Tales From the Trenches: Wisdom from the Frontlines of Managed Services

Adam Hannemann
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  • Entrepreneurship
  • Updated Weekly

The Managed Services space can be a challenging place to build a business. Tune in to hear industry experts talk about topics that are on the minds of MSPs in the Peer Groups. Our hosts come from working in the trenches at Managed Service Providers, and are active MSP Peer Group facilitators that have conversations with dozens of MSPs each month. Topics we will cover will include finance, pricing, sales, marketing, running the business, legal, and pretty much anything MSPs are talking about.

  1. Apr 23

    Skipping 1-on-1s Is Costing You More Time Than It Saves

    Join my newsletter here: https://adamhannemann.com/newsletter If you're telling yourself that chatting with your techs throughout the day counts as a 1-on-1, it doesn't, and this episode is going to make that uncomfortably clear. Natalie and I sit down for an honest conversation about how often MSP owners and service managers are actually meeting with their people one-on-one, and why most of us aren't doing it nearly enough. The short version of our take: more often, shorter, and let the employee lead. - What the spectrum of 1-on-1 frequency actually looks like across MSPs, from never to weekly, and what each of those really signals about your team culture - Why frequent short meetings beat infrequent long ones, and what a good 15 to 20 minute 1-on-1 should actually look like - The difference between a 1-on-1 and a status update, because this is about the person, not the tickets - How consistent 1-on-1s quietly solve your performance review problem by building a real-time record of how someone is doing across the whole year - The hidden cost of skipping them, including why owners who avoid 1-on-1s to save time often end up spending way more on retention and rehiring Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/ 👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    19 min

  2. Apr 16

    MSP Hiring Guide, Who, When, and How

    Join my newsletter her: https://adamhannemann.com/newsletter Hiring in an MSP sounds simple until you’re actually in the middle of it. In this episode, Natalie and I dig into one of the most common challenges we see in Peer Groups: knowing when to hire, who to hire, and how to do it without creating bigger problems for your business. This is one of those areas where a bad decision can set you back months, and a good one can unlock real growth. We talk through practical signals you can watch for, including financial readiness, utilization, and what your team actually looks like day to day. We also get into the realities of early-stage hiring, why your first hire matters more than you think, and how to avoid the trap of bringing on the wrong level of technician or role too early. If you’ve ever wondered whether it’s time to hire, struggled with figuring out the right position, or just want a more structured way to think about growing your team, this conversation will give you a clearer path forward without overcomplicating it. If you are looking for an MSP recruiter we'd both recommend reaching out to Troy Gelsky: https://www.linkedin.com/in/troy-gelsky-bb522b93/ Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/   👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    40 min

  3. Apr 3

    Routines for MSP Owners and Service Managers

    In this episode of Tales from the Trenches, Natalie and I dig into something that sounds simple but is often missing in MSPs: routines. We break down what a strong cadence actually looks like for both owners and service managers, and why so many businesses get stuck reacting to fires instead of running with intention. From daily dashboard reviews and sales discipline to weekly one-on-ones and client check-ins, we talk through the habits that keep things from slipping through the cracks and how easy it is to lose momentum when those habits aren’t in place. We also spend time on the bigger picture rhythms that tend to get ignored. Monthly financial reviews, tracking profitability, and making sure your key initiatives are actually moving forward are all critical. On the service side, we dive into ticket management, SLA performance, and capacity planning, along with how small misses today can turn into big problems next week. There’s a strong theme throughout the conversation around visibility, whether it’s into your numbers, your team, or your client experience. The big takeaway is that routines are not about restriction, they are about clarity and control. Without them, it becomes incredibly difficult to lead, make decisions, or scale effectively. We talk about building these habits early, refining them over time, and making sure you are not the bottleneck in your own business. If you’ve ever felt like your MSP is constantly reacting instead of operating with purpose, this is a conversation worth tuning into. Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/ 👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    24 min

  4. Jan 22

    MSP Account Management 101

    Account management is a key process and role in your MSP. In this episode Natalie and I talk about all things Account Management. Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ We even have an Account Manager Peer Group. Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/ 👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com   Looking for a Bookkeeper for your MSP? Check out https://nordicsky.us

