Oliver Robinson

Executive coach · Albany, NY · in person and virtual

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"Support for school superintendents, district leaders, boards, and educational professionals navigating complexity with confidence." (in their words, on their website)

Services

ServiceWhat is includedPrice
New to a Role Coaching
Newly appointed leaders, newly promoted administrators, first-year directors and principals		 12 sessions · 52 weeks · Monthly virtual coaching session · Email support between sessions on business days · 12-month action plan and progress tracking · Tools for priorities, meetings, and communication $6,500
Performance Improvement Coaching
Leaders strengthening execution, communication, leadership habits, and results		 12 sessions · 52 weeks · Monthly virtual coaching session · Performance goals and milestone plan · Accountability tracking and structured debriefs · Support for difficult conversations and time prioritization $10,500
Organizational Change Coaching
Leaders driving strategic change, culture shifts, redesigns, and high-visibility initiatives		 12 sessions · 52 weeks · Monthly virtual coaching session · Change roadmap and communication planning support · Stakeholder mapping and meeting prep · Decision support during critical phases $12,500
Additional coaching sessions on request
On-site coaching days on request
Assessments on request
Leadership team coaching
Leadership teams		 on request
Organizational Optimization Consulting
Educational organizations and executive-level clients		 Specialized educational leadership or executive-level professional development · High-impact strategy or organizational consulting · Projects may include fiscal leadership and rightsizing, strategic planning and goal setting, leadership development and succession planning $300
Organizational Optimization Consulting (virtual)
Educational organizations and executive-level clients		 Specialized educational leadership or executive-level professional development · High-impact strategy or organizational consulting · Projects may include fiscal leadership and rightsizing, strategic planning and goal setting, leadership development and succession planning $175
Professional Development School board retreats · Fostering a culture of prosperity · Emotional intelligence and leadership resilience · Equity and inclusive leadership · Navigating change and maintaining stability $300

As published on their website, read Nov 6, 2026.

How they compare

Computed by Callings from the prices and experience coaches publish. Not a rating.

Where they fit

StudentsEarlyMidManagerDirectorVP / C-suite
Resume and LinkedInnononononono
Interviews and offersnononononono
Job search strategynononononono
Career direction and changenononononono
Leadershipnonoyesyesyesyes
Personal brandnononononono

How they work

Process
Initial assessment: discuss what prompted coaching, current circumstances, goals, and the best coaching approach · Ongoing coaching partnership: regular sessions, typically monthly, over 6–12 months · Flexibility and responsiveness: adjust plans as circumstances or priorities change · Confidentiality
Before coaching
Superintendent of Schools, Education (25 years)

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
LeadershipPeer groups, feedback from your manager, reading.You have a mentor who has done the job.A first management role or a bigger team, often paid for by the employer.

Times are our estimates. Try Callings.

Questions to ask before hiring

  1. If I land a job partway through, what happens to the sessions I have not used? (multi-session package)
  2. What are your cancellation and refund terms? (no refund terms on their site)
  3. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

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