Managing and working with startup employees is both exciting and tiring, often all at once. But after managing folks throughout my career, there's one email I love to create and send: The "first 100 days" email. Here's how it works.

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Why do this

Startups are busy, hectic places to work. Who has the time or foresight to think about this? You do, my friend. Think about the leaders you've admired. The ones that stood out. In most cases, they were the ones that remembered something unique to your situation. They met you where you're at. They listened. They cared.

Many startup employees feel imposter syndrome all of the time. Spending a few minutes here and there to track down some info is highly scalable for you and empowering for them.

Case in point: I've had 3 different direct reports willingly say that my "1st 100 days" emails led them to tears and/or they saved it for years to come.

This stuff matters. So how does it work? 

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Phase 1: Before you hire them

During the interview phase, keep track of what the yet-to-be hired employee wants to accomplish in their 1st 90 days. It could be a project, a team they want to connect with, anything tangible.

Phase 2: As they start

As you start to work together, keep track of the following items in 2 buckets: the professional stuff and the cultural stuff. Personally I kept track in Asana (as a separate task per direct report) but a simple draft email works too.

The Professional Stuff

1. The big goals they had for the 1st 90 days
2. The wins they already had(doesn't matter how small, list it down!)
3. Any OKRs they positively impacted
4. Any praise from their peers, their direct reports (if applicable), other leaders

The Cultural Stuff

1. The Slack emojis that they used the most (a scroll back a few days is usually enough to figure out their favorites) 
2. Your favorite of their memes/GIFs they send (this assumes you have a culture where humor is appreciated. If not, welp).
3. Any inside jokes you might have together

Phase 3: After 100 days

As they pass the 3 month mark, make sure you: 

1. Schedule a 90 day check-in (if you havent already)
2. Put together the email to be sent on Day 100 (Why 100? It sounds nicer than Day 90)
3. Schedule it to go out in the AM before they come online. Having it be the first thing they see that day can set a strong tone for the entire day and/or week.

Phase 4: After 101+ Days

What happens after, is really up to you (keep tracking for to make performance review discussions easier?). But if you think of a new way to craft these emails or a line item I missed, let me know (my Twitter DMs are open).

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Here's to your 1st 100 days and beyond.