By Eric Overfield – August 2025 

Artificial Intelligence is transforming the workplace, but not all AI tools step into the ring equally equipped. For those of us that have invested in the Microsoft 365 ecosystem and are looking to provide AI driven productivity solutions to our team, we have a few principal options. In one corner, we have Microsoft 365 Copilot, the integrated AI sidekick built into the Microsoft tools our teams already use every day. In the other, ChatGPT, the wildly popular AI leader of generative AI that's tackling everything from a general web search replacement, coding helper, to creative writing and much more. How then do we decide which one is right for our organizations? 

Each tool has their pluses and minuses, and sure, there are other tools available. What I want to do here is break down the practical differences between Microsoft 365 Copilot and ChatGPT, the two primary tools you all are considered, based on your feedback, from security and integration to real-world use cases and customization. Let's help you make an informed choice. 

Side note: Yes, there are many other AI tools, some quite powerful, such as Gork, Claude, Gemini, and DeepSeek, just to name a few. To keep this tight for now, we will only be considering Copilot and ChatGPT as that is what you have been telling me are your top contenders as well. 

Further, consider this your pre-match analysis ahead of our upcoming webinar "AI SmackDown: Microsoft Copilot vs. ChatGPT" on August 28 (details at the end).  

Spoiler alert: it might not be a knockout fight, but understanding where each AI wins on points will empower you to pick the best partner (or partners) for your workflow. 

Setting the Stage: Why AI, Why Now?  

Less than a year after OpenAI's ChatGPT went viral in late 2022, we started to see employees bring their own AI tools to work. In other words, your employees have likely been experimenting with ChatGPT or similar tools on their own to draft emails, brainstorm ideas, or crunch data. AI has moved from buzzword to boardroom priority faster than we have seen with other new technologies. 

To paraphrase many others, AI isn't here to take away our jobs, it's here to take away our busywork. Rather than replacing people, modern AI aims to free us from the drudgery, you know, the endless formatting, transcribing, scheduling, even number crunching, so we can focus on the creative and strategic parts of our jobs. 

This promise explains the rush to adopt AI in the enterprise. But it also raises a few big questions. 

1. Is this all hype? 

1. If there is some truth to the promise, which AI tools can we trust to actually deliver that benefit, securely and effectively, in our organization? 

Let's assume for this post that there is some truth to the hype. While I believe there are limitations to what AI may achieve, I personally see huge benefits of my daily Copilot and ChatGPT usage. That being the case, this is where our two contenders step into the ring: 

• Microsoft 365 Copilot (Copilot), unveiled in early 2023, is Microsoft's answer for adding AI directly into the workplace apps (Teams, Word, Outlook, Excel, etc.) that many businesses already use. It's not a separate app per say, it's an assistant living inside Microsoft 365 designed to inherit your company's security controls and work with your business data by default. Microsoft 365 Copilot is not exactly the same as Microsoft 365 Copilot Chat (Copilot Chat), Microsoft's "free" offering more closely related to ChatGPT's free offering. 

• ChatGPT, launched publicly in late 2022 by OpenAI (which Microsoft has an ownership interest in), is a conversational AI chatbot accessible to anyone with an internet connection. It's incredibly knowledgeable and flexible, but detached from any particular enterprise system. Out-of-the-box, it knows a lot about the world (from its vast training data) but nothing about your company's files or context unless you give it that info explicitly. ChatGPT is a primary leader in generative AI, releasing new updates to foundation models used by many AI tools including Microsoft 365 Copilot. Most recently OpenAI released GPT-5, which at this time is only available to ChatGPT users. 

Both tools are powered by advanced AI (GPT-4 and beyond) under the hood, and both can generate human-like answers to a huge range of prompts. So what sets Copilot and ChatGPT apart? Let's break down the matchup category by category. 

Security & Privacy: Trusting AI with Your Data 

One of the first questions every organization asks me when they are considering AI in the workspace: Can I trust AI with my business data? This question makes sense as the true power of AI in the workplace is AI using your own internal data to drive insights, make recommendations, and drive productivity gains. 

Here, Microsoft 365 Copilot comes in swinging hard: 

• Copilot keeps your data inside your Microsoft 365 cloud. When Copilot processes your prompts, it's operating within the security and compliance boundary of your Microsoft 365 tenant. Your data isn't leaving for some unknown server; it stays in OneDrive, SharePoint, Exchange, etc., and the AI model (running on Azure) comes to your data to generate the answer. Microsoft designed Copilot so that it inherits all your existing permissions and policies. For example, if you don't have access to a certain SharePoint site, Copilot won't suddenly show you content from it. Everything is permission-trimmed, and activities can be logged for audit. In short, Copilot is enterprise-ready by default, with privacy and compliance features that meet the needs of IT and legal teams. 

