“Head-down” ICs and 1:1s

Started my first ever Engineering Manager job last year after ~20 years of dev, and on the whole I’m enjoying it a lot. However, I keep coming up against one particular problem that I don’t know how to solve - or whether it’s something to “solve” at all.

My employer mandates that I have monthly 1-hour 1:1 meetings with each of my engineers. The format is more-or-less up to me and the employee, so long as I come out of the meeting with recorded bi-directional feedback. I generally use the meetings as a mini retro for the employee where I record what’s going well, what isn’t going well, and what actions we can take to improve things.

For most of my employees, I have no problem filling an hour - we talk over ongoing projects, participate in harmless gossip/slander, and generally hold each other accountable for work that needs done in the coming month. They are generally the most productive meetings I have as an EM because they are one of the few avenues my team have to speak freely without the beady eyes of stakeholders watching them. I get a real sense of what needs done and where problems may lie.

However, some of my employees simply won’t engage with the format, often to quite extreme degrees - proper blood-from-a-stone conversations are happening. These people are all classic “head-down” developers - people who only report the essential facts of their work and/or outright avoid raising problems out of fear that myself or other leaders will mark them out as troublemakers. For the life of me I can’t get them to speak their mind on anything, and I’m frequently coming out of their meetings after only 15 minutes with a feedback sheet that says nothing more insightful than “Everything’s going fine” (which often is simply a bald-faced lie that can be proven by a cursory glance at Git or Jira) - it’s driving me mad, and my boss is starting to raise his eyebrow when issues my quieter reports have are forced to surface.

For both EMs and ICs reading this post - how do you make the most of a 1:1 where someone doesn’t really like to chit-chat? What stops you from speaking your mind in a meeting with a manager? I know on some level it’s about a build-up of trust and results, but I’m wondering if maybe there are changes in approach I could take to in order to improve things in the short-term. I’m open to trying anything!