Jon Macaskill

Leadership coach · virtual

"I specialize in helping individuals and organizations build emotional resilience, cultivate grit, and lead with compassion and clarity." (in their words, on their website)

Services

ServiceWhat is includedPrice
Executive, Health, and Performance Coaching
leaders and high performers
in-depth assessment of goals, challenges, health baseline, and leadership context · custom coaching plan · assessments and feedback tools · weekly or bi-weekly coaching sessions (virtual or in-person) · practical exercises and action steps between sessions on request
Organizational Consulting
organizations
culture alignment · leadership development · building talent pipelines · wellness and resilience systems · assessments on request
Leadership Workshops
leadership teams, offsites, culture resets
1 session · interactive dialogue · practical tools · real-world application · half-day and full-day formats on request
Meditation Courses & Retreats
leaders and teams
in-person retreats · online courses · skills to reset · tools to carry mindfulness into daily life on request
Keynote Speaking
corporate teams, leadership groups, large conferences
1 session · customized presentations · personal stories · actionable strategies · science-backed insights on request

As published on their website, read Sep 30, 2026.

Where they fit

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

How they work

Process
in-depth assessment of goals, challenges, health baseline, and leadership context · design coaching plan · conduct coaching sessions · assign practical exercises and action steps · provide ongoing accountability and support
Before coaching
Navy SEAL Commander, military special operations (24 years)

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Job searchA 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 directionWeeks 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.
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. What does it cost in total, and what is included? (no published price)
  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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