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Nick Ang

9 Questions for 1-1s

After nine months of being a team lead, I’ve learned that having 1-1s (one on ones; i.e. a private meeting between a direct report and their manager) is fantastic for many reasons:

  • It builds trust, lubricating work.
  • It multiplies productivity by helping identify work-blockers ahead of time (e.g. I’m stuck on this and can only proceed once Engineering Leadership gives the go-ahead. Is there something we can do to speed up that process?)
  • It enables early detection of team problems by providing a psychologically safe space to talk about problems openly.
  • It helps both parties grow through giving open feedback.
  • Bonus: It builds friendship, sometimes extending outside of work, especially after one of you leaves the company.

Nice, right? But…

It’s not always simple

1-1s are an art. Of course it is, it involves two complex human beings! We, therefore, need to adapt to the habits and preferences of the person we’re speaking to, be that our manager or direct report.

One of my newer direct reports seemed to not be getting much out of our 1-1s, or at least I interpreted it that way as he mentions regularly that he doesn’t have anything to bring up. He’d then suggest that we skip and talk at our next 1-1 two weeks later.

When I noticed this, thoughts rolled into my mind like fresh fog. I’ve been having great, enabling conversations with my other direct reports so far, including the newer ones. What is different here? I know these 30 minutes once every two weeks are worth the time. How can I help him see this in a way that is meaningful for him?

Although it’s probably perfectly valid to not have anything to want to talk about, my hunch was that 30 minutes once every two weeks is probably still valuable, if we tried to lay structure to the call.

So I came up with a shortlist of questions that I thought might steer him to become an active participant in making 1-1s valuable for him and me. Below are the questions, accompanied with short explanations of why I think they are useful questions.

(Context: my current profile is that of a manager who can do the same work as my direct reports. This means that most of the time, I can relate past experiences to what they are experiencing. Not all managers fit this profile, even though employees are usually happier when their bosses can do their jobs. If this is not true of your profile and relationship with your direct report or manager, then filter out some of the questions below that may not be suitable for that relationship.)

1. What have you been working on? How did you find the work? Any parts that made you frown/smile?

Putting on the table some of the work you have been doing in the last two weeks helps your manager frame the rest of the discussion around specific work topics.

The second part of the question is about elaboration, through which perhaps you would be compelled to think out loud and articulate some problems that you hadn’t realised yet. It’s the equivalent of a vet asking a dog owner what’s your suspicion of the cause of the problem? before deciding which topic to go deeper into.

Another good outcome I’ve found from talking about the good and bad is that you breed a sense of camaraderie, which builds trust, which helps get things done faster and smoother.

2. What do you think about the latest tasks that the team is working on? Any opinions?

This helps your manager learn your perspective about the team’s priorities and resulting backlog, which in turn helps him improve his ability to prioritise, communicate, and find interesting work for you, specifically, to do.

3. Were there any decisions you made lately that you aren’t sure about? Or anything open-ended you’d like to discuss?

We all make decisions at our jobs. Sometimes it’s a small decision, like who from Team X you chose to reach out to collaborate on a task. Other times it’s bigger, like deciding on Approach A to building a new web service rather than Approach B. Occasionally, we’re just not sure if we made the best decision.

Bring these up during your 1-1!

It may feel more natural for you to talk about this to your manager, but I’ve also done this as a manager, opening up about a decision I’m unsure about with my direct reports. At the end of the day, openly discussing a decision should already help you make better decisions in the future. If your direct report or manager provides a new perspective, that’s icing on the cake.

4. Do you foresee any blockers that perhaps I can help prevent?

One of the main jobs of a manager is to be a multiplier for the team’s output, otherwise that manager is just a hindrance, a hoop to jump through. The most direct way to multiplying output is to remove blockers for people.

Person X need to talk to Person Y before Task Z can proceed? Offer to reach out and link them up and, even better, be the one to provide context so that things move forward.

This only works if your manager knows the blockers. Hence, the relevance of the question during a 1-1!

5. How are you feeling about work?

This is about morale. Your manager probably wants to know if you’re feeling uninspired or otherwise in a rut, so that he can find the root cause and, if it is fixable, fix it. If it’s not fixable directly, he might at least be able to help think of a workaround.

A framework I always refer back to is a Venn diagram that guides our internal hiring process at Smartly.io. It consists of three circles: competitive advantage, true motivation, and impact for the company:

a Venn diagram depicting employer-employee symbiosis I call this the magic of employer-employee symbiosis!

At any time, an employee may feel like the work they have recently done does not hit the sweet spot of leveraging their competitive advantage, aligning with their current motivations, and maximising their impact on the company. Talking about you’re feeling about work is how your manager can realise this and see how he can help. That could be anything from doing an online course on a new area of expertise, finding an exciting new project, to seeking a new role in the company.

6. How are you feeling about life outside of work?

I see this question as a continuation of the previous one, except it focuses on uncovering the true motivation part of the Venn diagram.

We live in a world where employees dabble in different roles as a way to figure out who they are and where their strengths lie. A company (and its cadre of managers) is better able to keep talent by acknowledging this reality than stubbornly resisting it. If over the weekend an employee read a random article about, say, product management, and became convinced that that’s her calling, we should at least consider her thoughts.

There’s also the chance that something had happened in your life outside of work and that it may affect your attention or energy at work. Remote work with a toddler at home has been more draining than you thought, your parent is suffering an illness or something else that just… happens. Life happens. Let’s talk about it and see what arrangements we can come up with to rough out the storm.

7. Any feedback to give to me?

If there’s nothing else that comes out of the 1-1, at least walk away with some pointers for growth!

8. Any feedback to give/given to others in the team recently?

No? Why not? You should! :)

9. What’s your focus in the coming 2 weeks?

Hearing what you’re planning to work on, your manager can provide suggestions on approach, point out potential blind spots, reconsider assumptions made, share relevant resources, offer to do something that could ensure smooth passage, and so on.

As a manager, I find that it helps to know the broad strokes of work that each of my direct reports will make in the coming weeks because then I can have an overview of the team’s work, prevent duplicate work, draw connections among related tasks, and so on. Again, this is about being a multiplier on the team’s output.


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