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The Job Hunt: Making a Great Impression

Just like any other product process, the job hunt has a series of deliverables that may vary from one “project” to the next. That said, there’s a crucial basic toolset that you’ll want to master for nearly every potential job you apply for.

Write a great cover letter

Unless you have a strong network and know people at the company you are applying for, your cover letter may be the first and only introduction you’ll get. A great cover letter is a well-researched, tightly-crafted story of who you are and why you’d be a great fit for the specific role and company you are addressing.

Do your research

What we do look at are cover letters. Cover letters say it all. They immediately tell you if someone wants this job or just any job.

Jason Fried, Basecamp

The research you uncover in the first phase, covered in Thinking of Yourself as a Product, is crucial to crafting a great cover letter. At its most basic, your cover letter should address:

  • That you understand the role and that your skills and experience are a good match,
  • That you are interested in the company and the products or clients they work with,
  • And that you are someone the company would benefit from hiring.

Some employers make writing your cover letter dead simple by asking you to submit very specific responses. They may ask you to rate yourself on specific skills or ask explicit questions as part of the job description. Make sure to address these first and in detail, but share your story as well.

Spit and polish

Once you’ve answered all the basic requirements, focus on polishing it. Keep it short and sweet. Your cover letter should be an introductory tease that makes your potential employer want to know more. Edit out anything superfluous.

I’ve talked with numerous employers about what makes them skip over a candidate. The single biggest answer? Typos and grammar mistakes in the cover letter and resume. When your potential employer has a large pool to choose from, even the simplest mistakes become an easy way to weed out potentials. Your cover letter should be flawless.

There are plenty of tools available to find and fix these basic mistakes. Start with the built-in spell check and grammar check tools available in most editors. But don’t rely solely on machines. Ask your friends and family to review it as well. You can even hire people to review your cover letter through sites like Fiverr. (Though you can also hire people to write cover letters there, I’d recommend against having someone else write your cover letter.)

Address your cover letter to someone specific. If you can’t find a specific recruiter or hiring manager to address your cover letter to, address it to leaders in your area of interest. At a small company, this could be the president/CEO and any VPs or directors in your specific area of expertise (engineering, design, etc.). Use the company about page, LinkedIn, social media, or blogs to find these names. NEVER address a cover letter to Dear Sir/Madam or To Whom It May Concern unless you are truly not interested in the position.

Beyond the basic cover letter

Over the last few years, I’ve eschewed Microsoft Word for writing my cover letters. I now almost exclusively create custom web sites for cover letters. The rare exception to this is companies with enterprise recruiting systems that require PDF or Word documents. Even then I typically try to create a more in-depth cover letter and reference that from within my Word document.

With a web cover letter, you can include more than just text. You can give a quick overview of your portfolio, with deeper links to specific projects. You can provide quotes from former coworkers, clients, and managers. You can add links for employers to follow you on social media or contact you directly.

A web cover letter has several advantages over a typical Word document:

  • You can have more than just text. Yes, a basic cover letter should be quick to read and easy to engage with. (This can be your email or Word precursor.) But I can’t think of a single recruiter I’ve talked with who hasn’t appreciated the extra attention and details available in a web cover letter.
  • It can be responsive and interactive to easily engage the reader no matter what device they read it on.
  • You can update it and add links as you progress through the hiring process with specific companies. Some companies have follow-up exercises that require you to answer questions or work out problems. You can link to these responses straight from your cover letter, and help reinforce your message.
  • You can track visitors and see whether your letter gets engagement. Whether you build your own custom back-end to alert you when someone visits or use tools like Google Analytics, you can know when someone has actually looked at your cover letter or not. (If you’re really interested, you can even add events and triggers to know what links your visitors look at.)

Craft your resume

There are plenty of great references for creating great resumes. Here are some of the standouts from the many resumes I’ve reviewed over the years:


  • Be creative in the design. A unique layout or concept can help you stand out from the crowd.
  • Customize your resume for the jobs and companies you’re applying for. Obviously your experience and education aren’t going to change, but what you choose to focus on from one application to the next may. When applying for a more technical position, focus on your technical experience at each job. When applying for a design-oriented position, focus on those strengths instead.
  • A great summary or overview should be just a sentence or two, but tells a story of what drives you.
  • Use active verbs for job descriptions rather than passive. Be specific about the result of your actions. An example: Utilized Google Analytics to learn more about visitors could be rewritten as Increased visitor engagement 100% year over year by analyzing popular content in Google Analytics.
  • Be honest on your skills. Don’t list skills you don’t consider strengths (unless you’d like to do more of them).
  • Skill ranking is a touchy subject. I’ve had recruiters tell me that it helps them to understand where I’m strongest, while I’ve had others tell me that “only amateurs rank their skills”. I prefer to be honest and rank my skills on a rough 5-point scale; I would definitely advise against using percentages or anything too granular. (What’s the difference between 65% and 75% knowledge of a skill?) I always leave room for improvement in even my highest ranked skills.
  • The farther back you go in your resume, the less detail you need.
  • Just like a web cover letter, a web-based resume offers a lot of advantages.

In general, the really ‘creative’ applications seem to be from utter nutters.

Andy, Mint Digital


  • Don’t go overboard on the creativity. Make sure your resume is still easy to read and print. Remember that your ultimate goal is to get hired, not to create the most amazing, interactive resume.
  • Don’t list unrelated skills or hobbies. If your passion is snowboarding, it only makes sense to list it on your resume if you’re applying for a job at Vail or Burton.
  • Don’t be overly verbose. List only the most important things you did in each position. (This is where tailoring to the job you’re applying for can help.)

Share your process and decisions in your portfolio

A great portfolio does more than share your work visually. It tells the story of your work. What was the purpose of this project? What challenges did you overcome to produce it? What are you most proud of? What led to specific decisions in the pieces you choose to display? What was your role on the project?

Don’t just show a series of screenshots. Tell the story of the project through them. Give insight into the decisions you made, explain the process as it unfolded for the project, and explain why the project is an important part of your portfolio.

Go above and beyond

How badly do you want the job? For a job you’re really excited about, go above and beyond to make a great first impression. Here are a few ideas to really show a company that you’re passionate about working for them:

  • Do they have a blog? Write your first blog post for them.
  • Do they create products? Play around with their product(s) and come up with a new feature idea. Share prototypes, and discuss your process and design decisions.
  • Craft a landing page for a specific product or service they offer.
  • Create a style guide based on their existing products or site.
  • These are just a few starter ideas. Look at what the company does and be creative.

While these types of projects might be considered spec work by some, they also show that you are passionate about the company and willing to invest your time to show it. Ultimately, you want to show potential recruiters and hiring managers that you are not just looking for any job, but that you want to be a part of their team specifically.

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