@jakecalabrese.com
🌍 Helping leaders create environments where people thrive and great products emerge | 🎶 Concerts keep me sane | ⛺ Mountains call often | 🛼 Skating is just dancing with wheels | 🕺 Always down for a dance party
You got promoted because you were the expert. You knew the answers.
That's exactly what stops working when you become a leader.
You haven't done the day-to-day work in years. Your team knows more than you about their areas. Let them find the answers.
Every action you take is a policy.
Skip the meeting? You're saying it's optional.
Email at 11pm? You're saying that's expected.
Never ask for help? You're saying it's weakness.
People watch what you do far more than they listen to what you say.
At a certain level, you're supposed to know everything.
That's the unspoken rule. And it's nonsense.
Many leaders are afraid to ask for help—not from arrogance, but because the org expects them to have all the answers.
When YOU ask for help, you give everyone else permission to do the same.
"Legal needs this by Friday."
Watch how fast everyone stops asking questions.
There's a whole vocabulary of "scary words" used to fast-track approvals: SOX, HIPAA, FDA, "quality flagged this."
My advice: Don't just roll over. Ask what's actually required.
Trump cares most about the markets. The best strategy is to opt out.
We’re asking you to join a monthlong national economic strike targeting tech and AI companies. www.resistandunsubscribe.com
The best tool we have to push CEOs to take on the president and prevent further erosion of the American brand is in our pockets — an economic strike that builds on calls for Apple boycotts that are already starting to emerge.
Every organization has launched improvement initiatives that faded after six months.
New process. Big kickoff. Slow death.
The missing piece is almost always: who owns making it stick after the excitement wears off?
