Don Sesler, The Technology Whisperer: As the owner, I have the honor of leading a team of super-smart individuals who share my passion for helping entrepreneurs and business owners not fall victim to complex technology challenges that can kill productivity. We want to tame your technology so that it works for you and not the other way around. What technology problem is making your life more complicated than it should be? Reach out to me and tell me your story.

The Day AI Helped Us Turn Chaos Into a Plan

AI will not magically fix a messy project, but it can help.

We’ve been onboarding a new client over the last couple of weeks, and getting the process started was way more difficult than usual.

Our new client has a complex IT environment, we were moving their entire technical operation from cloud solutions to dedicated in-house servers, and the relationship with their previous IT department was strained by poor communication. Information flow was fragmented and the client was anxious about whether we were going to be able to pull the transition off without seriously disrupting operations.

And, to be fair, we were putting a huge effort in to keep the transition from turning into a pile of disconnected emails, notes, and urgent follow-ups.

We decided to leverage Copilot, our in-house AI tool, to help us bring order to the situation. Frankly it was one of those “now I get it moments” for me on understanding where we are going with AI. With a few minutes of effort, Copilot was able to reference all the email exchanges, internal notes our team had taken, AI notes from virtual meetings, plus the information we had received from the client and previous IT company to create a structured checklist that aligned to our standard onboarding process.

It was the same style of onboarding document we always create, but AI pulled it together in minutes instead of the days it would have taken for one of the humans, allowing us to move forward faster than ever.

Beyond the Thought Partner

I’ve written earlier blog posts about the value of using AI as a thought partner to ask questions, brainstorm ideas, draft an email, or challenge an assumption. Those are valuable uses, and they are often the easiest place to start.

But leveraging AI at the next level is a much bigger opportunity. When an AI tool can safely work with the information your company already creates, including documents, emails, meeting notes, chats, spreadsheets, and process guides, it can help organize operations, evaluate your finances, even coordinate your business development.

It is no longer just a smart consultant. It becomes a smart consultant that can help you get some of the work done.

AI Did Not Replace Project Management

One of my main principles when implementing AI in the workplace is to always have a human supervising and controlling the tool. AI can reduce the administrative and cognitive burden of organizing a complicated effort, but people still provide judgment, accountability, and leadership. In our case, Copilot helped us move past the temptation to analyze every possible scenario before taking the next useful step.

When AI helped us to create a checklist, Copilot did not become the project manager. The checklist was a draft, and not the finished project plan. We did not ask Copilot to validate details, make decisions, or manage relationships. Our humans remained responsible for verifying facts, protecting sensitive information, setting priorities, assigning ownership, and deciding when it was time to act.

For today, that is how I recommend AI be used by small business owners.

Your Information Flow Does Not Have to Be Perfect

In our own business, AI integration is still a work in progress. For example, some AI-generated notes from our phone system are not yet connected to Copilot. If those notes had been available, the planning process might have captured additional context. That is an opportunity for improvement, not a reason to delay using what already works.

We do not need to connect every system before AI can create value. A more practical approach is to treat integration as a continuing improvement process:

  1. Start with the information sources that matter most and/or are simplest and safest to connect.
  2. Confirm that permissions, security boundaries, and human-review expectations are clear before giving the AI tool access to that information.
  3. Evaluate where the AI tool helped, and what still required human judgment.
  4. Document what you learn so the next integration is easier, safer, and more useful than the last one.
  5. As time, budget, and resources allow, choose the next most valuable information silo and bring it into the AI-friendly workspace.
  6. Repeat the cycle gradually, improving the environment over time instead of waiting for every system to be perfect before beginning.

Give AI Enough Context to Help

Finding a safe way for the right AI tool to work with the information your organization already has is a process, and which AI tool makes sense to use as the anchor varies from business to business. For us, Microsoft 365 Copilot made sense because our work already lives in Microsoft 365, but I wouldn’t pitch it to a business that operates in the Google Workspace environment. The important question is not which logo appears on the screen. It is whether the tool fits your environment, respects your security requirements, and can support the way your team actually works.

You do not need a perfect AI ecosystem to begin. You need a useful problem, trustworthy information, appropriate safeguards, and a willingness to take the next step. Sometimes that is enough to turn chaos into a plan.

If you would like help getting AI implemented deeper into your business, feel free to book a consultation with me and I’ll be happy to help.