How to Support MSP Employees When Learning Feels Hard

MSP employees are asked to learn constantly, but rarely under perfect conditions. They are learning new tools, workflows, client expectations, and technical skills while tickets keep moving and urgent work keeps piling up.

Furthermore, MSP employee training is not just a task someone completes. It is an experience someone has to move through. That experience can feel awkward, frustrating, slow, and uncertain.

This is where the role of the MSP learning manager becomes so important.

MSP learning managers need empathy for the learner experience, especially the emotional friction that shows up when someone is starting from scratch.

This article looks at how to support MSP employees when learning feels hard, so you can help your team start, stick with, and apply new skills more effectively.

Read: The Role Your MSP Didn’t Know It Needed: The Learning Manager

Why Should MSP Learning Managers Remember What It Feels Like to Be a Beginner?

MSP learning managers should remember what it feels like to be a beginner because it helps them support learners with more empathy, clearer expectations, and better coaching. When you understand the emotional friction that comes with learning something new, you are better equipped to help employees move through confusion, frustration, and uncertainty without getting stuck.

Experts often underestimate how much they know. When a skill becomes familiar, the steps feel obvious. But to a beginner, none of that is obvious yet.

Try the Learning Journal Challenge

One practical way to reconnect with the beginner experience is to try the Learning Journal Challenge.

This idea comes from an episode of The Accidental Learning Manager, an Empath stream hosted by Empath Head of Learning Design & Innovation Keith Craig. In this episode, Keith is joined by Head of Sponsorships and Events Caitlyn Jopp to explore what happens when learning managers put themselves back in the learner’s seat.

Here is the basic idea:

Pick a skill that is genuinely unfamiliar to you. Ideally, choose something outside of work so you are not relying on your existing expertise. It could be a craft, a language, an instrument, a cooking technique, a physical skill, or anything else that puts you back in beginner mode.

Then commit to practicing for a short, consistent period of time. A good starting point is 30 minutes a day for two weeks.

The goal is to notice what happens while you are learning.

After each practice session, write down what you experienced:

• What felt easy?
• What felt confusing?
• What helped you make progress?
• What made you want to stop?
• When did your motivation drop?
• Where would an example or coach have helped?

Those small notes can reveal a lot.

Maybe the instructions were not as clear as you expected. Maybe you needed to see a better example. Maybe you lost motivation when progress was hard to measure. Maybe you got stuck because one small missing step made everything else harder.

Your learners experience those moments too.

What the Challenge Teaches MSP Learning Managers

The Learning Journal Challenge is really about noticing the learning experience more clearly. And once you notice it in yourself, it becomes easier to recognize what your team may need from you.

Motivation Has to Be Protected

It is easy to say, “Spend 30 minutes a day learning this.” It is much harder to actually do it.

Even when you are interested in a skill, finding consistent time can be difficult. When learning is assigned by someone else, motivation can be even harder to maintain.

MSP employee training cannot rely on motivation alone. If training is treated as something employees should squeeze in whenever they can, it will usually lose to more urgent work.

What to do:

1. Make learning easier to start, easier to continue, and harder to ignore. Start by protecting time on the calendar. Even a short, recurring learning block can signal that skill development is part of the work, not something extra.
2. Clarify the purpose behind the learning. Instead of saying, “Complete this course,” connect the training to a specific outcome: “This will help you resolve more backup alerts without escalating,” or “This will help you write ticket notes that make handoffs easier for the next technician.”
3. Check in before motivation drops too far. The goal is not to micromanage the learner. It is to show that the learning matters and that they are not expected to figure it out alone.

Learners Need to Know What “Good” Looks Like

One of the most frustrating parts of learning something new is not knowing whether you are doing it right.

A technician may document a ticket but not know whether the notes are clear enough. A team member may practice a client update but not know whether the tone is right. Someone learning a new workflow may follow the steps but not understand what a successful result should look like.

What to do:

Show sample tickets, model documentation, screenshots, walkthroughs, roleplay scenarios, or before-and-after comparisons. Point out what makes the example effective so the learner is not left guessing.

Instead of saying, “Write better ticket notes,” show a strong ticket note and explain why it works: it includes the issue, steps taken, current status, next action, and client-facing summary.

Frustration Is a Signal, Not a Failure

Learning something new almost always includes frustration. A little struggle can build confidence. Too much struggle can shut people down.

When someone gets stuck for too long, they may start to think the problem is them. They may avoid the task, delay practice, or quietly decide they are “not good at this.”

MSP learning managers can help by treating frustration as information.

What to do: 

Ask where the process broke down. Find out what step was unclear. Check whether they had the right example, enough context, enough time to practice, or a safe way to ask questions.

A simple check-in can help: “Where did this start feeling confusing?” or “What did you expect to happen, and what happened instead?”

Make Learning Easier to Start and Stick With

This topic was covered in an episode of The Accidental Learning Manager, an Empath-exclusive stream for MSP leaders, managers, and team members responsible for helping people build skills inside an MSP.

In the session, Keith and Caitlyn talk through what it feels like to start something unfamiliar, where motivation breaks down, and how those insights can help MSP learning managers support employees more effectively.

If you want to watch the full recording, it lives inside the Empath app. Start a 14-day free trial to view the session and explore the rest of Empath’s training built specifically for MSP employee training.

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