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5 Takeaways from 100+ Conversations with MSPs about HaloPSA

Apologies for my radio silence lately, folks! If you thought I’d been abducted by aliens or joined a secret society of IT wizards, well, I hate to burst your bubble but the truth is a tad less dramatic. I’ve been on a 6-month odyssey of HaloPSA implementations for MSPs, thanks to a shiny new partnership my employer inked with Halo as an onboarding partner.

During this time, I’ve had the pleasure, and sometimes the perplexity, of chatting with over 100 MSPs about HaloPSA implementation. Conversations ranged from the enthusiastic (think kid-in-a-candy-store level excitement), to the skeptical (“I read your blog and thought you’d be meaner”), to the downright bewildered (“Wait, you mean I can automate that?”).

Throughout this journey, I’ve donned the mantle of the ‘implementation maestro’, guiding scores of MSPs through the intricate dance of HaloPSA setup. I’ve earned the affectionate moniker of the ‘Halo Whisperer’ – I can practically hear the hum of t-shirt presses churning out my unofficial title.

Throughout this whirlwind journey of continuous learning, teaching, and forming wonderful friendships, I’ve become intimately acquainted with the struggles MSPs grapple with. These challenges often lead them towards the respite of HaloPSA, or into the labyrinth of attempting self-implementation. Yet, what truly astounds me, is the uncanny similarity in the missteps many MSPs make. It’s almost like a tragic symphony, unfolding in the same discordant notes of implementation misfires.

Observation #1: Many MSPs who try to implement HaloPSA without help either fail outright or fail to implement to the full potential of the product.

I was this fucking guy, by the way. When I started down my HaloPSA journey years ago I was too stubborn to purchase their Professional Services until I failed to implement and needed the help. An alarmingly high number of MSPs I speak with are in the exact same boat. Well over 50% of MSPs seeking our professional services are already using HaloPSA in production yet they were seeking external help to either complete the implementation or reconfigure the system.

The Unavoidable Need for Expertise

In my experience, implementing HaloPSA is no trivial task. It requires a deep understanding of the system, a solid grasp of IT Operations (both front and back of house), and the ability to think in the context of processes. Not to mention, the patience to troubleshoot when things don’t go as planned.

Here’s the glaring truth: HaloPSA, while a powerful tool, is not the sort of software you can simply buy and expect it to work flawlessly out of the box. It demands expertise and a fuckton of hard work to implement.

“Well over 50% of MSPs seeking our professional services are already using HaloPSA in production and seeking assistance in finishing deployment or reconfiguring.”

Here’s what we’ve learned: it’s not about admitting defeat, but rather recognizing that the path to successful HaloPSA implementation is often paved with the guidance of experts. These professional services aren’t just a safety net; they’re an invaluable resource to help you navigate the intricacies of HaloPSA.

So, let’s leave the stubbornness at the door. Open up to the idea of seeking help before the complexities of HaloPSA leave you feeling overwhelmed. After all, there’s no shame in asking for directions, especially when you’re navigating through uncharted IT territory.

A Complex Conundrum: The Invoicing Enigma

Now, let’s talk about invoices. Yes, finance shit. The actual worst thing about being in business. Implementing invoicing in HaloPSA is a labyrinth, a riddle wrapped in a mystery inside an enigma. And why wouldn’t it be? It’s a complex process riddled with variables and dependencies. This is exactly where you can fuck yourself if you don’t know what you’re doing because the output of invoicing is dependent on the correctly configured input of everything else in the system. If you don’t explicitly understand the interactions of the mechanisms that synthesize invoices every month, you will never be able to figure it out on your own.

“Invoicing isn’t just about sending bills. It’s a sanity check on your entire configuration and implementation of the rest of the modules and systems. In HaloPSA invoicing is an art.”

It’s quite simple, really. You need to understand what you don’t know. I know, it sounds like some philosophical musing, but bear with me for a second.

