Scheduling stresses me out. I’ve had several calendar hiccups before: wrong dates, ambiguous locations, no contact information (or incorrect ones!), and so on. I want to fix that so that I can get better at meeting people and following up.

What would success look like? I think it would be awesome to get to the point where I can easily set lunches, coffees, and calls with people. This is how that process might look like:

1. I bump into people in person or get an email from them. If I meet them in person, I scan in or take a picture of their business card and add it to my file.
2. I introduce my assistant through e-mail and ask him/her to schedule lunch/coffee/a call. I use an e-mail template on my computer or a snippet on my phone to make sure that I include all the information necessary. My assistant also refers to a note with my preferences and processes.
3. My assistant contacts the person and negotiates schedule / location using http://scheduleonce.com or manual scheduling through e-mail, following up in case people don’t respond. If possible, we’ll suggest a venue with good WiFi near the person’s office or location. He or she would create a calendar entry for the meeting as well as travel/preparation time around it.
4. We have a task board where I could see where people are in the process, so I can be sure that nothing slips through the cracks. My assistant updates it, and we review it periodically.

It’s important to me that the process doesn’t make people feel like I’m standoffish or self-important. I also want to make sure that we don’t drop the ball even if I change assistants or take tasks back, so I want to use something like Trello to track scheduling status.

Here are some templates that I’m thinking of using:

Sample e-mail introducing the assistant and asking her to set things up

Hello, John!

I’d love to meet with you for lunch to discuss sketchnoting – my treat. Criselda (cc’d here) will be helping us set up something that works with your schedule. Criselda: Could you please organize lunch for maybe the second week of December? Thank you!

Sacha Chua

Sample e-mail from assistant

Hello, John!

I’m Criselda, and I’m looking forward to helping you and Sacha get together for a great conversation about sketchnotes. For lunch, would either Dec 10 (Mon), Dec 11 (Tue), or Dec 13 (Thu) work for you? 12pm usually works, but she’s happy to meet earlier or later if needed. Alternatively, if none of those dates work for you, you can check her availability at http://meetme.so/sachac or send me a few dates and times that fit your schedule.

Also, where will you be at that time? If you’ll be near your office at 123 Anywhere Street, I can find a restaurant nearby. If you’ll be elsewhere, tell me and I’ll look for somewhere close – anywhere near the subway line would be fantastic. Got a favourite? We’d love to find out about it!

What phone number would be the best to reach you at in case something comes up?

Best regards,
Criselda Hernandez

Sample calendar entry

Subject: Lunch: John / Sacha – sketchnotes
Attendees: john@example.com
Location: Restaurant Name (123 Restaurant Address St., Toronto)
Sacha’s phone: 416-823-2669
Your phone: 123-456-7890
Restaurant website: http://www.example.com
On Yelp: http://www.example.com
To reschedule, please contact Criselda at ______ . Need to reschedule on the day of the event? Please call Sacha.

<agenda / notes from e-mail>

Sample confirmation

Hello, John!

This is Criselda again. I’ve set up the calendar invitation for your meeting with Sacha for 12pm on Dec 13 at Restaurant Name. Please tell me if you’re having problems adding it to your calendar. If you need to reschedule, please feel free to get in touch with me. You can check http://meetme.so/sachac for Sacha’s updated availability. If you’re rescheduling on the same day, please call Sacha at 416-823-2669. Thank you, and I hope you have a great conversation!

Criselda Hernandez

What do you think? If I used a process like this to schedule something with you, would you feel weird about it? What would make it better? Have you delegated or are you in the process of figuring out how to delegate! I’d love to talk to you!

One of my business validation experiments has suddenly kicked into high gear. People love the sketchnotes I’ve been taking. Since they’re interested in illustration and event coverage, I’m happy to take advantage of that opportunity to learn more about business. I want to see where we can take this. In addition, I want to connect with way more people and find out how I can help them.

I’ve been investing more time into delegation as a way to buy time and share opportunities. One of the small processes I’d like to delegate is scheduling, which can be quite stressful for me. I often review my mail on the subway, and it’s difficult for me to look up locations or refer to notes. I worry about time zones and missed connections, so I want to make sure that there are calendar entries at the right time, with the right people, and with backup contact information. As I dig deeper into validating business ideas and connecting with people, I’ll be trying to set up appointments with so many people that I’d worry about dropping the ball, not getting back to people, or not following up in case people haven’t gotten back to me.

Software tools such as ScheduleOnce aren’t quite there yet in terms of completely handling the scheduling process. I want to be able to delegate appointment-setting to someone who can arrange times, suggest venues, make sure important information is included in the event description, and follow up as needed.

