By
Mendy Green
December 18, 2022
•
20 min read
Business
A Cloud Perspective
“Should my business be going to Cloud?”
This is one of the most popular questions that comes up in my conversations with clients, and like every other question I get, I like to answer it with “It depends”.
Before we can address this, we need to address the ongoing struggle between IT Professionals and Marketing Professionals. This was cleverly outlined in the classic Project Management meme
We won’t get too far into the specifics of this as Marketing can be a post all by itself, but suffice to say, the…let’s call it exuberance to sell something new, tends to make for overly aggressive messaging targeting the Stakeholders which does not generate tingly-friendly feelings on the people who actually have to implement, support, or answer questions about the technical specifics. This is true no matter if the “Expert” person is at your company or the company the marketing person is sitting at. If you need a further demonstration of what this looks like you can watch the skit on YouTube called “The Expert” which should give you an idea of what frame of mind to approach this question with
Keeping this in mind we need to immediately increase our level of skepticism when we hear about Cloud Computing (or really any new technology).
Let’s switch tracks for a moment. One of the things I always talk about is how there’s at least two sides to everything. Literally you can take a specific item, scenario, concept, etc. examine it and you’ll see two or more sides that reflect or are directly opposite to each other. In business finances for example we have Operating costs and Cost of Goods Sold (COGS). Traditionally Operating costs were made up of things like Rent for the office, Utilities, supplies and things like that. Supplies would include the cost of equipment (such as computers) Utilities would include cost of the internet and so on. COGS would be made up of how much money the business would need to spend, in order to provide the service that they offer. This is essentially two sides to the same thing (money being spent), but you track them separately because they help you break down the cost of running the business vs the cost of providing services.
In other words, Operating Expenses can be broken down to the point where you would assign a Per Dollar amount for each Employee that you have, and COGS would be broken down and assigned a Per Dollar amount for each Customer
Now let’s get back to the point of this. Cloud, like everything else, has 2 or more (way more actually) sides. There’s Infrastructure as a Service offerings, Platform as a Service, Software as a Service, and so on and so forth and all of these items get mixed up and placed into the “Cloud” category. If you dig into what Cloud actually is, you’ll find that it’s just…rented computers. Really. If you’re skeptical, you can read more on this here from one of the bigger software platforms on their reasons why they’re leaving the cloud.
The questions we’d want to answer so that we can determine if you should be moving to the cloud are as follows.
Would you be moving your Operating Expenses to the cloud or your COGS. Specifically, are you providing an online service to your clients that requires you to rapidly scale up if you were to grow, or that allows you to measure out the cost of running in the cloud against the number of users you’re servicing?
Running in almost any cloud has pricing that is broken down to the minute, generally speaking. This is one of the big things marketing likes to tout “Scale up or down as needed, so it’s very cost effective”. Cost effective compared to running them 24/7 sure, but not cost effective compared to buying hardware. Marketing is selling you on the idea that if you needed to turn down services, you can do rapidly and save money with it off, but if you never need to turn down services, and your scaling doesn’t happen rapidly, then you’re actually spending way more over the same period of time of hardware life. Up to 4 or 5 times the amount potentially.
Do you have a need either from a compliance standard or your own security policy for enhanced security, physical auditing, a requirement to be highly available or a guaranteed uptime of 4 or more 9s (99.99%)?
Here is where it starts making sense to consider, although the question of finding a datacenter that will rent you hardware or allow you to place hardware vs running in something like Google Cloud, Azure, or AWS is still debatable. In the end the level of redundancies that exist in the cloud or datacenter are harder to build (read, more costly) than using an infrastructure that is already built and essentially being shared. This isn’t a new phenomenon, if you’ve read my article on the MSP Business Fallacy, or even just paid attention in the world the idea of pooling resources to save on costs is a well-established and very successful pattern. This is something that can range on a spectrum from sharing power costs, to sharing full on hardware and running your services on segregated containerized workloads.
Are you concerned about control of your data. Specifically, does it matter to you if your data is physically on equipment that you solely own and control, or is your business okay with the data being placed onto equipment owned and controlled by a trusted Third Party
Data sovereignty is an important part of the equation, even if you do trust it to a third party, the question of which region and where it is physically located is still an issue. In the end the agreements you sign with vendors and clients state that the data you hold for them is your responsibility to protect and keep safe and you do not have the right to assign that responsibility to anyone else. These are all concerns that should be evaluated and addressed in your assessment of moving to cloud.
In the end there’s no real good right answer, as most of these questions are ones you’ll need to decide for your business. I’ve outlined a table below to help with the decision matrix, but it is still only just a suggestion.
