Can you share an example of a time when you successfully mentored or trained another system administrator? What approach did you find effective?

Question

Unlock the full potential of effective mentorship in system administration with insights straight from seasoned professionals. This article distills their hard-earned wisdom into actionable tips for cultivating growth and expertise in the field. Benefit from the experiences of those who have expertly guided novices through the complexities of today's technological environments.

Paul DeMott · Answer

I recall working with a junior system administrator who was incredibly bright but lacked confidence in troubleshooting complex network issues. It was clear they had the raw skills, just not the experience in connecting the dots when things went wrong. To help them, I created a safe space where they could experiment without fear of making mistakes. I walked them through my thought process step by step, explaining why I was checking specific logs or running certain commands. This way, they could see how I approached problems and understand the reasoning behind each step.
One specific incident that stands out was when our email server was rejecting connections. I brought them in and had them drive the process. We started with the basics: checking if the server was up, pinging it, and verifying DNS settings. Then, we moved on to checking the mail server logs. I asked them to think about the next steps and why they thought they were necessary. If they were on the right track, I affirmed it and guided them forward. If not, I asked questions to help them see their mistake without feeling discouraged. This approach empowered them to figure out that a firewall rule was blocking the mail server's port. Afterward, they explained the problem and solution back to me, which really cemented their understanding and boosted their confidence.

Steve Payerle · Answer

Mentoring and training are core elements of my role as President of Next Level Technologies. In one instance, I worked closely with a junior system administrator to help them understand the intricacies of Microsoft Azure and the "365" ecosystem. I believe in hands-on learning, so I had them shadow me during a live project where these technologies were implemented for a healthcare client needing robust data security and seamless data access across their multiple locations.
This approach proved effective because it allowed them to see real-world applications of theoretical knowledge and understand the strategic decisions behind each step. I also emphasized the importance of troubleshooting under pressure by involving them in our disaster recovery plan for a real estate client, where prompt action was necessary due to a server failure. Walking through this process together underlined the importance of both technical expertise and client communication, which are pivotal in managing IT effectively.

Steve Fleurant · Answer

One of the most rewarding aspects of a career in system administration, beyond the technical challenges, is guiding the next generation. I recall a specific instance that solidified my belief in the power of effective mentorship. I was working with a junior admin, fresh out of a technical program, who was incredibly bright and eager to learn but visibly overwhelmed by the sheer scale of our infrastructure. Their initial training had covered the fundamentals, but the real-world application, with its layers of legacy systems and customized configurations, was proving to be a steep learning curve.
My approach centered around a concept that consists of breaking down complex systems into manageable, understandable chunks. Instead of overwhelming them with complete system diagrams, we started with a single, crucial application - our user authentication service. This implementation was a vital system, of course, but also one with relatively clear boundaries, making it an ideal starting point. We traced the entire process, from user login to database interaction to logging. We didn't just look at configuration files; we went deeper, questioning why each setting was configured the way it was.
The most crucial part of my mentorship was hands-on troubleshooting. We didn't wait for a major outage. I created minor, controlled issues - a misconfigured firewall rule, a simulated service failure - and had them walk through the diagnosis and resolution process. This demonstration wasn't about testing them; it was about building confidence. It was about showing them how to think like a system administrator, approach a problem methodically, and not just fix the issue but understand its root cause.
The real breakthrough came a few weeks later. A fundamental issue emerged - a minor but persistent authentication error affecting a subset of users. Using the techniques we'd practiced, the junior admin identified the root cause (a subtle discrepancy in a group policy) and proposed and implemented a fix, all with minimal guidance. It was less about that specific technical problem and more about their newfound independence and problem-solving ability. To me, it is key to equip those who are learning. That moment solidified the value of patient, practical mentoring - explaining not just what to do, but why, and empowering the learner to understand the underlying principles. This method allows them to apply this mindset and prepare for the next challenge.

Ryan Carter · Answer

When I mentored a system administrator during a complex cloud migration project, I focused on practical engagement and active problem-solving. We had a legacy-to-cloud transition that typically took months, but we aimed to complete it in weeks. We achieved this through collaborative sessions where I broke down each step of the migration process, ensuring they understood the nuances of cloud architecture.
I encouraged utilizing our Dynamic Matrices for vendor comparisons, a resource I helped develop to match technology needs with provider strengths swiftly. This accelerated their understanding of the selection process and empowered them to make informed decisions, trimming 30% off our expected costs. The process also equipped them to guide future projects with confidence.
My emphasis on an agnostic, unbiased approach to technology adoption proved pivotal. By tasking them with leading a part of the project under my supervision, they managed to swiftly implement a scalable SD-WAN and SASE network solution, aligning with strategic goals and improving response times by 40%. This experience highlighted the value of combining technical acumen with strategic oversight.