One of my friends was open to the idea of working as my virtual assistant, so I set her up on oDesk and gave her access to my accounts. It’s good to know people you can trust with your Google account. While you can delegate without giving full mail and calendar access, some things are just easier when people can find what they need. I did set up a separate email account for her so that she wouldn’t have to clutter her personal mail with all the requests.

Even though we’re just starting out, it’s such a relief to be able to forward her mail and know that she’s going to keep track of things. We’re not quite at a smoothly running process yet, but maybe we’ll get there in the next few weeks. I’d love to get to the point where I have a few keyboard shortcuts for templates that explain what’s going to happen (including details she’ll need in order to plan), and she’ll follow up and make it happen. I’d also like to be able to keep track of the people that we’re trying to reach and where we are in the process. She’s been busy catching up with other work this week, but I hope that as her coursework settles down and we work out the kinks in the process, things will run even more smoothly.

I’m also experimenting with automated ways to make it easier to arrange times. ScheduleOnce seems to be the most promising of the bunch. Doodle often gets timezones quietly wrong, and Tungle is just about to close its doors. I’m not completely sold on ScheduleOnce, but people seem to have the fewest problems scheduling with it. There’s so much more to setting appointments, though.

If we’ve got a lunch, coffee, or call coming up in the next month or so, I appreciate your patience as we experiment with the scheduling process!

I’m curious about this because I’ll need it in order to scale, and because it’s one of those universal things. How do people learn how to manage? How can I learn? I’ve read tons of books and blog posts. I’ve heard lots of advice and stories. We have a sense of what good management looks and feels like, and we’re all too familiar with examples of bad management. How do you bridge the gap from theory to practice?

How do you grow into becoming a good manager or a great one? Do we leave it to people who figured out the rules in grade school – “natural leaders”? We don’t get lots of practice or lessons in managing, probably because it’s so easy to step back and let other people make decisions. But the lack of management skills can get in the way of making good things happen, so it’s good to learn how to manage.

What does it look like to consciously develop this skill of orchestrating people’s work and energy? How can you gradually learn it in low-risk situations instead of waiting for workloads to force your hand?

I want to learn more about how to align people and help them grow while creating more value than one could create alone. The world is this candy store of people with awesome skills and possibilities. There’s just so much out there that I’d like to be able to draw on.

On one of my consulting engagements, we have a high school intern who’s doing wonderfully. I’m delighted to have the opportunity to help pick some of his tasks and delegate some things I’ve been working on. I learn from the way he does things, and I enjoy looking for ways for him to make the most of his internship. I haven’t been paying much attention to my outsourcing experiments over the last few months, but I bet that I could learn a lot if I paid close attention to it, going beyond transactions to help people grow. I’ve done that in the past with other assistants, and I really liked the results.

Here’s what wild success might look like: I find good people and help them grow their skills, either working on things I’d like to see happen or good things that people are willing to pay for. Success would be a great fit between the person and the work that needs to be done. They might grow enough to be able to handle these things on their own, in which case I can grow a network of freelancers, or they might prefer the benefits of working with a team. I find clients who have flexible timelines (so that I have time to coach or even do the work if necessary) and are okay with me delegating the work so that people grow, or I find a project I believe in strongly enough to fund and bootstrap until it’s been fleshed out enough to be worth investing in.

Step 1 might be to map people’s interests, skills, and growth plans. Step 2 is trickier. How can I put on training wheels so that I can try things with friendly clients on non-risky projects without taking on too much risk myself? I’m scaling down my consulting work, but I can postpone part of my next experiment if contracting is a better way to learn this. What if I focus on, say, Rails or WordPress stuff, with the understanding that I’ll pair-program with someone, maybe like the apprenticeship systems of the past? I’m fine with Rails, Drupal, and WordPress development, but new to independent contracting, so maybe I should approach it as a learner first – partnering up with someone for a few projects?

What about non-web development ways to learn this? I can delegate more of my processes, and see if other people would be interested in delegating or expanding theirs. That’s something I’m curious about, actually. People need help learning how to give good instructions and build working relationships. It’ll be interesting to see if I can do that in a way that adds value. I think that might actually be more promising than development because I won’t be distracted by the technical side of things. I’ll need to find out if people are looking for help in getting started with delegation. In terms of alternate business models, it might be an agency structure, process libraries, and e-books. Hmm… That would look like phone or Skype conversations about what people want to do, then coordinating with service providers. There are quite a few companies that do this already, but process libraries, automation, and growth might make a difference.

Worth thinking about some more…

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?

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! =)

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!

(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.