Managing Timelines

"Figure out, maybe the night before, the one thing that you want to get done in your day, and then at the earliest opportunity, just try to give yourself five minutes on it."

"Something we've done over the last year is really kind of moved to a model of talking about dates and promising and committing to dates that are within our control. And so, if you think about the product development life cycle, we can commit to a discovery effort... we've gotten a lot better at making the commitments around the work that's right in front of us versus making a commitment around a project six months out when we haven't even done enough discovery."

"What I'm seeing is that the time to first demo is much shorter, but the time to a full deployment is going to take longer. So I think that there's going to be an uneven cadence. So typically, I think there was much more of a you've been this thing, you take a few weeks and then you can iterate and so on. But that inner loop of prototyping and iterating and getting even user research through AI conversations, all of that gets shortened. But I think the bar for scale, therefore becomes much high."

"I had a head program manager that would score all the projects. Either they're green, yellow, or red. Meaning they're on track or not on track to ship... I use the reviews of the work every single week. And the reason there's not a lot of bureaucracy... is I'd review the work and if something wasn't happening, then I would stop the meeting and say, 'Why isn't this happening?'"

"If timelines are maybe not well reasoned through from first principles and perhaps there's padding that has been well intentionally added by different folks, you have to understand fully, okay, what are the assumptions of how long things will actually take and what is a padding? Then, really work through that with the team."

"When you're building out an SEO effort, and I'm going to keep going back to this, it's a product. So you're building out a product and you're creating milestones... Now, if you start missing all those milestones... you can point very specifically to all those milestones that were missed."

"There's heavy Jira automation... making sure that you have really good process around how are you going to run so many experiments... We're planning months out, as we think about these feature iterations, even small ones, feature iterations, because when you lose cycles, not pushing on a feature, it's just sort of lost opportunity."

"We have these things in Basecamp called hill charts. And things that are on, that's actually work... A project's more like a hill. It's not like a linear line. If you're on the left side of the hill, it means you're still pushing this thing up the hill. You're still trying to figure out how to do this. But once work gets to the top, it's downhill from there. It's just pure execution and we know how to nail it."

"Your job is not just to keep people going on momentum. Your job is to make momentum. And sometimes that momentum has to be manufactured. And that has been one of my biggest lessons on just how, as leaders and people starting companies, how do you force yourself? And sometimes when it's early on, you're actually just doing it to yourself, creating manufactured deadlines and launch dates."

"The only way to make deadlines real is to take them so seriously that they are basically like a P0 problem, and everything else has to not matter in comparison to the deadline because that's the only way you're going to be able to signal to the team and also to all the stakeholders that you're actually taking it seriously."

"We do almost no estimating in order to hit deadlines. What we do is we ship as early as we can. The thing we talked about earlier where if by the time that 10% of the time has elapsed, you have a working thing, you can now spend the rest of the time deciding whether or not you want to do another iteration or you want to polish that thing."

"tasks take people three times longer to finish than they estimate. Why does that happen? Because when you say, 'Okay, here's that thing on the to-do list. I'm going to work on that and see how long it takes me to get it done.' So, you work on it for five minutes and then you get an email and then you get a notification... you never actually track how long that thing took you to finish"

"The thing about projects is when you run out of time and you run out of money, the project is over. Don't run out of time, don't run out of money. Good intentions are no reason for an extension. The professional doesn't ask for an extension because the professional understands that things you didn't expect are going to happen."

"We have this calculator that we look at that says, 'How much time are you spending in meetings?'... All right, next quarter, it's red again. All right, now maybe we need to start having the conversation of, what this new hire will take over."