Tom Doolittle

Executive coach · South Glastonbury, CT · in person and virtual

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"My expertise is helping senior leaders improve the structure, communication, collaboration, and governance across teams, so their organizations reduce inefficiency costs and increase margins." (in their words, on their website)

Services

ServiceWhat is includedPrice
Advisory Change strategy and communications system · Leader behaviors and meeting and decision rhythms · Team performance, trust, clarity, commitments, and problem resolution on request
Leadership Intensives Executive alignment, operating model, and governance · Leader-as-teacher mastery through teach-back delivery on request
Skill Building Leader, manager, and coaching skills · Team-level coaching on feedback, coaching cadence, and growth conversations on request
Speaking / Keynotes Keynotes on silo friction, AI collaboration, and manager behaviors on request
Executive Coaching
Senior leaders		 Discussions about how leaders show up, use their strengths, and what holds them back from their goals on request
Succession Planning Services and Training Program
Organizations		 Support for employee lifecycle planning · Implementation of 9 Box Scoring · Training senior managers in 9 Box Scoring on request
Solving The Big Problems
Senior leaders, VP and middle management, cross-silo team members, and external stakeholders such as customers		 Wiley's 5 Behaviors of Cohesive Teams assessment and content delivery · Appreciative Inquiry 4D cycle tailored to the organization, department, or team · Workshop to envision a future or solve a significant challenge · Design of improvement prototypes · Action plans with dates and team member accountability on request
Getting Your Teams to Work Like A Team
Newly formed or intact teams		 Team development learning journey modules · Everything DiSC · 5 Behaviors of a Cohesive Team · Clifton Strength Assessment and Team Mapping · Working Genius on request
CEO Coaching
CEOs		 Identify strengths, weaknesses, and organizational purpose, mission, and goals · Assessments and targeted feedback · Tailored coaching plan · Confidential coaching sessions · Practical strategies on request

As published on their website, read Nov 8, 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
Complimentary 20-minute Friction Scan Chat to identify sources, costs, and root causes of cross-silo friction · Receive a Friction Tax Estimate, Hotspot Hypothesis, and Diagnostic Scope Memo within 48 hours · Conduct a Cross-Silo Friction Diagnostic and develop a pilot plan with leaders and managers · Develop and install best-practice routines, operating rhythms, decision rights, escalation pathways, incentives, and coaching · Track friction change metrics during the rapid pilot
Assessments
Team Dynamics, AI Fluency Testing, AI Utilization Baselines, Leader Feedback Compass Mapping, Wiley's 5 Behaviors of Cohesive Teams Assessment, Everything DiSC

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. 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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