10 Ways to Upskill Your MSP Employees & Gain a Growth Mindset
Jul 24, 2025
In our latest podcast episode with Dean Trempelas, Head of MSP Success at Empath, he made a great point: when technicians (most likely) start their own Managed Service Provider (MSP) business, they are focused on being their own boss, providing top notch tech support, and taking care of businesses. What they don’t focus on? Being a people manager. They want the increased clientele but don’t anticipate the skills required to lead a growing team of people. Therefore, what Dean sees time and time again is an inability from leadership to help their own employees upskill. And what does not grow, grows stagnant.
MSP owners–your employees want more than a job. They want a path forward and a purpose behind their nine to five. They want to be proud of the work they do–instead of just feeling stuck in a dead-end job because they have bills to pay.
But how do you help them upskill, stay engaged, and build meaningful careers?
In this blog, we’ll walk through how to create that kind of environment, even when your days are packed and your team is pulled in ten different directions.
In this blog, you will learn:
Why growth and retention go hand in hand
10 practical ways to support your team’s development
How Helpt and Empath can support these goals
Why Having a Growth Mindset Positively Impacts Retention
It’s no secret: turnover is expensive and time-consuming. It also impacts office culture. When someone leaves, the knowledge goes with them. Morale can take a hit. Client relationships may suffer.
The best defense? A strong culture of internal growth.
When MSP employees feel like they’re growing, they are more likely to stay. They’re also more productive and engaged.
10 Practical Ways To Support Your Team’s Development
Build a Strong Foundation Through Onboarding and Training
Hiring is just the start. What happens after someone joins your team is what really sets them up for success. The worst thing that can happen for a new hire is, at day 30, 60, or 90, for them to realize…“Oh…this is the job? This is not what it seemed like at first…”
Invest time in onboarding. Set measurable goals and reasonable expectations. Offer training that is both technical and soft-skill-focused, especially for client-facing roles. The time you invest in this part of the process will save you time later down the road.
Let Go (a Little) and Delegate with Intention
Delegation is part of growth. If you are still holding onto every decision or redoing your team’s work, they will never feel trusted. Plus, you’ll burn out! Once you have trained someone well, let them run with it. Step in when needed, but resist the urge to hover. That trust helps people take ownership and pride in their work.
Practice Empathy for Their Bandwidth
Too often, leaders don’t realize what is on someone’s plate. Or if they do, they don’t know how much work behind the scenes has to happen to get it done. That is when resentment builds and performance drops. Instead, ask them:
“What are your top priorities this week?”
“Are there roadblocks I can help remove?”
“Does anything need to shift?”
This will help your team feel seen, understood, and appreciated, as well as help you prioritize routine tasks alongside ongoing projects.
Match Your Management Style to Their Needs
Not every employee needs the same level of oversight. Some folks love regular check-ins and structure. Others want more autonomy. Ask your team members what works for them, and adjust accordingly. A quarterly 1:1 might be perfect for one person, while another thrives with weekly touchpoints. Adapting to their needs shows them you care more about their success than your own preferences or natural inclinations.
Provide Employees With Mentors Who Aren’t Their Manager
It’s one thing to have a supportive boss. It’s another thing to have someone else you can go to for advice and encouragement. Assigning mentors from other parts of the company helps employees gain new perspectives and build connections outside their direct chain of command. It also makes it easier for them to ask questions they might hesitate to bring up with their manager.
Celebrate Progress, Not Just Results
Sometimes the biggest motivator is knowing someone noticed. Tell your team when they have done something well. Be specific. Did they handle a tricky client call like a pro? Meet a tight deadline? Help a teammate? It doesn’t take long, can brighten their day, and motivates them to continue doing well in the future.
Create Feedback Loops That Go Both Ways
Performance reviews should not be:
A surprise
Sporadic
A one-way street
Ask your employees: “What’s working?” “What is getting in your way?” “What do you need from me to succeed?” Build these conversations into your process. And show that you, too, are open to feedback (and willing to act on it)!
Support Their Goals with Time, Money, and Structure
Your employees may have aspirations beyond their current role. Ask what those are, and help them get there. That could look like:
Time set aside during their 8-hour shift for training or certifications
Professional development funds
Flexible time for job shadowing or involvement in new projects
Clearly defined paths to promotion or specialization
The more you invest in them, the more likely they are to invest in your business.
You know what else this means? You should be continually investing in yourself too. Prioritize the ongoing betterment of your people management skills, not just your cybersecurity or AI knowledge.
Encourage Cross-training Through “Lunch and Learn” Sessions
Not every training has to be formal or time-consuming. One of the easiest ways to upskill your team and spark curiosity is to host these casual sessions. These can be led by anyone at your company, whether that’s someone in tech support or a marketing specialist, or even a guest speaker that pertains to your industry. It encourages your team to teach each other through knowledge-sharing, builds confidence, and helps your employees see the bigger picture of how your MSP runs.
