Page 8 of Falling For My Ex's Older Brother

"Diplomatically."

The corner of his mouth moves — not quite a smile, but the closest approximation Keith allows himself in a professional setting.

"Always."

He leaves without filling the silence with anything unnecessary, which is something I've come to value from him. Through the floor-to-ceiling windows behind my desk, San Francisco sits under a sharp November sky — the bay visible from this height, the morning light cutting clean angles across the Financial District below. I've worked in this office for a long time. The view has never stopped being a useful reference point. There are dayswhen the scale of what's out there is a productive reminder of what's still left to build.

I turn to my correspondence and work through it with the same methodology I apply to every morning — highest priority first, everything else in descending sequence, nothing left in a state of ambiguity. Ambiguity is expensive. I made that determination early in my career and I've never had reason to revise it.

By 10:15 I'm on a call with our legal team regarding vendor agreement terms that need restructuring before the end of the quarter. I identify three points of exposure they've missed, walk them through the revised language I want, and end the call in eighteen minutes. My assistant — Rachel, who has managed my schedule and correspondence for three years with the precision of someone who treats her work as a craft — brings me a coffee without being asked and sets it at the edge of my desk without interrupting the call. It's the last thing Rachel does for me as my employee.

She appears in my office doorway at 11:40. I know from her expression before she speaks that this isn't a scheduling matter or a correspondence question. She has the look of someone who has rehearsed what they're about to say, which means it's personal, and personal in a professional context almost always means one thing.

"Mr. Drake." She steps inside, her own folder in hand.

"I need to speak with you."

I set down my pen and give her my full attention. It's the least I can do. She's leaving. Two weeks' notice, though she offers to extend if the transitionrequires it. Her husband's company is relocating to Seattle. She's been going back and forth on the decision for months — I believe her, because Rachel has never been someone who acts without deliberation. She apologizes for the timing. She thanks me for the years.

I listen to all of it without interrupting. When she finishes, I tell her that her work here has been consistently excellent and that her reference will reflect that accurately. I mean both statements completely. I also feel nothing personal about either of them, which is not a contradiction — it's simply how I'm built. Rachel has been an exceptional assistant. She is also, as of this moment, a logistical problem that needs solving before the end of the business day. Both of those things are equally true and I hold them with equal weight.

She leaves my office with the relieved expression of someone who expected the conversation to go worse. I pick up my phone before the door finishes closing.

"Patricia." My head of HR answers on the second ring.

"Rachel Simmons just gave notice. I need a replacement in place before she's out."

A brief pause on her end.

"I actually have something already in the pipeline that may be worth looking at. Can I come up in an hour?"

"Fine."

I set the phone down and return to the vendor agreement. The operational gap Rachel's departure creates is real but manageable — two weeks is enough time to identify the right candidate and run an abbreviatedonboarding if the person is capable enough to learn fast. I need someone who can manage the infrastructure of my professional life without requiring infrastructure of their own. Rachel did that from the first month. The next person will need to do it at the same level or I'll be running the search again in sixty days, which is not a use of time I'm willing to accept.

I draft three items of correspondence, review the updated Vertex brief Keith sends through at noon, and flag two line items in the quarterly projections that need to be addressed before Friday's board call. At 12:45 I hear the knock I've been expecting.

Patricia enters with a single printed resume and the composed efficiency of someone who has worked for me long enough to know that I don't need context I didn't ask for. She sets it on my desk without preamble.

"This came in two weeks ago," she says.

"Referral through Caleb."

I look at the name at the top of the page.Sutton Kane.

The Caleb reference lands without surprise and without particular feeling. My brother and I don't speak with any regularity — this is a fact of our relationship that neither of us has ever found urgent enough to address. That the call went to Patricia rather than to me directly is consistent with how Caleb operates. He uses the Drake name when it serves him and maintains his distance from everything attached to it otherwise. I don't hold it against him. We madedifferent choices a long time ago and we've both built our lives accordingly.

I set the Caleb reference aside and read the resume properly.

Sutton Kane. Twenty-seven. Based in Los Angeles, currently available following an acquisition at her firm — which explains the timing. Before that, two years in business consulting. Prior to that, a business development role that she held for eighteen months before being promoted internally. Her degree is stronger than either position required. The credentials read like someone who has been operating consistently above her title, which either means she's been underutilized or she's been strategically patient about her trajectory, building the foundation for a move she's been planning longer than her current situation would suggest.

She negotiated a contract restructuring at her last firm that reduced vendor costs by twelve percent. It's noted in a single line at the bottom of her experience section, stated as fact rather than highlighted as an achievement, which tells me more about how she thinks than the number itself does.

She is overqualified for an executive assistant position by a significant margin. I look up at Patricia.

"Why is she applying for an EA role?"

"She's pivoting into tech. Her background is operations and business development — she originally submitted for a role in that track, before your EA position opened up." Patricia maintains the measured tone shealways uses when she's making a case she's already confident in.