How To Hire With Confidence: A Step-By-Step Guide For Creative Business Owners
Whether you’re a team of one feeling stretched thin or a growing creative business owner looking to expand sustainably, hiring support can be a game-changer. But without a solid plan, it can also feel risky and confusing.
In our recent webinar with Certified Dubsado Specialist, Jennifer Skinner, operations consultant and founder of Day to Day Assist, she walked through an actionable framework that helps small business owners hire the right support the right way—so they can reclaim their time and grow with confidence.
Here are the top highlights:
Define the role before you post the job
One of the most common hiring mistakes? Skipping the prep work. Jennifer emphasized that clarity is key before you ever share a job post. Start by listing your daily, weekly, and monthly tasks, and then ask:
What drains my energy?
What could be done by someone else?
What keeps me from focusing on growth?
This helps you pinpoint which tasks to delegate—and ensures you’re hiring for real support, not just adding more management to your plate.
Craft a job description like a marketer
Don’t just post a role that says “amazing opportunity” or “join a dynamic team.” You’re not just hiring a body—you’re attracting someone with the values, skills, and mindset to contribute meaningfully to your business.
Jennifer suggests treating your job description like an ad: speak directly to your ideal hire, include details about your business mission and values, and be transparent about compensation, perks, and expectations.
Create a smooth interview and screening process
Once applications start rolling in, a clear screening system is crucial. Use a platform like Airtable or Notion to track candidates against pre-defined criteria—including minimum experience, location requirements, or technical skills.
Bonus tip: Paid test projects are an amazing way to see how someone actually works. Just make sure they’re relevant, fairly compensated, and only assigned to strong candidates.
Nail your onboarding process
Hiring doesn’t end at the offer letter. Set your new team member up for success with a 30/60/90 day plan, documented SOPs, and tools like LastPass, Gusto, or (of course) Dubsado for contract signing and onboarding automation.
Jennifer also shared that even if you’re only hiring someone for 5-10 hours a week, you should treat the process with the same care. It builds trust and ensures that the support you bring on actually moves your business forward. In fact, she encouraged starting small while you’re building your leadership skills and defining what a successful team looks like for your business.
Download Jennifer’s free “Hiring Priorities Matrix” and see below to watch the full replay for more actionable tips.
About Jennifer
Jennifer is a Certified Dubsado Specialist, operations consultant, and the founder of Day to Day Assist. She helps service-based business owners streamline their backend operations, implement the right tools, and build efficient teams. With a strong background in systems development and hiring, she’s helped 45+ entrepreneurs eliminate chaos and scale with confidence.
Jennifer believes that sustainable growth starts with strong systems. Her mission is to equip business owners with the structure and support they need to save time, increase revenue, and scale—without burnout.
