I'm interested in videocasting/podcasting as a richer and more interactive way to get stuff out of people's heads and into other people's heads. I've come to terms with the fact that most people don't write anywhere near as much as I do, but that they know all sorts of things that they might not have realized yet. Talking to people seems to be a good way to help them share that, because many people find it easier to answer questions than to share on their own. Likewise, podcasts recorded live make it easier for me to bring in other people's questions (bonus: I learn more in the process!). So, podcasting, even though actually talking to people is hard. Maybe if I do enough of it, I'll get desensitized to the anxiety and I'll get better.

Along those lines, I've been doing a weekly show for Google Helpouts providers. It's a community of maybe a thousand people, which is a tiny niche in the Internet. I used to have co-hosts, but they're on hiatus for various personal/business reasons. I did my first solo show the other week, and my second was last week. So far, I have managed to survive. I like it because Google Helpouts is a new platform and everyone's still figuring things out. I'm fine with talking tech and maybe a little online marketing/customer service, but other people know so much more than I do about business and education, so interviews are a natural fit. I'm getting settled into a decent workflow involving Hangouts on Air, the Q&A module, MP3s, and even drawing sketchnotes while the conversation progresses.

Sketchnoting is oddly calming. I had done it from the very first show, when I had a co-host handle all the niceties of reaching out to people, introducing them on air, and asking questions. For a kick, I tried seeing if I could do it even when hosting solo, and it worked out fine. You'd think adding one more thing to do during the show would drive me crazy from multi-tasking, but actually, drawing keeps me not-stressed-out enough to listen well, ask follow-up questions (since I have my notes handy!), and help people follow along with the conversation or catch up afterwards. Besides, it's a good excuse to swap out my webcam image for the screenshare, so I don't have to be “on” all the time.

So the interview itself is fine, and it will get better as I pick up more experience.

Then there's all the rest of the processes around that. I typically stay up about two hours after the end of the show. I chat with participants off-air for 30-45 minutes (this is usually the most fun segment!) and then handle all the post-work, since I like it when the resources are posted right away. That way, I don't have to go back and work on it again. Although it's certainly possible to just let the video be automatically posted on my YouTube channel and be done with it, I like putting together the video, my visual notes, an MP3 download (for the people who prefer to listen to the podcast while, say, doing chores or walking around), and eventually a transcript. If I'm going to do something, I might as well use it as an opportunity to explore what awesomeness look like. =)

That said, wouldn't it be awesome to be able to document my processes so that I can do them without worrying about missing a step, and so that other people could take care of making things happen? I'd love to worry less about identifying, inviting, and coordinating potential guests, too. Someday.

Since many of the things I do involve my Google account, this probably means building trust carefully. I was thinking about what sequence of activities might make sense in terms of trust.

Come to think of it, I can improve my post-podcast process by parallelizing some of the tasks that take a long time to do. Maybe I'll even figure out how to automate some of those tasks, like perhaps getting the ID3 information from a spreadsheet.

Here's a list that's roughly in order of trust:

When I started this 5-year experiment with semi-retirement, I fully intended it to be a learning experience in entrepreneurship. I wanted to learn how to create value. I wanted to learn how to sell, how to build systems. Mission accomplished. I have the confidence that if I need to work, I can help people and earn money in return. I can deal with the paperwork required by the government. I can negotiate and make deals.

The more I learn about freedom and space and creating my own things, though, the more I think that this should be my real experiment, not freelancing or entrepreneurship. It is not difficult to freelance. Millions of people do it. There's plenty of information about entrepreneurship too; no end to aspirational books encouraging people to break out of their cubicles and follow their dreams. But far fewer people have the space to simply create and share things for the sheer joy of it. Even the authors of those books on freedom work for their rewards.

It's an interesting experiment to try. I could focus on working on my own things, going forward. I've been winding up my commitments and avoiding new ones. I still have a little bit of consulting to wrap up eventually. I've been telling myself that the money I earn increases my safety net so that I can take those future risks. Besides, I like the people I work with. I like the feeling that I am helping them out and making a difference. (And there, taking a step back, I can see that the desire for a clear sense of accomplishment may be distracting me from more difficult self-directed work.)

