Lesa's Cover Letter Writing Approach

This week – I’m attempting to frame my thoughts about cover letters in 2026. I first covered this topic in episode #77 – “Cover Letter – Yes or No?”

My overall stance on cover letters hasn’t changed since that first episode – unless the posting specifically tells you NOT to provide a cover letter, do it. And I haven’t seen any postings that tell you NOT to provide a cover letter.

Virtually all ATS (Applicant Tracking Systems) will allow you to attach your cover letter as a PDF when applying.

Here are three reasons not to submit a cover letter:

1.     You don’t have enough interest in the position to take the time to customize a cover letter. If you aren’t willing to take the time to make that letter specific to that company and that position, you may be doing yourself harm by submitting a cover letter. In other words, don’t bother to apply at all.

I would add that if there are errors in grammar, spelling, and punctuation in your cover letter, you are doing more harm than good. Make sure the cover letter is as error-free as your resume. 

2.     You are not providing the reader with any new information. If all you’re doing is rehashing the exact verbiage of your resume, you aren’t helping yourself.

3.     If all you’re doing is telling them how you would improve the company, save that for the interview. You risk coming across as a know-it-all by providing this information in the cover letter.

When to include a cover letter (NOTE: the default is to include a cover letter; these four situations below are the times you really MUST include a cover letter.)

1.     When you have a personal connection or referral. Mention the name of the person who has referred you to the company and position.

2.     You have a connection to that company. If you’ve had an internship there or worked with that company in some other capacity, be sure to mention in the cover letter.

3.     You are making a pivot to a different job function or industry. The cover letter gives you the opportunity to walk the reader through this decision.

4.     You believe there will be an obvious objection to your candidacy. For example, why you are applying for a seemingly lower job title, or are willing to work in a different geographic region.

Here’s how I approach writing the cover letter: I have already identified my client’s brand attributes (what makes them different; what they bring to the table that differentiates them from their competition) in writing their resume.

I then take three of those brand attributes and create a paragraph for each in their cover letter.

I’m not repeating what is in their resume verbatim; rather, I am reconstituting the facts from their resume in their cover letter.

Here’s an example from one of my clients, with identifying information removed (client is applying for jobs in Global Programs Strategy):

Strategic Leadership. Throughout the eight years I have been with Company X in multiple customer success roles, I have displayed the ability to:

»         Develop and execute highly effective healthcare strategies that have delivered transformational impact

»         Research, collect, analyze, and act upon data to improve the client experience, enhance services and service delivery, and eliminate/minimize roadblocks to utilization of services

»         Lead cross-functional teams to implement new technologies, resolve complex problems, grow revenue, streamline processes, and enhance client satisfaction.

Growth. I currently have a single client, representing a significant percentage of Company X’s total revenue. I stepped into this role in 2020 as a result of exceptional success with previous clients, and I have continued to exceed expectations. We’ve grown the account by more than 56% in that time, including $35M with the launch of a novel in-home care solution.

In this and earlier roles, I consistently earned 9/10 Net Promoter Scores by providing exceptional responsiveness, increasing utilization, and identifying cost savings opportunities. As a result, my client currently realizes a 1.51:1 ROI from our services.

People Management. One of the greatest satisfactions I derive from my work is the opportunity to coach, mentor, and otherwise assist in developing my direct reports and others. From technical skills to soft skills to learning how to advocate for themselves, I am highly effective in both formal and informal professional development. While the flat organizational structure of Company X has only afforded me one direct report, I have extensive experience in influential leadership.

One more example, for a client seeking a role as Senior Director of Strategic Market Intelligence & Growth Strategy:

Transforming the Market Intelligence Function. At both Brand A and Brand Z, I was tasked with standing up the analytics function as a business driver, rather than a reactive data-gathering function. To achieve this, I brought together key stakeholders from across the organizational landscape, hired highly skilled teams, and introduced systems and processes to deliver mission-critical information to decision makers at lightening speed. Turning the market intelligence function into an organization’s mandatory hub has facilitated enhanced planning, improved marketing ROI, and significantly decreased time-to-insight.

Strategic Advisor. My ability to transform the analytics function could only be achieved with an executive presence, strong business acumen, and the ability to translate complex data into audience-specific, easily digestible chunks. My ability to connect with people, gain their buy-in, and deliver what they need when they need it has been a hallmark of my career. I am equal parts knowledge fountain and highly approachable colleague.

Identifying Opportunities. Throughout my career, I have specialized in transforming raw data into high-resolution insights that go far beyond standard reporting. At Brand A, I didn't just track the “what” of behaviors; I uncovered the “why” behind their behavior patterns. By identifying these hidden drivers and untapped opportunities, I enabled the organization and its partners to pivot from broad marketing to hyper-targeted campaigns based on specific consumer behaviors.

The Document & Coaching Package is designed for current job seekers who want world-class marketing documents, a targeted, proactive job search strategy that gets results, and skill-building around how to network, interview, and negotiate compensation. To schedule a consult: https://calendly.com/lesaedwards/zoom-meetings2