Four Tips To Make Your Transition From Solopreneur To Hiring a Small Team Go Smoothly (#26)

Posted by in Prose on Fire

I recently posted about my newest project—(slowly) hiring and building a small team. In that post, I gave you four rules for prioritizing your projects and deciding what to outsource. In addition to these four rules for determining what to outsource, I’ve also kept a list of tips and tricks that I refer to every time I create a new set of instructions for task-offloading that I’m going to share with you today.

Before I get into these tips, I just want to add the disclaimer that some of them may be counterintuitive or contentious. I never shy away from the controversial statements, so I have some pretty strong opinions about this topic! But please know that this is just what’s working for me right now. I also know of and have seen firsthand plenty of counter-examples to each of these points.

Do what’s best for you, always—but also, this is how I’m doing it and why!

#1 – Get Started Before You’re Ready

This is so, so hard to do, but I truly believe that everyone should get started before they’re ready, before they are making a full-time income with writing. If you’re focusing on income-generating activities, your team will truly be an investment and you will get your money back quickly, within a few months. This is perfect! You can then take that money and either reinvest it into your business or enjoy it. Of course, I recommend the former, because as you open new streams of income, you’ll truly be building your business and gaining more assets to leverage into larger successes.

I lived under the fallacy and limiting belief that I couldn’t afford to hire help. But when I explored more options, I realized I could do so at a fairly low cost/risk. For example, I was originally creating my own covers that were just decent. I went on Fiverr and found plenty of designers from other countries who could create significantly better designs for about $30-40, which I could then modify myself to create covers for the rest of the series. So I was able to upgrade to the next level without dropping $300 each on covers from 99Designs, or without spending $500+ each on covers from a freelance cover artist.

The same thing happened with hiring an admin to do several author services for me. I thought I would have to outsource to a third-world country and worry about security issues and language barriers, but I found a friend who was affordable and who could figure out a lot on her own. This saved me training time and stressing over having perfect and spelled out instructions, and I feel good about paying her for her services.

If you are completely struggling with how you could start now, grab the book Virtual Freedom by Chris Drucker. It will help you get into the right mindset for building your team and also provides a ton of examples and guidelines for how to work with overseas or virtual employees.

#2 – Pay People an Appropriate Amount on a Timely Schedule

If you’ve ever contacted me about bartering, you probably know that I turn down all bartering requests, regardless of what it is. I won’t trade my book for your book, I won’t trade consulting for accounting services, I don’t give away free copies just because you have a mailing list of 200 people and might mention it.

From my freelancing days, I learned that most bartering was a waste of time and always ended up making people feel icky eventually. I also realized that other people devalued my products or services because I was devaluing them by bartering them away. It messed with my mindset and made me feel like less of a business person!

When you pay people, it changes your mindset, because the numbers have to add up. You need to make your investment back, ideally at least 2x-3x over. This requires the focus I described before.

It also keeps people honest. You won’t have people randomly backing out, not finishing the job, or getting sloppy, because you’ve created a professional relationship and set the boundaries ahead of time.

There is so much more to say about paying people, which probably deserves another post entirely. But the last thing I’ll say about it is this: the “appropriate amount” and “timely schedule” are two critical factors. I’ve overpaid people, thinking they’d be appreciative and work harder on my tasks. I’ve also prepaid people for their work, thinking I was being generous. My generosity in both cases usually resulted in them taking advantage of me—many times never delivering the tasks they’d been paid for in the first place.

I’ve since learned that my “generosity” was just masked insecurity. I was using money to try to make people like me… and not surprisingly, it didn’t work and was keeping me poor and broke! Keep the relationships professional and proceed with standard business payment amounts and schedules. This is all about confidence and being a true business owner.

#3 – Outsource Tasks By Account

Without question, you will have to provide usernames and passwords when you get started with this. As someone who takes my personal information somewhat seriously, I like to limit my risk as much as possible in this area. For me, this meant:

  • hiring people I knew and trusted within the US
  • using a third-party service (like Fiverr or Elance) when working with strangers
  • limiting my tasks by the account needed (all the tasks can be done in LeadPages, for example)
  • providing only the necessary access needed to get the job done
  • creating or buying a separate user account when necessary, even if it cost me a bit more time/money
  • changing the password on each account to something unique and secure
  • making local backups of my data when possible (for example, when sharing a Dropbox account, I keep my own set of copies of ALL the content so I don’t lose it)

Lastly, I looked for tasks that could be done on non-critical accounts. For example, my email software is pretty important to me and provides my entire database of contacts… but my Babelcube account is non-critical and a security breech would not collapse my entire business. This means that I could outsource the task of adding all my available books to Babelcube, interacting with all my translators, and so on fairly easily, with only one of my less important accounts exposed. That’s a win!

