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How I manage 40 people remotely (ryancarson.com)
262 points by ryancarson 1074 days ago | 57 comments



You don't manage 40 people, even on site.

However my manager gets along managing me and 5 other employees, all remote, no problem. We have a weekly group call and an individual call every one or two weeks, and we supply a monthly email giving brief details what we did over the month (no more than 20 or 30 lines). The rest of the time we chat on IRC and by email as necessary. We meet together once or twice a year, usually combining that trip with some other event such as a conference to reduce the number of extra airfares.

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This sounds like a dream job.

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Feeling lonely yet ?

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Do you only have friends at work?

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I work at a company of twelve (Fictive Kin, whom you might remember from Gimme Bar and LeakedIn that were on the front page last week), and every single employee is a remote employee. We have people on the US East coast, Canadian East coast, US West Coast, Central USA, the UK and Denmark. So when you factor in time zones, varying civic/religious holidays and the fact that many of us attend and/or speak at conferences around the world, you'd think that team "management" would be a nightmare.

As it turns out, it's not that bad at all.

Having everyone working remote is actually a blessing - it means that all of our processes are optimized for an asynchronous workflow. We use a private IRC server for all internal communications, email for conversations that need to be a bit less ephemeral, a tracker for our various projects (Pivotal, in this case) that need attention, Dropbox for file transfers and wireframes/mockups, Google Docs for spreadsheet-y things, Google Hangouts and Skype for video/audio communication, and our organization Github timeline for all things code-related.

Additionally, we try to keep the management overhead to a minimum: Weekly company calls on Fridays where we discuss internal dev/design things that happened over the week and what movies we saw or what level our Diablo characters are at, and then project-specific calls as needed during the week. All but the all-hands call on Fridays are optional; if you don't have anything to say, then you just don't join the call. We also try to get together for a more face-to-face gathering once a quarter, and try to pick a fun and convenient city in the world to meet in.

It's not black magic. It just takes good people and some minimal async-focused processes for it to work. Hire bad people, stuff goes bad. Implement too many synchronous (read: obligatory meetings, calls, timesheets, status reports, etc.), and stuff goes bad.

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I manage 85 people (~15% of our global IT organization) in 9 countries and 14 times zones, but size doesn't matter. The ability to build a trust relationship, hire & develop talent successfully, and delegate well are what matter most. Face-to-face meetings are still valuable, but choosing the right tools for videoconferencing (Skype, Gtalk Google+ Hangouts, etc), screen-sharing (Hangouts, Screenleap), collaboration (Google Apps), and Project/code management (SVN, JIRA, Confluence, Google Docs, Balsamiq) are more important.

Pro-tip: focus on hiring the right person for the right role, not just the best-person-you-can-find-but-you-don't-have-a-good-fit-spot-for-them, and outsource things that are not core competencies (perhaps SEO & marketing, perhaps UI/UX, perhaps even mobile dev). Use common sense and treat people respectfully. Make providing an enriching workplace and a good work/life balance part of your mission statement.

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I was nodding my head in agreement until you suggested outsourcing your UI/UX. That's basically outsourcing your core product (presuming your product is delivered via screen).

I'd never do that.

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We don't know what business the GP is in. If somebody is in an IT department that supports the core business, rather than is the core business, doing things like reporting applications, internal enterprise apps, etc... is the UX still the core product?

If you're making a maintenance team scheduling app for an oilfield service company, and you outsource the UX and save hiring on a team of Javascript/HTML5 devs that would have little work afterward, isn't that rational?

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I'm in an IT department that primarily supports the core business. The UX is an afterthought in a tight margin industry and we generally settle for "it works and isn't too confusing". I'm not happy about that, but it is what it is. <banghead>

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Good summary of tools, but would love to hear more about the process challenges. Tools are obviously just a small part of the challenge.

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Good idea - I'll try to blog about that soon.

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Cool, thanks Ryan. I currently work remotely for a small company and lead a 4-person team. We use some of the tools that you mention and a handful of others to accomplish essentially the same thing. I think figuring out the tools is a big deal for a lot of companies going fully or partially remote, but after those are figured out, there still seems to be a very different management/process angle that I haven't seen addressed much. Definitely enjoyed reading about the tools, as well, though.

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I wonder how much interest there is in a "usesthis" series for SW tools + processes companies & individuals use rather than just the more hardware-centric stuff on http://usesthis.com/.

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Do it! You can fork my site right now, if that'd help:

https://github.com/waferbaby/usesthis/

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Rockin', dude. If I take you up on this I will absolutely let you know. :)

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There is a site out there that does this but I will be damned it I can remember the name of it. They interview companies like github etc and talk about the technology stacks and how they do things at the companies etc.

