Professional Development Day: Where Strategy Encounters Reality: Discipline for Strategic Execution

Where Strategy Encounters Reality: Discipline for Strategic Execution

Date:  October 3, 2026

Time:  0800 - 1:30pm

Location: Endeavor's Center

Meal: Continental breakfast and Lunch is included. 

Description

The prior session on Strategic Portfolio Management explores the question: Which work matters most?

This workshop focuses on what happens after execution begins—when organizations struggle to maintain alignment, accountability, decision clarity, and coordinated movement under pressure. Together, participants will examine the more difficult operational question:

Why does the right work still fail to move?

The workshop is structured around three progressive waves of strategic drift:

• Wave 1: Where Execution Begins Losing Clarity
• Wave 2: Where Accountability Breaks Down
• Wave 3: Executive Discussions

Each wave combines facilitated table discussions, audience reflection, operational analysis, and candid conversations around the organizational challenges participants are currently navigating within their own environments.

The session focuses on how teams maintain alignment once ambiguity, competing direction, delivery pressure, and cross-functional friction begin impacting execution. Participants will leave with practical approaches for improving decision clarity, strengthening accountability across teams, surfacing tradeoffs earlier, and keeping work coordinated as conditions continue to evolve.

Duration

4.5 Hours

Talent Triangle

Power Skills / Business Acumen

Agenda

• Registration and Networking
• Workshop Introduction and Strategic Framing
• Wave 1: Where Execution Begins Losing Clarity
• Break and Networking
• Wave 2: Where Accountability Breaks Down
• Wave 3: Executive Discussions
• Lunch and Networking
• Strategic Outcomes and Adaptive Portfolios
• Final Reflection Activity
• Workshop Close

Learning Objectives

• Examine how ambiguity, competing priorities, and delivery pressure begin affecting execution once strategic work enters delivery.
• Evaluate how decision clarity, accountability, and ownership influence coordinated execution under pressure.
• Apply practical approaches for improving alignment, surfacing tradeoffs earlier, and strengthening accountability across teams.

Speaker Biography

Christopher D. Gentry is the Founder and Principal Consultant of StrategyPMO, specializing in strategic execution, portfolio governance, and enterprise transformation. With nearly 20 years of experience, he has supported Fortune 500 companies and state and federal government organizations through modernization, transformation, and complex cross-functional initiatives.

Christopher is a speaker, academic instructor, author, PMI PMP/CAPM Study Hall contributor, and former PMI chapter officer and board member.