When it comes to blending strategy, product ownership, and the human side of tech, few do it with as much creativity and energy as Bree Gillespie, Vice President of Client Engagement. Bree has helped countless organizations turn big-picture visions into real-world results, always keeping things approachable, inclusive, and fun.

For this conversation, Bree sat down with her colleague Patrice Castellano, Director of Support Services, to talk leadership, women in tech, and what it really takes to make strategy stick. Their candid Q&A touches on everything from bold ideas and product ownership to coffee, playlists (PRINCE!), and the future of women in leadership.

Patrice: Let’s start light. What’s one word your team would use to describe your leadership style?

Bree: Ha, maybe not so light! But I’d say “direct.” I’ve learned that honesty and clarity go a long way, especially for women in leadership roles where it’s easy to second guess. I also think “growth mindset” is part of my style, it’s not one word, but it matters in both sports and leadership.

Patrice: You’ve worn many hats including strategist, product owner, and consultant. How do you know when to zoom out to the big picture and when to dive into details?

Bree: It’s really about the process. You have to evaluate where you are and what will have the biggest impact. Sometimes that means big picture visioning, sometimes it means narrowing in on details. I think of it as convergent and divergent thinking, a funnel that expands and contracts depending on the stage of the work.

Patrice: Strategic planning can sound a little stiff. What’s your favorite way to make strategy feel alive and fun?

Bree:

I think of strategy as creative problem solving. At its heart, that’s exciting. When you keep people at the center, making sure it’s interactive, human, and focused on real change, it becomes inspiring instead of overwhelming. Strategy should be about making lives better, not just creating a list of tasks.

Patrice: Product ownership is a balancing act with features, bugs, deadlines, and big ideas. What’s your secret sauce for keeping it all moving without losing the human side?

Bree: Teamwork. None of it happens without a strong team. I see myself as one cog in a bigger wheel, and when it comes to the human side, I always try to see through the lens of real world impact, how the product actually helps organizations and the people doing the hard, important work in their communities.

Patrice: As a woman in tech, what’s been the most surprising or funniest moment you’ve had breaking into the space?

Bree: Honestly, just learning with open eyes. Tech is one of those areas where you never “arrive,” there’s always more to learn. Staying humble and open has been the biggest key to success.

Patrice: If you could rewrite the rules of leadership for the next generation of women, what would you toss out and what would you keep?

Bree: Toss out doubt. Take up space, speak up, and don’t be afraid to push. Everyone deserves a seat at the table, and we can set the example by showing up fully every day.

Patrice: What’s the boldest idea you’ve ever pitched in a strategy session or product meeting? Did it land or flop?

Bree: Oh, plenty of flops! That’s the nature of innovation, you have to be willing to let go of a lot of ideas, even ones you love. Every so often, one sticks. Recently I pitched a product extension idea, how to add more value for clients through tech that makes life easier for end users. That’s the kind of impact that lasts.

Patrice: Everyone talks about innovation, but what does it actually look like in your daily work?

Bree: For me, it’s constant rethinking, what can be better, what’s next, how do we improve? It’s fun to chase the big idea, but a lot of innovation comes from revisiting the plan, iterating, and making sure the small details line up so the big impact can happen.

Patrice: Coffee, playlists, post-its… What’s your non-negotiable tool when you’re deep in planning mode?

Bree: A homemade latte with honey from my Aunt Dot’s bee farm. Nothing else compares.

Patrice: Last one, what advice would you give young women who want to lead in tech or strategy but don’t see many role models who look like them?

Bree: If the elevator tries to bring you down, go crazy and punch a higher floor. (Thanks, Prince!) Don’t stop until you get what you want and deserve.

Interviewing Bree reminded me that leadership isn’t just about strategy or great products, it’s about staying human, curious, and open to possibility. Bree embodies all of that and more. My hope is that readers leave with the reminder that women in leadership are shaping the future of tech and strategy in ways that are both bold and approachable.

Until next time,

Patrice Castellano, Director of Support Services

At coLAB, when we partner with organizations, we begin by helping them assess their readiness for strategic planning. Here are some of the signals we look for to determine if it’s the right moment to embark on the journey. In each of these phases, we make pointed recommendations to ensure your team is set up for a successful strategic planning process, one that results in a meaningful and well-crafted plan you can act on with confidence.

Board Curiosity?

