Notes from Lessons from the Trenches

This article was originally published on Substack, where you can also get Job of the Day posts (always interesting, mostly remote).

I recently spoke at Seattle Interactive Conference, with a session entitled “Lessons from the Trenches: Insights for Job Seekers,” where I shared some of the larger takeaways from my Getting the Nod client work. Thanks to Seattle Interactive for the opportunity and to all who attended my presentation. For those of you that couldn’t make it, here’s the summary and a link to the slides.

The largest theme to my session was that a necessary step to taking the next step in your career is to understand your journey thus far. Given how many times I’ve written about narrative and/or storytelling that shouldn’t be surprising. Still, I’ll sum up some of the larger points.

When I ask a new client why they’ve come to me it’s common for them to say they “just” need help with their materials, that their resume isn’t getting attention and they don’t even know what to say in a cover letter (if they’re including them at all). It’s rare that that’s actually where the real work is needed. There are always some modifications that can be made to both, but by and large the issue at play is that they don’t even know what they’re trying to say. The reasons for that are varied, ranging from not having seriously considered that question to not even having the mental energy or imagination to craft an answer because of something like trauma or burnout. Regardless of the reason, the task at hand is less about the Xs and Os of crafting the “perfect” document, and is more about the human behind those documents, understanding their goals, motivations, strengths, fears, etc.. That process looks more like a therapy session than late-game play calling. (Note: I am not a therapist nor do I pretend to be.)

To get at the heart of my clients, I have to ask A LOT of questions. I shared some of my favorites so people can work through them on their own. Having those answers be more top of mind can lay the groundwork for the entire job seeking process (and career management overall). You should understand why you do what you do and like what you like, even if you never need to write that down or say it aloud. Those are things that make us unique, that make us human. AI can’t do that.

One of the places where that “human" element can be utilized is in the cover letter. Rather than being only a part of an application, I consider cover letters to serve multiple roles, operating perhaps more as an organizational tool for the job seeker than even as an introduction to a recruiter. An applicant should be clear on why they’re excited about a role, why they’re a good candidate, and what their weaknesses might be. That sort of self-reflection pays dividends.

The other reason to understand more about yourself is to be able to align your efforts toward roles, companies, and industries that are compatible with you, your goals, and your values. You aren’t just looking for a job, you’re looking for the right job and this it's helpful to know what the right job is. There are a variety of tools that can help you better understand your professional priorities and values and I share a few.

My hope with this presentation was to share how so much of managing your career or job search is understanding yourself. Doing that leaves you in a better position to convey your ideas in any context, whether written or verbally. More importantly, that sort of prep work can only help you feel confident - that’s the hope anyway. All of that feeds your ability to embrace your own agency.

Here’s the presentation (you can download the slides as well). Feel free to reach out if you’ve got questions and if you’re now curious to learn more about coaching, feel free to set up a free introductory session.