Hiring and training someone new is always stressful.
You hope your hire will work out and be highly successful, but you never know who will stay with you for a decade versus whom you'll have to fire in three months.
In my career as a serial software entrepreneur, investor in business-to-business SaaS companies, and rapper-fashion designer, I've had to hire countless people. I've interviewed thousands and hired hundreds of people, from writers and video editors, to enterprise salespeople and senior software engineers.
Here are some lessons I've learned that can help you set up your new hire to be as successful as possible, while also saving you time with training future hires.
But even if this hire doesn't work out, these techniques will help you create more scalable training processes to find a better replacement for this person.
1. Document everything in writing (or with screenshots or video).
I can't stress how valuable great documentation is. This is my secret behind doing so many things in my career, and how I rapidly scaled many of my business and creative endeavors. My guides and frameworks have trained hundreds of copywriters and salespeople, dozens of editors, and even my house cleaner.
Documenting things is the first step to creating a "scalable process," which allows you to grow your business and make people replaceable. Smart CEOs don't try to "do everything," but instead are constantly trying to figure out what time-consuming tasks they can take off their plate.
Written documentation is also great because many people are visual learners. Likewise, introverts may be too shy to ask questions, but can always refer to your written guides for help. Good onboarding guides are great for recent graduates, who are already trained to follow instructions from assignments and memorize principles, as they did in school. This is also great if your team members don't speak English as their first language, since it gives them the opportunity to read carefully and look up words they don't know.
As a copywriter, I love writing, but you can also create great documentation with video recordings, screen recordings, and even annotated screenshots. I often use a combination of these things in my internal guides.
The best part of great documentation is you can reuse it. If your hire doesn't work out, you can share it with their replacement. But don't forget to periodically review and see what should be updated, especially just before bringing on someone new.
2. Always provide real examples of what you like and dislike.
Whenever I'm creating instructions for training materials, I try to add as many relevant examples as possible. It's important to give an example of the kind of work or outcome you'd like to see, but also equally valuable to show what mistakes or failures to avoid.
This could be samples of you or your company's past work, if you have some. But if you're starting a new type of project or endeavor that you or your business hasn't really done before, it's perfectly fine to list outside examples. Often, I just create Google Documents that link to the samples, which is also a handy way to give credit.
Don't forget to explain what you specifically like and dislike about each thing.
3. Create a question-asking culture.
The best managers are a lot like teachers. They know how to ask questions that can tell them whether or not the person understands what they're explaining.
Pausing to ask "Do you have any questions?" or "Does this make sense to you?" is better than asking nothing at all. However shy people will often tell you they don't have questions or that they understand when they don't to avoid embarrassment.
It's best to ask questions that essentially quiz your employees or contractors to make sure they're paying attention to your directions and truly understand what you need from them. The goal is not to put them on the spot and make them feel nervous or look bad in front of peers. You can even make these questions a written assignment that allows them to explain themselves in writing if they're more quiet or introverted. At SalesFolk, this was how we assessed hundreds of copywriter applicants whom we put through our cold email copywriting training curriculum after giving them access to our internal learning resources. The more the questions contain real examples and ask them what they should do, or what's incorrect in that scenario, the better.