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One-On-One Operating System
Coaching Skills For People Who Lead Change

Limited time only

A 12-week experiential program to help you develop skills to lead change. Focused on habit formation, not knowledge acquisition, so that you can become the coach everyone wants.​

Why Coaching?

The pace of change is accelerating. Every week there are new technology innovations, new competitors and new ways of working.

The most influential leaders in organisations are those who can lead at speed. The pace of change requires leadership at all levels, not just senior management. CTO's, Product Leaders, Team Members, Managers, Scrum Masters and Coaches. All of these are crucial leadership roles in fast-paced organisations.

Command and Control leadership styles are not effective in leading change. Instead, a coaching style of leadership has been shown to create better change outcomes. Leaders who coach master these three skills: Active Listening, Asking Coaching Questions and Increasing Self-Awareness.

By mastering these skills you'll become a leader everyone wants to work with. People will feel heard, respected, motivated and inspired when they work with you. As a result, you'll inspire teams of engaged people that deliver big business results.

One-On-One Template

The problem with traditional coaching programs.

It's likely you have already started to learn about coaching. You probably faced the same challenge I did. Content that's theoretical and hard to put into practice.

Research in 2006 from BlessingWhite suggested that 74% of Managers had some form of coaching training. Only 23% of people coached by managers who attended the course thought the coaching had a significant impact on performance. 10% of coachees actually claimed the coaching got worse.

The problem with many coaching courses:

  • Overly theoretical and too complicated. Too much focus on models and frameworks.

  • Not delivered within the workplace context. The role leaders perform in organisations requires a specific type of coaching.

  • Too much focus on individuals. Not enough on teams and organisational challenges.

  • Expensive. A typically coaching certification program costs anywhere up to $10,000.

  • The seemingly simple behaviour change of giving a little less advice and asking a few more questions is surprisingly difficult. You’ve spent years delivering advice and getting promoted and praised for it.

Coaching is best learned through doing it.

Learn More
This Operating System is for Leaders who want to.....




Structure the conversation to empower your team member.



More Often

Using coaching skills enables you to delegate more rather than being a bottleneck.


Keep People Motivated

Learn how to quickly understand the factors influencing your team members motivation.




Good one-on-ones keep team members engaged in the problem-solving process.


Deliver Better Products

Better One-On-Ones translate into better product outcomes. 


Improve "Underperformers"

It's tempting to avoid the tough feedback. Once you learn how and practice, it becomes easier.

What's included?

A guide to better one-on-ones.

Learn the 5 ingredients to successful one-on-ones and how to put them into action.

A template for one-on-one conversations.

Plan, deliver and track your one-on-ones with this note-taking system. 

5 coaching exercise templates.

Bring fun and focus to your one-on-ones with 5 coaching exercises. These help support career discussions, goal setting, tackling fears and building new skills.

One-On-One Template Tracker
Who is the creator?

Hello 👋

I'm Toby Sinclair, the creator of this Operating System.

I'm a Business Executive based in London. I've worked in Product and Tech organisations in various roles for the past 15yrs.


I have a unique blend of skills and experience that I've used to build this operating system. Software Development, Professional Coaching and Management.

I've been coaching professionally now for 6 years across many organisations. I've coached CIO's, product teams and everyone in between.

I'm a Professional Certified Coach (PCC) with the International Coaching Federation. Sadly many coaches are not professionally trained. To get this credential means I've completed 125hrs of training and delivered over 500hrs coaching conversations.

My philosophy of management is coaching. I believe that your role as a manager is to create an environment that unlocks the potential in your people.

If you'd like to know more, here is my story.

Toby Sinclair
Limited Time Beta-Access

This operating system is built to help managers have better one-on-ones so that they can better grow their people.

A key aspect of great management is continuous improvement. I intend to implement that principle with this product.

For a limited time only, I'm releasing a free beta version of this operating system for early adopters.

In return for access, all I ask is that you provide feedback. You can help make this a great tool that helps managers have better one-on-ones.

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