Instead I quickly recognize the feelings by calling them out using “I am” statements: I am frustrated. I am hurt. I am nervous. That short pause is me giving myself some grace first. Acknowledge it.

Separate the situation from the self-worth

My decisions are not definitions of who I am. It is incredibly easy to fall into the trap that one disappointment with inevitably lead to more. The women I lean on say this happens to them all the time. Suddenly we question our worth. That’s when it’s time to be my own hype-woman and remind myself of what I bring to the table despite the outcomes of the current moment. Whether that’s a quick coffee break or writing it in my notebook, I always feel stronger after I reflect on the bigger picture. This will pass.

Let go of the grudges

Not meeting someone else’s expectations means I’m the source of their disappointment. In a small organization, this hits really hard and seems to effect everyone. When the decision lands in a way I didn’t fully anticipate, it’s shocking. But, it does not mean I’m wrong. It also doesn’t mean there is something for me to fix. It’s about keeping focused on the issue, being kind and respectful, and remaining grounded and forward facing.

Write it down, then reframe it

Writing gives me pause, clarity, and perspective, especially when I’m disappointed. Documenting it gives value and truth. I know that one day down the road, when I flip back on my notes of the moment, I will see how this disappointment led to learning and that I grew from it. It’s information for me.

As wellbeing expert Lynn Crilly puts it,

“Turn the negatives into a positive… Think about what you have learned from it, how you could change the way you look at it, and what you can do differently next time. Surround yourself with good people and positive thinking and try not to let it linger.”²

Take care of you

Renowned speaker, author, and leadership guru, Brene’ Brown, spoke at the American Library Association Conference this week and I was so lucky to be there to see it. One of the leadership strategies she stressed was the importance of scheduled recovery. Like professional athletes, recovery allows us the space to rebuild strength and renew ourselves.

When you’re a leader, disappointment unfortunately comes with the job. You get a knot in your stomach and your confidence is as hard to find as your voice. It lingers and it can distract you from the good work you’re doing.

Move forward strategically. Being ready with techniques you can lean into when disappointment happens. And if you can’t get to the strategies right away, get to your people—the ones who ground you.

You got this.

1. 6 Ways to Deal with Disappointment Strategically, Harvard Business Review, April 2025. https://hbr.org/2025/04/6-ways-to-deal-with-disappointment-strategically

2. Crilly, Lynn. Quoted in The Independent, May 2024. https://www.the-independent.com/life-style/england-spain-adams-b2579959.html