Model the Work-Life Balance You Want for Them
Having a business that requires 24-hour answering services does not have to mean a 24x7 grind for your entire team. Give your employees time to rest, and mean it! Flexible scheduling, PTO encouragement, and location freedom (on site, hybrid, or remote) all signal that you care about them as people, not just output machines. And you won’t be alone. In their most recent collaborative report, Bowman Williams and ninjaOne, found that nearly 3 of 4 MSP hiring placements were hybrid or fully remote.
But don’t just tell them it’s a priority–show them. Employees are less likely to submit vacation time, or even request an extended lunch break for an appointment, if they see you never take that time (or prioritize your life outside of work) yourself.
How Helpt and Empath Can Support Your Growth Mindset
If you’re struggling to upskill existing staff, retain skilled staff, or bring in new skilled staff, you aren’t alone. Those hurdles came in 2nd, 5th, and 8th place for MSPs when surveyed by N-able. That, on top of growing as a leader yourself, is a lot! Consider partnering with Empath. Their website is chock full of resources made just for you. From free guides to their all-encompassing learning platform, Empath exists to help you lead with more confidence and clarity…and build the kind of company people want to be part of.
Need some time back to focus on that ongoing training and relationship building? Whether you want after-hours calls covered to increase your team’s work-life balance, Level 1 issues taken off your techs’ plates so they can attend virtual training more routinely, or need fully embedded help desk support so you can hire slower and smarter, we’re here to help.
All in all? Helping your employees grow doesn’t require a full HR department or a fancy leadership playbook. It just takes consistency, trust, and a real investment in their success.
Start small: host a meaningful 1:1, delegate something fully, or ask what your team wants to learn next. Growth will follow. As will retention.
Buy back your time to focus on what really matters.
About the Author
Alyssa Reed
Content Writer
After establishing her foundational skills as a content writer and marketing professional while working for small businesses and non-profits, Alyssa began working within the IT industry. Since then, she has specialized in crafting content for B2B marketing strategies for Managed Service Providers, as well as help desk and cybersecurity service providers. With a background in Journalism, she especially enjoys the social aspect that comes with being a writer. Whether it's interviewing a customer about a recent win for a case study or chatting with a coworker about their area of expertise for a slick sheet, it excites her that those stories can inspire action, add value, and increase trust.
In our latest podcast episode with Dean Trempelas, Head of MSP Success at Empath, he made a great point: when technicians (most likely) start their own Managed Service Provider (MSP) business, they are focused on being their own boss, providing top notch tech support, and taking care of businesses. What they don’t focus on? Being a people manager. They want the increased clientele but don’t anticipate the skills required to lead a growing team of people. Therefore, what Dean sees time and time again is an inability from leadership to help their own employees upskill. And what does not grow, grows stagnant.
MSP owners–your employees want more than a job. They want a path forward and a purpose behind their nine to five. They want to be proud of the work they do–instead of just feeling stuck in a dead-end job because they have bills to pay.
But how do you help them upskill, stay engaged, and build meaningful careers?
In this blog, we’ll walk through how to create that kind of environment, even when your days are packed and your team is pulled in ten different directions.
In this blog, you will learn:
Why growth and retention go hand in hand
10 practical ways to support your team’s development
How Helpt and Empath can support these goals
Why Having a Growth Mindset Positively Impacts Retention
It’s no secret: turnover is expensive and time-consuming. It also impacts office culture. When someone leaves, the knowledge goes with them. Morale can take a hit. Client relationships may suffer.
The best defense? A strong culture of internal growth.
When MSP employees feel like they’re growing, they are more likely to stay. They’re also more productive and engaged.
10 Practical Ways To Support Your Team’s Development
Build a Strong Foundation Through Onboarding and Training
Hiring is just the start. What happens after someone joins your team is what really sets them up for success. The worst thing that can happen for a new hire is, at day 30, 60, or 90, for them to realize…“Oh…this is the job? This is not what it seemed like at first…”
Invest time in onboarding. Set measurable goals and reasonable expectations. Offer training that is both technical and soft-skill-focused, especially for client-facing roles. The time you invest in this part of the process will save you time later down the road.
Let Go (a Little) and Delegate with Intention
Delegation is part of growth. If you are still holding onto every decision or redoing your team’s work, they will never feel trusted. Plus, you’ll burn out! Once you have trained someone well, let them run with it. Step in when needed, but resist the urge to hover. That trust helps people take ownership and pride in their work.
Practice Empathy for Their Bandwidth
Too often, leaders don’t realize what is on someone’s plate. Or if they do, they don’t know how much work behind the scenes has to happen to get it done. That is when resentment builds and performance drops. Instead, ask them:
“What are your top priorities this week?”
“Are there roadblocks I can help remove?”
“Does anything need to shift?”
This will help your team feel seen, understood, and appreciated, as well as help you prioritize routine tasks alongside ongoing projects.
