Sean Oliver

If you’re applying cold, you’re playing the hardest game.

Systematic relationship-building with people at or above the level you’re targeting is the real key. It took me 15 months to land my current role at Microsoft, an old coworker finally made the intro that led to an offer. That didn’t happen by accident—it happened because I stayed visible, relevant, and in motion.

Getting hired isn’t about having a perfect resume. It’s about removing friction and making it easy for someone to say yes.

What's the difference between quitting and stopping?

Quitting is the abandonment of effort toward a result. A resignation. An end.

Stopping is a pause.

Restarting is implied. A break. A moment to recharge.

Then we begin again.

3 habits to build a searchable paper trail:

1. After a meeting where something got decided, write the decision down. One paragraph: who owns it, and by when.

2. When you finish something, say so in the thread people will search later. Never only in a DM.

3. Every week, send your manager three wins and the three things you're focused on next.

The work nobody wrote down belongs to whoever remembers it.

New rule:

No new course or tool purchases till you make 3 things the LAST course was designed for.

Most people treat AI like a magic button. Plug in a prompt, cross your fingers, and wonder why the output is mediocre.

The technology isn't the bottleneck. People are.

Most people operate at first-order thinking: reacting to what's directly in front of them without asking what happens next.

Second-order thinking is what separates real productivity from novelty. The people who crush it with AI treat it like a thinking partner—probing, spotting gaps, and refining follow-ups.

It’s never about prompt hacks. It’s about mental clarity.

I was wandering through UW's cherry blossoms when my phone rang.

The Microsoft recruiter's somber tone had me bracing for rejection—until he delivered the news I'd been hoping for.

My reaction? I literally yelled at him for "messing with my emotions." (Not my proudest professional moment!)

What do you call it when:

You write down a to-do item you've already done, just so you can immediately cross it off?

Nobody overhears good work from home. There is no hallway to catch it in.

Almost five years of remote work taught me to trust paper trails and bread crumb records more than anyone's memory.

The work nobody wrote down belongs to whoever remembers it.

Mistake: "Let me know if you hear of anything."

Fix:

- Name 3-5 target companies

- List 2-3 job titles

- Ask for an intro to the hiring manager

Specific asks get acted on. Vague ones get "sure, will do."

Being laid off doesn't make you radioactive, even if it feels like it.

In 2008 I left Starbucks a few weeks before they laid off 12,000 people. I got out clean. Some of my friends didn't.

One of them was Tay. He thought I was crazy for leaving "The Bucks". Then he got cut.

He told me who went quiet. The people who said "let me know if there is anything I can do to help" stopped picking up the phone. Not because they were bad people. Because offers are easy to make, but require action to fill.

So when he called, I answered.

That's it. That's the whole system. I started a list. Not a spreadsheet, not a CRM. Just names: people recently impacted, companies making cuts. When something moves, I check the list.

The check-in itself is nothing. No advice. No job leads unless I actually have one. Just: I saw the news, how are you doing?

When it happens, I check in. Not a LinkedIn heart, or comment. A call.

A layoff isn't radioactive. It's not contagious. Answering the phone is not a hard problem.

Most people just don't.

I used to spend hours dreading performance reviews.

Three habits changed that:

1. Document the criteria for the role

2. Capture weekly breadcrumbs instead of relying on memory

3. Train AI to frame the impact in my manager's framework

The result? Saved hours of drafting and got the best review feedback in the last 2 years.

Applying online feels productive. You're one of hundreds in a stack nobody reads.

85% of jobs are filled through networking, and hiring managers often have a shortlist before a role hits the board.

Increase your surface area. Make sure the right people know you before they need you.

Most people announce they're looking for work.

An announcement gets filed away in an afternoon.

Send a recurring update instead: where you're looking, where you're interviewing, and how someone can help this week.

There is a question we don't ask often enough in our careers: "Who benefits from me staying put?"

Incentives are real. Until your growth is incentivized, you find yourself stagnating.

Stop waiting to be chosen. Start making your mission, your needs, and your wants known.

This is a fantastic approach for building up your hype doc/yayme file/resume bullets https://t.co/01qV9MTpBc

Your boss isn’t responsible for your career.

HR isn’t responsible for your growth.

Your mentor isn’t responsible for your next promotion.

Nobody cares about your success as much as you do. Act accordingly.

Folks who are better at representing their impact and the perception of that impact win.

Strategic thinking comes down to connecting daily tasks to the bigger picture.

See how your current work fits into the larger puzzle. Treat it like a map and actively explore the spaces that feel less familiar.

Don't just spot patterns—use what you notice to make one proactive adjustment today.

Clarity comes from intentional focus.

Amazing resource https://t.co/RftxYYs6JO

Must keep momentum and active engagement. https://t.co/lu2s3jorTE

Everyone upset with last night’s results… https://t.co/5f1XbZvksi