Jessi Burg Of Outgrow Your Garage On How To Hire The Right Person

An Interview With Ken Babcock

Ken Babcock, CEO of Tango
Authority Magazine
11 min readMay 12, 2022


Always include the direct supervisor in the interview processes. You want to make sure that the job that you’re hiring for and the person who is managing that position work well together. You don’t want any surprises when it comes to the expectations here.

When a company is looking to grow, the choice of who to hire can sometimes be an almost existential question. The right hire can dramatically grow a company, while the wrong hire can be very harmful to morale and growth. How can you know you are hiring the right person? What are the red flags that should warn you away from hiring someone? In this interview series, we are talking to business leaders who can share insights and stories from their experience about “How To Hire The Right Person”. As a part of this series I had the distinct pleasure of interviewing Jessi Burg.

Outgrow Your Garage is working to increase the availability of business information for the trades and services by closing the educational gap for other small businesses, especially for industries that are so often underserved by the wider business world. As a values-driven business owner, Jessi Burg believes in proving that you can make a profit while breaking down class barriers. Through Outgrow Your Garage, Jessi is also able to support organizations that reduce recidivism through entrepreneurship.

Thank you for joining us in this interview series. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

I started my journey as an entrepreneur following a series of what I considered to be “toxic” work environments. After working jobs in seasonal industries for my whole career, I wanted to work somewhere I enjoyed and that aligned with my values, while also having a savings account. When I couldn’t find a company that suited my needs, I started my own. This allowed me to build my ideal work environment that valued employees, paid a livable wage, and successfully demonstrated a work/life balance, all while staying true to my core values.

My first company was a landscaping business that focused on edible and sustainable landscaping. For the five years I operated Pears to Perennials, I had near zero staff turnover and an 85% client retention rate from year to year. This attracted the attention of others in my industry, and I began teaching other companies how to refine their hiring practices.

In 2021, I migrated from Pears to Perennials to Outgrow Your Garage, which is a business development company specifically designed to help microbusinesses expand through a unique combination of online learning and virtual co-working. Outgrow Your Garage focuses on mobile trades and service businesses (such as painters, plumbers, and pet-sitters). These businesses cannot be done remotely and can only be scaled by hiring additional people. Some require specialized trade knowledge, while others can be started with a pick-up truck and a dream. Each course is tailor-made for business owners who are primarily working from job sites or from their car on busy days, ensuring that businesses can grow while handling their day to day needs.

You’ve had a remarkable career journey. Can you highlight a key decision in your career that helped you get to where you are today?

In 2015, I got laid off from the summer camp that I was working at because they discontinued the program I was working on. I decided to leave the seasonal industries, so I took my first year round office job. I hated it so much more than I ever expected to. I didn’t like my manager, I didn’t like showing up when there was nothing to actually do, and I definitely didn’t like the traditional white-collar work environment. So, I started my own landscaping business, which I might not have done had I not made that initial choice to try working in an office setting. That decision taught me a lot about what type of work environment I want to be a part of, which is especially true when it comes to hiring employees. The office manager and I did not align at all, and since starting my own businesses I’ve realized how important it is to align the hiring process with company values and staff engagement.

What’s the most impactful initiative you’ve led that you’re particularly proud of?

I am currently participating in the Women in Green Committee for the Associated Landscape Contractors of Colorado, which was established to address the recruitment and training of women for landscape industry careers. We work on finding out what the actual, real barriers are for women in the trades, and what the practical solutions to those barriers might be. One of the biggest ways we can mitigate the labor shortages that we are seeing right now is by providing proper work environments for women in the trades. Situational circumstances can make working difficult for women in male dominated industries, but if we actively address issues like childcare and lack of bathrooms (the two most commonly cited issues amongst women in male dominated industries) on an industry wide scale then we can make more of a collective change.

How about a mistake you’ve made and the lesson you took away?

