Jack of All Trades, or a Master of One

William Shakespeare’s famous quote, “A jack of all trades is a master of none,” is often misused in its partial form to imply that being a generalist is a bad thing. The full quote reads: “A jack of all trades is a master of none, but oftentimes better than a master of one.” The ending phrase implies that those who hold broad knowledge and skills across many disciplines are typically better off than those who are experts in only one specialty.

So how do these competing philosophies apply to the entrepreneurial world? When building a business, some entrepreneurs prefer to be jacks of all trades and learn everything that goes into building and running their business, whereas others focus on being a master in their field and hire specialists in other areas to take care of the rest.

Is one way better than the other? If you explore how each strategy applies to business leaders, you can make a strong case that it’s important for entrepreneurs to take a jack-of-all-trades approach to building and growing a business.

The specialist (or master of one) approach

A specialist focuses on developing deep expertise in one particular area of their business. The founder of a technology company, for instance, may focus exclusively on product development and innovation, relying on other specialists to handle operations, marketing, and other areas of the business.

Specialists’ advanced knowledge and skills allow them to become masters in their field by focusing on and perfecting one aspect of business and delegating all other business functions to respective experts. However, lacking knowledge about other specialties makes it difficult to see the bigger picture and identify critical issues that could harm their business. They may also struggle to establish a cohesive mission and align different parts of their business towards a common goal.

Specialization can also limit flexibility, making it difficult to pivot or adapt to solve new pain points or business needs. Over-reliance on other experts may be risky if the team isn’t strong or lacks enough cohesiveness to overcome significant challenges. Therefore, entrepreneurs should consider gaining at least some knowledge of the various aspects that make business successful.

The jack-of-all-trades approach

There is a certain allure to taking the jack-of-all-trades approach and gaining a broad understanding of the different facets of your business. I believe the best entrepreneurs are strong, deeply involved leaders and problem solvers who possess a well-rounded knowledge of all aspects of running a business, including operations, finance, product development, customer service, marketing, and human resources.

These jacks of all trades can look at the big picture and see how different parts of the business interconnect, identifying problems across different business areas before they arise to make better decisions and mitigate risks.

Being a jack of all trades with broad knowledge and insight helps entrepreneurs develop, define, and convey business goals and values more effectively. They can step into different roles as needed and make informed decisions without the help of specialists, which is particularly helpful during the early stages of a business when resources are limited and founders are forced to wear many hats.

Is there a right way?

It’s better to be a jack of all trades than a master of one. Companies of all sizes benefit from business leaders who have a jack-of-all-trades mentality. Yes, you’ll inevitably hire and depend upon experts who are better at running essential parts of your business, but it’s important to learn about their roles at a high level for several reasons.

First, having a foundational understanding of different job functions will help you develop the right interview questions to find the right talent. Second, once you’ve hired the right experts, understanding their job functions is essential to properly onboarding, managing, and delegating to them. Third, learning about various areas of expertise will help you understand and be able to track KPIs that ensure each part of the company is contributing to its overall success.

Additionally, being a jack of all trades will help you manage the financial aspects of the business. Having a good understanding of all the different parts of your business leads to better decisions about where and how to allocate and adjust spending over time (for example, reallocating funds from marketing to product, product to support, support to sales, sales to marketing, or any other permutation).

If you’re fundraising, you need to be able to answer questions from investors about all different aspects of the business. Investors and shareholders often want to know the details of the budget. Being able to confidently and thoroughly explain why things worked or didn’t work, and outline next steps or how you plan to fix anything that’s not going well, will instill confidence in other people that you know what you’re doing and therefore your team will be able to execute effectively.

The jack-of-all-trades strategy also contributes to building a good company culture. Entrepreneurs and business leaders must be good mentors and role models. If you demonstrate an openness and excitement for learning and find ways to make it fun, your positive attitude will inspire your team to take that approach as well, especially if you’re a growing company. This can encourage other leaders within your organization to become mini jacks of all trades within certain areas of specialty as well (i.e. a chief revenue officer who understands marketing, sales, public relations, paid media, social media, etc.).

Whether you’re a founder of a startup or the CEO of an established corporation, pursuing at least a good understanding of every part of your business will help you build and lead a cohesive and collaborative team that is working efficiently towards a shared purpose, properly vet partners, vendors, and investors who can help you achieve and sustain long-term growth and success, and do a better job at managing the overall trajectory of your company.