I'm passionate about IT, driven by a dual love for solving complex problems and a commitment to transforming the stereotype of technical support into a positive and enjoyable user experience. For over 13 years, I've been deeply involved in the MSPGeek community, lending my expertise to various Managed Service Providers (MSPs), while also serving as the CTO at IntelliComp Technologies.
My journey in the tech world is fueled by a passion for teaching others. I find great satisfaction in imparting problem-solving and critical thinking skills, and offering practical guidance during the troubleshooting process. It's this enthusiasm for mentorship and improvement that led me to my current venture.
Today, as the founder of Rising Tide, I'm focusing on the MSP industry, dedicating my time to coaching and assisting both individuals and businesses. At Rising Tide, we're not just about providing solutions; we're about nurturing growth, fostering innovation, and building a community where everyone can rise together. Whether it's through hands-on problem solving or strategic planning, my goal is to make the IT experience not just efficient, but also empowering and enjoyable
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By the [run]Book: Episode 14
In Episode 14 of By the [run]Book, Mendy and Robbie wrap up v2.206 and break down v2.208, covering key workflow, billing, automation, and portal enhancements. From smarter qualification matching to better project–contract alignment and deeper portal customization, this episode helps MSPs tighten operations and improve control inside HaloPSA.
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In Episode 14 of By the [run]Book, Mendy and Robbie wrap up v2.206 and dive into v2.208. Join us while they unpack a dense set of workflow, billing, automation, and self-service portal enhancements. Highlights include conditional workflow steps, improved qualification matching, project–contract alignment, and powerful new portal customization options. This episode is ideal for MSPs who want tighter operational control, cleaner billing, and more flexible automation inside HaloPSA.
The following features stand out as a few of the impactful changes:
On-call Notification Enhancements #422926
Halo introduced various enhancements to notifications to better support on-call workflows, and Mendy called out that this release note quietly included a massive underlying change. The key takeaway was that important platform-impacting updates can be buried in “notification” notes, so MSPs running on-call should review notification behavior closely after updating.
Assign Contract to Projects & Tasks Created from Sales Orders #1027598
Projects and tasks created from sales orders can now automatically inherit the contract created from that sales order, tightening the link between quoting, delivery, and billing. The hosts emphasized this as a practical fix for MSPs who see project time accidentally hitting the wrong agreement (and wrecking profitability reporting), especially when doing fixed-fee or prepaid project work.
Workflow Automations Using Client/Site/User Custom Fields #1022399
Workflow automations can now use client, site, or user custom fields directly as criteria, reducing the need for workaround runbooks that copy those values onto tickets. The hosts positioned this as a meaningful automation upgrade because it makes routing and logic cleaner, easier to maintain, and more scalable for MSPs with account-specific processes.
Watch Now: By the [run]Book: Episode 14
For easier tracking, check out haloreleases.remmy.dev to filter and search HaloPSA updates by ID, version, and keyword.
Full Feature List:
Added the ability to add Azure/Entra distribution groups as followers | v2.206 #770320 | 1:52
- Allows Entra distribution groups to be added as followers on tickets
- Reduces manual follower management as staff change
- Useful for shared service desks or group-based visibility
Added an option in AI settings to generate an AI summary of the article based on the title, description and resolution Added an option in AI settings to use the AI-generated summary of an article to identify and flag potential duplicate articles before submission | v2.206 #767579 | 2:58
- Automatically generates AI summaries for KB articles
- Uses AI summaries to detect potential duplicate articles
- Improves knowledge base quality and search accuracy
When tickets have a Teams chat open, if the ticket is closed, a closure message will be sent to all chats | v2.206 #635732 | 3:29
- Sends an automated closure message into active Teams chats
- Helps cleanly close collaboration threads
- Reduces post-resolution confusion
Various enhancements to notifications to support on-call notifications | v2.206 #422926 | 4:02
- Improves reliability of on-call notification handling
- Important for MSPs running scheduled on-call rotations
- Includes underlying workflow/notification behavior improvements
A setting has been added to Sales Order Configuration so that a specific Status can be set once all Items on the Sales Order are consigned | v2.208 #1034330 | 10:24
- Automatically updates Sales Order status after consignment
- Reduces manual order lifecycle management
- Keeps order views accurate
The setting "Tickets with the default Organisation/Site must be moved before working on the Ticket" can now be overridden at Ticket Type level | v2.208 #1033540 | 12:51
- Allows specific ticket types to bypass the default org/site restriction
- Useful during intake and triage workflows
- Prevents inconsistent admin vs engineer experience
"Do not disturb" mode for Halo notifications | v2.208 #1028655 | 16:04
- Enables agents to temporarily suppress notifications
- Requires global setting to allow toggle
- Useful for focused work sessions
A setting "When creating Projects and Tasks assign the Contract created from the Sales Order" has been added to Configuration > Sales Orders > Processing Sales Order Lines that allocates Projects and Tasks created from Sales Orders to the Contract created from the Sales Order | v2.208 #1027598 | 17:27
