5 Leadership Lessons I Learned From Previous Bosses

It is one of my biggest pet peeves when people believe they have learned nothing from “bad” leaders. We’ve all had the horrible boss that broke our souls and traumatized us emotionally. Not all leaders are made equal. However, we do learn from them all. Whether your experience with the leaders in your life was positive or negative, they did, in fact, shape you in some way.

I’ve been in the entrepreneurial space for over a decade, and I’m still beholden to the valuable lessons I have learned from the leaders that shaped me into the businesswoman I am today. Not all of these experiences were positive fairy tales, and I had many days when I came home crying and dreading the fact that I needed to go back to “that place” tomorrow. However, I’ve learned from this. Some of these lessons were extremely hard, but this did not make them any less effective.

Here are the 5 most significant lessons I’ve learned from previous bosses and other leaders, good and bad, whom I’ve worked for and with in my career. I still return to these basics when I am stuck.



1. Respect Is Earned

“Treating people with a basic level of respect goes a long way toward them respecting you and ultimately motivating them to believe in your mission.”

In my experience building high-performing teams, I’ve worked with many types of leaders. Many of these had a distinct belief that they reign supreme to the team, that their time is more valuable, and that they deserve respect for respect’s sake. This is the single most destructive thing you can do to your team. Although there should be healthy boundaries and evident concern for your position of power, this respect ultimately needs to be earned. You can never expect someone to give you most of their life, best efforts, skills, and time if you are constantly making it clear that you are somehow their better, or they should be grateful for the time you deem to gift them.

Treating people with a basic level of respect goes a long way toward them respecting you and ultimately motivating them to believe in your mission. When you occupy the space of a leader, you are in the position of power, and yes, with that power comes responsibility. This is, by the way, without fail, the thing that always rattles most leaders and puts them on a solid track to hating my guts. Unfortunately, everyone wants to be the boss – until they are. It’s not easy, and the balance you have to strike between good people skills and the best interests of the company or project is a fickle one.

It’s also worth remembering that we are not all destined to be on the same path for the rest of our lives. Who you treat with respect now, guide, motivate and lead may be your new client one day, your partner, or a fabulous connection for new business. People always remember who treated them well and where they learned and gained the most. Make sure you are on the side where they are happy to recommend you or refer you one day.

Should employees stay, you ultimately want them to be there because they are motivated to be there. If they aren’t, their work output will be dismal, impacting your team’s productivity. Employees who feel respect do more, risk more, and give more.


2. Make The Tough Decisions

Of course, respect is a two-way street. Even if you are the best leader in the world, you will not always work with people who have the same business ethic as you or are motivated by your purpose or mission. Not every employee will respect you, and they may even continuously push all your wrong buttons. Your duty as a leader is to deal with this efficiently and decisively before it negatively affects the rest of the team.

Although it is your responsibility as a leader to make sure you allow each employee to learn through their mistakes, coach and guide them, and teach them new skills, there is also truth to the idiom that you can only lead the horse to the water, but cannot make it drink. It’s always so interesting to me how quickly leaders can get hung up on the horrible mistakes the “good employee” made while ghosting over another inexcusable incident created by the team member that always seems to be causing discord. This is primarily because they don’t want to “get into again” with this team member. But avoiding the constant conflict created by this team member often leads to the breakdown of the rest of your team. The motivated members give their all without asking anything in return, believe in your mission with a single-minded focus, and bring you the best work output.

These troubled children rarely face decisive action or discipline for various reasons: it’s tough times, you can’t just let someone go, you don’t want to be responsible for taking someone’s livelihood away from them, or you feel it’s necessary to just give them one more chance. Let me just be clear, this is nonsense! You are the one that makes the tough decisions. Your team looks to you to lead them with a clear vision, support them, and look out for their best interests. They spend most of their waking life in your office, working towards your goals and dreams.

Think of all the others who would do anything to work for you, to have a job that needs income motivated by your mission. There is always someone who needs a break, who is waiting in the wings for their turn to shine. So make the tough decisions when you need to and be a leader your team can count on.


