What Should Small Business Owners Consider When Making their First Major Hire?

    Authored By

    Small Biz Digest

    What Should Small Business Owners Consider When Making their First Major Hire?

    Navigating the crucial first major hire can be a defining moment for small business owners. We've gathered insights from founders and CEOs, sharing their experiences and lessons from hiring to leverage time to clearly communicating culture and expectations. Explore these fourteen diverse perspectives to inform your own hiring strategies.

    • Hire to Leverage Your Time
    • Find the Right Company Fit
    • Prepare for Candidate Inquiries
    • Strategize for Cultural and Skill Fit
    • Prioritize Cultural Fit and Shared Vision
    • Seek Versatile Candidates with Shared Values
    • Emphasize Values and Vision Alignment
    • Promote the Interns
    • Combine Networking with Clear Job Descriptions
    • Align Hire with Core Mission and Skills
    • Assess Team Needs and Streamline Hiring
    • Apply Data-Informed Candidate Evaluation
    • Diversify Recruitment Channels for Better Fits
    • Communicate Culture and Expectations Clearly

    Hire to Leverage Your Time

    I approached my first major hire with the idea that I wanted to bring someone on who was going to be the most leveraging to what I was already doing. I documented and analyzed what was taking up the majority of my time—non-revenue-producing activities—and made sure that my first hire was someone who would not only take the tasks off my plate but also could be left with the responsibility of seeing it through from A to Z. This first major hire was key, as it allowed me to free up my time and refocus back on revenue-generating activities.

    Matthew Sanjari
    Matthew SanjariFounder and Business Coach, PRIME Consulting

    Find the Right Company Fit

    During my first experience with hiring a major position, I learned the importance of finding the right fit for my company. Before beginning the search process, I took time to thoroughly understand the key skills and qualities that were essential for the role. This helped me create a clear job description and identify specific criteria for evaluating candidates.

    I also learned the value of utilizing a multi-faceted hiring strategy. Instead of relying solely on one method, such as job postings or referrals, I used a combination of approaches including online job boards, networking events, and recruitment agencies. This allowed me to reach a wider pool of candidates and find the best fit for my company.

    One of the biggest lessons I learned from my first major hire was the importance of cultural fit. While skills and experience are important, it is equally crucial to find someone who aligns with the values and culture of your company. This ensures a harmonious working environment and helps to maintain a positive company culture.

    Ryan Nelson
    Ryan NelsonFounder, RentalRealEstate

    Prepare for Candidate Inquiries

    My first hire wasn't one I made for my own company, but for the staffing firm I started my career with back in the day. I remember my first assignment as a junior recruiter was hiring an IT analyst for a well-known organization. I had paid attention to my company's training, so I was fairly certain I would soon find a suitable candidate for the role.

    Once I had posted the job ad using the little information provided by the hiring manager, I moved on to reviewing resumes and interviewing candidates. That's when I realized I didn't have much of an idea about the role. I didn't have the right answers when candidates inquired about the team structure and their typical workday, which led to talented professionals ghosting me after the initial interview.

    Ultimately, I made a list of common questions candidates had and contacted the hiring manager for more details about the job. I found the right candidate in twice the amount of time it should have taken normally, but this experience taught me a valuable lesson. It's crucial for interviewers to prepare for job interviews as much as candidates, a lesson that has since guided my approach to hiring.

    Since then, I have prioritized learning about every job role I'm assigned to fill and urge my team to do the same. It reflects poorly when, as a major decision-maker in the hiring process, you're unaware of what the position you're hiring for entails.

    Joe Coletta
    Joe ColettaFounder & CEO, 180 Engineering

    Strategize for Cultural and Skill Fit

    Approaching my first major hire was a pivotal moment in my business journey, and I approached it with careful consideration and strategic planning. First, I identified the specific skills and expertise needed for the role by evaluating the current needs of the business and projecting future growth trajectories. Next, I crafted a detailed job description outlining the responsibilities, qualifications, and expectations for the position, ensuring clarity and alignment with the company's objectives. Utilizing various recruitment channels such as job boards, networking events, and referrals, I sought out candidates who demonstrated the requisite skills, experience, and cultural fit for the organization. During the interview process, I prioritized candidates who showcased not only technical proficiency but also a passion for the industry, a strong work ethic, and a collaborative mindset.

    Through this experience, I learned the importance of thorough preparation and diligent vetting when making critical hiring decisions. Taking the time to clearly define the role and establish criteria for success enabled me to identify candidates who were well-suited to contribute to the company's growth and success. I also recognized the significance of cultural fit and alignment with the company's values in fostering a positive and cohesive work environment.

    Michael Hurwitz
    Michael HurwitzCEO and Co-Founder, Careers in Government

    Prioritize Cultural Fit and Shared Vision

    In the early days of Toggl, making our first major hire was a milestone that came with its own set of challenges and learning opportunities. Reflecting on that time, I realize how critical it was in shaping our approach to team building and company culture. Below, I delve into how we navigated that pivotal moment and the key takeaways that have influenced our hiring philosophy.

