Challenge Every Request To Start Thinking In Outcomes

Challenge Everything, But Do It Out Of Curiosity

When you want to shift more towards thinking in outcomes, there’s one slightly odd habit I’ve found particularly valuable: challenge everything that comes my way – every request, task, bug or idea, whether it comes form stakeholders, users, my team or even myself. 

This isn’t about being difficult or negative or skeptical. It’s about creating space to understand why something is being asked, what it’s meant to change, and how we’ll know it worked. This doesn’t mean you have to stop the whole train every time someone logs a ticket or proposes a new initiative. It starts as a quiet mental habit – your own internal reflex to pause and ask “What is the underlying goal here?”. 

Think of it like being a translator. Someone comes to you speaking in tasks, features, or ideas. Your job is to interpret their words into outcomes. You don’t need to reject the language they’re using; just help surface what they really mean and hope to achieve. 

Curiosity Before Action

Let’s say a stakeholder comes to you and asks “Can we add a new Export To Excel button on this page?” It’s easy to nod and take it as is or even start implementing. But it’s more valuable for both sides to explore: “What’s the underlying problem that makes this button necessary?” or “What do we hope to achieve for users by implementing this?”

Sometimes, the request might mask a larger need – maybe finance is struggling to reconcile data manually, or maybe this team is prepping weekly reports and wasting hours on formatting. Other times, the request doesn’t lead to any meaningful change – it’s just a convenient idea that solves a symptom but not the root cause. 

By approaching it with curiosity, we create an opportunity to zoom out and understand the outcome or assumptions beyon or behind it. In doing so, we give ourselves the chance to drive more value and meaningful results. 

Here’s a few more things that can come our way and questions you should first ask yourself and if no answer comes up, the party bringing it up:

1. A colleague suggests running a customer survey -> “What insights do we hope to uncover? What work or decisions require these insights?”
2. A stakeholder assks for a redesign of a specific page -> “What is not working with the current design, and what user behaviour are we trying to improve or influence?”
3. A manager wants a new KPI added ot the dashboard -> “What decision or insight will this KPI enable that we couldn’t  see before?”
4. A partner suggests integrating a third-party service -> “What specific value will this unlock for our users or business?”
5. A team wants to automate a manual process -> “What’s the current cost (time, errors, frustration) of doing this manually and what change do we expect from automating it?”

Challenging Yourself Too

It’s not just about external requests. The first person I’ve learned to challenge is myself. Whenever I feel a strong urge to “just do it” or “let’s just get it over with” or  “fix that annoying thing”, I stop (most of the time) for a moment and ask: “Am I solving the right problem? What outcome am I actually trying to achieve here?”
And sometimes, the answer validates the action. Other times, I realize I was about to invest time and focus and energy into something that would have made me feel productive, but not actually made progress or drive impact.  And this has an even bigger effect when I am deciding on topics that will affect the entire team. 

Curiosity Driven Mental Reflex, Not Confrontation

Remember that this approach isn’t about slowing things down with endless questioning. It’s about developing this new “muscle” to think in outcomes instead of stopping at the outputs. It’s not a confrontation but a conversation – sometimes just with yourself.

So challenge everything with curiosity and shift from doing things because someone said so to understanding first why they matter and doing them when they do.