Soft Openings

As a management technique, the 1:1 meeting is a classic, a cornerstone of building and maintaining a good relationship with the people who work for and with you. But strong professional relationships don't "just happen"; making sure the 1:1 is time well-spent involves both steering the conversation in a useful direction as well as giving the other person the space and comfort to share with you what's really going on.

By design, the 1:1 has an open-ended agenda. You're leaving space for the other person (often your direct reports) to bring up what's important to them. But how do you get there? Most people are not ready to just blurt out their problems to their manager, and there may be important issues they do not even think worth discussing. To get the conversation started, I like to begin with an open-ended, non-judgmental prompt. Most often, something like the very simple:

"So, how's it going?"

As an opening, this is pillow-soft. It's a content-free invitation to talk about whatever. Sometimes, you'll get nothing but a nod, or 5 minutes on topics outside of work (though this can still be valuable for building a personal relationship). But sometimes there really is something going on with the other person, and this is all the invitation they need to let it start spilling out.

If I get nothing, I might try a slight reformulation:

"So, what's on your mind?"

Still just as content-free as the previous prompt, but now they can't get away with just replying "good" and leaving it at that -- a sensical response requires them to state something. Anything at all, even if it's trivial. I like to use this version with people who are not, by their nature, over-sharers.

Quite often, this is enough to lead us into half an hour of conversation, especially once I've built a rapport with someone. But if I'm stuck for topics, I'll start digging into my bag of Conversation Starters, trying to kick something loose from their mind with an unexpected question.

"What's the most fun part of your job right now?"

This question assumes that some part of the job is supposed to be fun, or at least engaging. This is true for software, and for creative professionals in general, but perhaps not every job. Still, I just want them to tell me what part of their job they're enjoying; maybe we can lean into that, help guide their career a little.

"What's the worst part of your job right now?"

I like this for generally upbeat people, those who are unlikely to complain unprompted. Even if you love your job, there's something about it that's crummy; tell me about it. Maybe we can do something about it, maybe not, but I often find some promising ideas for improvements come out of giving happy people explicit permission to grouse about something.

"If you could wave a magic wand and fix anything about the Company, what would it be?"

Similar to the previous question, but you might not get the same answer! If people are noticing that something sucks, even if it doesn't (yet) impact their day-to-day much, it's probably important that you know it sucks too, and as a manager, you're more likely to be able to do something about it.

"Who's bring really helpful to you right now?"

I like fishing for third-party compliments. Not only is it pleasant to talk about people who are helpful and supportive, but you might uncover some important inter- or cross-team support that you were unaware of. Conversely, their answer can also be instructive in terms of who they choose not to talk about.

"What kind of projects do you want to do more (or less) of?"

Similar to the "most fun" question, but project-focused.

"Are there any skills/technology you want to spend time learning?"

Keeping your employees up-to-date on training is important -- why not solicit them for ideas?

"What do you think about Company Initiative X?"

If they're part of the initiative, what do they think its prospects for success are? And if they're not, how well is the company doing spreading awareness internally about Initiative X?

This list is by no means exhaustive. All sorts of things can work, as long as it gives the other person a fresh lens to view their job, the company, or your industry through. Other examples off the top of my head:

  • "What would you do if you were CEO?"
  • "How do you think AI is going to affect the business?"
  • "Who is the one person on your team we can't afford to lose?"
  • "Do you find yourself more productive on certain days, or at certain times of day?"

For some of these questions, the answers might not change very often, if at all, so I won't ask the same person the same question more than once or twice a year. Moreover, this sort of open-ended delving can get stale if overused. It's great for building a relationship or getting one out of a rut, but I would still expect the bulk of 1:1 time to be spent on current issues, problem solving, feedback and other regular items. For me, it's a 'feel' thing; if 1:1s with a person start feeling rote, that's when I start looking for things like this to shake us out of our routine.

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