Teambuilding Tips and Techniques for Entrepreneurs

Building a strong team is essential for any entrepreneurial endeavor. Whether you’re managing W-2 employees, 1099 contractors, or a combination of both, the right team dynamics can propel your business to new heights. Successful teambuilding isn’t just about finding the right people; it’s also about creating a supportive environment where everyone can thrive.

Understanding Your Team Structure

Every business has a unique structure, and understanding yours is the first step to successful teambuilding. Whether you’re working with traditional employees or independent contractors, each group has different needs and expectations.

W-2 Employees: They often look for stability, benefits, and a clear path for growth within the company. Your approach should focus on creating a supportive work environment, offering development opportunities, and establishing a strong company culture.
1099 Contractors: These team members are typically more autonomous, valuing flexibility and variety in their work. For them, it’s crucial to set clear expectations, provide adequate resources, and foster a culture of mutual respect and collaboration.

Determining whether a team member should be classified as an employee or a contractor isn’t just a business decision—it’s a legal one. The IRS has strict guidelines to differentiate between employees and contractors, focusing on the degree of control you have over their work, the financial relationship, and the nature of the job. Misclassifying workers can lead to penalties, so it’s important to assess each role carefully.

Here is some of the current guidelines by the IRS (always check for yourself and these may be updated periodically):

Behavioral Control: Does the company control or have the right to control what the worker does and how the worker does their job? This includes instructions, training, and evaluation systems.
Financial Control: Does the company control the business aspects of the worker’s job? This includes how the worker is paid, whether expenses are reimbursed, and who provides tools/supplies.
Relationship Type: Are there written contracts or employee-type benefits (e.g., pension plans, insurance, vacation pay)? Will the relationship continue, and is the work performed a key aspect of the business?
Nature of Work: Is the worker performing tasks that are a core part of the business’s primary services? If the work is integral to the business, it may indicate an employee relationship rather than an independent contractor.

For detailed guidance, you can refer to the IRS page on Independent Contractor (Self-Employed) or Employee?

Creating a Culture of Collaboration

No matter the business model, fostering a collaborative culture is key. The culture you cultivate within your business will significantly influence how your team operates and how effective your teambuilding efforts are. Culture isn’t just about having a friendly work environment; it’s about setting the tone for how work gets done, how people interact, and how problems are solved.

Consider the culture you want to create for your team. Do you want an environment that prioritizes innovation, encourages open communication, or emphasizes work-life balance? The culture you establish will guide your hiring decisions, influence your team’s morale, and impact how team members collaborate with one another.

Company culture is related to every piece of your business, so you need to carefully consider it as part of your teambuilding as well.

Encourage open communication and make sure that all team members feel heard and valued. Regular team meetings, both in-person and virtual, can help ensure everyone is on the same page.

Additionally, recognize that culture can either unify your team or divide it, depending on how intentionally it’s built and maintained. A positive, inclusive culture will lead to stronger teamwork, higher productivity, and greater job satisfaction.

Onboarding: Setting the Stage for Success

The onboarding process is your opportunity to set the tone for a new team member’s experience within your company. The time and effort you invest in onboarding will pay off in the long run, as it helps new hires integrate into the team, understand their role, and align with your company’s culture and goals.

Failing to onboard well is one of the biggest mistakes many businesses make. Think about how you would have wanted to be treated in your first day, first week, first month as a new hire at any company. Simply being thrown in a room and expected to figure it all out on your own is probably not what you would want.

During the initial stages, spend significant time with your new hires through one-on-one meetings, coaching sessions, and hands-on training. This is where you lay the groundwork for their success by clearly communicating expectations, providing the resources they need, and starting to build a relationship based on trust and support.

Onboarding Plan:

Pre-Start Preparation: Ensure that all necessary equipment, software, and access are ready before the new hire’s first day. Some large corporations cannot have some final pieces set up until after the employee is officially on the job, but whenever possible have everything ready so that they can hit the ground running.
First-Day Welcome: Make their first day memorable with a warm welcome, a tour of the office (virtual or in-person), and an introduction to the team. When possible, I liked to also provide them with relevant swag – a set of business cards (even if it’s a small set), nametag, name plate, tshirt and mug … whatever I have available to make them feel like they are already part of the team.
One-on-One Meetings: Schedule regular one-on-one meetings to discuss their progress, answer questions, and offer support. Also schedule similar meetings between the new team member and other employees, especially those that can help mentor in different areas.
Training and Development: Provide comprehensive training on your company’s systems, processes, and culture. Include both technical skills and soft skills development. Make a list so that nothing is forgotten.
Initial Goals: Set clear, achievable goals for the first few weeks and regularly review progress. These don’t have to be huge metrics, sometimes it’s simply about getting to know coworkers and the business.
Feedback Loop: Establish an open feedback loop where new hires feel comfortable sharing their experiences and any challenges they face.

Maintaining Engagement with Existing Employees

Once your team is established, maintaining engagement and continuing to build your team’s cohesion is crucial. This requires ongoing effort and attention.

