I’ve been helping other people get started with their own experiments in delegation, and one of them asked me how I manage my team in oDesk. Here’s how I do it.

Setting expectations

I like thinking of oDesk contracts as mini-experiments. It’s not about hiring amazing people – as in the regular job market, amazing people usually have their plates full of work and don’t have to look for more (aside from word of mouth). Each hire is an experiment involving the process and the person. If it works out, wonderful; I’ll keep them on as long as I can find work for them to do. If it doesn’t – and there have been some gigs that were just not a good fit – well, it’s only a small experiment.

I like taking notes so that I can hire people again for other things. Many people move on from oDesk after some time, though, so I haven’t always been able to go back and rehire people who have worked out. I try to focus on developing good processes instead of relying only on hiring good people, though, so I don’t mind turnover so much. I sometimes have to refer to my notes to remember whom to send tasks to, though!

Someday I might graduate to having one or two assistants with more time dedicated to my tasks. In the meantime, this patchwork of assistants requires a little bit more oversight.

Posting a job ad

I usually post my job ads for as-needed work, 1-3 months, < 10 hours a week. This gives me the flexibility to experiment on a low-commitment basis.

In addition to describing my requirements, I also ask that job applications show their attention to detail by beginning and ending their cover letter with an unusual keyword, such as “blue”. This makes it super-easy to filter out people who are indiscriminately applying to job posts or who don’t read the requirements all the way through. Many people put in the first keyword, and a few remember to put in the last keyword as well.

I often ask people to include a sample of their relevant work in their cover letter, and to describe their experience (especially for skills that are optional but useful). I detest the scammy practice of asking people to do unpaid work as part of their application, so I only ask for existing work samples.

Stephan Spencer (one of my delegation role models) uses a riddle in his job application / interview process as a way of testing people’s thinking. He spins one of the classic riddles into something that’s not easily Googleable, so he can see if people can figure things out on their own.

Here are some job posts I’ve used:

• Transcription of MP3s/videos
• Virtual assistant needed for appointment setting, following up after events, managing social media, etc.

Filtering people

As mentioned, I use attention to detail as one of my quick filters for applications.

I usually also search and filter by 4.0+ rating, > 100 hours on oDesk, but I’ll look at the reviews even for people with lower rating if I like their profile. I’ll occasionally take a chance on people who are new to oDesk – everyone’s got to start somewhere – with the expectation that I’ll need to teach them a little more about working with me or using oDesk to file time.

It’s always a treat to find good people in the Philippines because I’m from there as well, so the shared cultural background makes interviewing and working a little bit easier.

Inviting specific people

When I come across interesting people’s profiles, I save their profile in oDesk or Evernote (Evernote is easier to browse/search). After I post the job, I invite them to participate. There are so many good people looking for work, though, so I don’t often do this.

I occasionally create private job posts and invite specific people to them. I more often post public job posts even though I invite specific people to them, because you never know what kind of awesome talent is out there.

Interviewing applicants

I want to confirm that people understand the job requirements, find out how much they meet the requirements, and – also important – learn more about their other skills and their career goals so that I can come up with more tasks that fit them.

I use ScheduleOnce to schedule Skype interviews. The timezone difference and the interface turn out to be useful filters for attention to detail and willingness to deal with unknown tools. For virtual assistant positions, communication skills and trust are key, so I like talking to people first.

I also want to answer any questions they have. Contractors take on some risk whenever they accept a contract, as there have been quite a few employers who have scammed them into unpaid work or feedback blackmail. I want to give them the opportunity to make sure I’m not crazy, too. =)

I’m working on improving my interview process. In particular, I’m going to start asking people to tell me a story about the time they were wrong about something or the time that they argued with someone. Talking to my mom about her HR issues (and now, sorting through my own!), I’m beginning to realize the importance of understanding people’s conflict/disagreement resolution strategy and whether they can maintain calm and respect under stress.

For straightforward tasks like transcription, I might hire someone without ever talking to them in real-time, because I can “interview” them in the process of them working on their first paid task.

Hiring and onboarding

After we answer each other’s questions satisfactorily, I go ahead and set up the contract. For virtual assistants who will be communicating with other people on my behalf, I’ll set up a Google Apps account. LastPass makes it easy to share and revoke passwords, and I’ve also started the habit of keeping track of who has access to which accounts in order to simplify offboarding them when I end the contract and onboarding a replacement.

I usually keep the job post open until the person has satisfactorily completed their first task and we’re happy with the time/process. That way, if I need to hire someone else, I can choose from the pool of applicants that I’ve already shortlisted. Depending on whether I have tasks that can be broken down and done in parallel (ex: data entry), I might hire several people with the understanding that I’ll choose one or two going forward.

Coordinating

I send most tasks by e-mail because that’s the most convenient for me. I use Skype or Google Hangout to explain tasks in more detail. Since Skype tends to perform badly when I’m out and about, I also give assistants my cellphone number. I’ve been trying to get people set up using my VOIP phone so that they can call me, but we haven’t sorted that out yet. The easiest way might be for me to fund a company Skype account and have them call me with that.