Really, nothing can buy time. Probably even if I stopped consulting now — or if I had stopped a while back, or never started — I could still spend an appreciable amount of time making things happen. Postponing this doesn't make me live any longer. It doesn't mean that I have more core time, those hours when I'm alert and creative and happy.

I hadn't noticed for a long time because I had set too low standards for myself. I set trip-wires to trigger reflection: if I missed a commitment or started misplacing things, I knew I was overscheduled, and I cut back. The rest of the time, it was enough that family life was happy, blog posts were written, sketches shared. It was too easy to meet these conditions, so I didn't notice.

What would I work on? Visual guides to complex topics look like the most unique contribution I can make, and there have been quite a few updates for my blog (both technical and written) that I've been postponing for lack of attention.

Details help me visualize what that might actually mean:

I should treat myself as a client and as a contractor. If I were delegating this work to other people, would I be happy with vague specifications and without milestones? I wouldn't hire someone to maybe possibly think about something that could help people learn. I would spend the time to come up with a clear vision and the steps to make it happen, and then I would make regular progress that I would report on. The high-energy hours I have are best used for this long-term work; everything else can go into the non-core hours.

So I'll keep my existing consulting commitment to Tuesdays and Thursdays, plus whatever non-core time I can spare to help them get over this hump, and then we'll see if we'll continue or not. In the meantime, any consulting of mine will be with the commitment to replace all the hours I spend earning with at least the same amount of time in delegated work (plus whatever time I need to manage the delegation). The end result won't be as awesome as having the same amount of core time (and to be fair, my consulting involves non-core time too), but it should:

• build up a good library of procedures so that I can either delegate tasks to other people or work more consistently when I'm on my own (plus the benefits of process improvement and sharing)
• help me learn how to take advantage of other people's time — and better yet, how their skills and experiences differ from mine
• allow me to support people as they build up their own businesses and the local economy

In fact, just for kicks, I'm going to backdate the experiment–to replace my original 5-year experiment with it instead of starting just from this point onwards. Since I don't actually have a time machine, an easy way to make that commitment is to calculate all the time that I have spent earning so far. Fortunately, this is yet another question that time-tracking allows me to answer. The numbers in the sketches below are a little bit out of date now; the current ones are:

• 1874.4 hours spent earning since 2012-02-19
• 208.1 hours delegated through oDesk so far
• 55.1 hours spent managing the delegation (including documenting processes, interviewing, etc.)

So my ratio is about 1 hour of management to 4 hours of other people's work. A ratio of 1.3 hours should be enough to account for delegating the work, managing the delegation, delegating the time to cover my management, etc. That means that if I want to replace about 1874 hours, my goal is to delegate a total of 2437 hours. So far, I've delegated 208, so I have 2,229 to go. (Ignore the math in the sketch; this is the updated version.) That's a little more than a full-time employee. I'm not quite at the point of having streamlined, documented processes that can take full-time assistance over a year (or enough faith in my hiring abilities!), but I'll work up to it. (My first goal: delegate as much as I can of this podcasting process.)

It's a little scary delegating so much, especially since I'm normally quite careful about costs – but I think it will be worth it. In fact, I've been giving some virtual assistants raises to challenge them to think of themselves as people who can earn that. It's a little scary projecting the expenses, but if I commit to it and then focus on making the most of it, I'll gain more than I would if I kept waffling on the commitment. The work can start by replacing the routine, but it would be interesting to use it to support new projects someday.

As always, it helps to keep the end in mind.

I've been ramping up my delegation through oDesk, and I've also experimented with micro-task-outsourcing through Fiverr (with quite good results!). We'll see how it goes.

It would be great to share processes with other people. Timothy Kenny gave me a glimpse of his growing process library. I've posted a number of my processes at https://sachachua.com/business, but haven't updated it in a while. I'll share more as I hammer them out. I wonder what my end-state would look like. Maybe I'd just share this Google Drive folder, and people can copy from it into their own libraries.

Anyway, plenty of stuff to figure out. =)

I’ve been thinking about how I can reinvest profits back into this blog. My default is to save, save, save. There’s time to learn through trial and effort However, investing in help and tools has paid off before, and maybe I can get even better at making those decisions. Besides, if I’m going to scale back consulting and focus on other ways to create value, then it makes sense to invest in creating more advantages.