Match Your Management Style to Their Needs
Not every employee needs the same level of oversight. Some folks love regular check-ins and structure. Others want more autonomy. Ask your team members what works for them, and adjust accordingly. A quarterly 1:1 might be perfect for one person, while another thrives with weekly touchpoints. Adapting to their needs shows them you care more about their success than your own preferences or natural inclinations.
Provide Employees With Mentors Who Aren’t Their Manager
It’s one thing to have a supportive boss. It’s another thing to have someone else you can go to for advice and encouragement. Assigning mentors from other parts of the company helps employees gain new perspectives and build connections outside their direct chain of command. It also makes it easier for them to ask questions they might hesitate to bring up with their manager.
Celebrate Progress, Not Just Results
Sometimes the biggest motivator is knowing someone noticed. Tell your team when they have done something well. Be specific. Did they handle a tricky client call like a pro? Meet a tight deadline? Help a teammate? It doesn’t take long, can brighten their day, and motivates them to continue doing well in the future.
Create Feedback Loops That Go Both Ways
Performance reviews should not be:
A surprise
Sporadic
A one-way street
Ask your employees: “What’s working?” “What is getting in your way?” “What do you need from me to succeed?” Build these conversations into your process. And show that you, too, are open to feedback (and willing to act on it)!
Support Their Goals with Time, Money, and Structure
Your employees may have aspirations beyond their current role. Ask what those are, and help them get there. That could look like:
Time set aside during their 8-hour shift for training or certifications
Professional development funds
Flexible time for job shadowing or involvement in new projects
Clearly defined paths to promotion or specialization
The more you invest in them, the more likely they are to invest in your business.
You know what else this means? You should be continually investing in yourself too. Prioritize the ongoing betterment of your people management skills, not just your cybersecurity or AI knowledge.
Encourage Cross-training Through “Lunch and Learn” Sessions
Not every training has to be formal or time-consuming. One of the easiest ways to upskill your team and spark curiosity is to host these casual sessions. These can be led by anyone at your company, whether that’s someone in tech support or a marketing specialist, or even a guest speaker that pertains to your industry. It encourages your team to teach each other through knowledge-sharing, builds confidence, and helps your employees see the bigger picture of how your MSP runs.
Model the Work-Life Balance You Want for Them
Having a business that requires 24-hour answering services does not have to mean a 24x7 grind for your entire team. Give your employees time to rest, and mean it! Flexible scheduling, PTO encouragement, and location freedom (on site, hybrid, or remote) all signal that you care about them as people, not just output machines. And you won’t be alone. In their most recent collaborative report, Bowman Williams and ninjaOne, found that nearly 3 of 4 MSP hiring placements were hybrid or fully remote.
But don’t just tell them it’s a priority–show them. Employees are less likely to submit vacation time, or even request an extended lunch break for an appointment, if they see you never take that time (or prioritize your life outside of work) yourself.
How Helpt and Empath Can Support Your Growth Mindset
If you’re struggling to upskill existing staff, retain skilled staff, or bring in new skilled staff, you aren’t alone. Those hurdles came in 2nd, 5th, and 8th place for MSPs when surveyed by N-able. That, on top of growing as a leader yourself, is a lot! Consider partnering with Empath. Their website is chock full of resources made just for you. From free guides to their all-encompassing learning platform, Empath exists to help you lead with more confidence and clarity…and build the kind of company people want to be part of.
Need some time back to focus on that ongoing training and relationship building? Whether you want after-hours calls covered to increase your team’s work-life balance, Level 1 issues taken off your techs’ plates so they can attend virtual training more routinely, or need fully embedded help desk support so you can hire slower and smarter, we’re here to help.
All in all? Helping your employees grow doesn’t require a full HR department or a fancy leadership playbook. It just takes consistency, trust, and a real investment in their success.
Start small: host a meaningful 1:1, delegate something fully, or ask what your team wants to learn next. Growth will follow. As will retention.
Buy back your time to focus on what really matters.
About the Author
Alyssa Reed
Content Writer
After establishing her foundational skills as a content writer and marketing professional while working for small businesses and non-profits, Alyssa began working within the IT industry. Since then, she has specialized in crafting content for B2B marketing strategies for Managed Service Providers, as well as help desk and cybersecurity service providers. With a background in Journalism, she especially enjoys the social aspect that comes with being a writer. Whether it's interviewing a customer about a recent win for a case study or chatting with a coworker about their area of expertise for a slick sheet, it excites her that those stories can inspire action, add value, and increase trust.
Stop Answering Calls.
Start Driving Growth.
Let Helpt's US-based technicians handle your support calls 24x7 while your team focuses on what matters most.
Stop Answering Calls.
Start Driving Growth.
Let Helpt's US-based technicians handle your support calls 24x7 while your team focuses on what matters most.
Stop Answering Calls.
Start Driving Growth.
Let Helpt's US-based technicians handle your support calls 24x7 while your team focuses on what matters most.
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