Someone asked me recently what makes a placement successful from our perspective. “Is it just when people stay in positions long-term?” she wondered. “Or when families give you great feedback?”
Those things matter, sure. But the placements I’m genuinely proudest of after twenty years aren’t always the smoothest or easiest ones. Sometimes they’re the matches that almost didn’t happen, or the situations where we helped families and staff figure out what they actually needed versus what they thought they wanted, or the times we took risks on unconventional approaches that ended up working beautifully.
I can’t share identifying details obviously – discretion matters in this work. But I want to tell you about some Chicago placements that stuck with me over the years and why they make me feel like we’re doing something meaningful here.
The House Manager Who Wasn’t
A family reached out from Lincoln Park about five years ago needing a house manager. They described wanting someone to coordinate vendors, manage household projects, oversee their housekeeper and landscaper, and handle day-to-day operations. Pretty standard house manager stuff.
During our consultation, I kept asking questions trying to understand what they really needed day-to-day. Turns out both parents worked intense hours in demanding careers. They had three kids under ten in multiple activities. Their actual problem wasn’t household operations – they had decent systems and reliable vendors. Their problem was they couldn’t manage family logistics, kid schedules, household coordination AND demanding careers without someone drowning.
“You don’t need a house manager,” I finally said. “You need a family assistant who can handle kid stuff plus some household coordination.”
They pushed back initially. A family assistant sounded less impressive than a house manager. But we talked through what would actually make their lives better versus what sounded good professionally. They agreed to trust the recommendation.
We found them someone perfect – a woman who’d done both nanny work and household assistance and could blend childcare support with operational coordination. She wasn’t managing complex renovations or overseeing estate operations. She was making sure kids got to soccer practice, coordinating with their housekeeper about timing, handling grocery runs, and managing the million small details that made family life chaotic.
The placement worked so well that they’re still together five years later. The kids adore her. The parents’ stress levels dropped dramatically. They’ve told us multiple times it changed their quality of life.
What makes me proud about this one isn’t that it was complicated – it wasn’t. It’s that we pushed back on what they asked for and helped them figure out what they actually needed. A lot of agencies would’ve just placed a house manager, collected the fee, and moved on when it didn’t work great. We took time to understand their real situation.
The Estate Manager With the Messy Resume
I got a call from a candidate about three years ago who’d seen we worked in Chicago. Her resume was all over the place – she’d done property management, business operations for a small company, hospitality work, and some personal assisting. Nothing screamed “estate manager” in the traditional sense.
But when we talked, she was clearly smart and capable. She understood systems thinking. She’d managed people. She handled complex logistics. She just hadn’t worked in traditional household settings and didn’t know that world existed as a career option.
Most agencies would’ve passed. Her resume didn’t fit the mold. But I saw potential.
We worked with her on understanding household employment culture, what families expected, how to talk about her transferable skills. Then we found a family in Oak Brook who needed someone to manage their home and coordinate their small business operations that ran out of a home office. The role was half estate management, half business operations support – kind of unusual but perfect for her background.
I was honest with the family. “Her resume doesn’t look traditional, but I think she’s got exactly what you need.” They trusted our judgment enough to interview her.
She crushed it. Been there three years now and they’re thrilled. She brought business-level operational thinking to household management in ways that traditional estate managers might not have. The unusual background ended up being an asset.
This one makes me proud because we didn’t default to conventional thinking. We looked at capabilities versus just credentials. And we matched an unconventional candidate with an unconventional need instead of trying to force square pegs into round holes.
The Placement That Almost Wasn’t
A family contacted us from Gold Coast about hiring a private chef. We found them a candidate who seemed great – excellent training, solid experience, good references. Interviews went well. Everyone was excited.
Then during final negotiations, the family balked at the salary the chef needed. They wanted to offer $15,000 less than what the chef required and what we knew was appropriate for Chicago’s market given her experience.
We had a hard conversation with the family. “This is the market rate for someone with her qualifications. You can offer less, but she won’t accept and you’ll only access less qualified candidates at that compensation.”
They were frustrated. They really liked her but didn’t want to adjust their budget.
Here’s where we took a risk. We suggested they structure the position differently. Fewer work hours, more focused responsibilities, some flexibility that the chef actually wanted anyway. The revised approach fit their budget while meeting the chef’s compensation needs for reduced hours.
Both parties had to compromise on their initial vision. But the modified arrangement ended up working better for everyone. The family got a talented chef within budget. The chef got appropriate pay and a schedule that gave her time for other professional projects she cared about.
They’re two years in now and it’s been excellent. The chef recently told us this arrangement lets her maintain the work-life balance that makes her sustainable in private service long-term.
What makes me proud is we could’ve walked away when initial expectations didn’t align. Instead, we problem-solved until we found a creative solution that actually served both parties better than their original plans.