• ChatGPT on the other hand lives in the public cloud. If you use the free or Plus version of ChatGPT, any data you enter is sent to OpenAI's servers. While OpenAI doesn't exactly snoop through your prompts, they do log data to improve the model (unless you opt out via settings or use their paid enterprise offering). For organizations, this is a red flag for sensitive information. I believe this is why many companies I talked to temporarily banned employees from using ChatGPT at work early on.OpenAI has responded with ChatGPT Enterprise, which offers encryption, an admin console, and a guarantee that your prompts won't be used to train models. Fundamentally, using ChatGPT with proprietary data means your data is leaving your controlled environment and being processed on an external system. If you connect ChatGPT to your internal systems (say, through a plugin or API), those connections must be carefully secured. OpenAI says ChatGPT can be used securely, but it's not "secure-by-default" in the way Copilot is within a managed Microsoft tenant. 

In summary: Copilot is like an employee who has signed your company NDA on day one, whereas ChatGPT is more like a freelancer. Incredibly talented, but you wouldn't hand them your secret sauce without a contract. 

Many organizations will choose to keep the crown jewels (sensitive data, client info) behind the Copilot wall, and use ChatGPT in safer, non-confidential scenarios. We'll discuss governance tips later on, but it's clear that if strict data compliance is a must, I believe Copilot scores an early point in this round. 

Integration & Ecosystem Fit: Where Do These AI Live? 

Another major difference is where and how you interact with Copilot vs. ChatGPT: 

• Microsoft 365 Copilot is embedded in the tools you already use. In Teams chats or meetings (my favorite Copilot usage scenario), Copilot can be called on to recap discussion or answer a question in context. If you're working on a Word document, Copilot sits inline and in a sidebar ready to help write or format content. In Outlook, Copilot can draft replies or summarize an email thread with one click.This tight integration means zero context-switching and seamless integration. You don't have to open a separate app or browser to use Copilot, it's all right there in Teams/Word/Excel as a feature. Copilot also inherently understands the context of what you're doing. If you're in a spreadsheet, it knows to output tables or charts. If you're chatting in Teams about a project, it can fetch info from the project OneNote or summarize recent messages.The user experience is designed to feel like an assistant sitting next to you, within the flow of work. 

• ChatGPT lives in its own chat interface (or API). To use it, you typically go to chatgpt.com or perhaps use a third-party integration or a browser extension. It's a separate window where you ask a question or give a task, and then you manually bring the answer back into your work.That means ChatGPT is application-agnostic. You can use it for practically anything (code, writing, calculations, advice) but you, the user, have to provide any specific context every time. For example, if you want ChatGPT's help on a Word doc, you need to paste the relevant text into the chat. If you want it to analyze data from a spreadsheet, you have to give it those numbers (within reasonable limits). The advantage here is flexibility,  ChatGPT isn't tied to Microsoft or any vendor.ChatGPT can integrate via API into other platforms, and indeed many apps now offer built-in ChatGPT plugins. But out-of-the-box, it doesn't "know" what file or email you're looking at unless you tell it. 

From a workflow perspective, Copilot can save you more clicks if you're a Microsoft 365 shop! Copilot is woven into the environment. It's especially powerful for those who spend a lot of time in Microsoft Teams or using other Microsoft 365 Office apps.

ChatGPT might require more copy-pasting or switching between windows, but it can reach beyond Microsoft's world. For instance, if part of your workflow is in Google Docs or some custom CRM, ChatGPT (through APIs or browser add-ons) could be extended to help there too, whereas Copilot focuses on Microsoft's ecosystem. 

To illustrate: imagine you need to create a sales report. With Copilot in Excel, you could ask, "Help me analyze this sales data and highlight 3 insights," and it will generate a response within Excel, perhaps even making a chart for you. With ChatGPT, you'd open ChatGPT, possibly upload or paste some data, and ask a similar question – it might give a great narrative answer or even pseudo-code for analysis, but you'll likely be stitching that back into Excel yourself. 

Copilot is an AI that's part of your team's toolkit, while ChatGPT is an AI you consult externally. Neither approach is inherently "better", it depends on whether you value seamless integration (Copilot) or broad flexibility (ChatGPT) more for a given task. 

Getting Real Work Done: Use Cases and Strengths 

What kind of tasks can Copilot or ChatGPT actually help with? Here's where each shines: 

Content Drafting & Editing: Both Copilot and ChatGPT can draft documents, emails, or presentations, but in different ways: 

• Copilot can natively and inherently pull context from your organization's content. For example, it could draft a project update by drawing on a project plan stored in SharePoint, ensuring the output aligns with known facts from that plan. It might even suggest inserting a chart from a related Excel file. Copilot is great for producing first drafts of work-specific documents, another of my primary Copilot usage scenarios.Think proposals, meeting agendas, or intranet news posts, where having the content grounded in your internal data is valuable. 

