OPERATORS: Jason Evanish (Lighthouse) on How to Make Bad Managers Great

by Adam Spector in

The skillset needed to found a startup is very different from the one needed to make your company grow. The Next Big Thing idea is usually explained as a spark, but it’s more like a seed — it must be planted in fertile soil, tended to, and given enough sun and water as it grows. It’s always a few clumsy moves from dying. 

light bulb on black surface

Jason Evanish founded Greenhorn Connect, a hub for the startup community in Boston, in 2009 before selling it to the Capital Network in 2014. That year, he founded his second company, Lighthouse, to fix a problem he’d noticed in his years in the startup space: bad managers. Lighthouse is a tool that helps managers stay on top of everything their team is doing and nail their 1:1s. We spoke with Evanish to learn more about what it takes to be a good manager and what tips he has for founders hoping to grow their businesses. 

AbstractOps: Tell me about the start of Lighthouse and the problem you identified that you set out to solve.

Jason Evanish: The problem that I wanted to solve was making people better managers. I saw that there were a lot of bad managers out there and the thing that bugged me most is that it’s actually not that hard to be a good manager. There’re a handful of things that if you do them, everything goes a lot better.

When I first started Lighthouse, I didn’t really know what it was going to be. I talked to about 40 managers — some were Fortune 500 VPs, some were founders, some were frontline employees, all kinds of different levels. But what was interesting was that very quickly everything drifted into two camps. 

One camp was super experienced managers and they’d all hacked their own systems to help them do the things they’d learned were important. On the other side, there were all these inexperienced managers, bad managers, and struggling managers. Either they said, ‘I’m a Type-A person and I want to be a good manager.’ Or they were like, ‘Hey, some of my team hates me,’ ‘Hey, some of my team is quitting,’ or ‘Hey, my team won’t listen to me.’ 

It turns out, if you got to the root of what was going on, they were always making the mistakes that these experienced managers had already solved. That’s what led us to create Lighthouse.

AbstractOps: What are the handful of things that every manager should do?

Evanish: We found that there are basically three things. First: you have to build rapport with everybody. You have to show you actually care about the person as a human being. Who are they? What are they about? What motivates them? 

For one person, it may be that they have a wife and kid and their family is all that matters to them. If that’s the most important thing, then occasionally asking how their kid’s doing, will score you points and show you care. On the other hand, you may have another employee who’s single and kind of a nomad. Asking them about the next place they’re traveling or how their last trip was will be very meaningful for them. 

I like what Marisa Mayer calls your rhythm, which basically means identifying the routines you have that are super important to your happiness. She talked about how one person had a potluck with their college friends, and if they missed that working late once a month, they’d be really upset. Another employee had a family dinner every Thursday night at home, so the mother always wanted to be home for that. Once you find out what people’s rhythms are, you can make a lot of asks so long as you never mess with the thing that’s their rhythm. As a manager, I can ask you to work late 29 days a month, but that one day a month, I better get the heck out of the way or the employee’s going to be really mad at me. 

Google calls it psychological safety; we call it rapport. The idea is: get to know what’s important to somebody and occasionally ask about it and show that you’re not expecting them to be robots. This can make a really big impact. If somebody feels like their manager is actually looking out for them, that their manager actually cares about them as a human being, it makes a tremendous impact on their engagement at work. This is foundational to everything you do with them as their manager.

With that foundation built, you can now have a real conversation with your employees, which is the second key good managers follow: having good, candid 1-on-1s. 

The biggest problem that our product ends up solving for is the question, ‘What goes wrong in 1-on-1s and how can we make them better?’ 

The first thing we found is that managers don’t ask the right questions. It’s super easy to just make it a status update and just ask, ‘What’s going on on this project?’ Instead, what you want to do is dig into things. Say: ‘Hey, in this meeting, you seemed checked out. Is everything okay?’ ‘Hey, you seemed upset at Tom. Is something going on with you two?’ Or ‘Hey, you’ve been working remotely for 4 months. Do you feel like you’re still effective? What can we do to make it easier for you to work at home?’ 

