How to challenge effectively (even when you have less power)

“He who has learned to disagree without being disagreeable has discovered the most valuable secret of diplomacy.”
- Robert Estabrook

Challenging others’ ideas can be, well… challenging.

For many of us, it sits squarely in the too hard, too awkward, too career-limiting basket. And yet, the ability to challenge effectively (whether that be challenging ideas, decisions, strategies, or assumptions) is one of the most critical leadership capabilities there is. 

Without enough challenge, poor-quality decisions multiply, groupthink thrives and innovation quietly suffocates. And with unskilled challenge, cultures become aggressive, fearful or worse - polite on the surface and disengaged underneath.

The real challenge is knowing how to challenge well, particularly when you have less power than the person whose ideas you are challenging.  It’s one thing to challenge your direct report. It’s quite another to challenge a peer, a member of an ELT, the Board or, if you’re a CEO, a room full of powerful stakeholders!

That’s because when power dynamics are uneven, the risks feel higher. 

“Will I be seen as difficult?”

“Will this damage the relationship?”

“Is this worth the political cost?”

Here’s the good news straight from your friendly leadership resource, The Leader’s Digest: 

Effective challenge isn’t about winning, proving someone wrong, or being the loudest voice in the room. It’s about expanding thinking, not shutting it down. 

And, for the record, language matters a lot! So here are 20 practical conversation starters that help you introduce a different perspective, while maintaining respect and credibility:

1. “I have a slightly different perspective. Can I share it?”
2. “Can we sanity-check this for a moment?” (a little bit provocative? Yes, but useful if you’re in a room with the entrepreneurial peeps who get carried away with so-called “brilliant” ideas 😊)
3. “What alternatives have we ruled out, and why?”
4. “What might we be missing here?”
5. “What assumptions are we making that could be worth challenging?”
6. “What risks should we be consciously accepting, or mitigating?”
7. “Can I play devil’s advocate for a minute?”
8. “I’m curious how this would land with (customer/ frontline team/regulator). Do you have any thoughts on that?”
9. “Let’s step into (insert stakeholder) shoes’ for a moment…what would they see/say?”
10. “What would success look like if this went brilliantly? And what would it look like if it didn’t?”
11. “What’s the worst-case scenario? And how likely is that?”
12. “Help me understand the/your thinking behind that…”
13. “What constraints are we assuming are fixed?”
14. “What objections would we hear if we socialised this more broadly?”
15. “Can we explore another angle before we ultimately decide?”
16. “What would change your mind on this?”
17. “If (respected absent voice) were in the room, what might they ask us?”
18. “We’ve covered why this is a good idea. Can we spend a few minutes discussing why it might not be?”
19. “What data would help us be more confident either way?”
20. “I’ve got some concerns and it doesn’t feel right not to raise them…”

And no, “That’s a bloody stupid idea” is not recommended. Unless, of course, you want to be seen as a bit of a numpty.

Speaking of numpty behaviour, if you’re challenging others, there are 5 traps to avoid:

1. Leading with ego, not curiosity.

Challenging to prove you’re right rather than to improve the outcome is pretty obvious to others. Channel open, genuine curiosity to understand.  Ask yourself, “Am I trying to win here, or truly aiming to help the thinking get better?”

2. Publicly cornering someone with more power.

I’ve done this before and have the scars to prove it. DO NOT RECOMMEND. Surprising a senior leader in a public forum can trigger defensiveness or status-protection, regardless of if your point is valid.  A better approach is to flag the issue beforehand or frame your challenge as building on their thinking. If you want to be effective, you should be proactively working to keep others’ defences down. This flows on from the point above too; the intent you bring to the exchange.  

3. Overloading them with data or detail.

More evidence doesn’t always equal more influence. Too much data can feel like a takedown, rather than an invitation. You also risk boring them to tears. NB: this is a trap especially for those who are more naturally analytical.

Instead, offer one or two clear insights, then open the conversation.

4. Using “why” in a way that sounds like an interrogation.

It seems like a small thing, but using the word “why”, as in, “why did you do that?” can feel accusatory.  Instead, swap it for something softer (and more openly curious) like “help me understand…” or “what led you to that conclusion?”

5. Forgetting the impact of our non-verbal signals

Your tone, posture, facial expressions and energy often speak louder than your words. Finger-pointing, eye-rolling or table-thumping are obvious no-nos. But even subtle non-verbal signals like a quiet sigh or looking away or tapping on your phone while someone is speaking can say more than you intend. 

Effective challenge isn’t about being combative or cautious. It’s about being constructive, because better thinking doesn’t come from agreement; it comes from handling different perspectives well.