- Ensures project time is tied to the correct contract
- Prevents agreement profitability distortion
- Reduces manual reassignment after project creation
An Item property had been added to the Milestone so that the Invoice Item can be edited/set after creation of the Milestone. This Item will be used when creating an Invoice directly for the Milestone only | v2.208 #1027578 | 20:33
- Allows invoice item changes after milestone creation
- Improves billing flexibility
- Applies when invoicing milestones directly
Added Canned Text Shortcuts for Chat | v2.208 #1024945 | 23:07
- Adds keyboard shortcuts for canned text in chat
- Speeds up repetitive internal communication
- Configured at the canned text level
Additional data has been added to the Invoice Line object to store the Origin Sales Order Line that the associated Recurring Invoice was created from and to store the Occurrence Count for Recurring Invoices | v2.208 #1024614 | 28:23
- Improves recurring invoice traceability
- Tracks original Sales Order line
- Stores occurrence count for reporting
Report display improvement when using customised table html | v2.208 #1024326 | 28:55
- Improves horizontal scroll behavior
- Reduces layout cutoff issues
- Enhances report usability
Added Managed Identity via Azure Arc as an authentication option to the Microsoft Entra integration and Office 365 mailboxes | v2.208 #1024317 | 29:36
- Provides a more secure authentication option
- Reduces credential storage risk
- Supports Azure-first environments
It is now possible to set a Tax Exemption reason for a Halo Customer on creation that will be pushed to Quickbooks when the Customer is not taxable | v2.208 #1024297 | 29:44
- Syncs tax exemption reason to QuickBooks
- Improves finance consistency
- Reduces manual adjustments
A setting has been added to allow recurring invoice lines to be hidden by default when viewing the recurring invoice | v2.208 #1024067 | 29:57
- Keeps recurring invoice views cleaner
- Allows hidden lines to be revealed when required
- Reduces confusion from legacy lines
Multiple changes to available $ variables | v2.208 #1023687 | 32:18
- Expands formatting flexibility
- Adds additional address/currency options
- Reduces need for template workarounds
Added the setting 'Automatically create Change Advise Boards from Teams' to Approval Process settings | v2.208 #1023311 | 32:55
- Syncs CAB boards with Teams membership
- Reduces manual approval admin
- Supports structured change management
A setting has been added to the QuickBooks Integrations setup so that a Closed Date can be entered. | v2.208 #1022558 | 33:16
- Helps protect closed accounting periods
- Prevents retroactive invoice sync edits
You can now use Client, Site or User Custom Fields for criteria on Workflow Automations | v2.208 #1022399 | 33:41
- Enables cleaner automation logic
- Removes need to copy custom field data onto tickets
- Improves routing flexibility
The variable $ SERVICEID can be used in database lookups to obtain the ID of the Service linked to the Ticket | v2.208 #1021534 | 34:21
- Enables service-aware database lookups
- Improves reporting and automation precision
Custom Statistics Tables added | v2.208 #1019726 | 34:32
- Allows scheduled SQL results to be stored over time
- Enables trending metrics within Halo
- Useful for backlog and performance tracking
Decimals are now allowed within the field "Tickets Opened/Closed within the last X days" in AI suggestions | v2.208 #1018082 | 37:42
- Allows finer tuning of AI suggestion windows
- Improves duplicate detection precision
Added a new Knowledge Base setting that allows you to hide FAQ tiles that have no results matching the current search in the Portal | v2.208 #1012783 | 37:50
- Removes empty FAQ tiles during searches
- Improves portal UX
Added a manufacturer field to the suppliers tab of assets | v2.208 #1009501 | 37:57
- Improves asset detail and reporting
- Enhances supplier tracking
Improvements to Qualification matching | v2.208 #1008143 | 38:01
- Improves load balancing logic
- Reduces tickets sticking with unqualified agents
Various improvements to the self-service portal | v2.208 #1007918 | 40:49
- Navigation improvements
- Quick access to My Tickets / My Approvals / My Assets
- Cleaner layout
You can now use Client, Site, User and Organisation level $ variables in the Self Service Portal custom HTML Headers and Footer | v2.208 #1007759 | 43:43
- Enables dynamic, client-specific portal content
- Useful for escalation paths and account manager info
Enhancement to Client-Ticket Type restrictions | v2.208 #1006158 | 47:49
- Updates restriction handling behavior
- Important to review before enabling if already configured
Added a Chat Audit Area Added a new Chat Transcript style | v2.208 #1004851 | 48:34
- Improves audit visibility
- Enhances transcript formatting
You can now set feedback and survey links to be single use | v2.208 #1002898 | 48:41
- Reduces automated survey submissions
- Improves feedback accuracy
Added an Advanced Setting to alter the Tree menu width | v2.208 #999276 | 51:57
- Improves navigation readability
- Useful for long names
You can now make your custom hompage HTML in the End-User portal appear as a sticky banner across all portal pages | v2.208 #996323 | 52:48
- Ideal for outage banners and announcements
- Keeps messaging visible across pages
Added option to exclude non-invoiceable time from budget calculations | v2.208 #994004 | 56:01
- Improves project budget accuracy
- Separates invoiceable vs non-invoiceable effort
Rising Tide Book Club: Think Naked - Week 2
In Chapter 2 of Think Naked, Marco Marsan argues that adults don’t lose creativity: they’re conditioned out of it. This Rising Tide book club discussion explores fear, conformity, unexamined rules, and why real learning requires play, safety, and curiosity in modern organizations.
