Best questions for remote 1 on 1 meetings

Best questions for remote 1 on 1 meetings

Make the most of your 1-on-1 meetings as a remote leader

The dreaded (?) one-on-one meeting with your remote employee is coming up again. Last time, there was a lot of awkward silence and banal conversations about the weather. How do you make it better? What should be the agenda? Read on .. 

What makes a good 1 on 1 question?

After having helped organise almost 500+ 1 on 1 meetings via Kaapi, with tens of thousands of insights generated, there are a few things that stand out:

Good 1-on-1 questions are specific, not vague 

Most new managers start 1 on 1 meetings with “Wassup!?”. While this is great to get the banter started, it will hardly elicit the right kind of response. A better way to phrase this would be “What is the #1 place you are stuck at work right now?”.

Good questions are contextual 

Don’t copy paste questions from the internet! Build your own around your team’s context e.g. “What should be the agenda of the team outing next week?” or maybe “Now that Covid vaccinations are here, should we come back to office?”

When in doubt, be kind

How you phrase the same thing matters. Instead of saying “How come you are struggling with this new project X?”, you should ask “What is #1 help I can give you in project X?”.

Ask thought provoking questions in your one on ones

This is your one opportunity to help your remote employee zoom out. Ask them about their career path. Their aspirations, and how those align with the team. Help them introspect.

DO NOT -- ask about tasks, bugs, or deadlines

This meeting is about zooming out, so don’t get stuck on tracking KPIs or goal progress. I have written about this before here extensively. 

Now that you have a grasp of the best practices & tips to ask good questions during one-on-one meetings; here are our top 7 to help you get started.

Q1 - Did I give you actionable feedback in the last 2 months?

This is my absolute favourite 1 on 1 meeting question, and deserves to be on top for one single reason. It removes any blindsides you have as a leader, sets up trust and gives you an invitation to start providing feedback to the team member. Without that context, giving critical feedback out of the blue can sometimes backfire. 

Q2 - Are you clear about your goals for this quarter? What needs clarity?

While not being too transactional, this is a great question to align everyone in the team. I have seen a lot of first-hand cases where the manager thought that everyone knows their goals; but were surprised to find out otherwise. What is written in the KPI / OKR sheet vs how people visualise them are two different things.

Q3 - Are you clear about what it takes to advance further from your current role?

As a leader, one of your most important duties is to develop a career path for your people. What are their aspirations? What are the skill gaps that they have today? Going above and beyond your normal duty, will help build a strong trust. This is a good recurring question for 1 on 1 meetings, and I like to ask it at least once a month. 

Q4 - How are your energy levels for the coming month? What is #1 help you want to ask from me to perform better?

Notice that the question doesn’t ask “How happy are you?” or the boring HR question “On a scale of 1-10 how likely are you to recommend us to your friends”. Being curious about someone’s energy levels will elicit better responses. And you can follow up by asking for an actionable task. 

Q5 - What is #1 thing we can do to make our team meetings more productive?

As I said before, good 1 on 1 questions should be actionable and this is a great one! As a manager who would be running a lot of meetings, you can potentially have a blind spot on making them better. Taking this feedback from your team will help you understand the gaps, and the fixes you implement will 10x the team’s productivity. Win, win.

Q6 - What is #1 product feature we should fast track / build soon?

As a product oriented leader, this is one of my favourites! Everyone (even sales, and marketing teams) wants to contribute to the product roadmap. They all have ideas (some great ones, and naturally some really horrible ones); and this is your chance to empower them. It is also a great way to see if someone is clued into customer understanding and feature requests!

Q7 - How would you describe the vision of our team / company to a friend?

Talking about vision and mission statements can get too heavy for a meeting. And that is why you should position this topic in a more friendly way - “how would you describe x to a friend?”. 

It does not matter if you are doing your 1 on 1 meetings every week, or monthly! Putting such high impact questions on the meeting agenda will help you have insightful conversations, and also build an actionable plan to make things better!

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