Dear SaaStr: I Want to Keep Doing 1-on-1s With My VPs, But How Do I Streamline Them?
1-on-1s may be partially out of fashion, but most CEOs I work with still do at least some of them. 93% of you still do them too. And I still find them a very useful management tool myself.
You shouldn’t necessarily streamline 1:1s across the board—some of them are critical and should stay as they are. But as you scale, your time is your most valuable asset, and you’ve got to ruthlessly prioritize where it’s spent. If your 1:1s are eating up too much of your week, it’s worth asking: are all of them driving enough value? Or are some just “nice to have”?
Not every 1:1 needs to be an hour-long deep dive. Some can be shorter, more focused, and still deliver the same value.
So segment them:
1. Top Performers: These folks don’t need you micromanaging them.
They need you to have their back and help them with the tough stuff they can’t solve alone. For them, a quick 15-20 minute check-in might be all it takes to keep them aligned and supported. Still do one every week, but also give them the freedom to pass on 1 out of 4 if they want to.
2. Stretch VPs or New Hires: These are the people who need more of your time.
If someone’s new to the role or struggling in certain areas, keep their 1:1s longer and more frequent. This is where you can really move the needle by helping them level up. Stick to longer, more structured sessions here until they become … a top performer.
3. Agenda-Free vs. Structured:
Some 1:1s are better when they’re unstructured—just a chance for your team to vent, share concerns, or brainstorm. Others, like deal reviews or sparring sessions, need a clear agenda to stay productive. Be intentional about which format works best for each person or topic.
If you’re still feeling stretched:
- Batch Your 1:1s: Group them back-to-back on specific days. This minimizes context-switching and frees up larger blocks of time for deep work or strategic thinking
- Delegate Where Possible: If you’re doing 1:1s with people who could report to someone else (e.g., a VP or Director), consider shifting those relationships. Your time should be spent with your leadership team, not two levels down.
- Protect Deep Work Time: Block 2-3 hours a few times a week for focused, strategic work. This is where you’ll figure out how to scale from $5M to $10M ARR.
Make sure your 1:1s are optimized for impact. Not to check a box.
Each one actually can be quite different. And that’s OK.