• ChatGPT is superb for creative writing or generalized content. Need a catchy introduction for a newsletter? Want to brainstorm four variations of a marketing tagline? ChatGPT will give you imaginative, well-phrased options. It's also powerful for longer-form writing like blog posts, tutorials, or summaries of public knowledge. The key is that ChatGPT doesn't know your internal lingo or proprietary info unless you provide it. So it might not automatically include the latest sales figures in that project update (unless you feed them in), but it might produce a more fluent narrative or a clever analogy. 

Data Analysis & Number Crunching: 

• Copilot in Excel can execute formulas, create PivotTables, and generate charts on command. You could ask, "Copilot, what were our top 3 products by revenue last quarter?" and if the data is in your spreadsheet or database (and you have permissions), it will retrieve the answer or even visualize it. It understands the structure of enterprise data if connected (through the Microsoft Graph). Also, Copilot's answers can include citations/links. For instance, it may give you a summary and say "Source: \Q4_Sales.xlsx" so you can trust where the numbers came from. I see AI and data (Excel and Microsoft Fabric driven) as a primary driver of AI investigation and adoption, yet I see that Copilot and Excel still have room for improvement. 

• ChatGPT can analyze data too (especially if you have ChatGPT Plus with the Advanced Data Analysis plugin). You might paste a chunk of CSV data or ask it to analyze trends, and it can output python-like analyses or plain language insights. It's quite powerful for ad hoc analysis when the data isn't already in a company system. However, it's not directly wired into your databases, you have to supply the data. Also, if you have very large data sets, ChatGPT might hit limits (context length or file size). Let's also ignore some of the recent GPT-5 rollout issues, everyone seems to hit and miss when they release new models. 

Meetings, Emails, and Communications: 

• Copilot in Outlook can summarize long email threads and even draft replies. If you've ever returned from vacation to a mountain of emails, Copilot could be a lifesaver by highlighting the key points from those threads.In Teams meetings, Copilot can generate recap notes, action item lists, and answer questions like "What decisions were made in this meeting?" while you're in the meeting or afterward (again one of my favorite use-cases). It's like having a super attentive assistant who never misses a detail or deadline.One nifty Copilot trick, it can flag commitments. If someone in a meeting says "I will send the report by Friday," Copilot can catch that and list it as a follow-up task for them! 

• ChatGPT isn't embedded in your email or meeting by default, but you can still use it to craft better communications. Many people use ChatGPT to polish the tone of an email ("make this sound more professional and friendly") or to practice responses to tricky questions.Some even feed it transcriptions of meetings to get summaries (though that requires copying text or using a third-party service). If you combine ChatGPT with tools like Zapier or Outlook scripts, you could automate certain replies or summaries, but it's more DIY. 

Knowledge Discovery & Q&A: 

• Copilot leverages auto-integrated features of Microsoft 365, the Microsoft Graph and a Semantic Index. Without diving too deep into tech, this means Copilot can search your organization's knowledge (Teams chats, transcripts, SharePoint Sites, documents) in a smarter way than keyword search. In fact, the semantic index included in Copilot is what allows Copilot to excel in terms of speed and reasoning of your data in a way not possible with ChatGPT.You can ask Copilot questions such as "Has our team ever done a contract with Creospark before? What's the summary of that deal?" and if that info lives in your Microsoft 365 tenant (say, a OneNote or an email), Copilot will find relevant content and compile an answer, complete with references. This enterprise search capability is huge, I see it as a corporate librarian who reads everything and instantly fetches what you need, even if you didn't know where to look. 

• ChatGPT has knowledge up to its last training cut-off (and with GPT-4's updates or web browsing, it can handle a lot of general queries). It's fantastic for general knowledge Q&A. Ask ChatGPT to explain a concept, translate something, or even solve a coding problem.But it won't know anything about the "Creospark deal" unless that was public or you provide context. However, if you load your company docs into a private version of ChatGPT (via fine-tuning or using Azure OpenAI with your data), you can achieve a similar effect. That's more complex to set up, whereas Copilot's advantage is it is pre-wired to your content with minimal setup. 

In short, Copilot's strength is using your organization's universe of data to deliver answers and actions, staying context-aware and accurate to your internal knowledge.

ChatGPT's strength is its universal knowledge, creativity, and using the latest foundational models, which is ideal for tasks that don't require internal data or when you need out-of-the-box thinking. 

It's worth noting that both tools are improving rapidly, and breaking things along the way. Microsoft is expanding Copilot into more scenarios (i.e. Copilot in Windows to assist with PC tasks, and domain-specific ones like Sales Copilot or Security Copilot for specialized tasks).

ChatGPT is also evolving, very fast, with new plugins and multimodal capabilities (image understanding, etc.) that could play into office scenarios (imagine snapping a photo of a chart and ChatGPT interpreting it).

Our use-case comparison will have to keep shifting as each gets "buffed" with new features.