Hiring Your First Employee: A Step By Step Guide

For months, you have sustained a death-march pace working 12-16 hours a day doing everything it takes to keep your business afloat.

But now, you have finally reached that milestone where you can actually afford to make that first hire and take your startup to greater heights.


This is a good thing.

The problem?

You are about to take a leap of faith and either end up with a nightmare scenario or a get immense relief from hiring the right person.

Not to fret. In this post, I am going to walk you step-by-step through the basics of bringing onboard your first startup employee so you can propel your business (or I will send you a goldfish!).

Make Sure You Are Ready

Now that your startup has taken off and you have become your own boss, the question is: are you ready to become someone else‘s boss?

You know, the reason I am asking is because hiring help too early can be an issue. In fact, this could put your entire business at risk due to cash flow problems.

why startups fail

True, at this point, you might have a lot of customers, but that does not mean you have enough cash flow to make your first hire.


Because when a new person joins, you will have to cut a paycheck every month no matter if the customers are paying you or not.

What is more, there are hidden costs involved in hiring such as the cost of placing job offerings, buying new equipment, furnishings, etc.

So do not automatically assume you are ready to hire your first employee. Take your time and consider all costs together before pulling the trigger.

Go for Personality. Train for Ability.

Let us assume you are ready to hire someone for long-term work to expand your business.

Making that first hire is like falling in love. You are pumped and clueless how this is going to turn out.

Now, what you do know is that you probably want to hire someone who is a rockstar with a ton of skill.

First, the bad news.

There is a worldwide shortage of great talents.

skill shortage

Worse, as a startup, you cannot compete with mature companies that can offer a lot: an established product-market fit coupled with a long financial history.

Now, onto the good news.

Your prospective hires are going to be motivated by the high-risk, high-reward opportunities and a chance to make their contribution to the company’s core.

And that brings us to looking for talent that would buy into your dream and be a great fit (as opposed to qualifications) for your startup culture — AKA values-driven hiring.


Because you can always train a person to do their job, but it is a lot more difficult — if not impossible — to make them align with your startup vision and core values.

Need proof?

SurveyMonkey, a company that generates $100 million in profit, does not hire seasoned professionals. They zero in on recruiting people that would make a great cultural fit turning them into homegrown talent.

Bottom line — go for potential over attributes and track record.

Vet Your First Hire

So far so good.

You have decided to venture into values-driven hiring and already posted a job offer online dripping with your company values.

In your current stage, chances are, you do not have a strong brand, which drives massive numbers of candidates making recruiting a breeze.

But that is OK because you only need a single hire.

And when that first solid candidate successfully passes an initial screen for your specific attributes, you need to invite them over for an interview and evaluate them.

You want to unpack their past work experiences to get more in-depth on fit — how they align with your startup vision and core values, what drives their behaviours at work, and their ambition.

Here are a few interview questions you can ask to evaluate your candidate.

What accomplishment are you the most proud of professionally? It is essential to know what drives the candidate. Some people are motivated by money whereas others by impact. The answer to this question will reveal the value system in the candidate. If you hear something along the lines of, In my previous job, I had a sales target no one thought I’d hit. But I did! — this is a good answer. A better answer, though, would be, I had this extremely tough challenge. I worked super hard and went above and beyond. In the end, I failed, but my team members and I looked back on it as an inspiring time. Neither of the answers is bad, but it surfaces what the source of pride is.

What was the biggest failure in your career? If the candidate has some work experience, they have inevitably had some missteps over the course of their career. If the person is not willing to be raw with you, this is usually not a good sign. Because talking about your own failures is a sensitive matter and it shows how transparent the candidate is willing to be.

When was a time you went above and beyond? If you want to probe the candidate’s management skills and whether they are willing to walk the extra mile to get the job done (which is crucial for a startup culture), this could be a good question to ask. If the person retells you their exact experience of doing something that went beyond their direct responsibilities, you are on the right track. On the other hand, if you get some fluffed up, generic response — that is a red flag.

Backchannel to Get 360 Degree Data

You are now on the homestretch.

You just interviewed your candidate, and you think they are the perfect fit for the role.

So should you hire them right away?

Consider this:

Airbnb spent 5 months hiring before they actually hired a person.

So before you make a job offer to your candidate and make that first hire, you want to have more data that prove that was the person said in the job interview was true.


Enter backchanneling.

Now, the idea behind backchanneling is not to dig for dirt. You just want to make sure that the candidate is a good cultural fit and that they have the aptitude to help your company grow.

Here are a few questions you can ask the candidate’s references.

How was this person seen by the other team members? This is just better than asking what the reference thinks of the person because it enables them to be more transparent to talk about the candidate and for you to audit their answer.

How would it make you feel if you had to work with the person again? More or less excited? This question puts the reference in the hiring shoes, which should help you get a more honest response.

Is there anything I did not ask that you would like me to know about the person? It gives the reference the green light to share whatever it is on their mind. I would recommend asking this question in the middle, as it can open up more conversations.

Keep in mind that we all have something we wish we had not done. All you want is to understand the spectrum from the bad to good.

Final Words

As a first-time business owner, it is nothing but easy to make your first hire. That is because you do not know what you are doing, which is OK.

Just accept that fact that if you were to evaluate a Sushi Chef with 3+ years of experience, you would say it is impossible hands down.

The good news is that you can get your rhythm with it and learn the process.

And when that happens, you will be able to grow your business at 10x speed.

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Hiring Your First Employee: A Step By Step Guide

by Max Woolf