Howard, a hiring manager at Espera Health, interviewed four VP candidates over three weeks. He liked three of them. Then he went quiet.

Not because anything was wrong. He got busy. He took a long-planned vacation. And underneath both, if he’s honest, he genuinely didn’t know which of the three to move forward with.

Two weeks later, he resurfaced, ready to schedule final rounds.

By then we were scrambling. Two of his three finalists had gone quieter themselves — not rejecting anything, just slower to respond, clearly fielding other conversations. We spent those two weeks doing damage control: checking in, keeping them warm, racing to get Howard back in the room before one of them signed somewhere else. That race isn’t over. It’s the one we’re running right now.

Here’s the part that gets missed: nobody rejected anybody. There was no bad interview, no lowball offer, no red flag. Candidates don’t go cold because they found something better. They go cold because they stopped hearing anything at all, and something else showed up in the meantime.

Silence reads as disinterest, even when it isn’t.

A slow “no” still tells a candidate where they stand. A slow nothing tells them nothing — so they fill in the blank themselves, usually with the worst-case version, and start returning other recruiters’ calls.

I get why the stall happens. Liking three candidates is genuinely harder than liking one. You’re not just evaluating people anymore, you’re trying to rank them, and ranking is uncomfortable when there’s no obviously wrong answer. So the calendar fills up, the trip gets taken, and “I’ll figure it out next week” becomes the plan.

Meanwhile, the market doesn’t wait for you to get back from vacation.

If you’re the hiring manager

The stall almost never happens because you don’t know what you want. It happens because you haven’t built in a forcing function to decide. Put the decision on the calendar before the interviews even start — a specific day you’ll rank the finalists, not a vague “sometime after we’re done.” If you’re about to be out for a stretch, tell your recruiter and your candidates that upfront. A known delay is a non-event. An unexplained one is how you lose people.

If you’re the candidate

If you’ve finished a final round and gone quiet on, that quiet is rarely about you. It’s usually a calendar problem on their end, not a verdict on your interview. Ask for a specific date you’ll hear something, not just “soon.” And if that date keeps moving without a real reason, that’s useful information too — about how decisions get made at that company, not just about this hire.

If you’re the recruiter in the middle

This is the part nobody sees. You’re not just managing a search anymore, you’re managing a countdown on candidates who have no idea one started. The job becomes buying time honestly — real updates, real timelines — instead of vague reassurance that quietly turns into a lie the longer the client stays dark.

The best candidates aren’t sitting around waiting to find out if they made the cut. They’re taking other calls. Every week of silence is a week you’re betting they won’t.

If you’ve got a search stuck in the “I’ll get to it” phase — on either side of the desk — hit reply. I’d like to hear where it’s stuck.

I shot terribly at golf last week. By hole three, I’d already stopped keeping score. By hole five, a guy who had to be pushing 75 — shuffling more than walking, no backswing to speak of — beat me hole after hole without ever seeming to try. That’s when I understood something about hiring I’d been trying to put into words for years.

I don’t play golf. Never have. No clubs, no lessons, last time I set foot on a course was a decade ago. But I’ve watched plenty of it — a pro tournament in person 25 years back, a few bored Sunday afternoons on TV — and somewhere along the way I convinced myself I’d hit the ball straight and long a few times, like the pros do. That was the expectation I walked in with. It was wrong.

The Ego Problem

Then the 75-year-old set me straight without ever knowing he was doing it. He didn’t hit far, didn’t hit hard, didn’t do anything that looked impressive. He just put the same short, boring shot in the same spot, over and over, and quietly walked away with the hole every time. My ego did not enjoy this. I wanted to be the guy who could show up cold and still hit it well. Instead I got shown up by a guy who’d clearly done nothing but the fundamentals for fifty years.

Somewhere in there I let the ego go and just started watching the ball, checking my form, no expectations. By hole eight, I got a bogey — one stroke over par. Small win. And immediately, a new expectation showed up: beat that on hole nine. I didn’t. I missed it.

We show up with an expectation, and when we hit it we feel like we’re crushing it. Miss it and the whole day feels wasted — even though an hour earlier, a bogey on a course I’d never played would’ve counted as a win. Half the time the expectation itself is just ego wearing a disguise: we don’t only want to do well, we want to look like we were always going to.

The VP Who Skipped the Process

I watched the same thing play out in a real search a few weeks ago. We had a VP-level candidate — sharp, credentialed, exactly what the hiring manager wanted on paper. But from the first conversation, all he focused on was the outcome: the comp number, the title. He treated the interview process as a formality, did one round with the hiring manager, and stopped there. He never gave anyone internally a reason to fight for him — to push past the initial comp band, to justify the flex in title he wanted. He might have gotten everything he was asking for. People do get exactly that, when they’re excellent enough in the process that the company decides they’re worth bending for. Instead, he lost the opportunity early — focused on the score, never played the round.

