01 My Personal Mission
Build the right things, the right way, with quality and speed.
“Right” can change based on context, but the essence stays the same:
- We are solving real problems, not just producing activity.
- We are thinking from first principles, not blindly following precedent.
- We are making thoughtful trade-offs, even when the answer is not popular.
- We are optimising for global maxima, not local maxima.
I also believe quality and speed can coexist:
- Quality is ultimately measured by user impact.
- Quality is supported by reliability, security, maintainability, and operational readiness.
- Speed is not rushing but is choosing the few things that matter and refusing the rest.
- Speed comes from clarity, focus, simple choices, and ruthless prioritisation.
02 How I Lead
I set the pace, and I will bring you along.
I set high standards. I also genuinely care about people. These are not opposites.
I will make sure that the mission is clear, and the environment is supportive,
for you to do your best work.
Depending on what you need, I move between three modes, roughly:
03 People First
Family and Health come before work.
I want people to do meaningful work, grow in their craft, and feel proud of what they are building.
There will be intense stretches, but I want a culture where burned weekends are not the default.
Reduce WTFs as much as we can from Day 1.
I care about your growth. I'll push you past what's comfortable, as that's where you learn most.
In return, own your development, tell me what you're reaching for, and I'll support you.
04 How Trust Works With Me
I start with positive intent.
I assume people are trying to do good work.
I do not expect perfection. I do expect honesty, ownership, and learning.
Trust grows when you:
- Demonstrate your clarity of thought
- Think from 1st principles and next-order effects
- Own the outcome with great follow-through
- Optimise beyond your own area
Trust reduces when the opposite happens.
With greater trust comes greater autonomy.
I do not need to be involved in every detail when I know the outcome is in good hands.
05 How to Communicate With Me
Clarity is a courtesy. Breadcrumb early.
Write. Async.
Achieving clarity of thought is important, and you can only do that when you sit down and write.
Meetings are for deciding/aligning, not for updates that can be done through a Slack message.
Be Open
Push updates often. Don't worry about spamming my inbox. That's on me to manage.
I prefer comms in the open, so we can build a shared consciousness for the entire organisation.
Good Update
A good update usually tells me:
- What is happening.
- Why it matters.
- What decision or help is needed.
- What options were considered.
- What you recommend.
- What risks or trade-offs I should know.
Bring me your read of the situation. I may not always agree, but I will appreciate the ownership.
Traffic Lights
Use traffic lights for status. Green / Amber / Red, then the detail.
Do not sugarcoat. Be honest with the status or the evaluation.
Early Warning & Clean Escalations
Give me early warning as soon as you smell trouble, so that we can resolve issues quickly.
I will be assured when you say “I've got this, but I wanted to let you know early.”
It's ok to do a clean escalation to move things along. Don't wait too long.
Make use of my role/position to help make progress.
I Work Odd Hours
I may Slack you at odd hours. That's my personal schedule.
Unless I say it is urgent, please only reply during office hours.
06 Directness and Feedback
I am direct because ambiguity is expensive.
If I disagree, I will try to say so clearly.
If I think something is not yet good enough, I will try to explain why.
If I ask hard questions, it is usually because I am testing the thinking, not attacking the person.
At the same time, directness should never become disrespect.
Care and challenge must go together.
I also want feedback from you.
If I am unclear, wrong, moving too fast, creating confusion, or missing context, tell me.
I may not always react perfectly in the moment, but I will take it seriously.
Questioning attitude is better than blind obedience.
07 Decision-Making
A clear decision beats prolonged indecision.
I value good decision-making, but I do not expect perfect decision-making.
Good decisions require judgment, context, trade-offs, and timing.
Sometimes the cost of waiting is higher than the cost of being wrong.
I prefer a clear decision with ownership over prolonged indecision.
When a decision is reversible, we should move faster, learn, and adjust.
When a decision is hard to reverse, we should slow down enough to understand the risks.
Have strong opinions, loosely held.
Argue for what you believe, but be willing to change your mind when the facts or context change.
08 What I Value
Winning as a Team. Growing as an Individual.
I value teamwork. We succeed as a team, not as isolated individuals.
I value ownership and accountability. Own the outcome, and your mistakes. Learn, and move forward.
I value craft. Keep improving the quality of your thinking and your work.
I value intellectual humility. Be confident, but stay open.
I value continuous improvement. Leave things better than you found them.
I value respectful challenge. The best ideas should win, not the most senior voice.
09 What I Dislike
Red flags that slow us down.
I dislike net-negative behaviour: disrespect, politics, drama, or behaviour that drains the team.
I dislike long meetings without clear decisions or outcomes.
I dislike unnecessary acronyms and jargon.
I dislike being called “Boss”. Please call me Winston.