Guidance for making your first hire from a former Director of Talent

For about ten years before becoming an entrepreneur, I was in Recruitment and Talent Acquisition, leading teams responsible for hiring at companies like SoulCycle, Alfred, and other tech and hospitality brands. In these roles, I was a trusted partner leading new managers and executives alike through the hiring process, many for the first time. This exciting yet daunting process laid the groundwork for my coaching career and my passion for demystifying and democratizing this information for you all, dear readers. 

Once you know it's time to hire your first employee, there are many paths you can follow. It can feel like a lot of pressure. But keep in mind that you can always take small steps, rather than a big leap. If you want to go in the direction of an incredibly low-stakes and low-cost hire, an internship or apprenticeship is a great start. 

As a first-time entrepreneur, I loved using Acadium to find a Marketing Apprentice. Through them, I found Grace, who is still a full-time contractor on my team, going on three and a half years. After the three-month Apprenticeship, I knew she was more than just a marketing intern; she became a “Swiss army knife,” ready and willing to handle whatever administrative project arose. 

Related article: How to Follow your Intuition to Start Your Business

Seek Out Your Executive Operator

Let’s say you’re flush with cash flow and want to bring someone on full-time. In that case, I’d consider hiring someone to be an "Executive Operator". This person will be a project manager, flexing to whatever your needs are in the business. Said another way, they are a “right hand” who will have access to your inbox, calendar, website operations, and social media, and can start to handle administrative tasks while building out the operational needs to sustain them long term. A good example of this type of project would be running customer service, and then suggesting a system like Zendesk to handle tickets when the volume becomes too overwhelming for their bandwidth. 

Now, I know what you’re thinking. “How can I trust someone new to take over such essential pieces of my business?” Building trust with this new hire will likely happen slowly, starting in the interview process. Thinking about the tangible skill sets you need (the role itself) while accounting for the intangible (the business's core values, trustworthiness, honesty, etc.) will help you build out the interview process. And don’t forget to ask for references! 

Identify Your Zones of Genius

Another helpful tip: If you create a Venn diagram of your Zones of Genius alongside those of your potential first hire, there shouldn’t be a lot of overlap. You ideally want to bring someone on board who is an expert in an area you’re inept in. 

For example, I quickly realized that Gen Z Grace could help me with the technical operations of the business, something I fall painfully short on. With a natural affinity and talent for technology, she quickly picked up Squarespace and built out and implemented newer efficiencies on the backend of my website. Grace continues to take on more and more as we grow — she even edits my podcast! 

Kimo Kepano, founder and CEO of The Light Seer Platform, reflects on his first hire in a similar way. “I sought to have someone fill in the blanks of the organization that my brain did not have the time or space to do, meeting the needs of my customer base.” Ironically, by outsourcing customer service to his first hire, he could serve his customers better as an educational guide. 

Prioritize Culture Fit

Which brings me to my last point. Grace isn’t just a great first hire because she’s helping the business run in a well-oiled way; her “can-do” attitude solidifies her place on the team. I firmly believe that hiring someone who embodies your core values is paramount to your success, whether it's your first or 100th hire. If they are interested in what you do and how you do it, they will work as if your business is theirs. That is priceless.

As he hires more individuals, Kimo considers cultural match over skillset. “Now, I prioritize hiring individuals aligned with my brand's long-term goals and vision. A good cultural fit and compatible perspective have become crucial factors in my hiring process.” 

Hopefully, you feel well-resourced to search for and hire your first employee, an important step on your entrepreneurial journey. 

Want more content like this? Explore other posts from Alex on our blog, and check out her podcast Capricorn Rising Inc., a guide to help leaders strengthen their intuitive skill sets and follow their calling.