How to Ask for Help Without Sounding Helpless (The 3-Part Ask)
Three parts, in order. Context, what you tried, the specific ask. Stop making your manager do two jobs.
I’ve spent twenty years watching smart new grads make the same five mistakes in their first month. I wrote the book I wish someone had handed me — and I write this site for the people still opening the envelope.
I was born in the early ’80s, which means I remember answering machines and card catalogs but still grew up to be the person on the team who fixes everyone’s Zoom. I’m a digital native who doesn’t want to be an influencer. I met my spouse on an app, but I also like paper books. Across a twenty-year career, I’ve worked for executives who dictate emails to assistants and alongside engineers who live inside Figma and GitHub. That bilingualism — old-guard and new-guard — is most of what qualifies me to write about early-career life.
I started out in the mailroom at the William Morris Agency (now WME), one of the top talent agencies in the world. On paper, the job was sorting packages. In practice, it was a graduate program in professionalism: learning how Fortune 500 executives talk to their assistants, how agents guard client relationships, and how every email you send in a high-pressure environment is a reputation bet. That job is where I learned that the unspoken rules are the real rules.
After business school at USC Marshall (undergrad at NYU), I joined a large consulting firm in a business-strategy and product-management practice. My clients were Fortune 500s — investment banks, movie studios, telecoms — which meant I spent most of my twenties parachuting into other people’s organizations and learning their internal weather. I worked with clients in the US, Canada, Europe, and Japan, and had the uncommon luck of seeing how national culture changes corporate behavior firsthand.
Today I lead a department at an e-commerce technology company, where I manage managers and spend most of my time coaching — helping people who were the smartest kid in their college class figure out how to be a good first-year professional. I’ve interviewed and hired hundreds of people. I’ve also had to put people on performance-improvement plans and, occasionally, let them go. That’s the uncomfortable half of the job that almost no career book talks about, and it’s a lot of why I wrote this one.
I pick topics where the gap between what you were taught and what the job actually requires is widest.