So I’m planning to find an assistant for this blog – someone who can work part-time on an as-needed basis, probably through Odesk.com. This is definitely not about hiring someone to “spin” keyword-stuffed content for me in order to boost SEO, nor do I need someone to keep me accountable when it comes to writing. I want more than that.

I want someone who can help me deliberately improve my blogging skills. I’ve been working on doing this on my own, and that’s going well. I’m getting the hang of outlining. The next thing I want to get better at is synthesizing information (making lists, describing alternatives, etc.) in a smooth, coherent, and non-plagiaristic way, bringing everything together with recommendations or a conclusion. After that, I want to learn how to:

1. Write better headlines
2. End strong: conclusion, call to action, question
3. Start strong: improve first paragraph, regularly set excerpts
4. Pick better post topics (research, feedback, etc.)
5. Send e-mail newsletters, perhaps gathering ideas and feedback for upcoming blog posts
6. Update, organize, and package information resources regularly

I also want to learn how to take advantage of feedback and coaching. Although I have many mentors, I don’t have a lot of coaching experiences. The last time I had a coach was for school programming competitions. Our coaches taught us algorithms and strategies. They selected problem sets for exercises so that we could see the concepts in action, and they also simulated contests so that we could learn how to work as a team. I learned a lot more than I did on my own.

PLANNING THE WORK

The ideal coach is someone who’s good at what I want to learn and good at teaching it. That way, they can model excellence—while explaining what they do and why they’re doing it. They can help me identify gaps in my understanding and give me feedback as I improve. They know when to push me beyond what I think I’m comfortable with.

This is what my ideal scenario for a blogging coach would look like:

1. We pick a skill to focus on, such as synthesizing information.
2. They recommend some of their favourite role models.
3. We come up with exercises or challenges (for example, I’m currently working on making sure I have at least one list a week, and that most new posts have images).
4. I outline the post, and they help me improve the logical organization.
5. I draft the post, and they help me improve it further.

Even if I can’t find someone who is clearly more awesome at the skill I want to learn, a different perspective can also be useful. Someone can help me check whether something makes sense, perhaps suggesting alternatives. Eventually, I want to learn how to put my editing hat on.

In addition to the coach role, there’s also value in the assistant role. It would be interesting to see what help with research and editing would be like. People use different keywords, so we might be able to find different resources. Maybe they can help me sift through and prioritize lots of results. The main question is that of relative advantage. I read pretty quickly and I get some value from reading the sources myself, so either they need to do that better than I do, or I need to shift the time I spend reading into something of even higher value.

An ideal scenario for writing assistance could be: I send them an outline and some notes. They send back summaries of the best resources with citations and links. I add personal stories. (This step comes after the research because I may want to apply the advice we find, and besides, that stops me from just looking for confirmatory evidence.) We draft, edit, proofread, and publish.

Besides, it would be nice to have someone turn transcripts into blog-ready content. (Or maybe I need to look around for another transcriber who gets blogging…)

I’m curious about the tools and processes that more experienced writers use, but those can be difficult to transfer. Maybe I’ll get lucky and find someone who does a lot of reflective practice.

In addition to getting better and working more effectively, I also want to prepare for situations when I might be more frazzled. It’ll happen. That’s just part of life. I could do what other people do and not blog, but it’s more fun to take notes and learn from the conversation. It makes sense to build that capability now, before I need it. When I’m stressed or sleep-deprived, someone else can check that I’m making sense and that I’m still following a good balance between “useful” and “personal”.

JUSTIFYING THE VALUE

I always try to talk myself out of expenses to make sure that I’ve considered my options. What are some alternatives to paying a coach/assistant?

I can learn on my own based on people’s voluntary feedback. Yay comments! I’m doing all right, and I plan to learn for a long, long time. There are plenty of great tips out there. I’m nowhere near the limit of what I can learn for free or from experience. Books and role models can give me passive, general guidance.

I can find or start a blogging mastermind group. Peer-learning may be slower, but I’ll benefit from different perspectives, stronger relationships, and shared goals. A facilitated mastermind group with a coach can be more cost-effective, and I can learn from the advice that other people get. I have good informal relationships with a number of other bloggers, although they aren’t connected with each other yet.

