John Westworth · People, problems and change
Most hard problems at work are not just technology problems. They are human ones.
Go to the people.
Find the real problem.
Work it out together.
About
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.
Over 26 years at Microsoft, I’ve worked across 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 something small they can try. A big part of that is helping people see what they’re capable of, then giving them the space to try.
Selected work
01
The brief was an offsite. The real work was shared ownership, clear choices and conversations the team needed to have. I designed and facilitated sessions that helped leaders work through those questions. The language and frameworks stayed in use afterwards.
02
Around 1,000 people registered for Vancouver’s Hackathons each year from 2024 to 2026. My focus was on what made taking part possible: worthwhile problems, connections across teams and room to share unfinished work and learn.
03
I designed hands-on learning and customer workshops around real tasks and business problems. People explored what was possible, challenged ideas and worked out what was worth taking further, with guides they could return to afterwards.
Ideas
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.
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.
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.
Contact
I’m always happy to compare notes with people wrestling with the human side of AI and change.