How to hire and create a winning team

One of today’s top challenges for many entrepreneurs is how to hire and create a winning team. Putting together a dynamic group of employees who are passionate about the mission of their company is crucial for success! It can also be very expensive.


Many small businesses lack the resources to pay for expensive testing to determine a potential employee’s fitness for the opportunities available. Same applies to paying recruiters to find you the “perfect” placement.

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The advertising, interviewing and training investment you make in each new employee is substantial, costing time, energy and money. If you want to build a top notch team but have a small business budget, you likely can’t steal away the current experts in your field to work for you. When you invest in a new employee, you want to retain the individual to reap the benefits of your investment while offering them unique opportunities for growth.

Yet to those of us who started our operation on a shoestring budget, bootstrapping everything we could, the idea of a “hiring process” seems almost too standard a procedure to use in our fluid entrepreneurial environment. It’s not always possible to maintain an entrepreneurial mindset alongside more traditional corporate hiring practices.


In the early days of my company, when I was its only staff, it was difficult to plan ahead for the time I would hire my first employee, much less an entire team. I was too busy trying to survive. As my company grew, so did my need for help.

My constant question was how and where I would find the people I needed with the knowledge and passion necessary to do the job… at what I could afford to pay.

Even when you are in a desperate situation, don’t make a move toward identifying and hiring your first employee until you’ve defined the overall vibe you want your business to exude. It’s much harder to do so once you’ve hired and have employees in place.

This can make or break everything. The team you put in place becomes part of your foundation, especially in a small business. As difficult as it sounds, you have to know your tribe before you build it. It’s easier than you might think.

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First, determine what personality type you work best with. Look at other areas in your life, at relationships. Then think about your own shopping or service experiences. Think vacation. Anyone who’s taken a vacation has stepped into a gift shop or received some kind of service for the first time. Some of them make impressions lasting a lifetime. Others are completely forgettable. Make a list of the things you like most and least when you’re the customer. Use that information to create standards for your own business, as a blueprint for your personal vibe. Write down what you find out, to keep you mindful of and focused on the intentional creation of the workplace culture you desire. You can easily design your specific, written employee guidelines later using these initial benchmarks.

As a retailer, mine included the following criteria:

  • What type of dress is acceptable given your type of business? A potential employee must be willing and able to meet a basic dress code. My guidelines called for jeans without holes and t-shirts. Shirts could be branded but not carry a message. Shorts were fine too, but must reach mid-thigh. Because we unloaded pallets of inventory five days a week, closed-toed shoes were required.
  • What are your values? Honesty, willingness, compassion, teachability and a desire for serving others were at the top of my list.
  • What is your concept of customer service? I am extremely particular regarding this provision. I’ve had great interviews with people who exhibited everything I liked to see, but couldn’t master the social aspect of retail.
  • What kind of learner are you? Written, verbal or experiential? The more staff you add, the more important this becomes.
  • How do you normally solve problems? What happens when the problem becomes a verbal conflict? How do you handle unhappy people?

These are just a few considerations I made before hiring. Understand the requirements you have of an applicant prior to making your first hire will help you build a strong, loyal team of employees with a clear understanding of your needs.


Faced with a need to hire your first employee while keeping in mind your end-goal of building a team you will one day lead, a savvy entrepreneur looks for and hires people who exhibit raw talent and the willingness to learn. Where to find them quickly becomes your new challenge.

Start by looking at the people close to you. I spent almost all my time at work, helping customers while slowly building my company. In the process I came to know a variety of people, many of whom became passionate supporters of my business. It naturally followed I would look to this group first when I hired.

No matter what population you draw from, it is important to evaluate and select the best candidates for your specific industry. Particularly when you choose candidates from your customer base or decide to hire someone who works for a local competitor, use caution. These people may also be influencers, able to directly impact your profitability should the employment relationship sour.

One tool I use is a simple criteria list. The list helps me narrow down who I should approach while reducing the overall number of potential hires. I look for basic things when assessing a person’s readiness and approachability:

  • Do they look you in the eye during conversations?
  • Can they assimilate and recall information? Try a little mirroring exercise to determine their abilities in this area. Ask, “Do you remember our conversation earlier when we talked about _____? How did the information help you at the time?” Simple, unassuming questions give you a clear understanding of how they process information. It also gives you a chance to evaluate their delivery of information.
  • How do they stand? Erect or slouched? In a physically demanding environment, physical core strength is important. Slouching may also indicate low self-esteem. A person’s posture shows more about herself than they might imagine.

