Don't make me fire you

A letter to new hires at early-stage startups

You may not like this letter… but it’s not wrong.

Dear new employee,

I’m so excited to work with you! We have massive goals, a huge opportunity, and a motivated team coming together. I am trying to make this a career-defining opportunity for everyone on our team.

One thing you should know: Odds are I’ll probably fire you in the next 3-6 months.

I don’t want to do this. I’ll feel awful about it. Here’s why I’ll do it… and what you can do to avoid it. Please, please, PLEASE read this closely. I want you to succeed!

Why I’ll fire you.

I’m assuming we did a great job in hiring you, and that you’ll be a wonderful culture fit. I have confidence in your abilities and potential. Knowing all that, there are three reasons this job won’t work out:

1. Execution: You aren’t accomplishing the things you need to accomplish. (Disclaimer → it may not be clear to either of us what you need to accomplish, or what “great” looks like.)

2. Self-management: I feel I need to look over your shoulder and manage you. (Disclaimer → I may never give you this feedback.)

3. Direction: Even if you’re doing executing & self-managing, this might not be enough. We may hire over you or decide on a different direction. (Disclaimer → this will never be communicated well.)

I aspire to be able to give you this kind of feedback so you can change course. I aspire to include you in these decisions. But you need to understand my situation: I am trying to pull this business together, while fighting a million fires, and trying to be strategic, confident, and deliberate (and stay mostly sane).

What that means: I’m not going to be a good manager. If you’re new to startups, I’ll probably be the worst manager you’ve ever had.

I don’t want this to be true. I’ll try to be a good manager. But this is a startup. We’re in survival mode. I’m trying to juggle about 27 different jobs right now, and “being a good manager” is approximately priority #17. Wish it wasn’t the case, but it is.

I’ll miss or shorten our 1:1s (if we have them), I’ll have a difficult time answering Slack messages, I’ll be distracted when we talk… you get the picture.

You need to hear this now - knowing this sets you up to succeed in this job!

Here’s what I recommend doing to succeed despite my total managerial incompetence.

What you can do to avoid this.

You need to manage yourself, manage me, and avoid common failure behaviors.

On managing yourself:

Early-stage startups are chaos. There are a million things we could do; a thousand things we should do; and maybe four things we can do.

Which means you’re always going to have more on your plate than you can possibly handle. You’ll have tons of small fires burning at all times. Everything will feel important and urgent.

Startup employees make four mistakes that all come down to self-management:

1. You get paralyzed and accomplish nothing

2. You switch between a million tasks and accomplish nothing

3. You try to do everything and get burnt out

4. You accomplish unimportant things that don’t matter

You need to have a simple list of priorities that guides your calendar & effort.

When new fires emerge, you should add those to your list of priorities and compare them versus your priority list.

You should not try to multitask, and instead work your way down your list of priorities, executing each with urgency.

These are the basics, I know. But in the chaos and ambiguity of early-stage startups, the basics are wildly important.

On managing me:

My hair is on fire. My memory is selective. The only thing that matters to me is making this company survive, which means I’m obsessively focused on the company’s #1 bottleneck.

Which means:

• I will forget what I’ve told you (what you should be working on, your goals, etc.)

• I will forget what you’ve told me (what you’re working on, what you need from me, etc.)

• If your area is not the company’s #1 bottleneck, you will get less attention from me

Because of this, employees make a few critical mistakes:

1. You constantly change where you’re focused based on what I say

2. You stop communicating with me when my “eye of Sauron” isn’t on your scope of work

3. You don’t communicate in my language

Here’s the best way to communicate with an early-stage startup founder:

• Brief weekly or biweekly writeups on where you’re focused & why, what you’ve accomplished, and what challenges you face (aka: where I can help)

  • For current or future leaders: do an occasional “strategy” thought exercise: How can we 10x what’s working? What new ideas should we be testing? What’s the next thing we should be focused on, and how can we level up?

• Optional but very helpful - daily Slack updates on what you’re focused on & what you accomplished.

• When I come with new ideas, which I will always do, show me your priority stack and help me figure out where this new idea should slot in.

On failure behaviors

There are 5 failure behaviors I’ve seen among early-stage employees that aren’t covered above.

1. You never admit you’re wrong. When you’re wrong, admit you’re wrong. Because you will be wrong. A lot. Things will fail all the time. If you can’t admit you were wrong, or admit something didn’t work and it’s your fault… you’re not going to be able to succeed in a startup. The whole point is to be less wrong over time, and in order to do that, we need to understand why we were wrong in the first place.

2. You have a can’t-do attitude. If your first reaction is, “there’s no way this can be done,” you’re going to have a hard time at a startup. We need to be thinking about how we can 10x things, and what it would take to make XYZ happen… not shooting it down out of the gate. This doesn’t mean you need to be a “yes-person”, and you don’t have to be crazy, but you can’t be a pessimist either.

3. You’re a talker vs. a doer, and don’t get your hands dirty. I don’t care if you’re a VP… you have to get your hands dirty in a startup. There’s no work that’s beneath any of us. And in most cases, more talking won’t solve the problem. We need to go and do stuff in order to figure out the answer.

4. You focus on other people’s work when you aren’t crushing it. If you’re in sales but always trying to do product work, and you’re not hitting quota… or vice-versa… this won’t work. Nail your domain, collaborate, but if you don’t want to nail the main work we hired you to do… don’t take this job.

5. You cause (or don’t solve) people problems. I don’t have the time to play mediator or hall monitor. If you have a problem with someone on the team, go tell them and find a way to work together to fix it. If political problems fester, I will fix it via elimination.

All that unpleasantness behind us: I am so excited to work together. Let’s make something awesome.