People Pleaser or Sparring Partner
15 December 2025
Finsights
Is generic AI fit for Finance, and if not, what is?
Analysts, bankers, PMs, and risk teams are judged on outputs: models shipped, memos sent, credit calls made, risks flagged, and deals closed. Deadlines are real and the tolerance for error is next to zero. This is all well understood in finance. However, when working with off-the-shelf AI models, we often end up with a chatbot that looks more to please and sometimes makes stuff up when it’s stuck. In our field, this does not work. Finance needs more from their AI assistant.
Finance doesn’t need a friendly assistant.
When your job is on the line, and in finance that feels like always, you need a trusted colleague, an intellectual sparring partner that tells you honestly “your math breaks here” or “that you’ve missed this key part of the thesis”. Standard AI models have been tuned to avoid any confrontation. There is a clear reason for that - it’s by design.
Why do most frontier assistants end up being people-pleasing?
Most frontier assistants are trained in stages that reward “helpful, polite, agreeable” behavior:
They are intentionally tuned to be eager-to-please. They would rather make you feel great about your idea than tell you it's never going to work. Worse, at times they confidently invent or improvise on an answer that fits in your narrative but does not reflect the truth. And it’s a liability analysts and investors can’t afford.
What You Need an Intellectual Sparring Partner
An analyst needs an AI that will challenge their thesis, poke holes in their logic, and force them to sharpen their arguments. Today, analysts rely on their colleagues for this sort of feedback - the type of critical feedback that makes a stronger investment thesis. An AI sparring partner, however, will offer much more.
Imagine an AI that offers proactive insights, asking questions without judgment, and helping you refine your thinking before it ever sees the light of day. In the very near future, your AI will identify gaps in your model, help you find new investment or client opportunities, proactively juxtapose management commentary with expert content in an effort to spot the deltas and investment controversies or even proactively look at your calendar ensuring you are fully prepared for all of your client or management meetings. This agent may not always agree with you or tell you “great job” but it will ensure you don’t miss opportunities, are aware of risks you may have overlooked and have the necessary information assets to be successful.
As one article on the subject puts it, a sparring partner is “not there to be liked. They don’t want to be your friend. They just want to win. They want to test you and make you better. They do that by pushing you, challenging you, forcing you to defend your positions”.
This is the kind of intellectual rigor that AI can bring to the table, but only if it’s designed to do so from the ground up.
This is exactly why we built Finster.ai - an AI assistant custom-built for finance.
The Future is Purpose-Built AI Finance Agents
The AI revolution is here, but knowledge workers in finance can’t simply use any GPT out of the box. The stakes are too high, the data is too specialized, and the workflows are too precise for generic LLMs.
We need AI that is built from the ground up with the realities of our industry in mind.
We need AI that is accurate, citable, and secure.
We need AI that can access and understand the proprietary data that drives our markets.
And most importantly, we need AI that can act as a critical sparring partner, not a sycophant.
This is the future of AI in finance - having a trusted partner that sets you up to win.




