Interview with Rob Walling on Delegation and Staying Productive With a Remote Team

If we all had the opportunity to go back to where we were at just a few years ago, I imagine we would have at least one piece of advice to share with our past selves that would eliminate unnecessary mistakes and wasted time. When you’re in the moment, you don’t really think about how certain actions (or a lack of actions) are really impacting you. Hindsight is always 20/20, though.

I recently had an opportunity to talk with Rob Walling about Drip, an email marketing automation platform launched in 2013 in an increasingly-competitive space, and how his productivity has increased over the years as he grew and learned from his errors.

Staying Productive With a Remote Workforce

Sujan: How about a quick introduction, Rob?

Rob: Sure. I’ve started several software companies over the years and founded a company called Drip three years ago. Drip was just acquired by Leadpages about a month ago.

Sujan: I wanted to talk to you about productivity today. Would you consider yourself a naturally organized and productive person?

Rob: I think so. I tend to prefer structure and organization. I’ve always written and worked from lists, even when I was a kid. When I was eight or nine years old, I was cataloging comics and making lists of what I could do to make money and how I would go about buying more comics. That’s generally my mindset, although I certainly struggle with productivity like everyone else.

Sujan: I feel like everyone has gone through that “I have to figure out what is productive for me” phase, and they aren’t naturally good at it all the time. At least, most founders I’ve talked to are the same way.

So, you’re doing SaaS and you’re running a couple of businesses. Do you have a remote staff for all that?

Rob: Yeah. With Drip, we’re about 50% local and 50% remote. With Microconf, everyone is remote. With previous companies, everyone was always remote. I have experience on both sides of it.

The Tools of a Remote Workforce

Sujan: Given your remote experience – and I think a lot of startups are going that route because it’s so hard to find enough good people locally – are there any tools or services that you use to organize your day or manage your team?

Rob: To be honest, I initially resisted using the tools we have now, like Slack. My co-founder Derek wanted to use Slack, but I felt it would be interruptive to everyone – especially since we’re a software company and developers need long, focused periods of time.

Early on, I was like, “I don’t think we need this.” But let the record show that in the end, Derek was right. Slack has changed the game for us, as it has for others – that’s why it’s growing so fast.

We also use Trello, and then we use Zoom for video conferencing with Skype as a backup. Those are the three most common tools we use, along with Google Docs. I worked with a remote team a decade ago and almost none of these tools existed. It was really hard because it was all email back then.

Productivity Quirks – Whatever It Takes to Stay On Task

Sujan: I think Zoom is a great service, and like you said, Skype is a good backup. I’ve heard Google Docs from pretty much everyone that runs an online business. I’ve also heard from everyone that it’s not the tools you have, but how you use them.

What I’ve discovered by talking to these founders is that everyone has a unique style or approach to productivity. For me, I don’t care about my time, but I focus on managing energy. So if I need to step away for three hours in the middle of the day to tackle some big things, I’ll do that.

Is there anything unique that you do that helps maintain sanity?

Rob: Yeah, I typically work in sprints of about 90 minutes, so they’re longer than the typical Pomodoro stretch. When I sprint, I turn everything off. To get ahold of me, you need to break the do-not-disturb on Slack, text, or call me. If you do, it should be an emergency.

I usually have headphones on with music looping, like the same song looping for 90 minutes. It has to be a song I can get into a groove with. There’s something about audio stimulation that is really a key thing for me to get into a productivity trance.

I also use caffeine sparingly. I don’t drink coffee on the weekends, I don’t drink it in the afternoons, or to wake up. When I come in to work, I drink about a half cup. I’m still able to work without it, but I hit peak productivity when I’m hammering something out, like writing an entire talk in maybe one or two sprints.

That used to take me eight or ten hours. That focus time takes a ton of energy out of me and when it’s done, it’s like boom, I’m done for the day. All I can do after that is have conversations and email.

Mastering Delegation to Stay Productive

Sujan: You have this huge team you’ve put together. Can you share how many users Drip has at this point?

Rob: Thousands.

Sujan: So your team is managing thousands of people. How do you handle delegation? I assume you can’t do it all on your own.

Rob: Sprints are a big thing for me, but delegating became a game changer for me like ten years ago. As a software developer, I wanted to do everything myself. That’s just the natural control freak in me. The first time I hired a virtual assistant in 2006, I was really bad at delegating. In my opinion, it’s a learned skill and I had to learn it over a year and a half. The more VAs I worked with, the better I got at it.

Back then, I had no budget and was paying like $5 an hour for someone overseas. I’ve been able to work up to where we now have full-time staff and this changes the game even more. Now it’s not just about delegating one task or thing. It’s about delegating an entire role.

Learning to delegate has been a bigger game changer than any other tactic. I can power through and complete six hours of work in an hour and a half, but it’s not the same leverage as having a full staff of people. There are a lot of time advantages that come from having those people.

Smart Investments in Personal Assistants

Sujan: You made a point that you initially didn’t know how to leverage the virtual assistant. I think people often believe it won’t work for them, but in reality, it’s them and the assistant not knowing how to work together. Would you agree?

Rob: Yeah, absolutely. I’ve recommended assistants to a lot of people and some people who tried it said it didn’t work for them. I don’t buy that; I think it’s a learned skill for most of us and you’re going to have to do it to sort it out.  Also, if you have a budget, hire someone that charges more than $5 per hour.

Sujan: Right, don’t go for the bottom of the barrel. That’s why services like Zirtual exist. The cost is closer to what you’ll pay for a full-time employee, but you get better assistants. You don’t have to teach them anything. I personally work really well with contractors, but I haven’t been able to find a virtual assistant I work well with yet.

Winding Down and Looking Back

Two more questions for you. What do you do at the end of the day to wind down? Is there a routine you have?

Rob: Yeah, I listen to a daily podcast called the Daily Tech News Show. It comes out at like 3 or 4 o’clock in the afternoon, and it’s nice to listen to on the drive home. It discusses what’s going on in the tech space for 40 minutes, and they also talk through the headlines. Its quasi-work because I’m still listening to tech stuff, which I like, but I couldn’t listen to a marketing podcast because that’s what I think about all day long.

Sujan: Awesome. If you could go back in time like ten years or to when you first started out, what’s the one piece of advice you would give yourself to be more sane or create a more productive daily routine?

Rob: I used to kill hours researching and thinking about actions I should take, rather than jumping in and taking actions and just making mistakes. So my productivity was hampered by my hesitation to act. That changed at some point. I got enough confidence in my judgement and abilities, and I learned you had to just do stuff.

Instead of thinking about it, and trying to research every angle online to see what other people think about it, you need to jump in and just be like, “I’m going to do this and if something goes wrong, I’ll just fix it.”

That allows you to do five or ten times the volume because you don’t agonize over every decision. At the end of the day, it just comes down to focus.

What’s a unique way that you structure your day to be more productive? Share your tips with me in the comments below: