Leadership

Leadership… you know it when you experience it (sometimes) but it’s intangible by nature and escapes efforts to define it broadly. Organizational characteristics (size, industry, location) complicate things further. Different business environments require (and reward) differing types of leadership — a one-size fits all definition may satisfy the need for “answer” but it would quickly lose relevance when applied.

There is plenty of material on what makes a leader — books, podcasts, videos, tweets etc. Some of it tries to ground conclusions in research (but not much of it) which, given the ephemeral nature of the subject, feels strained – looking at the past in an effort to build a pattern for the future. While I think most would agree there are some enduring/universal precepts there is material variance everywhere. Personally, I see leadership as a more dynamic “idea” with some prescriptive behaviors and skills that are ever evolving.

While acknowledging the challenges, there’s still value in trying to build a framework to evaluate and aspire to. If you’re reading this, you’ve likely worked for various leaders/bosses/managers and have developed your own checklist of leadership “dos and don’ts.”  Depending on your experience there may be a lot more “don’ts” than “dos” which underscores another point — being a leader is not easy.  

Below is my checklist of skills and behaviors exhibited by the best leaders I’ve worked with, observed or studied. 

Things to keep in mind

Leadership Skills​

Strategy Development

Employees, customers and investors respond to a well-crafted strategy thats articulated well. I haven’t experienced a leader be successful who wasn’t a strong strategic thinker (and communicator). It doesn’t guarantee success but you need it. If you review the current CEO’s who are considered the “best”, they all have that in common. They develop a ‘north star’, can sell it exceptionally well and create company purpose.

Communication

Well-spoken consistent communication with employees builds up equity and turns skeptics into believers and precedes employee buy in. When paired with a strong strategy, you began to see something special. 

Technology Acumen

I do not mean someone who a software engineer would describe as “technical.” It’s hard to name one operating area of a business that has not been materially impacted by technology in the last 20 years. Great CEOs must maintain a current POV of potential disruptions (positive and negative) and their impact on their business, customers and partners. Internally, the explosive adoption of Saas point-solutions for all aspects of operations and the related security implications require CEOs to understand how and what is running their business at a detailed level.

Financial Acumen

Relying on a strong CFO is not enough. The best leaders have a deep understanding of income statements, cashflow, balance sheets, revenue recognition, accounting etc. From my experience, these are typically learned “on the job” as most CEOs do not come from a finance background. 

Hiring

Human capital drives business. While I’m sure it’s possible, I haven’t seen companies sustain success with a mediocre C-team (ie the CEO’s direct hires). When the CEO hires poorly or can not attract top talent, you often see it reflected throughout the organization. Same goes for talent management — if the CEO struggles there, you can expect the organization to do the same.

Behaviors

Detailed Oriented

Striking the balance between micro-management and a detailed understanding of business operations is a thing. Leaders who are seen as too “in the weeds” run the risk of demotivating employees and turning them into passive observers however you can not manage an organization when you don’t understand it. Great leaders develop a working model of operations, customer needs and partnership dynamics and constantly tune it by receiving as much unfiltered information as they can manage.

High Emotional EQ

Increasingly, today’s employees expect a leader to “see” them. To be able to relate directly with their challenges and acknowledge them. It sounds trite to say a “leader who cares” but that’s what is expected. Events over the last decade have created a high-level of general distrust that must be overcome especially with younger employees who are entering the workplace with a high-level of skepticism and expectations.  

Accountable & Authentic

It’s easy to celebrate wins — a strong quarter, promotions, a big new customer, a new milestone reached. It’s harder to acknowledge mistakes, poor hires, failed initiatives and even harder to cultivate an environment where conflict and tough questions can be asked by and of all employees without it feeling personal.  The trust required for employees to let down their guard, feel vulnerable but not let it impact them emotionally or make them fearful is only possible if the leader is modeling it daily. 

 

Resilient

We all experience challenges, disappointments and setbacks but great leaders who embody the Stockdale Paradox of acknowledging reality/challenges without wavering from belief can pick people up when those bumps hit the business.  

Decision Making

The ability to expedite and delegate decisions is a skill of high performing CEOs. Slow playing decisions gives an appearance of indecisiveness and lack of vision. This can negatively impact morale and erode faith with your most ambitious and talented employees (A-players) as they will start to questions managements ability to run the business.

Poor delegation skills are a sign of a lack of trust (CEO to managers/employees) and a sub-optimal operating structure. The reduced autonomy will be felt and demotivate employees and managers. Great CEOs  create an operating framework that scales decision making. They should lead high-level decisions and be consulted when consensus can not be reached – not micro-managing or requiring managers to seek their counsel.

In conclusion...

 Your most talented people want to engage in work that is meaningful and they want to invest their time in a company and leadership they believe in. Great leadership is a strategic advantage and can be built. 

To learn more about strengthening leadership at your company or any other topic I’ve written about, connect with me via LinkedIn or set up a call.

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