5 Experts Discuss Their Biggest Hiring Challenges Ever

Welcome to Recruiter QA, where we pose employment-related questions to the experts and share their answers! Have a question you'd like to ask? Leave it in the comments, and you might just see it in the next installment of Recruiter QA!

Today's Question: If only every hiring process went smoothly! Unfortunately, recruiters and hiring managers know that challenges are bound to arise from time to time.

What's the biggest challenge you ever faced while trying to make a new hire? How did you overcome the challenge, and what lessons did it teach you about recruiting and hiring?

1. Super Specific Roles Can Be a Pain to Fill

One of the biggest hiring challenges we've ever faced was when we were hiring a technical adviser for our webinar platform, since neither myself nor my cofounder had any kind of technical background. We were faced with trying to find someone with a background in streaming, a lot of experience with our tech stack, and flexible hours. It wasn't an easy task.

We went through dozens of interviews by ourselves, but we were never able to find the perfect person we would be able to rely on for many of our future technical decisions.

As time went on, we were able to find great candidates, but none of them fit the exact position that we were trying to fill. After a few months of searching, we started working with a few recruiters to help us fill the position. One of the recruiters connected us with a dream candidate almost immediately. A couple weeks later, we made the hire, and he is still with us today as a technical adviser.

One of the big lessons that we learned from this is that the more specific requirements you have for a role, the harder it is to fill the position. Sometimes, it can be better to start more generally, knowing that a candidate can evolve and over time become the perfect candidate. On top of that, we learned the importance of tapping every possible resource when it comes to filling the hiring funnel. When we hire now, we try to get as many candidates as possible, and then we quickly filter them to set up the best interviews.

— Wyatt Jozwowski, Demio.com

2. Your Reputation Rides on Your Choice

I find interviewing to be the most challenging part of the process because not only do you need to talk about qualifications and all the technical aspects of the role, but you also most importantly need to find out if this person has actual passion for the job. Do they talk about past jobs fondly? Do they love their work? Are they a good fit for your team? Will they represent the company's image in the way you want it projected?

You have to ask the right questions and come up with the conclusion yourself. It is you, after all, who has to introduce this new member to your team. It's your reputation that is riding on this choice.

— Nick Sawinyh, Seomator

3. Hiring Remote Employees: Daunting, but Doable

One of our digital marketers works remotely, which we thought was going to be quite a challenge. Before he was hired, it was requested that he visit the office for an in-person interview. After he was hired, it was also required that he be in the office for a two-day onboarding period so that he could get acquainted with the brand, the team, the procedures, and the policies. This served as a great introduction for both himself and our team, which allowed for a smoother transition for remote work. We hold weekly video meetings on Slack where we review all tasks assigned for the week and get updates on progress. Between Slack, chat, email, and Basecamp, we are able to work well together to achieve our goals. This has taught me that hiring remote employees can be done, and it can turn out great!

— Brandon Chopp, iHeartRaves

4. Sometimes, It Makes Sense to Wait

The biggest challenge that I ever faced when hiring was finding someone with experience with the right mix of software. I wanted to bring on someone who had experience with email marketing software, SEO software, and online advertising management software. I didn't want to hire someone with a specific skill set and then train on the rest. At the time, it didn't make financial sense to hire three separate people, either.

I could afford to wait, and I held out on this hire. It was difficult, but I did it. Eventually, I found someone who had the right mix of experience I was looking for. It was like prospecting for gold; I had to remove all the dirt first. I wouldn't recommend this waiting/promoting game if you have to have someone quickly, but finding that perfect candidate was definitely a struggle.

— James Pollard, TheAdvisorCoach.com

5. You'd Be Surprised How Far Your Network Reaches

One of my biggest challenges was hiring a country manager (Malaysia) for a global client. The hiring manager was based in Singapore, I was based in Sydney, and the position was in Malaysia. The problem? I'd never been to or worked on a role in Malaysia.

The experience provided a steep learning curve from a professional, cultural, and economic perspective. Having never worked in that market before, I didn't know the lay of the land, so I had very little prior knowledge as a framework for the recruitment process. I'd previously done some work in Singapore, but Malaysia was a whole new playing field, complete with new traditions and customs I had to learn. Economically, with no experience of how Malaysia's currency worked, I struggled benchmarking salaries for the role.

I ended up coming out with several lessons I've drawn on many times since. Set yourself and the search up for success by doing your research before kicking off the process. Always be open to utilizing your network; you'd be surprised just how far it reaches. You only learn by doing, so don't be afraid to make mistakes. Every mistake is an opportunity to learn something new.

— Jamie Finnegan, Finder.com