Embracing the Cover Letter
You’ve found an open position that fits your goals, at a company that you respect, and you’ve put in the time and effort to fill out their lengthy employee application form and have uploaded the resume you’ve painstakingly modified for the position—an annoyance I’ll discuss at another time. I know how this feels. Then you get hit with another requirement: this prospective employer is also requesting a cover letter to accompany your application. Before you toss your hands up in frustration or, worse, give up on submitting your application because of the additional work, take a moment to appreciate the opportunity that writing a cover letter gives you. Not all job applications require a cover letter.
A cover letter offers you another chance to sell yourself—beyond the bounds of your resume, which is a rather constrained medium. By providing a well-written cover letter, you can demonstrate what would be in it for the employer if they were to hire you and capitalize on their interests. After all, that’s what employers wonder as they review the countless resumes from Indeed, LinkedIn, Monster, and their company’s own candidate portal.
One of my favorite anecdotes that demonstrates the what’s-in-it-for-me approach came from the great Leonardo Da Vinci. In the 1480s, the young Da Vinci was supposedly in need of a job and wrote a letter to the Duke of Milan, Ludovico Maria Sforza—who had a penchant for waging war—authoring it in a way that would pique the Duke’s interests. Rather than focusing on his experience as a painter or sculptor, Da Vinci emphasized his ability as an architect and designer of war machines, weaponry, and other innovations that would give the Duke advantages in battle. In his letter, Da Vinci made unequivocal statements that showed what his skills would do, in a cause-and-effect construct that demonstrated ways to successfully leverage those skills.
Among his many claims, Da Vinci stated, “I will make covered vehicles, safe and unassailable, which will penetrate the enemy and their artillery, and there is no host of armed men so great that they would not break through it. And behind these the infantry will be able to follow, quite uninjured and unimpeded.” Regardless of whether you think Da Vinci was full of bluster and bravado, using decisive language such as “I will”—as opposed to “I could” or “I could help to”—communicates confidence. Such confidence is often contagious. A prospective employer wants to hire people who will do things for them, because they likely understand that outcomes drive success—not potentials or hypotheticals.
Consider how you might demonstrate your abilities to prospective employers by leveraging a similar technique in your cover letters. For example, let’s say that I wanted to highlight my experience as a UXmatters author because I believe this would be an asset to a prospective employer. Rather than saying, “I am a columnist for UXmatters, an online platform through which I share helpful insights with the global UX community,” it would be better to demonstrate how this experience and skillset would be useful to the employer. So I should consider a statement such as the following: “I will leverage my experience as a published author for UXmatters in helping team members communicate effectively with their colleagues and stakeholders.” This would reinforce the fact that a key aspect of any UX professional’s job is gaining others’ support and buy-in through strong communication skills. In this example, I’m painting a picture for the employer to help them understand what’s in it for them when they hire a UX professional with experience in authoring and publishing UX articles. I could help improve the communication skills of others, especially if I were in a leadership position.
Finally, artificial intelligence (AI) tools such as ChatGPT are becoming popular. Could you feed an AI tool some information about your skills and experience and get it to write a decent cover letter? Probably. However, you would be robbing yourself of the opportunity to cultivate your own sales pitch for future interactions. The act of writing and honing your own message better reinforces it in your mind and helps you further clarify your thoughts.
Offloading that work to a bot—that could flippantly pump something out in mere seconds—would eliminate that precious discovery process, through which you could explore tangential paths, leading to other discoveries about your accomplishments, expertise, and desires. The benefits of manually authoring your own cover letter are difficult to quantify. But so is the feeling that hiring managers get when they interview people who have clearly internalized their own authentic charter and can speak of it freely, organically, and adaptively, without its feeling rehearsed—as though the candidate were repeating it from a stock cover letter—or simply artificial.
Showcasing Your Initiative
I’ve come across different schools of thought regarding the benefits of highlighting a side hustle on your resume or showcasing it in your portfolio.
People who are against highlighting a moonlighting gig contend that it could put a potential employer on guard: they might question your commitment to your would-be day job if they were to hire you. This is especially true if your side hustle seems like it could be lucrative or fill a niche that would be difficult for competitors to emulate. They might also wonder whether the candidate would be sufficiently disciplined to avoid mixing side-hustle activities with the full-time job they’d be paid to perform. Would this candidate abuse their company-issued tools and software? Would the candidate lack commitment to their team and its objectives and do something else on company time? Would the candidate simply be biding their time and poised to bolt once their side hustle begins to flourish?
Conversely, the argument for showcasing your side hustle insists that it demonstrates initiative and the self-starter mindset most companies want, but don’t have in significant supply. People who spend their off-hours working on a passion project are also working on themselves, rounding out their skillset and diversifying their experience. Plus, people who hustle in their free time are often the most innovative and adaptable. They’ve also learned to master time management in pursuit of something for which they have passion, regardless of whether they’re paid to do it. Why wouldn’t a company want to invest in someone who could bring these traits to their organization?
I belong to the latter school of thought, believing that illuminating a side hustle is usually a good move—for all the reasons I’ve just stated. That said, there are some nuances regarding what constitutes a side hustle. You should proceed with caution if you think what you’re doing could raise eyebrows. For example, in my case, writing articles for UXmatters doesn’t conflict with my profession as a UX director who works for a global industrial-automation company. In fact, it complements my profession, making me better at my job because I spend time outside the bounds of my paid job thinking about—and writing about—user experience. My employer benefits from my investment in improving my skills.
However, it would be a conflict of interest if my side hustle were designing a mobile app for release in the iOS app store, for a startup company that specializes in predictive maintenance of plant environments, because my full-time gig operates in the same industry and does similar things. In the end, it’s best to use your own best judgment. In most cases, I suggest letting that moonlit gig shine brightly.
Final Thoughts
Given the inflationary concerns, layoffs, and geopolitical conflicts that are causing disruptive ripples in world markets, the year 2023 is already proving to be a difficult time for many job candidates. Maybe you’ve already been affected or might be in the near future. Assuming that you could be in the market for a new position, I recommend that you also invest heavily in crafting a compelling resume and portfolio that clearly demonstrate your skills and experience. I also suggest your having multiple trusted colleagues or mentors review them and give you feedback. But consider taking the other approaches I’ve described in this column as well. You should seize upon any possible advantage in what is likely to be a difficult job market.
Be selective and let your passion and inherent interests factor into your application processes. Employers pick up on those that are compatible with their needs. Embrace the cover letter. It can be a valuable medium for selling what you will do for an employer. And yes, managers do read them! Finally, go ahead and tout that side hustle—as long as it wouldn’t be a conflict of interest or raise employers’ eyebrows. Your initiative and work ethic would make your application stand out in the sea of resumes and applications. 
