Category Archives: delegation

Making lists of things I do so that I can learn more about delegation

The Great Big Extract of top-rated posts will wait a little while, as I’m working with a WordPress developer (in Bulgaria!) to make a plugin that will allow people to filter my blog by the ratings I’ve set. That way, it’s not just a one-off export. I want to be able to quickly filter my blog posts like the way people filter photos. Wouldn’t that be nifty?

I can probably figure out how to write my own plugin, but I also want to learn about delegating technical tasks. Delegating might involve more time, more money, and more risk, but it’s useful to learn how to delegate on small projects before I end up being the bottleneck on large ones.

I picked someone with good ratings on the oDesk freelancing platform, told him what I was trying to accomplish, set him up with access to my development site, and backed everything up carefully just in case. Let’s see how this goes.

It can be difficult to let go, so I’ve been working on identifying more tasks to delegate. I make long lists of different kinds of activities that I do or want to do – well over two hundred activities like “Analyze my data” in the blogging category and “Clean the litter boxes” in the routines category.

Now I’m fleshing the list out in more detail, starting with the business category. I organized the business activities into the “earn”, “build”, and “connect” subcategories, which I’d been finding useful for my weekly reviews. Focusing on the “business – earn” category, I listed quite a few tasks that I can eliminate, automate, or delegate. For example, while I might outline a talk, I could get an assistant to look up prices and trends, design nifty graphics, or transcribe the presentation.

After I analyze my “business – earn” tasks, I’ll look at my “business – build” tasks. That will probably be harder to delegate, but maybe I’ll find surprising opportunities.

Optimizing non-business tasks such as cooking can also free up time that I can use to build the business. I want to make sure that I don’t end up tilted too far towards business, though, because life is awesome.

Listing all these activities makes it much easier to think about them. Which of these things are core? Where do I have an advantage, and what can other people do much more effectively than I can? What are my processes for these different activities, and how can I improve them? Can I estimate how much time I spend on these activities, and how can I time myself at that level of detail in order to verify my estimates?

One of these days – maybe after I’ve added some time estimates or measurements, or I have some more delegation experiences to report — I’ll put together a braindump of activities so that you can see what it’s like.

In the meantime, you might enjoy playing around with the idea yourself. Think about the things you regularly do, and make a list of as many things as possible. For each item, ask yourself:

  • Is this really something I need to do?
  • Can I automate most or all of the task? How? Is it worth the time/money/attention tradeoff?
  • Can I outsource or delegate it? How? Is it worth the time/money/attention tradeoff?

A perspective on outsourcing

Mel suggested that I write about delegation and outsourcing to virtual assistants because I approach it in a different way. I’ve read many of the same blog posts and books that she must have read, mostly written by entrepreneurs trying to squeeze as much value out of their time as possible and who want to eliminate pesky necessities like housekeeping or cooking.

I happen to like cooking. I get intrinsic value from many of the activities that people typically outsource: cooking, gardening, writing blog posts, responding to e-mail, developing websites… I also don’t mind living a small-scale life, a life where there’s room to breathe. I don’t have to do it all or have it all.

What are my reasons for delegating, then?

I want to learn how to give instructions and let go of tasks, because the feeling that I need to do everything myself will be a bottleneck if I allow it to be.

I want to get things done better than I can do them myself, taking advantage of skills that take people years to develop and experiences that I will never have.

I want to work around the limits of my attention. Sometimes I shelve projects or procrastinate tasks. Paying someone to do things not only gets those things done, it also strengthens my own commitment to move things forward.

Part of this motivation to learn how to outsource things comes from more deliberate choices about what I want to focus on and more awareness of what tends to fall to the bottom of my to-do list. In my sketchbook, there’s a page divided in two: things to say yes to and things to say no to. For example, I accept that I’m not going to invest the time into drawing realistic figures or painting work as beautiful as the ones I see hanging in the art galleries (“no” pile), and I’m going to focus instead on simple, quick drawings that capture ideas (“yes” pile).

Deciding not to try to do it all – picking some things I’m going to focus on, at least for the next year – makes it easier to choose tasks to outsource. If I want something done but I’ve chosen not to budget the time to learn how to do it well, then the real question is whether I want it strongly enough to pay someone to do it this year or whether it’s something I can postpone until I reevaluate my learning priorities. Here are the reasons why I might delegate something:

  • Time premium: Is there value to having it done earlier than I can make the time to do it or learn the skills I need in order to do it?
  • Skills: Can other people do it much better than I can?
  • Relative advantage: Can other people complete it in less time or for less cost than I might?
  • Energy: Is this something that energizes other people much more than it energizes me?
  • Interruption / task switching: Can delegating this free up my attention so that I can focus on larger chunks?
  • Opportunity cost: Would I be able to earn more or enjoy a different activity much more if I spent time doing that instead of this?
  • Documentation and repetition: Is this a repeatable process? Is it worth investing the time in documenting the process and debugging the instructions?
  • Learning: What can I learn from delegating this?

