How I Earned My Bosses’ Trust as the Only Employee in the Company

Not having colleagues brought me closer to my bosses.

Alberto Romero
Apr 21 · 6 min read
Source: Mohamed Hassan in Pixabay

In January 2018, I got my first job at an AI startup that wanted to change the world. I was scared and excited. Three days after applying I was in. The process was so fast that my body didn’t have time to assimilate.

Soon I was told I was the only employee of the startup. We were seven total: five associates, the project manager, and me. Imposing. They were trying to build a real-time bidirectional sign language translator. It is as complex as it sounds.

For half a year, I worked hand-in-hand with them, as the only employee. Here’s how I earned my bosses’ trust by taking advantage of a unique situation.

The pseudo-colleague boss is the best.

When we think of going to the office we assume we’ll be surrounded by our colleagues. People that are neither above nor below us. Our equals. It gives us a sense of security. Or better, calmness.

We don’t feel observed. We do our jobs. We talk with our colleagues. We share some laughs. It’s only when our boss appears that we act 100% focused. At least that’s how I imagine a traditional office — I may be too biased by movies.

Anyway, it wasn’t like that for me.

Each morning I’d go into the office and, depending on the day, I found one of two scenarios: either I was alone (best days for sure) or I’d work with one of my bosses. Usually the latter.

However, I never felt pressured or judged. I felt comfortable being around people that were above me — although they were probably assessing my performance with the corner of their eyes. We interacted with each other daily and we built a sense of mutual trust that was difficult to lose.

The CTO and I became almost colleagues. We called each other many times a day. We were available out of schedule (I had other benefits in compensation). We worked on tasks together, sharing points of view and testing solutions. And we felt shared joy when we solved a problem we’d been working on for weeks.

I didn’t have actual colleagues but I didn’t have traditional bosses either. And that’s something I valued throughout my whole journey there.

When you think it’s enough, go one step further.

I did my first ever interview with them. In my not-so-humble opinion, I nailed it. Soon after it started, the seriousness mutated into friendly chatting. My boss-to-be even showed me the code they were working on and let me take a peek. I gave him my honest opinion. They were doing it completely wrong, although I didn’t use that exact words. I guess he liked my sincerity.

To top it off, I brought with me an article I had been working on for some time in which I discussed the impact of DeepMind’s AlphaGo Zero. I showed interest in AI. I showed initiative because I wrote an article. And I showed ambition because I managed to get published in a governmental engineering journal.

It took them only three days to accept me as the new employee.

But I wasn’t finished yet. This happened early in January 2018. My contract started in February. I had close to a month before being an official member of the company. What did I do? I offered my boss to help them with the problems they were having. I was working with him a month before I earned any money.

I showed a passion for the project. Showed a good attitude. Nailed the first impression. And leveraged the opportunities I had.

It all paid incredibly well in the long term.

A few little successes can help more than a single big one.

I was working with my boss in my pre-contract period when I found out one of the issues was very easily solvable. My boss had been working on it for some weeks already and didn’t know how to solve it.

The reason, as I realized soon, was that no one in the company had actual theoretical or practical AI knowledge. Not even my boss. They were “trying” things until something seemed to work.

Again, I leveraged the opportunity and, within two weeks, solved the problem. But instead of solving it at once, I divided it into chunks and solved them one by one. After each solution I’d show my boss how I did it, hiding its simplicity and emphasizing the results. In a display of “marketing” skills, I managed to earn a good name even before entering the company.

I’m not proud of this “tactic” but I don’t regret it. I had a door open in front of me and went through it. In the end, they got their problems solved. And I gained a good reputation — while working without earning money. It was a win-win situation.

It made my life for the next three years a lot easier. This experience taught me that sometimes money isn’t the most valuable gain. Two months afterward I convinced my boss that working full-time from home was a good idea. If he hadn’t trusted me, I’d have never managed to get it.

Well-based opinions are always valuable.

As the only person with AI knowledge, I was consulted most tech-related decisions. Every single time I was honest with what I thought. I didn’t hide my opinion just because it was against what everyone else thought.

I explained my view and tried to convey a sincere degree of reliability. If it was just a hunch I’d say it too. In the end, I was an “adviser.” I didn’t make decisions, so the pressure of responsibility wasn’t on me. Whatever they told me to do, I did. Other times I was wrong. Those times I didn’t try to make up for it. I acknowledged my mistake.

My bosses always thanked me for being honest instead of going with the flow. And I realized they valued my opinion to the point of changing directions depending on what I thought.

For instance, at first, we were trying to measure hand movement with an electronic bracelet to capture sign information. I explained it wouldn’t work and advised them to replace the bracelet with a normal camera. After deliberating, they accepted my proposition and we achieved more success in 1 month than in the previous 4 months.

When they listened to my opinion I felt an important part of the team and when things ended up getting better, they’d trust me even more.

Final Thoughts

I was in an easy position to earn trust from my bosses because I was the only employee. But these ideas can be applied to any situation.

  • Treat your boss as a colleague. A boss can be intimidating, but they are people too. They have a life beyond work, with their families, kids, and dogs. Try to create a closer bond, even if working hand in hand isn’t possible.
  • First impressions are key to build a nice relationship. It’s very difficult to reduce the effect of a bad first impression. Make sure, within the boundaries of being yourself, to show your interest, attitude, and initiative.
  • Leverage any accomplishment you make. Doing great things and having good results is useless if no one knows you did it. Make sure you get the appearances right. And get the best out of profitable situations.
  • Be real and honest with your opinions. But don’t fix them. Being flexible is as important as having well-based opinions. Follow the idea of “strong opinions, weakly held.”

Ascent Publication

Strive for happier.

Alberto Romero

Written by

Writing at the intersection of AI, philosophy, and the cognitive sciences | | Subscribe here:

Ascent Publication

Strive for happier. Join a community of storytellers documenting the climb to happiness and fulfillment.

Alberto Romero

Written by

Writing at the intersection of AI, philosophy, and the cognitive sciences | | Subscribe here:

Ascent Publication

Strive for happier. Join a community of storytellers documenting the climb to happiness and fulfillment.

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