Do board members express confusion about where the organization is headed? Do conversations keep circling back to questions like: What’s our long-term direction? How do we prioritize among so many competing needs?

How coLAB helps: We listen for these pain points in board conversations and use facilitated dialogue to clarify where the uncertainty lies. Our team then designs a readiness framework that pinpoints whether the board needs deeper alignment before entering into full strategic planning.

Can You Show Impact?

Funders and donors increasingly want to see measurable outcomes, not just compelling stories. If your organization struggles to show how programs create real impact or if your team lacks the tools to track it, fundraising and credibility may be at risk.

How coLAB helps: We begin by assessing your current data systems, reporting practices, and evaluation culture. From there, we recommend tools and approaches to strengthen outcome tracking, ensuring you’re ready to link strategy to measurable impact.

Is Leadership Aligned on the Path Forward?

When executive teams aren’t aligned on the future, energy gets scattered. Some leaders may pursue funding opportunities that don’t quite fit. Others may push initiatives that compete for limited resources. A strategic plan creates shared clarity, ensuring everyone is pulling in the same direction.

How coLAB helps: We use structured interviews and alignment sessions to uncover where leadership perspectives converge, and where they diverge. This assessment allows us to build a roadmap that creates consensus, so planning starts from a place of unity.

Do Staff Have the Capacity to Succeed?

Does your board ask staff to deliver on new priorities without the time, people, or resources to succeed? Do your staff feel like they’re constantly reacting instead of proactively shaping their work? Strategic planning can bridge these gaps, aligning ambitions with capacity.

How coLAB helps: We engage staff at all levels to understand real capacity constraints and resource challenges. This input ensures the planning process is grounded in reality and positions the organization to set achievable goals.

Are Your Community’s Needs Outpacing the Resources You Have?

Sometimes the community’s needs don’t match what the organization currently has to offer. Other times, an organization simply doesn’t have a clear picture of the community’s most urgent priorities. In both cases, strategic planning provides the space to step back, gather input, and chart a sustainable path forward.

How coLAB helps: We conduct stakeholder interviews, focus groups, and community assessments to provide a clearer picture of needs. This gives leaders the confidence that their strategy is not only aspirational but also responsive to the community they serve.

Is Your Executive Director or CEO Prepared to Lead This Strategic Change?

Finally, much depends on the executive leader. If the Executive Director or CEO  is open to reflection, committed to honest conversations, and eager to build alignment, strategic planning can become a transformative process, not just for them, but for the entire organization.

How coLAB helps: We work closely with the executive leader as a thought partner, providing coaching and guidance through the readiness phase. This ensures the leader is equipped to champion the process and sustain momentum once the plan is in motion.

Ready to Take the Next Step?

Strategic planning is more than a retreat or a document, it’s a chance to create clarity, strengthen alignment, and unlock your nonprofit’s potential. If any of these signals sound familiar, it may be the right time to begin.

At coLAB, we specialize in helping nonprofits assess their readiness and guide them through people-centered, data-informed planning processes that set them up for long-term impact.

The sustainability assessment gives you the “what,” a snapshot of where your organization stands today across key dimensions of long-term viability. But strategy asks the bigger question: Where are we going, and how will we get there?

Moving from assessment to strategic planning involves essential shifts…..

From Observation to Prioritization

Not every insight becomes a goal. Use the report to identify a handful of key areas that matter most now, whether that’s shoring up leadership alignment, rethinking funding stability, or addressing workforce sustainability.

From Metrics to Meaning

A score is a starting point, not a story. To truly understand what the assessment is revealing, organizations must go beyond the numbers and connect the data to real-world context.

This means:

• Bringing in lived experience: Invite staff, clients, or partners to reflect on what the scores represent in practice. Does a “moderate” score on internal communication reflect information overload, unclear roles, or something else entirely?
• Layering in additional data: Use complementary sources like HR metrics, financial trends, program outcomes, survey results to validate or challenge what the assessment is signaling.
• Understanding nuance: A high score might still mask internal strain. A lower score could reflect growing pains during a period of innovation. Metrics tell you what’s happening and conversation helps you understand why.

When data is paired with experience, reflection, and dialogue, it moves from static evaluation to meaningful insight. And that’s what strategic planning depends on: shared understanding, not just shared documents.

From Reflection to Action

The assessment should shape (not dictate) your strategic plan. Think of it as your organizational health check. The strategy is the fitness plan that follows.

So—What Comes Next?