The alternatives are pretty good, so what advantages can working with a coach/assistant offer to make it worthwhile? Paying someone to help me learn can mean getting targeted, skilled, and consistent feedback. In addition, I can learn more about delegation and coaching, which will be useful for growing my other capabilities.

So it’s worth at least an experiment. What could that experiment look like? It probably looks like 2-3 hours of work once a week for at least a month, focusing on applying the skills to one post a week. That way, we can go deep instead of wide. We’ll use Google Docs or Draft to share work in progress, maybe with e-mail notifications so that we don’t have to check it all the time. E-mail and Google Hangouts can help us clarify or discuss things as needed.

The main risk is that I might forget to assign work, so I should prepare for that by structuring the first month up front and committing to a regular schedule.

At the end of the experiment, I’d like to be more comfortable synthesizing key points from my research and stitching them together in a smooth, coherent, non-plagiaristic way that adds value. Assuming that’s the skill we decide to focus on; we could focus on headlines, intros, or conclusions instead. I’m okay with working with different coaches for different things. It makes sense to play to people’s strengths, after all.

I’d like to be in the position of wanting to continue the experiment, and being able to justify continuing. I did a similar delegation experiment in 2009 (nearly six years ago!), hiring a number of different editors to give me feedback. At the time, I didn’t think it was worth repeating that experiment. (I’ve grown as a writer, but in different ways – outlining and illustrating have really helped!)

What will be different this time around? I think we’ll be less focused on wordsmithing and more focused on developing specific skills. I’d feel better about continuing if I get deep feedback instead of superficial feedback combined with reflective explanations of what’s going on. For example, reorganizing a post and explaining why that could make more sense is much better than making tiny word changes. (Unless they’re truly awesome tiny word changes!)

I may need to try a few experiments before I learn how to properly set up the instructions and the process, and I may need to work with different people to take advantage of different strengths. I should also experiment with signing up for a for-fee facilitated mastermind group, although maybe I should check if I have the commitment to get through online courses first. (I’ve been very bad at this in the past.) Lots of different things to try.

In terms of justification, it would be great if I can continue to treat it as a business expense. To keep the Canada Revenue Agency happy, I need to be able to demonstrate that it’s directly related to a business with an expectation of income. If I can point to how it will help me sell information products or courses (maybe on a pay-what-you-want basis so that I also feel good about making information widely available), then that will probably be enough for the CRA. If not, I just have to make room for it in my after-tax budget. It’s a trade-off between investing in increasing capabilities versus increasing my safety margin for being properly retired, but I think it will be worth it.

What’s in it for the assistant/coach? In addition to paying the agreed-on fees, I’m happy to share before/after comparisons and link to people in posts. Naturally, there’ll be plenty of process reflections and updates along the way. Teaching someone else how to improve their skills is a great way to improve your own, so that’s always nice.

Next steps: I’ve got one promising candidate, so now that I’ve fleshed out what I have in mind, I might reach out to her and start the interview process. And hey, if you happen to be a writer-type who’s interested, you can check out the job post – working with someone who reads my blog already would be even better. I’m open to hiring more than one person on an as-needed basis (experiments!), so go ahead!

Do you work with a coach or an editor? Can you share any tips for making the most of the relationship?

Image credit: Piggy bank (Oliver Hoffman, Shutterstock); Comic (CartoonResource, Shutterstock)

In Spousonomics (now retitled as It’s Not You, It’s the Dishes), I came across a brief explanation of David Ricardo’s theory of comparative advantage. Economically speaking, it can make sense to trade with other parties even if you can do something faster yourself, because trading frees you up to focus on higher-value work as long as the transportation and transaction costs are not prohibitive.

I’m slowly learning to let go of more and more tasks in terms of delegation and outsourcing. For example, I’ve been working with someone on developing marketing materials for this business idea around sketchnoting. We want to put together a leave-behind that can help event/conference organizers learn more. The person I’m working with has a lot of experience in graphic design and illustration, although I’m probably more comfortable with the copywriting and sketchnoting aspects of it.

She set this up as a fixed-price project. I’ve worked on similar illustration projects at fixed price, and I’m always careful to specify the number of rounds of revisions included. For revisions beyond that, I work at a specified rate, although I might throw in minor revisions for free. I do this because I know people in both software development and illustration who have gotten burned in an endless revision cycle because of client expectations, but I guess many illustrators do open-ended fixed-price projects instead.

