Your Onboarding is Failing—Here’s What Your Team Won’t Tell You

Chad Silverstein recounts a summer job at a collections agency where he received only one day of training, learned by observing top performers, and later founded his company. He uses this story to argue that inconsistent, ad-hoc onboarding harms employees and the business; recommends documenting processes, using repeatable 30/60/90+ day onboarding frameworks, drip-feeding content at appropriate times, collecting team feedback, and using an LMS to scale and protect institutional knowledge. He explicitly endorses Playbook as an inexpensive, easy-to-use solution and invites viewers to try it or ask questions.
Chapters
I was a junior at Ohio State, and I went home during my summer before my senior year, and my friend got me a job with her dad at a collection agency. And I walked in and they trained me for one day, and they threw me on the phones and told me to collect on bad checks. People who wrote bad checks, there was like a $30 fee. I had to call them up and tell them they bounced a check. And this is back when people used to write their checks out and they had a fee and I had to collect on it. And I remember I wasn't trained for more than a day, and I had no clue what I was doing. I could talk to people on the phones, but I really had no clue what I was doing. And I remember looking on my computer screen and seeing how much money was being collected on a daily basis and seeing the commissions that the company got, and I thought that was my commission. I remember going home and telling my dad, I said, dad, I'm making a ton of money. And then I got my first paycheck, and I realized that was the company's commission. So I really had no clue what I was doing, and I had to figure it out. And so I found out who was making the most calls in the office, and I started asking tons of questions. I was really curious. I wanted to get really good. I sat my my ass down in the chair and I never got up, and I worked like crazy. And then I went back after my. My summer and. And that was how I started my company. I got an opportunity to start the company in Columbus, Ohio. And the reason I'm sharing the story with you is because training and onboarding people in your office is a really tricky thing because everybody's a different type of learner. I was able to get by with no training and figure it out, but I learned over time with my company, that's not the case with lots of people. And there is a real fear that people have when they come into a company and they don't know what they're doing, and they want to impress you, they want to work hard, but they're just lost. And the trainer or the resources and the process that you have suck. And so people get put through this miserable experience. It takes so much extra time that's unnecessary. And meanwhile, they're not given the proper tools and resources in order to get off on the right foot and do a great job for you. And so if you can change that in your company, that is a really big lift that you can give your team because that's something that you have to kind of rinse and repeat over and over and over as you scale your company and hire more people. And there's lots of tools for this. We at my company, I used a company that I talk about all the time called Playbook. And it was my solution. It was a lms, a learning management system that was really something that we could use to scale everything. All the experience, all the knowledge, all the tools, all the best practices, all the FAQs, we used it all. If you want to check it out, feel free to. You can check it out. In my community, it's free. You could do a free trial and see if it's for you. But you, you gotta have something. You have to have something to give your team the ability to not depend on one trainer who, if they leave one day, what are you gonna do? And so you pour all your resources into this trainer who you might have the best trainer in the world, but if that person leaves, they've got all your IP and then you have to start over. And if they've, you know, leave and they're not a good exit, that could be a real problem for any entrepreneur and anyone who's ever been held hostage by an employee who is the only one who knows how to do everything and they've been with you for so many years, that be a big problem for people. It's happened to me a lot. And so that's why you need to have some sort of a system. And one of the ways you can do all this is you put together a process. Whether you do a 30 to 60, 90 day, six month, one year, whatever process you want for your company, you want to have every new hire experience when they come into your company. And in a perfect world, you know, be trained by the same person the same way and hear the same thing so that you can measure and you can tweak it over time and perfect it so that you can take a 90 day process and you can shorten that down into 60 days, into 30 days and get people up and running fast. And our, our company, we were able to start training people before they even came in on the first day. Because we had this process documented and then we had it all recorded and we put people through an experience and then we gave that to them when they accepted the offer to come work for us. When they came in on day one, they were able to hit the ground running. Because if you think about all the things that you have to tell a new employee when they first start all the Nonsense, details that could be cut out if they could. Whether it's, you know, how to get around the office, who's who, what's the meeting pulse like? You know, how often do we meet, you know, what are the expectations, our core values, where do you go get lunch? I mean, there's just, if you think about how much information and why people are so overwhelmed when they first start working in a company, you know, again, it sense makes, makes sense why people can get really awestruck when they come into a company and you want to, you want to give people great experience. You want them to walk away their first day not overwhelmed with their head spinning. You want them thinking, wow, I've never had an onboarding experience like this with my company. So you have to work really hard to not only document your processes and then make sure that you're getting people the information the same way so they're not hearing different things from different people. And that's a hard thing to do. So you need to have some tool, some process, someone in charge of that. And whether you do it through videos, whether you do it through, you know, any type of a process oriented management system, a platform, an app, you got to have something. So if you're having problems right now with training and onboarding, there's a reason why it's not easy. And you have to also make sure that you get the feedback and the input from everyone on your team so that you're giving people the proper information in the proper sequence that makes the most sense. Because on day one, they may not be ready to hear about something that's really important. But on day 14, two weeks in, they probably are. And so you want to make sure that you drip out certain pieces of content in that process and you over time perfect it so that you have this process that's been proven to work. And as you keep getting better, you eventually get to a place where you got it. And then you just keep repeating that when new people come in. And that's really when you're company can kind of feel that traction and start really having momentum to bring new people on. And you won't be beholden to maybe one trainer or you know, the couple people who are the only people who have all the information and know how to train people when they come onto your company. So it's important to focus on onboarding and training. It's important to have some sort of tools and feel free to check out Playbook. It's, it's inexpensive and it's unbelievably easy to use. I've tested all the platforms out, have never found anything that I can start using right away and have playbooks up and running and just be so simple and easy and affordable. So I think that's a big win when you can find tools that can solve problems that you can afford and that work and that anyone can use. So feel free to check that out. If you have any questions, feel free to leave me a message in the comments.
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