It just occurred to me that I’ve been working professionally for 10 years 👴
Here are a few aphorisms and tidbits I’ve picked up along the way, shared in the form of Kevin Kelly’s. Your mileage may vary! Also sadly I’ve found that the best way to internalise advice is to actually forget it when you’re told about it, but make mistakes which give you a strong visceral reason to heed the advice next time.
Enjoy!
If you are going to have a difficult conversation, do it in person or over a call, not in writing. It will be faster, more effective, and less draining. This can apply to a negotiation, some tough feedback, etc.
Praise in public, criticise in private. Remember “everyone is fighting a battle you know nothing about”, do a vibe check before you dive in.
Your roadmap is never done. Practice Bayesian updating: seek new information that challenges whether your roadmap is right at any give point, and adapt to this new information if you have to (even if this leads to difficult conversations resetting commitments).
Give your team the permission to overperform. If you follow certain agile methodologies to the letter you give your team members an ‘upper bound’ on what is expected of them. Encourage those who want to do more that they should. Publicly celebrate this ‘overperformance’, and inspire others to have this level of impact. There’s nothing wrong with it!
(I wrote a dedicated post about this here.)
When it comes to nailing product-market fit, empathy > passion“, from Scott Belsky, is spot on. The big vision is great for raising funds and hiring the team, but getting to product-market fit is unglamorous: it takes 100s of conversations, analysing jobs to be done, validating product features, etc.
When it comes to investing, time in market not timing the market.
“Coopetition” is the norm. Companies that compete are often talking to eachother and partnering on other things. Always keep the communication line open, you never know.
For example, Apple and Google compete on the smartphone market, voice assistants, and many other things but also have huge deals going like the Safari default search engine. Shopify own 13% of Flexport but have started competing with them.
Find out what you are good at, and what energises you, and lean into it. Do more of it, let others know this is what you enjoy, it’s ok to be better at some things than others – the team is here to complement you.
Avoid sending important stuff on Friday afternoon, your engagement rate will be low. Unless it’s urgent, schedule it for Monday morning and it’ll be much more effective.
The more senior you get the more you have to become a parrot 🦜 . You will find yourself constantly repeating messages, and that’s ok. It’s necessary.
Ernest Oppetit 