ICYMI: Meet Allan Leinwand, Slack’s SVP Engineering

October 15, 2020

Welcome to In CASEYou Missed It, where I take a brief break from my Weekly Walks to get to know some of the most interesting and innovative personalities behind the greatest startups in the world.

This time I met up with Allan Leinwand, Slack’s SVP Engineering, to chat about Hamilton, the best part of his job, and the secret to managing Slack messages like a pro.

How do you explain what you do to parents, friends, kids and non-industry people?

If you asked my daughter what I do, she’d probably say I help build Slack, which is true. My two daughters understand what Slack is and they understand what we do, because people are used to iMessage or WhatsApp and other messaging tools.

People will ask me what I do, and I say, “I help run engineering teams at Slack. And one way to think about Slack is to think of it as a version of WhatsApp or iMessage you’d use inside your company.” I also tell them about how Slack helps me drive work, gets me out of email, and helps me organize what I’m doing on a daily basis.

What’s the best part of your job?

Growing leaders. I get inspired by finding people who come into their own world, who learn how to manage teams, who handle complex projects—I love to give them advice and coaching, and to really delegate hard tasks to them and let them take off and run with them.

Related read: Leaders Eat on Camera: Advice from 10 Years of Leading Remote Teams

That’s really my favorite part: When I know there’s this hard, complex, multi-phase project, I can hand it to somebody. They come to me periodically, but I know they’ve just got it. The best part of my job is to be able to find those leaders, groom them, and watch them excel. It’s just awesome.

If there were no internet, what would you be doing?

I dreamed of being an airplane pilot when I was younger. My goal was to say over the airplane intercom, “Good afternoon, ladies and gentlemen. We’re traveling at 37,000 feet.” If there were no internet, that’s probably what I’d be doing.

In your opinion, what are the most important qualities of a leader?

Something I look for in my leaders is clear and linear thinking—leaders who can articulate a problem in a very clear, concise manner.

I also look for my leaders to be transparent. In other words, “Don’t hide the ball” is what I like to say. If there’s some bad news, just come tell me. If there’s some good news, come tell me. Let’s be transparent with each other, and let’s make sure that we’re clearly communicating. That builds trust and with trust comes efficiency and productivity.

The last thing is empathy. I try to understand what people are going through, because sometimes everyone needs help. I often need help. I tell people that we have gray matter, therefore we’re faulty creatures and should help each other. I try to understand what people are going through, let them express frustrations, and have us work out things together.

I also sometimes express what’s going on at the executive leadership level at the company so they can understand and they can internalize it and bring it down to their teams. It’s a great quality of a leader who can take the big picture and make it relevant for their teams.

If there were a movie about Slack, who would play you?

That’s an easy one for me because I’m a huge Hamilton fan. I’d want Lin Manuel Miranda to play me. I can imagine the Slack movie being a musical—and if he wrote it, I’m all in.

Who is your favorite superhero?

I didn’t grow up with superheroes and being a big superhero fan, but I’d pick Lego Batman. I thought the movie was hysterical. Lego Batman voiced by Will Arnett is classic.

Was there a book or TV show that you loved as a child and wished you could have been a part of?

My favorite is The Great Gatsby. I’m a huge F. Scott Fitzgerald fan—I’ve read everything he’s ever written.

Living in F. Scott Fitzgerald’s world would be a lot of fun. Interestingly, think about this: That was the 1920s, and they’d just passed the first world war and the last major flu pandemic. I have this sneaking suspicion that if we ever get out of our current pandemic, the next few years could be a lot of fun.

Do you have a favorite podcast?

Hardcore History by Dan Carlin. He dives into historical stories, all factual: World War I, World War II, back to the Roman times and even Attila the Hun. If anyone is a history fan, I strongly recommend it. And the podcasts aren’t small commitments. His World War I is called Blueprint for Armageddon. It’s a six-part series, and each part is probably three-and-a-half to four hours. Trust me, it’s worth it.

Is there a tool you’ve discovered in the last year that has made things easier for you?

I think the most powerful tool for me in the past few years has clearly been Slack. I was a Slack user at my previous company, but it’s really changed the way I work monumentally since I’ve come to Slack. I don’t do email anymore, which is just a bizarre concept. The emails I do are with external people outside of Slack, but even that’s going away with this feature we have called Slack Connect where you can connect multiple businesses together.

For me, it’s been a really interesting change. For a number of years you’d wake up and you’d begin to check your email, and you’d expect your inbox to scroll to 20, 30, 40 messages. And that’s how you’d start your day.

Working at Slack, you fire up your inbox and there’s nothing there—and you wonder if you’re still employed. And then you go to Slack and you see all the messages there in channels that are focused on specific topics with full transparency to the right members of the team. No more different email inbox views for everyone that can lead to misalignment and loss of productivity. It’s just a completely different cultural change.

How do you manage your Slack messages and channels?

On my very first day at Slack, I went through our onboarding experience and learned about the 10 or so standard emojis that Slack uses. Having teenage daughters, I immediately rolled my eyes—I thought, “Emojis, really? I’m going to go work with emojis.” But the truth is, they’re amazing.

In the morning, I wake up and check my Slack, and I see all these channels that are lit up. But instead of having an email inbox—it takes effort to go through every single email, even if you’re just saying, “Thank you, got it,”—in Slack there’s the use of emojis and the ability to manage the inbox of requests with a thumbs up, a green check mark, or we put eyes on things to say that we’re going to read it later.

You can blow through that at an amazingly quick pace if you have a standard set of emojis to manage reactions and manage how people understand your input.

For channels, I use our Collections feature and group things by topic. I also turn off most notifications except DMs and key channels, such as those involving customer incidents. Managing notifications in Slack is something that is easy to do and definitely worth your time. I also strongly recommend scheduling your Do Not Disturb times to give you some downtime.

What’s something you’ve learned this year that you think everyone should know?

The most important thing that everyone should understand is that there’s a personal life and a work life, and we’re seeing them blend together a lot. We need to be able to be a little more open and transparent about that.

So what I’ve learned in the past six months is there’s a fine line between people’s work lives and their personal lives. I’ve also learned that when you get a peek inside someone’s personal life, it makes them more human. And it also makes it easier for you to work with them.

Read more interviews with the most interesting humans in SaaS

Partner at OpenView

Casey leads the end-to-end strategy & programming for OpenView’s network of industry experts, advisors & corporate partners. Her role is focused on creating connections between founders & their teams and the partners, advisors, board members & events they need to reach their goals. Additionally, she manages the OpenView portfolio peer networks and hosts the #WeeklyWalk series.