I joined PagerDuty in 2011, back when the entire company could split a large pizza and still have leftovers. I left more than seven years later, as we were preparing to go public. Now, almost 7 years in the rearview mirror I’m dumbfounded by how much I didn’t know when we started. I learned a lot by doing, and more than a little from my own mistakes but I also got a lot of advice. Here are some of my favourite pieces of advice I got personally:
“Yup, it’s tough.”
I don’t even remember the specific problem I was working on when I got this one. I’d like to think I was grinding through something tricky, but the truth is I’d probably drifted from problem-solving into whining. The actionable advice was just three words: “Yup, it’s tough.” That was the advice. Some things are hard. That doesn’t make them optional. You still have to solve them.
“Sometimes it’s you.”
We’ve all been in that meeting where a problem is sitting in the middle of the table, and everyone is politely waiting for someone else to pick it up. Early in your career, you don’t feel like it’s your turn yet. You assume someone more senior, more official, more something will step in. But sometimes, whether you realize it or not, they’re waiting for you. If you’re in the room, you’re a candidate for solving it.
“Keep track of your bank accounts.”
This one took a while to sink in with me. Every time you help someone out think of that as a deposit. Every time you need something from someone, consider that a withdrawal. The trick is to never let your balance go negative. This doesn’t apply to everyone but the people who keep score usually aren’t the ones who say so out loud. There are two sides to this one though, the advice-giver meant it from the perspective of getting things from people but it also struck me as a good description of who I don’t want to be. I try to find a way to help every new employee, just in case they are looking around fretting at starting with an empty bank account.
“Time to first referral.”
I think I had just given an offer for a PM that was turned down, we were talking about when you could be confident you’ve landed a candidate: was it the verbal? the signed contract? butt in seat? The best answer “When they refer someone.” That might be a stretch as a hard metric, but I loved the clarity of it. It moves the goalpost from “they joined” to “they believe in us.” It’s something you can track and aim for,
“Slow down. Simplify. Repeat. Repeat again.”
This one came to me in every possible flavour. “Focus the message.” “Say it again.” “Say less, but clearer.” I needed it more than most, but most people need it more than they think. It’s easy to confuse “heard” with “understood” (Or even “was facing you while you said it” with “heard it.”) Whatever idea you’re trying to communicate,your audience will absorb less than you think. And if it’s important, once is never enough. Clarity is a function of what got absorbed, not what got emitted.
“Show me.”
A great idea doesn’t count until it exists. I pitched some can’t-lose idea to a new executive. Their response? “Show me.” That was the bar. Not the pitch — the thing. Show the MVP. Show the signal. Show that the idea has legs. If you can’t demo it, maybe it’s not real yet.
“Be coachable.”
Everyone says they want feedback but far fewer people take it. The thing I didn’t appreciate early on: most people want you to succeed. They like helping. They’ve been through things you haven’t yet. Some of the advice will be wrong — but if you ignore it all, you’ll miss the part that could’ve saved you six months. Stay open. Everyone knows something you don’t. The best people aren’t just smart — they’re coachable.