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If you’re looking for a casual, open-ended way to kick off a one-on-one, ask “How’s life?” instead. It may not seem like a big difference, but it makes a big difference. “How’s life?” gives permission for someone to talk more personally about life — about what they did that weekend, how their family is doing, how their personal side project is coming along, how they’re managing their workload.
A one-on-one meeting isn’t a reporting session. It’s not an accountability tool. A one-on-one meeting is your radar. It’s your metal detector. It’s one of the only ways you have to unearth what’s actually going on in your team, and what an employee is thinking and feeling. Possibly my favorite question to ask to instead of “What’s the latest on X?” is “Can you tell me about what’s been most surprising about working on X so far?” If an employee has found something surprising, good chances that you’ll find it surprising too.
“How can I help you?” The intention behind this question is fantastic. It’s lazy. It makes the person receiving the question do all the hard work of having to come up with the answer. It’s also a very hard question to answer, especially on-the-spot and given that you’re a person in a position of power. You’re asking a person to critique you. Suggest something you think you can be doing to help. Then ask, “What do you think?” For example: “I was thinking I’m being too hands-on on this project. Should I back off and check-in with you only bi-weekly? What do you think?” By being targeted in what you suggest — and suggesting it yourself — you make it easier for that person to share the exact ways in which you can support them.
Focus your efforts on asking specific questions, instead of defaulting to general ones. For instance: “What do you think is the most overlooked area of the business?” or “Where do you think we’re behind in, that other companies are excelling at?” Notice how specific each of these questions are. The more specific the question, the more effective they are.