Karl Threadgold · Answer

I've found the most effective mentoring approach is creating a 'sandbox' NetSuite environment where trainees can experiment with ERP configurations without fear of breaking production systems. Last month, I worked closely with a junior admin using this method, and they went from being nervous about basic customizations to confidently implementing complex workflows for our Singapore clients in just eight weeks.

Shehar Yar · Answer

I once mentored a junior system administrator who was struggling with troubleshooting complex network issues. I started by pairing them with me during real-time system monitoring sessions, where I demonstrated my troubleshooting process step-by-step. I encouraged them to ask questions throughout the process and then gradually handed over more responsibility, allowing them to take the lead on resolving smaller issues while I provided guidance.
This hands-on approach, combined with follow-up sessions to review the challenges and lessons learned, proved highly effective. It not only built their confidence but also deepened their understanding of system intricacies. Ultimately, this method of blending real-world practice with reflective learning helped them quickly grow into a reliable and independent problem-solver.

Travis Willis · Answer

I trained a junior system administrator through hands-on instruction that covered server configuration, security standard implementation, and system troubleshooting methods during an essential system migration process. I provided direct assistance to my team members by allowing them to execute tasks under my immediate feedback. The process of breaking down complex information into basic steps made their learning more effective. System administrator check-ins were scheduled to allow staff members to ask questions as they gained confidence in their decisions. The documentation practices I promoted enabled trainees to retain their learned information and solve problems independently. The team members demonstrated substantial improvement in problem-solving abilities, which allowed them to work independently on similar tasks by project completion. The structured method of support led to remarkable success in advancing their career development.

Darin Garvey · Answer

As the owner of Basement Waterproofing Scientists, mentoring has been a key aspect of my role, especially in guiding new team members on our unique methods and mindset. For instance, I worked with a new technician who was struggling to identify leak sources effectively. I took him through live projects, showing him how to use our specialized leak detection equipment and interpret the data to plan targeted interventions. This hands-on coaching helped him become a more effective problem solver in the field.
Our team's commitment to client satisfaction is crucial, so I also emphasized building strong client relations by running role-plays and discussing past client cases where clear communication made a difference. We shared real testimonials about how this approach led to successful outcomes and reinforced trust. By instilling the importance of professionalism and knowledge, we've improved customer satisfaction and sealed our reputation for excellence.
In another instance, our projects often require quick and economical solutions. I mentored team members on assessing various waterproofing techniques such as sump pumps and subfloor pressure relief systems, guiding them to create a detailed strategy that balances cost with long-term effectiveness. This approach not only improved their decision-making skills but also ensured clients received the most suitable solutions for their problems.

Conrad Wang · Answer

The "You're the Teacher" Challenge is one of my favorite ways to mentor system administrators. I asked my trainee to document a key system process and then explain it to me as if I were a new hire. If they struggled to break it down clearly, it was a sign they needed a stronger understanding. This exercise strengthened their technical skills and improved our internal documentation. Seeing them gain confidence in both their knowledge and ability to explain complex ideas made it a valuable learning experience.

Dhari Alabdulhadi · Answer

Training and mentoring would nurture capable system administrators. I remember a time when I had to assist a new team member in transitioning to a system administration role. This person had a solid grounding in IT but needed to be taught specific administrative tasks and tools.
By using a hands-on approach and being as clear as possible with both communication and constructive feedback, I found this method most effective. The member's confidence and proficiency grew rapidly as a result of my step-by-step instructions and encouragement for active participation. Through regular check-ins with constructive feedback, they gradually refined their skill set. This process enhanced their technical prowess while also creating a good environment for teamwork.

Harmanjit Singh · Answer

When I mentored a junior system administrator transitioning from help desk support, I found a project-based approach most effective. Instead of abstract training, I assigned him ownership of migrating our client's website hosting infrastructure to a more robust solution.
My approach centered on three key elements. First, I created a safe environment for experimentation by setting up a parallel development environment where he could test configurations without fear of breaking production systems. This hands-on practice proved far more valuable than theoretical training.
Second, I implemented a structured documentation process. Rather than providing ready-made solutions, I encouraged him to document each challenge, attempted solutions, and final resolutions. This knowledge base became invaluable not just for his learning but for our entire team.
Finally, I established regular check-in sessions focused on guided problem-solving rather than direct instruction. When he encountered issues with server configurations, instead of providing answers, I'd ask questions that led him to discover solutions himself.
The results were remarkable. Within six months, he was independently managing complex system migrations and even identified efficiency improvements in our backup procedures that we implemented across all client systems. The experience reinforced my belief that practical ownership paired with supportive guidance creates more capable administrators than any formal training program.