Continuous Engagement Plan:

Monthly Individual Meetings: Meet individually with each team member once a month to discuss their progress, challenges, and career development. Make sure that they understand these are opportunities for THEM to get help from you … not for you to tell them everything they are doing wrong. These are teambuilding, not correction meetings.
Weekly Team Meetings: Hold weekly team meetings to ensure everyone is aligned on goals, projects, and any issues that need to be addressed.
Be a Coach, Not a Boss: Shift your role from manager to coach. Provide guidance and support rather than just assigning tasks and demanding results. Help the team by being able to remove things that are blocking their progress, and provide them with resources and connections. This approach encourages team members to take ownership of their work.
Professional Development: Encourage continuous learning by offering opportunities for professional growth, such as workshops, courses, or mentorship. When the business can pay, even better.
Celebrate Wins: Regularly recognize and celebrate individual and team accomplishments. This boosts morale and reinforces a positive culture. Remember to praise in public … anything remotely negative should only be done in private.

What Doesn’t Help with Teambuilding or Employee Morale

When it comes to teambuilding and boosting employee morale, not all efforts are created equal. Some well-intentioned activities can actually deflate morale, leading to disengagement rather than fostering a cohesive team. Here are some common pitfalls to avoid and suggestions for more effective alternatives.

And realistically … you know when this crap is lame. So if you know it’s lame, why would you do it?

The “Lame” Pizza Party

What Doesn’t Work: Throwing a pizza party or similar small-scale events with no thought put into the incentive or food in lieu of meaningful recognition or financial rewards can come off as tone-deaf, especially if employees are struggling with workloads, stress, or feeling underpaid. These gestures can feel superficial and fail to address the real needs of your team.

Let’s be real … your employees work there to be paid. No matter how much we might HOPE that they come spend 8 or more hours with us every day, honestly it’s because we PAY them to. And if you provide for a mandatory meeting, or even as a surprise, putting zero thought into it by simply ordering pizza every time, also says something about how much thought you put into your employees in general … which in this case would be not much.

What to Do Instead: If budget constraints make raises difficult, consider more personalized recognition, like a thoughtful thank-you note, or better yet, public acknowledgment of an employee’s contributions. When possible, offer flexible perks like additional time off, professional development opportunities, or small bonuses that genuinely reflect your appreciation. This approach shows that you value their hard work and are invested in their well-being.

And when you DO provide a “food” based party … make some level of effort to provide the type of food that your employees might actually appreciate. If your goal is “whatever is easiest and cheap for me” … then maybe you shouldn’t actually be doing a food party at all.

Lame Teambuilding Activities

What Doesn’t Work: Forced fun, such as awkward icebreakers, trust falls, or mandatory after-hours activities, often backfires. Employees may see these as a waste of time or, worse, an intrusion into their personal life. These activities can feel forced and may increase discomfort rather than camaraderie.

Do you remember when you were working for some other corporation, and they’d schedule a day of teambuilding activities? I bet you can feel your eyes rolling as you read this. Ugh. Most employees are NOT fans of these mandatory teambuilding days, so you need to consider carefully. Some of them do a great job actually enhancing teamwork … others serve as a demotivator.

What to Do Instead: Choose teambuilding activities that align with your team’s interests and work style. Theirs, not yours. Collaborative problem-solving activities, workshops that build on actual work skills, or even volunteering together can be more meaningful. For a fun and engaging option, consider activities that encourage creativity, like a virtual escape room or a team-based project that benefits the company, such as brainstorming a new product idea, or if it fits with your company culture maybe something that benefits the community.

Remote Teambuilding: Making It Work

What Doesn’t Work: Virtual happy hours or other informal remote activities that don’t resonate with your team’s preferences can lead to low participation and a feeling of disconnection. Remote employees often have different needs, such as more flexibility and clear communication, which these activities might not address.

What to Do Instead: For remote teams, focus on activities that foster real connections and collaboration between team members. Schedule virtual coffee breaks where small groups can chat informally, or host “show and tell” sessions where team members share something they’re passionate about outside of work. Encourage participation in online training or development programs where employees can learn together.

Also, regular one-on-one check-ins with a focus on personal as well as professional topics can help build strong remote relationships.

And for the love of everything … if you ping them on whatever communications platform, don’t start berating them if they haven’t answered you within five minutes! There are needs such as bathroom breaks and grabbing a cup of water. Be realistic in your expectations for your remote workers.

Understanding Motivation vs. Deflation

What Doesn’t Work: Assuming that what motivates one person will work for everyone can lead to morale issues. For example, offering generic rewards or recognition programs may miss the mark if they’re not tailored to individual preferences or needs.

Similarly, imposing rigid work structures without considering the team’s need for flexibility can decrease morale. Just because it’s how you prefer to work or receive motivation doesn’t mean it’s what everyone else prefers, and the best bosses (who create the most loyal workers) understand this. Granted, your company culture may be “every employee must conform to what your boss wants even when it doesn’t matter to the company” … but probably not.

What to Do Instead: Take the time to understand what truly motivates your team members. Some might value financial rewards, while others appreciate public recognition, growth opportunities, or work-life balance. Use regular surveys, suggestion boxes, or informal check-ins to gauge what matters most to them as a whole. Use direct communication to determine it for each individual.

Tailor your approach to acknowledge these preferences, and make sure your strategies are flexible enough to adapt as team dynamics and individual circumstances change.

Building and maintaining a strong team is one of the most important aspects of entrepreneurship. Whether you’re managing a team of W-2 employees, 1099 contractors, or a combination of both, the principles of collaboration, culture, trust, and continuous learning remain the same. By focusing on these areas, from onboarding to ongoing engagement, you’ll be well on your way to creating a team that not only supports your business but drives it to new levels of success.