  • Do you know when to use Billing Plan Combinations instead of Contracts and the benefits of each?
  • Is your invoicing completely or almost completely automated?
  • Does all the information necessary from all your vendors synthesize to the invoice automatically, accurately, and without error or intervention every month?
  • Do you understand how HaloPSA links your tickets, time entries, and charge rates to your invoices?
  • Does your monthly invoicing take less than 30 minutes?

If your answer to any of these questions is ‘No,’ then it’s time to admit that you might need a little help. And that’s perfectly fine. Remember, every expert was once a beginner. And every person needs guidance sometimes. If you’re struggling with HaloPSA invoicing, don’t hesitate to ask for help. There is a thriving discord and reddit community to support you. Alternatively, engage with one of the Halo Onboarding Partners for help. These guys know their shit.

Observation #2: People have unrealistic expectations of Halo support.

From my countless dialogues with MSPs, I’ve noticed a common thread amongst the ones who have interacted with Halo support staff. They tend to tell me that support is “slow to respond” or “doesn’t understand what we need.” These are usually the same folks who say Halo can’t do what they need, so they can’t use it until it does.

Time Zones and European Holidays

Ever heard that the early bird gets the worm? Well, what if the worm’s alarm clock is set to Greenwich Mean Time and the bird is just trying to enjoy its morning coffee in the States?

Enter the interesting dynamic we’ve got going on here. HaloPSA, the dependable backbone of our MSP operations, is proudly UK-based. That’s good news for our friends across the pond, but for those of us who WON THE WAR, it can be enraging to the point of, say, tossing some tea into some unsuspecting harbor…

Scene: Your office, 3 PM. You hit a snag with HaloPSA. You shoot off a support ticket. You wait… and wait. Meanwhile, in the UK, it’s 8 PM. The Halo team is tucked into bed, dreaming in code and automation scripts. They’re not ignoring you, promise. They’re just recharging for another day of IT wizardry.

And let’s not even get started on holidays. Europeans seem to have a knack for squeezing in a few more than we do over here in the Land of the Free.

  • Easter Monday? Check.
  • May Day? Check.
  • Spring Bank Holiday? Check.
  • Summer Bank Holiday? Check.
  • Boxing Day? Check.

Just when you’ve gotten used to the timing, along comes another holiday, and our support line goes quiet. Don’t worry, they’re not on a permanent tea break; they’re just celebrating St. Swithin’s Day or some other obscure holiday we’ve never heard of.

So, while it may seem like our friends at Halo are working on “British Time,” they’re actually just working on ensuring they’re providing the best possible service. And hey, we can’t blame them for taking a few more holidays. They need them after being pummeled with our bullshit questions all day.

Your impatience or your shitty processes are almost certainly the problem

Let’s be real: we all have those moments when we want to point fingers at a tool or an external factor when things don’t go as planned. One of the most common things I hear about Halo support or implementation is that they “don’t get it” or “don’t understand how my business process works.” Consider this:

It is not their job to understand why you bill in an insane way and implement it for you:

“For every brother or sister your user has, that’s an extra $20 on their monthly bill.”

  • John, the only child? He’ll cost a straightforward $40 per month.
  • Samantha, blessed with two loving sisters? Well, Samantha’s account will set you back a cool $80 per month.
  • And what about the Brady Bunch scenario? Strap in, because that’s going to run you a whopping $200 every month!

Utterly preposterous, I know. The important point here is that I’ve heard some WHACK billing methodologies throughout these interactions and Halo cannot do actual magic. Close, but Tim didn’t pass his last exam at Hogwarts.

Your processes are actual garbage or you want Halo to work exactly the same AutoTask or ConnectWise:

Let’s rip off the band-aid. I’ve heard it all too often: “Our processes are garbage,” or “We want everything to work just like it did in AutoTask or ConnectWise.” This mentality is not only a roadblock but can also lead to missed opportunities.

First, let me clarify: “garbage” processes are typically just processes that haven’t been optimized. They’re not useless; they’re waiting to be refined. With the right tools and mindset, these so-called “garbage” processes can become streamlined operations that boost your productivity and bottom line.

