Leadership = Skills x Work

Read time: ~5min

A few weeks ago I stumbled upon this tweet from Dave Kline. 

This is incredibly powerful advice for any leader.

However what’s simple in concept, is difficult in practice, as each of these requires a set of skills.

And like every skill, there are two inputs: talent and work.

Whatever the skill may be, you want to fall somewhere on the upper half of this matrix.

• Diligent Workers and High Achievers are A players who make everyone around them better, and attract other A players.

• High Potential individuals are often B players who fall short of their own expectations and attract other B or often C players to boost their own image.

• Underachievers are C players who hold everyone back.

Without hard work, at best you’re a B player.

Hard vs. Soft Skills

When it comes to leadership, there are two types of skills: hard skills and soft skills. 

Hard skills are more technical, easily teachable, often quantifiable:

• Time management

• Project management

• Operations/operational management

• Data literacy/analysis

• Financial analysis/planning

• Public speaking

• etc.

Soft skills are more emotional, harder to learn, and not easily quantified:

• Empathy

• Trust

• Communication

• Candor

• Relationship building

• Storytelling

• Resiliency

• etc.

My goal with today’s newsletter is to:

1. Help leaders identify and develop the key skills necessary to make a transformational impact on their teams and business.

2. Help individual contributors seek out leaders with the hard and soft skills that will enable them to do their best work.

I re-watched Good Will Hunting and it taught me about B2B Sales Leadership. 

Good Will Hunting is one of my favorite movies of all time. It’s the story of a young, troubled genius with a hidden talent for mathematics who, with the help of a therapist, confronts his trauma-filled past and personal struggles, and finds his true path in life.

If you haven’t seen it (you’re missing out), here are the cliff’s notes:

Meet the squad

Will Hunting 

A twenty-year-old mathematical prodigy from South Boston, raised in foster care, who frequently finds himself incarcerated or drifting through court-mandated jobs. Hobbies include drinking with his pals, starting fights, and solving complex mathematical theorems.

Professor Gerald Lambeau 

Mathematics Professor, former Fields Medal Winner (think Nobel prize but for numbers), and Harvard graduate. Professor Lambeau catches Will solving a highly complex theorem in his MIT hallway—something only a handful of people in the world can do.

He convinces the court to release Will under his employment and supervision, under the condition that Will also receives therapy. 

Dr. Sean Maguire

Played by Robin Williams (RIP to a legend), Sean is a Psychologist and Lambeau’s former Harvard roommate. Like Will, he is from South Boston, with a similar childhood and trauma filled experiences.

After unsuccessfully working with half a dozen therapists, Sean is the last hope for effectively counseling Will.

Background

Professor Lambeau and Sean have vastly different approaches to working with Will.

Professor Lambeau: Analytical and transactional

Lambeau sees Will primarily through the lens of his academic abilities and is driven by the idea that Will's talents could be harnessed for great achievements.

His approach is to push Will, detaching himself from any human aspect of the process, treating Will as a commodity in the hopes that these pending academic achievements will reflect positively on his own legacy in the field of mathematics.

TLDR; Lambeau is focused on output, with a brute-force approach. He is selfish, and self serving.

Sean: Empathetic and transformational

Sean takes a human-first approach, prioritizing support and guidance for Will before addressing any academic achievements. He focuses on helping Will understand himself first, which is crucial for him to determine what he truly wants in life.

Rather than pressuring Will, Sean provides him with space and leverages his own experiences and vulnerabilities to build trust and connection. This approach ultimately helps Will confront his inner demons and make meaningful progress in his life.

TLDR; Sean is focused on transformation, with a human-first approach. He’s patient, supportive, and authentic.

Four soft skills that can make you a transformational leader

Professor Lambeau is the micro manager we’ve all had (and hated). Sean Maguire is the mentor we all want (and need). It was Sean’s soft skills that enabled his success with Will.

In a leadership setting, soft skills demand a high degree of self-awareness and ongoing effort to develop and refine.

Here are four that will empower you to become a transformational leader:

1. Empathy

2. Communication

3. Collaboration

4. Trust

Lets explore them in detail:

1. Lead with empathy

Being a high empathy leader enables you to understand perspectives beyond your own.

Incorporating multiple perspectives helps you gain a fuller, more balanced view of a situation, leading to better decision-making and more effective problem-solving.

