Most people are doing exactly what they’re told… and that’s the problem.

If you’ve ever felt stuck executing tasks without knowing why, this will change how you work.

Alyssa Nolte sits down with Bill Shander to rethink how we work with stakeholders, ask better questions, and create better outcomes.

Bill shares a bold idea: your boss, your client, even your leadership team often don’t know what they really need. And if you don’t challenge that, you stay an order taker.

This conversation goes deeper than communication tips. It’s about rethinking the future of customer relationships, internal alignment, and how real impact gets made inside organizations.

If you want to do better work, get promoted faster, and stop spinning on unclear direction, this is worth your time.

3 Key Takeaways:

1. “Why” is the wrong question: Asking “why” can make people defensive. Better questions like “how will we measure success?” uncover the real goal without friction.
2. Your job isn’t to take orders - it’s to find the real need: Stakeholders often ask for solutions, not outcomes. Great work starts when you dig into what they actually need, not what they say.
3. The customer should be in every room (even when they’re not): Most decisions ignore the customer until it’s too late. The best teams actively bring the customer perspective into every conversation.

Bill also breaks down how to handle misalignment across leadership, how to balance open and closed questions, and why this skill matters even more in a world of AI and remote work.

Resources & People Mentioned:

1. Bill Shander
2. https://billshander.com/
3. Andrew Davis

Connect with Alyssa Nolte

1. alyssanolte.substack.com
2. linkedin.com/in/alyssanolte