I don’t want to require people to shift their timezone / sleeping habits – some of my friends have done overnight shiftwork before, and it really messes up one’s social life. Since my virtual assistants have access to my calendar, they can either use that to directly book me or use ScheduleOnce to find a time that works with their schedule.

I try to remember to specify due date and time budget (ex: spend a maximum of 2 hours on this, then send me whatever you have so that we can make sure you’re on the right track). The due date typically works, although I don’t think anyone’s been paying attention to the time specifications yet. I might revisit the Four Hour Work-week’s templates for getting these things communicated.

I hate the idea of tasks falling through the cracks especially if assistants get preoccupied with other things, so I’ve been experimenting with project-management applications like Trello or Asana. I want to be able to see what tasks I’ve assigned to people, what’s waiting for a response, and what’s done. One of my assistants just updated her Trello board – hooray! I gave her a bonus to recognize her initiative. =) We’ll give that maybe six months of trying before I even think of introducing a different tool. We’ll see how this goes!

Rewards and recognition

In addition to the automatic billing that oDesk takes care of, I like catching people doing something good and giving them an unexpected bonus. I always explain why I give the bonus. For example, I’m impressed when people take the initiative and when they submit excellent and timely work, especially if this is my first time working with them.

People don’t often negotiate with me for a raise, probably because my contracts tend to be shorter-term. As a client, though, I like being different by proactively giving people raises – I occasionally check my contractors’ profiles to see if they’ve raised their rates, and I’ll raise them during our existing contract because it’s good to reward good people.

I also take notes on people’s career goals and personal interests, and I try to tailor the tasks to fit them.

Dealing with miscommunication and disputes

As the employer, the buck stops with me. If someone didn’t complete something to my satisfaction, it might be because I didn’t sufficiently communicate the requirements, didn’t invest enough time in oversight or training, didn’t filter enough for skills/fit, and so on. Each mistake is a learning opportunity.

Typical mistakes and how I’m learning to deal with them:

I didn’t specify the level of detail I wanted, so I get back a War and Peace epic equivalent when I wanted Hemingway-short summaries.

• Share the big picture (Why do I want this? What will I use it for?).
• Provide sample output.
• Give a time budget, so that people get back to me after 2-4 hours instead of spending two days on a task. (Still working on getting people to follow this…)

People promise to work on something, but end up not doing it. It happens; people can be over-optimistic about their time.

• Set earlier deadlines than I need, and give myself leeway to try someone else or do it myself.
• Follow up. Then follow up again. If necessary, take the task back.

I get the output back and think I should probably have done it myself instead (skills, background knowledge, whatever).

• Breathe.
• See the value in a first draft and alternative perspectives. Focus on the good.
• Remember the additional benefits of this delegation experiment – it’s not just about saving time, it’s also about learning how to give instructions and work with other people.

I find that some steps are missing.

• Consider whether the steps are truly necessary.
• Review the process and flesh out the steps. Explain why the steps matter.
• Turn the process into a checklist. Add the checklist to my e-mail templates if needed.
• Keep a closer eye on tasks, at least until the process is sorted out

An assistant is uncommunicative / unreachable.

• I take back any tasks needed.
• I follow up to see what’s going on. Life happens, and people sometimes need support and understanding to get through rough spots.
• If they’ve become too busy to work on my tasks or they’ve gone AWOL, I shrug that off as a cost of doing business, and pick up the threads from there.

For chronic mistakes: If I get along with the person, I might give them different kinds of tasks instead. I might end the contract, but be open to hiring them again in the future. If I feel really uncomfortable, I end the contract and resolve not to hire them again, which has happened in a couple of cases. That’s also a good prompt to go back and think about how I can improve my hiring and training processes.

Ways to improve

I sometimes get distracted by other things I’m working on, so I end up not sitting down and investing in delegating tasks. I’ve attempted to address that by giving people 10-25% discretionary time for learning things and brainstorming other ways they can help me, but assistants seem to be reluctant to take this self-directed time, so I may need to tweak how I communicate it. Maybe I should turn it into a formal task, or establish a weekly wask – “I want to give you at least 5 hours of work each week, and if I don’t, please use one hour to brainstorm ways you can help me and send me a note.” Hmm…

Another tip from one of my role models was to involve assistants in your weekly review so that they can help you with your big picture. One of my assistants has a long-term career interest in HR, so I’ve just invited her to set up a weekly one-hour meeting with me where we can review what I’m working on and what I’m planning to do next. Maybe she can help me brainstorm what and how to delegate. I think that would be great, and possibly more useful than the discretionary time idea (at least for starters, until people get a better sense of the big picture and trust that I won’t blow up at them for learning something.)

What else would you like to know about how I delegate? Do you have any tips that can help me do this better?