What Leaders in Tech Wish They'd Been Told

Written by: dgiordano
7 min read
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You may have noticed that we've chatted with a lot of really smart people through our Inside Look interview series. As we wrap up 2015, we're revisiting some of the sage advice we've encountered from these founders, CTOs, and engineers.

If you really want to know about a smart person's journey, ask them about their mistakes or what they've learned. This week, we take a look at some of the best answers we've received from leaders in tech when we asked what advice they'd give their former selves -- or anyone else starting out with the ambition to build something difficult and important.

John Sheehan, CEO of Runscope

Prior to starting the company, I think the biggest advice I would tell myself is get really, really comfortable with rejection. You think once you’re done raising money, that’s it. You think, ”Hey, I got rejected 49 times, but one person did not reject me, and therefore we got the funding.” You think you’re done with the rejection. Then you find a really great candidate, and you get all the way to making an offer, and you get rejected. It stings. Or you get really far down the path with a prospective customer, and they go with a competitor. I’m never okay with it, but I think it’s taken a long time to become more tolerant of the rejection.

Startups are 99 percent being told no. If you’re impatient like me, that does not always feel like progress. So, try to get comfortable with rejection as early as possible.

Dan Kador, CTO of Keen.io

Preserve your sense of possibility. That sense of being naïve and just assuming that, “All right. Well, I’ll just solve whatever problems come up,” and, “I don’t need to know everything” is an incredibly valuable thing. I don’t think I would want to change that. If I went and told myself three years ago some of the stuff I know now, it’s possible that I wouldn’t’ve started the company. Or it’s possible that I would’ve done things very differently, because there’s a lot of good stuff when you start a company, but there’s a lot of bad stuff, too. The roller coaster’s a real thing.

I think that preserving that sense of possibility, being naïve, is really valuable. I don’t think I would change anything.

Morten Primdahl, CTO of Zendesk

I would say go for it, go crazy. Just don’t lose yourself.

I’m saying that because sometimes I found, in my journey, that I was so much in the trenches that I forgot to pull back and just enjoy it. To see the perspective of things. Sometimes you can sit in your own head, and you spin in a crazy loop. I would encourage anyone to try stepping back to reflect and process. You will never learn as much as you do on this journey.

Brendan Schwartz, CTO of Wistia

It’s easy to make things more complicated than they need to be, in anything. There’s a tendency to view the unknown as magical, to assume the elements you don’t understand are really complicated. As a result, it’s easy to overcomplicate your problem-solving.

With Wistia, there were plenty of places where we assumed things were more complicated than they were, and so we created over-complicated solutions to match, instead of stepping back and evaluating. What you’re trying to do is probably not as complicated as you’re making it out to be.

For instance, when we raised some angel money, we suddenly thought we had entered a new, more serious echelon of business. And so we started playing office—we felt we had to be more professional, hold mock board meetings, etc. We found ourselves waiting until those official meetings to make big decisions instead of following our instincts and just solving problems as they came up with the team. It was ridiculous and got to a point where we finally asked ourselves: “Why are we doing this? We’re making this harder than it has to be.”

It’s good to have that moment of clarity. Don’t let the expectation of complexity cloud the problem in front of you.

Peter van Hardenberg, founding developer of Heroku Postgres

I’ve been very fortunate. My whole career, I’ve basically followed a strategy of never being afraid to say yes to an interesting opportunity. Nothing I’ve ever done has been planned far in advance. It’s always been about recognizing a new opportunity and following it when you see it. That used to worry me more than it does now, but if I had tried to plan my career, I certainly wouldn’t be where I am right now.

So, I would say: take opportunities, feel comfortable with the uncertainty. It’ll all work out.

Laura Frank, Senior Engineer at Codeship

I wish that someone had emphasized that it’s okay to fail. Especially in the USA, kids are taught that failure is bad, and we have things like participation ribbons so everyone feels like they won.

The truth is that engineering is hard. You’re going to make mistakes. You’ll introduce a bug that will have PagerDuty light up at 3:00 a.m. It’s okay. You need to make mistakes so you can learn from them. Most of the reason why I got really interested in computers as a child was because I saw it as a mechanism for solving problems, but I didn’t always have the right answer. Even as an experienced developer, I still screw up and do the wrong thing.

But all of those little failures eventually lead to successes. Tinker and break stuff; it’s the only way you’ll learn how to build something the right way.

Elliot Cohen, CTO of PillPack

One of my uncles said this to me when I was growing up: “There’s owners and then there’s employees. Only hire owners.” I have tried to follow this advice, and I would give it to myself again today if I were starting over.

You’re trying to build something that doesn’t exist. [...] There is always going to be more to do than you realize, you’re going to forget stuff, and stuff’s going to fall through the cracks. The only way to prevent that from resulting in a poorly functioning company or poor customer experience is to surround yourself with people who are equally passionate and motivated about solving that core problem and feel a sense of ownership over it.

You have to find people who are dying to work with you to make that thing come into life. You want those people to be real owners. They will always be the ones who step up and take ownership over something, take responsibility for it. They will tell you when they think something is broken and needs to get fixed or they’ll just go fix it themselves. And you want to surround yourself with owners.

Jessica Suttles, CTO of Vektra

I feel like somebody might have said this to me, but I didn’t really know how to take it to heart at the time. But just the fact that nobody knows everything. There are things that everybody doesn’t know. Just starting off, it was so intimidating to be around more experienced developers and just thinking that they always had the answers. But now that I’ve been around developers more and more, I realize that a lot of the time, nobody has the answer until they’ve gone and done the research or tried something out.

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