The Curious Yes
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Show Notes
In this episode of Wear Your Cape to Work, we talk with Ashley Simmons, VP of PMO at Summit 7, about PMO leadership, stakeholder management, organizational strategy, and leading change with curiosity. Trina first heard Ashley speak on a panel at PMO UnCon in San Diego in the spring of 2026, and what stood out to me right away was her tremendous talent for stakeholder management, organizational strategy, and change.
In this episode, “The Curious Yes,” Ashley shares how she developed that strength across her career, from project specialist to PMO executive, and how some of the mindset behind it started even earlier, back when she was playing national team soccer. This conversation is especially valuable for project managers, PMO leaders, and business leaders who want to build trust, support executive decision-making, and drive business value.
In This Episode, We Talk About:
How PMO leaders can drive value instead of only proving value
How project leaders build bridges between different executives
Why stakeholder management is a strategic PMO skill
How curiosity helps project managers find and fill business gaps
Why a “curious yes” can be more powerful than an automatic no
How “if this, then that” thinking helps executives understand tradeoffs
Why business acumen matters for project and PMO leaders
How mentors, coaches, and feedback can shape your next leadership talent
Chapters00:00 | Intro
01:20 | PMO UnCon Spring 2026: Driving Value as a PMO vs. Proving Value
03:00 | How PMO Leaders Build Bridges Between Different Executives
05:27 | The Many Ways a PM Leader Can Drive Priorities for the Business
06:46 | The Contagiousness of Providing Value to the Executive Team
10:19 | Don’t Put Yourself in a Box: Be Strategic and Forward Looking
11:49 | How Do You Move Up the Ladder and Build a Closer Connection With the C-Suite?
16:18 | Be Curious: Find Out What’s Missing and How You Can Fill the Gap
18:23 | The “Curious Yes”: Not Saying No Too Quickly
20:11 | Using “If This, Then That” to Show Tradeoffs for Executive Decisions
22:12 | Why Net-New Projects Are Often Rocky and What Lessons Learned Can Teach Us
23:00 | The Value of Project Management Services and Why Some Successful Projects Fail
24:56 | Running Projects Differently for Different Stakeholders
25:37 | Why Not Being Curious Can Become a Project Risk
26:38 | Do an MBA and Other Certifications Impact Your Project Career?
28:00 | Learning Your Company’s Business Acumen, Goals, Mission, and Why Behind the Work
29:56 | Innate Project Talents: What Are You Born With That You Bring Into Project Management?
33:00 | How a Coach or Mentor Can Help You See Weaknesses and Grow Your Career
34:25 | The Things We Need to Learn Can Become Our Next Great Talent
About Wear Your Cape to Work
Wear Your Cape to Work is a podcast from Project Insight celebrating the real strengths, talents, and superpowers project leaders bring to their teams, organizations, and careers.
Related Topics
PMO leadership, stakeholder management, project management, organizational strategy, change leadership, executive decision-making, business acumen, project leadership, PMO value, project manager career growth
Project Insight is project and portfolio management software for growing organizations that need better visibility across projects, teams, resources, and strategic priorities. Learn more about how Project Insight helps PMOs and project teams connect work across the organization: https://projectinsight.com