Who was I to expect a good round after never really playing the game? I’d watched enough golf to think I understood it. Watching isn’t playing. No amount of wanting the outcome substitutes for putting in the unglamorous rounds nobody sees.

What This Means for Your Search

What are you expecting right now that’s putting pressure on you it doesn’t need to — a number, a title, a “yes”? Quiet it down. Focus on the process. The results show up eventually. And if they don’t, at least you didn’t spend the whole thing pissed off about a number you never controlled in the first place.

Last week, one resume line made me stop scrolling. A C-level marketing exec had listed her Uber Rider rating — 4.9 out of 5. Fair, that’s brag-worthy. I have no idea what mine is. Probably not a 4.9.

It made me realize: candidates will put almost anything on a resume to stand out. I’ll forget most of hers by next week. I won’t forget that 4.9. Her background is solid, though maybe a notch light on seniority for this role. Still, she’s earned a call. I’m hiring for a creative marketer, and her resume made the case before she said a word.

Quick confession: my LinkedIn lists “2nd place, tennis champion vs. the backboard.” I’ve hit hundreds to thousands of balls in a row and still lost. The backboard is undefeated.

Standing out means doing something different, louder, or better than the crowd — genuinely, not gimmicky. Standing out for the wrong reasons? Fix it, don’t spin it. Stop trying. Just be yourself, loudly.

Don’t list a 3.2 GPA. Skip it entirely unless it’s a 3.9 or higher — anything less is an admission, not a flex. Swap it for a stat that says something real about you.

At Ramp Talent, resumes like this are exactly what we’re trained to spot — the line that tells us more about someone than their title does.

We got an urgent request last week: find product candidates, fast, for a hiring manager who needed to move now.

We did our job. Three strong candidates, sourced and screened (hat tip, Nathan). Then the hiring manager told us he was headed on vacation for two weeks. This is a candidate experience problem, not a scheduling problem

Great for him. Now we’re stuck dancing, keeping three good people warm with nothing real to tell them.

Here’s the truth nobody wants to say out loud: the interview isn’t what makes or breaks a hire. The silence after it does.

Why the gap gets so long

Everyone blames the recruiter when a process drags. That’s almost always the wrong target. The recruiter is the one person actually fighting to close the gap. Here’s what’s really happening on the other side:

An executive is busy and keeps pushing the call. Another candidate is mid-process and the hiring manager wants to compare notes before deciding. Something’s on fire internally that has nothing to do with your search. Or it’s July and half the panel is at the lake.

The higher up the org chart, the worse it gets. A CEO who reschedules twice isn’t rejecting your candidate. They’re running a company, and your search is not the only thing on their plate.

Four interviews in two weeks is a win. Say that out loud to anyone who’s run a search. Most processes don’t move that fast, and the ones that do have a recruiter fighting calendars every single day to make it happen.

What the gap does to a candidate

Candidates don’t hear “the exec is busy.” They hear silence, and silence sounds like rejection every time.

Four days between interviews and they’re prepping. Three weeks and they’re refreshing their inbox, replaying the last interview in their head, and quietly taking calls somewhere else. By the time you’re ready to move again, you might be moving on an empty seat.

A slow process isn’t neutral. It’s actively bleeding you candidates while you sit around trying to feel certain.

The fix: never let a candidate go a week without hearing from someone

This is the part most companies get wrong, and it’s fixable in one sentence: every candidate should hear from someone on the hiring team at least once a week. Not a status update. A real touchpoint — 5 to 10 minutes, a call, or thoughtful update email can go a looong way.

If the hiring team can’t make that happen, the recruiter does it instead. That’s the job.

Don’t overthink this. It doesn’t need to be a formal check-in with an agenda. “Hey, still moving, the VP’s back Monday, here’s what’s next” takes five minutes and kills 90% of the anxiety a candidate is sitting with. Silence is what costs you the candidate. A five-minute call almost never does.

If you’re the hiring manager

Block your calendar before you launch a search, not after you fall for a candidate. Every day a great candidate sits with no next step is a day a competitor closes them first. Speed isn’t a favor you’re doing the candidate. It’s how you win.

If you’re the candidate

Most delays have nothing to do with you. Stop building a case against yourself out of silence. Push your recruiter for real updates, show up with as little ego as possible, and drop the expectations entirely. Prepare like every interview is the only one that matters, follow up, and let the timeline be whatever it’s going to be.