    For our first major hire, we sought not just a skill set that matched our immediate needs but also a personality that fit our budding company culture. We placed a strong emphasis on open communication, adaptability, and a shared vision for what Toggl could become. This approach involved a thorough interview process that went beyond technical capabilities to include discussions about values, work ethics, and long-term goals. It was a learning curve, understanding the importance of alignment beyond the resume.

    One of the primary lessons was the critical role of cultural fit in addition to technical skills. A candidate who shares your company's values and vision can grow with you and contribute to a positive, cohesive team environment. This experience underscored for us the importance of looking beyond the resume to find individuals who are truly aligned with our ethos and aspirations.

    Alari Aho
    Alari AhoCEO and Founder, Toggl Inc

    Seek Versatile Candidates with Shared Values

    Embarking on the journey of making my first major hire at Zibtek was a pivotal moment that not only tested my resolve as a business owner but also set the stage for the company's future growth. Reflecting on this experience, it's clear it was a blend of intuition, strategy, and learning—a process that taught me invaluable lessons about building a team that shares your vision and drives your business forward.

    The process began with a clear understanding of what Zibtek needed most at that juncture. It wasn't just about filling a position but about finding someone who could wear multiple hats, inject fresh energy into our projects, and embody the company's ethos. I looked for a candidate with not just the right skills but also the right mindset—a cultural fit that could inspire and be inspired by our vision.

    We cast a wide net, leveraging both our professional networks and job platforms, ensuring the role was visible to a diverse talent pool. The selection process was rigorous, involving multiple rounds of interviews that focused not only on technical expertise but also on problem-solving abilities, leadership potential, and cultural fit.

    Skills can be taught, but alignment with company values and culture is intrinsic. A candidate who shares your vision and values will be more committed and motivated to contribute to your business's success.

    In the early stages of a startup, roles are often fluid. Hiring someone versatile and adaptable can be a game-changer, as they can navigate through the multifaceted challenges a young company faces.

    Rushing to fill a position can lead to compromises. Patience in finding the right candidate ensures you bring on board someone who truly enhances your team.

    A comprehensive onboarding process is crucial. Investing time in ensuring your new hire understands their role, the company's operations, and its culture lays the groundwork for their success and integration into the team.

    This major hire was more than an addition to our team; it was a stepping stone that helped define our path forward. The experience underscored that hiring is not just about filling a gap—it's about envisioning the future of your company and choosing someone who will journey with you towards that future. It taught me that the right hire can catalyze growth, foster a positive workplace culture, and be a key player in the company's success.

    Cache Merrill
    Cache MerrillFounder, Zibtek

    Emphasize Values and Vision Alignment

    Approaching our first major hire at MyTurn, we prioritized alignment with our core values and the potential for growth within our startup ecosystem. We crafted a detailed job description highlighting not just the skills we were looking for but also the kind of mindset that would thrive in our company culture. Through a meticulous, multi-stage interview process, we evaluated candidates' technical abilities, problem-solving skills, and how they resonated with our mission of transforming the recruitment landscape.

    From this experience, I learned the critical importance of patience and open communication throughout the hiring process. Transparently sharing our vision and challenges helped us find a candidate who was not just capable but excited to join us on our journey, reinforcing my belief that alignment of values and vision is key to building a strong foundation for our team.

    Amit Doshi
    Amit DoshiFounder & CEO, MyTurn

    Promote the Interns

    My first hire was an intern who could help with simple video-editing tasks. I was doing everything myself and needed some sort of help, even if it was for some of the smallest things that were easiest to outsource. That hire wound up turning into my right-hand man, and he now leads 15 other team members and takes almost everything off my plate. By shadowing me daily and taking my feedback well, they were eventually able to give the same feedback I would give and figure out how to scale up the team and get me back more of my time.

    Devlin PeckOwner, Devlin Peck

    Combine Networking with Clear Job Descriptions

    When starting a business, there comes a point where you need to make your first major hire. This could be someone to join your team as a co-founder, or an employee who will help take your business to the next level. Either way, this is a crucial decision that can greatly impact the success of your company. The first major hire for any business is a significant milestone. It marks the transition from being a one-person show to building a team. This hire can also set the tone for company culture and future hires. It is crucial to approach this decision with careful consideration and a clear understanding of your business needs.

    When it came time for me to make my first major hire, I had a mixture of excitement and anxiety. On one hand, I was eager to have someone join our team and help us grow. On the other hand, I was worried about making the wrong decision and the potential consequences it could have on our business. I approached the hiring process by first identifying our company's needs and creating a clear job description. This helped me narrow down the specific skills and qualities I was looking for in a candidate. I also took into consideration our company culture and values, as it was essential to find someone who would fit in with our team.

    Next, I used a combination of networking and job postings to attract potential candidates. This allowed me to reach a larger pool of applicants with diverse backgrounds and experiences. I also made sure to thoroughly review resumes and conduct multiple rounds of interviews to get a better understanding of each candidate's skills, personality, and potential fit for our team.

