State of Software: Office 365

A regretful purchase

Open Microsoft 365 and you do not start work, you start a scavenger hunt. It looks polished. It acts like a maze. One click becomes five, then a new portal, then another login. This is not productivity, it is a ritual. Security is the alibi; fragmentation is the reality. If you build or buy software, you know the smell: links inside links, buttons that move or disappear, and settings stacked on settings. 365 is built for big enterprise first, and it shows. That design centre alienates small businesses who need clarity and speed, not policy puzzles. Usability gets traded for layers of control, audits, and compliance. For most small teams, those layers add cost, not value. It feels less like a tool and more like an institution that keeps itself busy.

What is the 365 package?

Practically, it is a subscription umbrella for Exchange, SharePoint, OneDrive, Teams, Entra ID (formerly Azure AD), security and compliance centres, and a constellation of admin portals. Conceptually, it is a governance first operating model disguised as productivity software. Every service speaks permissions before product. That may be fine at Fortune 500 scale; it is brutal for individuals and SMEs who just want to buy email, use docs, and avoid touching a policy engine.

The problem is not that the parts exist. It is that the seams are the interface. You hop between portals that know of each other but do not explain each other. Settings cascade across layers: tenant, product, license, role, and policy. The UI rarely tells you which layer you are actually touching. Failure states default to silence, not guidance. Security is achieved partly because no one can find anything.

I just wanted a Business Microsoft Teams account.

I needed a business Microsoft Teams account to work with my clients after microsoft locked my personal account giving no reason or warning.

It sounds simple: pay for the business version, sign in, and start. Wrong. 365 rears its head. You do not get a single product; you get a tenant, licenses, roles, and a web of portals. Teams turns into a SKU choice, a directory choice, and a billing choice. A small request becomes setup work that feels unrelated to the job to be done.

A single task: delete your account

After purchaisng my 365 account and exploring the 365 suite UI, the first thing I wanted to do was delete my account.

Let's try a basic test. Can you close an account or organisation without a manual? In a user centred world, there is a clear path. In Microsoft 365, the path is distributed across three seperate sites and multiple roles. Not because the operation is technically complex, but because the system is.

Step 1: The user portal is a dead end

There is nothing useful in the user portal for closing an organisation. Most people will get stuck here, not knowing the Admin Center even exists. The portal shows organisation name but no details or link to the admin panel. There is no delete button, no checklist, and no clear link that points you to where the job actually gets done.

Step 2: Admin Center: delete users, licenses, and subscriptions

In the Admin Center, the flow is not just a sequence, it is enforced. Actions appear disabled, hidden, or moved until you complete the one true path. That might satisfy process checklists, but it leaves people guessing. If the system requires an order, say what it is, show why, and offer to do it for me. A simple, human approach would list the blockers, let me click fix all prerequisites, or let me handle them one by one with clear links. For most small teams, the goal is simple closure, not learning a policy engine.

• Order of operations mattersYou cannot delete a directory with assigned licenses. You cannot cancel some subscriptions while users exist. The UI lets you try, then throws terse errors. The system knows the graph; the UI refuses to model it.
• Invisible rolesGlobal Admin versus Billing Admin versus User Admin. Actions appear or disappear across pages with no inline explanation. The product teaches you nothing about why the button is not there.
• Drift between portalsAdmin Center, Azure portal, Entra ID, Commerce. Each has overlapping concepts with different names. You do not navigate; you teleport and hope.

Step 3: A different site entirely: delete the tenant

After the chores, you still have not deleted the organisation. That happens in Entra ID and Azure. Different URL, different mental model. You close the directory only when all dependencies are truly gone: app registrations, enterprise apps, subscriptions, and leftover service principals. None of this is surfaced in the 365 admin UX.

Step 4: The delete button is disabled

You clear users, licenses, subscriptions, and app registrations, and the delete button still stays greyed out. No reason is shown. This is the forced workflow problem again: the system knows what is missing, but the UI will not tell you or help you fix it. A better pattern would display the exact blockers inline and offer a one click resolve, or at least a direct link to each item. Without that, you are pushed to contact support.

Customer service: AI walls and siloed support

When you reach for help, the only clearly displayed phone route is an automated system. It does not triage your case or escalate. It tells you to visit the help FAQ on the website, then ends the call. For someone already frustrated enough to phone, this is infuriating. Which executive thought it was a good idea to tell people who are struggling that, even after calling, the answer is to hang up and contact support through the site. When you do reach a human, the support model is so segmented that you often hear some version of: this sits outside our scope. Billing cannot help with tenant issues. The Microsoft 365 admin team cannot help with Azure directory tasks. Each group is polite, but the structure pushes responsibility away. For practical problems, you are sent in loops.

• One number, many dead endsThe published line routes to an IVR first. It rarely lands you with the person who can act on your exact issue.
• Callbacks without ownershipThe human follow up is friendly, but ownership is limited. If the task crosses product boundaries, you are referred elsewhere.
• Jurisdiction silosTeams are separated by product and policy. If your case touches multiple layers, nobody owns the end to end fix.

Another complaint: it is slow

Even on fast connections and modern machines, 365 often feels slow. Pages pause after each click. You bounce between portals with heavy scripts, redirects, and role checks, so you sit through spinner after spinner. Microsoft owns a cloud platform in Azure, yet the suite still drags. When the flow forces 20 clicks, every second compounds the frustration. In my experience, Azure itself can feel sluggish: basic web hosting feels slower than peers, and VPN gateways and tunnels take a long time to provision and sometimes route traffic with noticeable delay. Performance should be table stakes, not the price of enterprise.

Another complaint: broken flows and repeat prompts

API and flow errors show up at the worst time and make you do the same task twice. Teams is the worst offender. You try to join or switch, an error flashes, and the page bounces you back to a login. Then it asks for the same email and password again because the authentication flow was interrupted. Tokens and redirects drift across services, leaving a stale state where one step succeeds and another fails. The net result is wasted time and a feeling that you are fighting the product instead of using it.

Design diagnosis

• Security theatre via obscurityPermissions are necessary; opacity is not. Hiding actions behind roles without context is hostile. Good security explains capabilities in place and logs tradeoffs.
• System model leaks everywhereUsers should not need to know about tenants, directories, and service principals to accomplish account tasks. The suite makes internal architecture the primary experience.
• Fragmented ownershipEach portal optimises for its own domain. No product owner shepherds the end to end lifecycle with coherent flows. The result is a choose your own adventure of dead ends.

Why this keeps happening

Enterprise suites accumulate power law complexity: decades of acquisitions, compliance overlays, and role based access sprawl. Microsoft 365 is successful despite its UX, not because of it. The incentives reward SKU breadth and attach rates more than flow coherence. That is rational from a revenue perspective. It is punishing from a user perspective.

How could 365 be improved?

Keep small businesses in the user portal, seperate the upgrade to admin/tenant complexity with a billing upgrade, its unnecesary for most businesses.

A kick in the teeth

Microsoft rolled back the deactivation of my personal account, without me even contacting the personal support team. Again no reason given.

Parting thoughts

Microsoft 365 is an engineering feat and a design cautionary tale. If you must live in it, document your flows, centralise role management, and treat the Admin Center as a map of constraints, not a product. If you build software, use it as a reminder: security and usability are not enemies, but when they are negotiated by committee, the user always loses. The job is to hide the seams, not make the seams the job.

A dissapointing experience invigerated with irritation, overall i was immencsy dissapointed that microsoft who should be an industry leader in software design and usability is failing so badly, clouding their popular products with unnecessary complexity and friction.