Sylke Chesterfield

business consultant
& executive advisor

Lead with Clarity • Execute with Confidence • Grow with Purpose

Lead with Clarity.
Execute with Confidence.
Grow with Purpose

A Sampling of client Testimonials


In the age of AI, 'co-pilot' is a term we hear a lot. It’s also the first word that comes to mind when I think of Sylke. Over the years, I’ve had the privilege of working with her during three different leadership roles across distinct organizations. Her guidance has not only kept me on course but has also elevated my leadership skills to entirely new levels. Missing even one week of our sessions feels like losing my compass—her insights are that vital to staying aligned with my goals.

Sylke has a rare ability to identify and address blind spots, equip you with strategies for better decision-making, and provide tools that work for working through disparate challenges. Whether it's navigating change, building resilience, or sharpening leadership habits, she’s an expert at designing practical, actionable solutions tailored to unique challenges.

If you're looking for someone who will inspire growth, challenge your assumptions, and help you accelerate toward your goals with clarity and confidence, Sylke is the invaluable partner you need.

Z.P. - Engineer, Venture Capitalist

I’ve worked with Sylke Chesterfield, CEC as my business and accountability coach for several years now, and I can honestly say she has been instrumental in my growth as a business owner.

Sylke has a rare ability to keep you focused on what truly matters. We meet every two weeks, and every session brings clarity - a clear path of what I want, what I need to do to get there, and the accountability to actually follow through. There’s no fluff; she tells it as it is! She helps me see what’s working, what didn’t, and most importantly, what I’m doing next.

With her guidance and accountability, we reached a major milestone last year - $1 million in sales in our fifth year of business. That didn’t happen by accident. Sylke will hold you accountable, challenge your thinking, and keep you on task, all while supporting you in a way that feels encouraging and empowering.

If you’re looking for a Business Advisor who brings clarity, consistency, and accountability - and who genuinely helps produce success - Sylke is someone I wholeheartedly recommend.

T.D. - Travel Advisor


Sylke Chesterfield gives the personalized coaching that every female executive can benefit from. From navigating a male-dominated company with long established dysfunctional patterns, to identifying with laser-focus on some areas I needed to work on myself, Sylke is that observational third party who can guide any female executive down a decisive path without being lost in the tendency to try to fix things. After just a short conversation, Sylke pinpointed important issues, gave specific recommendations, and was encouraging and empowering in all her suggestions. I highly recommend her.

T.A. - Engineer


Sylke is an effective communicator with secular, forward-thinking vision and a firm grasp of current branding techniques and technology trends. Upon our initial meeting, I recognized Sylke possesses the unique ability to read personalities beyond the surface. She posed probing questions that my close friends and family would never ask and intuitively identified my limiting beliefs, offering straightforward feedback and practical suggestions. Sylke’s objective coaching approach of active engagement and mindful accountability provided me clarity to discover my goals and to develop habits and the discipline to accomplish them. Her encouraging nature and insightful business acumen proved the right combination for Sylke to be my coach and an invaluable resource towards my achieving growth as a person and realizing professional success.

J.E. - Solopreneur


Structured, measured, with a methodical approach towards covering all the basic requirements in a way so that the project would not only stand up in the end, but also as to give myself thought – to things, avenues, and development, not obvious at first, but that gave me pause and ideas, as to where, what, when, and how, my idea might be best developed and deployed to fruition. She has a well-rounded thorough approach with a keen eye on the parameters and requirements for the final presentation. She was accessible and even visited when in town. She understood the importance of time – its necessity to fully create and complete the project and set appropriate deadlines and goals. Her efforts continued right through the final presentation at which she was present, and extend to this day. Any future [client of hers] would be most fortunate to have Ms. Chesterfield’s talents and expertise at their disposal.

G.D. - Solopreneur


Sylke and I have engaged on numerous projects and as a result she has recently provided me with professional coaching. Navigating the waters of entrepreneurship in a competitive environment while maintaining a household and your sanity can be a challenge. As a coach Sylke provides you with the tools and concepts to keep you focused and healthy. I urge you to engage Sylke when that voice inside says you need the help of an experienced coach.

S.G. - Entrepreneur


The simple act of having someone hold me accountable was invaluable. It was just what I needed to help me start the process of exploring what the next phase of my life was going to look like and be like. As a result of my work with Sylke, I realized that I didn’t need to (or want to) do what was typical, ordinary, or expected. Through my work with her I was finally able to give myself permission to simply live my next phase of life creatively and without a specific end goal in mind. What a relief not to be wracking my brain anymore in search of the one thing I should be doing next but instead allowing what will be next to come to me organically through experimentation and trial.

S.H. - Sales & Marketing Professional


Over the past few months I have met with Sylke for coaching sessions. The main purpose for starting the coaching relationship was for me to work on conflict resolution skills in my job as a pastor of a small church. Sylke provided me with tools for approaching those conversations with a broader perspective on how to navigate them and achieve a positive outcome that moves forward. In addition to conflict resolution skills, Sylke also helped me to see how to approach planning for and leading groups, teams, and strategic plans. Overall, I felt that the coaching was very worthwhile and helped me to grow as a leader in essential areas for my job.

G.S. - Pastor


Silka- I am so thankful to God that I was coached by you. You asked me to write out my goals on a big board and one of those goals was to do research in Early Education. I interviewed face to face with Senior Researchers today at The [Organization name withheld for confidentiality] in NYC and they offered me the job. I will be doing research that will examine children learning mathematics and using technology. There will be professional development to teachers and a great deal of collecting and analyzing data. The project will begin in January and should be completed in May which will keep me busy until the center opens

M.J. - Consultant


Sylke challenges me to think differently; asks questions that change my perspective; and provides actionable suggestions – some big, some small – that have helped me grow my business. She’s a great catalyst for improvement, and has a tremendous understanding of entrepreneurship.

W.D. - Entrepreneur


When I met with Sylke at a Company Holiday Party, I was interested in connecting with her to assess my management style and how she could add value. Sylke was able to quickly assess my skills and hone in on some of my inefficiencies. An immediate adjustment, was to increase my awareness of the importance of communication. She opened my mind to daily communication with all employees, a personal connection that will help foster employees importance to the organization. She also stressed the importance of communication, especially during times of employee conflict, and taught me to use phrases like, “Help me to understand”, I understand what you are saying, what would be some of your solutions to the problem.” We also discussed the importance of team building events with both operations, sales and clients. Sylke guided me through multiple upper management meetings with strategic communication and listening skills. She expressed the importance of dealing with the “C” Suite and how it can be a delicate dance, Sylke helped me rise to the occasion and communicate effectively. We discussed the value of face time with corporate and the fact that a piece of chocolate and small talk can go a long way. I found her technique to be informative and useful. She was able to guide me and teach me an effective communication style that aligns with my management technique. She has added value to my communication style and ultimately my team’s effectiveness to succeed.

R.B. - General Manager, Logistics Company

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