The Art of 1 on 1 Meetings in Tech

What are some strategies supervisors/managers can do to execute the most productive one-on-one meeting?
- I use a set of questions that from the book, “The Hard Thing About Hard Things” by Ben Horowitz. These are stock questions that my team will have prior to our one-on-one meeting and I use them to guide the conversation. We don’t reference these questions during every one-on-one, but quarterly.
- During the one-on-one, focus on outstandingitems from previous one-on-one meetings, and discuss any progress on recent initiatives and any challenges that are blocking them from completing a project.
- A one-on-one is also a great time for a gut check on how employees are enjoying the job and their current responsibilities.
- The more effective one-on-ones are when managers ask for what the bad news is on a project that the employee is working on. The dialogue and problem-solving that follows can be tremendous, and it’s oftentimes something the employee doesn’t willingly bring up, so managers have to ask.

How often should one-on-ones occur, and why?
- We conduct one-on-one’s twice a month and find that to be a good cadence so that there is embedded accountability and also ensures that outstanding items don’t linger for too long without being addressed.

What can employees do to get the most out of their one-on-ones?
- In order for employees to get the most of their one-on-one’s, employees should come prepared with what they want to discuss, be honest and not hide the bad news.