When I hire people to do work for me, I want to make sure that I’m doing right by them as well. I don’t want people to get tired of working on this never-ending project. I want to build on people’s strengths and their career interests instead of running into their gaps. I want to focus on the highest-value activities, going for about 80% awesome instead of spending all the time trying to chase down 100%.

One of the things that I’m learning to do is to be explicit about what I value and what I’m looking for. For example, we were going back and forth on the copy for this leave-behind. It can take a while to get to copy that feels right. The discussion does help me clarify what style I’m looking for (now I have a “Goldilocks style guide” with examples of what’s too formal, what’s too informal, and where I want to be), but copywriting isn’t the key value I want to get out of this arrangement. I’d rather have her focus on the parts where I hope she can really make a difference.

I suggested using filler text like “Lorem ipsum” so that we can play with the layout and the feel of the piece without getting distracted by the words. It’s important to have an idea of the rough structure of the text – short paragraphs? a bulleted list? – but we don’t have to finalize it just yet, and I don’t want her to spend hours wrestling with it if there are better things she can do.

What are those things? Well, let’s think about what I really need help with in terms of a leave-behind. The final form factor is probably something like a half-sheet of cardstock. I want something that I can print at home if I’m in a rush, or have printed elsewhere for extra oomph. It should probably be double-sided for efficiency, but it has to accommodate the imprecise nature of printing on home-office equipment. It should look good in black-and-white, and extra-nice in colour. It should be something I can easily edit. There are a whole lot of things that need to be figured out: layout, font selection (must be a Google Web Font that I can use on my website as well), visual balance, what needs to be drawn.

So, what does mini-success for this project look like? Maybe an Adobe InDesign file (ideally, something that I can also convert to an Inkscape SVG!) with some text boxes in a selected font… I’ll probably need to do the final drawing of any illustrations, so maybe there are just boxes where the images go, too.

It’s a bit different from other things she’s worked on, then, where she designs the piece, writes the copy, and draws the illustrations. It can be odd working on something that seems like something you’ve done before, but isn’t quite the same equation. I know I’ve felt insecure about working on projects like that! If I’m clear about what I value, maybe that will help us make the most of the time we spend working on this project.

So I said:

If you’re worried that it’ll be too close to "Well, I drew these boxes on this InDesign file and tweaked them a few times until they lined up, and then you sweated over the copy and the illustration and all of those things I usually work on," I’m sure you’ll find other ways to create enough value to feel good about it. For example:

• "I looked at X fonts and shortlisted A – E. I recommend B because ______, but C is another good fit for you because _______. Both pair well with D if you need to use a different font for emphasis."
• "While working on this, I found some examples of marketing materials that you might like. _____ is interesting because of _____, _____ because _____, and _____ because ______."
• "You’re trying to say too much here. People only need to know ____, _____, and _____. We can save the rest for the website."
• "You’re not answering enough questions here. We need to bring back that point about ______."
• "Here are some sketches of what this could look like."
• "That sketch is unclear – doesn’t communicate ____ to me. How about these versions?"
• "I checked this with ______ and _____ and they understood it, too."

Who knows, maybe it will include answering specific questions about Illustrator and InDesign in case there are little tweaks I can’t figure out myself! That would be useful too. =)

In particular, the key values I think I’m getting from working with you are:

• Because you focus on graphic design, you’re probably exposed to lots more input and inspiration than I am. I’m counting on you to be able to pull out examples and ideas from your stash.
• For similar reasons, you may be better able to differentiate between things and explain why something is a better or worse fit. Think of the way people who are versed in colour theory can explain why certain combinations work and what they can communicate, or how someone who’s interested in typography can discuss different styles
• Because you aren’t me, you can push back if I’m giving too much or too little detail, using too much jargon, coming across with the wrong tone, or drawing something that people would find hard to understand. ("I hate to break it to you, but that doesn’t look anything like an elephant inside a snake…")
• You’re more familiar with the Adobe suite of tools than I am. You know what things are called and where they are. So you can get the basics in place faster, and you can help me figure out how to do things (especially if I don’t know what those things are called, or which approaches are easier than others).

