This past Saturday, Cape Town Chess Federation hosted an exciting new workshop: Teaching Chess Online – A Professional Development Program for Coaches, held at Bertha House in Mowbray. The event, proudly sponsored by the National Lottery Commission and endorsed by Chess South Africa, brought together coaches, educators, and chess enthusiasts for a full day of learning, sharing and inspiration.

The sessions were led by Craig Willenberg, Senior Coach of the Cape Town Chess Federation, and Reuben Salimu, Head Coach of Chess South Africa. Here are a few highlights from the day:

Coaching with Purpose – Craig Willenberg

Craig opened the day with a simple but powerful reminder: coaching is about connection. “Your students must like you, believe in you, and see the way forward,” he said. Improvement in chess is a journey, and a good coach is a guide who both challenges and encourages.

His key message? Lessons must be objective-based. “Inch wide, mile deep,” he quoted from Jacob Aagaard – a nod to the importance of well-prepared, focused sessions. He emphasised that while players should think wide over the board, coaches must go deep in their preparation.

Craig encouraged coaches to hook their students right at the start of each lesson and to always show learners what they’ve achieved. A lesson must feel like learning – otherwise, it’s just a chat.

He also touched on time management, coaching etiquette, and practical tools:

Use WhatsApp reminders and give post-lesson updates
Set cancellation policies to protect your time
Use tools like Google Drive to stay organised
Create Lichess studies, explore public resources, and use Zen mode to help students focus

Perhaps one of his most thoughtful questions was:

“How much time do you spend trying to find out how your students like to work?”

It was a reminder that coaching is not one-size-fits-all.

Mindset & Monetisation – Reuben Salimu

Reuben’s session challenged coaches to think big – and think practically.

“Why do you want to become a chess coach?” he asked. Is it to help your child? To earn a living? To grow a school programme? Whatever your reason, it needs to be clear and connected to your life.

He tackled the often-taboo topic of money in chess coaching.
“You cannot charge below what is worthwhile for you,” he warned. If you do, you risk not giving your best to your students – and worse, burning out. “There are not too few students,” he said. “There are too few visible coaches charging their worth.”

His advice was clear:

Set goals and a target income
Be visible, target the right audience, and charge confidently
Don’t build your business around the top 1% – you’re not only coaching the next National Champion, you’re helping kids (and parents) grow through chess

He also outlined common reasons coaches fail:

Poor communication – learning can’t happen without attention and two-way engagement.

Steep learning curves – simplify your language; not everything needs to be ‘GM-level’.

Lack of a curriculum – plan lessons, use tools, and build progression.

Reuben introduced the Affinity–Reality–Communication triangle (a learning model), explaining how shared understanding, empathy, and good examples help build effective relationships with students.

On the tech side, he encouraged coaches to explore tools like:

Lichess and Google Meet for lessons
Chessable for openings and tracking progress
Chessvision.ai to snap positions from books
AI tools like ChatGPT to interpret games and assist with lesson planning

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Final Reflections

The day was packed with insights, hard truths, and hopeful encouragement. Whether you’re a seasoned coach or just starting out, the key takeaways were clear:

Know your value
Plan with intention
Communicate with purpose
Use the tools available to you
And always keep the student’s growth at the centre of your work

A huge thank you to our facilitators, attendees, and partners. Events like these are only possible through support – and we’re especially grateful to the National Lottery Commission for sponsoring the day, and to Chess South Africa for their continued endorsement and guidance.

Until next time — keep teaching, keep learning, and keep growing.