3. Boundaries

“It is complicated to set and implement boundaries later when there are no clear boundaries at the beginning.”

Setting clear boundaries does not mean you are a dictator, depending on how you go about this, of course. Setting boundaries gives your team explicit instruction on what you expect from them, what is acceptable and what is not, and what their future at the company looks like. When leaders are too lenient, people will take advantage of that, as any of us will do in similar situations. Unfortunately, that is just human nature.

It is complicated to set and implement boundaries later when there are no clear boundaries at the beginning. I see this in companies where leaders want to create a casual working environment, flat management structures, and a social working vibe. To be clear, I am not suggesting that all sense of enjoyment should be drained from the working space. However, it’s difficult to establish a productive workplace if you don’t set the direction or are unclear about what you expect from your employees. Employees become frustrated with other team members they feel do not have the same work ethic or motivation they do, introducing new rules and policies becomes contentious and keeping the team happy becomes impossible.

We all do better in a secure environment where we understand what is expected of us and always know the consequences if we or others do not meet these expectations.


4. Teach

To put it as bluntly as possible, leadership is not for you if you’re not into teaching and sharing knowledge. I am sure I’ve rattled many cages with this sentence but that doesn’t change its truth. We do best when challenged, learning new things, evolving, and growing. When we stagnate, we become demotivated, depressed, and despondent. Chances are, if you are in this position of power, you hold an immense amount of knowledge you can share. Taking the time to invest in sharing your expertise with your employees has a huge payoff.

Ultimately we are all chasing time and the more things you take off your plate and can entrust to others without the need to micro-manage, the more time you have to pursue your own growth and the vision for the company. Just a hint: If you think it’s impossible not to micro-manage because too many mistakes occur, then I have two harsh truths to share here.

  • You are not managing your team effectively, with the right style and right approach, considering the different strengths people bring to a team OR
  • You have the wrong people doing the wrong work.

Moving on . Barking out orders and expecting employees to blindly follow them is not teaching. This can be highly discouraging, especially for superstar team members who want to be there and want to learn. People respond better when you explain why you are asking for something to be done in a certain way than if you just throw out a blind order with no rhyme or reason. Although the reason may be apparent to you, your team may need to understand why this is done in a specific way so they may be better able to act more effectively the next time this is required or even suggest better ways to do this in the future. This also goes back to having a healthy dose of respect for your employees.


5. Disagreements Can Be Good

“Having healthy debates about new ideas and encouraging your team to motivate why they disagree with your take is a fertile breeding ground for creative solutions to complex problems.”

There is a respectful way to argue and disagree, and explosive exchanges are not encouraged. However, leading a team that is expected to always blindly agree does not serve anyone. There is always room for leaders to grow, learn, see things differently, and seek a new perspective. This makes a good team great and gives a company the edge they need to compete with others in the market. Groups in constant fear of disagreeing with the leader, voicing opinions, or suggesting new things are stagnant, and ideas will wither and die.

Having healthy debates about new ideas and encouraging your team to motivate why they disagree with your take is a fertile breeding ground for creative solutions to complex problems. However, this will never naturally happen if team members are scared of the leader, and the company has a culture of listening for listening’s sake only, not for implementation. This will inevitably discourage team members from sharing as they feel their ideas are constantly heard and passed over. Leaders should open themselves up to debate every now and again. You may be surprised by the results that follow.


The Take-Away

Some of these lessons I learned from great visionaries, in my opinion, who had a helping hand in shaping me into the business professional I am today. Leaders who had patience with me while I was still shaping the basis of who I wanted to be as a professional and what I ultimately wanted that identity to look like. Other lessons on this list were learned on “the battlefield” of unhappy workplaces, verbally and emotionally abusive bosses, and clients. Although some of these lessons were learned through good experiences and others through bad experiences, they all impacted me, helped me, taught me, and guided me to understand what I wanted to stand for and what I did not want to stand for as a leader.


What do you stand for?

Remember to comment below.

Love and light


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