Illustration of a grid with 5 faces and an empty space waiting for one more face

When a new employee joins a team, it’s the perfect time to set the table for what’s about to come, even years in the future. That weird knife and tiny fork? You’ll need those tools later. The beautifully folded napkin? You’ll be using it to clean up the mess you’re certain you’ll never make. (Welcome to the land of annoying metaphors.) And a letter welcoming your new hire is a great way to go about this.

It took me roughly ten years of managerising to figure out how powerful table-setting can be. Unfortunately, for the first several years, I squandered this opportunity. My intent was always to welcome and inspire my new team member, but I’d ruin it by telling them a bunch of boring stuff they already knew: where the coffee machine is, the fact that they’ll be filling out some paperwork on their first da- zzzzzzzzzzz… Oh. Sorry. Kinda fell asleep there.

Seriously, though: you want your new employee to be excited on their first day. Given that they were probably envisioning spending their first day in an office that isn’t also their home, this takes a little extra effort right now. And for their part, they want to know more about what you’ll expect of them. A good welcome letter can both calm their first-day jitters and inspire them to do the best work of their lives. Here’s the template I’ve developed over the years, along with the rationale behind each point.

Dear <name>,

Welcome to the team! I’m so excited you’ll be joining us. While your desk, laptop, etc. are being prepared, I want to share a few thoughts for you to keep in mind as you get ready for your first day here.

We believe in you and know you’ll do great things. We don’t hire anyone we don’t think is going to have a massive positive impact on the team and the company as a whole. I hope you feel proud of that. That also means our expectations of you are high, and yours should be too. But don’t worry: we’ll invest in your growth and equip you with the tools to do your best work.

Rationale

Besides being true (I would never say it if it wasn’t), the goal is to set the bar high and give new employees the confidence to reach for it. Once this has been acknowledged, the question “Is this the best work of your life?” can be used to challenge and inspire. Similarly, “That’s exactly why we hired you!” can be used to recognize outstanding performance.

You’re unique, and that’s important. Don’t hide the things that make you you – take advantage of them. You have different skills, different knowledge, a different background. The way you think about problems shouldn’t constrain you, it should fill in the gaps we don’t even know we have.

Rationale

There’s a ton of research out there showing that teams with diverse perspectives and experiences produce better results. If, that is, team members don’t feel pressured to downplay the things that make them unique.

You were hired to make changes. Don’t be afraid to challenge the status quo. Ask “why?” a lot. The fact that we’ve always done it that way is the worst possible reason to keep doing it that way. Use your unique talents and experience to suggest improvements and make them real.

Rationale

This not only makes the new hire feel safe questioning the status quo, but it also sets that up as something we expect of them. Continuous improvement is especially important as companies grow and face challenges around scaling. What got us here won’t get us there.

We’re going to disagree. And that’s a good thing! Respectful dissent is a gift. In fact, if we ever stop disagreeing, that should set off alarm bells. Constructive critique and debate are how we grow. They help us make better decisions. Your teammates and I are excited to hear your views.

Rationale

Being a passionate person myself, I tend to hire people who are as excited about their work as I am. However, when you combine passion with humanity’s general aversion to conflict, resentment can build up and that’s a recipe for disaster. Plus, having agreed that disagreement is nothing to fear, we can remind ourselves of that mid-disagreement. It makes me so happy when my own team uses this to manage up: “Hey Dan, you know we’re not required to agree, right?”

How to write the perfect 90-day plan

Everything involves trade-offs. There’s no process that doesn’t have a price. No task that doesn’t have an opportunity cost. If we let the quest for perfection get in the way of making incremental improvements, we’ll stall out and, ultimately, fail. With each new project, let’s make sure we agree on what we optimize for, versus where we can be flexible.

Rationale

We security folks are genetically predisposed toward absolutism. We like to point out the flaws in a solution and proclaim there’s no way it’ll work. I suspect this tendency exists on all teams to some extent. It’s an easy trap to fall into, after all – especially when the goal is to do right by the customer. Getting comfortable with trade-offs means we can have more sophisticated, nuanced conversations about what to solve now and what to leave for later.

You won’t like all my decisions. Remember how I said we’ll disagree? Sometimes I’ll make decisions you don’t like. Other times, the team will make decisions I don’t like. When that happens we’ll need to agree to disagree and commit to making the decision as successful as possible. Regardless, you should always understand why a decision was made. If you don’t, don’t be afraid to ask more questions.

Rationale

With all this disagreement and trading-off going on, there has to be a way to remain productive. Explicitly asking, “Should we disagree and commit?” can halt unproductive discussions and put the focus on moving forward. The danger with this approach is it can become a crutch, and unique viewpoints aren’t truly heard. Two questions that can help avoid this are, “Do you feel like you’ve been heard?”, and “Do you understand why?”

I’m not here to punish you. You’re going to make mistakes. I promise I will, too! The only reason your mistakes will upset me is if you don’t take ownership and learn from them. You are empowered to take calculated risks, and I will happily back you up on them, even when things don’t go the way you thought they would. Your failures are my failures, but your successes are always your own.

Rationale

Plenty has been written about how psychological safety impacts engagement, innovation, and general performance. I’ve found that by explicitly calling this out and making good on this promise when $#!t hits the fan, people are more likely to act on their ideas and take a candid look at the situation when things go wrong.

All these things I expect of you, you should expect of me. If ever you catch me not practicing what I preach, call it out. The expectations are the same across the team. Hold me accountable just as I hold you accountable. I’m not going to be an effective leader and our team is not going to follow me unless I’m setting the standard.

Rationale

Aside from simply being fair play, holding myself to the same standard I hold my team to makes us stronger as a group. If WWII movies have taught me anything, it’s that people give more and perform better when their leaders are right there on the front lines with them.


Sure, you could lay everything out during a conversation on their first day. But a letter has some advantages. It gives you time to collect your thoughts and make sure you’re expressing them the way you want to. Plus, a conversation would need to wait until their first day – when they also have administrative paperwork and introductions to think about – whereas a letter can be sent in advance so they can absorb everything with a clear head.

So next time you’re welcoming a new team member, give this whole letter thing a try. And don’t make the same mistakes I used to. Make yours count.

Onboard from anywhere with this inspiring new hire...