End every 1:1 with this question

1:1s can take many forms. Some employees bring a long list of topics to cover, some bring only the burning issues, and others bring nothing at all. The best 1:1 meetings are consistently held and go beyond a project sync. A project sync can be a component of them, but you're really getting only a fraction out of them if you only talk with your employee about what they're working on.

An essential element of a productive 1:1 is trust. In the book Radical Candor, author Kim Scott gives a great suggestion on where to start to shift culture in a section titled "Start by asking for criticism, not by giving it":

Bosses get Radically Candid guidance from their teams not merely by being open to criticism but by actively soliciting it.

Recently I've been trying to end all 1:1s with my employees with the question "What can I do even better on?" The consistency of bringing it every time is essential, because the first few times you ask it, you may get answers of "can't think of anything!" or "everything's good!". That may even be true from your employee's point of view, but asking the question plants a seed in their mind. They'll start writing down things they notice, little suggestions that they'll bring to a future meeting, and there's less pressure when you only ask randomly or infrequently.

And the goal is to get actual suggestions, not just get good manager points for asking the question! The reasons there are twofold:

1. You should be interested in improving, whether you're new to the manager role or have been in it for many years. If you're stuck in place then you're not serving your team as well as you could be.
2. It helps build trust that feedback is a two-way street. When you point out areas for improvement for your employees, you're not sending down stone tablets from the mountain. You recognize that you're human, that you make mistakes, and that employees on your team have valuable perspectives on how you can do better.

The "even better" part is important too. "How can I suck less?" is roughly equivalent but "even better" gives a gentler on-ramp to their suggestions. What you say after receiving feedback is important too. If you get defensive and push-back, then you've botched it, you're unlikely to get feedback again from that person anytime soon. That doesn't mean you have to agree with the feedback, but you should listen to both what your employee is saying and the underlying emotions and consider if how you are perceived is at odds with the kind of manager you want to be.

It takes vulnerability to "go first" and open yourself up to feedback, but it will help build up the muscle and shift from an atmosphere where constructive criticism is only brought up when the situation has really escalated to one where constant improvement is the goal, and the feedback loop gives you that solid grounding to keep leveling up.