Welcome to Roundtable Roundup #3! Each month, leaders from different industries and backgrounds gather for a simple, one-hour Roundtable about what it means to lead with service, humility, and purpose. Multiple locations across Wisconsin meet up in person or virtually for your convenience. You can learn more about the topics covered monthly and the format of these meetings on our website.

If you missed our previous Roundtable Roundups, you can catch up here: Small Conversations, Big Leadership Lessons: Roundtable Roundup #1 and Roundtable Roundup #2: Ambition, Conflict & Leading from the Middle.

Over July, August, and September 2026, WISL Roundtables across the state sat with different topics and questions that include:

• What fuels you at work, and what drains you? Can you name the difference?
• How can a leader give a team more autonomy without becoming hands-off?
• What does “leadership that serves” look like outside of work, in your neighborhood or community?
• Are you leading from ego or from conscience in this moment, and how can you tell the difference?
• When you’re facing a decision without full information, what helps you choose well?
• Can AI genuinely support self-awareness, or does it risk replacing the reflection it’s meant to prompt?

Here is a look at how our conversations went:

July Discussion: Flourishing at Work

A key takeaway from July’s Roundtable: What does it actually mean to flourish at work, and whose job is it to make that possible? At the Servant Leadership Conference in La Crosse, Misty Lown offered a working definition worth sitting with: flourishing is “a multidimensional state of high-level functioning where people feel good and act well within their organization.”

The group worked through four resources every leader has some control over:

• Autonomy: How can we give our teams room to “own the how,” rather than dictating method along with outcome?
• Supportive leadership: How do we stay “a leader in their corner” without tipping into micromanagement?
• Professional growth: How do we make sure people on our team have “a path going somewhere,” not just a job description?
• Recognition: How do we make sure people feel “truly seen,” not just acknowledged in passing?

The last question asked participants to recall a leader who made them feel truly seen, and how that leader pulled it off. The answers rarely involved anything extraordinary; they were the small acts that mattered: a specific detail a leader remembered about them, a check-in with no agenda attached, credit given in the room where it mattered.

August Discussion: Servant Leadership in a Community Context

A key takeaway from August’s Roundtable: Does servant leadership stop at the office door, or does it travel with you into your neighborhood, your volunteer work, and your everyday community life?

The group grounded the discussion in Greenleaf’s own words on what separates a servant-first leader from a leader-first one:

“The servant leader is servant first. . . . It begins with the natural feeling that one wants to serve, to serve first. Then conscious choice brings one to aspire to lead. That person is sharply different from one who is leader first, perhaps because of the need to assuage an unusual power drive or to acquire material possessions… The leader-first and the servant-first are two extreme types.” — Robert Greenleaf, 1977

Thinking about what makes you feel safe to share ideas with other people, what would you want people to say about you in a year, as a community leader?

Being a leader within the community means providing a safe space for people to bring an idea, a problem, or an honest opinion, without the fear of consequences.

September Discussion: Self-Awareness, Your Values & Choices

A key takeaway from September’s Roundtable: Self-awareness is supposed to be uncomfortable — and that discomfort is the point, not a problem to fix.

Much of the discussion centered on a distinction Greenleaf drew between two inner drives: ego-led leadership, which acts to protect status, control, or the identity of being “the good leader,” and conscience-led leadership, which acts for the growth and best interest of others. Positional authority still matters, the group noted, but it shouldn’t replace participation. “You’re the boss” is not a reason to end collective thinking.

Awareness runs in both directions:

• Inward: Naming your own blind spots, strengths, weaknesses, ego, and habitual behaviors (one participant flagged their own tendency to slip into “lecture mode”).
• Outward: Understanding what actually matters to each person you lead. Recognition, support, and development only land when they’re tailored to the individual.

The group also pushed back gently on the idea that strengths are simply good. The more useful question to ponder is what that strength makes them susceptible to missing.

As one closing reflection put it, servant leadership keeps coming back to one question: “What is in the best interest of the person or group I am serving?” But leaders shouldn’t assume they already know the answer. Awareness requires asking, listening, reflecting, and staying accountable for whatever comes after.

Join Us at a Future Roundtable!

Whether you’re a long-time servant-leader or just beginning to explore the philosophy, there’s a seat at the table for you. WISL Roundtables meet monthly across Wisconsin — both in person and virtually.

Additionally, you can attend a Community Conversation event to hear from community leaders putting servant leadership into practice. Sign up for our newsletter to stay informed on upcoming events, new blogs, and practical tools.

Stay curious, stay humble, and keep leading with purpose.

References

Greenleaf, R. K. (1970). The servant as leader. Center for Applied Studies.

Greenleaf, R. K. (1977). Servant leadership: A journey into the nature of legitimate power and greatness. Paulist Press.

Lown, M. (2026, June). Leading so others can flourish [Conference presentation]. Wisconsin Servant Leadership Conference, La Crosse, WI.

Wisl. (2026, September). Servant Leadership in the Age of AI: What Will Always Be Human. Wisconsin Servant Leadership.