Do Hustlers Make Good Bosses? I A Look at Corporate/Organization Leaders

Let’s get one thing straight from the start. I hate the word hustler, as it has come to mean a person who is constantly looking for ways to make a dollar. Don’t get me wrong, there is nothing wrong with people who are trying to advance, make a living and create opportunities for themselves.  It’s just that I don’t subscribe to the whole, working oneself day and night nonstop to “Make Things Happen”.  In a future blog, I will discuss why I believe this method of working 24 hours non stop without proper rest, investment in personal relationships and other life experiences is counterproductive and can hinder the desire to become successful.

In the meantime, for the sake of this article, we’ll explore 3 different types of business leaders or shall we say hustler/leaders. 

A blockbuster sleazy, cunning movie hustler with dark shades, dressed in a long trench coat with a liner filled with assorted jewelry, offering you a special price may be what you imagine when you hear the word hustler.

Surely, you don’t fit that description, right?  You are refined, well educated, and poised. Okay, but consider what it takes to start and operate a corporation. It requires certain attributes of a basic hustler however, it’s the type of hustler I want us to explore, so please grab your favorite beverage and continue to read. 

I grew up in a Mountain state and I’ve lived on the east coast with extensive experience with both Non-profit organizations as well as corporate America and now I am an entrepreneur with businesses reaching into the global market. In this process, I have identified 3 different types of hustler/leaders that can destroy the very thing they want to build.

Peddler – This is the hustler/leader who travels from town to town or country to country introducing and selling their products. They aren’t known for staying in one place for very long and are great at making quick connections and have a keen sense for who are either at the top of the chain or who are the gatekeepers to make their impromptu pitches. They also work well under pressure; however, these types of hustlers typically don’t have nor do they desire to have long term business relationships as their primary focus is the quick sale and are “For the moment” thinkers. In a corporate setting, this type of leader is usually on the floor of a company, moving quickly from department to department trying to peddle their ideas to department heads and managers with little investment in the well-being of their employees or consumers they target. It’s all about high volume sales with quick returns and despite a global e-commerce  era, some leaders still aren’t utilizing technology within their companies to the fullest. For these reasons, this will ultimately lead to a company with no longevity because this leadership style haven’t established professional relationships to continue to develop lasting partnerships.  Today’s employees and consumers want corporate leadership who are socially conscious and not just profit driven. Lastly,  a peddler can only operate on a high-octane level for so long before they experience burn out.

Swindler – This person spends much of their time devising plans to see how to best maneuver psychologically. They keep everything tightly compartmentalized and work towards investing in creating a toxic work environment. You can count on this type of hustler/leader to be dishonest and non-transparent when it comes to sharing necessary information with their employees, board members, partners and stockholders.  

You can never get a straight answer from them. Any dialogue you may have with them is filled with riddles, puzzles, and deflective statements. The company/organization with this type of leadership is generally an organization full of confusion as one department doesn’t know what’s happening with the other.  Memo after memo is sent out by company heads trying to get clarity yet, clarity is rarely achieved. Everyone is frustrated because there are no clear directives yet, excellence is demanded from them and worst of all, leaders are pitted against one another as the main leader purposefully blames others for their deceptive tactics. Why in the world would a person who is trying to build a “successful” business work so hard at sabotaging it?  Check out our future blog entitled, “The Boss Within the Boss” to learn the answer to that question.  

In the meantime, know that this type of leadership usually leads to high and harmful workforce turnovers impacting the sustainability of the company because of the major cost associated with frequent hiring.

Pester – This type of hustler/leader does not understand, nor can they comprehend the idea of providing their work talent enough time to properly execute tasks, projects and campaigns. They struggle with allowing the process to take its course and aren’t considerate of how rushing everything affects their team.  No sooner than they tell their team about a future project, they bombard them with 10 other things with no room to fully develop,  mature or accomplish the other previously assigned tasks. 

This leadership style will call, text, email or pop into the office for project updates while dropping yet another assignment on the team.  Their staff is mostly exhausted and unhinged because they are overworked and feel like failures when plans fall through the cracks. Employees see the problem and

have made attempts to share with the hustler/leader that they are happy to do their jobs and make the vision come to fruition; they just need more time to get things done but the leadership takes this as a sign of no confidence in their leadership as well as the team’s unwillingness to make necessary sacrifices for the success of the company and therefore, the pester becomes defensive. 

 As a leader of your company/organization diligence is admirable, however, if you recognize any of the hustler/leader traits in your leadership style, we can help you understand how it adversely impacts  your vision and objectives and we’ll show you how to succeed as a leader that your workforce will be excited to work for.

Letra Davis

Letra Davis is a conative vision building entrepreneur and has been a champion of engaging leaders and everyday people in multiple sectors to live uniquely, authentically and passionately for many years.  She’s a playwright, songwriter/arranger, vocal trainer, musician and artist. She’s also an inspirational content creator with LeLe’s Chronicles. She’s a forensics original orator and conference speaker.
When she’s not helping companies improve their work talent and increase revenue, she a foodie, movie buff and a true Trekkie and enjoys traveling and nature hikes. 
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