    30 min

  5. 11/10/2025

    Let's Talk About Lead Generation and Finance

    Join my newsletter here: https://adamhannemann.com/newsletter Over the past week I've talked to a bunch of MSPs about Lead Generation and Finance. These topics come up a lot in my travels in the MSP Peer Groups. These two things are topics that few MSPs didn't get in the business to learn. Most MSPs start as techs that start a business didn't plan on becoming a sales person, a marketing person, and a financial wizard. The reality is that you need to get good enough at these things. This is what I'm talking about in today's Tales from the Trenches. Natalie is on PTO so I'm flying solo. This week's Tales from the Trenches is all about finance and lead generation. Here is my playlist on Lead Generation and Sales: https://www.youtube.com/playlist?list=PL4Oa0PmgihVt9vZaDAcDQkxxNKNvFdjDl Here is my playlist on MSP Finance: https://www.youtube.com/playlist?list=PL4Oa0PmgihVuDYdh5K84EHtJrj8ZlSjA3 Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/ 👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    19 min

  6. 11/07/2025

    It's Time to Raise Your MSP Rates

    Join my newsletter here: https://adamhannemann.com/newsletter Let’s be honest... raising prices is scary. Most MSPs avoid it because they don’t want to lose clients or rock the boat. But here’s the truth: nothing in your business is getting cheaper, and avoiding that hard conversation will quietly eat away at your margins. In this Tales from the Trenches episode, Natalie and I share how MSPs can raise prices the right way — from timing and communication to dealing with client pushback. We’ll talk about how to identify which clients are profitable, which ones aren’t, and why an annual price review should be part of your growth strategy. If you’ve ever wondered how to raise rates without losing your mind (or your clients), this one’s for you. Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/ 👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    31 min

  7. 10/21/2025

    Top 5 Processes to Make Projects Profitable

    Join my newsletter: https://adamhannemann.com/newsletter In this episode of Tales from the Trenches, Natalie Hell and I dig into one of the most overlooked (and under-profitable) parts of running an MSP: Projects. From scoping to pricing to client communication, projects can make or break your margins, and too often, they end up being loss leaders instead of profit drivers. We’ve both been deep in the trenches running project teams, and we’ve got some stories — and lessons — that every MSP owner or project manager should hear. We walk through the five biggest things we’d focus on if we were running an MSP project team today. Many of these lessons we learned the hard way in our former MSPs. We talk about what goes wrong when your scope isn’t tight, what happens when communication slips, and how your Statement of Work (SOW) can either protect your profitability or completely sink it. If you’ve ever wondered why your MSP projects aren’t hitting the margins you expect — or why clients get cranky halfway through a rollout — this is a conversation you’ll want to listen to all the way through. Because sometimes the difference between a successful project and a financial mess isn’t the tech… it’s the process. Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/ Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/ 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    33 min

  8. 09/30/2025

    If You Step Away, Does Your MSP Survive?

    In this episode, we're diving into a side of business continuity that often gets overlooked in the MSP space: What happens to your business if you, the owner, can’t be there. This isn’t about data backups or disaster recovery tools. Instead, it’s about building a plan so your MSP can keep running if you need to step away for a vacation, face an unexpected illness, or even in the worst-case scenario, if you’re no longer around to lead.   Interested in the Pax8 Peer Groups? You can find out more info here: https://www.pax8.com/en-us/academy/groups/   Interested in the Pax8 Instructor Led Training? You can find out more info here: http://pax8.com/en-us/academy/training/   👇 Like what you see? Don’t forget to: 📧 Join the MSP newsletter for tools, tips, and templates → https://adamhannemann.com/newsletter 🔔 Subscribe for weekly MSP insights → https://youtube.com/@Adam-Rambles 🌐 Learn more or connect with me at https://adamhannemann.com 🌐 Connect with Adam on LinkedIn: https://linkedin.com/in/ahannemann 🌐 Connect with Natalie on LinkedIn: https://www.linkedin.com/in/natalie-hell/

    29 min
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About

The Managed Services space can be a challenging place to build a business. Tune in to hear industry experts talk about topics that are on the minds of MSPs in the Peer Groups. Our hosts come from working in the trenches at Managed Service Providers, and are active MSP Peer Group facilitators that have conversations with dozens of MSPs each month. Topics we will cover will include finance, pricing, sales, marketing, running the business, legal, and pretty much anything MSPs are talking about.

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