How I overcame 4 specific mental barriers to hiring

Originally published on the Entrepreneurs in Motion podcast.

I’ve been in business for about seven years, and I’ve dragged my feet on hiring help — I’ve had no VAs and no employees. Sometimes I’d hire freelancers for temporary projects, but I hadn’t taken on anybody who was a regular part of operations and a consistent member of the team.

Instead, I streamlined my business, automated as much as possible, and batch produced things in order to keep the workload manageable for me. And that worked for quite a long time!

But the truth is I also had some mental resistance to hiring — some barriers that I just couldn’t get past, and they held me back from taking the plunge and bringing on a regular team member.

So I just kept putting off hiring… until recently.

Today I’m going to tell you about these mental roadblocks that held me back, and how I got past them. In upcoming articles, I’ll talk about how I wrote a job ad that got more than 200 applicants, as well as the process of hiring and onboarding my new email assistant.

Maybe you’re like me, and you’ve also resisted hiring help in your business, but maybe you can’t put your finger on why you’re hesitant. Or maybe you know exactly why you’re hesitant, but you just can’t get past it. I’ll show you how I overcame these things, and maybe it will help you do so as well.

Mental Barrier #1 — If you want it done right, you’ve got to do it yourself.

Number one is just the philosophy that if you want it done right, you’ve got to do it yourself. I held on to this for a very long time, and I thought it was easier and quicker to just do everything myself. Again, I had streamlined my processes and made things as fast and efficient as possible.

I also have very high standards — I felt like nobody else could edit my videos just the way I like them. Or nobody else could write emails that were not only perfectly grammatically correct, but also in the right tone, being helpful, but also being concise, correcting my students’ errors, but also being encouraging.

I just felt like I had it down, and nobody else could match my level of quality. How did I get past this?

Well, first of all, I hit the point where it started getting painful. The volume of email had increased to the point where it was taking up a lot of my limited time, and it was holding me back from working on other things in the business. I had to hit the point where it was getting painful in order to push me past my comfort zone and say, “Okay, I really need to take on help in responding to these emails.”

While I was handling it all myself and it wasn’t an issue, there was no motivation to hire. But once it started getting painful, then I started really considering bringing on help.

The second thing that helped me was just to get over myself.

I’m not the only person with great skills and an excellent work ethic. There are lots of other people out there who also have those qualities. I know that as entrepreneurs and as creators of the business and the ones who have been doing everything ourselves since the beginning, it’s easy to fall into the trap of thinking, “Only I can do this perfectly. Only I can do this right. Nobody else can live up to my standards” — but that’s not true.

There are a lot of other excellent workers and excellent potential employees out there, and you just have to get it into your head that if you get one of those people on your team and you train them well, then they’re going to take a huge amount of work off of your plate and you will be able to mentally relax knowing that the work is in very skilled and diligent hands.

I know this because in my previous job, I was that person for someone else. I was hired to take on email, communications and website maintenance. And the person who had previously been doing that work, the Director of Communications, often told me, “Shayna, I am SO glad I can just hand you a task and you can get it done well, the same way I would do it, and then I don’t have to worry about it. I don’t have to be double checking your work, it is such a relief for me.”

You can find that person for your team as well, as long as you get over and let go of that attitude of “if I want it done right, I have to do it myself.” That is absolutely not the case.

The third thing that helped me get over the “must do it myself” attitude was documenting guidelines and processes around these tasks.

The reason that it’s really easy for me to do them is because I’ve got seven years of experience, and so the process is all in my head, it’s natural, I just go through it — bam, bam, bam, I can respond emails really quickly.

Documenting what’s natural to me, what’s in my head, and putting it on paper — first of all, this made it clear how much I was holding on to in my head. I ended up with 10 pages of email guidelines, and then I tried to edit them down to make it a little less overwhelming.

When you put your processes on paper, the great thing about this is that yes, you can use them to train your employees and your employees can also refer back to them so that they don’t have to keep asking you questions.

Also, these documents will outlive your employees. So if you take on one person and you train them, and then sooner or later they leave to go on to a different opportunity , and you bring on someone new, you already have the training material there so you don’t have to start from scratch in training that person.

So make sure to get your guidelines and processes down on paper. Even if you’re only working by yourself right now, it’s still helpful to see it all laid out in a clear manner, it can help clarify even your own processes as you run through them.

