Wind + Sail Leadership Partners
Leadership coach · virtual
"Partner with Wind + Sail to develop leaders ready to navigate all waters." (in their words, on their website)
Services
| Service | What is included | Price |
|---|---|---|
| Leadership Coaching Senior through C-Suite leaders across diverse industries, organizational sizes and roles |
24 weeks · structured, collaborative, and highly customized partnership · accelerate leader’s development · create meaningful results for organization · assessments · manager alignment | on request |
| Helm Retreats Executive teams |
team coaching · facilitated dialogue · deepen trust · sharpen strategy · create action plans | on request |
| Mainsail Program Frontline managers and emerging leaders |
6 sessions · six interactive sessions · delivered virtually or in person · research-backed content · tools and templates for immediate use · live format for skill practice | on request |
| Speaking & Special Events Organizations |
customized workshops · master facilitation · memorable and impactful events · energize people · connect teams | on request |
As published on their website, read Sep 30, 2026.
How they compare
- 20 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 | no | no | no | no |
| Career direction and change | no | no | no | no | no | no |
| Leadership | no | no | yes | yes | yes | yes |
| Personal brand | no | no | no | no | no | no |
How they work
- Process
- Set the course: Conduct & review assessments, 360 assessment, Identify coaching engagement goals, Align goals with coaching sponsor · Zoom out & refine: Gather progress feedback, Engage in fieldwork & test new practices, Explore & experiment, Midpoint check-in to review and refine goals, Midpoint sponsor meeting to share progress & solicit feedback · Set sail: Review progress & crystallize learnings, Set next steps for development beyond coaching, Reflect on journey & celebrate successes with coaching sponsor
- Assessments
- 360 assessment, Compass Diagnostic, Leadership Circle Profile, iEQ9 Enneagram, Hogan, MBTI
- Before coaching
- Talent leader, Consulting (Bain & Company); Leadership development and training initiatives leader, Consulting (Bain & Company)
Do it yourself, or hire a coach?
| Doing it yourself | Usually enough when | A coach earns the fee when | |
|---|---|---|---|
| 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
- What does it cost in total, and what is included? (no published price)
- 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: not found on their website
- What each service includes: yes
- A free consultation: not found on their website
- Refund or cancellation terms: not found on their website
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