I had an employee who just wasn’t living up to the company standards at Pears to Perennials. He was slower than the other landscapers and he didn’t pay any attention to detail. For our team dynamic to work and for the types of projects we were doing to go smoothly, he needed to have at least one of those traits to keep up. I waited way too long to fire him, and that impacted our bottom line, company culture, and overall staff happiness. It took me two more times of needing to let someone go to realize that waiting or procrastinating on it is not the way to do things. I gained clarity on how I want my staff expectations to be set up, and on how avoiding those hard conversations affects the entire company dynamic.

How has mentorship played a role in your career, whether receiving mentorship or offering it to others?

On the receiving side, it has been massive. I was lucky enough to participate in the Rocky Mountain MicroFinance Institute (RMMFI) business launch boot camp, which is all about helping entrepreneurs get their businesses up and running with an actionable plan and all the tools and support they’ll need. Part of this program included three individual mentors that helped me lay out a business plan. Having these mentors allowed me to launch my business a full year earlier than I planned. I had a lot of great support, and this program also then allowed me to become a mentor for other early stage entrepreneurs. It gave me a really good sense of how much I’ve grown and progressed as an entrepreneur, and now I can help other people do the same. I appreciate that this program came full circle.

Developing your leadership style takes time and practice. Who do you model your leadership style after? What are some key character traits you try to emulate?

I have had a lot of bosses, and at one point I was juggling 7 part time jobs. I try to model my leadership style after the things I’ve greatly liked and disliked in my past work environments. How do I make sure that my expectations are clear? How do I know what the end product looks like, and how do I efficiently relay that? How do I give enough information and have enough authority to make sure I don’t make those same mistakes with my employees that I experienced with former employers? I am adamant about being very clear on what is and isn’t okay, while still keeping in mind that the company is always growing and the team is learning while still adhering to our company’s mission and values.

Thank you for sharing that with us. Let’s change paths a little bit. In my work, I focus on helping companies to simplify the process of creating documentation of their workflow, so I am particularly passionate about this question. Many times, a key aspect of scaling your business is scaling your team’s knowledge and internal procedures. What tools or techniques have helped your teams be successful at scaling internally?

Outgrow Your Garage is specifically designed to help companies build out their internal operations in order to prepare for scaling. The real trick to scaling is to write down the things you’re already doing, and the questions you might have about what isn’t working. You need to have a clear vision of where you’re trying to get before you scale — you don’t know what you are going to need if you don’t first know where you’re going. Scaling is also a balance between what you need people to do and what they want to be doing. So, for example, if your company is growing and your employee’s job expectations are growing with that, make sure that the employee in that position has a desire to progress in that direction. Lack of communication during changes like this can bring the whole system to a halt.

The pandemic forced many companies to adapt. Implementing remote onboarding and professional development — in addition to maintaining culture — challenged organizations. Can you share with us the challenges you have faced, with remote onboarding and hiring? How have your internal processes evolved as a result?

Landscaping cannot be done remotely, so most of the training at Pears to Perennials had to happen on job sites. When part of the onboarding process moved to Zoom during covid, that shift was difficult in an industry where the field staff wasn’t always as into the latest technology, or didn’t always have access to readily available internet or computers. This made me think about Outgrow Your Garage in a different way, in that we want to make these processes more accessible, affordable, and applicable to everyone, especially underserved communities. We take into consideration how privilege affects the accessibility of much needed things, and are always trying to think of ways to make our business programming more accessible.

At Outgrow Your Garage, we also usually take the first 10–15 minutes of every team meeting to just kind of chat and catch up on the weekend. I try to bring some of that office conversation to our virtual meetings, as well as implementing a monthly team happy hour over Zoom! Company mission and values also spill over into after hours time, and that’s okay! Dedicating ourselves to a strong work-life balance means that we can have fun with our employees outside of work sometimes, too.

With the Great Resignation/Reconsideration in full swing, many job seekers are reevaluating their priorities in selecting a role and an employer. How do you think this will influence companies’ approaches to hiring, talent management, and continuous learning?