Wherever you are, coLAB is here to support that next step, whether it’s clarifying priorities, convening stakeholders, or designing a plan that reflects where you are and where you’re ready to go.

• Maybe your organization has just completed a sustainability assessment and is wondering how to act on it.
• Maybe you’re looking to debrief the findings, host a board discussion, or engage staff in interpreting what the results mean.
• Maybe you’ve outgrown your current strategy, or maybe you never had one, and need a facilitated process to chart the next chapter.
• Or maybe you’re just sensing that it’s time for a conversation about what’s next.

Ready to get started?
Begin with a single conversation, a focused domain, and the courage to ask, “What do we want to grow next and what will it take to sustain it?”

So, what makes a report worth revisiting?

When your sustainability report is grounded in real data and rooted in your mission, it becomes more than a reflection, it becomes a launchpad. Done well, these reports surface patterns, spark questions, and give your team a shared language for growth. But only if they’re used.

The ideas below are designed to help you shift from passive insight to active momentum, whether you’re ready to build culture, influence decisions, or reimagine what sustainability looks like in practice.

Twelve Creative Ways to Use Your Sustainability Report

(These aren’t your standard read-and-file strategies.)

• Host a ‘Data Happy Hour.’ Instead of another formal debrief, gather your team around snacks and slides. Let each department or leader share one insight from the report that surprised them, and one idea they’d love to test. Keep it casual and creative: think whiteboards, sticky notes, even music. This makes data approachable and helps spark new perspectives.
• Build a Board Learning Series. Turn each sustainability domain (e.g., leadership, finance, equity, strategy) into a quarterly topic for board learning. Use findings to frame short sessions, inviting guest speakers, community leaders, or even staff to lead discussions. This helps your board deepen its knowledge and become stronger stewards of sustainability.
• Turn Metrics into Murals. Visualize key data points from the report in your office, public spaces, or website. Think infographic posters, timeline walls, or a real-time dashboard in your lobby. Making data visible (and beautiful) helps keep it top of mind and turns abstract indicators into everyday reminders of what matters.
• Launch a ‘From Insight to Action’ Challenge. Challenge each team to pick one domain or score they want to improve, and outline one actionable step they’ll take over the next quarter. Then report back at the next all-staff meeting. You can even gamify it with awards like “Most Creative Pivot” or “Best Bounce-Back Plan.”
• Pitch a Funders-Only Briefing. Use your report to hold a transparent, forward-looking conversation with key funders. Share what you’re learning, where you’re growing, and where you need support. This builds trust, shows readiness, and may unlock funding to strengthen weaker areas.
• Create ‘Mission Muscle’ Awards. Celebrate internal strengths by recognizing teams who are excelling in sustainability areas—like adaptive capacity or cross-team collaboration. These recognitions help reinforce the behaviors that make your mission stick and build momentum toward improvement.
• Layer It with Financials. Overlay your report findings with your budget. Are you underinvesting in critical infrastructure? Are high-performing areas well-resourced? This pairing helps your leadership team and board ensure dollars align with long-term strength not just short-term outputs.
• Invite Your Community to Respond. Share a plain-language summary of the report publicly, via newsletter, town hall, or social media and ask for community input. Which findings resonate? What feels missing? This is a chance to turn transparency into engagement and bring outside voices into your learning process.
• Infuse It into Onboarding. Include a snapshot of the report in your staff or board onboarding materials. This helps new people understand how the organization thinks about sustainability and where it’s focused for the future. It signals that learning, reflection, and improvement are part of your culture.
• Connect It to DEI. Work Look at how your sustainability results intersect with your equity and inclusion goals. Are there patterns in the data that reflect structural inequities? Use the report to frame honest conversations about what’s working—and where deeper shifts are needed.
• Use It to Sunset or Scale. Have a tough program decision coming up? Use your assessment data to guide conversations about what’s ready to scale and what may no longer serve your mission. The report offers a neutral lens for courageous decision-making and resource realignment.
• Reassess Annually, Publicly. reat the sustainability assessment as a living process. Commit to reassessing annually and sharing key takeaways with your community. This builds accountability, shows evolution over time, and reinforces your organization’s commitment to long-term impact.

Closing Thought

Your sustainability report isn’t just a reflection, it’s a toolkit. And when it’s activated creatively, it can unite teams, clarify direction, and catalyze real growth. The ideas above are just a starting point. How will you put your data to work?