What I read

Three crucial skills that leaders must develop to become executives

theskip.substack.com / 25 July 2021

Becoming a great executive requires a set of skills beyond what’s needed to be a leader. Executive skills are subtle and can be elusive to managers, demanding a great deal of focus, courage, and dedication. These skills include taking (almost irrational) career risk, learning to scale by trusting your team, and developing advanced soft skills. New skills are hard for leaders to develop simply because they’ve already found success, which makes them less motivated to make substantive skill shifts. But those who see change as a path to growth will ascend to top roles within an organization.

Ideally, your career will go through three acts. Act I is the “setup.” It’s where you transition from being an individual contributor to a leader. Act II is your transition from a leader to an executive. And Act III is where you start your second career, hopefully unconstrained by previous financial and personal needs.

most leaders, like clockwork, complete Act I roughly 10 to 15 years after they enter the workforce. Not everyone ends up as a leader, but those who rise to that level follow a pretty consistent timeline. Some start fast, lucky enough to land in a rapidly growing environment and be supported by a good manager and team, and are able to quickly move from learning a skill to mastering it

unlike in the first dozen years, career paths become highly inconsistent. Some people continue to rise, but most will stall or even decline. This is highly unintuitive, but in reviewing the careers of a myriad of leaders, I see he’s absolutely right

When you reach Act II, you’re comfortable and have a successful career. But to grow, you need new experiences, which likely means you need to change jobs. Change now takes courage and significant risk—you have more to lose than you had in Act I. So most prefer to avoid making big changes, resulting in fewer new challenges and much slower growth than they experienced in Act I.

Now fast-forward 10 to 15 years, after you’ve purchased your first or second home and you’ve established roots in that particular city. What will it take to move again? No doubt, we could always move again to a bigger, better home. But it’s more of a luxury than a necessity. So many people simply don’t do it, instead being content with staying the course, avoiding the pain and cost of moving, and focusing their energies elsewhere.


Getting things done in a workplace is some combination of what you know (“IQ,” or hard skills) and how to use your knowledge (“EQ,” or soft skills). Act I is where you build out functional expertise. For a software developer, it’s how to effectively write quality code, tackle more complex technical problems, work in a team, and eventually manage a group of individuals. For a product manager, it’s how to run a meeting, set goals and direction, drive accountability, and deliver useful products to end users. 

to grow you must take risks and constantly put yourself in new, challenging, and increasingly ambiguous settings. Your current expertise will help navigate these new roads, but you’ll need to build new talents and adjust your existing skills to truly excel. Most leaders don’t have an intense desire to reinvent themselves—they’d prefer to continue pushing on the skills that made them a leader to begin with. But new challenges require new approaches that fit the new environment, not just replicating the past

The majority of my leadership coaching is to help people manage these anxieties and frustrations. These include:

  • “I get nearly zero feedback so I feel like I don’t belong.”
  • “The company simply doesn’t acknowledge my importance. It’s taking far too much time to get promoted, increase my compensation or my scope.”
  • “I’m frustrated by how slow it takes to make things happen.” Or, “The bureaucracy around here is crippling.”
  • “I just don’t understand my tenured co-workers. They just feel so stuck in their ways, unable to consider new ideas.” Or I hear, “These new people just have no sense of how things are done around here. They are impatient and shoot before they aim.”

With this added responsibility, at first you might just end up working harder and increasing your level of engagement. Up to this point, your success has mainly come from making good decisions and mastering the details. So naturally, as the problem space gets bigger, you increase focus and absorb more context. Sadly, there are only so many hours in a day and your capacity is finite. So on your path to becoming an executive, mastering each detail will hold you back. You’ll need to develop a new, crucial skill: building teams and trusting the people in them.

So to scale yourself, you will need to recruit leaders who can work and thrive under you, likely from outside the company. And you’ll need to learn to trust them, even when you don’t have full context. Leaders who are scaling learn:

  • how to prioritize and be efficient with their time
  • invest in finding and managing great people
  • dive in at the right altitude
  • how to make the right decisions by asking just the right questions

After reading the challenges that come with Act II, please don’t feel discouraged from pursuing an executive career path. If you are in Act I, do your best to recognize and pull forward the skills noted above. And if you are in Act II, realize that career growth will rapidly decelerate by default. To keep pace and continue to grow, you will need to aggressively seek new talents and skills.