When else are you going to talk about that stuff? You’re just not going to have a chance. 

In general, as a manager, the number one thing you should be bringing to a 1-on-1 are questions that help you support the team member, not things for you. You should be able to get your status updates in different places. 

We help managers have better 1-on-1s, because if in those meetings you have really effective discussions and then you make them actionable and you follow through on those things, then your meetings get better and better. When that happens, your relationship with your team member will get better and better, and any walls you had between each other will come down. 

AbstractOps: And what’s number three?

Evanish: Number three is career development. In Silicon Valley, the average tenure pre-COVID was around 18 months at a startup. The reason people leave in 18 months is because they show up, they’re all excited to get to know their peers, it’s a hot, new technology, and they’re pumped to be on another rocket ship. But after 18 months, they’re pretty settled in, they have some expertise around their work, and now they start thinking, ‘What’s next?’

A lot of managers make the mistake of only checking in on career goals once a year at the annual review. Unfortunately, if you do that, during the 2nd review you might say, ‘Hey, is your career goal the same as it was a year ago?’ Now the employee is thinking, ‘Ugh, they don’t care at all about my career. And oh, by the way, I just got beers or lunch or brunch with my friend, and they’ve got this really exciting startup. They’re doing exactly the new hot thing I’d like to work on.’ Now your employee leaves and you’ll be thinking, ‘What happened? How did I lose a really good employee? They seemed so happy. They were enjoying our perks, coming to team events and then they left.’ 

Well, you lost them because good people want to keep growing. If you don’t show them the path at your company — and if you’re a hyper-growth startup, there’s an insane amount of internal opportunity — they will leave and go to the next hot company instead. 

You don’t want to create the vicious cycle of really good people coming in, doing one specific task, accomplishing that, and then leaving. You should be helping them find the next great opportunity at your company. 

AbstractOps: We focus a lot on early startups. As a two-time founder, you have a specific expertise from which to talk about the keys to early startup leadership. What’s the biggest pain point for managers attempting to go from an early-stage to the next stage of a startup?

Evanish: One of the most popular blog posts that I’ve ever written is called, “Why Everything Breaks at 25 Employees.” As you approach that milestone, a lot of things break. Systems that worked when it was all of you sitting around one table in a coworking space do not work when you have 20-25 employees. 

Now, every department is their own team: you may have 8 engineers and a marketing team of four or five. Suddenly, the way you did things — with marketing, sales, engineering and product just sitting around a table and making a decision together — doesn’t work anymore. You can’t actually let everyone have input on everything. And that’ll only get worse as you go to 30, to 40, to 50 employees. You start to have to have departments and need some hierarchy. 

You also can’t have everyone report to you anymore. It’s really great early on when everyone has access to the founders. But as you scale up, suddenly you’re trying to raise your next round and you’re trying to hire 5-10 more people and you’re trying to build new partnerships; how are you possibly going to handle ten direct reports, too? You’re not. Which means you’re going to shortchange managing your team, which means they will get frustrated and you won’t even realize it. 

I’ve had many conversations with founders where they get to this scale and they don’t understand why everything is breaking. They can’t do the things that were working just 6 or 12 months ago and everybody they’re managing is quitting on them. 

And it’s not because you’re a bad person; it’s because you have to acknowledge the fact that in order to take care of your employees, you need to hire or promote someone who cares about management and who can do a really good job with them. You need someone who can come to you and say, ‘Joe has this problem and Tina has this problem. Shane has this problem and Anjit has this problem.’ And you say, ‘Okay, I can help you with that. What do you need? I’ll give you the budget to take care of those issues and get you what they need.’ But you’re not going to be the one who’s on the frontline — you’re just going to manage the managers. 

Adding that first layer of management ends up being a really big pain point and challenge for managers. 

