Below, find some stream of conscious ideas on good 1-1s.

Smarter folks than I have written on this: Andy Grove, Rands

Good One on Ones.

1-1s are critical. They’re a really good way to make sure that blockers aren’t shutting something down, to develop rapport and trust, to elicit help, and to avoid surprises and “getting out of sync.” They’re also just a nice way to make sure we don’t get into our own execution tracks and drift apart from each other.I wanted to share some ideas on how we make the most of them.

One-on-ones are the subordinate’s meeting.

You own them. They fail if you don’t prep for them. Make (and preferably share) an agenda the day before. Review it an hour (and definitely share!) before the meeting.

1-1s go way better when you come in with the issues in mind that you want to talk about. And even better when they are in order of import and/or you share an agenda so we know which issues to allocate more/less time to (i.e. don’t let us spend 45 min on X, when Y is actually more important to you).

Generally you want to discuss things in this priority:

  • Urgent, Strategic
    • e.g. [“One of my key employees is flailing and I’m not sure how to help them; We’re about to screw up something really big; We just screwed up something really big; I feel like I’m failing and am considering quitting, etc.”]
    • This might be scary to talk about, but prioritizing these well and calling attention to them early can often be “save the day” moment
    • Companies are saved through these urgent calls to action, people are able to keep jobs they otherwise would have lost, etc. <— this is where the good work happens
    • As a leader or early member of any company, I guarantee there will be at least one time where you raising one of these early will be the difference between the company being successful and failing
  • Urgent, Tactical
    • e.g. [“I need you to convince this person of X; we need to submit this ASAP; I’m underwater and need you to pick up Y for me; I need you to sign this; I’m blocked by Z — please help me get unblocked; etc.”]
    • Ideally, these should all be handled outside of this 1-1 time, but if we don’t have the time to get something done the right way, we at least have this hour as a safety valve
  • Strategic, Not urgent
    • e.g. [places the org can/should go; personal and career development goals; big/important ideas; ways to expand our products or service; etc.]
    • The best one-on-ones are often when we get to spend 1/3 to ¼th of our meetings touching on these issues. It means the org is humming very nicely and there aren’t many problems when we can talk about stuff like this
    • We won’t get to these in every meeting, if we’re lucky enough to have one meeting a month at this stage where the first two are totally handled, we’re in a good place
  • Tactical, Not urgent
    • If we ever have time for these things, we should often just end the meeting early
    • The one-on-ones that fail worst are the ones that spend their time on these because they are “top of mind” — it’s almost always an indication of bad planning.

Action items and follow-up

We both need to hold each other accountable for action items. Tracking notes and action items week-over-week is important for this to feel like progress and for there to be continuity to what we discuss.

Good 1-1s follow a flow from week-to-week more weeks than not, but not every week. When a crisis hits, it clearly should interrupt the flow of what you’re focused on. But, if you’re having a crisis every week — that’s an indication that you’re struggling with your responsibilities and that we should both look for ways to help you with that.

You should have some breakthrough or crisis pretty frequently in the early days, but it’s probably every 2-3 weeks, not every week. A major exception for that is if they are breakthroughs more than crises. If you can meaningfully improve what you’re working on every week, that’s obviously a good thing.

Label items on the agenda with what you actually want from it.

One of the funny things about one-on-ones, is that most managers (myself included) regularly suck at listening. We end up misreading the context that you're sharing something in. For example, we might think you’re asking for help when you’re only asking for an emotional outlet on some annoying issue that you easily know how to solve. Or, we think you’re just giving us an update when you actually need help solving something.

I find there are usually one of four categories that most agenda items fit into. Adding these to the agenda item makes sure your manager knows what you want them to be doing in each section.

  • Update: "Hey, I’m doing or did X and you should know about it. Especially important on material decisions you don’t need approval for but that you don’t want people surprised by later."
  • Escalation: "I’ve done X and Y, but I can’t get Z to happen. I need you to unblock me or fix this. I think the best way for you to do that is A, but B or C may also work."
  • Vent: "No action is needed, I just want to express how annoyed I am at Blah."
  • Decision: You need signoff for something. Always present it in this fashion: "I/We have X problem. I think there are Y and Z solutions. I recommend we do Y because A, B, and C.”

On that last one, you may be asking, “Why that stupid draconian format?” Great question! The way you know someone is ready for a promotion is when the organization (as personified by that person’s manager) starts agreeing with their recommendations on increasingly complex issues. So, by using that format, it’s easy to see when someone is [1] seeing all the options and [2] picking the “right” one — as determined by that boss and that company’s culture.

Note that that goes both ways. If a subordinate consistently disagrees with their manager’s decision making they can, should, and will leave the company. This could be caused by an honest misalignment on a vision, it could be an indication that this company’s culture isn’t for you, or it could be a warning sign that the manager is making bad decisions and needs to either grow or be replaced. If this is happening to you and your manager is otherwise good (kind, rational, etc.), talk with them about it. If your manager is not good, talk to their boss or HR, try to switch teams, or look for a new job. Life is too short to work with a company/manager who you don't respect.

With some frequency (especially when folks are recently in a new or expanded role) the manager will disagree with the recommendation made and should explain why. If the employee doesn’t agree, they should push back. As a manager do not shut those discussions down. Have them, even if it’s time consuming. It will improve the performance of your team. It could alert you to when you have issues with someone’s decision making. And, most importantly, it will give you early signals on your own failings and performance issues so you can fix your errors before you get replaced.

Some commitments from my end:

  • I will take notes and be present.
  • I may occasionally add something that I care about to the agenda, but I will do so after we address the things that you care about. This is your time, if I need more time to address my concerns, I can book a different slot with you.
  • If I wasn’t able to do it in the moment, I will deliver any feedback I have for you in this meeting — that way my feedback is always w/in a week of something happening and I have a venue to do it when it might have been inappropriate in the moment (if we are with another person, for example).

Status updates make 1-1s better.

The more time that we spend talking about things in the “Strategic, but not-urgent” bucket, the more we’re getting to focus on the really fun and really important things. To get to those, we have to get through the urgent stuff first. That is hard, but it’s made easier by handling those issues asynchronously. Update emails are great for briefing, sharing info, making sure someone is up-to-speed. Asynch updates can also help with other issues — if someone understands the context for something, it may be 5 minutes in a 1-1, instead of an hour.

Note: This can be overdone. Spend at least 50x more time working than you do sharing what you’re working on. But, 30-60min of asynchronous communication a week could easily be what enables us to have great 1-1s.

We should both be 100% candid and honest.

We’ll probably talk about concerns, fears, annoyances, hard emotions. We also may talk about personal struggles and what impact that may have on work and challenges coming up. Personal goals/desires. All of that.

This is an open and human moment, and it’s a safe 1-on-1 space for that. Think about what you want and need me to know so that this isn’t unstructured or unproductive, but don’t shy away from tough topics or discussions.