In the end, you have to decide based on ALL the information you gather, the challenges you can work around when hiring. Once I decide to offer someone a position, they are subject to a 60 trial period. During that time, if either of us felt they weren’t the right fit or the job was not as they’d expected, either of us could end the employment relationship, no harm done.


Once you’ve found your perfect new hire and they’re ready to come on board, what can you do to set both you and them up for success?


From your first hire to your last, look for people you already have a good relationship with, who understand what your company does and why. I recruited most of my top talent this way.

It’s important for both parties to keep in mind the changes that must take place in your relationship when hiring someone you know. Boundaries change when a customer/business relationship becomes one of employee/employer. Roles must be redefined clearly. Methods of communication also change. What might have been a very fluid relationship is now more structured.

After several mistakes and losing two key people, I learned it is necessary to have these issues addressed in writing as part of an employee handbook, operational guidebook or in a form suited to your particular type of business. Bottom line, get clear on what you need as an entrepreneur and employer before hiring.

You’ll make changes to your operating guidelines over time. Your first concern is easing the transition from customer to employee. The smoothest transitions are made when both the person hiring and the candidate being hired are on the same page. In time, you will create an extraordinary team of employees who love what they do and the people they work with.


Training a new employee isn’t as daunting as it may sound. A new employee is going to have deficits, skill sets they haven’t developed yet or have no aptitude for. From the first day, communicate consistently with your new hire, their mentor, and the rest of your team. During their first few weeks, check in daily with the mentor you’ve assigned to get feedback and keep your new hire’s training on point. Your concern should be how can you set them up for success.

  • First, as the owner or CEO, introduce your new hire to the rest of the staff or your team. They need to feel welcome and as comfortable as they can be on their first day of work. Once they’ve met the team, as the day goes on, introduce them to customers. The best way to build a new relationship is taking the first step to creating it by facilitating communication. Plus, your new hire will immediately start to feel part of your team.
  • Partner your new hire up with a seasoned employee whose strengths best match the needs of your new employee. This mentorship begins with an understanding of what you as the employer expect from a mentor. Provide a list of what you’d like your senior employee to focus on while mentoring a new hire. A mentor can act as sounding board, offering suggestions and advice to the new hire, as well as direct training.
  • Keep it simple. Don’t overwhelm your new hire. Start training on the basics first, for example, teaching them how to answer the phone or emails. If you have a standard greeting, ensure they’re aware of it by putting it next to the phone or providing an email template. You might also provide a list of the most commonly asked questions, with answers.
  • Teach them to greet people, the way you want them to be addressed, as they come into your business or contact you online. This is the first impression most customers will have with your business, so I was particular about this skill.
  • Test their technology skills on the first day, whether it’s running a spreadsheet or using your company’s software. Measure their starting baseline. Most people catch on quickly. Some take more time and a few just can’t get tech. If you have hired someone who cannot get the tech side of the job, you’ll have to determine if there is another position in your organization they can fill or if, despite the thoroughness of your interview process, your new hire simply isn’t a good match.
  • Have a basic guide to the products you carry or services you provide, why they are unique and any selling points. This is especially important if you specialise in a certain service or product market. For example, I owned natural pet food stores and the learning curve for a new employee was at least six months. Don’t set your expectations too high. Everyone learns at a different pace.

These are but a few training strategies. Consistent communication between your new hire, their mentor, your existing team, and your customers, will help you quickly identify and act on any potential training challenges.


Make it a practice with all your employees, whether you have one or 1,000, to notice and appreciate what they do well. Touch base with them often to strengthen the relationship you’ve worked so hard to develop. An appreciated employee is more likely to speak up when she knows they’re a valued part of your team, even as a new hire.

Happy, motivated employees communicate openly, making an easier time of addressing areas in need of improvement. A team of employees who know the business owner respects and considers their opinions, will give their much-needed feedback during a hiring cycle.


Once hired, set your new employee up for success by using these techniques. Work to build relationships, provide strong mentors, offer a well-designed training program, manage expectations and keep channels of communication open.

In doing so, you create a rock-solid foundation on which your business will continue to grow. Well-trained, bound together by a common desire to serve customers and the larger community, this incredible team you built will shine!

Robin Aldrich is the founder of Robin Aldrich, LLC, Healthy Hound, Inc., and the Boomerang Business Project. A U.S. Navy veteran, she offers 30 years of military, nonprofit and business leadership to her clients. With a focus on Servant Leadership, building Entrepreneurial Mindsets and Personal Development, she consults with corporations and individuals passionate about building strong relationships, both personal and professional. She is published on Addicted2Success,Thrive Global and Medium.