The interview is one hour. The space between interviews is where the hire actually gets decided.

No explanation. No real discussion. Just a quick “pass” buried in a hiring panel thread.

Something about it didn’t sit right with me.

We’re in the middle of a brutal C-level search right now. Real feedback is hard to get. The interview panel keeps shifting. Some candidates sail through the first screens and others — equally strong, sometimes stronger — don’t. It’s the kind of search that makes you question yourself. But giving up was never on the table.

We were close to closing this role a few months ago. Then we lost our top candidate to one of the hottest AI companies out there right now. You can guess which one. Back to baseline we went — researching, sourcing, screening, calling in favors. And every time we surface a strong candidate, their LinkedIn profile gets dissected like a doctoral dissertation defense.

That’s how Trent (not his real name) almost slipped through the cracks.

He got the cold-Slack rejection. No real reasoning attached. When I started asking around, I realized nobody on the panel could actually articulate why he wasn’t a fit. They just hadn’t loved him enough to say yes — which isn’t the same as a real no.

So I kept him warm for a couple weeks while I picked my moment. Then I went to the decision-maker and pushed back — not on them, on their reasoning. They heard me out. Trent’s back in the process, and his first interview is on the calendar.

I could’ve let it go. Accepted the non-answer and moved on to the next resume. But I’d done my homework — I knew the role, I knew the criteria, and I knew Trent fit. Whether he ends up being “the one” is still TBD. But I’m glad I pushed for the truth instead of the path of least resistance.

Here’s what I keep coming back to: a lot of hiring decisions aren’t decisions. They’re flinches.

A panel reads ten profiles in a row, gets tired, and the eleventh one gets a “pass” that’s really just decision fatigue wearing a business suit. Nobody’s being malicious. They’re just not being asked to explain themselves — so they don’t.

If you’re a hiring manager: next time you reject a candidate, make yourself say the actual reason out loud. Not “not feeling it” — the specific, defensible reason. If you can’t articulate one, that’s information too.

If you’re a candidate: a rejection — especially a fast, silent one — usually says less about you than you think. Plenty of “no’s” are really just nobody pushing back on a maybe.

If you’re navigating a search where the right person keeps almost getting passed over for reasons nobody can quite explain, that’s exactly the kind of mess we like untangling. Hit reply — I’d love to hear what’s going on.

PS — sending this a day early since half of you are already mentally on a boat for the 4th. Happy Fourth.

Last week a C-level client called to brief us on two open VP roles at his company. He walked through the open roles, the ideal candidate profile, the usual stuff.

Then, almost as an afterthought, he mentioned he’s quietly job hunting too.

The company’s growing. He just doesn’t love the industry anymore, or the day-to-day of his own job.

It’s easy to think of clients as hiring machines — people who just want roles filled, no inner life required. They’re not. They want to be proud of where they work too. They get tired of jobs that don’t fit, same as anyone.

But it puts us in a strange spot.

This guy reports directly to the CEO. He’s about to hire two VPs who’ll report to him — VPs who have no idea their new boss might be gone before they’ve finished onboarding.

Do we say something? To who? When?

Here’s where we landed: we’re not going to tip off candidates or rattle anyone inside the company. Instead, we’re going to ask our client directly — is he sticking around long enough to see these hires settle in, or do we need to start shaping the transition story now? Better to know the real timeline than to guess.

Questions to ask before accepting a VP or leadership role

If you’re a candidate: don’t assume the person who hired you will be your boss on day 90, let alone day one. Ask about leadership stability before you sign. Ask the hiring manager point-blank what their own career plans look like. The answer — or the hesitation — tells you something.

It’s fine if a boss is on their way out. It’s not fine to hide it from the people joining because of them.

To this client’s credit, he’s been straight with us about all of it. If things go well, we’ll help him land his next move too. That’s the job.

We don’t know yet if he’s staying long enough to see these hires through, or if we’ll be having the transition conversation sooner than he thinks. We’ll let you know how this one plays out.

Last Friday, my dog Coco got a tapeworm. By Sunday she’d vomited for two straight days and was declining fast enough that we hospitalized her.

I’m not great with vet tech work — that’s my wife’s department — but I am good at one thing: paying vet bills.

And sitting in that vet’s office, I couldn’t stop thinking about the question nobody likes to ask out loud.

What happens to the family who doesn’t have the money to pay the vet bills?

