Welcome to Roundtable Roundup #2! This spring, the MKE West Roundtable addressed three prominent, real-world topics throughout April, May, and June 2026.
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 (Milwaukee, Green Bay, Appleton, & La Crosse, to name a few) meet up in-person or virtually for your convenience. You can learn more about the topics that are covered monthly and the format of these meetings on our website.
If you missed our first Roundtable Roundup, you can read it here: Small Conversations, Big Leadership Lessons: Roundtable Roundup #1 Insights from the WISL Roundtables.
For this Roundtable Roundup #2, we discussed questions like:
- Can I be ambitious and still be a servant leader?
- How do I hold my ground in a conflict without losing the relationship?
- Is your primary role to “shield” your team from organizational chaos, or to “translate” that chaos into actionable growth?
- How do you implement a top-down decision you disagree with while staying authentic and transparent?
- How do you “serve” a supervisor who doesn’t subscribe to servant leadership without appearing submissive?
- How do you use your authority without weaponizing it during conflict?
Here is a look at how our conversations went:
April Discussion: Leading from the Middle
A key takeaway from April’s Roundtable: What does servant leadership look like when you’re not “at the top”? Influence doesn’t require a title at the top. Servant-leaders can shape culture from wherever they sit, by modeling values, protecting psychological safety on their teams, and staying curious even when things are hard.
Middle managers and team leaders often feel caught between directives from above and the needs of those they guide below.
A quote from Brené Brown, author of “Dare to Lead: Brave Work. Tough Conversations. Whole Hearts,” also resonated with the group:
This theme of “leading from the middle” is one WISL has returned to over the years in our Roundtables. With that insight, we’ve found these actions helpful:
- Don’t label it: You don’t need the words “servant-leader” to practice servant leadership. The most effective influence comes through consistent behavior and mindfulness.
- Results follow the leadership, not the other way around: Organizations that start by chasing outcomes and try to work backward to good leadership often find the sequence doesn’t work. Servant leadership has to come first, with the people of your organization top of mind in your leadership approach.
- Start with your own circle of influence: Middle management, especially in larger organizations, is actually a place of real leverage. You don’t have to change everything; you just have to lead well within your reach.
May Discussion: Balancing Ambition & a Servant Leadership Mindset
A key takeaway from May’s Roundtable: Can you be ambitious and still be a servant-leader? May’s roundtable took that question head-on—and the group reached a clear consensus: the two are not mutually exclusive. In fact, when personal success is tied to helping others succeed, ambition and service align naturally.
The group also reflected on real examples of sacrifice in service: giving up recognition so others can shine, investing time in weekly one-on-one coaching, and one powerful example of a manager who volunteered to be laid off to protect their team.
Roundtable attendees were also asked, “What do you want people to say about how you led, not just what you achieved?” The answers were telling:
- “They helped me grow.”
- “They believed in me.”
- “They were a great teacher.”
This theme is also explored more deeply in our blog post, “Servant Leadership is More Than Just Doing Good Deeds.“
June Discussion: Navigating Conflict Without Losing Relationships
A key takeaway from June’s Roundtable: How do you handle conflict without damaging the relationships that matter? The strength of a leader is not measured by how many conflicts they avoid. In fact, avoiding conflicts can lead to more issues. When you truly care about those you lead, you support them in the good and the bad. It is important to realize that conflict shouldn’t be viewed as a way to grow apart, but rather be seen as an opportunity to understand the root cause of the contradiction and become stronger.
The Roundtable discussed this common misconception that servant leadership means avoiding conflict altogether. In reality, the opposite is closer to the truth.
Discussion questions included:
- When have you seen a leader lean into a difficult conversation precisely because they value the relationship?
- Looking back, what’s one conflict you handled transactionally that you wish you had handled relationally?
- How do you use your authority without weaponizing it during conflict?
A quote from Peter Drucker, author of “The Effective Executive”, stood out:
“The most important thing in communication is hearing what isn’t said.”
Servant leaders who tune into the unspoken are far better equipped to navigate conflict without losing the relationship. The real superpower is caring for people through the highs AND lows of the relationship.
If you’re looking for a safe space to practice navigating these kinds of real leadership challenges, the WISL Roundtables are exactly that.
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.
- Join a WISL Roundtable to connect with others navigating real leadership challenges.
- Attend a Community Conversation event to hear from community leaders who are 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.
Note: Insights and quotes were provided by Gene Wright, Assistant Professor, MSOE Rader School of Business, 2026. Wright also leads the monthly Milwaukee West (in-person) and Milwaukee Downtown (in-person) Roundtable meetings!