Most Engineering Managers Wing Their 1:1s.

I managed my first engineering team for almost a year before I admitted something: I was winging every single 1:1.

Not intentionally. I’d open my calendar, see “1:1 with Sarah — 30 minutes,” and think: I’ll figure out what to talk about when we start. Sometimes I’d glance at Slack. Occasionally I’d remember something from last week’s standup. Most of the time, I’d open with “So… how’s it going?” and hope something useful came up.

It felt fine. Sarah seemed fine. Everyone seemed fine.

Then Sarah put in her notice. And in the exit interview, she said something that stuck with me: “I kept bringing up the issues, but it never felt like anything changed.”

I had heard her mention various problems here and there. I just hadn’t connected it to a pattern. I hadn’t connected anything to anything because I was walking into 1:1s with zero preparation and zero context and my notes were not great. Note takers help, but they are not easy to scan.

The Real Cost of Unprepped 1:1s

Here’s what I’ve learned since then: the cost of winging 1:1s isn’t that they go badly. It’s that they go okay. They’re pleasant. They cover surface-level updates. And you leave feeling like you did your job.

But you miss things:

You miss patterns. An engineer mentions being blocked on an API dependency on Monday. By Thursday’s 1:1, you’ve forgotten. They mention it again next week. You nod sympathetically. Three weeks later, they’re frustrated and you still haven’t escalated it. No single conversation was alarming, but the pattern was.

You miss sentiment shifts. Standups get shorter. Responses become formulaic. The engineer who used to share detailed updates starts writing “No blockers” every day. These shifts happen gradually. Without tracking them, you only notice when it’s too late.

You miss the career conversation. When you don’t prep, urgent topics eat your 30 minutes. That goal review you meant to bring up? Pushed to next week. The growth conversation? Next quarter. Before you know it, your report’s career development hasn’t been discussed in four months.

You miss the signal in the noise. An engineer shipped three PRs this week, closed two tickets, and updated their goal. That sounds productive. But one of those PRs has been in review for six days with no reviewer assigned. They’re quietly stuck and not asking for help. You’d never know from a standup summary alone.

What “Prep” Actually Looks Like

When I say “prep,” I don’t mean spending 30 minutes reading Jira tickets before each 1:1. Nobody has time for that, especially if you’re managing six to eight engineers.

Good 1:1 prep answers three questions in under 60 seconds:

1. What should I definitely bring up? Overdue action items, at-risk goals, active signals like sentiment drops or repeated blockers.

2. What’s the context? What have they shipped recently? What have they been stuck on? What came up in their last standup?

3. What did we say last time? Follow-ups from the previous 1:1 that I need to close the loop on.

That’s it. Three questions. The problem is that answering them requires pulling data from five or six different places: your standup tool, your project tracker, your notes app, your memory. By the time you’ve assembled that picture, the 1:1 is half over.

The Tools Don’t Help (Yet)

Most 1:1 tools, Fellow, Lattice, 15Five give you a shared agenda. A blank document where you and your report can add topics before the meeting. That’s fine. It’s better than nothing. But it solves the wrong problem.

The problem isn’t that there’s no place to write what you want to discuss. The problem is that you don’t know what you should discuss. You need someone (or something) to look at the data and tell you: “Sarah’s been blocked on the same thing for four days. James hasn’t updated his goal in two weeks. Alex’s standup sentiment has been declining.”

A blank shared agenda doesn’t do that. It just gives you a nicer place to wing it.

What Actually Changed for Me

I started building structured prep into my workflow about a year ago. At first, it was manual: I’d spend 5 minutes before each 1:1 checking standups, Jira, and my own notes. Even that basic habit made a noticeable difference. I caught blockers faster. I followed up on action items. Engineers started saying things like “Oh, you actually remembered that.”

That’s a low bar, but it mattered.

The tool I landed on was Vereda AI, which generates what it calls a “prep brief” before each 1:1. The brief pulls from standups, GitHub/Jira/Linear activity, goal progress, risk analysis, and previous check-in data. It surfaces talking points prioritized by urgency: critical signals first including sentiment, overdue items, blockers, and career development.

What I like about it is that I’m not reading a dashboard, I’m getting a prioritized list of “here’s what to talk about and why.” It takes about 30 seconds to scan before a 1:1. The engineer doesn’t see the prep brief — it’s manager-facing so there’s no “being evaluated” dynamic in the room, it guides the conversation.

The Principles Behind Good 1:1 Prep

Whether you use a tool or build a manual habit, the principles are the same:

Prep should be fast. If it takes longer than 2 minutes per report, you won’t do it consistently. The prep needs to be a glance, not a research project.

Prep should surface what you’d miss. The value isn’t confirming what you already know. It’s catching the things you’d overlook: the stalled goal, the third time someone mentioned the same blocker, the engineer whose standup tone shifted.

Prep should include what you said you’d do. Half the value of 1:1s is follow-through. If you committed to escalating something, checking on a promotion timeline, or unblocking a dependency — your prep should remind you.

Prep should not be surveillance. This is important. The goal isn’t to walk in armed with evidence. It’s to walk in informed. There’s a difference between “I noticed your PRs have been sitting in review — what can I do to help?” and “I’ve been tracking your PR merge times.” The first is supportive. The second is creepy.

Career development should be a default topic. If you don’t prep, career conversations get pushed out by urgent issues. Good prep systems include a “career development” talking point by default so it doesn’t get lost.

A Simple Framework You Can Start Today

If you manage engineers and you’re not prepping for 1:1s, here’s a framework you can start this week with zero tools:

Before each 1:1, spend 2 minutes answering:

1. Check their last 3–5 standup responses. Anything concerning? Any repeated blockers?

2. Check their active goals or current sprint. Any stalled? Any at risk?

3. Check your notes from the last 1:1. Any follow-ups you promised?

4. When was the last time you discussed career growth?

Write down 2–3 things you want to bring up. That’s your prep.

If you want to go further, tools like Vereda AI automate this by aggregating standup data, project activity, and signals into a prep brief. But even the manual version is a massive improvement over walking in cold.

The Difference It Makes

Since I started prepping consistently, three things changed:

1. Blockers get resolved faster. I catch them in the first week, not the third.

2. Engineers trust the 1:1 more. When you remember what they told you and follow up, they start bringing real issues instead of surface updates.

3. I have evidence at review time. Months of 1:1 context beats two weeks of recency bias every time.

The irony is that prepping takes less total time than not prepping. Unprepped 1:1s meander, go long, and produce vague action items. Prepped 1:1s are focused, finish on time, and generate specific follow-ups.

Your engineers deserve more than “So… how’s it going?” They deserve a manager who walks in knowing what matters.

Amy Wightman is the co-founder of Vereda AI, an AI-powered performance management platform for engineering managers. She writes about engineering management, team health, and the tools that make both easier.