What It Really Takes to Hire Your First Employee

The Mission Driven Business Podcast

Hiring your first employee is one of the most significant leaps a business owner can take, and very few people talk openly about what it actually feels like from both sides of the table. In this episode, Brian Thompson flips the script and invites his operations manager, Jesica Berger, to share her perspective on the journey from longtime colleagues to collaborators. Together they unpack what made the transition work, what has been hard, and what other entrepreneurs can take away when they are ready to make their first hire.

 

A Relationship Built on Shared Values

Jesica comes to this role with a background as a tax lawyer, a career she was drawn to because it combined her love of numbers and data with the deeply human element of advocating for clients. She and Brian worked together for nearly seven years at the same firm before Brian left to build his own practice. When the opportunity to work together again came up, it felt less like a business decision and more like a natural next step, one that had been years in the making.

 

Why Trust Made the Difference

Brian is candid about something he has told people for years: he never planned to hire anyone. Bringing someone into a business means showing them the systems, the gaps, the places where the owner is the bottleneck. That level of exposure requires trust that is hard to build in one or two interviews. For Brian, nearly two decades of friendship gave him the foundation he needed. For Jesica, that same history came with its own pressure. She did not want to let him down. She did not want him to take a risk on her and have it not work out. That fear, she says, was real and it stayed with her through the transition.

 

The Emotional Reality of Transition

Jesica spent almost sixteen years at her previous firm. Leaving that position carried grief alongside excitement. She was stepping away from a role where she had become deeply competent and confident, and stepping into something entirely new. At the same time, Brian was giving her access to a world she had always been curious about, financial planning, bookkeeping, the operational side of a growing practice. She describes the work as challenging and energizing in equal measure. The transition from contractor to full-time employee unfolded over six months, giving both of them time to figure out whether the fit was real before making it permanent.

 

Building the Foundation Together

Brian and Jesica structured their working relationship from the start. They mapped out a vision for the role, set benchmarks, and created two distinct types of meetings: working meetings for getting actual tasks done together, and check-in meetings for talking about how things are going. When Jesica felt she was not getting enough time and guidance, she said so. Brian took it to his business coach and they increased the frequency of their meetings. That cycle of identifying a challenge, communicating it openly, and adjusting became the rhythm of how they operate. Visibility has also been central to Jesica’s integration into the firm. Piece by piece, Brian has opened up access to systems, documents, and processes he had previously kept only in his own head. Seeing the gaps himself, through her fresh perspective, has been humbling and clarifying in equal measure.

 

What to Focus on When Hiring Your First Employee

Most entrepreneurs hiring for the first time will not have a decades-long friendship to draw from. They will be making a significant decision based on a handful of conversations, which still can work out. You make the best decision with the information in front of you, take the leap, and figure it out from there. Brian’s approach, both with Jesica and with his clients, is to focus on two core questions when hiring:

  • Will this person enjoy the work?
  • Will they be good at it?

Beyond that, clear expectations, honest communication, and a willingness to iterate matter more than having everything figured out before you start.

 

Staying Present When the Future Feels Uncertain

When anxiety and uncertainty pops up when trying to project too far ahead into the future, Brain offers questions that help him in coming back to the present.

  • How is it going right now?
  • Is there something that needs to change today?

 

Resources + Links

 

About Brian and the Mission Driven Business Podcast

Brian Thompson, JD/CFP®, is a tax attorney and Certified Financial Planner® who specializes in providing comprehensive financial planning to LGBTQ+ entrepreneurs who run mission-driven businesses. The Mission Driven Business podcast was born out of his passion for helping social entrepreneurs create businesses with purpose and profit.

On the podcast, Brian talks with diverse entrepreneurs and the people who support them. Listeners hear stories of experiences, strength, and hope and get practical advice to help them build businesses that might just change the world, too.