Thread by @BrandonMChu

Leading large teams over the past few yrs - the most in my career - has been rewarding, but also very challenging

I'm lucky to have been given that opportunity, but it's still hard, and walking an infant around the kitchen counter 1000x on pat leave helped me reflect on why 👇

1. The scale of responsibility to employees is serious - people's lives are in your hands, and it's not just their income. People move across the world and uproot families for a role you create. People take massive risks in their careers for an opportunity you pitch them.

2. The scale of responsibility to the business is serious - at one point last year, I napkin math'd that payroll under my stewardship was $40MM annually. I stealth threw up.

3. The scale of responsibility to customers is serious - especially on a platform like Shopify that empowers businesses, you are legitimately responsible for the lives and well being of your customers and business partners in a tangible way.

4. You have to standby and communicate the WHY for everything the company does, in a way that's coherent and aligns with the culture and values. This is hard when sometimes you don't agree entirely (of course, if this happens often, you should not be there).

5. You need to show up emotionally composed, everyday. This is draining because once you pass 150 people, the odds are that any particular day will be a crisis for someone on your team. Yes, you should ideally be able to be vulnerable too, but real talk you mostly can't.

6. You have to keep "winning" in order to provide opportunity for your team. This is intuitive to founders, but if you don't keeping getting promoted or increasing scope, then where's the space for your team to grow? You better win, or they will (rightly) leave in the long run.

7. You need to create a safe, equal-opportunity environment for your team, even though you know that will almost never be true, because there is always some bias in large groups. Even with the best of intentions and effort, if people aren't being fairly treated, that's on you.

8. You will never be perfect, and many on your team will think you're a bad leader. Harder still, due to power dynamics you will rarely get the truth told to you directly so it's hard to adjust. The way to live with this is to be principled, consistent, and accept the outcomes.

9. You hold the standards for the organization, and have to be the one to tell people "this isn't good enough" even when you know they worked their asses off. This applies to product quality, employee behaviour, and who gets promoted.

10. Finally, you always need to put up a front as the leader. To your team, to your peers, and to your bosses. It can be draining and lonely.

At the same time, leaders don't deserve sympathy, because it's an incredible privilege that many would dream of having. still hard tho