Hiring and training someone new is always stressful.

You hope your hire will work and be successful, but you never know who will stay with you for a decade versus who you will need to fire in three months.

During my career as a serial software entrepreneur, investor in business-to-business SaaS companies, and fashion rapper-designer, I have had to hire countless people. I’ve interviewed thousands and hired hundreds of people, from video writers and editors, to corporate salespeople and senior software engineers.

Here are some lessons I’ve learned that can help you organize your new hire to be as successful as possible, while also saving you time with training future hires.

But even if that hire doesn’t work, these techniques will help you create more scalable training processes to find a better replacement for that person.

Document everything in writing (or with screenshots or video)

I cannot stress how valuable excellent documentation is. It’s my secret behind so much in my career and how I quickly scaled up a lot of my business and creative endeavors. My guides and executives have trained hundreds of writers and salespeople, dozens of editors, and even my cleaner.

Documenting things is the first step in creating a “living process,” which allows you to grow your business and make people replaceable. Smart CEOs don’t try to “do it all,” but constantly try to figure out what time-consuming tasks they can get off their plates.

Written documentation is also excellent as 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 young graduates, who are already trained to follow homework instructions and memorize the principles just like they did in school. It’s also great if your team members don’t speak English as their native language, as it gives them the ability to carefully read and search for words they don’t know.

As a copywriter I love to write, but you can also create great documentation with video recordings, screen recordings, and even annotated screenshots. I often use a combination of these elements in my internal guides.

The best part about good documentation is that you can reuse it. If your hire doesn’t work out, you can share it with his replacement. But be sure to review periodically and see what needs to be updated, especially right before you bring in someone new.

Always give real examples of what you like and what you don’t like

Whenever I create instructions for the training material, I try to add as many relevant examples as possible. It is important to give an example of the type of work or result that you would like to see, but also just as valuable in showing mistakes or failures to avoid.

These could be samples of your past work or that of your company, if you have it. But if you’re starting a new type of project or effort that you or your business hasn’t really done before, it’s only okay to list outside examples. Often times I just create google docs that link to samples which is also a handy way to give credit.

Remember to explain specifically what you like and what you don’t like about each thing.

Create a culture of questions

The best managers are a lot like teachers. They know how to ask questions that can tell you whether or not the person understands what you are explaining.

Pause to ask: “Do you have any questions?” or “Does this make sense to you?” better than asking nothing at all. However, shy people will often tell you that they don’t have questions or understand when they don’t in order to avoid embarrassment.

It’s best to ask questions that essentially try to ‘quiz’ your employees or contractors to make sure they pay attention to your instructions and really understand what you need from them. The point is not to put them on the spot and make them nervous or look bad in front of their peers. You can even make these questions a written assignment or “quiz,” where they can explain themselves in writing if they are quieter or introverted. At SalesFolk, this is how we have evaluated hundreds of copywriting candidates who we submitted to our copywriting training program via email after giving them access to our internal learning resources. The more questions contain real examples and ask them what they need to do, or what is wrong in that scenario, the better.

The opinions expressed here by the columnists of Inc.com are theirs and not those of Inc.com.



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