As well as the video interview there is a summary of the points listed for easy reading / linking.

The site is on a .tv domain and I am pretty sure it began with an m. When / if I find it i will edit / reply to this comment. In the meantime if anyone can remind me what the name is...

EDIT: Found it, http://webpulp.tv/

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And if you sell it on to Facebook for $1B, definitely let us all know. :-)

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Interesting article with some ideas I'll try to push at my company, but I think the title is a bit misleading and could potentially cause people who follow much of what is good advice to end up with big problems.

My problem is with the word "I manage 40 people remotely". Almost no one can manage 40 people themselves, probably no one can do it well. It sounds instead that you "run a company of 40 people remotely through managing seven people remotely". I got seven from the department heads meeting you described.)

Of those seven people you directly manage, how many of them are in the same location of their direct reports? It sounds like you have an office manager in Orlando who manages a good sized group of people. What percentage of your employee's work in that office. Because if its a high percentage, then a large part of your true solution on how to manage 40 people remotely is to hire someone who manages them locally.

That's the way I think it could be read and that distracts greatly from the other interesting tools and processes you discussed.

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Only two of the Managers lead teams that are in their same physical location.

Our VP Sales and Chief Product Officer manage all remote people.

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Ryan: I'd love to hear specifics about the problems you're encountering with being remote at this size?

I have a remote team and we're growing but I would like to stay that way for as long as we can so I'm interested in hearing about some of the specific issues.

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Great suggestion. I'll add it to my list of blog post ideas. Thanks!

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"My goal is to slowly gather Team Members in our Portland office but leave our Video Production and Teaching in Orlando (it’s affordable there and the office is established, so no need to move it). Alan, my Chief Product Officer, is moving his family to Portland as well so we can work together daily."

So is the eventual goal to just have several different offices but no remote workers?

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No, we'll always have remote Team Members. It allows us to hire the best people in the country.

We'll just have a concentration in Portland and Orlando.

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> Portland and Orlando

Completely off topic, but I always do a bit of a double take when I realize that from Florida, Portland is a lot farther away than, say Bogotá or Caracas. I guess you get used to looking at US maps without any context as a kid.

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Yes, but those 40 feet through US customs all too often turns out to be a long trip indeed.

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It allows us to hire the best people in the country.

World, no?

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Yes, technically. But we're still trying to keep our general group of Employees US-based to make the quarterly meetups and online meetings more achievable.

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Thanks for sharing!

I'm just about to start a full-remote schedule at the job I've had for 7 years. I'm extremely nervous about my future with the company. I work for a big, older tech company where remote working is an afterthought, not ingrained in the culture like Treehouse.

We're moving from Massachusetts to Tampa, FL to pursue a job opportunity for my wife (She's an attorney). I am extremely lucky to have been approved by the corporate chain to continue my responsibilities remotely.

Who knows, if it doesn't work out with them, maybe a job at Treehouse is in my future!

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I wrote about working remotely a bit more from the employees perspective @ http://arandomurl.com/2011/09/03/working-remotely.html

Since I wrote that post I joined Mozilla as the only employee out of Scotland and I feel like I need to write the post again, Mozilla are superb at dealing with remote employees which I am sure comes from the foundations as an open source project.

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Never heard of Trinet before but it's definitely a tool to consider.

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Most outsourced HR has a lower bound for number of employees. I've seen them as low as 4 but they really don't like that and don't make any money. You should switch to one as soon as you can. It's a silly amount of paperwork for each employee, but all of the administrative stuff they do (including getting you healthcare plans) isn't something you should be doing in house.

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Even if you don't care about getting to outsource the administrative overhead, the healthcare alone may be worth it. Since they're negotiating as a very large company, they can offer significantly better plans than you would be able to by negotiating with providers as a small startup.

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This is why I want a national healthcare service. Let's all form one giant company, one big single pool, for health insurance purposes.

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I'm assuming you're in the US, and this is not at all what the ACA does (which is the closest approximation to a US version of NHS).

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Is it covered internationally or just US?

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First-hand experience here: Trinet is the worst of the worst, managing to slim down the HR experience to the absolute bare shittiest minimum. It's degrading to talk to their reps. A disaster.

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@ryan - great tool suggestions!

This process has been on the forefront of my mind quite a bit lately, as I am growing my company, Canyon Oak Partners (SEO/PPC/Design/Dev) and a supporting SEO Audit software offering (its in private beta).