As for wanting HaloPSA to function exactly like AutoTask or ConnectWise, I get it. It’s human nature to resist change. However, doing things “the way they’ve always been done” can stifle innovation. HaloPSA was designed to break new ground in IT service management, so let’s use it to its full potential.

Observation #3: Everyone always asks me what RMM I recommend to integrate with Halo.

It’s an interesting observation that everyone seems to be in a constant quest for the “perfect” Remote Monitoring and Management (RMM) tool to pair with HaloPSA. In my honest opinion, there isn’t a flawless option, but there are certainly a few that stand out from the rest.

NinjaRMM, for instance, stands out as the least bad choice amongst its peers. This might seem like faint praise, but let’s look at this realistically.

Every RMM solution has its own set of quirks and hurdles, but NinjaRMM, in my experience, tends to be the least problematic.

  • For starters, it’s quite user-friendly with a clean and intuitive interface, which is a breath of fresh air in an industry where clunky designs are unfortunately the norm.
  • Secondly, NinjaRMM’s integration with HaloPSA is relatively smooth and seamless, sparing you a lot of headaches down the road.
  • Lastly, their customer support is generally responsive and helpful, which is vital when you inevitably hit a bump in the road.

So while it may not be perfect, NinjaRMM is a solid choice that might just save you some sweat, and a few unexpected surprises along the way.

Bonus Opinion: Microsoft appears to be positioning Intune to eventually kill 3rd party RMM and that is a good thing

Shining a spotlight on the often-overlooked world of Remote Monitoring and Management (RMM) systems, it’s crucial to recognize the escalating role they play in the security landscape. The rampant advent of AI-augmented malware attacks presents a formidable challenge for third-party RMM systems. A seemingly innocuous tool for IT professionals, RMM systems have become a tantalizing target for nefarious actors.

Why, you ask? Simple. RMMs are the golden keys to the IT kingdom. They offer unfettered access to multiple networks, servers, and devices, making them a lucrative exploit for any self-respecting cybercriminal. A compromised RMM doesn’t just mean a security incident; it’s the digital equivalent of a Pandora’s box.

Third-party RMMs, while offering a range of functions and features, are increasingly becoming the Achilles’ heel in a company’s security armor.

So, what’s the solution? Enter Microsoft Intune. As the vendor of the most widely used operating system in the world, Microsoft is uniquely positioned to offer a robust and secure RMM solution. The integration between the operating system and the RMM could be seamless, reducing the attack surface and thereby mitigating the risk of exploitation.

  • Security: Microsoft’s industry-leading security measures and protocols would be natively integrated into the RMM, offering unrivaled protection from AI-augmented malware delivery.
  • Control: With a direct hand in both the OS and the RMM, Microsoft can ensure better control and swift patching of vulnerabilities, which is often not the case with third-party RMM providers.
  • Innovation: Microsoft’s vast resources and cutting-edge tech could lead to innovative features and capabilities in Intune that may be beyond the reach of many third-party RMM vendors.

In conclusion, the move by Microsoft to position Intune as a replacement for third-party RMMs isn’t just a strategic business decision. It’s a potential game-changer in the ongoing battle for cybersecurity. In the face of evolving threats, it’s the kind of bold, forward-thinking move that the industry needs.

Observation #4: It’s a terrible idea to migrate your legacy ticket data into your new PSA

I can’t stress this enough: migrating your legacy ticket data into your new PSA system is akin to moving into a sleek, modern condo and insisting on bringing all the worn-out furniture from your grandma’s attic. Sure, in theory, it seems like a good idea. After all, who wouldn’t want all their history right at their fingertips?

But here’s the reality check: it’s a logistical nightmare that seldom provides the value you might expect. Let me tell you why.

