How to Implement Effective 1:1s

I've found that founders typically implement weekly 1:1s with the non-founders on their team when their headcount starts to approach ~7-12. When startups are this size, founders begin to feel like it's not as easy as it once was to keep everyone aligned and on-track. Founders (especially CEOs) may feel uncomfortable, anxious, or confused about how to get everyone on the same page - which are the emotional triggers that point to it being the right time to start doing 1:1s in addition to the meetings that take place as part of your dev cycle.

In my experience, founders running startups this size (up to a headcount in about the high teens although there are always exceptions) meet with their direct reports weekly, and meet with the other folks on their team biweekly or monthly (these are called skip-levels).

Here's how to launch and run your 1:1s effectively without getting too process-heavy.

First, read this blog post. It describes the goal of 1:1s and includes a great list of sample questions: https://medium.com/swlh/one-on-ones-are-my-most-valuable-meetings-heres-how-i-run-them-d9ae7c64dade

Second, send an email to your direct reports announcing the new/revised 1:1 structure. Whenever you’re changing a process that affects your team, you want to proactively communicate this to your team (like how you’d tell your users about a change to their plan - you always want to set the right expectation).

Below is a sample email one of my clients sent that you can adjust using your own voice. You’ll notice that it includes a link to the 1:1 agenda in a separate shared doc, and that it requests status updates be sent via email a day in advance to keep the actual meeting about bigger questions and joint problem-solving:

Subject: New 1:1 Structure

Body:

Hi team,

It is the start of an exciting summer of growth at COMPANY and we are looking to level up the company and improve communications across the board. I wanted to revisit how my team does 1:1s to add some structure to the process, improve our flow, and help you achieve your objectives.

I'm scheduling my 1:1s on Mondays as much as possible, and maintaining a shared gdoc to track our discussions. If we have to reschedule for any reason (usually my fault), please ping ADMIN/EA/ME to get our meeting back on my calendar.

These meetings are your time. Instead of a status update, which we should keep to email, we’ll use this time to dig into problems and opportunities. Once a month, the 1:1 will focus on your personal development and higher-level questions.

Your action items:

~24 hours before we meet, email me some quick bullet points in response to the 5 questions noted in the document below. This is your status update.Prepare for our 1:1 by reviewing the list of questions and noting in our doc any issues we can dig into. Feel free to choose a few questions from the ‘optional’ question set that we’ll cover if we have time - or come up with your own topics for us to discuss.

[[YOUR NAME]'s 1:1's](link to a meeting agenda you create. A sample agenda is below \/)

Third and finally, modify, maintain, and share the agenda for each of your 1:1s. Here’s a sample that one of my clients had success with:

SAMPLE 1:1 AGENDA:

I’m here to help you make sure:

- you have clear objectives, aligned with the company goals.

- you have the right information and resources to achieve those objectives.

- the rest of the company understands what you're working on.

Weekly Question Set:

1. What was accomplished last week?

2. What are you trying to get done this week?

3. What's in your way? Any problems are you facing? Any questions?

4. What feedback do you have for me - positive or constructive?

5. Here’s one piece of feedback (positive or constructive) I have for you:

Monthly Question Set:

In the past month, what have you been happy about?

In the past month, what have you been less happy about?

Any questions for me?

Optional Question Set: 

(direct report chooses 1-3 questions to answer, time allowing, or can ask/answer a question they formulate themselves: 

How do you feel about your goals for this quarter?

Any feedback for me?

How could I be a better manager for you?

What can I do to make your professional life better?

Pro tip: I recommend you drop the agenda you create for your 1:1s into the 'notes' section of your 1:1 calendar invites so both you and your direct report have the doc handy 24/7 in an easily-accessible place.

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