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Description
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 you'll get from this package
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
Additional details
Coaching delivered via live sessions.
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.
Before the first session, clients will receive a brief set of intake questions through Leland messaging. Please submit your responses at least 48 hours before our scheduled session so I can understand your goals and tailor our conversation accordingly. All three coaching sessions should be completed within 90 days of purchase unless we agree to a different schedule in advance. Sessions may be rescheduled with at least 24 hours’ notice. Sessions canceled or rescheduled with less than 24 hours’ notice may be counted as used, except in the case of an emergency. Between sessions, clients may send brief updates or clarifying questions through Leland. I will generally respond within two business days. Substantive coaching, document review, or additional strategy development may require scheduled coaching time. Coaching is a collaborative process designed to strengthen clarity, decision-making, leadership, and execution. While I am committed to providing thoughtful guidance, practical tools, and actionable support, specific organizational, financial, career, or other outcomes cannot be guaranteed.
Services included:
Decision Making
Strategy
Communication Skills
Strategic Planning
Leadership Development
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
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Jamie also coaches for Non-Profit Leadership and Leadership Coaching. View all.

Offered by Jamie J.
Joined July 2026
State Legislator & Former COO | Helping Leaders Execute Strategy
I bring more than 13 years of leadership experience across nonprofit organizations, government, healthcare, behavioral health, and criminal justice. As a former Chief Operating Officer, I partnered with CEOs and boards, directed enterprise functions, led organizational change, developed leaders, and translated strategic priorities into operational execution. My broader executive experience includes responsibility for 16 programs across five states, more than 350 employees, and approximately $20 million in operations. Today, as a Colorado state legislator, I make consequential decisions, lead complex policy discussions, and build coalitions among stakeholders with competing priorities. I understand the realities executives face: limited time and resources, difficult personnel decisions, organizational change, public accountability, and the expectation that they will provide clarity even when the path forward is uncertain. Drawing on this experience and my master’s degree in Organizational Leadership and Human Resource Management, I help executives strengthen their judgment, align and motivate their teams, navigate difficult challenges, and move strategy into effective execution.
$509.25
3h of coaching