Training in an Entrepreneur’s World: A Different Perspective

Excerpt from “The Lonely Entrepreneur: The Difference Between Success and Failure Is Your Perspective” by Michael Dermer.

In the constant chaos of an entrepreneurial venture, founders and leaders are always thinking how they can drive their employees to perform at a higher level. But an entrepreneurial environment is unique. Employees generally are working very hard, sleep deprived, and feeling pressure on a daily basis. How does a leader set the tone for employees who are most likely already stretched to the limit? Well, believe it or not, it starts with the leader. The ability to train employees in an entrepreneurial venture starts with the tone set by the leader.

With so much going on all the time, it is hard to determine what decisions are important and what decisions are just the flavor of the day. There are certain foundational elements of your business that must be established to create order, alignment, and discipline. Part of this is setting the behavior guardrails within which you and your team must operate. These “deadly sins”—especially when they come from the leader—send a message that can have a lasting effect. Unless you eliminate them completely, these behaviors can set poor standards, establish values contrary to the interests of the company, and create a toxic culture that can be hard to clean up. Avoid these Deadly Sins at all costs.

1. Speaking Negatively About Customers. When you or people in your organization say things such as, “Our customers are clueless” or “We can sell that to them,” it sends a clear message not only of disrespect, but ignorance about the role customers play in your company’s success. If negative talk becomes habitual, you are more likely to think of your customers not as allies but scapegoats. After all, it’s easier (and faster) to blame the customer for everything that is going wrong than to take a good, hard look at yourself, your product, your service, and your people. Speaking of customers in a negative light also sends a message to your employees that it is acceptable to blame customers, instead of addressing the issue and troubleshooting a creative solution to problem. Crafting new solutions not only strengthens your team’s ability to take responsibility and problem solve, but encourages stronger customer relationships—and your own success.

2. Speaking Negatively About Employees. If you or others in your organization speak negatively about employees, it sends the message that the company does not value people and is only in the business of advancing people when it serves the company’s needs. There are times when the skill level of your employees is deficient or part of your team is underperforming. During these interactions, make sure that you speak to and about employees with respect. These individual encounters quickly become a part of your culture and an expression of your brand that reflects on you as a leader and on the reputation of your company. How you speak has a significant effect on employee morale, the efficacy of your leadership, and, ultimately, the reputation of you and your company.

For example, when an employee leaves the company, our first reaction is often a negative feeling toward the employee and an assumption that he or she didn’t value the organization. We might react with statements such as, “They were not that good anyway” or “It was time for them to go” or “We will be better off.” Speaking ill of individuals who leave the organization (e.g., “It’s good that ‘Steve’ is leaving. He was not that good anyway”) sends the message that employees are not valued and that the organization lacks respect for those supporting it. This not only has a negative effect on existing employees, it also can blind companies to the root causes of that individual’s departure.

Regardless of how your employees leave, take the high road. Wish them well and strive for the reputation that your organization is one employees want to work for, and how you treat individuals when they leave is an important representation of that.

3. Dismissing How Your Team Feels. Everyone understands that entrepreneurial ventures don’t succeed, or exist, without hard work and dedication. But that doesn’t mean you can ignore the needs and feelings of those struggling alongside you. If you dismiss your employees’ state of mind when you communicate or make decisions, you undermine your company’s strength, resilience, and dedication to the business and its customers. You must respect the dedication it takes to do everything from the simplest daily task to the most complex business transaction. If you are thinking: “I don’t have time to worry about how people feel,” your employees are thinking, “Does our leader really understand the sacrifice we are making?” That question usually is followed by: “I wonder if the sacrifice is worth it?” The effort and perspective of every person matters. The organization cannot serve customers and its mission and make forward progress if its individual gears aren’t well oiled and given proper attention.

4. Making Exceptions for the CEO. One of the most damaging behaviors of a young company is demonstrating preferential treatment for its leader. When your team believes your needs come first, or at their expense, or that the rank and file’s needs are less important than the needs of the leader, it creates an undercurrent of resentment at all levels of employment. Similarly, when the rules apply to everyone but you, it sends the message that the CEO is above the law, and undermines the faith that you have the team’s best interests at heart. On the other hand, when the CEO is the first person on the team to hold him or herself accountable, or to be accountable to others, it sends a message that everyone is in this together.

These Deadly Sins aren’t just for you. They should be an operating agreement for your entire team. This means you also must have zero tolerance for anyone in the organization who exhibits these behaviors—including yourself. If these perspectives and behaviors develop, even for a short time, they become habits that will significantly undermine the strength of your team and the progress of your business for years to come.

Training in a corporate environment is one thing. Training in a startup or entrepreneurial venture is quite another. Even though there is a constant whirlwind of activity, if the leader doesn’t set the tone for behavior, the ability to guide employees to greater heights will stunt the progress of the business. When we learn to train ourselves first as the leader, we set the tone for learning and growing among the entire team.

Excerpt from “The Lonely Entrepreneur: The Difference Between Success and Failure Is Your Perspective” by Michael Dermer. For more information, visit:

Michael Dermer founded IncentOne, the first company to provide financial rewards for healthy behavior. After a decade, he  watched it almost collapse in 2008 during the financial crisis. Dermer not only overcame the struggle to sell his company in 2013 and become an industry pioneer, he also discovered The Lonely Entrepreneur methodology and is now a professional speaker, consultant, and coach for start-up businesses and entrepreneurs.

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