Ryan T. Murphy · Answer

In my experience as the founder of UpfrontOps, effective mentorship for system administrators involves a hands-on, collaborative approach similar to the technical environments of sales and marketing operations. When integrating new CRM systems or AI tools, I often pair seasoned administrators with new team members. This peer mentorship not only accelerates learning but also reinforces best practices and data-backed insights.
For example, during a major SaaS integration, I spearheaded workshops that focused on real-world scenarios, allowing administrators to troubleshoot and optimize systems collaboratively. We used practice scenarios and gamified assessments to build confidence and expertise in using advanced CRM features. This method bolsters their problem-solving skills, making the transition seamless across diverse tech ecosystems.
Fostering a culture of continuous learning is key. I emphasize personalized training sessions customized to the admins' specific duties, from managing lead tracking to optimizing support tickets. This role-based training ensures that everyone is equipped with the most relevant skills and can effectively leverage AI predictive analytics, resulting in smoother operations and measurable business impact.

Emil Calangi · Answer

There was a time when my business was just starting, and I mentored a junior system administrator who had recently joined our team. He possessed the technical skills but struggled with the practical aspects of managing a live system. Instead of overwhelming him with manuals and procedures, I guided him through real situations we encountered daily. I allowed him to shadow me during critical tasks such as server maintenance, troubleshooting network issues, and setting up security protocols. Observing how things were handled in real-time gave him the confidence to take on tasks independently.
One approach that proved effective was letting him take the lead while I observed. If he made a mistake, I refrained from intervening immediately unless it was urgent. I allowed him to identify the issue and guided him toward a solution instead of simply providing the answer. Over time, he became more self-reliant and began troubleshooting problems without hesitation. I ensured he understood that asking questions was never discouraged and that learning from mistakes was an integral part of the process. He eventually became one of the go-to individuals on our team, and witnessing his growth made the time invested in mentoring him entirely worthwhile.

Adrian Iorga · Answer

After a junior system administrator handled their first major incident, we sat down for a debrief—not to dwell on mistakes, but to turn them into growth opportunities. I asked them to walk me through their thought process during the outage, highlighting what worked and where they hesitated.
Together, we identified gaps in troubleshooting, automation opportunities, and ways to improve response time. Instead of feeling discouraged, they left the conversation with a clearer strategy for future incidents.
This approach helped them build confidence while reinforcing a culture where mistakes weren't just tolerated but used as stepping stones for improvement. That mindset shift made them a far stronger admin in the long run.

Samuel Charmetant · Answer

To simulate real-world outages, I set up a "midnight pager test" where I would send a fake high-severity incident and observe how a trainee responded. The next morning, we would break down their approach step-by-step, focusing on what they did well and where they could improve.
This hands-on drill created a realistic but low-risk way to build confidence under pressure. It also helped them develop a structured response process instead of reacting on instinct alone.
The goal wasn't to catch mistakes—it was to prepare them for the reality of being on call. Seeing their troubleshooting skills sharpen with each test made it one of the most valuable training exercises I've used.

Jerry Han · Answer

When mentoring a new system administrator, I introduced the "Zero-Google" Challenge for handling critical tasks like restoring a failed RAID array. Instead of searching online for answers, they had to rely on built-in documentation, system logs, and their own troubleshooting instincts. This exercise forced them to truly understand how systems work rather than just following a step-by-step guide.
At first, it felt frustrating, but they quickly learned how to break problems down logically. Afterward, we reviewed their approach, discussing what worked, what didn't, and what they'd do differently next time.
The result? They became far more confident in their ability to troubleshoot complex issues under pressure, without relying on a search engine as a crutch.

Alex Cornici · Answer

I once had the opportunity to mentor a junior system administrator, Sarah, who was transitioning from a help desk role. She was enthusiastic but a bit overwhelmed by the scale of the network she needed to manage. My approach was hands-on and collaborative. We began with daily check-ins where I explained how different systems interacted and the common issues that might arise. Gradually, I involved her in planning our network upgrades, which really helped in boosting her confidence and understanding of complex network structures.
One effective strategy was assigning small but crucial tasks that played to her strengths, like managing backups and monitoring server performance. Soon, Sarah was not only managing these tasks independently but also suggesting improvements. It was rewarding to see her evolve from asking basic questions to leading a training session on network security best practices for her peers. The key, I found, was to create a supportive environment that encouraged asking questions, no matter how simple. This approach not only benefits the mentee but often provides fresh perspectives on routine tasks, reminding me to never overlook the basics. Ending on this note, it's clear that mentorship is a two-way street that can rejuvenate one's own approach to work while helping others grow.

