The Top 5 Leadership Lessons I’ve Learned Over a 20-Year Career

Leadership is not without its pitfalls. I’ve now been working for 20 years across a number of industries– in tech, politics, non-profit and state government. In that time, I’ve had the opportunity to work with a wide range of leaders. 

However, one of the worst aspects of leadership is receiving bad advice and then acting on it. Over the course of my career, I’ve received my share of leadership advice— some great and some awful. It takes a certain level of discernment to understand what’s worth listening to and what’s unhelpful.

Here are five nuggets of wisdom that I’ve received that I consider invaluable in growing in as a leader.

It goes without saying but people tend to remember your latest accomplishment, not that big win from two years ago. Whether that’s fair or not, that advice seems to have held true over my last 20 years of work. Can you even remember who won the World Series two years ago, let alone last year? It’s called the recency bias and what it comes down to is that as a leader you need to consistently perform or otherwise you may be shown the door. There is not much tolerance for a ‘one-hit wonder’.

The operative word is consistency. At the end of the day, steady performance reinforces the accuracy of the advice because you dependably produce high quality work.

The global pandemic has required many of us to dig deep and acomplish some MVP-level work as we dealt with the many unknowns; trying to make sure the business survived, that you could pay your staff, deliver services to your customers, and more. As a nation and as a society, we have been in the fight of our lives lately but it’s difficult to maintain the intensity for too long.

As leaders, you have to figure out how to scale processes — not yourself. Rising to the moment should be the outlier, not the ordinary. Leadership calls for a macro look at the environment. You have to build capacity and competency on your team so that it decreases the reliance of heroics of just one person. On top of the process, there needs to be grooming of your team to take on added responsibilities and development to equip your team with skills that allow them to perform at the highest levels.

Your reputation is your calling card and what you’re known for. You can be principled or unethical, whatever the case reputation matters.

It’s important to understand that with the mantle of leadership, there is an expectation that you are in control. Just think of the leaders with notoriously bad reputations, like Elizabeth Holmes of Theranos or Billy McFarland of Fyre Festival. Holmes and McFarland are now reputationally enshrined as case studies of what terrible leadership looks like.

A great reputation acts as a magnet as it allows you to attract talent, inspire your team, gain investors, and capture market share. A terrible reputation does the opposite — it repels talent, investment and interest.

This is about mindset, staying positive in adverse situations is a must in leadership. People look to leaders for direction and inspiration. A poor attitude can be a contagious team killer. Team morale can worsen and erode team cohesion. However, when the leader is able to convey positivity, it creates a positive atmosphere.

Basically, this means to continue to stick with your principles. As a leader, you should be principled and keep to your convictions. There will be ups and downs , but if you can anchor to your core beliefs of doing what’s right and be unwavering in the face of adversity, you can withstand the challenges you face.