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What I’ve Learned: Leadership Lessons from Bosses Past

Cartoon image showing a good boss and a bad boss with Cavalry logo

Before launching my own companies, I had the good fortune of working across a wide spectrum of company types. All in the same industry (real estate) but each with a different profile. Local, regional, national, global. Privately held and publicly traded. Along the way, I’ve had the opportunity to catalog impactful leadership lessons from some good bosses… and not-so-good bosses. I learned a lot from both, but today I’ll focus on the leadership lessons – implicit and explicit – I learned from my favorites.

  1. The best bosses are open to new ideas. They also live the mantra that no single person in the organization has a monopoly on good ideas. If you work for a boss who is a self-proclaimed expert and genius who isn’t open to new ideas or challenging the status quo, you should find a new boss. The most ingenious humans in history learned from exposure to and examining new ideas. Science and progress are iterative. Our greatest achievements come from exploring the work of others, challenging the work of others, analyzing what exists, and asking how and why. A boss who consistently rejects new ideas and strategies other than their own isn’t someone you want to work for. Eventually, the dreamers, the ambitious creators, and an organization’s next big idea will walk out the door as disheartened and disillusioned employees seek out more fertile fields for innovation. Side note: this is exactly how Taxonics and Cavalry came to be!
  2. A good boss takes the opportunity to explain the “why”. For teams to operate at maximum ability they need to know why they are being asked to do what they do. What is the problem being solved, the market being penetrated, and the strategic plan being implemented? Not every detail must be revealed, but successful teams have bosses who can explain the “why” in a way that resonates with that particular team and motivates them to successfully achieve the end goal.
  3. Nothing says I love you more than money. Yes, quality of life is important, yes work/family balance matters, and yes doing good by doing right matters. But at the end of the day, whether you want to admit it or not, when someone puts an extra dollar in your hand, you have a positive reaction. In some cases, a legitimate dopamine hit. Bosses who provide upside for their employees, rewarding them for the value they create through profit share and other compensation tied to an ownership mentality create an organization that breeds innovation and feeds the innate desire each of us has for feeling valued. High-performing organizations set up compensation programs that reward growth, extra effort, and innovation.
  4. Not every boss is a leader. There is a difference between a boss who leads and a boss who manages. Organizations need both types of bosses. Knowing where and how each of those types of bosses fits in, is the key to building a high-performing organization. A good boss can lead by removing obstacles that impede the team’s ability to succeed. In larger organizations that may mean taking on the corporate bureaucracy that suffocates innovation and efficiency. Other times it could be shielding the team from distractions within the organization. These are the qualities of a good leader and boss to make difficult decisions about how to set the team up for success.
  5. Great bosses make challenging personnel decisions. Far too often, managers, partners, and even CEOs do not have the intestinal fortitude to address personnel decisions head-on in a direct manner. Making the decision to terminate an employee is difficult. It is never easy to confront someone and tell them they no longer have a job within your organization even if the employee in question clearly needs to go. It is remarkable how few bosses are willing to make these decisions even in the face of overwhelming evidence of the negative impact on the team. Far too often, under-performers and employees who erode the motivation of those around them are not dealt with simply because a supervisor can’t stomach confrontation. Good bosses move swiftly and decisively to cut out the malignancy to preserve and improve the rest of the team.     
  6. Good bosses do everything they can to eliminate the potential for petty office politics. The bigger the company, the bigger the politics… regardless of what a company tells you about its culture when interviewing. Politics are inevitable across any sizeable organization and can erode a company’s efficiency and push out high performers.
  7. If you’re with a company that is being acquired, your culture will change. A good boss will tell you that. A new culture can of course be a good or bad thing, depending on where you sit. I have seen it numerous times: A CEO or partner stands in front of the soon-to-be acquired company and its employees promising them that the culture they enjoyed will be maintained if not enhanced once acquired. That is most often not the case because most organizations do a poor job planning for the successful integration of a newly acquired company. And the default to laziness is status-quo. Often the companies being acquired have character and culture traits that could be integrated into the larger company for the benefit of the greater good. But it takes time and planning to identify and absorb that, so often companies simply ignore it for the sake of expediency.
  8. People are the lifeblood and most important asset of any organization. Without good people doing hard things, a company can’t exist, or at a minimum, won’t be very successful in the long run. Bosses need employees. In some cases, more than the organization needs the boss. That’s a good thing and a good boss recognizes that. Good bosses have earned the respect of their team by fostering a relationship built on trust and respect. Ships need captains as much as captains need sailors.

Each of these leadership lessons add up to the biggest one: Becoming a good boss requires effort and a willingness to learn. So above all, I’m thankful to each of my former bosses – good, great and bad alike – for these critical leadership lessons.

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