CTO Coaching

Joel Chippindale’s one-to-one CTO Coaching supports you to accelerate your development, achieve your goals and be the leader you want to be

Get started with coaching

Whether you’re a seasoned CTO or someone new to leading in a software engineering team, your role in the ever-changing environment of a start-up or scale-up is complex.

As your career advances, you are expected to take more responsibility for how you spend your time, set your goals and define and develop your role. While this is often exciting and rewarding, it can also be stressful and lonely. Knowing who to turn to for advice and support might be hard.

Working with a coach is a pragmatic and effective way to tackle the challenges and stresses of your role. My coaching can help you navigate change, build your confidence, accelerate your learning and development and support you in achieving your goals.

Areas that I can support you with include (but are in no way limited to):

Flexible support tailored to you

My coaching programmes are flexible. We will explore what you are looking to achieve during an initial chemistry call and design a programme that will work best for you.

The length of the programme, frequency and length of sessions and the amount of support between sessions will all vary depending on the programme we agree on for you.

Explore coaching options

Anywhere in the world

Coaching sessions are via video call. This allows us to meet when and where works for you.

This can be anywhere in the world. I have coached engineering leaders from Brazil, Canada, Colombia, the Czech Republic, France, Germany, India, Italy, Japan, Lebanon, the Netherlands, New Zealand, Singapore, Spain, the UK and the USA.

I am based in the UK and if the time difference between us is large this may mean that the times for our sessions are more restricted. For example, if you are live on the Pacific Coast of the USA sessions are likely to have to be before 10am.

A coach and mentor

I am Joel Chippindale. I am a CTO Coach who has coached over 70 engineering leaders. I also have over 20 years experience building, scaling and leading software development teams, mainly in start-ups, including CTO and COO roles at FutureLearn and CTO roles at Econsultancy and Unmade.

I believe in the importance and value of building inclusive and sustainable teams and have experienced the challenges of nurturing the cultures, skills and practices that enable teams and individuals to achieve their full capabilities.

I offer a combination of coaching and mentoring to support you to make the most of your skills, knowledge and experiences and help you develop your capabilities.

Where appropriate, I can offer suggestions and guidance based on my hands-on experience of leading engineering teams at start-ups and scale-ups.

The impact for you

I share these quotes from some of my coaching clients to offer you a tangible sense of the experience and benefits of being coached by me.

More testimonials.


The coaching programmes that I offer are personalised for you and the cost will vary depending on the programme we design for you. Coaching programmes start from £3,000 +VAT .

I also offer coaching scholarships to engineering leaders at startups or scaleups who identify as being from a group that is underrepresented in technology and cannot afford coaching yet.

Next steps

Let’s have a call and we can explore your needs and how the coaching and mentoring that I offer can support you.

Let's talk

Or your can email me at joel@monkeysthumb.co.uk.

Frequently asked questions about coaching

I coach engineering leaders who want to improve their performance at work.

The majority of my clients are the most senior technology person in their start-up or scale-up, perhaps the CTO, or Head of Engineering, or Director of Engineering. But I also coach people in a wide range of senior engineering leadership positions, including Directors and VPs of Engineering.

In the words of Bill Gates, “Everyone needs a coach”.

You need a coach if you want to improve your performance. If you want to serve your teams better. If you want to accelerate your development. Or, if you feel stuck.

I have written more about this in my blog post, “How does a CTO know when they need a coach?”.

My coaching programmes are flexible and we will build a programme that works for you.

In a typical programme we would start by exploring your goals for coaching and set an ambitious vision for where you want to be at the end of the programme.

We would then have regular coaching sessions and I will use coaching and mentoring to support you to:

  • Focus on your most important goals.
  • Provide a calm and safe space for you to think and reflect and help you make sense of your thoughts, needs and situation.
  • Build your confidence in yourself and your abilities.
  • Challenge assumptions and beliefs that you may be holding you back.
  • Identify concrete actions to take that will make progress towards your goals.
  • Accelerate your development and build your ability to self coach.

I will recognise many of the challenges you face from my own experiences of being a CTO and so, where appropriate, will also be able to share these experiences with you.

I will also be available to offer support between sessions.

I can also support you to get feedback from those you work with.

The length of the programme, frequency and length of sessions and the amount of support between sessions will all vary depending on your needs.

Most of my clients have their coaching paid for by their employers.

Companies pay for coaching because of the high return on investment from the impact it has. It is a pragmatic way for companies to support the development of their best senior leaders by working through their challenges and transforming their learning directly into results for the organisation.

I can support you to think about the impact of your coaching programme in order to make the business case for your coaching. Let me know if you want to cover this in our chemistry call.

Mentoring is when you learn from the experiences of others. This can be very valuable and can accelerate your learning.

Coaching starts from the position that you are capable, resourceful and whole and that the answers to your challenges are already within you. A coach is a thinking partner who will support you in discovering these answers.

Coaching can be much more powerful in building your confidence and skills, and in arriving at solutions to your challenges that really work for you and your context.

I offer a combination of coaching and mentoring to ensure that you get the support that you need.

You are probably busy. You probably have a role where you are never “done”. In this environment it can be difficult to feel that you have the time to be coached.

Coaching supports you to focus on what is most important. This helps you spend your time wisely and have a greater impact in less time. Most of my clients feel like they have more time rather than less as a result of coaching.

If you feel that you are too busy for coaching then this is likely to be a sign that you coaching would be particularly valuable for you.

I recommend Richard Hughes-Jones’ article Executive coaching: a complete guide to finding the right coach for you that is packed with excellent advice and applies equally well to choosing a CTO coach.

Each coaching relationship is different, and as we work together we will learn what works most effectively for you.

We will learn which how to adjust the coaching approaches that work best for you and also explore the balance of challenge vs. support, of coaching vs. mentoring.

I also recommend the following to get the most from your coaching relationship

  1. Be ambitious. You are more capable than you believe and with coaching support you can go further than you you give yourself credit for. If you don’t have clear goals when you start your coaching that is OK and we can work together to identify where you are going.

  2. Be open. Coaching is a thinking partnership and the less you hold back, the more effectively we will be able to think together. I will keep everything you say confidential and hold you in unconditional high-regard in order to provide you with a safe space to explore your ideas and feelings.

  3. Take action. Our sessions will provide you with space to understand yourself and your situation more clearly, challenge self-limiting beliefs and commit to actions to make change. However this will just be talk unless you also take action between our sessions.

  4. Offer feedback. We will learn how to work together more rapidly if you offer direct feedback about your experience of being coached. This will help us both adapt our approaches so that you can get the most from your coaching programme.

I can also recommend Evgeny Shadchnev’s article How to work with a coach that provides great advice for getting the most from your coaching relationship.

For any further questions, please send me a message.

If you’re ready to get started, then book a complimentary “chemistry” session. As part of this first meeting, there will be ample opportunity to ask any further questions you might have.