Dear 2004 Matt,
This is future you writing from 2023. Here’s a bit of advice about managing up. You’re a smart guy, and you’ll have a lot of great ideas, but your political naiveté will cause problems. So here's a few thoughts about the politics of managing up.
When things go wrong your first instinct will be to keep it quiet and solve it all yourself. Don't. Secrecy is actually the wrong approach in that situation.
Think about it from your boss’s perspective. Senior leaders are frustrated because they don’t have full visibility into the org. They know problems abound, but they only hear the good news, until something boils over. This undermines their trust in the team – they question whether their managers are making the right decisions. Most times senior leaders appreciate transparency.
Therefore, if you over communicate, even the bad news, they’ll find it refreshing.
Here’s what I’d suggest:
Over communicate in-general – Send regular updates on important projects, including data. That’s a chance to remind them of your top priorities and KPIs. Plus, when you do need to communicate bad news, it won’t be out of the blue, it will be part of your regular cadence of updates.
Share bad news – They don’t like bad news, but they hate surprises. When problems get brushed under the carpet, that’s when they get annoyed and suspicious.
How to serve the bitter pill – When you do communicate bad news, remember 3 things:
Assume everyone has positive intent and avoid blaming anyone. (They’ll figure out who to blame, don’t worry.)
Explain what you learned, so nobody else makes the same mistake.
Most of all, offer solutions. I’ll repeat that: Never bring your boss a problem with out your best guess at a solution.
Matt, I know this sounds scary and uncomfortable, but trust me, it works. Most leaders are surrounded by “yes men” (and women) and get the best version of every story. But they know problems abound, and they will find your honesty refreshing.
Just make sure to do it right:
Assume positive intent
Share the learning
Offer solutions
As for the source of this great advice, you can thank a brilliant guy named Marcin Zaba, a mentor you’ll meet in 2017. Stay in-touch with him!
I hope this helps!
P.S. Buy Google, Amazon, and Bitcoin as soon as you can, and hold them until November 2021, and none of this will matter!