Conversational Apps, or How To Practice Outsourcing For Free

I’ve been a pretty big fan of outsourcing since I first picked up 4-Hour Workweek during my Junior year in college. Anyone who knows me knows I have an obsession with process and task management. It’s borderline unhealthy at times, but god if I don’t love crafting roadmaps and checking off boxes.

I think more people should consider practicing outsourcing, especially if you want to get better at process creation and management. It’s easier and cheaper than ever now to get experience doing this at a small scale. It’s also a lot of fun. I’ve found that the recent boom in conversational apps (aka invisible apps, human-powered chat bots, etc) provides a great starting point for anyone looking to practice delegation in your personal/business life. I’ll cover a few of my favorite options in a bit. Here’s a bit of background on a few of my limited but humorous outsourcing experiments over the years:

Outsourcing Business Development Research to India

In college I used to get local business research done on the cheap. A simple task- use help to find all of the restaurants in my hometown, then create a spreadsheet listing their address and phone number. I learned very quickly that if you think you are being specific enough, you probably aren’t (i.e. Apparently it helps to specify that Thai massage parlors and Thai noodle houses are not in the same industry).

Hire Interns For A Business That Didn’t (Yet) Exist

Not particularly proud of this one, but it’s one of the best decisions I’ve ever made. Back when I was hacking together a few business ideas at Dartmouth, I hired a couple eager Freshmen interns for PromoteU, a business focused on connecting local shops with college students for marketing advice. In retrospect I think it was probably a bad idea to hire “interns” for a project that barely had any sort of plan or roadmap. In all honesty I did it so that I’d be forced to put a plan together, and at the very least it accomplished that. I was fortunate to have worked with two individuals that are undoubtedly two of the smartest people I’ve ever worked with, but it could have worked out very differently. Just for the record, it was a part-time internship that was located on campus, so nobody had to relocate or do anything crazy. Ethically I was in a gray area, but not in the red.

Outsourcing Lead Generation To A School Teacher

I paid a high school teacher in Kansas via Upwork to craft a targeted sales database of Fortune 500 university recruiters while I was running Wrangle. For the contractor it was relatively easy work for a fair rate. For me, it was stats that encouraged us to pursue our sales strategy and ultimately land meetings with high level execs at LinkedIn, GAP, Salesforce and more. Seemed like a lot of the work was getting done during class hours, but who am I to judge.

There have been more experiments like the ones above, but overall I’d say I’ve consistently had mixed results that at the very least provided me with good stories. The problem overall though is that for many of my friends and colleagues, these aren’t exactly inspiring examples- they required cash, a decent amount of time and a clearly defined project. Recently I’ve been inspired by a new wave of applications that I think are a better entrance point for anyone trying to practice outsourcing in daily life. Here’s where I’d start if you want to get better at having other people do tasks for you (for free):

Service App

Outsource Your Customer Service Complaints

Nobody likes waiting on hold. Navigating confusing phone trees just to get to a person who says they can’t help you sucks as well. Service has solved all of these problems for me.

It’s a pretty simple concept- you open the Service app and explain your customer service issue with a Service rep. They will then do what they need to do to resolve the issue for you- calling the company in question, emailing them, tweeting at them- whatever it takes to resolve your issue. I’ve had a wild amount of success with this, and have gotten over $100 back by just sending a few texts.

Operator App

Outsource Your Shopping & Purchasing

Sometimes you need inspiration for a gift. Other times you want to get tickets to an event but you’re on your phone and don’t want to navigate the horrific Ticketmaster user experience. I use Operator for this. Currently free of fees, Operator assigns an “operator” to you that will do research on products and then actually complete transactions for you. I’ve asked them to buy tickets to comedy shows, find the lowest price on the internet for a particular item, and more. Basically, anyone can now have a personal shopping concierge, for free. scheduling assistant

Outsource Your Meeting Scheduling

Back and forth on meeting scheduling is a massive pain. is solving this by allowing you to cc an AI-powered personal assistant to do the job for you. She’ll (it? Should I be humanizing an AI?) reach out to the person you are trying to meet with and find a time that works for both of you, and then send out the invite. It works surprisingly well, and saves a lot more time than you might realize. I’ve now also said thank you to a robot multiple times.

These are just a small handful of ways people can start to practice “letting go” and handing off their tasks to someone else. It’s easy in the beginning to say to yourself “but I could do it better” or “I’m not sure I’d trust the work or advice of the whoever I’m outsourcing my task to.” I struggled to get over this, until I started reminding myself of one simple thing- what’s the worst that happens? You don’t like the work or results you’ve been given? You discover that you have to be more specific in your request? It’s likely that you can handle the consequences.

I think the future of conversational apps is pretty exciting- as technology improves, we’re starting to figure out how to scale 1:1 human interactions, and that’s pretty damn awesome. A positive externality from all this is that more people will get a chance to practice outsourcing to other humans, and in the process get basic process management experience. Check out the apps and see what you can do.

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