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How to Manage Up As the First Employee

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Being the first hire at a startup can be an intimidating challenge. Here’s what I’ve learned through my experiences one how to managing up.

Note: This story was originally posted in The Goodbets Press on 10/1/2019

Being the first employee at any organization — especially at a startup — is a unique challenge. While startups, in general, tend to lack structure and processes, when you’re coming in as the first hire, there are even fewer systems in place. Your boss is probably used to steering the ship on their own, and much of the information about the org, and those processes to an extent, all live in their head. They’re not used to having to communicate with someone else and pull things out of their own head. These are just a few of the unique challenges you might face.

You have to be able to manage up as the first employee. Even if you have the world’s best boss, you’re going to be faced with challenges that require you to step up and lead the way.

I’ve been the first employee twice before — once at a startup incubator and now in my current job. Each experience has been an amazing learning opportunity and has also come with its own challenges. Here’s what I learned from both those experiences and some things that I still struggle with.

You need to be self-motivated

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I’ve found that in both roles, but especially at my current job, I set my own schedule and have to take the initiative. This can be a little paralyzing, especially since you’re new to an organization. If you’re already not inclined to be self-motivated or self-disciplined, this becomes really challenging.

What I’ve found to be helpful is to take complete ownership over set projects or tasks that will provide value to your company. This gives you a defined idea of what you’re responsible for and will allow you to create your own work as you breakdown that project or those tasks. Then, you can rest assured knowing that you’re doing something that is of value to your startup.

I also try to create high-level project breakdowns when tackling a new task or project and then breaking up those milestones in my daily to-do list. My bullet journal, Google Calendar, and Asana are the three most important tools that I use on a daily basis. Having this list helps me visualize what I want to accomplish for the day, and having a higher level breakdown is useful for keeping the bigger picture in mind when working on a project.

Think value first, and seek to understand

Sometimes I feel paralyzed when I sit down and think about what I should do for the day. I’m not sure what things are the highest priority and what things are important. To help loosen this paralysis, I try to approach things by how they tie to our value proposition and if those tasks are the best use of my time. There’s also an added aspect of urgency and importance in there — something might not create direct value for us, but could be an important and impending deadline that’s approaching.

By asking myself “Is this the best use of my time?”, I can think smarter about how I allocate my time and resources. If I don’t understand the underlying value or importance of my task, I’ll reach out to my boss to understand. As time has gone on, I’ve learned when to ask and when not to ask and am slowly gaining an understanding of our work at large. This is difficult to grasp when starting at an organization, but if you seek to understand through asking the right questions, you’ll get there.

You need to be okay without structure

This has been the biggest challenge I’ve found. When I came into the incubator, there was next to nothing. We had a grant proposal with outcomes, and nothing else. The director of the program was hired about a week before I was — we were both new. We took that and created a program backward from it, which is a process I would recommend.

When you’re entering a world without structure, things can seem very chaotic. You’ll be faced with challenges like how do we invoice? What do we do when this happens? What do we do with inquiries on our website? Who handles that? Your startup will probably have very few procedures in place. Sometimes this is really exciting — you get to build this organization from the ground up with your vision and that’s a rare opportunity. Other times though, it can be super frustrating. Have you tried navigating payroll when you don’t even have HR? It’s frustrating. This challenge comes with upsides and downsides — prepare yourself for both.

Overcommunication can be key

My boss and I check-in for five minutes at the beginning of each day. While we’re a remote team, I’ve found that having regular check-ins is really helpful for aligning and getting on the same page. Even if it’s a longer check-in on a weekly or monthly basis, it’s a well-deserved opportunity to align with one another. It’s something that I didn’t do when I worked at the incubator, and in hindsight wish I had pushed for.

Dedicate a consistent time interval to have one-on-ones with each other, and make sure you’re aligned with the goals of your work. This will help you both stay connected to the core value proposition of what you’re doing and will help you both feel grounded. Plus, it gives you an opportunity to share out what you’ve been working on.

Strive to create systems and processes

Whenever you do something for the first time, write it down. It may sound silly at first because you’re probably the only person that needs to know, but this is important for growth. As the first hire, you’ll be setting the precedent for those to come and laying the foundation for your startup’s processes moving forward. Record these as often as you can. It’ll make your job easier and make future growth more accessible.

When I considered leaving my last job at a startup, I realized that I had created the entire process for one of our organization’s core products. This thing lived 100% in my head. I made sure I took the time to document everything and get it out of my head before I left the company. This also helped me do things like go on vacation without getting phone calls from my boss and coworker. It also helped the company move on without me and kept me safe from burnt bridges.

Struggles of being the first employee

With these opportunities have come with a lot of benefits, they came with their own struggles too. I still struggle with how to manage up in my own role, and what that means. Some days I feel like I’m doing a great job, I’m motivated, and I’m on the right track. Other days I don’t know how I should proceed and I feel like I’m spinning my wheels in the mud. I still struggle with staying self-motivated, especially on a remote team.

Maybe one day I’ll have the answers to these questions I still have.

All things considered, being the first employee at an organization had been a really valuable experience and one that I recommend. It’s something that forced me to grow rapidly and fit into new roles and experiences that I wouldn’t have otherwise been exposed to. With that comes several challenges, but nothing that you can’t handle.

Veronica Head