From Strategy to Execution: Executive Coaching Sprint
This focused three-session coaching engagement is designed for executives and senior leaders who need to move an important priority, decision, or organizational challenge forward. Rather than offering generic leadership advice, we will examine your specific situation, identify the central obstacles, and develop a practical strategy for effective execution. Before our first session, you will receive a brief set of intake questions through Leland messaging covering your objective, current challenges, key stakeholders, and desired outcome. Session 1 — Clarify the Challenge We will assess your current situation, define the outcome you want to achieve, identify the most important barrier, and establish clear measures of progress. Session 2 — Develop the Strategy We will evaluate options, examine risks and competing priorities, identify the people who must be engaged, and determine the decisions and actions needed to move forward. Session 3 — Build the Execution Plan We will translate the strategy into a focused action plan with priorities, milestones, accountability measures, and a communication approach for engaging key stakeholders. Throughout the engagement, you will receive candid, strategic, and supportive coaching grounded in real executive and organizational leadership experience. Each session will conclude with concrete next steps that you can apply immediately.
What's included
This package includes three private, 60-minute coaching sessions delivered by video over approximately four to six weeks. Sessions are typically scheduled one to two weeks apart so you have time to apply what we discuss, evaluate progress, and bring new insights or obstacles into the next conversation. My approach is candid, strategic, supportive, and action-oriented. I will ask thoughtful questions, challenge assumptions when needed, and help you connect leadership decisions with the people, systems, and organizational realities that affect execution. This is a collaborative process: you bring your knowledge of the organization and its mission, and I provide an objective executive perspective, a structured process, and practical tools to help you move forward.
- A clearly defined leadership or organizational objective with measures of progress
- A prioritized assessment of the primary barriers, risks, and opportunities
- A practical approach for engaging and communicating with key stakeholders
- A collaboratively developed 30-60-90-day execution roadmap
- Clear priorities, next steps, ownership, and accountability measures
- Greater clarity and confidence in moving the strategy forward
Meet your expert
Jamie J.
State Legislator & Former COO | Helping Leaders Execute Strategy
Leadership is most challenging when the mission matters, resources are constrained, stakeholders have competing priorities, and people are looking to you to provide a clear path forward. I help executives and emerging leaders translate strategy into effective execution by aligning people, priorities, and organizational systems. My work is grounded in a central belief: a strategic plan only creates value when leaders can mobilize their workforce, establish accountability, and turn complex goals into coordinated action. I bring more than 13 years of leadership experience across nonprofit organizations, government, healthcare, behavioral health, and criminal justice. As a former nonprofit Chief Operating Officer, I directed enterprise functions spanning finance, human resources, technology, communications, development, compliance, and administration. Earlier in my career, I led approximately $20 million in multi-state operations encompassing 16 programs and more than 350 employees. Today, I serve as a Colorado state legislator representing approximately 90,000 constituents in one of the state’s most diverse communities. My work requires me to build coalitions among people with competing interests, communicate complex ideas clearly, make consequential decisions under public scrutiny, and move policy from concept toward implementation. That combination of executive, operational, and public leadership shapes how I coach. I do not offer generic leadership advice. I help clients identify the real obstacle, examine it honestly, develop a practical strategy, and determine how to engage their people to carry it forward. I am especially equipped to help leaders: • Translate strategic priorities into focused action • Align and develop teams around a shared direction • Navigate organizational growth, change, and uncertainty • Strengthen executive judgment, presence, and communication • Manage complex relationships with boards, CEOs, funders, agencies, and community stakeholders • Build greater accountability across people, processes, and performance • Prepare for an executive role or expanded leadership responsibility My coaching style is candid, strategic, supportive, and action-oriented. Clients leave our work with greater clarity, stronger leadership tools, and concrete next steps they can apply immediately. If you are carrying a complex leadership challenge, or know that your organization needs more than another plan, I can help you connect strategy, people, and execution to move the work forward.
