The Best Bosses I've Ever Had

If you’re the leader of a high-growth company, it’s important that you decide what kind of leader you really want to be. Your personal leadership style has a large impact on your company’s culture and success. So, it’s critical that you first understand how you operate best so you can build a team that complements your style.

One of the best ways to learn about leadership is by discussing and analyzing past experiences you’ve had. I’ve worked with a wide range of different leaders over the years, each of which has impacted my personal leadership style.

Below I’ll share some stories and lessons that I’ve learned from my bosses throughout my time in business. Hopefully, you can use these anecdotes to help you develop your own leadership skills and improve how you run your organization.

Create The Best Onboarding Experience Of All Time

One of my first-ever bosses happened to be a veritable guru of onboarding. As soon as I arrived, she took my job description and broke it down into discrete parts. Then, she took these parts and described each one in terms of what it meant for me on a weekly basis, so I was only really learning one new task a week. Thanks to her guidance and stellar onboarding, after eight weeks, I was effectively able to do her job, which allowed her to focus on much more important things, like supporting the company CFO.

This was a great boss, and I came back for three separate internships with the company. I didn’t realize it at the time, but she was a world-class on-boarder, and my job was much more interesting because I understand what I was doing, why I was doing it and how what I did impacted the company.

What I learned most from this excellent boss was the power of getting someone up to speed quickly so they can get started with meaningful and productive work right away.

However, I also realized as much as onboarding is about getting new hires to start contributing to your organization, as a boss, you also have to be sure that you’re not overloading them with too much information. For people to truly succeed at your organization, you have to make it easy for new team members to be successful.

Focus On The Outcomes

For many of us, myself included, the process is just as important as the outcome. We can get too caught up on how something is done, rather than what happens as a result of that process.

Early on in my career, I was so focused on the idea that things had to be done a certain way. Thankfully, I was lucky enough to have a boss that really didn’t care how I did things, so long as everything worked out.

For me, this was a game-changer. My boss had a very rudimentary excel spreadsheet that he used for complex financial reporting. When he handed it over to me, instead of forcing me to do things his way, he allowed me to do whatever I wanted to get the job done.

Eventually, I created a totally new modeling spreadsheet that was significantly more effective. I ended up more or less throwing out everything he had made, but he was okay with the whole situation simply because it all worked.

Since he was so focused on outcomes, not on the process, my boss gave me the space to learn, grow, and work things out my own way. This experience was incredibly motivating and has truly helped shift my tactics as a leader and manager.

Know what Success Looks Like

As an employee, one of the most important things is to know what your role is and what you’re working towards. If a team member doesn’t know what your vision of a successful project outcome looks like, it’s possible that they’ll end up creating something that they think is awesome but doesn’t quite live up to your expectations.

Indeed, one of the best bosses I ever had the pleasure of working with was someone that gave me clear, vivid pictures of exactly what he expected from our work. He gave me the answers to the problem but left it up to me to figure out how I was going to put all the various components together to get a stellar outcome.

In this job, I always knew what success in a project looked like. However, I wasn’t simply left to my own devices without any guidance on how to move forward. My boss was always open to questions, comments, or concerns. Plus, he was always there to help guide me toward a solution when I didn’t know which way to go.

The key in this situation, though, is that I knew what the solution looked like from day one, even though it would take some time before I actually arrived at the end of the project. After moving on from this role and further into my career, I’ve worked hard to implement this strategy into my professional life.

With my team members, I strive to be crystal clear about what success in a project looks like. However, I also always take the time to ensure that my staff know they can come to me with questions.

In many ways, my team actually needs to manage me – not the other way around. I always tell them that they should reach out and talk to me about how they’re planning to arrive at our agreed-upon solution so we can work through any issues that arise together.

Hold People Accountable

Holding people accountable isn’t as easy as it might seem. The best bosses I’ve ever had have always made sure that I’m responsible and accountable for my work (and my mistakes).

These managers routinely checked my work and questioned why I did something the way I did. Even though they were always supportive and they genuinely wanted me to succeed, they would let me know when I was wrong.