Eventually I’ll probably bring others into my more critical accounts, but I like to test out people first. I advise you do the same and develop that trust with your employees over time!

#4 – Use Training Videos + Written Instructions

Most people learn best through either visual, audial, or textual content. When you provide the same information in multiple formats, you’re more likely to communicate clearly and get the results you want.

I use Screenflow + my microphone setup (get the full list of tools here) to record short screencasts of what I need done. In those screencasts, I attempt to:

  • Provide a simply overview of the tool and (more importantly) the sections of the tool I use and the ways I use them
  • Provide a full example that covers each of the tasks I want my peep to do (which may result in running multiple examples). Depending on how busy I am, I may either do this in one video or break it up into multiple videos to aid with understanding.

So far, this is working out really well and I’m pleased with the results. I find that it can take me about an hour to create training for a new piece of software and corresponding tasks, but as I do it, I make sure that what I’m creating is evergreen and will last for awhile.

If you don’t have the tools to create a screencast, you can also find the training library that the software has already provided. A lot of the time, this is sufficient to get your new employee started. I personally prefer to personalize the training because I want to shortcut the time that someone else has to spend digging around in training videos. Like most people, I tend to use a very small subset of any given piece of software, so the rest is just noise. However, even if you create your own training videos, it’s great to provide your new employee with a link to your software as an additional resource.

Check In Regularly

Whenever I send out a task, I create a reminder in my email inbox (literally a product called “Inbox” by the fine people at Google) to check up on it within a week (I usually set it for the following Monday).

I also ask that my peeps check in with me at the 3-4 hour mark of their billable hours, just to give me a progress update. As they are with me longer, I’ll bump that up to 5-6 hours, then 8-10 hours, and so on. This helps me understand whether they are having problems with my instructions, whether they are doing the wrong thing, and also how long the project might take before it’s done (or in maintenance mode).

Finally, I keep loose deadlines on my peeps, because I want them to be successful. I don’t assign tasks that need to be done immediately—if it needs to be done now, I do it myself. I instead assign tasks that I know I need to do, but that haven’t gotten done for months.

Urgency is the enemy when it comes to part-time help, especially at this level. I believe that unless your employee is full-time, you really can’t make assumptions about their schedules. You are not paying them enough to be at your beck and call, so be conscious and respectful of their other obligations. Especially if you are hiring for inconsistent, one-off work in small pockets, you know that your employee is making up the majority of their money through a different company or group of companies who are paying more consistently and guaranteeing a certain number of hours. Be understanding if someone takes priority over you—because frankly, that company probably should.

All of that said, you may want to put safeguards in place, like checking in once a week via email. If you have a deadline that you want something done, set a date with the other person and make sure you both agree on it. Check in at the halfway point to find out how much progress that person has made—this again helps you and them identify blockers, confusion, or lack of progress that will cause them to miss the deadline.

If you want to get started, I again recommend reading Virtual Freedom by Chris Drucker. It’s a fantastic resource to help you transition from solopreneur to full-fledged business owner. And I recommend starting earlier rather than later, while you can still afford time to create your training content and experiment without too much overwhelm. I’ve seen solopreneurs put off this task for too long and it always ends up creating a chaotic transition because the solopreneur has way too much work on his plate beforehand and can’t truly invest in training new team members. Likewise, team members end up being unsuccessful for all the reasons we’ve already talked about.

For me, hiring people falls under the same mindset reflected in, “dress for the job you want, not the one you have.” I believe that starting before you’re ready can really set you up for success over the long-term. Once the building is on fire, you’re not going to have the systems you need in place—so if anything, consider this insurance for your future business!

What do you think? Is outsourcing and hiring new team members something you can start in the near future? What would be the first thing you’d like to outsource?

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