Gotta Train the New Teammate? 5 Easy Steps to a Painless Knowledge Transfer
Ever been tasked with training a new employee?
Did they cry? Did you?
It’s a familiar scenario: Your company has hired someone new and your manager has asked you to train them. Maybe it’s on a new tool, your processes, or the role itself.
Easy-peasy, you think. You know this stuff backwards and forwards.
Two hours in, you’re both frustrated. Even though the eager new employee says they understand, you can tell by their confused, overwhelmed expression (and maybe the odd tear!) that they’re just not getting it.
You, on the other hand, are questioning your life choices, cursing your manager for making you do this, and silently judging that new employee’s abilities and general IQ.
Spoiler: It’s probably not them. It’s most likely you.
Teaching, like when you train a new employee, is hard. Teaching something that you know really well is, I think, even harder.
Why? Because you know it without thinking about it. You know all the clicks to make. All the forms to fill out. The location of all the files, the people to talk to, the decision points and outcomes.
You know it backwards and forwards,
So when you start to teach someone, it’s easy to skip steps. You know why you’re clicking a certain button, or accessing a specific document, or choosing a process to follow. Your trainee does not.
All those steps and decisions that now seem obvious to you, aren’t obvious to the newbie. And it’s easy to forget that. To forget the hours it took you to learn it in the first place.
In my role as a Technical Writer and Trainer it was a constant battle to get Subject Matter Experts to provide all of the information Users would need to complete a task. It’s not that they were purposely withholding information, but they had all of this background knowledge that made things obvious to them. Background information that most Users wouldn’t have and that needed to be included in the instructions.
Here are 5 things I do to make it easier for someone to learn, and also make it easier to teach.
#1: Remember Your Own Struggles
This can be tough, but think back to when you were first learning the topic: What parts were challenging? Where did you screw up? What stuff did you need to ask questions about or get constant clarification on?
Go back to old emails and notes around the time you were learning and look for patterns and issues that cropped up. If possible, talk to the person that taught you. Just be prepared to hear the statement: “Yeah, I thought you’d never figure it out.”
Remembering your own struggles helps identify areas you need to focus on or spend more time reviewing with the new person.
#2: Figure Out the Right Order of Info
Too often, we dive into teaching something and start in the middle, because that’s where we start now when we’re doing it.
But then 40 minutes in you realize there’s something they needed to know upfront before you can move on. So you go off on a tangent. An hour later, and another tangent. Pretty soon the trainee’s head is spinning from all of the tangents.
Some simple planning solves this.
Chart out the main steps: Step 1, Step, 2, Step 3… And for each step, ask yourself if there’s knowledge they need to perform that step that you haven’t already covered.
For example, if step 3 is “open the spreadsheet you need” and your file folder system is a hot mess, then maybe you need to first explain the system and how to find the spreadsheet they need.
You know what they say about failing to plan…
#3: Walk Through the Whole Process and Validate the Steps
Now that you’ve got all the steps plotted out, it’s time to validate that you cover all the steps you need and that they’re in the right order.
As someone who writes instructions for a living, I can’t stress this step enough. Yes, you’ve written out all the steps and thought about the order. But this is the big test.
Can you actually follow your own steps, start to finish, from the perspective of the learner?
It’s best if you can take a break between writing everything out and validating the steps. A day or 2 is best, so you can approach it with fresh eyes and a better perspective.
What’s even better is if you can get someone else to try and follow your steps - someone who maybe has more knowledge than a complete newbie, but who isn’t as familiar with the process. Either way, there’s an 86.9% chance you’ll find something you missed.
#4 Break it Into Digestable Chunks
An 8 hour mega-marathon of training isn’t fun for anyone. It’s exhausting, and it only guarantees someone will retain barely anything, like maybe only the first and last step, but nothing in between. If you’re lucky.
Are there ways that you can break things up so you only cover specific chunks at a time. If you think it’s going to take 3 hours, can you cover an hour a day for three days?
I know that doesn’t always work with training and sometimes you just have to plow through it, but the more breaks you can introduce, the better the retention will be.
#5 Use Repetition to Reinforce Learning
Here’s the formula I use for training:
I do it and you watch.
We do it together.
You do it and I watch (and I help only when necessary).
A lot of people just do the first step - run through everything once and then toss over the mouse and walk away. We’ve probably all suffered through that type of training, which is when the tears usually start to flow.
But when you can do all 3 steps is when you start guiding someone towards proficiency.
Once you’ve gone through it all the first time, the second round is to work through it together. Usually at this stage I’m still driving the process: I’m operating the keyboard and mouse, but I’m asking questions and seeing how much the trainee can guide the process.
The places they struggle are where I repeat key points and things they need to consider.
The final step is actually the hardest, especially for a control freak like me. Now you put them in the driver’s seat. And you only get to say something when they ask a question directly, get totally stumped, or really start going off the rails.
Other than that you have to sit on your hands and let them stumble through it. Don’t just jump in the moment they pause. They’re trying to access their memory and work out the next steps.
And that’s when the real learning happens. It’s your job to let that happen, so zip it!
Making It Stick
The purpose of training is to make the information stick - in one ear and out the other is definitely not the goal.
But it can be challenging, especially when you’re:
Not a professional trainer or teacher.
An expert (or at least really, really knowledgeable) in what you’ve been tasked to train.
Following these steps simply makes it easier for someone to learn. You’re removing barriers and creating a situation and environment where learning can happen.
And hopefully avoiding some tears along the way.

