We love talking about one-on-ones here at SoapBox. OK – that might be the understatement of the year 😆 but it bears repeating. These magical little 30-minute chats make teams so much better. Which, in turn, makes companies more successful. And what more could you ask for?

The trick to one-on-ones is asking the right questions. The SoapBox Question Suggester bot can help with that – and we’ve already shared the top 10 suggested one-on-one questions that SoapBox managers use.

Pssst…get our free meeting agenda app to see the Question Suggester in action! Click here to get started.

But today, we’re going to go even further to learn what secret weapon questions managers pull out in one-on-ones to make the conversation truly meaningful.

These questions may seem simple – but they are tried-and-tested to take things up a notch. 

Here are five go-to questions to add to your one-on-one meeting agenda, from amazing managers at Slack, Etsy, Cars.com and more.

1. “How are you?”

Michael Lopp (a.k.a. @rands) is a bit of a management legend, so we thought we’d start with him. The VP of Engineering at Slack talks about one-on-ones on his blog, and admits this is a “vanilla opener” – but says it’s vague enough that your employee can’t help but include a nugget of realness in their answer:

“What’s the first thing they say? Do they deflect with humor? Is it the standard off-the-cuff answer? Or is it different? How is it different? What words did they choose and how quickly are they saying them? How long did they wait to answer? Did they even answer the question?”

Michael says that their answer to this first question can help you discern what type of one-on-one you’re about to have (he buckets them into “The Update,” “The Vent,” and “The Disaster”).

"What’s the first thing they say? Do they deflect with humor? Is it the standard off-the-cuff answer? Or is it different? How is it different?" – @rands on his go-to one-on-one question Share on X

2. “Are you happy?”

Ooof – does it make you nervous just reading this question? What if they say no? What if they look away? What if they start to cry? 😨

Yet this is a go-to for Greg Council, VP of Marketing and Product Management at Parascript. We spoke to Greg for a recent post on what people managers are struggling with, and we made sure to find out what he asks in one-on-one meetings: 

“Asking ‘Are you happy?’ can provide the needed opening that someone needs to share their feelings in a safe way and hopefully head-off any potential problems that could lead to the loss of a valuable contributor,” says Greg.

“Unfortunately, many really good staff can get discouraged to the point that they start looking for their next gig without even signaling that they are unhappy. I think the current thinking is that it is risky to let your manager know you are unhappy or are thinking about leaving until it is too late and the decision to leave has already been made. So managers have to dig to uncover potential dissatisfaction.”

3. “How do you know?”

This one isn’t a stand-alone question. But Paralee Walls, Director of Digital Marketing and Content Operations at Kapost, uses it often.

If someone on her team says, “I think so-and-so is doing something wrong.” She’ll ask, “How do you know?” If someone says, “I think we should try this marketing strategy.” She’ll ask, “How do you know?”

“The reason I ask this question is to give my team the opportunity to think deeper than their gut/watercooler talk/vanity metrics,” says Paralee.

“Do they have data to support an investment in a new project? Did they research buyers’ journeys, do customer/lost opportunity interviews, crawl through Google Analytics data for leading indicators, etc. Everything a marketer does needs to be driven by data.”

"The reason I ask this question is to give my team the opportunity to think deeper than their gut/watercooler talk/vanity metrics." – @Paralee ‏of @kapost on her go-to one-on-one question Share on X

4. “What can I do better?”

We recently compiled a massive list of manager READMEs – and Mike Hostetler, Director of Software Engineering at Cars.com, had this on his README as one of the three questions he’ll ask at the end of every one-on-one.

“This is me opening the conversation to receive feedback from you,” he writes. “Please provide it if you have it!”

It’s a really powerful invitation. It can be hard for employees to volunteer feedback upward – so this kind of question, which he makes sure he includes in every single one-on-one, is super valuable. 🙌

5. “What makes you grumpy?”

This one is from Lara Hogan, leadership coach and former exec at Kickstarter and Etsy. In a blog post on one-on-ones with new hires, Lara includes this question right off the top.

“I flat out stole that first question from Mike Brittain,” she writes.

“He asked me that during our first-ever 1:1 when I started at Etsy in 2013. He said he’d never asked it before. I don’t believe him; it’s SUCH a great question. ‘Grumpy’ is shorthand for so much stuff, but it still keeps the question light and funny and easier to answer.”

It’s a brilliant question for exactly that reason – if you asked new hires (or any employees, for that matter) something like “What makes you upset” or “What’s your trigger?” the conversation immediately becomes more intense.

Grumpy has the right level of quirk to it. 😏

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Now it’s your turn! Try out one of these beauties at your next one-on-one – and see how meaningful the conversation gets.

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