Crosswind Approach

Michael Baldree
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  • NON-PROFIT
  • UPDATED WEEKLY

The Crosswind Approach is a leadership podcast for nonprofit and mission-driven organizations. Hosted by Michael Baldree, the show features conversations with leaders who have navigated organizational turbulence while staying grounded in their mission. Each episode offers practical insight for leaders seeking clarity, resilience, and confident decision-making.

Episodes

  1. 1D AGO

    Episode 04: Lessons from a Nonprofit Founder

    Episode Overview What does an exploding engine at 41,000 feet have to do with nonprofit leadership? In this episode of The Crosswind Approach, Michael Baldree, CPA and founder of Crosswind CFO Advisory, shares the story of Qantas Flight 32 and the leadership decision that saved 469 lives. He connects that aviation story to one of the most important lessons nonprofit founders must learn: stop focusing only on what is broken and lead from what is still working. Michael is joined by Megan Moon, founder and former president of the Humane Education Coalition, a nonprofit she built from the ground up and scaled across 30 countries before guiding it through a successful acquisition. Together, they discuss nonprofit startup realities, founder burnout, revenue diversification, leadership legitimacy, succession planning, and what it takes to build sustainable organizations that outlast their founders. If you are a nonprofit founder or mission-driven leader navigating growth, uncertainty, or organizational pressure, this episode will help you lead with greater clarity, resilience, and long-term perspective. Key Takeaways - Vision alone does not sustain organizational growth - Revenue diversification protects long-term stability - Mission alignment matters when pursuing funding - Founder habits can become growth bottlenecks - Delegation and systems are essential for scaling - Legitimacy requires standards, structure, and credibility - Succession planning is a stewardship responsibility - Turbulence is not the same thing as failure Crosswind Checklist 1. Diversify your revenue sources to reduce funding risk 2. Build and protect three to six months of operating reserves 3. Review financial statements and budget performance every month Timestamps 00:00 – Welcome to The Crosswind Approach and podcast overview 00:48 – The aviation story: Qantas Flight 32 03:09 – Leading from what is still working 05:31 – Introduction to guest Megan Moon 07:46 – Embarrassing moments in nonprofit leadership 10:07 – The tipping point that led to founding HEC 12:28 – Revenue diversification and funding strategy 17:12 – Founder burnout and leadership bottlenecks 19:33 – Delegation, systems, and sustainable scaling 21:56 – Building legitimacy and credibility in a nonprofit sector 24:15 – Succession planning and organizational stewardship 26:38 – Separating identity from leadership roles 29:04 – Common blind spots nonprofit leaders face 31:24 – Why turbulence is not failure 33:45 – Advice for overwhelmed nonprofit leaders 35:59 – Crosswind Checklist financial best practices 38:20 – Final thoughts and call to action Connect: Connect with Michael on LinkedIn: https://www.linkedin.com/in/michaelbaldree/ Connect with Megan on LinkedIn: https://www.linkedin.com/in/megansmoon/ Subscribe and Share If you found this episode helpful: - Follow The Crosswind Approach so you do not miss future episodes - Share it with another nonprofit or mission driven leader - Leave a quick review to help others discover the show

