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Nine Entrepreneurs Share The Biggest Hiring Challenges They’ve Ever Faced

By News Creatives Authors , in Leadership , at August 17, 2021

The process of hiring new employees can be both rewarding and difficult. Hiring managers or HR representatives need to make sure each candidate not only fits into the company culture and values, but also can do the job successfully.

Some hiring decisions can be particularly hard to navigate, especially as a small business owner. Below, nine Young Entrepreneur Council members shared the biggest hiring challenges they’ve ever faced and the steps they took to overcome them. Read their advice to help you if you’re struggling to recruit, hire or onboard new talent for your company.

1. Hiring A Full-Time Operations Manager

The largest and most expensive hire I’ve ever made was my full-time operations manager. Hiring for this role was really scary for me and felt like taking my hands off the steering wheel a bit. I knew that I needed to bring on someone who I could trust deeply with my company, who’d be a true partner to me and who would be responsible for bringing our goals to fruition. To help me better prepare for bringing on this role, I worked with a business consultant who coached me on the CEO/COO relationship and I read a few books on leadership. I had to step out of my comfort zone and into a servant leader role to make it work—and I’m so glad that I did! – Rachel Beider, PRESS Modern Massage

2. Seeing (And Accepting) Each Applicant’s Path

Our purpose is to educate and provide opportunity. When I review a resume or have an interview, I see what this person could potentially do in our company. I go five years ahead of the current moment to where they are getting promoted or taking ownership of a new department. It was hard to realize that sometimes people don’t have that drive. We have adopted a phrase internally: “You can’t fight for them harder than they are fighting for themselves.” Accepting that each applicant has their own path and timeline took some growing in order for me to understand. – Marjorie Adams, Fourlane

3. Distinguishing Between Core And Trainable Qualifications

One of the biggest challenges is finding qualified candidates. Often, roles are so niche that finding someone with all the necessary skills you want is almost impossible. For this reason, it is really important to make a distinction between core qualifications and trainable qualifications. In other words, what are the fundamental skills you need someone to have in order to hit the ground running and what are the skills you can train the person in once they arrive? This really helps widen your pool of candidates by not disqualifying those who are not familiar with the details of your specific business, but potentially have all the right qualifications for success once trained up. – Maria Thimothy, OneIMS

4. Building A Competitive Hiring Package

One of the hardest hiring challenges I’ve experienced has been as a direct result of the pandemic. Many companies (and the VCs funding them) are flush with unspent capital from the past year. With a surplus of funding now available, these companies have begun hiring again. The result is an incredibly competitive hiring market in terms of salary—something we can’t always compete in. One tip we’ve used to make our hiring package more competitive is to elicit more buy-in and excitement before hiring. We’ve added an extra “product demo and brainstorm” call to get potential candidates jazzed about the company. We’ve also gone hard on equity, which gets candidates excited about ownership in the company and makes sure you’re hiring people who genuinely like the business. – Cooper Harris, Klickly

5. Envisioning The Relationship With A New Hire

One of my biggest hiring challenges was finding a COO who would complement my skills and collaborate on a shared vision. I fully recognized how important this role was—and how essential the fit would be—but it can be difficult to envision what the relationship will look like without first having the opportunity to work together. For that reason, before hiring our COO, we engaged on a short-term consulting basis. This allowed both of us to create the relationship we wanted and learn how to work together before making a full commitment to one another. – Lindsay Tanne, LogicPrep

6. Finding The Real Person Behind The Application

I learned that most of the applicants answer questions based on what YouTube or books taught them to do. Only a few are sincere, and only a few will tell you the real deal. Everyone may be perfect and skillful, but not everyone is perfect for the company. We choose someone who is aligned with our company’s vision and mission. We ask random questions and talk heart-to-heart to see the motivation of the applicant. We also spend time checking the background and character references of the applicant. We compare their answers to social media pages and with the people they’ve worked with. – Daisy Jing, Banish

7. Leveraging Personal Recommendations

I absolutely love hiring new team members. I’m very particular about my hiring methods; I never post to job boards, preferring personal recommendations only. As such, it is imperative that I keep healthy connections with many different organizations in the community to be able to find the right candidates through my networks. As a small company, I’m particularly aware of the dynamics of bringing on a new employee, so I strive to find candidates who share our values and who want to serve the mission, not just themselves. By utilizing word-of-mouth to find potential employees, I’m able to learn about them from friends and co-workers on a much deeper level. My last six hires have all come from recommendations in my networks, and they have all been with the company over two years each. – Ashley Sharp, Dwell with Dignity

8. Pinpointing Necessary Job Specifications

The biggest hiring challenge I learned to overcome was pinpointing job specifications. When making our first hire, I thought I could find someone who encompassed everything we needed at that time. I soon learned that wasn’t the case and I needed people who specialized in one skill rather than a jack-of-all-trades who probably doesn’t exist. Optimizing job descriptions helps you find only qualified candidates who are passionate and skilled in one area rather than “okay” at many. It also cuts down irrelevant applicants. I also learned to target relevant job ad platforms rather than posting ads on a general advertising site. You’re more likely to find a brilliant marketer on a platform just for marketers than if you waited for the perfect person to find your ad among thousands on a general page. – Emily Stallings, Casely, Inc.

9. Attracting The Right Candidates

A big hiring challenge I’ve come across is not attracting the right candidates for a certain position. If you aren’t careful, you could end up receiving applications from those who know little to nothing about the industry or the role they’re applying for. That’s why I like to optimize my job postings as much as possible before posting them online. This means adding a clear description of the role, duties, salary range and expectations so there’s little room for doubt. If candidates don’t match those specific qualifications, they won’t get a call for an interview, which brings us closer to the right candidate. – Stephanie Wells, Formidable Forms


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