Seizing the Big Moments that Define Your Leadership Career

We work for decades, yet for most of us, there are a handful of moments in time that define the course of our careers. Unfortunately, these moments—opportunities or crises—don’t come with a caption suggesting, “Hey, pay attention and embrace this mess because it’s going to turn out to be important to you.” For individuals who choose to lead, it pays to see the signposts. Here are significant moments in the career of everyone who leads that merit your complete engagement.

The Moments that Define Your Trajectory as a Leader

Signing On to Be Responsible for the Work of Others

For many, the path to a leadership role is accidental or unplanned, passing through various positions, including team lead, supervisor, and manager. But let’s face it, as children and young adults, few of us dreamt of being responsible for the work of others and all the inherent headaches and responsibilities this work entails. We see ourselves using our talents to do something we love in pursuit of something we care about in our lives. And then, six months out of college, your boss asks whether you want to supervise a team, and in your enthusiasm and naivete, you say, “Sure.” (This situation may be autobiographical!)

That’s not the moment you decided to lead. That’s when you unwittingly signed on for your learner’s permit. After flailing and assuming you’re not a complete tool at the role and your team members don’t rebel, you might get a chance to continue to try a slightly more significant role for size.

Making A Deliberate Decision to Lead

The moment I’m referencing here is your deliberate decision to invest yourself in helping others and your organization via leadership roles. By this time, you understand the challenges, headaches, and potential rewards of the role, and you’ve decided to focus on guiding, coaching, and navigating tough decisions in support of others and your organization. You effectively are letting go of the focus on you to focus on them.

Every successful leader I’ve encountered recognizes this moment clearly in hindsight. Many describe wishing they had realized it and embraced it sooner. “I worked at the manager role for a few years until it dawned on me that I loved helping people succeed, and this was what I wanted to do at this stage of my career and life,” offered a senior executive. Her follow-on comment was telling, “It’s the helping people grow and succeed part of my leadership work that allows me to tolerate the organizational politics and sleepless nights that come with the role.”

A retired CEO that had started his career as an engineer described the moment he recognized his calling as a leader. “I had just been awarded my third patent. It felt good, but it dawned on me that I could make a bigger contribution to my company and society if I built teams of engineers able to realize their vision for our technology. I never looked back.”

A few questions to ask yourself sooner than later:

Does the work of leadership bring out the best in me?
Am I motivated to serve others?
Am I willing to put their needs ahead of mine?
Does helping people become their best versions of themselves in their careers excite me?

The Moment You Decide the Type of Leader You Aspire to Become

Deciding to invest yourself in the work of leadership is essential.

Defining the leader you aspire to become is priceless.

Late in 2021, I shared an article at SmartBrief on Leadership titled: “Think deeply about the leader you aspire to be,” In this article, I offer detailed guidance on tuning into your aspirational leadership self through a series of prompts. I wish someone had asked me about the leader I aspired to be earlier in my career. It would have steeled me for the challenges along the way and ensured I had a north star to turn to in difficult moments. Additionally, I would have served my team members and organizations more effectively.

Prompts to Help You Define Your Aspirational Leadership Self

Don’t wait to define the leader you aspire to be in your life and career. And don’t reduce the exercise to a series of cliché-riddled bullets. Be creative.
Write a future-self narrative.
Use a version of the eulogy exercise, but instead, project forward to a future date when you are surrounded by people you worked with during your career. What do you want them to say about how you affected them?
Bring a picture of that person from your life who has influenced you the most. Tell a story about what they did and why you admire them. Describe how you are striving to live to their legacy. Giving people context for who inspires or inspired you and sharing this story is powerful for your team members.

Regardless of how you get there, if you’ve decided to lead, it’s imperative to create your aspirational leadership self to serve as your north star.

The Moment(s) When You Make a Stand

While the above moments are singular events, every leader faces one or more moments in their careers when they must commit to a position in the face of uncertainty and often in opposition to the opinions and encouragement of peers or a boss. These are existential leadership moments where you understand the stakes for you and others are high, and the only thing you have to guide you is the north star of your aspirational leadership self and your values.

It bears highlighting that many individuals fail in these challenging moments. They fail to do what they know is right and bow to political and extraneous pressures. From going along with decisions they know are flawed to crossing ethical boundaries in the name of profits or progress, these are opportunities to take a stand. It’s frightening to take a stand, but if you compromise, you will be failing yourself, those who depend upon you, and everyone who has inspired you to be a good person and leader if you compromise.

Moments that Challenged Me to Live Up to My Aspirational Leadership Self

While we will all face different flavors of moments to make a stand, a few of mine are instructive.

That time I was laughed at for proposing we move a particular person into a key, new role. I stuck to my position, and she succeeded wildly.
That time I stood in the boardroom of a potential acquirer and declared the emerging deal the “worst possible outcome for our people and their careers.” The deal fell apart for various reasons beyond my boardroom protest, and a fabulous path opened, giving many two decades of experience and growth with a tremendous firm.
When I flew 13 hours to meet with my overseas bosses for a one-hour meeting to try and convince them to reverse course on a big strategic decision. They backed my requested change partly because I displayed the commitment to come to them and discuss the issue.
When asking a board of directors to give us 18 months of break-even to fund a project that would define the future of the business for years. They did, and it did!

I understood my job was on the line for all but the personal advocacy item. Yet, for each of those situations were moments I knew I had to make a stand or risk being untrue to my aspirational leadership self.

The Moment When You Fail to Make a Stand and Face Yourself in the Mirror

You are human, and at some point, you will fail your aspirational leadership self. I did, and it burns in my gut to this day. I uncharacteristically compromised on several key strategies and leadership decisions and failed to engage in the robust dialog essential for moving things forward. I allowed politics and the feeling that making a stand would be destructive to the team to trump what I knew in my heart was right. In hindsight, I’m incredibly disappointed I lost my resolve in this environment. In part, my failure to make a stand regardless of personal costs sealed the fate of this small tech firm filled with good people. While painful, this misfire was a powerful learning lesson for me.

The Bottom-Line for Now:

The decision to lead, the decision to define the leader you aspire to be, and the situations you must make a stand are the defining moments in your leadership career. These decisions ripple through our lives and the lives of others. Start by investing time in defining the leader you aspire to be, and then recognize those big moments where you get to prove worthy of the label of leader.