For a good part of my working life, I have been the President of a medium-sized business with several hundred employees in several locations. I am also a major shareholder in this family-owned business. As the leader of a family business with other outside shareholders, I have had to deal with major affairs of the business which I was not able to discuss with staff, friends, or the other owners, leaving me somewhat isolated.

For the past several years I have had the good fortune to have Winston as my coach and confidant. He has helped me in seeking to understand my situation by asking effective open-ended questions. This has been critical to creating options and action plans that I become accountable for that have helped me move forward successfully on many personal and business initiatives.

I believe his own extensive business background enables him to understand my situation and he can then effectively ask questions that help me to solve my goals and objectives.
Winston continues to work with me as the business grows and flourishes as a key community supporter and employer.

I am very appreciative of the role Winston has played, and highly recommend him to other business owners as a coach in the ways he has supported me.

David Askew
CEO, Askew Foods

I have been involved with Winston Pain in a business relationship as a coaching client.

Winston has previously been a business owner for 26 years, and coupled with that experience and knowledge, comes to coaching with a world-class qualification from the Conscious Coaching Academy in the United Kingdom.

It is not just Winston’s qualifications and background that make him a highly effective and transformational coach, it is the level of his ability to listen intently to me as the client and to pose quality, curiosity-based questions that make me think in my unconscious mind and get to the bottom of the belief system that has been limiting my growth.

This process that Winston has taken me through has allowed me to build a Vision of my business far beyond where I was thinking. He has enabled me to believe in my full potential and see that it is possible to go beyond what I thought previously.

Winston has the passion and skill to support others to build successful businesses, navigate challenging situations, and be the best version of themselves.

I thoroughly recommend Winston for his coaching ability and am grateful for my association with him.

Kate Brown
Founder, EduKateNZ

I have been lucky to spend time with Winston on both a personal and professional level in the years that I have known him. He has a passion for coaching which is apparent in his genuine interest in the development and success of others. With his years of owning and operating a successful local business, combined with endless hours of community volunteer work, he has developed a toolbox of skills that is second to none. Winston is an excellent listener and problem solver who has a compassion for others that makes him a joy to be around. He will lead you down rabbit holes of thoughts and out the other side with a clearer view of the direction you want to go! Without hesitation, I would put my trust in Winston.

Jeremy Osborne
Real Estate Advisor, Royal LePage Access Real Estate

Winston is a master in seeking clarity and a path forward. He coached us through one of the most challenging and complex community endeavors I’ve ever been involved in, and in the process, I found myself on a 20-year career journey more rewarding than I’d ever imagined alone. All prefaced by asking essential questions that focused us on what we could actually influence. Pragmatic, entrepreneurial, and as genuine as they come.

Phil McIntyre-Paul
Co-founder, Former Executive Director, and Senior Consultant of The Shuswap Trail Alliance

We are all busy in life, and there are excuses for everything, but a very valuable piece that is absent in small businesses is having a trusting relationship with someone that can ask the “unasked” questions and hold you accountable for following your plan. I found the most optimal way to become your Future self is by finding who you are today and what steps are required along the way to become that person. The old saying if you “fail to plan, you should plan to fail” is so true and easily overcome with coaching. Finding your future self starts with making a plan, staying accountable to the plan, adapting the plan and questioning the plan. Having a coach on your team to confirm it aligns with one’s goals, values and objectives is invaluable and non-existent for most business owners. It is simply an eye opening and life changing moment once you immerse yourself in the process. I highly recommend this opportunity and relationship to those who want to do better and feel self satisfaction that you didn’t know existed.

Trent Sismey
MPAcc, CPA, CA
Principal
Trent Sismey Inc.

Winston possesses a remarkable talent for uncovering insights through conversation. His coaching style empowers business owners to gain self-awareness about their thought processes and decision-making. He excels at facilitating focused discussions that lead to actionable steps, maximizing the value of our coaching sessions. Winston’s blend of brainstorming and targeted guidance has demonstrably accelerated my growth, and I continue to experience positive changes both during and after our interactions.

Dustin Serviss
CFP CLU CIM CHS
Serviss Wealth

I had the privilege of being coached by Winston Pain during this past year.

Winston is a truly exceptional coach.  He creates a safe, creative space that helps his clients grow and discover their most powerful insights.  He is calm, humble, and reassuring in his role as a coach. These attributes position him as your “partner” in the most powerful relationship one may experience in a lifetime.

With an extensive background in business ownership, Winston exhibits remarkable curiosity combined with great intuition in asking just the right question to help you find the answer you never knew you had.

He is highly intelligent, and process driven which greatly enhances the growth within the coaching process.

Perhaps the most impactful work he facilitates is a deep dive into the client’s values. Clarifying one’s “true north” of core values is transformational both in understanding past decisions and being able to assess future decisions knowing full well what drives you.

Winston is an outstanding coach whom I would recommend to anyone interested in achieving their most important aspirations (both professional and personal).  The process that he takes you through is second to none that I have encountered in the coaching profession.

Darrell Bilbrey
Hoover, Alabama