How to Build a Winning Team

How do you motivate your employees to be their best? Start with being the best leader you can be.


One of the best ways to build your business is to invest in team members who can help you bring your vision to life. More hands on deck usually means faster, more efficient and sustainable growth. The key to how to build a winning team is to bring on the right “hands” and become a leader that empowers them to contribute in a robust way.

How do you hire the right people for the right roles? It starts with defining your company culture and ends with being the kind of leader that high-quality employees want to work for.

Let’s walk through some of the best practices associated with building a top-notch team.

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Define Your Company Culture

Defining your company culture is a little like defining your brand, but focused inward. It’s a set of values and beliefs that drive every aspect of how you and your employees run your business. When you’re clear on your culture, you’ll be better prepared to know a good fit for a team member when you see one.

It’s also important to be aware that each new person on your team may bring their own set of values and beliefs. This is something to welcome because it can enhance your culture and help it evolve. Different perspectives and healthy friction can help your business grow into a dynamic organization that thrives on change. Some people look at this as looking for employees who can bring “culture add” to the table versus “culture fit.”

Value Diversity

Be open to challenging your own perception of the work you do, the customers you serve, and the very vision and mission you have created. A diverse, equitable and inclusive workforce will allow you to do this more powerfully than anything else. Bring in people who look different than you do, think differently than you do and even behave differently than you do.

Observe how they interpret the actions of your customers, perceive their pain points and think about the work you do. People who are different than us have different lived experiences and bring a wealth of information that we wouldn’t otherwise know or understand. You can still be a leader who is in “control” of your business; you’ve just hired some allies that will help you understand and accommodate new perspectives.

Look for People Who Want to Grow

While it’s not great for any company to have a status quo worker, it’s especially disastrous for a small business. When you’re looking to grow your operations, every person’s actions count. That’s why it’s important to look for people who have aspirations to build their resume. They may be applying for an administrative assistant job now, but they want to take on more responsibilities so they can grow their career. (This might mean you’re hiring another assistant in a year or two, but there are a lot of big thinkers willing to start at the bottom, especially recent graduates.)

The best way to retain a motivated employee is to create conditions for them to shine. Once they’ve mastered the duties they’ve been hired for, look for other ways for them to contribute. And make sure they feel acknowledged and empowered to keep striving for more. It helps to publicly and privately recognize their efforts and make sure their pay is at the top of what you can afford. A high-performing employee can take your business to new heights.

Work on Your Leadership Skills

If you’re lucky enough to attract great employees who are willing to learn and grow, you owe it to them to do the same, as a leader. Among some of the qualities of great leaders is the ability to:

  • Empower others to do their best work
  • Be willing to listen and create a safe environment where employees can be themselves
  • Have a strong vision that others can relate to
  • Foster strong connections among team members
  • Mentor employees

Some people are instinctively skilled at leading, while others have to work at it. Either way, it’s helpful to study and practice leadership. Be open to reading leadership books, listening to leadership podcasts and taking in-person and online leadership training courses. It’s the kind of thing that pays off in huge dividends.



Communicate Clearly

Imagine being a crew member of a large ship headed out on a fantastic voyage to bring back mountains of gold. To do your job well, you would need to know:

  • Where you’re going
  • How long the journey is expected to take
  • The goals of the operation when you arrive
  • Who is going to do what
  • How, exactly, your role contributes to the main goal of bringing back the gold
  • What happens when the gold is brought back

A strong vision has to come with a clear path forward. That doesn’t mean data dumping on your team members with minutiae in your weekly meetings. Rather, communicating a handful of priorities and connecting them to your overall vision will go a long way toward ensuring everyone knows exactly where the ship is headed and what they can do to ensure a successful mission.

Create an ‘Us’ vs. ‘Them’ Mentality

In regular society, this is not a great strategy to navigating the world. But when it comes to building winning teams, a sense of cohesion and purpose (even rivalry) can go a long way. In fact, thinking of your employees as members of a sports team helps put things in perspective, for them and you.

If you’re the coach of a sports team, you provide the support and strategy to bring your team into the number one position against your competitors. Each player on the team has a role to play in the victories, large and small. You may lose a few games from time to time, but it only makes the team stronger and more motivated to be their best. To really sell this system, you could gather metrics of your competitors and provide a clear line of sight to how you measure up.

