One-on-Ones That Actually Work: A Playbook for New Leaders (and everyone else)

One-on-ones often drift into glorified status updates or worse get cancelled when things get busy. When done well they're quickest way to build trust, clarity, and momentum in team. Ben Horowitz once received criticism for discussing their importance. Carlo's guide to running great 1:1s blends guests' perspectives with his own experiences about how to run 1:1s that actually matter.

One-on-ones aren't forecast calls. Jeff's line was blunt: 1:1 is not place to review pipeline or go through Jira tickets. That's management not leadership. If your 1:1 is just status update you're missing the point. Instead goal is to create predictable space where your team member feels heard, supported, and stretched. Separate the two conversations. Every good 1:1 has two streams: business (how's work going? where are you blocked?) and growth (how are you going? what skills do you want to build?). Mix them together and you'll default to easy stuff (tasks and deadlines) while avoiding harder more valuable growth discussions.

Coach vs mentor mode. Ross drew clean line: mentor shares your lived experience (here's what worked for me and why), coach holds back your opinion (what outcome do you want? what options do you see?). Trick is knowing which mode to choose. Repeatable patterns call for mentor. Fuzzy goals or messy context call for coach. Quality of your 1:1s is quality of your questions. Some that work: trust and connection (what's one thing outside of work that's giving you energy or draining it?), performance (where are you blocked?), growth (which of your strengths are you using most right now? any blind spots showing up?), team health (what's one thing we could improve in how team works together?).

Create variety. Context shapes conversation. Jeff swears by walking 1:1 (fewer distractions, more openness). Sometimes you'll want cafe chat, sometimes structured Zoom. Important part is consistency: show up every time. When things get hard (performance dips, egos flare, mistakes happen) good 1:1 is where you surface it early: be direct but empathetic (I've noticed X, how do you see it?), admit your own mistakes (modeling it makes it safe for others), if someone's struggling ask whether you're dealing with skills gap, motivation issue, or context clash. If you find yourself spending more energy working around someone than with them, you may be past point of recovery.

Watch for runways. Roles don't stay fit forever. Jeff talked about three-year rule: after three years in same seat passion can fade and autopilot sets in. Use your 1:1s to explore new runways (another project, team, or role) before things stall. Before you walk into next 1:1 run through checklist: did I check in on them as human first? did they bring their own topics? did I share context or feedback they need? did we talk about growth not just tasks? did I choose right hat (mentor or coach)? did we both leave with clear next steps? One-on-ones aren't glamorous. They don't make headlines. But in quiet rhythm of team they're where trust is built, blind spots surface, and growth plans take root. Jeff: people don't follow titles, they follow consistency.