Pivotside Chat: Ask Laura Sheehan Anything About Resumes and Cover Letters

On February 17, 2026, Laura Sheehan (Georgetown University) hosted a second “Pivotside Chat” session with the Pivot with Purpose community to take questions about resumes and cover letters.

While the previous “Pivotside Chat” session acted as a review of the fundamentals of a clear and effective job search strategy , this event drilled down on more specific questions. Indeed, we know the significance of a good resume or cover letter, especially in today’s challenging job market.

In previous sessions focusing on resumes, we’ve crafted our resumes and made our federal experiences private-sector ready . Also, in our cover letter sessions, we’ve been taught how to best use AI tools in our drafting and how to scan job postings for key terms and phrases. Recently, we’ve even discussed the recruiter’s perspective  on resumes.

While all of these sessions have been instrumental in helping us understand resumes and cover letters’ importance, many of us still may have lingering questions.

Thus, in this session, Laura Sheehan returns to answer your these questions: How many versions of a cover letter should we have? Who should we address our cover letters to, if the job description does not list the hiring manager? How long should our private-sector resumes be? How much AI should we use?

In this second interactive Q&A session, Laura Sheehan answered any (and all!) questions about resume and cover letter best practices. We hope this refresher also helps direct your job-searching efforts and assists in your transition to a new career!

Other Previous Sessions

Please feel free to browse our other previous sessions to access summaries, video content, and more information about our other events!