The Housekeeper Everyone Else Rejected
A candidate came to us who’d been turned down by multiple other agencies. She was in her late 50s, had been housekeeping professionally for 25 years, had limited formal education, and English was her second language. Other agencies looked at her and saw someone hard to place with wealthy Chicago families who often had specific expectations.
But when we met her, she was lovely. Proud of her work. Incredibly skilled at what she did. Impeccable references from families she’d worked for over many years. Just didn’t interview in the polished way agencies thought wealthy families expected.
We had a family in Winnetka whose housekeeper was retiring after 15 years. They were devastated – she’d been part of their family forever. They cared way more about finding someone kind, skilled, and reliable than someone who interviewed impressively.
We presented our candidate honestly. “She’s not going to dazzle you with sophisticated vocabulary. But she’s exceptional at the actual work and her references are glowing.”
The family hired her immediately. They saw what we saw – genuine quality in the work that mattered. She’s been with them four years now and they couldn’t be happier.
This placement makes me proud because we didn’t write someone off based on superficial criteria. We looked at actual skills, work ethic, and character. And we matched her with a family who valued the same things.
The Family We Almost Declined
A family reached out from Lakeview about an estate manager. During our initial conversation, some warning signs emerged. They’d had high turnover with previous staff. They were vague about why people left. They had somewhat unrealistic compensation expectations.
I almost declined to work with them. But something made me dig deeper.
Turns out they’d never really understood how to employ household staff professionally. Previous hires had been somewhat random – friends of friends, people they found on Craigslist. They’d never had clear employment structure, appropriate compensation, or realistic expectations. They weren’t bad people. They just genuinely didn’t know how household employment worked.
We had really honest conversations about what needed to change. They needed to increase their compensation budget. They needed to treat this as professional employment with proper structure. They needed to understand that great staff require investment.
To their credit, they listened. They adjusted their approach completely. We found them an estate manager who fit what they actually needed once expectations were realistic.
That was four years ago. Still together. The family has told us multiple times that learning how to do this right changed everything for them. They’ve since hired other household staff and approached those hires professionally from the start.
I’m proud of this one because we could’ve walked away from a family showing red flags. Instead, we invested time educating them and they were willing to learn. The result was a successful placement and a family who now knows how to be good household employers.
What These Stories Share
Looking back at the placements that make me proudest, they share some common themes. They involved really listening to what people needed versus just what they asked for. They required us to look beyond surface-level fit to understand deeper compatibility. They meant taking risks on unconventional approaches rather than defaulting to standard playbooks.
They also all involved honest conversations – sometimes uncomfortable ones – about money, expectations, or reality versus hopes. We pushed back when we needed to. We educated when people needed education. We problem-solved when initial visions didn’t align.
Most importantly, they all put long-term success ahead of short-term ease. It would’ve been simpler to just place the house manager the Lincoln Park family thought they wanted. Easier to pass on the candidate with the messy resume. More convenient to walk away when budget negotiations got difficult.
But taking extra time, having hard conversations, and thinking creatively about solutions created matches that genuinely work years later. That’s the whole point.
What Success Actually Means
Here’s what I’ve learned after twenty years: successful placements aren’t always the ones where everything goes smoothly from day one. Sometimes they’re the ones where we had to work through challenges, adjust expectations, or try unconventional approaches.
Success means families and staff both feeling good about relationships years in. It means people staying in positions because they genuinely work, not because they’re tolerating situations while looking for something better. It means both parties feeling like the relationship adds real value to their lives.
Success also means we helped people figure out what they actually needed. That might mean talking a family out of hiring a role they don’t need. Or helping a candidate see that their unconventional background is actually an asset. Or working with both parties to structure arrangements differently than either initially envisioned.
The placements I’m least proud of? The ones where we just went through motions. Where we placed someone adequate because it was easy even though we knew better fits existed. Where we didn’t push back on unrealistic expectations because it was simpler to let people figure it out themselves. Those placements might’ve technically “worked” but they didn’t create the kind of uncommonly good matches we’re actually trying for.
Why We Share This
I’m telling you these stories not to brag about our placements but to be transparent about what we actually value and how we think about this work. We’re not just filling positions or collecting fees. We’re trying to create matches that genuinely improve people’s lives on both sides of the employment relationship.
That means sometimes doing harder things than the straightforward path would require. It means having uncomfortable conversations. It means risking losing business by being honest about what we think will and won’t work.
Chicago families deserve agencies willing to do that work rather than just processing placements transactionally. Household staff deserve the same. The placements that make us proud are ones where we did right by everyone involved even when that wasn’t the easiest option.
After twenty years, those are the placements I remember. Not the simple ones that worked fine. The ones where we made real differences by paying attention, thinking creatively, and caring about outcomes beyond just completed transactions.
That’s what uncommonly good matches actually means to us. And that’s what we’re still working toward with every placement we make.
