The Leadership Trail - Hiking our Way to Become Better Leaders

One topic that has always fascinated me is learning and development (L&D). It’s been a core part of my journey so far both in terms of providing learning and development programs, as well as consuming it.

Experience will most often supersede theory. But we need to start somewhere. Knowing the core concepts and having awareness of what we know and what we don’t know is key to accelerating our careers and our personal and professional growth.

At school and university, though, programs often feel linear. A sequence of concepts is put together in several classes to make up a program for a number of years. There are always many side quests, for those with enough time and dedication. But the structure is generally there.

When we start our careers, things change quickly. There’s no longer someone dictating our learning path.

We’re now owning this responsibility.

On the topic of leadership, even though there are many courses, books, certifications, and so forth, it’s not always clear where to start. It often feels like a huge leap between being inexperienced or an IC and becoming a seasoned leader.

As I transitioned into management and began my journey into leadership, learning skills became fuzzier. For me, non-technical skills are harder to grasp, learn and apply.

It’s difficult to know what good looks like when the feedback loop is longer and it involves other people. It’s non-deterministic, and it’s easier to get lost and make costly mistakes.

In exploring learning and development opportunities in the past, I came across a leader who said something that stuck with me. I can’t remember the exact words, but the spirit of the message was:

Learning is like climbing a mountain. It’s never a straight path up. Sometimes you need to go sideways. Sometimes you need to get down in order to go up. But eventually, you will find the trail to the top.

This is such a powerful way to embrace everything in life. I like to apply this to learning and development as well.

Don’t try to know everything in advance. Focus on your most immediate challenges. What are the tools you’re missing to deal with those challenges?

Broadly speaking, the categories of problems as leaders are mostly defined. Within those categories, look for useful resources to apply immediately. Build your mental models around those concepts.

As you continue doing this, you will build more experience and tools to tackle future challenges.

Over time, you will build confidence, make new connections, and explore new ways to tackle problems.

Learning is a journey, and when paired with experience, it will be one of the most fulfilling puzzles you’ll solve as a leader.

Which skills to learn first and in what order is personal. There is no clear path from A to B. There is no one right answer.

Below is an ever changing list of resources that have helped me and some close friends on our journey to becoming better leaders. It’s not comprehensive, and I’m sure I’m missing important references and resources.

But take it as it is – a journey to become a better leader. Use these recommendations as a menu: pick and choose what makes the most sense for your journey into leadership, and don’t be afraid to get back to basics when needed.

Please leave a comment down below for more recommendations or your thoughts on it!

Learning and Development – Leadership Skills

The learning and development resources listed below are grouped by theme for convenience. The themes may overlap, but hopefully they help make sense of how these resources can be helpful.