An Open Letter to Entrepreneurs on Hiring Employees

An Open Letter to All Entrepreneurs Looking to Hire Their Next Employee

Ok, show of hands. Who else has made the mistake of hiring the wrong person and keeping that person on board, hoping they would turn it around?

Chances are, the person had an impressive resume.  If you hired them online, they got great reviews on Upwork. Or you were impressed that their portfolio was really impressive.

They also came with all kinds of great recommendations. The most respected people in your town or industry told you this person would be great for your company.

And within the first week, you knew it was a mistake.  But you hope against hope that the new employee is going to work out. But weeks go by, and the data suggests this is a lost cause.

If you’re like me, you must be thinking:  “What went wrong?”

Normally, this blog is reserved for fact based, how to posts, that will show you how to achieve a specific task to grow and scale your business.

However, because I see so many entrepreneurs make the same hiring mistakes over and over and over again…

I figured I’d take the first post of 2016 and write a letter to all of the entrepreneurs who are considering hiring employees or have made a hiring mistake.

Here goes:

Dear Entrepreneur,

Take a deep breath.

You’re not alone.  We’ve all done it.  Every. Single. One of us.

So I can tell you that this letter comes from personal experience.  I’m not writing this letter so that I can tell you “I told you so” in the future.

Instead, I want you to think of this more as a speed bump.  That as you enter the new year, you can look back and reflect.  Especially if a new hire went wrong.

Think of this letter as a reminder, so that you don’t make the same mistake again.

Talent is important, but it ain’t the only thing

Of course, you want to find a talented employee who will be able to do the absolute best job possible.

But when it comes to hiring success, talent isn’t the only thing.  Here’s a list of four other criteria that will determine the success (or failure) of your new employee.

Passion for Your Business

This also includes a passion for helping your customers.

The very first developer I hired for my marketing agency fit every credential that I needed.  He was a great developer, an excellent communicator, and well versed in the front end work that I needed him to do.

There was just one problem:  He HATED working in a client services business like a marketing agency.

His dream job was to work for a Silicon Valley startup.

In a vacuum, this isn’t a bad thing.  But the problem was his lack of passion for the business, and for our customers, reflected in his work.  The effort and results simply weren’t there.

I just know that if he actually liked our customers, liked the type of business he was in, then he would have gone the extra mile to produce the results up to his capabilities.

Culture fit

Sometimes you find a talented person, and they just don’t fit within your organization for some reason.

In my experience, companies tend to take on the personality of the CEO/founder/etc.

If your company is comprised of people who like to play pranks and have fun while they’re working their asses off, then you should avoid hiring someone who takes himself or herself extremely seriously.

There is absolutely nothing wrong with either of those personality traits, and both can be extremely successful, but in my experience, the clash in personalities will not lead to success.

Further, if you’re a company whose labor force is remote, then you need to find people who have an ability to take initiative and not wait for work to be handed to them every single day.

They will not succeed within the confines of the company you’ve created.

Eager to learn new things

As a small business owner or founder, you need to wear many hats.

To perform these duties, you’re going to have to learn new skills on a seemingly daily basis.  But not only will you have to learn new skills, your employees will have to as well.

Your software developer may need to learn how to create documentation.  Your content marketer may need to learn how to use Facebook ads.  Your customer service team member may need to learn basic programming skills to fix quick bugs.

Some employees will embrace these challenges. They will thrive on them and look at it as an opportunity to increase their skill set.

Other employees, when asked to learn a new skill, will throw their hands up and say “that’s not my job!”

The truth is, this is not the type of employee you want working for you. No matter how talented they are, the person who isn’t eager to learn new things isn’t going to succeed in your small business.

Domain expertise is a plus

I see this mistake so often, especially when it comes to hiring marketers.

Let’s say you’re in the business of selling accounting software and you want to hire someone to help you with your content marketing.

Most people would look for someone who has experience getting traffic to a blog and is a good writer.  But the problem is, most people don’t know a damn thing about accounting.

Sure, they can learn.  But that might take a long time and will cost you a lot of money.

