The Entrepreneur’s Path: Building Stronger Teams and Businesses

A hypothetical scenario to highlight challenges and triumphs on an entrepreneur's path to building stronger teams and businesses.

As a lead facilitator and trainer for the conflict resolution group JAMS Pathways, I have worked with entrepreneurs facing challenges at various stages of their business growth. Entrepreneurs bear tremendous responsibility, working hard to maintain high standards and develop an office culture where everyone is invested in the company’s future. Despite their best efforts, there are always obstacles to overcome. To illustrate this, let’s discuss a hypothetical scenario featuring Justine, an entrepreneur whose journey exemplifies the struggles and successes of growing a business. This exercise will explore Justine’s story and the lessons learned.

Justine built her business into a powerhouse. It took ten years to grow her company to 17 employees. Her staff has grown from 17 to 70 in the last three years. The press took notice, and so did investors. Justine traveled for weeks at a time, but everyone seemed happy when she was in the office. Then, it all went wrong.

Wanji, an award-winning designer, was recently promoted to managing designer. He was the leader of an important project. Everything started fine. Wanji was excited about the opportunity, and the client seemed happy. A month later, Justine noticed that employees on Wanji’s team were turning off their cameras in virtual meetings, avoiding staff socials, and even avoiding eye contact in the halls on in-office days. It was odd. The project missed a milestone. The office manager reassured Justine that some on Wanji’s team had called out sick lately, but the project was getting back on track. Justine emailed Wanji, who confirmed.

Two months later, the team was close to missing another milestone. The client called Justine to complain. Justine confronted Wanji herself. He told her there was miscommunication on his team and that he was working it out. Around this time, someone posted anonymously on an industry Reddit about the toxic work environment in their office. Justine was floored. That’s when she sought help.

In private conversations, Justine expressed her confusion and frustration. Why hadn’t anyone come forward with their complaints? Didn’t her employees know that they can always come talk to her? To address these concerns, we worked closely with them to identify their needs and develop a comprehensive plan. We provided communication training to equip employees with the tools and confidence to effectively voice their concerns and address tensions. We also facilitated a companywide forum where everyone could openly air their grievances, identify underlying needs, and collaboratively generate solutions. As a part of Wanji’s performance improvement plan, one of the experienced managers, Theresa, shadowed him. She observed that his instructions could be unclear, and his communication was occasionally belittling and problematic. He needed training and mentorship. Rebuilding trust takes time, but this company was on its way.

Three interventions put them on the road to stronger teams through support for new managers, a collective approach to problem-solving, and communication skills training for all employees.

Support for New Managers

Managers are often promoted because they are good at their jobs, not because they excel at managing people. Wanji is an excellent designer but struggled in a leadership role. He micro-managed his direct reports and expected the benefit of the doubt, no matter his tone or comments.

New managers and directors need support through a systematic onboarding process. The onboarding plan should educate them about their responsibilities, impart expectations and standards, and provide training that includes:

  • How to manage performance and provide feedback
  • How to have difficult conversations
  • How to develop leadership skills that propel the team forward
  • How to create an atmosphere of psychological safety

Systematic onboarding plans help new leaders understand their responsibilities and recognize when they need help and how to ask for it. Training imparts integral tools they can apply to anticipate and address problems. For larger organizations, this process creates a natural peer cohort. Best of all, these essential lessons continue to yield results as they advance in the organization.

Utilizing Your Team for Problem-Solving

Justine thought she created an environment where staff could speak up without the formalities of retreats or facilitated dialogues. She learned that employees focus and connect when there’s a dedicated space for these conversations.

Creating a space for team dialogue strengthens trust. Each full-time employee invests over 1,800 hours per year performing their role. They become experts in what they do. They see gaps in systems. They see opportunities for growth and innovation. When we offer staff/experts a chance to contribute to a broader discussion, we recognize that their opinions are meaningful to the company.

Second, these spaces help leadership to understand each employee better. What do they think? How do they approach their work? Who has a narrow view of their role? Who has an expansive one? Who has great analytical skills? Who’s a leader? Who sees relationship building as necessary for success? Who sees it as an impractical and tiresome task? This valuable information can inform feedback and identify burgeoning talent.

Lastly, team dialogues enable the group to practice working as a team in a low-stakes setting. What are the collective expectations? For important meetings, do people perform better in a virtual setting? Or does the milling around before and after meetings enable clarifying side conversations? Understanding these dynamics is crucial when the pressure is dialed up. 

Communication Training for Everyone

Sometimes, employees don’t get along. Supervisory meetings can go poorly. We’ve all had that demanding client who takes up more resources than we’d like. Miscommunication is a time and resource drain. Left unresolved, it can negatively impact staff and workplace culture.

Teams that communicate better stay on track and produce better results. Communication training helps employees build empathy and better connect with their colleagues, supervisor,s and clients. Great communication training teaches staff essential skills and how to apply them to diffuse tension. The trainers must have experience in workplace people management, employee engagement, and conflict resolution.

As Justine’s company grew, its needs evolved. New managers required support, including a comprehensive onboarding process that educated them about the company’s expectations and equipped them with essential skills. Regular team dialogues enabled staff to share ideas, address concerns, and build trust. Communication training helped employees connect more effectively with their clients, colleagues, and leadership.

Growing companies want a workplace that balances ambition, excellence, and values. A methodical approach, coupled with the proper support, can help you get there.

Disclaimer: The content is intended for general informational purposes only and should not be construed as legal advice. If you require legal or professional advice, please contact an attorney.

Genesis Fisher
Genesis Fisher is a lead facilitator and trainer with JAMS Pathways. An experienced certified mediator, Genesis is adept at facilitating positive change. Her training and workshops have helped over 2,000 people in six countries communicate better in the workplace. A sought-after teacher, writer and speaker, she serves on the Advisory Committee for the Center for Creative Conflict Resolution, which provides conflict resolution services for over 70 New York City agencies.