Ask Stupid Questions
Written by: Jules Flesner
Agentic AI and automated technologies are changing business faster than anyone can pretend to understand. New services. New releases. New buzzwords and jargon introduced every week.
Everyone is overwhelmed.
(It's not just you!) Here’s what’s important: your company’s survival depends on leadership asking “stupid” questions that everyone else is too afraid or too busy to say out loud.
Personally, I ask them daily. Finance, accounting, sales, C-suite, IT, legal, ops… I’m coming for all of you with two questions that’ll turn into ten before we’re done talking.
Because I can’t possibly design a seamless customer experience if I only stay in my creative lane. From a prospective client's first click to their final invoice, all of our roles connect.
If I don’t ask, I can’t listen. If I don’t listen, I can’t design. If I can't design, I can't problem solve. If I can't problem solve, I can’t help grow a business through smooth, simple + enjoyable customer experiences.
Stay curious.
Ask ChatGPT and prompt it to explain the answer at a kindergarten level (my new favorite life hack). Remember that ChatGPT may give incomplete or inaccurate data. It can miss context and the nuances of your niche. Ask humans with recent, hands-on, related experience your “stupid” questions. And stop apologizing! You’re not bothering anyone. You're doing your job well. The best business leaders balance expertise with endless curiosity.
