How to successfully run a remote team

Ryan Carson says that a single mistake cost him $40,000.

Ryan, founder of educational site Treehouse, says the worst part wasn’t even the money. The most painful part was that “I wasted six months and allowed our competitors to get six months ahead of us.”

So what was his mistake?

He didn’t realize he actually needed to manage a remote team member he’d hired.

When you hire a local employee, it’s easy to see if she’s goofing off or not getting things done. But when you hire a remote worker, you don’t have any of those visual clues.

Even so, Ryan knew things weren’t getting done. “I had rationalized it away and said, ‘Well, maybe I don’t understand exactly what’s happening or maybe they’re doing preparatory work,’” he says.

These days, Ryan’s pretty much got this remote team managing thing down. And hiring folks that live anywhere has also helped Ryan scale up his team to 55 employees all over the US and UK.

In his Mixergy course, he shows you how to do it. Here are three highlights from the course.

1. Don’t Be a Scrooge

A freelancer drops off the face of the planet in the middle of your project. Now what?

They don’t get paid, sure.

But more importantly, you’re out the time and money invested in this person. You’re also behind schedule now.

So how do you persuade remote team members to stick around for the long haul?

Be Generous

Offer shocking benefits that inspire loyalty.

“I think that people who are stingy just don’t understand how people work,” says Ryan. “No one is going to give you their heart and soul if they feel that you are an Ebenezer Scrooge…”

So what kind of shocking benefits does Ryan offer? Health benefits, retirement contributions, a 4-day workweek, paid sabbaticals, and a lunch stipend, just for starters.

“All this, in addition to taxes, comes up to about 30% of one’s salary,” he says. “But if you plan for that and you put that in your cash flow, then it’s all doable.”

2. Show Them the Yellow Brick Road

Working remotely has its advantages: never being in rush-hour traffic, no pointless meetings, the freedom to work in your sweatpants…

But it has its disadvantages, too.

For one thing, there’s less face-time, which makes it harder to keep your team engaged. There aren’t as many opportunities for remote team members to discuss goals, progress, and problems.

Also, when a team doesn’t meet in an office, it’s difficult to see the role each person plays in the company. That makes it harder to rise up and take on more responsibility.

So how do you engage a remote team member and help them grow?

Set Them on a Career Path

Show team members their career path at your company.

“People want transparency,” says Ryan. “They need to understand where their career could go.”

At Treehouse, every job has a salary range. Each quarter there’s a set salary increase a team member could get. “The idea is that there is a feeling of progression, that you know you could get to this salary up here,” he says.

This system gives every team member goals and rewards to work toward.

3. Don’t Try to Be Steve Jobs

Despite the most rigorous hiring process, sometimes you’ll still hire the wrong person. Then you have the unpleasant task of firing them.

Ryan used to procrastinate firing underperformers because conflict was so painful. “Back in my late 20s, I just wasn’t as assertive and direct,” he says.

But waiting only resulted in missed deadlines and lost revenue.

So how do you get over your fear of firing?

Your Job Is Not to Be Easy on People

It’s always hard to fire someone. But procrastinating doesn’t make it easier.

“I look at someone like Steve Jobs,” says Ryan, “and sometimes I think I wish I could be a little more like him. A little rougher, a little bit meaner, and just say things that upset people. But I’m not that person. That’s not my personality, so I just have to fight the fear of upsetting people.”

How does he fight that fear?

“Now I realize [waiting] does no good to anybody,” says Ryan. “People generally know if they’re underperforming. If they don’t know, then you should tell them, because in the end, if you’re the business owner, or the large shareholder, it’s your job. You have to say the truth.”
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Written by April Dykman

  • Ryan Hart

    I completely agree with the generosity/loyalty aspect. It is important to communicate that the relationship is the goal, not the money. Show people you value them and be genuine about it. There are a handful of people who have treated me like this and they have earned my unquestionable loyalty.

  • Andrew Warner

    What’s a good way to do that?

  • Matt McCormick

    The one big advantage to treating your employees well, besides them staying on board, is they carry that treatment over to your customers. Treat your employees well and they will treat your customers well.

    Our company tries to give good employees a raise BEFORE they ask for it (or worse yet, quit). We have a number of employees that have seen a 20% increase in pay in under a year because they were doing a great job. What’s cool about that? They start working even harder and happier because they know they’re appreciated.

    We also don’t have any draconian vacation policies. We’re a brick-and-mortar store so we can’t just have people take off. But we simply ask our employees to make sure their shifts are covered and they can take a day, a week, a month off (and I often volunteer to cover them myself). They love that kind of flexibility.

  • David Nagy

    That’s a great question @AndrewWarner:disqus. Would love to know the answer too. @facebook-27210205:disqus ?