    39 min

  2. APR 29

    How to Avoid a Crash Disaster During Leadership and System Changes

    Episode Overview What do a runway decision and nonprofit leadership have in common? In this episode of The Crosswind Approach, Michael Baldree, CPA and founder of Crosswind CFO Advisory, shares the story of Air Canada Flight 143, known as the Gimli Glider, and connects it to one of the most critical realities nonprofit leaders face: the decisions made before a leadership transition or system change ever takes off. Michael is joined by Ruth Thomas, Vice President of Finance and Administration at SAT-7 USA, who brings over 20 years of experience leading through leadership transitions and major operational changes. Together, they explore what it takes to successfully navigate leadership onboarding, CRM migrations, and financial system changes without creating downstream disruption. If you are a nonprofit leader preparing for a leadership transition or considering a major operational change, this episode will help you think more proactively and lead with greater clarity and control. Key Takeaways - Most failures begin before execution, not duringLeadership transitions require proactive financial clarity - Early alignment reduces long-term disruptionOperational changes take longer than expected - Systems must evolve to support organizational growth - Data accuracy is critical to maintaining donor trust - Preparation prevents downstream chaos - Strong processes create long-term efficiency Crosswind Checklist 1. Review your budget against actuals every month 2. Build a cash reserve of 60 to 90 days of operating expenses 3. Know your Form 990 and ensure it reflects your organization accurately Timestamps 00:00 – Welcome to The Crosswind Approach and podcast overview 01:00 – The aviation story: The Gimli Glider 03:30 – How failures begin before takeoff 05:30 – Introduction to guest Ruth Thomas 07:30 – Financial risks during leadership transitions 10:00 – Building a strong onboarding process for new leaders 13:00 – Adapting to new leadership styles 16:00 – Using team feedback and culture surveys 18:30 – Operational change: moving to a caging system 22:00 – Challenges during COVID and process breakdowns 25:00 – Managing donor communication and address changes 28:00 – Fixing data and operational inefficiencies 31:00 – Efficiency gains and improved controls 34:00 – Lessons learned from system transitions 37:00 – CRM migration challenges and decisions 41:00 – Balancing cost, usability, and scalability 44:00 – Most demanding leadership challenges 46:00 – Advice for leaders navigating change 48:30 – Crosswind Checklist financial best practices 50:30 – Final thoughts and call to action Connect: Connect with Michael on LinkedIn: https://www.linkedin.com/in/michaelbaldree/ Connect with Ruth on LinkedIn: https://www.linkedin.com/in/ruththomas88/ Subscribe and Share If you found this episode helpful: - Follow The Crosswind Approach so you do not miss future episodes - Share it with another nonprofit or mission driven leader - Leave a quick review to help others discover the show

    38 min

  3. APR 15

    How to Avoid People/Culture Crash Disaster

    Episode Overview What do a “dual engine failure” and nonprofit leadership have in common? In this episode of The Crosswind Approach, Michael Baldree, CPA and founder of Crosswind CFO Advisory, revisits the story of US Airways Flight 1549, the Miracle on the Hudson, and connects it to one of the most critical realities nonprofit leaders face: making high-stakes decisions in moments of uncertainty. Michael is joined by Paul Welch, a seasoned leader with over 20 years of experience across nonprofit, ministry, and fintech organizations. Together, they explore what it takes to lead through team disruption, culture challenges, and unexpected change, especially when key people leave and uncertainty rises across the organization. If you are a nonprofit leader navigating staffing challenges, cultural misalignment, or organizational uncertainty, this episode will help you lead with greater clarity, awareness, and confidence. Key Takeaways - Crisis reveals the depth of your preparation - People are the core of organizational resilience - Your greatest strength can also be your weakness - Culture is built through actions, not aspirations - Transparency builds trust - Awareness is a leadership multiplier - Healthy teams balance results and relationships - Clarity and prioritization drive action in crisis Crosswind Checklist 1. Know exactly where every dollar is going and why 2. Track and clearly distinguish restricted vs. unrestricted funds 3. Run a monthly budget to actual review Timestamps 00:00 – Welcome to The Crosswind Approach and podcast overview 00:48 – The aviation story: Miracle on the Hudson 03:12 – Leadership lessons from Captain Sully 05:36 – Introduction to guest Paul Welch 07:58 – Losing a key team member and team disruption 10:26 – Early warning signs leaders often miss 12:53 – When strengths become blind spots 15:19 – Reflection as a leadership discipline 17:42 – Communication challenges in nonprofit leadership 20:08 – Why people must come before tasks 24:56 – Values vs. aspirational values in culture 29:35 – Understanding your team through people profiles 32:00 – Trust, transparency, and psychological safety 36:43 – How to assess team health and dynamics 41:09 – Communication habits that build trust 43:29 – The importance of self-awareness in leadership 45:45 – What to do when a key team member leaves 48:08 – How to connect with Paul Welch 50:33 – Crosswind Checklist financial best practices 53:00 – Final thoughts and call to action Connect Connect with Michael on LinkedIn: https://www.linkedin.com/in/michaelbaldree/ Connect with Paul on LinkedIn: https://www.linkedin.com/in/paul-welch-49379430/ Subscribe and Share If you found this episode helpful: - Follow The Crosswind Approach so you do not miss future episodes - Share it with another nonprofit or mission driven leader - Leave a quick review to help others discover the show

