Top 3 Mistakes I Made When Hiring Employees


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As a small business owner, hiring employees is one of the most important expenses and decisions you can make to grow your company. You need qualified people who can move things around neatly when needed, take care of your client’s needs, and make sure they work well with the team. Ultimately, you want someone who will continue to make you the best business owner you can be by uplifting you and providing you with the necessary resources. 

Madeliene Costa, Founder and CEO of Succeeding Small, a Digital Marketing Firm in Colorado Springs knows that being a boss during the hiring process is challenging. She expresses that it is one of the hardest things she had ever done in her whole entrepreneurial journey. Madeleine goes on to reflect on her hiring journey and the mistakes she has made along the way. 

Learn the top 3 mistakes Madeleine Costa has done in her hiring process, and ways to prevent these mistakes from happening in your small business by reading below.

Don’t Hire Employees Casually or Conveniently 

Madeleine explains that the biggest mistake she has made in her hiring process is onboarding people out of coincidence. She expresses that during the beginning of her small business, people often fell into her lap that were interested in the industry and wanted to learn more about it. Madeleine calls this “hiring casually” – hiring employees who are convenient at the time when you need someone to be added to your team. 

Dealing With ‘Churn’

Madeleine expresses how, at the moment, it was great for her business. She would be able to teach these individuals, give them client work, and be able to have some of the weight off of her shoulders. However, she says because she did not have the systems in place to delegate tasks to these employees easily, nor did the individuals have a genuine interest in her company, mainly just the industry as a whole, these individuals would never stay for long. Often enough, they would take the knowledge they would learn from Madeleine and move on to other things. Which, of course, is perfectly reasonable, Madeleine says. “If I’m able to give somebody their passion, if I’m able to help somebody get where they want to go, that is satisfying enough for me”, she states.

However, Madeleine really wanted individuals who were proud of their job and excited to be a part of her company. She wanted people who would stay long-term, not leave once they found something better. 

The Shift – Hiring With Intention

Hiring employees casually has caused Madeleine to lose a lot of team members along her entrepreneurial journey. Though, she found once she was hiring with intention, and had put a formal hiring and interviewing process into place, people were much more likely to stay long-term. These individuals were passionate and excited about the position. They wanted to prove themselves and pour all their energy and time into growing the company. “That kind of energy is a game-changer when it comes down to building a long-lasting team for me”, says Madeleine. 

Now, Madeleine does not hire casually. She expresses that she wants to hire employees who are right for the job, who have the necessary experience, skills, and specialties, rather than someone who is convenient at the time that may seem like the quickest solution, but at the end of the day, won’t be a long-term solution. That leads us to Madeleine’s second mistake in the hiring process.

Have a Thorough Interview Process

Madeleine’s second-biggest mistake in the hiring process is not having a thorough enough interview process in place for her small business. “Once I made the decision to hire people more traditionally, it was another stage of the unknown. I had no idea how to properly interview. I had no idea how to accurately judge character because I assumed that I was pretty good at that, and I learned a lot after hiring people that I wasn’t fully confident in, or I just skimmed the process just because I was constantly hiring out of necessity,” Madeleine states about structuring her interview process. 

Madeleine expresses that at this point in her entrepreneurial journey, she was in crisis mode. She needed to fill a position as soon as possible but wanted to make the right decision. This caused her to hire employees more casually than strategically. 

The “Pre-Interview”

Now Madeleine has a process in place, she explains it may be overkill, but it is working so far. “I have a job posting that I distribute on places like Indeed, LinkedIn, or Facebook and people will apply for the job. I will send an email saying, please answer these questions. The three questions I ask after somebody applies for the job position are why are you passionate about this position? And what experience do you have? Number two is why are you interested in working here? And number three is what are you looking for in a workplace?” Madeleine describes.

“So these three questions are just like my pre-interview. It gives me a sense of if somebody is really passionate about something, if they have enough words to describe why they care about what they do, it shows me that they are a good writer, which is really important to me. Somebody who can communicate well and effectively,” Madeleine explains about her current hiring process. 

