Doug Diamond is smiling and talking to an older woman with gray hair in an office setting.

Build alignment.
Strengthen execution.
Prepare for what’s next.

Coaching Programs for Every Stage of Growth.


Every leadership team is at a different stage in its planning journey. Some are just starting out, some are building momentum, and others are refining strategy for the future. That’s why I offer different levels of coaching — designed to meet you where you are today and guide you toward the company you want to become.

Schedule a Discovery Call to get started.

Coaching Programs & Opportunities

  • A geometric heart shape composed of blue and white squares on a black background.

    Level 1: Planning Foundations

    Establish a reliable rhythm of annual and quarterly planning that keeps your team focused, aligned, and accountable. Through guided sessions and structured tools, you’ll turn goals into action and create lasting momentum.
    Learn more

  • A heart shape made out of small squares in shades of blue and white on a black background.

    Level 2: Strategic Council

    Take your planning further with dedicated time each month to think beyond execution. The Strategic Council helps your leadership team refine strategy, strengthen alignment, and build a confident path for long-term growth.
    Learn More

  • A graphic of 12 blue and white squares arranged in a diamond shape on a black background.

    Level 3: Custom Coaching

    For CEOs ready for deeper insight and direct coaching. Build on your team’s planning and strategy work with one-on-one sessions focused on leadership, complex decisions, and sustaining growth at the highest level.
    Learn More

  • A colorful Rubik's Cube logo with nine squares in blue, cyan, yellow, orange, purple, red, white, dark blue, and dark orange, arranged in a diamond shape.

    Rotating Coaching Opportunities

    Offered at select times throughout the year, these programs help leadership teams align and take action. Each session is designed to create momentum, strengthen focus, and keep your business moving forward with purpose.
    Learn More

Doug Diamond is standing and speaking to a group of people seated at a table in a conference room. The seated individuals are working on laptops. There is a whiteboard and a poster with handwritten notes and sticky notes in the background.

Level 1: Foundations

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Level 1: Planning Foundations — $7,500

For leadership teams ready to establish a reliable planning rhythm.

Great companies aren’t built on ideas alone — they’re built on the ability to stay focused and follow through. In this program, I work with your team to create a rhythm of annual and quarterly planning that keeps everyone aligned, accountable, and confident about moving forward together.

What you get:

  • Structured annual and quarterly planning sessions

  • Twice-per-month 1-hour coaching calls

  • Access to the Planning Workbook in Excel (updated monthly)

  • Clear accountability and progress tracking

Planning Foundations is best for teams new to business planning or those struggling to keep plans alive.

A man in glasses and a light blue shirt is writing on a sticky note board on a tablet screen, with options labeled for quarterly process steps. A coffee cup is blurred in the background.

Level 2: Strategic Council

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Level 2: Strategic Council — $15,000

Already in Level 1? Upgrade for an additional $7,500/year

For leadership teams ready to scale and think long-term.

Once the basics of disciplined planning are in place, it’s time to look further ahead. The Strategic Council builds on the foundation of Level 1, giving you everything in Planning Foundations plus dedicated time each month to stretch your thinking and connect today’s execution to tomorrow’s vision.

Together, we’ll refine your planning process, strengthen alignment, and prepare your company for confident, sustainable growth.

What you get (in addition to Level 1):

  • Monthly 2-hour Strategic Council sessions

  • Frameworks for long-term vision, core values, and strategic thinking 

  • Guidance on scaling, core client development, and growth strategy that drives the development of a 3 year plan.

The Strategic Council is best for teams who are already executing well and want to maximize growth and sharpen long-term strategy.

Level 3: Custom Coaching

A person holding a laptop displaying a website about building alignment, strengthening execution, and preparing for the next stage, in an office setting. The desk has potted plants, a pair of glasses, pens, and a notebook.
A geometric logo design consisting of 13 squares in various shades of blue and light gray, arranged in a diamond formation with black backgrounds.

Level 3: Strategic Council + Custom Coaching — Invite only

For CEOs and leadership teams who want deeper, individualized coaching to accelerate growth.

Where the Strategic Council focuses on long-term strategy, this level adds personalized coaching and support to help you scale faster and execute with greater focus.

Doug works directly with the CEO and leadership team to bring clarity, accountability, and external perspective to your company’s most important decisions. Each month, the CEO receives a dedicated one-on-one coaching session, and Doug joins the leadership team for the first 2.5 hours of their quarterly planning sessions.

Together, you’ll strengthen execution, sharpen priorities, and ensure every quarter builds measurable progress toward your goals.

What you get:

  • Quarterly facilitated sessions with Doug

  • Monthly one-on-one coaching for the CEO

  • External perspective, accountability, and alignment across the leadership team

Strategic Council + Custom Coaching is invite-only for CEOs and leadership teams seeking individualized coaching and accelerated growth.

Jerry, CEO of Synchronet.png

The key benefit for me is structure. With life as crazy as it is, the program keeps us in our planning rhythms, so we always have a quarterly plan that we're working on that connects to our annual plan, and our annual plan connects to where we're trying to get in the next 3-5 years.

Jerry Sheehan, President of Synchronet

Not Sure Where to Start?

Every company is at a different stage. If you’re unsure which program fits, let’s talk it through.

Rotating Coaching Opportunities

Free 2 Hour Annual Planning Session for 2026.

Plan With Confidence.
Lead With Clarity in 2026.

Every business sets goals.
The difference is whether those goals are clear, aligned, and actionable.

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Culture to Action

Available twice a year: following each Culture & Engagement Survey (Q1 and Q3).

Turning survey results into action is where real progress begins. In this workshop, we work with your leadership team to translate insights from the Culture & Engagement Survey into a clear action plan that strengthens trust, alignment, and performance across your organization.
Want to learn more about the survey before next time? Check out how it works.

Join the mailing list and we will let you know when our next survey is ready!