Leadership Worth Remembering: 10 Types of Moments the Leaders We Remember Create

When you think back to all the bosses you’ve had over your career, who are the thoughtful, positive, and inspiring ones you remember?

Why do you remember them so well?

In my first year working out of college, I remember one boss who backed up a decision I made in what felt like an overwhelming challenge at the time. Reflecting on that incident more objectively now, he didn’t have to support me at all, and, in fact, he should have held me accountable instead.

He placed me in charge of a new project for a client. To be able to oversee the project, I needed to complete some specific training. He gave me a deadline to complete the training so I would be able to begin the project with no issues.

But, in my busyness of being a new leader in a new role, I forgot about the training. I was not prepared to initiate the project on time for the client. At the time, given my non-existent experience and narrow perspective, it felt like an epic failure. I thought I was going to get fired. I sheepishly informed my boss of the bad news.

He could have fired me. He should have held me accountable based on my demonstrated incompetency. But he did neither. Instead, he took over as the project lead for those first two days in my place, allowing me the time to complete the necessary training. Once I completed it, he graciously handed the project responsibility over to me to see it to completion. There was no yelling, no disappointment speech, no belittling. He risked trusting that I learned my lesson and would not make that mistake again.

15 years later, I still remember my boss and that moment. He unconditionally supported me through a mistake―a pretty major professional failure that I obviously still remember―and gave me space to learn and grow.

Creating Moments

What, then, are the things we remember of our leaders and bosses? We remember the times when they provided a safe place to grow. We remember when they recognized and appreciated us, affirming that our work mattered. We remember how they pushed us to accomplish much more than we thought possible.

These things we remember all come down to moments. Leaders create memorable and meaningful moments.

A moment doesn’t have to be a singular action or event. It can be a finite window of time like a project or a season of work. What’s important about the moment, however, is that a leader creates a memorable feeling through their words or actions. This memorable feeling is anchored to a moment that a person can look back on and say, “This leader made me feel ____ when she did/said ____,” just like my previous boss did for me so many years ago.

Leaders create moments, and people remember moments. Ultimately, we bond over, grow from, and feel seen, heard, and valued through the specific moments that leaders create for us. These leaders leave us feeling capable, inspired, and like we belong. They make us better than we were before.

Through mentoring and reflecting with junior leaders and working with clients, I have identified 10 types of moments that leaders can create. These are ways we positively impact others’ lives, and why we remember some of our own bosses and leaders years later.

10 Types of Moments Leaders Create

The leaders we remember:

Let us be our whole selves: They embraced us at our worst as much as at our best. We were encouraged to be our authentic selves, even in tough and challenging situations.
Provided a safe place to learn and grow: We felt safe to learn, to ask questions, to not know the answers, and to offer our perspectives to the group.
Were disciplined and led by example: They impressed us with their work ethic, care, dedication, and discipline in how they managed their time and themselves. They led with character, always doing the right thing for the right reason in the right way. We wanted to be like them, even when it seemed impossible.
Backed us up in challenges: They had our backs, even when it cost them something. We were never left hung out to dry. If we needed support or “top cover,” they provided it. They backed us up when facing adversarial clients or challenging leaders in the organization.
Opened doors and new opportunities: They knew our personal goals or desires, cared about them, and did what they could to support us. They even went out of their way to create opportunities for us.
Recognized and appreciated us: They took the time to express gratitude, which made us feel seen, valued, and like we belong. Their appreciation was also beneficial, serving as positive feedback that we could see, understand, and act on.
Developed us: They understood our unique developmental needs and poured into us, committing personal time and resources to invest in our skills, relationships, and growth as leaders.
Inspired us to stretch further: Placed us in challenging roles with seemingly overwhelming responsibility and matching authority. These were tough, but they stretched our abilities and capacities, and they encouraged and supported us through it all.
Affirmed that we and our work mattered: Communicated perspective and helped show us how our work contributed to a much larger picture and had impacts beyond what we could see ourselves.
Supported us through mistakes and failure: Did not let failure define us. They helped us to learn from it, grow from it, and use it as part of our leadership story so that we can show other leaders that failure is not the end.

What Can We Do?

As leaders, how can we use these to positively impact others? I know when I look at this list, I easily get overwhelmed. That’s a lot of things to be and do, and a lot of things expected of me!

I recognize that leadership is demanding―it requires our best every day―but let’s look at some simple steps we can take to tap into the power of these moments in our daily leader actions, big and (more importantly) small.

First, know that every event and interaction is an opportunity to create a moment. Your words, your attitude, your gestures, and your actions have more power than you think. Even the smallest of things can have a huge impact on creating one of these types of moments―how you respond to bad news, what questions you ask in meetings, asking more and talking less when you spend time moving about checking on different teams.

Second, remember that these are not singular, grand gestures. We don’t make a big deal about doing one of these once and consider it mission complete. These are genuine, personal, and meaningful moments that we intentionally try to craft daily.

Third, look at your calendar for this week. Is there an event that you can thoughtfully shape to make a bigger impact? This is an easy way to start developing a habit. Maybe a colleague is retiring, and they have a small farewell get-together this week at lunch. How can you help make this special event into a moment they will remember? Can you share some comments like a personal story, the impacts they had on the organization, who they were and their character, and how they made you and the organization better? Moments like this orbit all around us each day. Try and identify one this week and craft it into a moment.

Final Thoughts

Several years ago, while managing a team, I had a junior colleague who had just joined us. We were minutes away from an important presentation to higher headquarters when I found him in the hallway, visibly frantic. He couldn’t locate the deliverable documents he was responsible for, and the weight of that responsibility was crashing down on him. When he saw me, he froze, fearful of admitting the mistake and bracing for the frustration he assumed would follow.

After he explained the situation, I simply said, “Jose, thanks for telling me. First, let’s take a deep breath. We’re going to be okay. How about you head back into the office, keep looking, or reprint them if you can. We will start the presentation and manage it until you can bring the documents. I appreciate you letting me know.” My calmness seemed to steady him, and together we moved forward.

Looking back now, the incident feels minor—hardly worth remembering. And in truth, I didn’t remember it at all until months later, when Jose brought it up himself. He told me how impactful that moment had been for him. As a new member of the team, he had expected anger, disappointment, and even consequences. Instead, he said that he found compassion and support. That simple response, which I barely registered, became a defining memory for him. And I must think that I treated Jose this way because of the compassion my first boss showed me.

This is the quiet power of leadership: we often don’t realize when we are creating meaningful moments for others. What feels small or routine to us can be monumental to someone else. Thoughtful leadership is not about grand gestures—it’s about a steady presence, a calm word, and unexpected grace in moments of stress. And often, we won’t learn until years later how deeply those moments mattered.

In the end, we don’t put effort into designing deliberate and impactful moments like these so that we become memorable bosses or leaders. This is not a self-enhancing exercise; it is not about us. It is a way to be more intentional in creating a workplace and workday experiences where our people feel valued, seen, inspired, capable, like they belong, and ultimately better than they were before. It’s about having significant impacts on others, through others, and for others.