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Dorchester Center, MA 02124
If you’re here, you know the feeling of being stretched thin, juggling a million tasks, and wishing we had a team that didn’t just follow instructions but took real ownership in their roles. Imagine the difference it would make if your team could problem-solve, take initiative, and step up in ways that make a tangible impact on the business. Here’s the good news: leadership is a skill that can be nurtured. Developing leadership abilities across your team—whether they want to grow within the business or simply excel in their current role—can make a huge difference.
This article dives into practical, small-business-friendly ways to cultivate leadership qualities within your team, regardless of their job titles. Strong, engaged team members drive success, and it’s up to us as owners to create the environment for that success to happen.
Creating leaders within your small business isn’t just about preparing someone to “move up.” It’s about building a team of people who think independently, handle challenges confidently, and contribute to a positive work environment. In every type of small business—from retail to service industries—investing in leadership skills within your team has tangible benefits:
I’ve seen this firsthand. A few years ago, I was either managing or knew about every small decision in my business, and it was exhausting. Once I started actively involving my team in decision-making and encouraged them to find their own solutions, I saw a huge difference—not just in my workload, but in how confident they were in their roles. This can be easier said than done! If you have a fear-based culture, where everyone is afraid to make a wrong move- you have some work ahead of you! It’s important to change this so that everyone feels empowered, enabled and SAFE. Leadership qualities can absolutely be cultivated, and the payback is more than worth it.
It’s easy to think that only certain people are “meant” for leadership. In reality, many of the best leaders aren’t the loudest or most obvious candidates. Look for qualities like reliability, adaptability, and a strong commitment to quality. Someone who quietly ensures that things run smoothly without needing constant supervision is often displaying more leadership than you realize. Look at the people who naturally put people at ease and who people naturally want to follow. There are a fair amount of skills you can learn, but several successful leaders have natural abilities to start.
Leadership qualities can show up in surprising ways. Over the years I have seen great leaders and I have seen ones that, although usually have good intentions, can bring down the business and everything around it. When trying to spot one, watch for actions and characteristics like:
Offer opportunities for team members to try out leadership on a small scale. Often time our employees won’t think of themselves as “good enough” or “able”. Sometimes they need to be encouraged and recognized that they are enough and that we believe in them! These could be low-pressure scenarios like leading a quick team huddle, managing the shift schedule, or even taking on a customer complaint. These “leadership try-outs” give team members a taste of responsibility and help you spot those who may have more potential than they realize. These things are truly a muscle to flex and the more we expose them to opportunities to flex that muscle, they will continue to get STRONGER!
Effective delegation means looking beyond the task and thinking about the growth opportunity. For example, letting an employee design a new store display or oversee an inventory audit gives them a chance to use their skills in a meaningful way. It’s not about adding more work; it’s about letting them take ownership of something small but impactful.
Time for some self-reflection: are you capable of letting go of the control to fully allow someone else the opportunity to grow? What if this employee or co-worker doesn’t do it right? What if I won’t know all the details? What if I won’t be needed anymore? There are all kinds of fears we can let ruin this great opportunity. But with it comes a little risk – you have to risk it not being perfect and maybe it not being done the way YOU would have. This doesn’t make it wrong, it makes it different, and the reality of the situation is you have to let go in order to move up or move on. If you can’t trust your employees, you will never grow!
When I first started delegating tasks to my team, I was nervous about letting go. But each time a team member successfully took on a responsibility, their confidence grew—and so did mine. Now, they often anticipate what needs to be done without me even asking, which has freed me up to focus on long-term growth and strategy.
One of the most valuable leadership skills is the ability to solve problems independently. Rather than always jumping in with a solution, take the time to guide your team members through the process of finding answers themselves. This builds their confidence and reinforces that they have the ability to solve issues on their own.
Let’s say a team member comes to you with a customer issue. Instead of handling it right away, ask them questions that lead them to find a solution, such as “What do you think would make the customer happy?” or “How could we resolve this and prevent it from happening again?”
Peer relationships can be a fantastic training ground for leadership. Encourage experienced team members to mentor newcomers, whether it’s showing them the ropes or sharing their own tips for success. This builds a sense of community and accountability within the team. Over time, I’ve found that these peer mentoring moments create a stronger, more cohesive team.
Providing leadership training doesn’t mean you need a massive budget. Bring in a local expert for a workshop, encourage employees to use online tutorials, or set up shadowing days where they can learn from others in different roles. This creates an environment of learning and shows employees that you’re invested in their growth.
A mentorship program doesn’t have to be formal. Pair team members with others who have skills they want to develop. For example, let a junior employee shadow a more experienced colleague to see how they handle customer interactions or organize their workflow. It’s a simple way to build skills without extra cost.
Feedback doesn’t need to be formal or lengthy; quick, positive reinforcement can be just as effective. Make it a habit to give regular, candid feedback to all team members. Recognize their strengths and areas for improvement in a supportive way, so they know they’re valued and have opportunities to grow.
By creating an environment where leadership qualities are valued and nurtured, you’re building a resilient, adaptable team that feels engaged and empowered. Every small investment in their growth makes a big difference to your business’s strength and stability.
Challenge: This week, think of one small opportunity where you can let a team member take the lead. Whether it’s organizing a team lunch or handling a special project, give them a chance to shine. The rewards—for both of you—will be worth it.