    54 min

  4. APR 1

    How to Avoid Operation Crash Disaster

    Episode Overview What do a catastrophic aviation failure and nonprofit leadership have in common? In this first episode of The Crosswind Approach, Michael Baldree, CPA and founder of Crosswind CFO, shares the powerful story of United Airlines Flight 232 and connects it to one of the most important realities nonprofit leaders face: navigating uncertainty with limited visibility. Michael is joined by Leon Blalock, Executive Director of Christian Life Center and a seasoned leader with over 35 years of experience across nonprofit and for-profit organizations. Together, they explore what it really takes to lead through crisis, from communication and decision-making to financial clarity and team alignment. If you’re a nonprofit leader facing cash flow uncertainty, board pressure, or operational challenges, this episode will help you think more clearly and lead more confidently. Key Takeaways - Crisis reveals leadership - Clear and consistent communication builds trust - You don’t need perfect data to make good decisions - You don’t have to have all the answers - Proactive systems prevent reactive chaos - Dashboards and financial visibility are essential - Action beats indecision - Crosswind Checklist - Create a rolling 90-day cash flow forecast - Use a one-page financial dashboard - Define your reserve strategy Timestamps 00:00 – Welcome to The Crosswind Approach and podcast overview 01:00 – The aviation story: United Airlines Flight 232 02:20 – Connecting aviation failure to nonprofit leadership challenges 03:00 – Introduction to guest Leon Blaylock 04:30 – Real-world crisis: ATM system failure across a national network 07:00 – Identifying the problem and building a response plan 08:30 – The power of clear, consistent communication during crisis 10:30 – Early warning signs and how to catch issues sooner 12:00 – Building proactive systems and team involvement 14:00 – How to make decisions with limited information 16:30 – Why leaders must rely on experience, experts, and teams 18:30 – Communicating with boards during uncertainty 21:00 – Team alignment, leadership rhythms, and preparation habits 23:30 – Advice for leaders currently navigating turbulence 25:30 – Key operational levers and financial dashboards 26:00 – Crosswind Checklist: 3 habits for financial clarity 27:00 – Final thoughts and call to action Connect with Michael Connect with Michael on LinkedIn: https://www.linkedin.com/in/michaelbaldree/ Subscribe & Share If you found this episode helpful: - Follow The Crosswind Approach so you don’t miss future episodes - Share it with another nonprofit or mission-driven leader - Leave a quick review to help others discover the show

    29 min

  5. MAR 16

    Crosswind Approach Trailer

    The Crosswind Approach is a leadership podcast for nonprofit and mission-driven organizations. Hosted by Michael Baldree, the show features conversations with leaders who have navigated organizational turbulence while staying grounded in their mission. Each episode offers practical insight for leaders seeking clarity, resilience, and confident decision-making.

  • 5 Episodes

About

The Crosswind Approach is a leadership podcast for nonprofit and mission-driven organizations. Hosted by Michael Baldree, the show features conversations with leaders who have navigated organizational turbulence while staying grounded in their mission. Each episode offers practical insight for leaders seeking clarity, resilience, and confident decision-making.

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