Leadership Skills: Important Yet Often Overlooked Attributes

I’ve been reflecting on the characteristics of leaders, whom I define (somewhat broadly) as anyone who leads an entire function in an organization. 

The descriptors most often associated with leaders include ‘visionary’, ‘charismatic’, ‘decisive’, and ‘outgoing’

Those skills are important, particularly when raising funds and hiring top talent. But they aren’t all that matter. 

There are four other characteristics of successful leaders which I find are often overlooked.

Practicing these behaviors sets leaders apart from those who simply execute, whether as individual contributors or as heads of small teams.

  1. Think Long Term
  2. Fix Broken Stuff and Know What Might Break in the Future
  3. Understand Other Functions and What Motivates those Leaders
  4. Approach People Management Proactively


Think Long Term

Leadership requires thinking longer term. Seeing where things might be going, acknowledging that the future is unknowable.

Individual contributors or those who lead small teams might have goals for the week, the sprint (often two weeks), the month, or the quarter.

Leaders should be thinking about the organization over a horizon longer than 1 year. Their task is to set goals for where the business needs to be in the medium term.

At a venture-backed start-up they are able to answer the question of what needs to be achieved to raise another round of financing. At a private equity backed company they are thinking about how the business needs to be performing to create an exciting exit event.

Once the long-term vision is set, leaders then must figure out what actions and resources are required to get there. Knowing that not everything can be done and resources are almost always finite, leaders prioritize the tasks to accomplish. A key element is also deciding those things which won’t be done in the near term.


Fixing Broken Stuff and Knowing What Will Break

Many leadership roles, even at companies that are considered successful, involve fixing broken things. If almost everything is going swimmingly, there is often no need to change leadership and thus fewer opportunities for promotions or new jobs. Leaders inherit functions with broken or highly inefficient processes and systems.

Also required is making informed guesses on what will likely break as the company scales and works towards its 2 year goals. It is always more fun to think of positive outcomes. And yet, good leaders anticipate what might go wrong and plan for it. That planning includes deciding what to fix preemptively and then convincing the organization to make the investment when things are ok. 

Sometimes the decision will be to delay making changes. Acknowledging this decision publicly is equally important. There is always a shortage of time and money requiring leaders to accept and live with inefficiencies, short-cuts and debt (operational, technical or capital) which could lead to future failure.

There will also be unexpected negative surprises along the way. If you don’t like the challenge of fixing broken stuff, or dislike when new challenges repeatedly arise, then leadership in a growing organization is not the right role for you. 


Understand Other Functions

Career progression involves getting really good at a job and then mastering a variety of roles within that function. In most functions this will take a while as there is a fair bit of complexity and different types of skills required of a Head of Marketing or a Head of Finance.

A second characteristic of great leaders is the ability to think cross functionally, beyond their core function. 

The easy part is knowing the goals and priorities of other functional leaders. High quality leaders go beyond the understanding of goals to figure out what motivates other functional leaders. Motivators are usually both extrinsic, such as incentive compensation, and intrinsic, such as their vision for how a top-performing team acts. 

Knowing these two motivators enables leaders to identify likely areas for conflict or lack of alignment between functions.

Leaders must anticipate potential problems and suggest solutions that satisfy the customer, meet the broader business goals, and help the other functional leaders be successful.


Approach People Management Proactively

Organizations are groups of people. And people, though willing to sacrifice and row together for the greater good of the organization, are also interested in getting their goals met while having a fulfilling job.

Leadership requires thinking proactively about people and their career aspirations. 

Going beyond their achievements (against goals) in a particular period and talking with them about how they feel as well as their longer term hopes and dreams. 

Using a sports analogy, leaders must act as both the team manager (optimizing near term performance) and as the employee’s agent (looking out for their long-term best interests and positioning them to get there).


Building a business is really challenging.

Not many organizations grow and thrive for extended periods. A key component to longevity and success is hiring the right leaders. Those who go beyond the basics and also possess the four often overlooked characteristics I have laid out above.

The success of a business depends upon hiring the right functional leaders and missteps in these decisions can set companies back for years. Leaders set the tone for their functions. They create an environment that attracts and retains high quality people, allows for new and better ideas to emerge, encourages effective collaboration, and empowers efficient decision-making. 

Aditya Dehejia

Adi’s experiences as a CFO and HR leader in start-up companies inspired him to start the CxO Leadership Accelerator. He saw firsthand the challenges in building a satisfying career, the importance of leaders in developing people, and the difficulty in building broad business acumen while excelling in your functional role. Prior to his operating career in start-ups, Adi held roles in a growth capital investment firm and in the corporate development and strategy department at a Fortune 500 company. Adi is an active volunteer mentor in the FirstRound Capital and TechStars networks as well as within his University alumni communities. Adi was born in India and immigrated to the US at age ten. He attended Princeton University (graduated with a degree in Politics) and the Stanford Graduate School of Business. He lives in the suburbs of New York City and has two adult sons and two lovable, crazy dogs.

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