She explains that the last question she asks in her pre-interview questions, “what are you looking for in a workplace?” tells her if they will get along with the team and company culture as a whole. 

First Interview (Pre-Screening)

Once she asks these questions, Madeleine is able to filter through people very quickly between their answers to these questions and their resume. After she is done filtering through the candidates, she schedules the first interview with them. The interview will either be led by Madeleine or Madison, Succeeding Small’s Operations Manager. Madeleine explains this is a way to pre-screen the candidate if she does not have enough time to do so in her schedule. 

During this first interview, Madeleine recommends asking the candidate open-ended questions, that way the candidate is able to tell her stories, rather than ‘yes’ and ‘no’ answers. “If I’m able to create more of an open conversation, I actually learn a lot more about the person,” Madeleine reflects on her interview process.

Second Interview or Skills Test

After this, Madeleine will schedule a second interview, if she still needs time deciding, or put them through a skills test. There are a couple of different ways to do a skills test. One way is to bring the candidate into your office, and pay them for a day so they can showcase what they are capable of doing. This way, you are able to put them through a trial of some sort to identify the skills they are able to do. 

Another way to do this is to send over a quick skills test just to make sure the individual can accurately and effectively do the tasks. Madeleine does not have the person do client work in this instance. She explains that it would be unethical of her to ask someone to do client work without receiving payment. Instead, she has them do something small such as writing a blog post of their choosing or seeing if they can duplicate this webpage on their own, anything that is able to showcase the individual’s skillset without giving them client work. This way, Madeleine knows that the candidate can perform the work needed to fill the position. 

The Offer

After this thorough interview process, Madeleine officially makes them an offer and signs them on for a 60-day trial period. With this trial period, Madeleine is able to ensure the individual is the right fit for the position and the company. Likewise, the individual is able to make sure the company is the right fit for them. In this way, the 60 trial period allows both parties to have time to decide if the position is the right fit for them. It is during the first few weeks of this trial period, often known as the onboarding process, that Madeleine found her third mistake in the hiring process. 

Have a Structured Onboarding Process 

Madeleine has recently learned her third mistake in the hiring process; not onboarding people properly or effectively. She expresses that the term ‘onboarding’ seemed to be too corporate to her and that is why she did not fully embrace this part of the hiring process. She explains that she did not want to do it in the traditional sense, because to her it did not make sense to pay two people (the trainer and the trainee) for three full days to get doused with information. Madeleine expresses that to her, it just felt like a waste of time. 

Why It Matters

Madeleine explains that she has learned from her mistake with her old onboarding process. “A lot of my hires reflected that they felt like they hadn’t been onboarded properly and they didn’t have enough knowledge either about the services that I offered or about our systems. And that made it more challenging for them to do their job. And people often felt a little bit in the dark or kind of overwhelmed by how much they had to do or working within our systems. They just didn’t feel properly trained to do the job at hand,” Madeleine says. 

The Solution

As a solution, Madeleine now pairs new hires with her creative. So the new hires will be paired with Madison, Succeeding Small’s Operations Manager, or another person on the team, to train with for a whole day. On the first day, the new hires learn about the company’s history as well as our clients and the services we provide. After this, she gives them a full day to learn about their craft. On this day, the new hires will be paired with Madeleine, or a specialist, ideally whoever they will be working under. This way, the new hires can learn what they will be expected to be doing, and how they can perform to the company’s standards. They will also be able to get feedback from the specialist this day on how to better their craft or match the company’s standards. 

Madeleine expresses that this new intensive onboarding process has proven to benefit the new hires, as well as the company culture as a whole. 

Succeeding Small is Here to Help you with the Hiring Process

Now that you have heard about Succeeding Small’s mistakes in the hiring process, we would like to hear some of the mistakes you have made in the hiring process as a small business owner. Here a Succeeding Small, we want to create an open conversation about making mistakes as a business owner. So, email our team to tell us the mistakes you have made in the hiring process and the things you have learned from them. We want to hear how you have grown your small business through your mistakes!

Grow your Small Business With Succeeding Small

Succeeding Small is an expert in growing small businesses through our amazing digital marketing, SEO, branding, web design and social media services.  Learn about our services today!

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