Training as a Strategic Investment with Nathan Gemmill
I am Jeni Clift. Over the past 30 years Nick and I have built and scaled Australian managed service providers and learnt the hard lessons that most owners only discover through pain. One of the recurring pressures we see is finding and keeping the right people. If you are an MSP owner or service manager and you are frustrated by recruitment shortages, high contractor churn, or the constant scramble to train new starters, this episode of MSP Mastery: Ctrl Alt Deliver will feel very familiar. In this episode we talk with Nathan Gemmill, someone we first met when he walked into our office straight out of high school. Nathan is a perfect example of a career built by doing the work, not by a university certificate alone. His story reinforces the frameworks Nick and I have used for decades: invest in trainees, design deliberate training pathways, build psychological safety, and think long term about talent as part of your product.
MSP Mastery
5/21/20265 min read
Jeni and Nick perspective
Nick and I have always treated recruitment as a strategic activity rather than a stop gap. Good people do two things. They solve customer problems and they convey your business values to clients in every interaction. If you want scale and predictable service quality you cannot outsource your culture to a payroll agency. You have to grow it inside your business.
From our experience the most reliable way to do that is to bring people in at a junior level and teach them your way of working. That is the trade off. You accept a temporary slowdown in productivity in exchange for building a cohort of staff who think like you, escalate like you, and deliver like you.
Nathan’s path in this episode proves the point. He arrived keen, curious, and green. Over a three year traineeship he absorbed everything from customer conversations to operational tooling. He then returned to the business with more maturity and remained engaged because the model allowed him to grow inside the organisation rather than being parachuted into an alien culture.
Why it worked is simple. The business invested time and structure into his development. They created defined stages, expectations, and a clear conversion point from trainee into ongoing team member. The take away for MSP owners is to budget for the slow first months and build a two year approach that treats traineeship as a pipeline not a temporary experiment.
Structure training so learning is inevitable
Jeni and Nick perspective
We have seen traineeships succeed when training stops being optional and becomes scheduled work. Many MSPs rely on self paced learning and hope people will complete it around billable work. That rarely happens. If you want capability to scale you must protect learning time and make training non negotiable.
Nathan described how the first months overwhelmed him. Coming from a school routine into a nine hour work day was exhausting. He suggests protected learning days and a buddy mentor as being the things that would have smoothed the transition. From our vantage point that is precisely the operational fix. Book one day a month for structured training. Pair every junior with a named mentor who is explicitly responsible for their development. Make certification milestones part of the employment agreement.
Nathan’s evidence is practical. His success came from having a buddy he could go to whenever he had questions and from progressively more challenging responsibilities. The analysis is straightforward. People learn faster when material is sequenced, when there is safe time to practise, and when there is someone to translate theory into day to day practice. If you want to fast track capability, stop asking staff to learn around their tickets and instead design learning into the workweek.
Build a culture where mistakes become learning
Jeni and Nick perspective
A service business is an experiment with risk. Things will go wrong. How your business responds to mistakes defines whether people will grow or hide. We have always emphasised psychological safety as a critical lever for operational maturity. Teams that can own issues early and communicate clearly recover faster and keep customers calm.
This episode contains the clearest example. Nathan tells the story of clicking the wrong button on a backup system and the immediate sickening realisation when outages began. Crucially Nathan did what we advise every team to do. He owned the mistake, stopped hiding, and leaned on senior colleagues. The managers handled customer communication while the technical team executed the fix.
Why that approach works is also clear. Panic and secrecy multiply harm. Truth and a plan concentrate the team on solving the problem. It also produces durable lessons because the corrective process becomes training for the whole team rather than a private embarrassment. For MSP owners the practical implication is to bake incident playbooks, clear escalation paths, and coaching for public acknowledgement into your culture. Reward candour. Teach how to communicate under pressure. That is how you turn a mistake into an advantage.
Career pathways and the internal versus external trade off
Jeni and Nick perspective
One of the dilemmas we often see is where senior people go next. Some technologists prefer breadth and client variety. Others want depth and the chance to polish systems to a high degree. As owners you must design pathways for both or be prepared to lose talent.
Nathan explains why he transitioned from the MSP world into an internal IT function. DWM gave him incredible breadth. He could touch many technologies and many businesses. In an internal role he found the chance to go deeper and refine a single environment until it shone. From our perspective that choice is normal and healthy. It is not failure. It is career development.
The lesson for MSPs is to offer parallel career ladders. Give people the opportunity to become a service delivery lead with wider client exposure or a senior engineer who owns a specific technology stack. Use rotations, secondments, and the chance to work on internal projects to retain people who might otherwise leave for more focused roles. Nathan’s move away from the MSP scene was mitigated by keeping a toe in the industry through side projects and listening to the podcast. That is a pattern we endorse. Keep alumni networks active and offer part time or advisory roles so experienced people can remain connected.
Hero moment and the lesson beneath the panic
Jeni and Nick perspective
If you listen to this episode you will feel the heart drop when Nathan realises the consequence of a single click. That is the hero moment. It is not heroic because of technological skill. It is heroic because of response. He owned it. The managers rallied. The team communicated with customers. The incident became the foundation for better processes and a stronger culture.
We break down why this moment matters. First it reveals the value of a culture that encourages ownership. Second it highlights the operational separation you must maintain between customer communication and technical recovery. Third it shows the long term value of investing in training early so juniors have the judgement to escalate fast.
For MSP owners the direct actions are to rehearse incident response, make customer facing messaging templates, and remove the stigma from mistakes. Use these events as case studies in your academy so every team member learns from the real world.
Conclusion
Over the past 30 years Nick and I have seen the same patterns repeat. Hiring trainees is not a charity. It is a growth lever. The companies that commit to structured training, buddy mentorship, and a culture that treats mistakes as learning outperform those that chase immediate billable headcount. Nathan Gemmill’s story in this episode of MSP Mastery: Ctrl Alt Deliver is a practical validation of those lessons. He shows that curiosity matters, that structured training accelerates capability, and that owning mistakes builds resilience.
If this resonates with you and you want to design a traineeship, an academy day, or an incident playbook we would love to help. Reach out to Nick, me, and the MSP Mastery team. Reflect on the gap between where your people are and where you need them to be, then take one concrete step this month. Whether that is booking a monthly training day, assigning a buddy mentor, or running a single incident tabletop the small choices you make now compound into the culture and capability your business will live with for years. Join the conversation at MSP Mastery and let us help you build an MSP that actually works for you.