Part of learning how to delegate is about figuring out where the task boundaries are, so that people feel good about working on and completing various chunks. I’m open to making the copywriting a separate project, and possibly even working with someone else for that. It’s tough, but if I learn how to break things down into projects that tap people’s strengths, and we figure out what makes sense to focus on, that’ll probably work out to a good thing.

There’s so much to learn, and it takes work to learn about delegation this way. I wish I could learn faster or more effectively, but I can’t imagine learning all these things in a class or seminar. Practical experience and mindfulness, then!

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?

Most companies try to be hush-hush about good people. That makes sense. You don’t want to train people and then have them headhunted away from you. Hiring can be expensive and distracting.

I want to see what happens if you turn that upside down. Other people have been asking me about my delegation experiments in scheduling, data entry, and other areas. I’m really happy with the virtual assistants I have. I wanted to them to find as much work as they want doing the kind of work they want. I’m happy to recommend the people that I like to the people that I like.

Will this come back to bite me? Maybe. My assistants’ workloads may get to the point where they don’t have time to work on my tasks because the tasks they do for other people are so much more interesting. My first reaction is to think of this as a bad thing, but when you dig deeper, it’s not actually that scary.

I’m reminded of something that I read in the E-Myth Enterprise:

People-oriented companies depend on "good" people to produce results, where "good" is defined as experienced, successful, self-motivated—in short, people who can be depended upon to produce good results. Someone is always shouting, "Find me someone who knows how to get the job done!" in a people-oriented company.

Process-oriented companies depend on good processes to produce results, where good is defined as the process’s ability to produce the very best results in the hands of inexperienced (or less experienced) people than the competition needs to produce the same results.

(p116, The E-Myth Enterprise: How to Turn A Great Idea Into a Thriving Business – affiliate link)

I don’t want to rely on just working with good people. I want to build up good processes that can harness good people. If I get to the point where I need to hire someone else because my assistants have become integral to someone else’s business or life, that’s not so bad. I’ll get more experience in hiring. Each person gives me another opportunity to improve my processes and learn from somebody new. I actually enjoy the hiring process, although it also makes me feel mixed emotions – such a candy store of talent out there! I don’t mind doing more of it.

It’s not like the churn that happens when you burn people out and discard them. I want to get to the point where working with me is an excellent launch pad, and where I have great onboarding and offboarding processes to make it even easier.

If any of my delegation experiments sound interesting and you think you might want to invest in trying that out too, talk to me. Share what you’re learning and what you hope to learn. If you sound like an okay sort of person – I don’t want to waste my assistants’ time in interviews or have them burned by someone who doesn’t work out – I’ll introduce you to the appropriate assistant, and both of you can see if it’s a good fit. =)

I think we’ve got this scheduling process sorted out, and I really really like it. It turns out that I didn’t have to fuss about with lots of templates or worry so much about exceptions.

When I’m reaching out by e-mail, all I have to do is cc: my assistant and add a short paragraph with details. She knows how to handle things. She knows my preferences for in-person and online meetings. She can follow up and make things happen.

So far, amazing. Things appear on my calendar! I can send Criselda a long e-mail with the AngelHack schedule for the weekend, ask her to pull out just the 2:15pm demo and block off 1h before / 2h after for travel, and it appears on my calendar with the venue information and other things I need to know. I feel comfortable asking her to coordinate with multiple people. This is good.

Here are a few things we’ve done to make it nice and smooth:

• I used Google Calendar to share my calendar with her so that she has full edit access to it without being able to access the rest of my e-mail. Stephan Spencer has his assistants process his e-mail for him – I’ll get to that level of trust someday!
• I set up an account for her on Google Apps. Because she uses a @sachachua.com address, I feel like I need to explain less about who she is, and I worry less about offboarding.
• I add the person’s name to the subject line: That way, when she’s reviewing her inbox, she can easily distinguish the different conversations.
• We use Trello to keep track of task status: I want to be able to see whom we’re waiting for a response from and the status of other tasks I’ve assigned her, and Trello makes it easy to do that. I do most of the Trello task updates, but I hope we’ll get the hang of updating the boards together.

Who’s interested in talking about delegation and scheduling? We can look into scheduling a Google Hangout!