This blog post contains the transcription of a free virtual Lunch & Learn we hosted in April 2025 titled, “Getting Ready for Your First Hire.” You can view all of our upcoming webinars here.
Hiring Tips
Who are the Top Experts to Know?
Myra Quick is the owner of Fast Forward Learning and Development. As a Human Resource professional with 25 years of experience in the industry she possesses a deep understanding of human resource operations, recruitment and retention as well as workforce development. Her small business experience comes from growing up in a small family owned business as well as launching 2 successful businesses of her own. Fast Forward services are centered around educating owners on the intricacies of Human Resources. As an HR Business Partner you can count on Myra expertise to provide the knowledge, support, and guidance to care for your most important resource of all: your people.
Joel Parra is the owner of JP Business & Event Consulting. A problem-solver at heart, passionate about making businesses and events run seamlessly. With an MBA from Southern New Hampshire University and over 10 years of experience, he has worn many hats—each one shaping his understanding of what makes businesses thrive. Throughout his corporate career, he has held roles in human resources and business operations across industries including hospitality, consulting, e-commerce, and tech. Whether streamlining operations or designing an employee journey plan, Joel is driven by the impact of a well-executed strategy—ensuring businesses operate efficiently behind the scenes.
Tara Bodine is the owner of True North People Consulting, where she helps small businesses navigate the world of people and work. With over 20 years of experience working in corporate HR, she takes that knowledge and translates it into ways to help small businesses build killer teams, navigate tricky situations, and strengthen their bottom line. Her team offers on-demand, fractional HR subscriptions, allowing business owners to choose the level of support they need. They specialize in serving small businesses with 30 or fewer employees, providing affordable and flexible solutions.
Getting Started with the Process
Hiring your first employee is a huge milestone—and it’s one that brings up a lot of questions. How do you know when the time is right? What if you don’t have everything perfectly figured out? What if you make the wrong choice?
To help business owners navigate this transition, Massachusetts Business Network hosted a recent webinar focused on preparing for your first hire. From understanding when you’re ready to hire to onboarding your new team member with confidence, here are the key takeaways.
How to Know When It’s Time to Hire
If you’re turning away business, missing deadlines, or constantly juggling tasks outside your zone of genius, that’s a strong signal it’s time to bring in help. Another sign? You’re spending most of your time on administrative tasks instead of doing the work that grows your business.
The best time to start preparing to hire is before you’re drowning. Planning ahead gives you time to clarify what you need, structure the role, and set your new team member up for success.
What to Do Before You Post a Job
Jumping straight into hiring without getting organized can lead to confusion, wasted time, and poor fit. Before you post a single job description, take the time to:
Define the role. What exactly will this person do on a day-to-day basis? What skills are non-negotiable? What’s nice to have?
Evaluate the ROI. Can your business sustain this hire financially? What kind of return do you expect in terms of revenue, time saved, or capacity gained?
Identify gaps. Are there specific skills you don’t have that this hire should bring? This is your chance to add complementary strengths to your business.
If you’re still unsure about the exact role, you can create a flexible position—as long as you clearly communicate that responsibilities may shift over time. Research how similar businesses are structuring their teams and use job description templates to get started.
Writing a Job Post That Attracts the Right People
Your job post is more than a list of duties—it’s an invitation to be part of something meaningful. Skip the generic, robotic language and speak directly to the kind of person you want to attract. Highlight what makes your business unique, your mission, and why someone would want to be a part of your team.
Also, be intentional about where you’re posting. For example:
- LinkedIn tends to attract more corporate or professional candidates.
- Facebook or Instagram may be more effective for customer-facing or creative roles.
- Industry-specific groups or community organizations can be great for targeted outreach.
And don’t forget about your own network. Personal referrals, former colleagues, or even a quick post on social media might lead to the perfect hire.
What to Look for in a Candidate (Beyond Skills)
Experience and qualifications matter, but they’re not the full picture—especially in a small business setting where every role has an outsized impact.
When interviewing candidates, consider:
Adaptability. Can they pivot quickly and take on different responsibilities as needed?
Enthusiasm for your mission. Are they excited to be part of what you’re building?
Soft skills. Communication, ownership, and problem-solving go a long way in a dynamic environment.
Working style. Do they thrive with autonomy or prefer collaboration? Will they complement your leadership style?
Understanding what environment helps someone thrive can be just as important as reviewing their resume.
Common First-Hire Mistakes to Avoid
When you’re bringing on your first employee, it’s easy to get caught up in excitement—or pressure—and skip important steps. Here are a few mistakes to avoid:
Hiring friends or family. It may feel convenient, but it often leads to difficult conversations and blurred lines.
Underestimating the true cost. Factor in payroll taxes, benefits, equipment, and your time.
Skipping onboarding. A rushed or nonexistent onboarding process can leave new hires feeling lost or disengaged.
Neglecting performance feedback. Set expectations early and check in regularly to keep things on track.
How to Onboard Successfully
Hiring someone is just the beginning. A smooth, welcoming onboarding experience increases engagement, builds trust, and lays the groundwork for long-term success.
Some best practices include:
Start before Day 1. Send a welcome email, share what to expect, and make sure they have what they need to hit the ground running.
Clear your calendar. Be available during their first week to guide them, answer questions, and build a personal connection.
Document as you go. Ask your new hire to jot down processes and procedures during training. This not only reinforces their learning, but also helps you build your internal systems.
Stay connected. Schedule regular check-ins (weekly at first) to provide feedback, answer questions, and adjust expectations as needed.
Plan for the long term. Consider adding quarterly performance reviews or goal-setting sessions to maintain momentum and support growth.
Even simple things like grabbing coffee together or meeting in person (if possible) can go a long way in building trust and comfort.
Bringing on your first employee is exciting—and a little intimidating. But with thoughtful preparation, a clear sense of what you need, and a commitment to ongoing communication, you can turn that first hire into a game-changing addition to your business.
Resources for Massachusetts Businesses
Amplifying Your Presence with Massachusetts Business Network
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