It’s much easier to hire someone with accounting experience and teach them to write, than it is to hire a writer and teach them accounting.

Hire Slow…

Right now, I’m going to let you in on a secret.

I’m about to share with you step by step how Time Doctor hires a new employee.

After you create your job description, it’s time to start searching for the right candidates. This is what we call the hiring funnel process. You fill the top of the funnel with as many qualified candidates and weed them out little by little at each stage of the process.

At Time Doctor, we typically fill the funnel with at least 50 applicants and no more than 300. Yeah, it’s a lot of work. But remember, the title of this section is “Hire Slow”.  We get our candidates from employment websites like Upwork, as well as LinkedIn and referrals.

The next step is to filter out the qualified applicants from those that are unqualified. In most cases, we find that you can easily eliminate about 70% of the applicants based on poor quality English, a weak resume, or entry level experience.

Once you have determined the most qualified applicants, you provide each one with a test; each examination depends on the tasks of the job. The test can range between 15 minutes (unpaid) to as much as three hours (paid). At the end, you peruse the test, evaluate them and you are left with just a few prospects.

The final step is to perform a verbal interview over Skype or Google Hangouts, followed by a 10-hour paid trial period. It’s best to hire a couple of people for this paid trial period at the same time rather than opting for one.

Yeah, it’s a lot of work. But that’s exactly what I meant when I said, “Hire Slow”.

But Fire Quickly

It’s hard.

Firing someone can take an emotional toll on a business owner. And it never gets any easier. You know that you’re about to alter the livelihood of a person, and their family.

And when I suggest you “fire quickly”, I don’t ever want you to make light of the fact that someone is about to lose their job and the means by which they feed their children.

Yeah, it sucks.

I used to try to give people second, third, and fourth chances. Anything in order to avoid terminating their employment.

The sad truth is delaying the inevitable is a bad idea.

According to the Wall Street Journal, studies show that one bad employee in an otherwise high performing group can lead to a 30% decrease in productivity.

Employees who are unhappy tend to miss work more often than happier employees. They tend to spread their misery among the whole group and lower company morale.  And if they are customer facing employees, there lies the potential of your business losing business and revenue.

The truth is, it’s best not to hire bad employees in the first place (duh!).  But if by mistake you do hire someone who can’t get the job done, then it’s best for you, your good employees, and your business to fire them quickly.

Don’t let one bad experience scare you

When I started my company, i had visions of building an amazing team of people, who would do really cool work together.  And we would be like a family.

I had romantic visions in my head that this would happen overnight.

That everyone I hired would be the perfect employee and love coming to work every day.  Unfortunately, that didn’t happen for me.

And chances are, it didn’t happen for you either.

Otherwise, you wouldn’t have read this far.

But that’s OK.

Because now I know better. And so do you.

Let’s make a pact together. That the next time you go about hiring employees, you learn from your past mistakes…

And build the business you’ve dreamed about.

Have a great 2016!


Greg Digneo

Greg Digneo

Greg Digneo writes for, a time monitoring and productivity monitoring software designed for tracking hours and productivity of remote teams. If you would like to see where you and your team are spending your time during work, then try Time Doctor FREE for 14 days.


  • Todd Drayton says:

    Hiring slow is bullshit. If you want the best people, you need to get them FAST or someone else will hire them first. That’s why you need to speed up the screening and interview process. There are some tools that can help, depending on the position. For app development jobs you can use automated coding tests from TestDome:
    This way you can evaluate candidates skill level quickly and narrow down the selection pretty fast. Hire smart.

  • David Jensen says:

    Hey Greg, Great “open letter” and Time Doctor seems like an ingenious product to help businesses. Another straight forward approach to developing your own hiring system is found in The Naked Interview: Hiring Without Regret, which I wrote to help business owners learn to hire the right person the first time and every time. Here’s to your expansion & success.

  • The last two points are the most important. Hire slow and fire fast. If you want to improve your hiring success from 30% to nearly 80% then I highly recommend reading and adopting practices found in the book Topgrading by Brad Smart. It changed my career

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