The deeper your insight on what motivates your team and brings them purpose, the stronger your connections will be, and the more productive, happy, and engaged your team will be.

Everything starts with empathy—it’s at the top of this list by design. Each skill that follows below gets much easier with higher levels of empathy.

2. Over-communicate

Early in the movie, Sean establishes a clear expectation for the therapy process: progress can only be made when Will is truly ready to open up. It was direct, concise, and crystal clear (watch the iconic park bench scene here, it’s easily my favorite).

The best leaders are exceptional communicators who consistently share a clear vision, mission, and strategy—and most importantly, they repeat them. The unofficial title of “Chief Repeating Officer” aptly describes top leaders who relentlessly reinforce these messages until they become ingrained. It’s repetitive and even annoying at times, but it works.

Team Communication

As a manager, you are the line between the business and your team.

Your success hinges on how well you can translate top line goals into a vision and strategy that aligns your team and enables them to be successful. 

Vision, values, goals, strategy—over communicate these, be annoying.

Begin every team meeting with the same set of slides outlining them, it gives your team a north star that will keep them aligned and on path.

Individual Communication

This goes double for your relationship with your direct reports. Be clear with your expectations of what “good” looks like, and use 1:1’s to calibrate on how well you are aligned. 

A good gut check here happens during performance reviews: your review and your direct report’s self reviews should be 90% aligned or better. Naturally the occasional review will have some delta, but if you’re noticing most reviews are misaligned, it’s not them it’s you… 

3. Put your team first

“Collaby” is the term my last team coined for collaborating with each other and other teams. It became a core part of our identity and I will never stop using it.

How to collaby as a leader:

1. Plan and strategize together. 

   The vision, mission, and strategy mentioned above should be a combination of top down business needs, and bottoms up inputs from your team.

   Data, insights, and domain expertise from your team are essential for making informed decisions, and allowing them to contribute and participate will give them an incredible sense of purpose. 

2. Make decisions together. 

   Making decisions in a silo sucks for everyone. Use the 90/10 rule:

   • 90% of your decisions should include your team or some portion of it. They’re the experts in their domains, not you. Leverage their knowledge.

   • 10% of your decisions will either be time sensitive or confidential

If you’re feeling this split is anything other than 90/10—recalibrate.

If you’re unable to calibrate to 90/10:

→ Your seats are filled with the wrong people, or

→ You’re in the wrong seat

4. Give people space

Sean's superpower was his ability to create a supportive space for Will, allowing him to come out of his shell at his own pace instead of feeling pressured.

“Space” is a term you need to understand and get comfortable with. Assuming you enjoy space to operate yourself—your team feels the same. Nothing is worse than feeling like you don’t have space. 

There are two versions of feeling a lack of space:

The feeling that someone is watching over your shoulder:

Inserting yourself in your team’s work and making decisions on their behalf shows a total lack of trust and autonomy.

If you feel the need to stay constantly informed about every task or worry that your team will be lost without your frequent guidance, you have a serious issue and addressing this should be your top priority.

There’s no “I” in Team, but there is one in “micro manager”

A lack of clarity on scope or responsibilities:

Imagine being blindfolded and told there’s a cliff edge somewhere in front of you—it could be just two feet away or as far as two miles.

What would you do?

You’d likely be completely paralyzed, frozen, afraid to move an inch. 

Lacking clarity on scope of work is no different (though much less dangerous). It leads to paralysis and indecision. As a leader it’s your job to be crystal clear on your team’s scope of work so they have freedom to move within it.

If they have a football field’s worth of scope but don’t know it, they may as well be in a 5 x 5 yard box. 

Building and leading teams is hard. Some skills may come naturally to you, others may not; some may be easy to learn, others require deep intentional work and practice.

You can be a transactional leader or a transformational leader— which will you choose?

Book recommendation

(In each issue, I'll highlight a book I’ve recently read and enjoyed, or that inspired my writing)

Wanting: The Power of Mimetic Desire in Everyday Life

Wanting explores the concept of mimetic desire, which is the tendency for people to desire what others desire. The book delves into how this unconscious imitation influences our choices, ambitions, and relationships.

For leaders, understanding this can be transformative. It sheds light on how desires and behaviors can be shaped by social dynamics and helps leaders navigate team motivations more effectively. By recognizing and managing these influences, leaders can foster healthier, more authentic interactions and drive more meaningful outcomes.