Here’s a short list of activities I’ve been thinking of delegating:

  • Reminders
  • Appointments
  • Data entry
    • Typing in text from scans (receipts, evaluations, business cards, etc.) or sketchnotes
    • Contact information
    • Comparison-shopping
    • Transforming text
  • Web research
  • Text formatting
  • Transcription
  • Data collection and analysis
  • Proofreading and editing
  • Illustration
  • Graphic design
  • Web development
    • Web design
    • Turning sketches into mockups or HTML/CSS templates
    • HTML5/Javascript development
    • Rails development
  • Setting up get-togethers with friends

I’m also interested in local assistance for:

  • Occasional batch cooking, so we can try different recipes and enjoy more variety
  • Cleaning
  • Other chores and errands

I’ll gradually work up to delegating different activities. Gotta work on my comfort level and ability to give instructions, after all! =)

Starting up my delegation experiments again: data entry from receipts

We decided to skip the community-based and culture program this season, and instead buy the vegetables ourselves. I wanted to track how much we buy of different kinds of vegetables to see if we were still getting through a good quantity without the forced commitment of a box delive red bi-weekly. Tracking this means tabulating data from grocery receipts, though, and that can be a lot of typing.

Two weeks ago, I posted a job on oDesk, where I’ve hired virtual assistants before. I like oDesk because you can find a lot of potential contractors there and you can monitor people’s work. This was my job post:

Typing text from images (scanned receipts, etc.), occasional web research

Looking for someone who can type in text from scanned receipts and other images into a spreadsheet. Should be proficient in Microsoft Excel or OpenOffice/LibreOffice. Should have a Dropbox account and be comfortable using it. To show your attention to detail and give me a basis for comparison, please start your reply with your approximate WPM. Around 1-2 hours a week, no urgent requests so you can fit this around your other contracts.

By afternoon, 150+ people had applied. I narrowed it down to a shortlist of fifteen applicants based on whether they followed my application instructions, avoided gendered assumptions (so many people start their applications with “Dear Sir”; yes, I have an ambiguous nickname, but still!), and had competitive rates and typing speeds. I interviewed a few by e-mail, then hired a couple of assistants for a short trial.

The task I assigned to the first person was that of typing in line items from the grocery receipts that I scanned. I shared the folder of scanned receipts using Dropbox, and I created a sample spreadsheet with a few items. He asked a question to clarify what to do, and I answered it before going to bed. By the time I woke up, he had completed the spreadsheet and moved the receipts to the “done” folder. Total time for eleven receipts: 0:50, or roughly $0.70 of work. By golly. (I gave him a $2 bonus for good work and to start the relationship off well.) I added another eleven receipts, and he completed those in 0:50 too.

Here’s the spreadsheet. See the INSTRUCTIONS tab for details. I filled in the Lookup table afterwards so that I could easily categorize the results.

There are some web and smartphone apps that digitize receipts, like Shoeboxed or Lemon. The premium plan of Lemon can extract the item-level details, but the FAQ / help forum says that item-level export is still in the works. I haven’t found anything that has great item-level export. Having someone fill in a spreadsheet handles all the edge cases, like crumpled receipts or handwritten notes.

I’ll share more delegation experiences as I experiment!

Sketchnotes: Sal Sloan of Fetching! at the Toronto Public Library: Small Business Networking Event


(Click on the image to see the larger version)

The Toronto Public Library hosts monthly networking events for people who are interested in starting a small business. Most people have not yet started a business. It’s a good opportunity to ask questions and learn from someone who has figured some things out.

Sal Sloan came up with the business idea for Fetching! when she got a dog. She had signed up for a fitness bootcamp, and the combination of exercising herself and walking her dog wore her out. Why not combine the two activities – help people exercise with their dogs? With a $10,000 loan from her parents, Sal started Fetching! by focusing on exercise for people and obedience training for dogs. With early success, Sal broadened her scope to focusing on helping people have active fun with their pets. She has been doing the business for two and a half years, and continues to work part-time on another job. This helps her grow the business organically by avoiding financial pressures.