Document your standard operating procedures in writing — that’s good for a quick reference — and there are some things that also might be best documented with screen casts, if they are cumbersome in writing or just that are easier to see in a visual manner. Run through the process yourself and record your screen. I use a program called Loom that makes it super easy to record a screen cast with yourself just speaking over it.

So I’ve outsourced publishing my blog posts to my website, to Facebook, Twitter, and YouTube, as well as my podcast from my main business, and the way I trained the people who are doing that is I ran through it myself while talking through it and using Loom to record my screen.

The fourth thing that helped me get past the idea of having to do everything myself was just to relax my perfectionism a bit and to be okay with small mistakes or small differences in the way an employee might handle something versus the way I handled something.

Obviously, you want to try to train the person to avoid large screw ups. But if there’s something small, learn to loosen your grip on the perfectionism and to be okay with some of those small differences.

Notice how strongly entrenched my belief of “I have to do it all myself” was, that I had to have four different things just to get me past this one belief!

— Hitting the point where it started getting painful to do it all myself.

— Getting over my ego, the thought that only I could do it perfectly and realizing that other people could do it just as well.

— Documenting my guidelines and processes.

— Learning to be okay with small mistakes or slight differences.

It took all of that to get me out of this mindset of needing to do the task myself. That’s only the first mental barrier, I think it might have been the strongest one, but here are a couple of the others.

Mental Barrier #2 — I want to pay an employee well, but that money comes off my bottom line, so I’ll just wait until my business is bigger.

I figured, “I don’t really need someone right now. I’ll just wait until I grow a little bit more so that I can comfortably pay the person.”

The truth is, if you’re in a stage at business when you don’t yet have enough to support your own lifestyle, it’s really hard to think about taking on another person because that’s a major expense. Also revenue can fluctuate — so what if you have a really down month and then you can’t pay your person and pay your bills? The financial aspect can be nerve wracking.

So how did I get past this roadblock?

Well, I did wait until my business met my desired lifestyle comfortably.

But the other thing you can do, if the expense of taking on someone is intimidating, is you can start small. I’m taking on an email assistant for just 12 hours a week. And then over time, if needed, the person can grow into more hours and or bigger roles.

So when you bring someone on to your team, it doesn’t have to be immediately full time, 40 hours a week, with a competitive salary and benefits package. Know you can take on someone regularly part time and see how that works out, how much work they can handle, and how much work there even is for them to handle. That expense will not be as large, and then you can up their hours over time — or not.

A lot of entrepreneurs build their teams with a whole bunch of part-timers who each have a specific role — that keeps expenses low. The other thing that I’m doing to avoid taking a huge financial hit right away is that I’m hiring only one person at a time.

So right now I’m taking on an email assistant. Last month, I took on assistants to help me with the publishing process. And then maybe later I’ll take on an audio/video editor — but spacing them out like that instead of trying to onboard three or four people at the same time also helps me kind of ease into it. See how the budget looks from month to month, and hopefully the business will grow and it will be easier and more comfortable for me to take on future team members.

So if it’s the finances that are holding you back from hiring, first, take a good look at your own financial situation, see if your business is comfortably supporting you… or if it’s kind of on the edge where taking on someone would put you would make you a little bit uncomfortable. That’s maybe not a great situation.

But once you have hit a point where you really could take someone on, start someone small, start with partial hours and then one hire at a time and work up from there.

Mental Barrier #3 — How can I trust someone with vital access to my system?

In order to take on an employee to help you with something, you need to give them access to your website or to your email system. But I kept thinking, “What if I get someone incompetent who accidentally deletes my whole Facebook page? Or what if a disgruntled employee sabotages my business or steals my mailing list?”

That might be unlikely, but the fact is that our businesses are our livelihoods and part of our legacy that we’re building in the world and so we care about them deeply. Plus, we do want to protect ourselves against what I like to call single points of failure or worst case scenarios.

So I was nervous about letting someone into my business ecosystem and giving them passwords. What if they did something wrong that damaged my business?

How did I get over this barrier? First of all, there are a lot of tools that have different access levels that are kind of set up for taking on team members and giving them access but without giving them full access.

So if you use a password manager like last pass or one password, those often have a feature where you can share a password with someone and give them access without them actually seeing the password.

In WordPress, you can enable someone to be an editor — they can add posts and/or publish posts, but not an administrator, so that means they don’t have the full access to all of your plugins and all of your themes and all of your design. They can only publish and edit posts.

