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…