One of the lessons I took away from the conversation was the power of delegating work to other people. Sal knew that other personal trainers could run sessions much better than she could, so she hired good people whom she could trust to represent her company. She’s looking for someone who can help her with the business side so that she can grow more, too. After I bank some money from this consulting engagement, I might start my delegation experiments again.

The session was an interesting contrast to last month’s meetup with Kristina Chau of notyouraverageparty, who had been in business for three years and who was struggling to scale up beyond herself. Sal has clearly put work into figuring out how to scale up, and it’s great to see how it paid off.

Starting up my experiments in delegation again; the difference between what I want to do and what I want to see

Prompted by my sister Ching, I’ve been thinking about delegating again. She’s looking for a virtual assistant who can help sort out the details of their move to California – research cellphone plans, set up appointments, that sort of thing. Me, I’m generally curious about programming, and delegation is taking that to a different level. At its best, delegation will even let me “program” things that I don’t know how to do. It’s like being able to write a routine like doSomethingAwesome() and take advantage of other people’s proprietary microcode!

I’m going to ease up a little on long-term investments and carvie out a chunk of my budget for learning how to get other people to get things done. Besides, with all sorts of weirdness going on in the markets, it’s probably going to heck in a handbasket anyway. ;) I’m still investing for the long-term, but I’ll redirect some of it to education. Books and classes can’t teach me how to scale up, but working with people can.

I thought about what was making me hesitate:

  • Money: Although you can hire inexpensive contractors, it’s still a non-zero cost. I compare my estimated costs with eliminating the task, doing it myself, or putting it off until it makes more sense.
  • Time: It often takes me less time to do a task than to write instructions and debug people’s output. I don’t feel pressured by time. The limit of 24 hours each day just means that I get to some things sooner, some things later, and some things not at all.
  • Trust: There’s the obvious level of difficulty in trusting other people with passwords and financial information, but there’s also the other level of trusting them with communication on your behalf.
  • Trying to figure out what to outsource: Web research is a natural candidate for outsourcing. Learning, well… the work is inside your brain.

So here’s how I’m starting to think:

Money: Yes, the cost of delegating might be more than the direct value of the time I’d save in the best case. But (a) it will help me learn how to scale beyond the hard 24-hour limit we all have, (b) it’s cheaper than an MBA, and (c) it flows money to people who appreciate the work. Looking at the job postings and people’s resumes, I feel like I want to give people much more meaningful work than spamming blogs.

Also, it’s a little embarrassing to write about delegating work. People assume you’re one of Those People with executive assistants and all of that stuff. I’m sure we can work that out.

Time: Yes, it can take more time to write instructions than to do a task. It also sometimes takes more time to write a program than to do a task, and I’ll still happily write a program anyway. This is like writing people-code. Maybe I won’t reuse instructions as much as I hope, like the way some of my scripts are ad-hoc. If I blog about them, though, people can use them as starting points.

Trust: This one’s easy: start with low-risk tasks.

What to outsource: Brainstorm lots of ideas. Plan small chunks of work so that I don’t feel self-conscious about running out of good things to delegate. Test my assumptions.

I’m starting to understand another paradigm shift I need to make: the shift from thinking about “How can I outsource what I do?” to “How can I fund what I want to get done?

There’s something there that I didn’t know the first time around. You see, I’d been thinking about outsourcing as a way to support what I want to do, and the interesting goals are the ones where the most work happens inside me. Thinking of outsourceable tasks was difficult. I didn’t really resonate with the advice other people were giving on virtual assistance. I don’t run a business, I’m fine with work and with what I do in my free time, I actually get decent sleep… It’s not about freeing up space so that I can do what I want to do, because I’m already doing that.

Here’s a different thought: If I switch to thinking “How can I fund what I want to get done?” – to think of myself as a capitalist in the sense that I can provide the capital for a change in the world – ah, now that opens up possibilities… It’s a little like considering myself like a Kickstarter or an Awesome Foundation on a tiny tiny scale.

Going back to my sister, for example: I may not directly want to compare cellphone contracts for her, but I do want her to enjoy a smooth and not-very-stressful move. Moving halfway around the world is tough. She and her husband have moved before – from the Philippines to Singapore – but this involves a busy time (right after our other sister’s wedding), lots more timezones, a really long flight, and other things. So we can delegate tasks that would make her life better.

I would like our family stories recorded and written down. I may not have the skills of a professional interviewer or the patience of a transcriptionist, but maybe someone can help me make that happen.

I want my blogging, quantified-self-tracking, and Emacs life to be awesomer. I can dig in and code myself (balancing that with my other coding interests and with IBM), or I can sponsor improvements that help other people.