  • ThrowawayAccount

    I’ve been on the other side of this equation: a remote employee working for a startup. The CEO would never respond to my emails, and constantly reschedule our phone calls because “I need to respond these people on twitter.” At the time, we were bootstrapping the startup, so I was taking a financial hit and I had (stupidly) agreed to start working with the promise of equity (“we’ll just decide that later”).

    We missed our self-imposed deadlines, mostly because I never knew what I should be working on because of the lack of communication. I got blamed for those failures, and the CEO went running off to find investors telling them “We would be farther along, but I had problems with our technical person.”

    I can’t agree with this article enough. Be really nice to your employees, and they’ll bend over backwards for you. Stiffing them on pay, equity, and benefits doesn’t acknowledge their needs and worth… and, when a better offer comes along, you’re going to end up getting screwed. Further, if you are only paying me 50% of the other offers that I have, then I’m only going to work 50% as hard… And, who knows, maybe I’ll use that other 50% of my time to pursue a career that actually values me.

    I would add to the suggestions that you need to have regular communication with your remote employees, and you need to respect their time. Just because you’re paying them, doesn’t mean you can constantly push meeting times around for no reason. We may have a scheduled phone call or skype session at 10am, and I may have scheduled a doctor’s visit at 11am… so, if you push back our conversation by 20 minutes so you can respond to people on twitter, that means I’m going to either cut our conversation off or be late to my appointment

    I feel like, as is the case with most things in life, just don’t be an ass. Working remotely can be incredible productive and fun for all parties involved, just treat everybody with respect.

  • Stephen S

    It’s simple: actually care about them and their lives. Don’t treat them like a replaceable cog in your machine. If something’s wrong at home, send them a private email to let them know you’re there for them, or to ask if there’s anything you can do to help. Occasionally schedule meetings that aren’t about how they perform as your cog, but how their real (personal) life is going, and see if there’s anything you can do to help them personally – maybe they need help finding a school for their kids, and you know something about their school district, etc. I’m not talking about helping them move their couch or buying them things, I’m talking about being generous with your network, knowledge and time.

  • Andy

    I agree with what you are saying but dont feel picked on if you are a foreign cheap labor source. Jerks are jerks to their employees here (USA) too. They maybe even fired some when he/she hired you.

  • Andrew Warner

    This is one of the best uses of a throwaway account. Thank you.

  • Andrew Warner

    Yup. Jerks are everywhere.

  • Andrew Warner

    Good point.

  • Andrew Warner

    This is helpful. Thanks.

  • Caleb Page

    I have two companies I manage remotely. I find there’s a careful balance between motivating remote managers to take on the correct behaviors and being patient while they learn their way. Still, I’d like to have a little more Steve Jobs in me. I was with a bunch of multiple business owners last week and one quote shared that jumped out at me was, “You get what you tolerate.”

    I just completed the first phase of an early stage company where the CEO and Founder couldn’t have been nicer with staff. He was weighted on the Yellow Brick Road side of things because he didn’t have much to share. This relationship was solid enough that I was willing to invest a year in it with him getting things off of the ground. It may have been foolish in hindsight, but good manners went a long ways!

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    I love this. Andrew thanks for paying attention ALL aspects of startups instead of just the “sexy” ones… This is the stuff that eats up the time and energy of entrepreneurs and can really take people by surprise.

    The most beneficial item that I do on a day to day basis to manage my team is blueprinting through screencast or screenshots. This leaves no room for excuses. If you make absolutely sure that they understand the project at hand and get their buy in then there shouldn’t be nearly as much waste. This takes time but is worth it in terms of faster turn around time on the project itself.

    The other thing is to make it extremely clear that you expect them to ask questions if there is any uncertainly whatsoever. Again, if you make sure they know that you are available at all times for questions (and that there are no dumb questions) then it lessens the likelihood of them spending time and your money going the wrong direction.

  • Andrew Warner

    That’s been huge for me.

  • Eina Carpeso

    It really is hard to trust someone who can be found half way around the world and whom you haven’t even met personally. That’s why I think it’s much better to have a full time remote team working for you. With this, your professional relationship can develop as well as your trust with each other. And I have to agree with you that you need to be direct. It doesn’t come off as rough, it just means you’re a great leader and you know what you want from your employee. It will serve as their motivation.
    These tips are a lot of help. If I could share, there’s also an article I’ve recently bumped into that I think will give you additional techniques on working with a remote team.

  • Jennifer

    Nice tips! I particularly like the one about keeping employees by being generous, that shows they are appreciated!

  • Andrew Warner


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  • Kamile Ko

    These tips are useful, but I do not believe that it is enough to implement them in case you want to be a succesful business person. What helped for me to become succesful? Is implementing these suggestions- s?kmingas

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  • Ved Raj

    I run a remote development company named ValueCoders. I found that our clients lag somewhere in getting the attention. Getting your tasks done is not the ultimate thing to achieve but smooth flow of work is what is required. For that proper appraisals, allowing employees to freely work and motivating them is much important.