  1. Complicated Migration: The process of migrating legacy ticket data into a new PSA system is complex, often fraught with technical issues and inconsistencies. It’s not as simple as a copy-paste operation. You’re dealing with different data structures, formatting, and systems that don’t always play nice together.
  2. Time and Effort: Even if the technical hurdles were not an issue, consider the time and effort required to validate and clean up old data. It’s a giant time-sink with a questionable return on investment.
  3. Relevance: The majority of legacy tickets are not relevant to your current operations. They’re ghosts of issues past, unlikely to recur or offer any significant insight into your present business processes.
  4. Unchain Your Processes: Think of it as breaking free from the chains of your old processes, stepping into a world of new possibilities where the only limitation is your own imagination. You’re writing the script now, and the story can be as innovative and efficient as you want it to be.
  5. You Can Still Archive It: You can always just archive that historical data in a way that is searchable. There are even low-code or no-code solutions for archiving data for later search. It doesn’t need to live inside Halo.

A Fresh Start: The Unseen Benefits of Leaving Legacy Ticket Data Behind

So, what’s the alternative, you ask? Wipe the slate clean. Start fresh. Use this as an opportunity to set up your new PSA system with a clean, well-organized database, free of redundant or obsolete information.

When you drop the baggage of legacy ticket data, the picture suddenly becomes clearer. You’re no longer viewing your PSA through the murky lens of outdated issues and irrelevant data. Instead, you’re presented with a clean, uncluttered canvas – an opportunity to rework your processes from the ground up, without being tethered to the past.

It’s like walking into a freshly cleaned room, where every item has been meticulously organized and every speck of dust wiped away. There’s a sense of clarity and possibility that’s simply not achievable when you’re knee-deep in old ticket data.

Remember, the goal here is to improve efficiency and streamline your processes, not to create a digital museum of every IT issue you’ve ever handled. Sure, there might be a moment of nostalgia as you bid farewell to that stubborn printer issue from 2003, but trust me, your future self will thank you.

Observation #5: Many MSPs are struggling with hardware procurement processes.

Imagine being an MSP, traversing the treacherous landscape of hardware procurement. You’re up against a chessboard of intricate details, ever-changing market prices, and a daunting list of distributors and vendors to partner with. Trust me, I’ve been there, and it’s a battle many of us wage.

Take, for example, an MSP I had the privilege of assisting. They found themselves ensnared in the convoluted intricacies of hardware procurement, struggling to streamline their operations. The ensuing inefficiencies were not just aggravating, but also expensive, threatening the quality of their service delivery:

“We’re an IT company, not a logistics company,” the exasperated CEO confided in me. “Our focus should be on delivering top-notch IT services, not sweating over hardware quotes and orders. It’s sapping our resources, and pulling us away from what we do best.”

His frustration was almost tangible, a sentiment I’ve encountered in numerous MSP conversations. This isn’t an isolated issue, but a deep-seated concern prevalent in our industry.

So, you’re likely musing, what’s the way out? How can MSPs traverse this intricate procurement maze without losing sight of their core mission?

The answer is not buying direct from Dell, HP, Lenovo, etc

Here lies a commonly held misconception among Managed Service Providers (MSPs); the idea that buying direct from big-name vendors like Dell or HP will yield the best bang for their buck. In reality, this isn’t usually the case.

Vendor pricing is often on par with, if not more expensive than, distributor pricing from places like Ingram Micro or D&H Distributing.

Why, you ask? Well, it seems counterintuitive, but the explanation is quite simple.

  • Volume: Distributors buy in bulk, allowing them to demand better pricing.
  • Relationships: Distributors have long-standing relationships with vendors, which can translate to preferential pricing.
  • Competition: Distributors are in constant competition with each other, driving them to offer competitive prices.

So, before you reach out to Dell or HP directly, consider giving distributors a chance. You may be pleasantly surprised by the potential savings and how much easier it is to work with them. As a bonus, D&H or Ingram won’t try to steal your customers behind your back. Dell 150% will.

Many MSPs expect their distributors to quote for them and that isn’t realistic in 2023

It’s a trend I’ve witnessed and time time again – MSPs relying heavily on their distributors to generate quotes. It’s almost as if they’re leaning on an outdated crutch, nostalgic for a time when the IT landscape was simpler, and hands-on effort was minimal. But let me be clear: this is no longer realistic in 2023. People who are highly technically competent do not work for distributors, and working as a sales rep on commission is not a job of the future for this industry.

