My philosophy on work

👋, I’m Lindsay.

I wrote this so you understand my philosophy on work.

You can use this as a quick debugging guide in case you see something in the wild that surprises you.

This document is a set of promises I intend to keep. If I don’t, I expect you to call me out.

I’m here to route information, remove roadblocks, and shield the team

At its core, I do three things for the team:

  • Route information to the right places at the right time
  • Remove roadblocks stopping us getting things done
  • Shield the team from interruptions and distractions

I have the responsibility for:

  • People. This means your health (mental and physical) and wellbeing at work, your relationship with work (including the dark side of this – keeping burnout at bay), and creating opportunities for you to grow
  • Systems. I am the single point of accountability for the upkeep, operations, and cost effectiveness of our socio-technical systems. I am the one on the hook for those systems. I will take responsibility when things go bad. I will ensure we work hard to make sure the likelihood of those bad things happening again is reduced.
  • Delivery. Ensuring we have a good pipeline of work to get on with. Ensuring that work is well defined and well sized. This is the part of work I find really fun!

I am here to leave this world a little better than I found it. If I’m doing my job well, when I step away from the team for long periods of time, things will continue to function well, and adapt and improve.

I value fairness, context, and pride in work


To be blunt – the main motivation for me doing a career change into leadership was because I experienced a real mixed bag of bosses. I thought “I can do a better job”, and here we are.

What motivates to gets me up every morning is creating a fair and just environment for the people I am responsible for.

I will call out things I think are unfair both in the workplace and for our customers, and I won’t hesitate taking a stand on principles.


Local rationality rules everything around me. People make what they consider to be the best decisions, given the information they have at the time.

Good judgement comes from experience. And experience comes from bad judgement. In my experience, disagreements often come from seeing the same thing from multiple, sometimes conflicting, perspectives.

My job is to facilitate building context for the team, so we can make more right decisions, and only make new mistakes.

Pride in work

I don’t have high standards, I have extreme standards.

I expect great work from the people around me, and I will push you to do the best work you have done in your career.

If I make you feel like I’m constantly disappointed in your work, that means I’m doing a bad job of setting expectations about what those high standards are.

My expectations are few but firm

I don’t have all the answers, and I don’t expect you to either. We’ll work together to build context that is a better approximation of reality.

Family first, work second. I am a firm believer in working-to-live, not living-to-work. If things are not on an even keel at home, your ability to do work is compromised.

Work must never trump your home responsibilities. If your partner asks you to do something important for them during work hours, I expect you to take time to do it. If you have kids, I expect you to take time off for special events.

I lead by example – I take time off during the school holidays so my wife can continue to study.

You know how to manage your time. I blanket approve leave requests. You know what is best for you, and I trust you to make the right call for the team and yourself. I view people going on leave as a chaos monkey that tests the anti-fragility of the team.

Feedback will be direct, prompt, and humane

If there is a problem, you will hear about it directly, promptly, and humanely from me. I don’t hold on to feedback. Delays in feedback create anxiety. My priority is to feed it back to you as quickly as possible.

I’ll provide feedback throughout the day, mostly through Slack. If it’s something particularly sensitive, we will do a video call.

When you have negative feedback for me, I expect it directly, promptly, and privately. Making mistakes is part of being human, and I am no exception to this.

I take a very dim view of hearing criticisms of me second hand. When I do hear second hand criticism, you’ll be hearing from me pretty quickly. This goes back to one of my values – fairness.

I go out of my way to take public responsibility for my mistakes. They are often teachable moments that are applicable to an audience bigger than me.

When you have positive feedback, please deliver it publicly. I like my work to speak for itself, and I appreciate when you say nice things about my work in public.

My office hours are 10.00 to 17.30

You won’t have my full attention before 10.00.

I have a young family, and my priority in the morning is getting them up and going for the day. If I’m in meetings before 10.00, you won’t be getting the best of me. Deal with that as you will. You’ll have a <50% hit rate if you schedule meetings with me before 10.00.

1:1s are the most important conversations I have

1:1s take priority in my calendar. This is where you have the opportunity to ask me anything. I will help you build context about what’s happening more broadly across the organisation.

We will use the full time. Sometimes there will be things we need to talk about, sometimes there won’t be. Even if you don’t think we have things to talk about, we will use the time.

I will hold you accountable for actions that come out of our 1:1s, and I expect you to do the same for me.

Scheduling wise, we can do 1:1s once a week, or once a fortnight.

With direct reports who have people management responsibilities, I want to meet once a week. With direct reports who are individual contributors, once a fortnight is fine – but if you find it valuable, I will do them weekly.

When I assume responsibility for you, I tend to do 1:1s weekly for two-to-three months, before we mutually decide to adjust the frequency.

Slack is the best way to contact me

Given I work remotely, Slack is my lifeline to the team. I am super responsive during the day.

Calendar: best to hit me up on Slack before you book anything. I will blanket reject meeting invites that don’t have agendas.

Email: This is where information goes to die.

I have some quirks. I’m working on them.

I focus on eliminating the negatives way more than I focus on accentuating the positives. I see problems pretty much everywhere I look. I work relentlessly to eliminate those problems. This sometimes means I don’t pay attention to the good things that are happening.

It’s something I’m working on and getting better at. Pull me up if you think I’m being too negative on something.

I spot dysfunction way sooner than most people. I’m like a hound dog when it comes to sniffing out dysfunction. I have found myself the canary in a coal mine more than once in my career. This has taken a personal toll more than once, and it’s something I’m very mindful of limiting the impact of in the future. If you see me withdrawing, it’s sometimes me pattern matching against past experiences that had Very Bad Outcomes.

I think holistically, which sometimes means I hold contradictory views on the same topic. To me, this is a strength when navigating complex systems. I am very good at navigating complex systems. To people around me, this can be frustrating! I can argue three contradictory points in the same number of minutes. I can appear to be hard to pin down on a position.

I actively seek contrarian views, sometimes to a fault. Healthy debate and conflict is the lifeblood of the team. I actively create opportunities for dissent. This can be uncomfortable for people who have never worked in environments like this! Apologies in advance – I will do everything I can to make your introduction to this as gentle as possible.

I am very mindful that I am often wrong, and I want to hear what I am wrong about, and why I’m wrong about it, as soon as possible. I don’t have all the answers, but I will relentlessly question until we get a closer approximation of reality.

I have a preference for working on product and delivery problems over technical ones. Sometimes this means the team ends up focusing on shipping and going faster, and work to manage tech debt and tech growth gets de-prioritised.

Sometimes this leaks into 1:1s (particularly if you are motivated by the same thing). I’m aware of it, but sometimes I still get blindsided by it. When you see this happen, let me know.

I am an integrator in a segmenter’s clothing. I have a natural tendency to blend the boundaries of home and work, and seamlessly transition between the two. Given I work from home, this can result in overwork and burnout.

I have lots of strategies to create boundaries between the two, like:

  • Separate physical workspace
  • Separate devices (my work phone goes on top of the coffee machine at the end of every day, so if you slack me after hours, you won’t get a response until 8am the next day)
  • Wearing different clothes for work and home

Call me out if I’m being naughty and working while sick.

I won’t add you on Facebook. There is a power dynamic in our relationship, whether we choose to acknowledge it or not. Me adding you on Facebook puts you in an awkward position if you don’t really want to share than information with me.

The choice is up to you. If you friend me on Facebook, I will accept.

Finally, I think to talk. I don’t often talk to think.

This document, like me, is a work in progress

I try to update it frequently and appreciate your feedback.