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About this Series
This discussion guide is part of Rising Tide’s Winter 2026 book club, where we’re reading Think Naked by Marco Marsan.
If you’re just joining us, here are a few pages you’ll likely benefit from:
- Book Clubs, Conversations, and Curiosity for why we started a book club for a technical team here
Chapter Summary
“If you want to be more creative, stay in part a child, with the creativity and invention that characterizes children before they are deformed by adult society” - Jean Piaget
In Chapter 2, You Lost Your Marbles, Marco Marsan explores how people don’t simply “grow out” of creativity — they are systematically conditioned out of it. The chapter argues that over time, fear, rigid rules, institutional norms, and social conformity slowly strip away curiosity, playfulness, and experimentation.
Marsan frames this loss through several forces:
- Fear: mistakes become costly as adults (financially, socially, professionally)
- Senseless rules: norms persist long after their original context or usefulness
- Institutionalized regurgitation: being rewarded for having the “right answer” rather than learning how to think
- Tough-it-out culture: endurance replaces reflection
- Numbness: accumulated stress and responsibility dull engagement
The chapter opens with a consulting story where a leader dismisses Marsan outright, using it as a framing device to explore how organizations often reject discomfort, challenge, and unconventional thinking — even when they claim to want innovation.
Discussion Questions
Use these open-ended prompts to guide reflection and conversation. Remember, there are no right answers!
- What does “losing your marbles” mean to you — and what might you have lost that still matters?
- 'Lose Your Marbles' Saying - Meaning & Context
- Rather than meaning “you’ve gone crazy,” the group explored the older meaning: marbles as something valuable children possessed — and something adults may have lost, not gained, over time.
- Where have fear or consequences made curiosity feel unsafe? How do power and authority shape how you show up creatively?
- How often do you ask why a rule exists, rather than whether you’re allowed to challenge it?
- Where have institutions (school, work, industry norms) rewarded compliance over thinking?
- What would play look like in your work if you weren’t worried about being wrong?
Rising Tide Input for your Consideration
- Your brain is capable of great creativity and capacity. How you use it matters. Here is some research behind some of the concepts Marsan mentions.
- Creativity and Learning require play — and play requires safety.
- We discussed Montessori education, language learning, or professional growth, the group emphasized that playfulness, repetition, and “looking silly” are critical to learning and are exactly what adults are trained to avoid.
- Conformity isn’t safety, it’s a creativity suppressor.
- The group referenced classic psychology experiments (Stanford Prison Experiment, Milgram Experiment) to explore how authority, group pressure, and institutional roles can override personal judgment and moral reasoning. Stanford prison experiment - Wikipedia
- Dead Poets Society - Conformity Scene (1989) HD w/ Subtitles
- https://youtu.be/GDWAKvQemlU?si=AVbkNGLEhC8vn7KV
- Organizational Culture and the 5 Monkeys Experiment | Intersol
- Are rules ever useful?
- Rules are not inherently bad, but we propose that unexamined rules are dangerous. There are rules that deliver shared value and coordination, but there are also rules that persist simply because “that’s how it’s done”
- A recurring Rising Tide pattern emerged: looking for the rule beneath the rule (the underlying reason a rule exists) rather than accepting it at face value.
- As Marsan suggests, “Any Rule represents, at best, the latest thinking on a subject,” but we also considered that a rule represents what was left over from an unfinished discussion, and not even the best answer. It just reflects the last time someone argued about something and not a timeless truth.
