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Jack of All Trades, Master of All: The Well-Rounded CEO


CEO Boss Mug

In the ultra-competitive world of scaling businesses, the success of a company is often determined by the strength of its CEO. The job continuously presents new challenges, and, in order to go from good to great, CEOs must constantly evolve and learn.

Being a CEO is often thankless work that requires you to make big decisions and take heavy risks in an unpredictable environment. You need to be a master of good business habits and emotional intelligence, all while earning and keeping the respect of your employees.

*Breathe in, breathe out*

But, probably the most challenging part about helming your organization is balancing the many hats you wear. While a CEO can always hire excellent people to assist them, they still need to at least be competent in sales, marketing, research and development, human resources, design, and a host of other areas of the business.

In an article for Entrepreneur.com — 6 Challenges Awaiting You When Finally You Become CEO — experienced business leader, Joel Trammell, insists its important to acknowledge you won’t be prepared on day one.

Seth Birnbaum, CEO and cofounder of EverQuote, remembered, “When I initially became a CEO, I felt a lot of internal pressure to know how to be a CEO out of the box. But you shouldn’t feel that way. It requires a ton of learning.”

Try Different Roles

Of course, that begs the question, How does one learn to be an effective Chief Executive Officer?  

Since we’re all aware knowledge doesn’t grow on trees, Lauren Kay, founder of Dating Ring, provides this word of advice:

“There are always a million things you can be doing as a CEO, and so a lot of my time has been spent trying to figure out what is worth spending my time on. Every month or two, I take on a new role, and then I try to figure out if that role is vital to our company and how to structure the role, so that I can hand it off to another member of the company, and look for a new hat to try on.”

In their book, REWORK, Jason Fried and David Heinemeier Hansson agree with Kay that sometimes the best way to learn is to do. They begin their chapter about hiring with a page called, “Do It Yourself First.”

“Never hire anyone to do a job until you’ve tried to do it yourself first,” they write. “That way, you’ll understand the nature of the work.” They continue by explaining this experience will allow you to identify what a “job well done” looks like. You’ll know how to write a job description for the role, what questions to ask during an interview, and whether you should hire someone full-time, part-time, or just continue to do the role yourself.

“You’ll also be a much better manager,” they continue, “because you’ll be supervising people who are doing a job you’ve done before.”

You might feel uncomfortable engaging in work you’re not familiar with. You may even feel like you stink at it.

There are really only two ways out of that feeling: you can learn your way out of it or you can hire your way out of it. Fried and Heinemeier believe — before you resort to hiring — it is beneficial to learn first.

Adding to Experience

As you learn a new skill on the job, there are copious ways to reinforce that knowledge. And, as major employers are rethinking the value of a college degree, less formal places of learning can help you acquire the skills you need.

Of course, each individual job and department will have different resources available. In other words, you probably won’t go to the same place to build your marketing chops as you will to dive into human resource training. Blogs such as this one can be a great resource for discovering the best spots to gain knowledge on isolated departments within a company.

But there are a handful of resources that can work, regardless of the skillset you’re learning.

There’s a lot that can be learned by reading articles and blogs, but many have had success receiving college-level training on free schooling sites like Coursera.org. Many other specialized courses can be found on Lynda, Springboard, SkillShare, Udemy, Udacity, and General Assembly in addition to business strategy courses like those from Growth Institute.

Make that Learning Pay

There’s no denying it: being a successful CEO is the most challenging job in the building. The best of the best don’t just understand the workings of the department from which they rose, they have a handle on the full breadth of the organization.

Entering the role having mastered everything an experienced CEO will one day know is an unrealistic expectation, but working hard to gain new understanding and competencies can set the stage for the success of the entire organization.

Trammell identifies five core responsibilities he believes must be done by a chief executive. The more of a holistic view the organization’s leader can earn, the better they will be able to guide their firm through these key duties:

  • Owning the organizational vision is essential. At Align, an integral component of our business software is the One-Page Strategic Plan, which allows company leaders to share their vision for success with the entire team. John Birchfield, the CEO of DSi — a client of Align — said the One-Page Strategic Plan “was pivotal for aligning the work employees did to the overall mission of our company. That did wonders for our employees’ sense of purpose.”

    A CEO who understands each department and can speak their unique languages will be better suited to sharing his or her vision in a way that resonates across the entire organization.
  • One of the most important tasks for a CEO is ensuring the right people are in the right positions. As Fried and Hansson said, doing the work yourself first will allow you to understand what is needed for the job.
  • As we wrote recently on this blog , a CEO is responsible for setting the culture of an organization, from top to bottom and across all departments. An understanding of all departments is required for that work.
  • Trammell outlines how important a leader’s experience across the organization is in their ability to make decisions: “One minute the CEO is discussing a new product, the next a human resources issue — and then along comes a legal issue. It’s impossible for anyone to be an expert in all aspects of the business, yet the CEO is the person tasked with making the decisions.”
  • And finally — and most importantly — the chief executive is responsible for overseeing and delivering the performance of the organization. That requires them to communicate with each department, as well as to facilitate communication between departments and between the organization and external stakeholders.

Of course, communication on that level requires an unparalleled understanding of the workings of his or her company.

That understanding can’t be expected to be there from day one, and it won’t come easy, but the effort to earn it can do wonders for any organization.


Align provides the software solution CEOs and leaders at growing organization need to manage work on strategic priorities across their business.

Schedule a demo today!