AbstractOps: Ever since the early 2000s, there’s been a Church of the Founder in Silicon Valley. There’s clearly a different skill set needed to start a company and to run a company. How important is it to find a manager who is skilled at operations if you’re a startup founder?

Evanish: Not every founder has management in their DNA. A great example — and hopefully he won’t be offended by me dropping his name — is Dharmesh Shah of Hubspot. He’s a very public, very successful example of somebody who is a co-founder and the CTO who also gives lots of internal and external talks on behalf of the company who, as I understand it, manages either very few or no people. One of the important things founders have to do is know what their strengths and weaknesses are and know what they’re predisposed to do. If you’re a founder and you’re like, ‘Management’s not really for me. I don’t like dealing with people issues,’ then you need to run towards that problem, not away from it. 

Because if you just hide from that problem, you’re going to have a bunch of people reporting to you that are really underserved and upset. But if you instead say, ‘I am not a good manager. I should hire somebody to do the things I’m not good at and I should use my other superpowers for the benefit of the company,’ that can be very powerful. 

This happens a lot for engineering technical co-founders. If you look at Silicon Valley, there are a lot of different ways that a CTO’s role can evolve. They may hire a VP of Engineering and that VP of Engineering may do all the management and hiring. Or the CTO may do all of that, and the VP of Engineering may be the architect and helps map out all the technical details. 

Because once you get to a certain size, you have to split up roles. Nobody can have every responsibility on their plate. So, the nice thing about being a founder is that if you’re self-aware about that and you’re willing to acknowledge your weaknesses, you can hire other people to do those things. Knowing what you need to succeed and hiring people to do the things you aren’t good at is a good muscle to develop.

AbstractOps: How do mantras like “product is king” and “move fast and break things” avert the focus from the nitty-gritty of operations at a young company?

Evanish: One of the hardest things about startups is that there are things that you need to do or they will hurt you long term, and there are things you have to do or you go out of business in a month or two. So, as challenging as it is, you have to keep one eye on the task you need to get done today, keep one eye on, ‘Are we getting a product-market fit? Are we hitting scale? Are we growing fast enough?’ and then somehow, you have to keep another eye on, ‘Hey, are we on a long-term good track so that if we make it, we haven’t made any major mistakes?’ 

The challenge that you face is that there are these important hair-on-fire needs that you have to solve: ‘We have to ship this feature or we won’t close this contract! And if we don’t close this contract, we don’t hit our number! And if we don’t hit our number, we won’t get the next round of funding!’ But oh, by the way, if I burn out all of my engineers, we’re also screwed. 

So, you have this constant push and pull, and I think it’s important for founders to recognize that there is a balance to strike. Sometimes that balance is 80-20 and sometimes that balance is 99-1, but don’t underestimate how important that 1 is. 

If you just crushed all your engineers to get a feature out and they’re all totally burnt out, it’s really important that you’re like, ‘Hey guys, none of you are coming to work on Friday. I don’t want to see your faces. I don’t want to see any activated green dots on Slack. I want you all to get out of here. I want you to have a long weekend and relax and recharge.’ Even small things like that can make a really big difference when everything else is like a death march towards trying to survive. 

The challenge for people is that it’s really hard to hold onto both short-term thinking and long-term thinking at once. 

But I’ve learned that if you can be a good manager, your team will stick with you a lot longer than they would otherwise. Because when the going gets tough, you want to help out people who’ve been loyal and helpful to you. I think Ben Horowitz puts it best: “Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong. Things always go wrong.”

You have to realize that how you treat your employees when things are going well is going to be very important, because that will determine how many people will stick with you when things get tough. And every startup goes through tough times. If you do make it to the other side and start to be a great, successful, hyper-growth company with great product-market fit and really happy customers, being a good manager will mean you actually have a team that’s stuck it out with you.

If you need help being a better manager, you can get a free trial of Lighthouse here. And to automate your back office, sign up for AbstractOps