Putting potential candidates through a rigorous, multiple interview hiring process isn’t working anymore. No one appreciates having their time wasted, and many will back out if they think they’re getting dragged around. People know their worth, and these days they’re willing to find an employer who does too. A huge part of what we teach here at Outgrow Your Garage in terms of the interview process is what kinds of questions to ask to show that you are actually interested in how that candidate is going to fit into your company culture. They are interviewing you as much as you are interviewing them, and asking questions like, “What is your biggest weakness?” “Where do you see yourself in 5 years?” and “Why should we hire you?” makes it seem like you are less concerned with your company culture and finding a good fit for that, and more concerned about them as a commodity and how they are going to benefit YOU. That just isn’t going to fly in this climate, and candidates can sense that mindset easily. Instead, ask questions like, “What is your ideal work environment” or “What could your current company do to be more successful?”

Super, thank you for sharing all of that. Next, let’s turn to the main focus of our discussion about hiring the right person. As you know, hiring can be very time consuming and difficult. Can you share 5 techniques that you use to identify the talent that would be best suited for the job you want to fill? Please share an example for each idea.

  1. Have a clear job description and what your expectations are within the role you are trying to fill. If you’re hiring an entry level position, then make sure that your description matches that. Asking for 5+ years of experience for a low salary, entry level job is inappropriate. If you don’t ask for experience, be willing to teach. If you want an experienced candidate, be willing to pay more.
  2. Have a set of interview questions that give you the information you really want: What do you know about our company, and what made you want to apply? What is your ideal work environment? Tell me something about yourself that isn’t on your resume.
  3. Always include the direct supervisor in the interview processes. You want to make sure that the job that you’re hiring for and the person who is managing that position work well together. You don’t want any surprises when it comes to the expectations here.
  4. Be more inclusive, actively. Do you want to hire more women? Make sure that there is a woman in the room/helping to conduct the interview. Want more Spanish speaking employees? Make sure there is someone else who speaks Spanish in the room. Seek out their opinions on the candidates.
  5. Have a paid second interview. Every position should do this. Show the candidates that you are bringing back for a second round that you appreciate their time and are willing to pay for a second interview.

In contrast, what are a few red flags that should warn you away from hiring someone?

While this may sound obvious, pay attention to any sort of language presented by the candidate during the interview that doesn’t match your company culture. It’s easy to overlook someone’s personality if they have all of the skills that you are looking for. Fit is really important, and if they don’t fit into your company’s values, morals, and culture, then they are not the person you are necessarily looking for, despite experience or education. Do they interrupt in the interview process? Then they might not listen on the job. How are they conducting themselves? What does their professionalism look like? Were they late? Did they call to let you know? Consider these red flags in all interview candidates.

What software or tools do you recommend to help onboard new hires?

We recommend a really solid online payroll system, which you can utilize for onboarding. We use Gusto which we like a lot. We also utilize templates with a list of everything the new candidate will need for the interview onward. Keep your expectations clear, and COMMUNICATE! We also have a whole course on communication and how it can make or break your company. Communication is a two way street, do not forget that! Many unhappy employees have cited poor communication on the employer’s end as a reason for resigning. Use a software that helps you keep things organized if you need to, like a CRM or even a spreadsheet if that’s how you operate.

Because of your role, you are a person of significant influence. If you could inspire a movement that would bring the most amount of good to the most people, what would that be? You never know what your ideas can trigger.

To pay a livable wage per area to entry level workers across all fields and all sectors. Whether that be house cleaners, McDonald’s workers, receptionists, or retailers, I’d like everyone to receive a wage that allows them to live in a one bedroom apartment by themselves, no matter where they live. Every single job should pay at least that.

This was truly meaningful! Thank you so much for your time and for sharing your expertise!

About the interviewer. Ken Babcock is the CEO and Co-Founder of Tango. Prior to his mission of celebrating how work is executed, Ken spent over 4 years at Uber riding the rollercoaster of a generational company. After gaining hands-on experience with entrepreneurship at Atomic VC, Ken went on to HBS. It was at HBS that Ken met his Co-Founders, Dan Giovacchini and Brian Shultz and they founded Tango.



Ken Babcock, CEO of Tango
Authority Magazine

Ken Babcock is the CEO of Tango with a mission of celebrating how work is executed. Previously worked at Uber, Atomic VC, and HBS