Wayne Kessler

Career coach · Boston, MA · virtual

"The mission of Boston Business Coaching is serve as a catalyst for optimal personal and organizational success and career fulfillment." (in their words, on their website)

Services

ServiceWhat is includedPrice
Career Safari 4-Session Career Coaching Package
career or job seeker fairly certain of career path
4 sessions · 4 weeks · 60-90 minute Discovery career coaching session · Myers-Briggs Personality Assessment with detailed report · Coaching sessions to review personality inventory results · Strong Interest Inventory Career Assessment with detailed report · Coaching sessions to review Strong Interest Inventory results $995
Career Safari 8-Week Career Coaching Package
career or job seeker without clear career idea
8 weeks · 60-90 minute Discovery career coaching session · Myers-Briggs Personality Assessment with detailed report · Weekly coaching sessions to review personality inventory results · Strong Interest Inventory Career Assessment with detailed report · Coaching sessions to review Strong Interest Inventory results $895
ADD/ADHD Coaching
people with ADHD and ADD
Education and empowerment about ADHD/ADD · Building on unique strengths · Addressing challenges · Planning and managing time better · Getting more organized and structured on request
Executive and Business Coaching
executives and business professionals
Growth challenges · Getting along better with others · Managing emotions · Leadership development · Delegation on request
Career Coaching and Job Acquisition
people exploring/changing careers or job search
Exploring/changing careers · Workplace adjustment · Human resource/challenging work issues · Job search · Promotions on request
Coach for College Students
college students
Adjusting to life at school and away from home · Providing coaching support and structure · Meetings in person and over Skype as needed on request
College Student Job Coaching Services
college students
Resume and cover letter writing or revision · Exploring and completing applications in job search sites · Learning to work with job finding services · Planning job search strategies · Negotiating salary offers on request
Life Coaching
people seeking balance in life areas
Work · Finances · Fitness/health · Career · Family on request
Marketing Coaching
new or prospective business owners
Branding · Website Development · Search Engine Optimization · Conversion · Tracking on request
Peak Performance Coaching
people needing guidance to next level in business, life, sport
Guidance and support to next level on request

As published on their website, read Sep 30, 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 LinkedInnoyesyesyesyesyes
Interviews and offersnoyesyesyesyesyes
Job search strategynoyesyesyesyesyes
Career direction and changenoyesyesyesyesyes
Leadershipnoyesyesyesyesyes
Personal brandnoyesyesyesyesyes

How they work

Process
Assessment of coaching needs/challenges · Exploring strengths and successes · Understanding barriers to success · Exploring tools/strategies · Co-creating short and long term goals · Prioritizing goals and setting time-frames
Assessments
Myers-Briggs Personality Assessment, Strong Interest Inventory
Before coaching
licensed therapist (10 years)

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Resume4 to 8 hours for a strong base, then about 30 minutes per posting. Callings can tailor it to each job.You are staying in the same field and level and have recent results to cite.You are changing field or level, coming back after a long break, or many applications brought no interviews.
Interviews3 to 6 hours of practice out loud per interview process. Callings can prepare you for each job you track.Early rounds in a format you know.Final rounds, panels, a new kind of role, or you tend to freeze.
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.

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. Which body issued your credential, and can I check it there? (credential listed)
  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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