Sure, it’s tough to hear that you didn’t do something as well as you would’ve hoped. Nevertheless, this process showed me the importance of always doing your best work in any situation. It also demonstrated how valuable this constructive feedback is when it’s given in a growth-oriented manner.

Ultimately, the best bosses make sure that you do your work correctly and they check that it’s done thoroughly. Over time, they also know when to back off a bit as their staff more consistently produces fantastic work.

Treat People Well

Even when we’re at work, we’re all still human beings that just want to be treated well and accepted by others. I once had a boss that went out of his way to be kind to all of his staff at all times.

In reality, it’s so much easier to be critical of someone, something, or some situation than it is to see what went well. All too often, we opt for negativity instead of empathy, particularly in a stressful work environment.

This particular boss, though, showed me that being empathetic to others, especially your staff, can make a huge difference in the company culture and people’s experience with the organization. Simply by caring for others and treating them well, this boss demonstrated to us that we truly mattered to him.

Being genuinely kind and caring is a fantastic trait and something I think we can all benefit from as leaders.

Trust Your Staff

Fresh out of university, I landed a job at a small start-up. But, within a few months, I was leading the development of important new products and was the manager of a team of older staff members.

Why? Well, it’s simple: My boss trusted me. Although I had no professional experience in this industry, I was passionate about my work and really gave it my all. I knew the product very well and I wanted it to succeed. I worked like a dog for this manager, as I wanted to repay his trust with incredibly high performance.

As time went by, I was given more autonomy and my boss focused on more important matters. We ended up selling the company for almost $400 million, showing that sometimes, trusting your staff pays off at the end.

Don’t Micromanage

We’ve all had bosses that like to micromanage every aspect of our day to day lives. Not only is this inefficient, but it can also hinder your employee’s performance and damage their confidence.

One of the best bosses I’ve ever had allowed me to just get on with my job. They didn’t want to micromanage me on every task and it didn’t matter if I did things their way, so long as I got the job done well. They focused on confirming major deadlines and deliverables with me, but left it up to me to get clarity on smaller issues. In a sense, I was managing them to get help when I needed it.

This type of management style allowed me to do my best work and get stuff done, instead of worrying if each thing that I did was exactly how my boss wanted it.

As managers, it can be hard to let go a bit and give people this freedom. However, with high-performing staff, you’ll usually be pleasantly surprised with the results by the end.

Let People Make Mistakes

There are two types of people: those that make mistakes just once and then learn from them, and those that make the same mistakes over and over again. Personally, I’m the former because I hate making mistakes. I work hard never to make the same mistake twice.

Making a mistake is a great learning opportunity. Sure, no one wants to make a mistake, but if you can turn that shortcoming into a tool for success down the line, then you’ve set yourself up for success.

Unfortunately, I’ve worked with a lot of people that would rather do nothing at all than risk making a mistake. This is often because they’re afraid of what will happen if something doesn’t go completely according to plan. Sometimes, it’s because there is an organizational culture that doesn’t value mistakes as learning opportunities.

All of the best bosses that I’ve worked with during my career were comfortable with uncertainty. They understood that mistakes happen. They also recognized when you’re looking to innovate and grow, mistakes are invariably a part of life.

For them, having staff that made mistakes wasn’t ideal, but they would work to manage any situations where a mistake had a major impact so that we could learn from them instead of fearing the consequences.

They would routinely let me make mild mistakes and then follow-up with me to talk about how I could improve from the situation. In reality, if a manager always stops someone from making a mistake before it happens, that team member will never learn the consequences of that mistake and will struggle to prevent it from happening the next time.

As managers and leaders, we need to be ready to facilitate growth and learning among our staff. Making mistakes and understanding what happened is one of the best ways to improve over the long term, so it’s up to managers to create an environment where mistakes are okay, so long as we learn from them.

Be The Boss That You Would Want To Work For

All of the bosses that I’ve discussed here have helped me become the manager that I am today. We learn and grow from our past experiences and it’s clear to me that there is so much that we can learn from the people that we used to work for earlier in our careers.

Ultimately, we should all strive to be the boss that we would personally want to work for. If we wouldn’t want to work for us, then why should anyone else?