    Mary Sullivan
    Mary SullivanFounder & CEO, Company That Buys Houses

    Align Hire with Core Mission and Skills

    When I made our first major hire, I focused on aligning with our core mission of promoting an active lifestyle. I sought someone not only skilled in marketing but also passionate about fitness. We chose a candidate who had run marathons and had substantial marketing experience. The process taught me the importance of clarity in job descriptions and interviews.

    Initially, our description was vague, leading to a broad mix of applicants. After refining our criteria to emphasize both industry skills and a commitment to fitness, we attracted the right candidates. This experience underscored the need to continuously refine our hiring process to match our company’s evolving goals.

    Jay Barton
    Jay BartonCEO & Founder, ASRV

    Assess Team Needs and Streamline Hiring

    First of all, I analyzed our team's current strengths and weaknesses. It is to identify specific skills needed to match our capabilities. Then I carefully crafted a detailed job description outlining the new hire's responsibilities, qualifications, and expectations.

    After this, I developed a targeted recruitment strategy leveraging multiple channels like job boards, networking events, and referrals to reach potential candidates. I also collaborated with HR to streamline the hiring process. I conducted thorough screenings and interviews to assess candidates' qualifications, experience, and cultural fit.

    Once the hire was made, I facilitated a comprehensive onboarding process so that the new team member could become familiar with their role. They can understand the team dynamic and company culture smoothly. Throughout the process, I actively sought feedback from both the team and the new hire to identify areas for improvement.

    Saikat Ghosh
    Saikat GhoshAssociate Director of HR & Business, Technource

    Apply Data-Informed Candidate Evaluation

    When I approached my first major hire, I leaned heavily on my background in marketing strategy and my understanding of organizational dynamics from experiences at companies like Thinksia. Recognizing the critical role this position would play in shaping our marketing direction and team culture, I looked beyond the resume to assess how candidates could contribute to our overarching goals and fit within the team.

    From my expertise in creating connected strategies and fostering teamwork, I prioritized candidates who showed not just a strong skill set in marketing but also a collaborative spirit and a capability to inspire others. A memorable breakthrough came from applying insights gained through precision monitoring and real-time analytics, similar to strategies we deployed at Thinksia for client success. By evaluating candidates' past projects and their impact analytically, I was able to gauge their strategic thinking and effectiveness, a process that underscored the importance of data-informed decisions in every aspect of business, including hiring.

    What I learned from this hiring experience was invaluable—it highlighted the significance of aligning a new hire with the company's vision and the existing team's culture. The process reaffirmed my belief in the power of a well-rounded candidate, not just in terms of technical ability but also their potential to drive innovation and collaborative success. This approach not only resulted in a stellar addition to the team but also in enhanced team dynamics and a stronger, more cohesive marketing strategy. It was a testament to the importance of embracing comprehensive evaluation criteria and informed decision-making in building a team poised for collective achievement.

    Timothy J Williams
    Timothy J WilliamsPrincipal Consultant, Thinksia

    Diversify Recruitment Channels for Better Fits

    When I made our first major hire, I focused on leveraging a variety of recruitment channels to ensure we found the right talent. We advertised the position on both industry-specific job boards and broader platforms to cast a wide net. One memorable candidate came through a niche logistics forum, which was a channel I initially underestimated.

    This experience taught me the value of diversifying recruitment sources; it's crucial not just to rely on the most popular platforms but to explore specialized spaces where unique, skilled candidates might frequent. This strategy has significantly shaped our hiring practices, making them more inclusive and effective.

    Sandra Malouf
    Sandra MaloufPresident, Eurolog Packing Group

    Communicate Culture and Expectations Clearly

    When I first hired someone at Stallion Express as a full-time employee, I wanted them to have the right skills and contribute to our innovation, customer-centricity, and growth culture. I carefully designed the job description to attract top talent by emphasizing the potential for creative problem-solving and growth within our fast-paced team.

    During the interview process, I emphasized cultural fit as well as adaptability. One individual stood out not only because of their impressive CV but also because of their passion and commitment to our values.

    After onboarding them, I realized how important it is to communicate clearly and set expectations. Providing them with a comprehensive onboarding process and scheduled check-ins made them feel valued and part of the bigger company vision.

    In addition, this experience highlighted the importance of working together in an environment where new employees feel they have the freedom to express their different points of view. Their new ideas and energy brought a new dynamic to our team, resulting in creative changes in our marketing approaches.

    My first big hire taught me how important it is to hire not just for skills but for cultural fit and growth. It showed me the importance of clear communication and creating a supportive culture where everyone feels appreciated and driven to do their best.

    After onboarding them, I realized how important it is to communicate clearly and set expectations. Providing them with a comprehensive onboarding process and scheduled check-ins made them feel valued and part of the bigger company vision.

    My first big hire taught me how important hiring is for skills, culture, and growth. It also taught me how vital clear communication is and how to create a supportive work culture where everyone feels appreciated and driven to do their best.

    Diana Zheng
    Diana ZhengHead of Marketing, Stallion Express