1-on-1 meeting questions

As soon as a wrong trajectory is detected, yes, feedback is needed.

But not before.

Many of these will come off as frustrating and manipulative.

When I, a manager, ask “what is the biggest obstacle facing you and how can i remove it,” I’m offloading the manager-level work of identifying blockers for my team on the individual.

And hey, that might work, your teammate might have an insight you’re missing. But then, if they do have that insight, you’ve volunteered to do a shitload of work for your team.

Thats is, in theory, good- but ive never had a manager that was willing to actually do the work when they asked the questions on this list. They'd squirm out of their offer, and try to rephrase it as something i could do. Leaves a bad taste in your mouth.

The best 1-on-1 meetings feel like a natural conversation between two professional adults. This list of questions can provide some ideas for starting points if you pick and choose carefully, but not all of the questions are a good idea.

Specifically: While it's important to listen to your employee's complaints about the company, it's equally important to avoid giving them the wrong impression that you're going to fix everything for them. Questions like "If you were CEO, what's the first thing you would change?" or "Are there any aspects of our culture you wish you could change?" or "What’s the No. 1 problem with our organization, and what do you think's causing it?" can make employees resentful of the company when the manager can't actually make changes.

Many of these questions can also create a false expectation that it's the manager's job to solve all of the employees' problems for them. It's important to listen to your team and work to improve their situations, but it's equally important that you work on empowering them to solve their own problems where possible. A common mistake for first time managers is to try to absorb every small issue their team encounters, which creates an unsustainable atmosphere of dependency on the manager.

Another common mistake of first-time managers is forgetting that managers must also represent the company to the employee. As a first time manager, it's tempting to think you're going to be the super manager you never had, using your powers to fight back against the company and make everything right for your employees. In reality, you need to balance the employee's wishes against the company's direction. You can't force the tail to wag the dog. Make sure you communicate what is and isn't within your power to change. Avoid commiserating with employees with employees about minutia, and instead set a tone of professionalism and reasonable boundary-setting.

Most importantly: Don't forget to reiterate the organization's goals, project updates, and other company information to employees. It's easy for managers to forget that their employees might not see or hear important developments unless their manager communicates it down the chain. As a manager, it's your job to keep your employees informed and up to date. Simple updates in the form of "Your work on X project is very important for the delivery of Y product, which the CEO identified as our top priority for retaining customers" are much more effective than "When do you think X project will be finished? We really need it." Context and relevance are critical for helping your team make the right decisions.

As a manager as well as a human being, you shouldn't have to ask those questions during a 1:1, the well being of your team should be something you're observing from the inside.

And, more importantly, you should not delegate the responsibility of flagging it when something is wrong. You should know without asking.

Now if there were just a markup language for adding smeantic meaning to hypertext ...