John Westworth

John Westworth · People, problems and change

The human side
of AI and change.

Listening, giving people a say and making it safe to experiment are common knowledge. They just aren’t common practice.

Go to the people.
Find the real problem.
Work it out together.

See how I can help

Former Director, Microsoft Garage Vancouver. Speaker represented by Spoken Artists.

About

Give me a problem.

John Westworth speaking into a microphone at an event

A former manager once told my new manager: “If you want to get the best out of John, give him a problem.” He was right.

My work at Microsoft has spanned consulting, sales, customer success, IT, innovation and organisational change. I work best with people on messy problems where the answer is not obvious, and often where the problem is not what it first seems.

I get close to the work, question what we think we know and help people find a small first step. A big part of that is helping people see what they’re capable of, then giving them the space to try.

Work with me

How I can help.

I help teams work through problems and change. I get close to the people doing the work, find what is getting in their way and help them work through it together. That might mean making a hard decision, testing an idea or changing how the work gets done.

01

Leadership teams.

Your leaders need to agree what matters, who owns what and how to move forward together. I design and run sessions that give them room to work through it and leave with clear decisions and commitments.

In practice: I helped leadership teams work on shared ownership, decision making and accountability. In one session, we used “Buy a Feature” with play money to make trade-offs visible, then turned the discussion into team commitments and individual actions. Later feedback reported that the language and frameworks were still being used in conversations about accountability and culture.

Read the leadership case study

02

Hackathons for everyone.

You want people with different skills and levels of experience to tackle real problems together. I help shape the event, find worthwhile challenges and give people a useful way to take part, whether they want to explore, build or stretch.

In practice: I led Vancouver’s local Hackathon campaigns, helping people work across teams, try unfamiliar tools and turn ideas into working projects. In 2025, eight projects involving Vancouver staff received recognition in challenges open across Microsoft and sponsored by senior leaders.

03

Helping people early in their careers.

People early in their careers often have more to offer than they realise. I help them see their strengths, learn from other people and take practical steps towards the work they want to do.

In practice: I built Career Builder from employee research into a programme of learning sessions, practical tools, a newsletter, a website and an AI agent for finding the content. By July 2025, more than a third of Microsoft Vancouver employees had taken part in different parts of the programme.

04

Putting AI to work.

You have access to AI, but where would it actually help? I work with the people doing the work to find a real problem, try an approach and judge whether it makes things better.

In practice: I designed and ran a customer workshop around an affordable home-buying challenge. Teams used AI to explore ideas and question assumptions, then developed proposals they could present. The session ended with concrete proposals for the customer to assess; their innovation lead requested the presentations for evaluation.

05

Speaking.

I spent 26 years at Microsoft, most recently leading the Garage in Vancouver, helping people experiment with new ideas, adopt emerging technologies and find better ways to work.

Now I speak about AI, innovation, leadership and the future of work, drawing on what I learned from doing the work inside a global technology company.

Available for 45-minute talks, represented by Spoken Artists. See my speaking profile and enquire.

Speaking

From experience to action.

There are plenty of conversations about AI and innovation. I talk about what it takes to help people try new things, find problems worth solving and turn good ideas into useful work.

My 45-minute talks cover AI adoption, innovation, leadership and the future of work. Speaking enquiries are handled by Spoken Artists.

Explore talks and speaking availability

Ideas

Questions worth asking.

What behaviour are the conditions creating?

We tell leaders to be curious, then reward certainty. We ask people to experiment, then punish failure. Before trying to change the person, look at what the system makes easy, hard and risky.

Is more output creating more value?

AI can make one person faster while making the whole system slower. Someone still has to read, check, understand, judge and act. If every hour saved becomes another hour of work expected, we’ve intensified work rather than transformed it.

What is the smallest thing we can try?

A small experiment makes the first step easier. Action gives us data, data helps us learn, and learning builds confidence. If the evidence kills the idea, let it go.

Writing & tools

Useful things to take away.

Unfinished Thoughts

I write about work, change, careers and what happens when good ideas meet real life. You can read and subscribe to my newsletter on LinkedIn.

Read Unfinished Thoughts

Good work isn’t enough

Five questions to help software engineers understand the value of their work, explain their contribution and build career options.

See the guide and worksheet

For people working on their careers

A practical guide to making your CV easier to understand, with an AI prompt to help you review it.

Download the CV guide (PDF)

Contact

What are you working through?

Tell me what’s happening, what you’ve tried and what you need to change. We can work out whether I can help.

A first conversation is a chance to compare notes and understand the problem. If there’s a fit, we can agree what a useful next step would look like.

Based in North Vancouver, Canada. My experience includes online learning sessions and in-person workshops. We can discuss the format, location and any travel needed for future work.

For speaking engagements, contact Spoken Artists. For workshops, facilitation and consulting, book a conversation with me below.

Book a 15-minute conversation

john@johnwestworth.com

Find me on LinkedIn