Accountants are getting better at asking AI to do things for us. We’re familiar with asking it to summarize documents, analyze financial statements, draft emails and automate work we used to spend hours doing ourselves.
But how often are we asking AI to help us think?
Lots of professionals overlook one of the most interesting ways to use the technology. AI can be an incredibly useful thinking partner, especially when you’re working through a complicated decision, preparing for a difficult conversation or trying to figure out why you’re stuck on something.
You don’t have to be particularly technical to use it this way. Honestly, I’ve been doing it intuitively since the first few AI tools hit the market a few years ago. It’s become second nature for me to run my thoughts by an AI agent just to get a second opinion. I think it really just comes down to being curious, creative and willing to have a conversation.
Think about how you work through a difficult problem today. Maybe you call a colleague, talk it through with your partner or spend an hour walking around your office trying to organize your thoughts. Sometimes you already know the answer, but you need someone to ask the right question to help you get there.
AI can help with that process, and here are some ways that you can start experimenting.
1. Use AI to challenge your decisions
Let’s say you’re trying to decide whether to hire another accountant or invest in technology that could take some work off your team’s plate. You probably have a pretty good idea of the advantages and disadvantages of each option. But you also have your own biases, assumptions and experiences influencing how you’re thinking about the decision.
Try asking AI: “I’m deciding between hiring another accountant and investing in automation. What are the pros and cons of each, and what factors might I be overlooking?”
Then give it some context about your firm. Tell it about your workload, your team, your budget and what you’re hoping to accomplish. You can even ask it to challenge your preferred option. What assumptions am I making? What could go wrong? What information would change my decision?
The more context you provide, the more useful the conversation becomes.
2. Practice your client conversations
This is one of the easiest places to start. Imagine you have a client who’s frustrated about their fees. You need to explain the value you’re delivering, but you’re worried the conversation could get defensive. Tell AI what’s happening and ask how you might frame the conversation. Then have it play the client.
Let it push back on your explanation. Ask it to identify where you’re using too much jargon or answering questions the client hasn’t actually asked. Practice explaining your value until you can do it clearly and confidently.
You can also use AI to prepare better questions before a meeting. If a client is struggling with cash flow, ask what you should understand about their business before recommending a solution.
The goal is to walk into the real conversation better prepared to listen, understand and respond.
3. Figure out why you’re stuck
We don’t talk enough about how much time professionals spend overthinking. Maybe you’ve been putting off a difficult conversation or delaying a decision about your firm. Maybe you have a great idea but can’t seem to get started. Instead of asking AI to make the decision, tell it what’s happening.
Try asking AI: “I’ve been putting off this decision for weeks. Help me figure out what might be holding me back.”
Ask it to question your assumptions or walk you through the possible consequences of each choice. Maybe you’re worried about making the wrong decision. Maybe you don’t have enough information. Maybe you already know what you want to do, but you’re uncomfortable with what comes next.
Sometimes getting unstuck starts with understanding why you’re hesitating.
Give Yourself Permission to Think Differently
When I first started using AI this way, I wasn’t following a framework or trying to write the perfect prompt. I was curious. I had questions, ideas and problems I wanted to talk through. So I started having conversations with it.
The value isn’t always in the first answer. Sometimes it’s in the question AI asks me next, the assumption it challenges or the idea I hadn’t considered. I still have to decide what makes sense and what to do with it. But the conversation helps me get there.
As accountants, we spend a lot of time looking for the right answer. What if we spent more time exploring the questions?
The next time you’re wrestling with a decision, preparing for a conversation or feeling stuck, try bringing AI into the process. Tell it what you’re thinking. Ask it to push back. Keep the conversation going. You might be surprised by where your thinking takes you.




