5 Questions to Ask the Employee Who Shoots Down Every Idea

Why Employees Resist Change

Resistance often isn’t just a bad attitude. Across four Leadership IQ studies involving more than 79,000 employees and leaders, only 15% of employees say they always understand the rationale behind their organization’s strategy.

That gap matters. The studies found that understanding the rationale explained about 24% of the variation in employees’ belief that the company needed to change. In a separate analysis, employees’ confidence in their ability to succeed explained about 23%.

When people don’t understand why a change is happening, they’re likely to see it as arbitrary or capricious. And only 15% of employees say their organization always openly shares the challenges it faces, so there’s a good chance you’re asking people to make a change you haven’t fully justified.

The Five Questions

First, narrow the objection to something specific. Ask, “You said this won’t work. What’s the single biggest risk you see?” It’s hard to do much with “this whole thing is going to fail,” but if the employee says customers won’t know whom to call during the transition, you’ve surfaced a problem you can actually work on.

Second, ask what would have to be true for it to succeed: “If we did this and it worked, what would we have had to get right?” Someone who’s seen a similar change fail might know exactly what was missing last time.

Third, test nostalgia directly. When the objection is “it used to be better,” ask, “What specifically worked then that we’ve lost?” The answer may be worth restoring; if they can’t name anything specific, you’ve moved past treating “the old way was better” as a complete explanation.

Fourth, ask them to help with the fix: “What would you change to reduce that risk?” If they don’t have an answer immediately, give them some time to think.

Fifth, shrink the stakes: “What if we tested this with one team for two weeks before rolling it out to everyone?”

What This Sounds Like at Work

Let’s say a manager, Nadia, proposes a new process for handing customers from sales to account management. An experienced employee, Ray, immediately says customers will get bounced around and the old way was better.

When Nadia asks for the biggest risk, Ray says nobody will know who owns a customer between the signed contract and the first call with the account manager. Sales will assume the handoff is done, while account management will be waiting for information. In the meantime, the customer will keep calling Ray.

Asked what they’d have to get right, Ray says somebody needs to own the customer until the account manager confirms they’ve taken over. And when Nadia asks what worked about the old process, he says customers always had a named person to call.

Those are useful concerns. Nadia can build that ownership rule into the process, ask Ray to help test it, and try it with one team before a wider rollout. She’s learned something she would have missed if she’d cut him off with “You’re always so negative.”

You won’t always get that much useful detail. Some employees will keep repeating that nothing will work. When that happens, you can be direct: “I’ve heard that you don’t think this will work. I need you to identify the specific problem you want us to address.”

Keep the Conversation on What Happens Next

The trap is trying to win a battle of predicting the future. You say it’ll work, they say it won’t, and you’re stuck arguing about a future neither of you can prove. So keep bringing the discussion back to the specific risk and what you can do about it.

You may still end up with an employee who dislikes the change, but they can dislike it and still help you test it properly. And if the test confirms their concern, fix the problem before asking the rest of the company to use the new process.