Lev Peker · Answer

The "Reverse Troubleshooting" Drill was one of the most effective mentoring exercises I've used. Instead of asking my trainee to fix an active issue, I had them take a resolved incident and work backward from the solution to uncover the root cause.
This forced them to analyze logs, spot early warning signs, and understand why the issue happened in the first place. It strengthened their ability to think critically rather than just apply quick fixes. They became much more confident in diagnosing problems before they escalated. I was incredibly gratified to see how they would approach future incidents with a greater understanding.

Bill Mann · Answer

The person I trained had knowledge of TCP/IP, DNS, DHCP, firewalls, and most of what was necessary to be a systems administrator. They just didn't possess much cybersecurity experience. I created every real-world problem I could think of for them to solve and was there to help, but without giving away solutions. Walking them all the way through each problem would not cement solutions and protocols in their memory. I ran them through the gamut of security breaches, server outages, and performance problems. In addition, they enrolled in necessary certifications. By sharing my security knowledge in real-world scenarios, along with acquiring the necessary certifications, they were up to speed quickly and advanced their career.

Paul Sher · Answer

I discovered that pairing junior admins with real projects while maintaining an open-door policy worked wonders when I mentored our new system administrator last year at FuseBase. We'd tackle complex automation workflows together, and I'd guide them through the problem-solving process rather than just giving answers. This approach helped them grow from handling basic tasks to managing our entire CI/CD pipeline within six months.

Alan Chen · Answer

When onboarding a new system administrator, I focused on pairing real tasks with guided learning. Instead of overwhelming them with documentation, I walked them through live systems and explained why things were set up the way they were. One effective approach was letting them shadow during incident responses, then later handle similar issues with me as backup. This built confidence while reinforcing best practices in a real context. We also held short weekly debriefs to review what went well and what could improve. That balance of hands-on learning and consistent feedback helped them become fully independent in under two months.

Bram Louwers · Answer

I began by first understanding their strengths and areas for improvement. I used a hands-on approach, walking them through key systems and troubleshooting methods in real time. We worked together on projects, and I encouraged them to ask questions and solve problems independently, providing guidance as needed. I also set up regular feedback sessions to address challenges and track progress. This approach built their confidence, allowed them to grow at their own pace, and ultimately helped them become more self-sufficient and effective team members.

Kevin Baragona · Answer

I have found "Failure Friday" and "Safe Space for Making Mistakes" very effective in mentoring and training other system administrators. In this approach, every Friday, we would set aside a few hours to experiment with new technologies and configurations without the fear of breaking anything. For instance, I would ask them to delete a critical file or change permissions in the wrong way. This simulated real-life scenarios and allowed my mentee to learn how to handle unexpected issues without causing any actual damage.
In one instance, my mentee was able to troubleshoot and fix an unexpected server issue quickly during peak traffic hours because of the skills they learned through this exercise. They were praised by our team and gained more confidence in their abilities. This hands-on experience gave them confidence in handling real incidents without the pressure of affecting live environments. It also taught them to anticipate failure scenarios before they happened.

23 Tips for Effective System Administrator Mentorship from the Pros

Table of Contents

23 Tips for Effective System Administrator Mentorship from the Pros

Created Safe Space for Experimentation

Hands-On Learning with Real Projects

Breaking Down Complex Systems

Focused on Practical Engagement

Sandbox Environment for ERP Configurations

Real-Time System Monitoring Sessions

Hands-On Instruction During System Migration

Guided New Technician with Live Projects

Document and Explain Key System Processes

Hands-On Approach with Clear Communication

Project-Based Approach for Practical Learning

Hands-On Collaborative Approach

Guided Through Real Situations

Turned Mistakes into Growth Opportunities

Simulated Real-World Outages for Training

Zero-Google Challenge for Troubleshooting

Hands-On Collaborative Mentorship

Reverse Troubleshooting Drill

Real-World Cybersecurity Problem Solving

Open-Door Policy with Real Projects

Pairing Real Tasks with Guided Learning

Hands-On Approach with Regular Feedback

Failure Friday for Safe Experimentation

Up Next