When it comes to social media, I use Hootsuite, a tool that enables the person to post to my Facebook and post to Twitter and YouTube, but they don’t have full access to the account so they can’t delete the entire page. They can’t change the password and lock me out of my own Facebook account or YouTube channel.

It’s just an extra little layer of protection so that the team members have only what they need to get their task done, but not enough to do real damage, whether intentionally or unintentionally.

When it comes to email, a good way to do that is to run it through a help desk system like HelpScout or Groove, I’m using one called Missive which overlays a Gmail account. Again, it can help give people access to your email without them being able to do stuff like change your main account password.

Maybe it’s paranoid to think about someone sabotaging your business. But it’s good to take preventative measures and use tools that can help limit and mitigate that risk a little bit.

Of course, another way to mitigate this risk is to screen your candidates for competency and integrity. You want someone who is honest and reasonably tech savvy, so they won’t accidentally delete your entire YouTube channel.

And you want to give them clear training. So if there’s something that’s a little bit involved or a little bit technical, have them run through the steps while you watch them on the screen share, so you can see if they’re doing it right. If they’re not clicking on anything they’re not supposed to be clicking on, or making any errors in the process.

Finally, of course, we want to avoid having disgruntled employees. So maybe it goes without saying, but maintain a good working relationship and treat your people well. The Golden Rule, right? Treat others how you would want to be treated.

So would you want to work for yourself? If you’re being a horrible, micromanaging, criticizing boss, is your employee going to enjoy that experience? And is your employee going to stay? Probably not.

See if you can make a job that would be awesome for anyone to have — be an awesome boss and have periodic check-ins about how your employee is feeling in the role. Are they having trouble? Is there anything they could suggest to make things better? Do they have enough access to you? Or are you being either too hands on or too hands off?

Make sure to check in with your team members — that will also help preserve a good working relationship.

Mental Barrier #4 — I don’t want to have to manage people.

I like doing the work myself. I don’t really like having to supervise others doing the work, or having to check up on people’s work.

How did I get over this mental barrier?

Realizing that if I hire well, and I train well, that person will be able to work independently with little need for hands on management.

Now, obviously, I’ll still need to do some supervision, especially in the early days as that person is getting acclimated — learning my systems, learning my business — and they might need a little bit more help or oversight.

But over time, if I hire someone with a strong work ethic, then I won’t have to keep checking up on their hours or monitoring their screen to make sure they’re working the hours they say they’re going to work. Someone with a strong work ethic will work properly, and they’ll have a desire to do the work well.

So I might spot check their work, but I don’t have to be continually supervising or double checking everything. That defeats the purpose of hiring someone if you can’t trust them to do the work mostly independently.

Another thing that helped me get past this hesitance to have to be managing people was a suggestion from my friend Gabby, who suggested: When you hire someone, bring them on for a paid trial period — that could be one month, could be three months, depending on the role, could be a couple of weeks — bring them on, see how you two work together.

If it doesn’t work out, whatever the reason, if the person is just not doing the work to your expectation, or if you’re just butting heads and having lots of miscommunications, then at the end of the trial, say, “Thank you for your help, but it’s just not a good fit” — and you part ways.

So that helped me feel like I could take someone on and work with them for a month — and if it’s not working out, we can separate and I can let them go. But hopefully at the end of the month, they’ll be fully trained so that they can work independently without me having to be looking over their shoulder, because that’s not really pleasant for either me or the employee.

So those were my four major mental blocks: getting past the philosophy of “if you want to do it right, do it yourself,” getting past the financial discomfort of taking someone on and having a consistent obligation to pay their payroll, learning to trust someone with access to my business systems, and finally getting past the unpleasant idea of having to micromanage or double-check the person’s work.

I was able to get past all four of those blocks — so I pulled the trigger and posted my job ad a couple of days before the New Year.

And to my surprise, I got several hundred applicants, which was amazing. I had to actually take the job ad offline after about a week, because otherwise it would have gotten too overwhelming.

So next time, I’m going to tell you how I wrote a job ad that got that many applicants as well as how on earth I narrowed it down to the top few. And then what I asked in the interview, as well as how I trained and onboarded the person who I eventually selected to be my email assistant.

Have you had any mental barriers to hiring?

It can be a really big step going from solopreneur to team leader. That’s a major change in your business, as you shift from wearing all the hats and doing most of it yourself, to a more strategic or selective role as other people take care of some of the basic tasks.

I’d love to hear your thoughts about that — leave a comment!