I want my blog to be more visual. =) I want my presentations transcribed. I want other people’s presentations transcribed, like my mom’s lectures and my dad’s speeches.

I want our chest freezer full of individually-packed home-cooked meals, and I want to enjoy more variety.

I want to put together more tips on happiness, and connecting for introverts, and geeking out in life, and all these things I don’t read enough about in published books or hear about enough in conversations.

Time is an obvious bottleneck, but I’m a bottleneck too. If I dream dreams that I can’t do by myself, though, then I can make more things happen. Some things resonate with people and they voluntarily take up the cause – my dad is amazing at moving people to make a difference – and some things happen faster if you compensate people for doing them. It’s a little like moving from “What do you want to do?” to “What do you want to happen?”

Let’s see where this idea takes us.

Thinking about getting better at writing

Photo (c) 2009 Markus Rodder – Creative Commons Attribution No Derivatives Licence 2.0

I want to become a more engaging, more thorough, and more organized writer. I want to be able to write clear and insightful essays – not high school book report essays, but discovering-life essays. I want to get good at capturing all this raw material that flows through life, and digesting them so that I and other people can learn.

Practice is essential, of course. Stephen King writes:

If you want to be a writer, you must do two things above all others: read a lot and write a lot. There’s no way around these two things that I’m aware of, no shortcuts.

I’m not looking for a shortcut. I’m looking forward to decades of figuring this out. If I remember to keep backups along the way, it will be fun to review the archives.

Deliberate practice and feedback would be good, too. A few weeks ago, I posted an oDesk listing for a personal blog editor and writing coach. I’m not particularly impressed by any of the candidates. Part of it is because I’m not yet clear on what I want.

Part of it is because what I want is different from what most people writing blogs want. I don’t want to write a niche blog that rockets to the top of Google rankings and becomes a passive income stream through affiliate marketing, ads, or information products. I’m not failing with my current blog, and I’m not looking for help “fixing” it. I’m doing better than I could’ve imagined my notes could do. Who knew so many people would keep coming back and reading? One of these days I might discover what you like about this blog – or maybe you can tell me, and I can think about doing more of it.

Here’s how I want my blog to work, in some ideal future: I’ve got an excellent capture workflow that encourages me to write about everything I’m learning. A subset of this is published to my blog, where interested passers-by and the occasional searcher can find (a) technical snippets that save them hours of work, or (b) reflections that make them go “hmm” or “aha”. My evil plan is that people might discover other interesting posts along the way and will look up from their browser window several minutes or hours later having learned about all sorts of things they wouldn’t have thought of searching. I will settle for going through that same discovery process myself, as I find things I’ve forgotten writing.

How can someone help now? I want someone to read my planned posts and tell me: here you need to explain things more. Tighten this up. Take this out and put it into another post because you’re trying to do too much. Get rid of “nice” and use a real word.

But more than this surface-level editing, I want logical editing. What’s your point here? It doesn’t make sense. That argument doesn’t support your conclusion, so get rid of it. That’s a fallacy there. Let’s work on that metaphor. If you reorganize it like this, everything falls into place.

And then I want meta help: on how to ask interesting questions that lead to exploration, how to capture as much learning as possible, and how to organize all of that so I can make sense of it later. Like Lion Kimbro’s How to make a complete map of every thought you think, except maybe less rigorous and more technologically-assisted. I want to be able to work with an archive spanning years and years.

I could edit myself. I have old entries I’m no longer attached to, and future ones that I can examine closely. I keep looking for ways to improve my system. I can just throw a lot of time and effort at it, and become much better in a decade or two.

It would be good to work with other people, though, who can be more ruthless. It would be great if they’ve spent lots of time figuring out their own workflow and system for keeping everything organized and they can tell me the pitfalls I should avoid or address.

I haven’t found anyone I really want to work with. I don’t think I’ll find other people who are passionate about this kind of braindumping on oDesk or any other freelance site. (Particularly geeks who can also help me tweak my Emacs setup to totally rock.)

Sometimes it feels like I’m going after the fiddly bits, that last 20% that will take another 80% of effort. I’m a good-enough writer, and my notes are organized well enough. The blog is searchable, and I’ve got structured text files holding almost everything else. Sometimes I worry that I’m leaning towards perfectionism and indistinguishable differences. But then I read people who are better writers, and I think: I’ve barely begun.

No substitute for writing, reading, or living. I’m going to have to do the hard but fun work: reading interesting people and figuring out what I like about them, living, writing about life, revising, tinkering around with some kind of organizational system.

Ah, well. I guess there are some things you can’t learn from books. There are some things you can’t even learn from teachers.