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  • Let’s do Business


My coaching practice, established in 2002, is for people who are ready to make career transitions from professional life into entrepreneurship, and ready for the right professional help to develop the skills, courage & confidence to effectively design, plan & start their own successful career in business.


Gail Cherry


32.53 million people are currently working in the UK, per statistics released in January this year, and one in ten intend to start their own business within a year. That means 3.2 million more people are expected to become their own boss by 2020. Are you one of them?

There’s a rapid growth in self-employment in the UK, and those people with itchy feet who swap their jobs to go it alone, will find that, despite being extremely skilled there’s this business of learning new skills, using new tools and they want to learn fast.

I believe it’s a real shame for the world when those star-quality, super-resourceful people who take the plunge to follow their passion don’t see it through because the process from idea to launch gets too intense, too overwhelming & complex to manage. 

I have an approach that’s wholesome & nurturing, and a talent I’ve put effort into over the years to become extremely skilled at making things like change, solutions, shifts and new possibilities. I have a gift for enabling people to think bigger and a gift for alignment, which makes this process a whole lot easier.

I help people design and create a career in business they’ll love and enjoy; aligned with their values & designed to make a difference, and I create learning spaces for people to gain relevant new skills & knowledge, which offer a safe environment to try out their ideas, and underneath all this I inspire and encourage people to have more faith in themselves.

I bring my life’s work into the mix; I started my own business at the age of 18 and by 21 I had bricks & mortar and a team working with me. I qualified in professional training & development; designing & delivering workshops since 1998, qualified in business advice and later studied coaching and mentoring at post graduate level; choosing transformational learning and psychodynamic aspects of the self to better understand, support & develop entrepreneurs through their entrepreneurial journey. I work deep to understand my customer’s needs and context and I’m always reading, observing and learning.

I hold space for only a small number of clients at any one time to ensure I’m available for them as they work through their customised programme. Clients choose either a short-term or long term package and my pricing structure is simple, it bucks the trend of the traditional coaching model: A fixed fee is agreed and paid in instalments to the end, and we work out: what you need, what’s a priority now and how & when you take the coaching. As for my workshops, it’s a pay-what-you-feel basis with a ‘value-to-you’ price guide.

I’ve helped more than 500 people make successful career transitions from student, military & professional life into entrepreneurship. I work with people 1:1 and in groups to develop the skills, courage and confidence to effectively design, plan and start their own successful career in business. I’m passionate about ideas, innovation, possibilities and I love what I do.

I have a proven track record and a good reputation in the field of enterprise education and enterprise support and regularly hired to coach on fabulous business support projects. I’m also resident business coach at Leeds Beckett University since 2015, and currently working with new and early stage businesses in the Leeds City Region.

Come join my fruitful school for super resourceful people, because, I’m on a mission to give out stars to the world.

Coaching & Mentoring

My coaching approach helps open-minded thinkers who have a keen sense to learn by first assessing & understanding their developmental needs and by properly aligned support to develop, learn and grow so they can better perform through their entrepreneurial journey.

External Facilitator

I’m available for hire to help project leads who want to have their enterprise programmes professionally delivered, ensuring their clients needs are always met; with a fresh & engaging style & content, along with an abundance of applied-learning success stories.


My style of workshops help people who want to develop new skills to be immediately put into practice by avoiding blah blah blah and by coming to a learning space that’s active & social: interactive, collaborative, challenging, meaningful, purposeful & engaging.


I’ve helped more than 500 people make successful career transitions from student, military & professional life into entrepreneurship.

I was worried about making the transition from a very regimented career & heading into the world of business. Gail Cherry made me feel as big as my new challenge. She helped me discover the tools that I needed to navigate my way through an entirely new environment with confidence.
Leigh HumplebyExpert in Medical Trauma
Gail is a professional, personable coach who has proven ability to support new businesses to develop their ideas and work through problems. The feedback from our members has only been positive and it is a pleasure to work with someone so committed to their role.
Independent Food & Drink Academy
Gail is a wonderful coach who knows exactly how to bring the best out of people.
Friendly, warm, personable & full of ideas, she helped me identify 'my brand' and make positive plans. she's a pleasure to talk to and always provides helpful and invaluable expert advice.
Katie PortmanAward Winning Blogger
Are you ready?
Sign me up


‘Our chief want is someone who will inspire us to be what we know we could be.’
Ralph Waldo Emerson.

Career transition

Discover your inner depths and talents

Transition into Entrepreneurship

Transition into Self-Employment

Put your best foot forward

Green Space

Coaching in green…

Innovation new Possibilities

Work on the Business

Inspiration for business ideas


In:Synch Coaching Assessment…


Breakthrough being stuck

"Gail is professional, kind & great fun to work with, she has been invaluable in helping me find my niche & giving me direction"
Steph CroninBlack Bee Creative


Come walking with me in Holmfirth or let’s do our coaching by Skype.
Call or email to make arrangements
01484 687 534 or 07980 311 516

Free Consultation

A complimentary phone-call provides the opportunity to discuss your developmental goals, and see how we can work together.

Fully Confidential

Your privacy is very important to me therefore a confidentiality agreement is always signed at the outset.