Sylke Chesterfield

Leadership coach · Albany, NY · virtual

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Services

ServiceWhat is includedPrice
One-on-One Coaching
busy professionals wanting individualized attention		 creating necessary changes · achieving intended goals on request
Laser Coaching
motivated leaders needing brief, focused coaching		 kick-off planning meeting · brief sessions focused on one topic · support momentum toward next milestone on request
Asynchronous Coaching
busy leaders with erratic schedules comfortable with video communication		 dialog via email messages · brief recorded video messages on request
VIP Day
leaders needing one-time intense focus on objectives		 1 session · half or full day session · strategic plan to implement · conducted in person or via Zoom on request
Group Coaching
leaders thriving in group settings		 topical expertise · group-generated solutions · peer feedback · hot-seat coaching · accountability on request
Mastermind Group
leaders wanting peer strategizing and accountability		 strategizing with peers · developing solutions · accountability 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 LinkedInnononononono
Interviews and offersnononononono
Job search strategynonoyesyesyesyes
Career direction and changenonoyesyesyesyes
Leadershipnonoyesyesyesyes
Personal brandnononononono

How they work

Process
Initial exploratory call to discuss situation and objectives · Create customized roadmap tailored to goals and challenges · Provide actionable strategies · Offer support and accountability
Before coaching
Business Consultant (29 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. Which body issued your credential, and can I check it there? (credential listed)
  4. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

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