- Rules are not inherently bad, but we propose that unexamined rules are dangerous. There are rules that deliver shared value and coordination, but there are also rules that persist simply because “that’s how it’s done”
- Learning is experiential, not transactional.
- We discussed how conformity, rote memorization, and “teaching for the test” suppress critical thinking and actual learning in many modern educational systems.
- True learning involves play, repetition, discomfort, and curiosity, all of which feel inefficient or risky in adult systems optimized for output.
About Rising Tide and our Book Club
Rising Tide helps MSPs and service-focused teams build better systems: the kind that align people with purpose.
Every Friday at 9:30 AM ET, we host Rising Tide Fridays as an open conversation for MSP owners, consultants, and service professionals who want to grow both professionally, technically, and emotionally. In Winter/Spring 2026, we’re walking through Think Naked.
If that sounds like your kind of crowd, reach out to partners@risingtidegroup.net for the Teams link. Bring your coffee and curiosity…no prep required.
Rising Tide Book Club: Think Naked - Week 1
In Rising Tide’s Winter 2026 Book Club, we explore Think Naked by Marco Marsan and challenge the idea that creativity fades with age. Instead, we examine how risk, labels, and permission shape curiosity — and what it looks like to think more like a kid in modern technical work.
Read post
About this Series
This discussion guide is part of Rising Tide’s Winter 2026 book club, where we’re reading Think Naked by Marco Marsan.
If you’re just joining us, here are a few pages you’ll likely benefit from:
- Book Clubs, Conversations, and Curiosity for why we started a book club for a technical team here
Chapter Summary
In the introduction and first chapter, Marco Marsan proposes to the readers that creativity is not lost as we age — it is trained out of us. He cites research suggesting that young children test at very high “genius” or creative problem-solving levels, and that this capacity sharply declines by adulthood.
To return to this childlike, “genius” mindset, Marsan introduces five “rules” that mirror how children naturally engage with problems:
- Wear your cape (be fearless)
- Blockbuster (question defaults and conventions)
- Look at Your Neighbor’s Paper (learn by copying and remixing)
- Show-N-Tell (learn publicly and collaboratively)
- I’m the boss of me (take ownership and agency)
Discussion Questions
Use these open-ended prompts to guide reflection and conversation. Remember, there are no right answers!
- What did you agree with in these chapters?
- What did you disagree with in these chapters?
- Do you agree that creativity declines because of conditioning rather than capability? Why or why not?
- Who or what defines a genius?
- Do any of the five lessons intrigue you more than the others? Which of the five principles feels most uncomfortable to you right now?
- Where do you avoid experimentation because the cost of being wrong feels too high?
- Where in your work do you default to “this is how it’s always been done”?
- What would “thinking more like a kid” actually look like in one small, real decision this week?
Rising Tide Input for your Consideration
- What causes us to lose our creativity?
- The team proposed that people don’t lose creativity as they age, but rather they close off the permission rather than the capability because creativity becomes risky. As adults, mistakes have consequences: reputational, financial, professional. Most environments reward predictability over curiosity, so people adapt accordingly.
- Are children actually ‘geniuses’?
- Evidence that children become less creative over time (and how to fix it) - Idea to Value
- As a team, we felt that the label “genius,” isn’t particularly useful. It’s poorly defined, and even more poorly measured. What matters is not intelligence labels, but how people approach problems: curiosity, iteration, and willingness to engage with uncertainty.
- In fact, as a team we consistently seem to pushback on: Labels (“genius,” “best practice,” or “industry standard”), Claims without sources, and Metrics without definitions.
- Children also don’t ask if they’re allowed to participate, they assume they are. Adults often operate transactionally, constantly checking for permission. That hesitation suppresses experimentation and ownership.
- How does technology factor into creativity loss?
- Convenience is a trade. Offloading is good if the saved energy is reinvested into higher-order problem-solving. As a result, technology can either dull skills or enable deeper thinking depending on how we use it as a tool.
- Automation is welcomed after understanding exists. Technology should support people who know why, not replace them.
About Rising Tide and our Book Club
Rising Tide helps MSPs and service-focused teams build better systems: the kind that align people with purpose.
Every Friday at 9:30 AM ET, we host Rising Tide Fridays as an open conversation for MSP owners, consultants, and service professionals who want to grow both professionally, technically, and emotionally. In Winter/Spring 2026, we’re walking through Think Naked.
If that sounds like your kind of crowd, reach out to partners@risingtidegroup.net for the Teams link. Bring your coffee and curiosity…no prep required.