This is the blog of Adam Kalsey. Unusual depth and complexity. Rich, full body with a hint of nutty earthiness.

Management & Leadership

One on One Meetings - a collection of posts about 1:1s

I’ve been blogging a lot recently about holding 1:1 meetings with your reports. Here’s the entire collection of these works.

One on One meetings for managers
A one on one meeting is one of the top ways you can build your managerial leverage
One on One meetings: Frequency and Duration
How long should your 1:1s be? How often should you run them?
Do you need a 1:1 if you’re regularly communicating with your team?
You’re simply not having deep meaningful conversation about the process of work in hallway conversations or in your chat apps.
What should you talk about in a 1:1?
Who sets the agenda? What should you discuss, and what should you avoid discussing?
What agenda items should a manager bring to a 1:1?
At least 80% of a 1:1 agenda should be driven by your report, but if you also to use this time to work on things with them, then you’ll have better meetings.
Handling "I don’t have anything to talk about" in your 1:1s
When someone says they have nothing to discuss, they’re almost always thinking too narrowly.
Are 1:1s confidential?
Is the discussion that occurs in a 1:1 confidential, even if no agreed in the meeting to keep it so?
Skip-level 1:1s are your hidden superpower
Holding 1:1s with peers and with people far below you on the reporting chain will open your eyes up to what’s really going on in your business.
Encouraging 1:1s from other managers in your organization
If you’re managing other managers, encourage them to hold their own 1:1s. It’s such an important tool for managing and leading that everyone needs to be holding them.

Recently Written

Your OKR Cascade is Breaking Your Strategy
Aug 1: Most companies cascade OKRs down their org chart thinking it creates alignment. Instead, it fragments strategy and marginalizes supporting teams. Here's what works better than the waterfall approach.
Your Prioritization Problem Is a Strategy Problem
Jul 23: Most teams struggle with prioritization because they're trying to optimize for everything at once. The real problem isn't having too many options—it's not having a clear strategy to choose between them. Without strategy, every decision feels equally important. With strategy, most decisions become obvious.
Behind schedule
Jul 21: Your team is 6 weeks late and still missing features. The solution isn't working harder—it's accepting that your deadlines were fake all along. Ship what you have. Cut ruthlessly. Stop letting "one more day" turn into one more month.
VC’s Future Lies In Building Winners
Jun 21: AI and megafunds are about to kill the traditional venture model, forcing smaller VCs to stop hunting for hidden gems and start rolling up their sleeves to fix broken companies instead.
Should individual people have OKRs?
May 14: A good OKR describes and measures an outcome, but it can be challenging to create an outcome-focused OKR for an individual.
10 OKR traps and how to avoid them
May 8: I’ve helped lots of teams implement OKRs or fix a broken OKR process. Here are the 10 most common problems I see, and what to do instead.
AI is Smart, But Wisdom Requires Judgement
May 3: AI can process data at lightning speed, but wisdom comes from human judgment—picking the best imperfect option when facts alone don’t point the way.
Decoding Product Leadership Titles
Mar 18: Not all product leadership titles mean what they sound like. ‘Head of Product’ can mean anything from a senior PM to a true VP. Here’s how to tell the difference.

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