We’re in a brave new world of IT automation, where MSPs must step up, take charge, and actively participate in the quoting process. The era of relying on distributors to do the heavy lifting has faded into obsolescence. The onus is now on MSPs to evolve, adapt, and thrive amidst this shift.

But fear not, for change, as intimidating as it may seem, often ushers in new opportunities and efficiencies. Here, I’ll share some of the strategies I’ve seen successful MSPs employ to take control of their quoting process, and in doing so, elevate their service delivery:

  • Firstly, invest in automation tools: The right tools can streamline your quoting process, eliminating manual tasks and freeing up your team to focus on high-value activities. HaloPSA, for instance, offers robust quoting functionality that can significantly reduce the time spent generating quotes, it just lacks real time pricing and availability with electronic ordering (a problem my employer will hopefully be solving later this year with an integration)
  • Secondly, foster relationships with distributors: Building strong relationships with your distributors can provide valuable insight into their pricing structures, allowing you to better negotiate and strategize your quotes.
  • Lastly, train your team: Whether it’s learning the intricacies of a new automation tool or understanding the nuances of vendor pricing, make sure your team has the knowledge they need to effectively manage the quoting process. Understanding how to register deals and getting authorized with vendors through distribution is a little time consuming, but pays massive dividends.

For smaller MSPs or those selling less than $1M in hardware per year, engaging with a VAR or Master MSP is probably the play

It’s a fierce digital jungle out there, especially for smaller MSPs. The competition is daunting, the technology ever-evolving, and the need for new hardware pressing. Allies are crucial in such a landscape, and this is where Value-Added Resellers (VARs) or Master MSPs come into play.

Picture Master MSPs as the undisputed champions in the grand arena of IT services. They stride onto the battlefield, armed with an arsenal of industry wisdom, formidable experience, and strong alliances with elite vendors, poised to land a decisive victory. And those featherweight contenders in the world of MSPs? They’re on the sidelines, basking in the glow of these titanic champions, reaping the rewards of their monumental strength.

Vendor partnerships are a prime example. For smaller MSPs, hitting dollar spend minimums with vendors to maintain a partner status is often an uphill battle. But that’s where Master MSPs come to the rescue.

When you partner with a VAR or Master MSP, you’re no longer a small fish in a big IT pond. Instead, you’re part of a bigger entity, one that suddenly has access to resources and benefits that would otherwise be out of reach.

Remember, the strength of the wolf is the pack. And in the IT services industry, the strength of the small MSP is their partnership with a Master MSP.

Master MSPs have already navigated the potholes you’re trying to avoid. Their established hardware experience can expedite your journey, helping you to compete effectively with bigger players. They’ve sweated the small stuff so that you don’t have to. It’s a game-changer that helps you level the playing field and compete effectively with industry giants.


In the grand scheme of things, I’ve learned that HaloPSA implementations aren’t just technical procedures. They’re intricate dances, steps choreographed to the rhythm of IT operations, processes, and automation. It’s a performance that demands sweat, scripts, and the occasional surprise.

Over a hundred conversations with Managed Service Providers and countless deployments of HaloPSA later, I’ve amassed a treasure chest of lessons. These aren’t just theoretical musings from a distant observer. They are birthed from the frontlines, drenched in practicality, and often accompanied by a dash of humor.

The journey is not without its pitfalls, but the insight gleaned is worth its weight in gold. Whether you’re an MSP navigating HaloPSA’s complexities or an IT professional seeking a broader industry perspective, I hope these lessons light your path.

Let these insights inspire your next strategic move. Or better yet, let them help you sidestep the hurdles I’ve stumbled upon. After all, who doesn’t appreciate a helping hand when braving new frontiers?

In conclusion, remember that every HaloPSA implementation, every MSP dialogue, is a story. And in these stories, you’ll find the seeds of wisdom, growth, and maybe – just maybe – a few chuckles along the way.

Until next time, happy automating!

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