66 ways to have more fun as a strategist (and maybe get a bit better)
Read widely.
Read weirdly.
Enjoy the fact that part of our job is to read widely and weirdly.
Make your arguments simple.
Now make them simpler than that.
Always start with a written document.
Know a really good meme account for the category you work with.
Know a really good podcast your audience would listen to.
Assume every problem has a fascinating side to it.
Assume ‘boring’ problems have an even more fascinating side.
Start your presentations with a twist.
End your presentations with a lesson.
If you’re feeling spicy, end your presentations with a cautionary note.
Don’t obsess with strategy frameworks.
Don’t bore your client with strategy frameworks.
Remember the audience will never read your strategy.
Use simple words your mum would understand.
Use simple words your mum’s mum would understand.
Don’t interrupt people, especially when they’re demonstrating passion.
Notice what people say and play it back to them.
Start sentences with “I wonder if”.
Observe people in coffee shops.
Observe people in public transport.
Don’t stare.
Say “I don’t know yet” when you don’t know… yet.
Don’t worry about memorising everything you read.
Study ways to find out about things.
Use Claude AI to explain your own argument back to you.
Now ask it to pretend to be your favourite celebrity and do it again.
Believe people when they say you did great.
Write with a thicker pen.
Write with a bigger typeface.
Always change to 1.5 line spacing.
Don’t cheat on your one-pagers by making the typeface smaller.
Have strategy pals.
Cmd+S every other minute.
Close a browser tab.
Now another one.
Buy a random magazine at your local corner shop.
Do a walking meeting.
Breathe while you talk.
Daydream for no good reason.
Thank people who’ve helped you.
Be generous with compliments.
Be specific.
Listen more than you speak.
Write a list.
Write a stream of consciousness.
Give yourself 10 minutes to write the clearest answer you can think of.
Then feel ok that you’ll probably need time to get to a simpler one.
If it feels obvious in retrospect, stick with it.
Write a haiku about your audience.
Say your argument out loud.
Argue against your own argument.
Admit when you are wrong.
Say “sorry” when you have to.
Assume the work you’re getting back has been thought through.
Ask questions without judgement.
Find reasons to build on things.
Focus on agreeing a direction, not winning arguments.
Say you have a clash – and leave it at that.
When you have nothing to do, read.
If you’re tired of reading, write.
If you’re tired of writing, go for a walk.
If you’re tired of walking, take a nap.
Have a healthy snack of choice.
Break your own rules.
Inspired by this fun piece by Andrew Boulton.
