Secrets to Maximize Your Productivity with Josh Silverman

INTRODUCTION: Welcome to The Daily Bolster. Each day, we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, I'm co- founder and CEO of Bolster, and I'm here today with Josh Silverman. Josh is the CEO of Etsy. He is leading the company as it builds a platform that empowers creative entrepreneurs around the world. Josh has over two decades of leadership experience, including growing consumer technology companies, scaling global marketplaces. He is a tremendous CEO and I've had the pleasure of getting to know him over the last five years or so. Josh, welcome to The Daily Bolster.

Josh Silverman: Thanks. Happy to be here.

Matt Blumberg: So my question for you, one of the things that's always impressed me as you and I have kind of talked and shared stories and tips and techniques over the years is how methodical you are about maximizing productivity and time, both you and your team. So I would love for you to share with our audience your kind of top three tips for that.

Josh Silverman: All right, so three tips. Focus on the vital few, come to meetings prepared with a purpose, and team time is critical. So let's start with focus on the vital few. The objective is not to figure out the good ideas. The objective is to figure out the fewest most important things you need to do in order to succeed. And that requires actually having a very clear definition of success. So start with a very clear definition of success, which often is harder than it sounds, and then figure out the very fewest battles you need to win the war. And that allows the entire team to double down with boldness and urgency on what we call the vital few versus the worthwhile many.

Matt Blumberg: I love that framing. One of the things I know you and I have talked about is trying even to get it down to one if it's possible. I know it's not always possible.

Josh Silverman: I find having one metric that matters more than every other metric is very important because you can then say, what are the fewest things that are going to really move that metric in a very big way? If you have 10 success metrics that are all roughly equal, you're going to discover there's four or five initiatives for each of those. And before you know it, your organization's trying to do 40 or 50 things. And that to us looks like the worthwhile many, not the vital few.

Matt Blumberg: All right, vital few. What's next?

Josh Silverman: Second is come to meetings prepared with a purpose. So I spend hours every day preparing for tomorrow's meetings. My calendar, if you look at it, has large blocks of time that are blocked for pre- reads. It's essential that I get a pre- read before every single meeting. I need it 24 hours in advance. The reason is, for example, there's decision making meetings, accountability meetings or problem solving and brainstorming meetings. Many of the meetings I'm asked to attend are decision making meetings. I'm going to be asked to make a decision, and so I want to make sure I come into that meeting already having thought through, " What are the alternatives? What are my questions? Do we have the right points of view in the meeting? Is anyone missing from the meeting? What alternatives are in the marketplace that may not have been considered?" And I ask all of those things in advance through asynchronous pre- reads, so by the time we're in the meeting, we're very, very focused together. Meeting time is expensive time. One thing you won't see at Etsy is folks reading a deck to each other. That is a giant waste of time.

Matt Blumberg: Total waste of time. Yeah.

Josh Silverman: So walk into the meeting and the expectation is every single person has read the materials in advance, has thought about it, and we get straight into questions, discussion, and ultimately decisions.

Matt Blumberg: I love that. And actually, I really like the upstream work that you do to define a type of meeting, right? Is it brainstorm, is it decision, et cetera.

Josh Silverman: Yeah. And those three tend to be the three that I find-

Matt Blumberg: Yeah. So say that again. It was brainstorm, decision or?

Josh Silverman: And accountability.

Matt Blumberg: Accountability.

Josh Silverman: A lot of meetings of you have accountability, right? It's a checkpoint. It's, " Are we on track?" And for those, the format of that meeting should really be red, yellow, green. You can eyeball the greens real fast and just spend your time on where are the roadblocks, where are the yellows and reds. And even there, we don't spend time in our accountability meetings trying to solve the problems. We just identify that we have a problem and ask a team to come back with solution.

Matt Blumberg: Okay. What's number three?

Josh Silverman: Number three is that team time is critical. When I inspected my calendar years ago, I noticed I was spending a lot of time in one- on- ones. If you have eight direct reports, you might spend eight hours a week. That's a full day a week, and one- on- ones with your direct reports. And when I looked at what I was doing in those one- on- ones, they were usually giving me updates on status or they were asking me to make decisions. The status updates are often best served when the entire executive team can hear that together. And decisions are usually best made with more points of view in the room. It's rare that my direct sometimes, but most of the time there should be more than just one direct report's voice when making a decision. And so I now do far fewer one- on- ones and spend more time collectively as an executive team. We meet three times a week for relatively light touch points, but where we go through progress problems and plans very quickly, lightning round around the table where we give each other updates. And I find that the collective benefit of all of us talking together is way better than one- on- ones. And it frees up a lot of my time to not be in one- on- one so that I'm available for the ad hoc meeting, for things that come up during the course of the day or the week when my attention is more urgently needed.

Matt Blumberg: That was not only great, that third one, but you buried in it one of my favorite tips, which is inspect your calendar.

Josh Silverman: Yeah.

Matt Blumberg: Periodically you actually have to download it into a spreadsheet and figure out where you're spending your time. Otherwise, you have no idea how to shape how you're spending your time.

Josh Silverman: Yeah. In fact, I'll often set, here's the priorities I need to accomplish over the course of the week or the quarter and work with my assistant on a pie chart, a budget of how many times should be allocated. And if it's the same every quarter, something's probably wrong.

Matt Blumberg: That's exactly what I do. And it's a great tip. Josh Silverman, this was lots of bonus advice, but thank you so much for being here to talk about maximizing your productivity and your team's productivity.

Josh Silverman: Great to be here. Thanks for inviting me.