Are you asking the right questions?

Now that we can have our generative AI assistants as our main shoulder mates, our reliance on asking humans for guidance diminishes. We used to lean on colleagues, mentors, and specialists for direction—often to validate what we already suspected or to help us get unstuck.

Today, we have voice, Groks, GPTs, copilots, bots, and plugins on standby. Our digital sidekicks are faster, always available, and—at least on the surface—never tire of our repetitive queries.

This shift is profound for some of us. It means we're less dependent on others for answers. But here's the thing: access to infinite answers doesn't help much if you're not asking the right questions.

That's a new skill. It's not just about being curious—it's about being deliberate. It's about understanding the context, challenging assumptions, framing things clearly, and knowing when a question is worth exploring.

The power of the right question hasn't diminished. If anything, it's more important than ever. Now, a well-crafted prompt initiates dialogue and workflows, delineates strategies, creates campaigns, scrutinises data, and occasionally even makes choices.

Here's one of the best-performing prompts I've used so far, at least according to one of my generative AIs:

"Act as an experienced marketing and sales strategist for international B2B companies with long buying cycles. Suggest a structured 12-month plan—formatted as bullet points or a table—with concrete examples of increasing marketing-sourced revenue over time. Assume a limited content team and a moderate advertising budget. Include two alternative approaches with pros and cons. The intended audience consists of decision-makers in the fields of marketing, sales, and business development. Write in a clear, insight-driven tone suitable for an internal strategy presentation."

I asked why this prompt worked so well. According to my assistant and shoulder mate, it combines role, purpose, constraints, and tone in one question. It's specific enough to avoid vague outputs but flexible enough to generate new ideas.

So, how do you train yourself—and your team—to ask better questions?

Start with reflections:

• Could we clarify the specific problem we are aiming to address?
• What assumptions are we making?
• Could you please clarify what constitutes "a good answer"?

Then go beyond:

• How would someone in another department ask this?
• How would a customer ask this?
• What would happen if we answered this question too well—would it lead us in the wrong direction?

The best questions lead to clarity, not just content.

We are entering a time when the quality of your output directly correlates with your ability to ask insightful questions. This is true whether you're building a product, improving a process, or prompting your assistant for help.

This is a muscle worth building if you're responsible for marketing, sales, or digital development.

If you're unsure where to start, that's probably your first question. When you think you're done, ask your assistant if you should ask more questions or change a prompt, as you likely always have when something is important to you.

Subscribe to the Onlinification Hub to explore how GenAI is reshaping our work, our conversations, and our interactions.

Subscribe to get more insights like this.