As a follow-up to my post on what I've learned over the years about hiring people, this is a similar list of what I've learned about training and onboarding people as you welcome them into your organization.
Many organizations reduce training to a pretty simple process ("here's the training manual, here's your trainer, go"), but I find it to be one of the most complicated and fascinating periods in someone's life with an organization. The initial days, weeks of someone's employment (or, in a not-for-profit context, someone's time volunteering or serving on a board) are highly influential in shaping the experience they're going to have in the long run, and the work they're going to do.
It's a time when they start to reconcile their "outsider" impressions of what you do and how you do it with what they see as a new "insider" with fresh perspective. It's where any idealism and over-simplification that happens during the hiring process runs up against the nuances of internal processes and the texture of individual co-worker personalities. Training can prompt many moments of truth about the new person's image of themselves as a part of your organization: "do I belong here?" "are they going to like me?" "can I live up to hopes/expectations?"
From the perspective of the people doing the training, then, I think successful training is a careful balance between providing enough structure to properly educate and acclimate the new person to your organization while also allowing enough freedom and flexibility to accommodate their learning style, pace, interests and questions - especially the "why are you doing it this way when you could do it this other way?" ones.
Whatever you do, don't figure out training on the fly. Don't let it be a 100% self-directed experience in some hope that throwing someone fully into the deep end is the best way they'll learn. And don't underestimate the return on investment you'll get from an intentional, comprehensive approach to training.
As the process gets started, minimize assumptions. Communicate clearly and directly with the trainee (a word that feels a bit demeaning but is useful here) about every detail of their first moments as a part of your organization: where they should be at what time (and in what time zone, if you're a distributed team), in what medium the training will be conducted (in person, text chat, audio chat, video chat, in groups or one-to-one), how long the sessions will be, what they need to bring, and anything they need to do in advance. Give your trainee every opportunity to get past nervousness and make a great first impression by removing unnecessary vagueness in these critical first days.
Communicate expectations and set clear training goals. "Over the next X hours/days/weeks we're going to walk through everything from this to that. Your main trainer/mentor/buddy will be this person and they are your main point of contact for the process, ask them whatever you want. Here's the format we'll use, here are the materials we're going to cover, and here's a list of all the things we're going to touch on. Here's how we'll track your progress through this training, and here's what we expect from you at the end of the process." And then make sure all of this information is known to the wider team and company.
In my past positions, a lot of this was presented in the form of a training outline and handbook that we printed out and put together for the trainee. In my current work at Automattic, I created a training approach for my team that uses a Trello board (one per trainee) to make this all much more interactive. It includes a "Before their first day" list of cards for the primary trainer to work on, a list of cards for things to cover during the first few days, and a list of cards to cover in week one, week 2, etc. As each card is completed (and some cards have long check-lists, e.g. the list of all the tools/systems the new person needs access to), they get moved to a "DONE!" list, creating a nice sense of progress and perspective about the process as a whole. There's also a "Questions/Wonderings to Discuss" list where the trainee can create cards about things that occur to them outside of regular training conversations and need more exploration later.
We use the same source board for training multiple roles, and then label the individual cards as applying to some roles and not others. If multiple people are helping with the training, we can use Trello to "assign" them to those individual cards, making it clear who is going to cover what. And the whole team can access the history of card movement, to see how things are going and what's left to train on. We've received great feedback from our newer team members about the clarity and structure that the Trello approach brings, and we continue to refine it for use elsewhere in the company. (You can see Trello's own training board for their new hire onboarding.)
Make sure you have a comprehensive and up-to-date internal handbook that your new employee can read from day one, if not before. (If you don't have this resource already, you're probably leaking institutional knowledge in a way that needs fixing soon.) Don't waste valuable training time reading the handbook to someone; let them consume it at their own pace in a low-pressure setting, and then bring their questions and clarifications to your conversations. Take detailed notes about said questions, and use them to improve that documentation right away; this not only saves time for future trainings, but shows the new person that their feedback is valid and valued. Even better, make it a part of the training process to have the new person rewrite or expand a part of your handbook based on their experiences.
Related, where possible give the new person full access to the tools, information, spaces and systems that they need to be excellent at their job. It may seems scary to have someone you're just getting to know poking around in sensitive areas of your organization, and you can certainly implement reasonable guards against outright maliciousness or abuse. But if someone starts out with everything locked down away from their view and has to constantly ask for access to something in order to learn and get their job done, it will discourage their development and hamper the growth of mutual trust. And if you've gone through some kind of trial with the person during the hiring process, you've already decided that they're someone you trust and want to work with - why send mixed signals now?
Design your training schedule to be varied in format and intensity. Have sessions of the trainer(s) presenting material, conversations between trainer and trainee, guided collaborations on real-world work, and self-directed learning that the trainee can do at their own pace. Make sure the trainee hears more than one voice in this process by bringing in other people on your team or even people from completely different parts of the organization, if only so they get diverse perspectives about how the organization works. Have plenty of breaks, not only for accommodating biological needs but also to give everyone's brains a chance to absorb what's being said and come up with new questions/wonderings.
By design, you are probably going to overwhelm your trainee. Don't assume 100% absorption of training information. When humans communicate in everyday scenarios we still lose lots of information in those exchanges. Communicating and listening when you're in a new environment with new people trying to make a good impression while learning a lot probably means that someone is going to absorb and retain even less. A good training process will accommodate this and provide plenty of opportunities to revisit even basic details about operating procedures, organizational structure and technical job knowledge. It could even be worth having the same information presented in multiple ways throughout the process. Regardless, make the trainee feel comfortable with needing to ask about items already covered, and assure them that you know it will take time for it to all sink in.
Set up one-to-one check-ins along the way. Schedule times early on and at least weekly for the trainee to talk with their trainer and/or their lead about how the process is going. Give them plenty of opportunities to ask questions, express concerns or anxieties, celebrate successes, and clarify the steps ahead. Again, this is primarily for their benefit but also so you can learn about ways to improve your training process.
Have the new person write a post-training reflection that is visible organization-wide. They can talk about what they learned, what surprised them along the way, what helped them the most, and what suggestions or improvements they would make for the training process. Encourage candor and details. This can be one of those wonderful, rare times when the trainee is communicating what they see about your company from an "recently outsider" perspective, and everyone can learn from what's said.
Have a clear transition from training mode to regular work. Even though you may expect everyone in the organization to always be learning, I find it's important to have a transition from someone being "in training" into a place where they know they are ready to assume regular duties and be very proactive about filling in critical job knowledge gaps along the way. This could be something based on an amount of time that's passed in the training process, but is probably best left to a mutual decision between trainer and trainee about where they are in their knowledge and capabilities.
Connect employee successes and challenges to possible training improvements. As someone thrives (or not) at your organization, try to understand what about their training could have been a factor in that. When someone becomes a high performer, ask them what they learned early on that contributed. If someone ends up departing the organization, ask the same. Iterate constantly on your approach to training, and give it as much time and resources as you would any other critical part of your operations.