Set a Respectful Tone

Nothing makes an employee feel more discouraged than a boss who doesn’t respect them. That often comes in the form of questioning their judgment, micromanaging their work, publicly reprimanding them, blaming them for mistakes they didn’t make and just generally making their work life unpleasant. Obviously, a winning team isn’t created by leaders who are disrespectful and unappreciative.

Most successful leaders go out of their way to create a respectful workplace where an emphasis is put on positive, productive interactions. Being clear about the importance of respect in the company’s vision and values is a good start, but that won’t work if you don’t model the kind of behavior you want to see in your employees. If someone is negative or gossipy, you will have to manage it swiftly and clearly so other team members feel safe and supported.

Hold Team Members Accountable

In larger companies it may be possible to come up with great ideas and just never get around to actually doing them. In a small business, you want team members who are doers as much as they are sayers. It’s helpful to encourage great ideas and support your employees to carry them out. Make it clear that your expectation is that everyone pulls their weight and is accountable to you—and their colleagues—for doing their part.

This is important to building trust among team members. If they know they can rely on one another to get things done, they can work efficiently and without friction. Depending on the nature of your business and the types of roles you employ, it may be helpful to conduct regular performance reviews and connect them to bonuses or pay increases.

Offer Regular Feedback

Employees generally thrive on feedback—even if it’s negative (and delivered in a constructive way). As a leader, it’s your role to make sure your team knows if they’re doing everything right or if they could stand to improve.

Performance reviews are good times to be specific about how employees are doing their job, but they’re not usually held regularly enough to be truly helpful. It’s advisable to offer feedback in two ways:

  • On the fly: Make it a habit to tell an employee they did a great job on something when you notice it. Be specific about what made it great, i.e., “That was a tough situation with a customer who was clearly unhappy. You did a great job resolving the problem because you stayed calm, positive and focused. Well done!” Same goes for a situation that they could have handled better.
  • At regularly scheduled intervals: Have regular face-to-face meetings with employees to go over projects and to provide feedback. If an employee needs to improve an aspect of their work, it’s helpful to check in regularly and mentor them until they get it.

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Reward Performance

Of course, it’s not enough to tell your team how great they are. It’s just as important to show them the money. Small businesses tend to be cash-strapped, but if you have your eyes on growth, you’ve got to consider bringing on an employee as a significant investment in your company’s future.

Even if you can’t afford top-of-the-line pay, be as reasonable as you can and look for other ways to reward performance. If the company does well for a quarter or two, share the wealth to help motivate employees to strive even harder to make the business a success. Another way to give your team a boost is to provide opportunities to learn and grow. That might be on-the-job mentoring or job shadowing. Or you might spring for more formal online or in-person training that will help them in their current role and also elevate their overall resume.

Encourage Camaraderie

It’s one thing for you to be likable to your employees—and something else for them to like one another. As a leader, you have a lot of control over how colleagues relate to one another. It certainly starts with establishing a company culture and valuing respect, but it can evolve into something special if you create the conditions for employees to forge their own bonds.

A simple (and unimaginative) way to get people talking is to do the mandatory birthday cake celebration in the break room or a monthly pizza lunch. If your team is easygoing and up for anything, that might do the trick. But you can do better than that by simply observing your employees and asking for input on activities they might like to do together. Maybe it’s a day of volunteering at a local animal shelter or hosting a trivia night with their partners. Other workplaces might prefer putting together a book or movie club. The key is to customize the activities to the people who will be participating in them.

Wrapping Up: Build a Winning Team

Building a winning team takes more than having the right intentions. It means shifting and growing your responsibilities as a small business owner to include leadership priorities. This often means acquiring a whole new skill set—and mindset. It can also bring a new sense of purpose to the work you do.

It all starts with a clear vision and the willingness to listen, grow and learn. Look for team members who are enthusiastic to do the same.

This post was updated in April, 2020.



about the author

Freelancer & FreshBooks Customer Heather Hudson has been a freelance writer for more than 17 years. As a small business owner, she understands the triumphs and challenges of life as an entrepreneur. And as a longtime FreshBooks customer, she’s always looking for ways to work smarter, not harder. You can learn more about her work at heatherhudson.ca.