At this point, the most important facet I wish to grow is the sales team. My partners and I are discussing the need and pros/cons of getting an office, as we all work remote right now. We also gather at my home (I have a spare bedroom as my office and we set up around the rest of the place) a couple days a week.

Our thoughts lean toward the social energy an office brings, but I love not spending the money on an office.

Do you have any advice on managing a remote sales team?

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My VP Sales manages his Team, which is now up to four people. I don't directly manage the Sales Team.

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Ryan, I noticed from past posts of yours that you are probably a very family oriented guy. Just wanted to get your perspective on moving you and your family half way across the globe. I myself am considering moving a good distance from my family (parents and siblings, I'm not married yet) and I wanted to get your advice on big moves.

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This is the guy Arthur Clarke has been talking about fourty years ago. https://www.youtube.com/watch?v=OIRZebE8O84

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Great article! I guess this all start with good hiring. If the people you are good, then this works great. If you skimp on this: you are in trouble.

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We've built a tool called TeamSnippets.com to help keep teams in sync - I believe it works extra well for remote teams.

On an interval you like, we send out an email to each team member reminding them to write a status update of what they've been working on. Everyone's status updates are gathered into a summary email sent out the next day.

We're in our free beta right now and would love some feedback. Give us a try at http://TeamSnippets.com

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The problem I have with this sort of thing is it duplicates what is already out there. Between my Github activity and Trello anyone can tell exactly what I have been doing, and what I'll be doing next.

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Every team is different and in the teams that I have worked in, Git commits and Task Trackers don't usually contain the same type of information I present in a standup.

Git commits are way too technical for non-engineers and task trackers either have too much information (i.e debate on how to do X and Y) or too little information (i.e just a simple task title).

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I don't know why outsourcing HR seems like a good idea for anyone. 40 employees, 100 bucks for each every month, that's the salary of an HR manager.

Don't do it yourself if it is not your focus, but don't outsource it. You need someone in-house who can not only manage the administrative paper works but also give you advices about what's best for your own company.

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The median salary for an HR Manager is $78,000 according to glass door .http://www.glassdoor.com/Salaries/hr-manager-salary-SRCH_KO0...

You're looking at 65 employees at $100 a month to make that pay off.

For most companies between 4 and 65 people, outsourcing HR is a big headache reducer. Having worked at companies with outsourced HR, I can tell you it's not amazing, and it could be way better. But HR is a cost of doing business, and not something you should be trying to do yourself as a young business.

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Don't forget that the cost of an employee isn't just their salary. Insurance, health, and other benefits all add up (I think I read somewhere up to 30% more), not to mention that you now have another person to manage.

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A funny thing too: having an HR manager tends to automatically increase this cost. ;-)

NOTE: Not a strike against HR, just reflecting a reality that salary figures for HR people probably disproportionately understate their overall cost. HR people are much more unlikely to work at a company where the only compensation is salary.

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The actual cost of that HR manager to the company would be much greater than their salary if you consider all the overhead. Even if you manage to find someone for dirt-cheap, you'll still need an internal system for managing everything, which won't be free.

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You should add 30% to any salary to account for benefits.

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Would an HR manager be better? You can host your own email servers for less than Google Apps for Business, but it's not something I would recommend.

Update: even if you do hire some flesh and blood to sit behind an HR title, they are still most likely going to outsource things like payroll. Companies like Paychex are huge because they make sense and save a lot of money.

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Agreed. Keep in mind the liability aspects as well. From what I understand, payroll mistakes are not easily forgiven. That is part of the reason there are so many HR outsourcing companies.

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One of the benefits of an outfit like Trinet is that since they manage so many employees they get good prices on benefits. Trinet has all kinds of discounts they offer employees on buying computers and lots of other stuff. It's basically taking advantage of economies of scale for HR.

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Just curious, why Portland?

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I see a lot of folks fleeing the Bay Area to go to Portland.

Compared to SF, the cost of living is far more reasonable for experienced folks that have or want to start a family.

The area is attractive with a lot of natural beauty, mild weather, and lots to do.

SF is only a short plane ride away to meet with VCs and angels, and you're still in the same time zone as them.

The business climate seems better and the government is pretty amiable for new businesses.

The one thing it still lacks is diversity. Seattle and SF are still far better in this regard.

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What type of diversity are you referring to? Is this really something that factors into a decision about where to live?

I would think saying "I want to live somewhere where everybody is different than me" is almost as bad as saying "I want to live somewhere where everybody is the same as me"

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I was told the remote team can be managed remotely should not exceed 6 employees, more than that you need a team leader or a local manager.

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