Tales from the trenches: Shane & Peter


The dot-com bust proved a bumpy ride for Shane Pearlman. After working at five companies in two years, he decided that he’d actually have more security as a freelancer. Eventually, he joined with a frequent collaborator, and software consultancy Shane & Peter was born.

Now the company exists as a sort of freelancers’ co-op, working with an ever-evolving cast of entirely dispersed tech pros (about 30 at the current count) to build cool things for top clients. How does Pearlman stay on top of such a loosely knit collection of talent? WebWorkerDaily spoke with him to find out.


Pearlman talks about talent in a vocabulary that wouldn’t be foreign to a relationship coach, and it’s obvious he makes finding and keeping the right people about personal fit as much as tech skill (though that’s important too).

“I probably spend as much time hanging out online with my team as I do my wife, and I picked my wife really, really carefully,” he says. “I should probably pick my team just as carefully, in terms of people who actually make me happy, who have similar visions of the world and their goals.”

Shane & Peter use video interviews over Skype and short, paid test projects to screen talent. To evaluate candidates’ performances, Pearlman uses a simple rubric cribbed from a long-ago Wells Fargo survey. “They said, ‘Are you delighted, satisfied or dissatisfied?’ I knew exactly what those meant. There was no, ‘Gee, I wonder, Am I a 3 or a 4?’ We rate everyone that way.” If someone delights, they get more gigs; but delight is down to work style as much as the finished project.

“I can’t ever walk over and check somebody. I can’t sit on them. More importantly though, I don’t want to,” says Pearlman. “I want to work with people who are competent and can communicate. I built my own business because I happen to want a life, so I need to work with people who allow me to have a life, and that means they can self-manage to a certain degree.”

Pearlman values independence in talent, but also in management, returning again to a relationship metaphor to explain. “Don’t be the jealous girlfriend,” he advises managers. “Freelancers are freelancing because they want to be able to control their lifestyle. Being a good manager means understanding that and being able to work within that context, being able to set goals and deadlines but not micromanaging.”

There is one downside to this focus on hiring for cultural fit, Pearlman admits. His team is too similar in background, a problem which Shane & Peter is currently working to fix.


As a software consultancy, Shane & Peter has the ability to tweak and even build the tools it needs for collaboration, and they’re currently contributing heavily to their core tool, an open-source project management system called Chili. This isn’t an ability every remote team will share, but Shane & Peter’s innovations do speak to the types of issues that afflict dispersed teams and the kinds of solutions that can make an impact. Pearlman gives two examples:

“We realized last year we lost about $70,000 when people were back clocking time after we’d invoiced the customer. So we built a little tool we call the Clockblocker. And all it does is, it doesn’t allow you to clock time further back than three days. No big deal. Tiny little change, but drastic financial impact.”

Similar ingenuity was applied to accountability issues. “You’d have somebody working on something and then they’d ask somebody else a question and then they’d move on. But you need to keep accountability despite that you asked a question. So we built a little addition. It allows you to assign a comment to a person and it will keep bugging that person until he formally answers that question. It keeps the original task assigned to the right person but it gives them a way to share accountability just a little.” Clever.


If you’re going to hire independent contractors, make sure you’re not their only client . . . not by a long shot.  The most obvious reason for this is legal, notes Pearlman, who says he is a little paranoid about the IRS reclassifying one of his contractors as an employee and stinging him with a massive bill for back taxes.

But there are other reasons to make sure your contractors have a flourishing and diverse client base. And happily, doing so benefits both management and contractor. Pearlman aims “to make sure that our freelancers build the business they need to be sustainable. I don’t want to put in a bunch of time helping somebody only to have them come to me six months later to say they’re going to go become an employee somewhere because they couldn’t actually freelance successfully. I want them to have a lot of customers. I want them to stay in business.”

Finally, Perlman closes with a tip to get your team to set its own milestones. Work collaboratively to set deadlines and you won’t have to say things like, “I told you it had to be done on the 10th.” Instead, it’s much more effective to be able to say, “You told me you’d have this on the 10th.”

Image courtesy Flickr user VanDammeMaarten.be


Tracy Dawes

The comment, “I picked my wife really, really, carefully,” made me smile. I wonder if that’s how my husband landed me. I wonder what logistics go into this careful planning. Would be curious to meet the wife.

Peter Chester

Thanks for the great write up Jessica! I love Shane’s quote “I picked my wife really, really carefully”…. Funny.

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