Relationships at Work - The Leadership Guide to Building Workplace Connections and Avoiding Blind Spots.

Defining Success: The Honest Questions Every Leader Must Ask

Russel Lolacher Episode 223

As leaders, how often do we pause to define success—not for our organizations or teams, but for ourselves? 

In this episode, we explore the deeply personal nature of success and the critical questions leaders must ask to align their actions with their values. From building team culture to balancing productivity and people, we dive into the trade-offs leaders face and the impact of their choices. Tune in for an honest conversation about how redefining success can reshape your leadership approach and legacy.

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Welcome back to Relationships At Work – Your guide to building workplace connections and avoiding leadership blind spots..  I’m your host Russel Lolacher, a communications and leadership expert with a couple of decades of experience and a heap of curiosity on how we can make the workplace better. If you’re a leader trying to understand and improve your impact on work culture and the employee experience, you’re in the right place.

This mini-episode is a quick and valuable bit of information to help your mindset for the week ahead. 

Inspired by our R@W Note Newsletter, I’m passing on to you…  

The Honest Truth In Defining Our Success


When we step into leadership roles, how often do we pause and think about what success really means? And I’m not talking about success for the company, or for the people we report to, or even for our teams—though those things do matter. I mean for us. Personally.

What do you want to bring to the role? What do you want to accomplish? How will you know if you’ve been successful? And here’s the big one: when it’s time to leave this role, what kind of legacy do you want to leave behind for the people you’ve led?

Success is personal—it’s deeply tied to our own sense of meaning and value. That’s why, when I’m working with leaders, one of the first questions I ask is, “What does success look like for you?” And let me tell you—it’s almost always a conversation they didn’t realize they needed to have.


 Now, here’s the thing: defining success requires honesty. Real, gut-level honesty. It’s about looking at how we’re showing up—for ourselves, for our organization, and for our teams—and being willing to admit what’s working... and what’s not.

Let’s break this down with a few examples because success means different things to different leaders.

 If your idea of success is about building something—a product, a service, a system—then naturally, your focus is going to be on productivity and delivery. That’s great, but let’s be honest: this approach puts results ahead of people. It’s about what we produce, not how we engage or empower. The ends take priority over the means.

 If your version of success is about making your boss happy—and yes, I’ve heard leaders say this—then your focus shifts upward. You’re constantly tracking your boss’s moods, reacting to their needs, and making sure your team is, too. But let’s call this what it is: you’re not leading. You’re following orders. You’re shining your light upward while leaving your team in the dark.


 Now, if success for you is about fostering a healthy team culture, that’s a different story. Here, you’re prioritizing things like active listening, feedback, professional development, and open communication. And while that sounds ideal, it comes with trade-offs. This approach might mean pushing back on the hierarchy, setting boundaries, or defending your team when organizational demands clash with their well-being.

 Here’s the truth: every definition of success comes with trade-offs. If success for you is X, then something else—Y or Z—gets deprioritized. That’s just reality. And the sooner we’re honest about those trade-offs, the sooner we can align our leadership with what we really value.


 So, let me ask you:

  • What does success mean to you, personally, as a leader?
  • What trade-offs are you making in pursuit of that success?
  • And—here’s the tough one—are you being honest with yourself about how your definition of success is impacting your team and organization?


 If we’re willing to sit with these questions—really sit with them—it can completely reshape how we lead. It’s about what we prioritize and what we choose to let go.

The challenge, though, is in being brutally honest with ourselves. What aren’t we valuing right now? What truths are we avoiding? 

Because once we face those truths, we might find that the success we’re chasing isn’t the success we actually want. 

And that’s where the real leadership begins—when we align our actions with a definition of success that’s meaningful, sustainable, and human.

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