Updated: Nov 17, 2022
Meet regularly. Quarterly? Monthly? No, whenever possible aim for weekly or fortnightly.
Start social. People are human beings not human doings. "How are you going?" is a powerful question if you stop, stay silent and listen deeply to their answer.
Review last meeting's action steps. Avoid drift for you and your direct report by always reviewing action steps from the last meeting early in your conversation.
Create action steps in every meeting. Off the back of point 3, make sure you always finish your one-on-one with some concrete action steps to review next meeting.
What's most important to you, right now? I love this question, ask this every now and then to help your direct report articulate their top priority.
OKR, WIG, lag indicators or lead indicators. Use Measure What Matters OKRs or The Four Disciplines of Execution's Wildly Important Goal, Lag Indicators and Lead Indicators to help your direct report set some clear targets and KPIs for themself based off your team and organization's overall objectives.
Count to 10 every time they pause. Give verbal cues like, "Hmm," and "Yep" and nod your head. But then count to 10 in your mind every time they pause before speaking again and watch how 90% of the time they'll then pick and up and keep going.
Mirror and summarise. After 10 seconds when you do jump in to speak again, before saying anything new, mirror back the one, two or three key words in their last sentence with a questioning inflection and if they still stay silent after that, summarize the last things they've said back to them starting with, "It seems like..." Or "It sounds like..." (for more on this, check out the amazing book Never Split The Difference)
Ask questions. Rather than jumping in with amazing advice, when you do speak try to use open questions and then really listen to what they say. You need to realize they'll probably have key revelations by answering questions and speaking themselves rather than listening to your advice. Take a coaching or facilitating posture and you'll likely create a time and space they love to be able to come to when you meet.
What was most helpful or valuable for you out of today's one-on-one? At the very end of your meeting, ask your direct report what was most helpful or valuable because they'll articulate something they may not have realized and it helps you continue to learn as a leader.