Oliver Robinson
Leadership coach · Albany, NY · in person and virtual
"We partner with you to clarify direction, strengthen capacity, and move your organization forward." (in their words, on their website)
Services
| Service | What is included | Price |
|---|---|---|
| New to a Role Coaching Newly appointed leaders, newly promoted administrators, first-year directors and principals |
12 sessions · 52 weeks · Monthly coaching session (virtual) · Email support between sessions (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 coaching session (virtual) · 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 coaching session (virtual) · Change roadmap and communication planning support · Stakeholder mapping and meeting prep · Decision support during critical phases | $12,500 |
| Organizational Optimization Consulting | Specialized educational leadership or executive-level professional development · High-impact strategy or organizational consulting · Fiscal Leadership and Rightsizing · Strategic Planning and Goal Setting · Leadership Development and Succession Planning | $300 |
| Professional Development Consulting | School Board Retreats · Fostering a Culture of Prosperity · Emotional Intelligence and Leadership Resilience · Equity and Inclusive Leadership · Navigating Change and Maintaining Stability | $300 |
| Keynote Speaking | Equity in Opportunities and Outcomes · This is US- Unequivocally Supportive · Organizational Synergy and Reciprocal Responsibility · Cultivating Excellence in Challenging Times | $2,500 |
As published on their website, read Sep 30, 2026.
How they compare
- Their packages start at $6,500. Of the 176 leadership coaches in our directory who publish a package price, 91% start at the same price or lower.
- 30 years coaching; the median for leadership coaches in our directory is 15.
Computed by Callings from the prices and experience coaches publish. Not a rating.
Where they fit
| Students | Early | Mid | Manager | Director | VP / C-suite | |
|---|---|---|---|---|---|---|
| Resume and LinkedIn | no | no | no | no | no | no |
| Interviews and offers | no | no | no | no | no | no |
| Job search strategy | no | no | yes | yes | yes | yes |
| Career direction and change | no | no | yes | yes | yes | yes |
| Leadership | no | no | yes | yes | yes | yes |
| Personal brand | no | no | no | no | no | no |
How they work
- Process
- Initial Assessment · Ongoing Coaching Partnership · Flexibility and Responsiveness · Confidentiality
Do it yourself, or hire a coach?
| Doing it yourself | Usually enough when | A coach earns the fee when | |
|---|---|---|---|
| Job search | A target list, a weekly plan and steady outreach. Callings builds the weekly plan and tracks every application, free. | Interviews are coming in. | Three months without traction, or a senior search that runs on your network. |
| Career direction | Weeks of reading and conversations about roles that fit. Callings can show your strengths and the pay for each role. | You already have two or three target roles. | You do not know what comes next, or you want structure and a formal assessment. |
| Leadership | Peer 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
- If I land a job partway through, what happens to the sessions I have not used? (multi-session package)
- What are your cancellation and refund terms? (no refund terms on their site)
- Who do you usually work with, and how long does a typical engagement last? (always worth asking)
What they publish
- Prices: yes
- What each service includes: yes
- A free consultation: yes
- Refund or cancellation terms: not found on their website
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