Group 103 (2)

Leadership development built from the inside.

I’ve spent nearly 30 years in nonprofit and community-driven work — more than a decade of that in executive leadership. I built HomeGrown Strategies for the leaders I worked alongside, who deserved more than a one-day workshop or executive theory.

I've led statewide programs.

Managed multimillion-dollar budgets.

Overseen hundreds of staff.

Held two VP roles. 

I’ve also been the one in the meeting trying to make sense of conflicting board priorities. The one figuring out how to deliver on what was promised when the funding came in lower than planned. The one carrying a team through a reorg while still keeping the work moving. The one trying to grow as a leader while everyone around me assumed I already had it figured out. 

That experience — both the executive view and the everything-underneath-it view — is what shapes how I work now. 

1200+
Coaching & Facilitation Sessions Facilitated
350+
Leaders Impacted Annually

Why HomeGrown Strategies Exists

When I started coaching and facilitating leadership development across the sector, the same thing kept coming up. Leaders in the middle would tell me, in slightly different words every time: 

“The training I get is either too basic or too executive. Nothing fits the job I actually do.” 

They were right. Most leadership programs skip the middle — the seat where the actual work happens. The seat between strategy and execution. The seat carrying more responsibility than formal authority. The seat where so many high-potential nonprofit leaders quietly burn out, plateau, or leave the sector altogether. 

Confidare is what I built to fix that. A 9-month cohort designed around the six leadership domains that actually shape how mid-level leaders show up — and built to meet leaders where they are, not where someone else thinks they should be. 

Sheila Weber Sig.

How I Work

I don’t do leadership theater. I don’t recycle frameworks I’ve never used. And I don’t pretend that leadership development is separate from the rest of the realities you’re navigating — limited resources, complex stakeholders, mission pressure, real people with real lives. 

When I work with leaders or organizations, I bring three things: 

I hold an MSW, an MBA, and am a Licensed Clinical Social Worker. I’m certified in diversity coaching, positive psychology-based coaching, and emergent learning. 

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Who I've Worked With

As a coach, facilitator, and consultant, I’ve partnered with the Annie E. Casey Foundation, StriveTogether, Lutheran Services in America, Future Farmers of America, and hundreds of individual leaders across the nonprofit sector. 

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Better Together Central Oregon
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VALUES THAT GUIDE ME

What I Care About

Purpose-Driven Impact

I work with organizations that exist to serve their communities. That's not a tagline — it's the reason I'm in this business. My job is to make sure leadership development serves the mission, not the other way around.

Power & Access

Leadership development that ignores power and access isn't real leadership development. I pay attention to who's in the room, who isn't, and how decisions land differently depending on where someone sits.

Accountability

I do what I say I'll do. I expect the same in return. The work doesn't get done by good intentions — it gets done by people who hold themselves and each other to what was promised.

Collaboration With Candor

The strongest work I've done has been with leaders willing to challenge me, push back, and bring their full thinking to the table. Real partnership requires real honesty.

Trustworthiness

What gets said in coaching stays in coaching. What gets discussed in a private cohort stays there. Trust is the foundation of everything else, and I treat it that way.

Working with Sheila as my coach was a turning point. Sheila created a safe space where I felt seen, heard, and challenged in the best way. She helped me confront my own beliefs about leadership and move past imposter syndrome. Sheila has a unique way of helping you step into your power—and I’m so grateful for the strong yet compassionate approach she used to help guide my growth.
Rutila Galvan Rodriguez
Rutila Galvan-Rodriguez
Former Executive Director of Better Together Central Oregon Founder and Principal, Bravo Consulting

If you're a leader ready to grow:

The Confidare Leadership Cohort is the most direct way to keep going — a 9-month structured path built around six leadership domains, grounded in real practice with peers who get your seat. 

If you want a baseline on your six leadership domains before deciding, the Confidare Leadership Skills Self-Assessment is a 10-minute optional starting point. 

If you're developing leaders inside your organization:

The fastest way to figure out what fits is a 20-minute Partner Call. 

Sheila Weber works with you to create individually specific milestones to reach your goals. When your long-term vision seems insurmountable, Sheila can help you adjust your view to see the incremental steps to make your dream a reality. Sheila is an incredible listener and asks the right questions to understand what needs to be changed.
Ashley Washington (1)
Ashley Washington
Senior Director of Membership Experience & Leadership Growth, Lutheran Services in America