Does the vet treat the dog anyway and eat the cost? Find her a new family who can pay? Or does the bill decide whether Coco lives? I don’t know the answer, and I hope I never have to find out. But I know this: if you can’t cover a real vet bill, that’s worth sitting with before you bring home the dog. Love isn’t the expensive part. Emergencies are.

Coco’s home now. She’s recovering. We got lucky, and I know it.

Here’s where it got me, though.

Ramp Talent runs executive and technical searches — the kind where a bad placement costs a client six figures and a year of momentum. At that level, I’m not just reading a resume. I’m trying to figure out who someone actually is underneath the version of themselves they’re presenting on the call. And almost everyone I talk to is dealing with something I will never see.

Maybe they spilled coffee on their pants five minutes before the call and are sitting there with a straight face. Maybe their dog is at the vet right now. Maybe their kid was up sick all night. Candidates have to perform “fine” because the job is on the line — so they do.

Here’s how I actually account for that when I’m running a search:

I weight the second conversation more than the first. The first call is performance. Everyone’s rehearsed, caffeinated, and on their best behavior. The second call — especially if I catch them on a rough day, distracted, or running five minutes behind — tells me more about how they’ll actually show up under pressure on the job.

I ask what’s hard right now, not just what they’re proud of. “What’s the hardest part of your current role” gets a more honest answer than “what are your biggest wins.” The wins are rehearsed. The hard part usually isn’t, and it’s where I learn how self-aware someone is.

I give weird moments room instead of penalizing them. If a candidate’s energy is off, I don’t write them off in the first ten minutes. I ask a direct, human question — “how’s your week going?” — and actually listen to the answer before I decide what their flat tone means. Half the time it has nothing to do with the job.

I trust references over polish. Polish is buyable. A former manager telling me how someone handled a bad quarter is not. At the exec level especially, I’d rather hear one honest story from a reference than watch another flawless interview.

None of this is about lowering the bar. It’s about making sure the bar I’m measuring against is the real person, not the version of them built for a 30-minute call.

The best way to assess a candidate beyond their interview performance: ask what’s hard right now, not what they’re proud of.

If you’re a candidate, here’s the coaching version of all this: you don’t owe anyone your tapeworm story, but you do owe yourself a little honesty about your own state. If you’re having a brutal week, don’t pretend you’re not — name it briefly and move on. “Quick heads up, it’s been a chaotic week, so bear with me if I’m a little scattered” takes five seconds and buys you enormous grace. The interviewers worth working with will respect it. The ones who don’t were never going to give you grace anyway. And when you get the “what’s hard right now” question, don’t dodge it with a humble-brag. A real answer, with a little vulnerability in it, is what actually makes you memorable after the tenth interview of the week.

Don’t let your dog get a tapeworm. And the next time someone on a call seems a little off, remember — you have no idea what they’re sitting through to be there. The good interviewers ask. The good candidates can say it out loud.

Q: How do you assess a candidate beyond their interview performance? A: Weight the second conversation more than the first, ask what’s hard right now instead of what they’re proud of, give off energy room instead of penalizing it immediately, and trust references over interview polish.

Q: What’s a better interview question than “tell me about your biggest win”? A: “What’s the hardest part of your current role right now.” Wins are rehearsed. The hard part usually isn’t — and it tells you how self-aware someone really is.

Q: As a candidate, should I tell an interviewer I’m having a bad day? A: Briefly, yes. A five-second heads-up like “it’s been a chaotic week, bear with me” buys you grace from the interviewers worth working with — and costs you nothing with the ones who weren’t going to give you grace anyway.

Last week a hiring manager asked me a question that stopped me mid-call: “How do we screen for candidates who actually use AI?”

He was hiring a VP of Growth Marketing. He wanted someone fluent in AI. But he had no idea how to tell the difference between someone who really uses it and someone who just says “AI” a lot in interviews.

Fair question. Because here’s the weird thing about AI right now:

It’s like a drug people use privately.

Plenty of people use it every day and won’t admit it at work or school. There’s still a vibe that it’s cheating. Cutting corners. Not “real” work.

I get why. But used right, it can 10X your output.

So let me be the first to tell you: I use AI. A lot. You can stop reading now if that offends you.

I use it to write this newsletter. I use it to pressure-test which candidates are the strongest fit for a search. I use it to get better at anything I’m trying to get better at.

Maybe you use it and you’re proud of it. Maybe you use it and you’d never admit it, because you’re worried people will think you’re not “authentic.” Maybe you don’t touch it at all.

I’m not here to tell you what to do.

I’m here to tell you the stigma is costing people — on both sides of the hiring desk.

Here’s what I’ve learned: the more I use AI, the more I realize how much I don’t know. And the thing I value most about it? If I tell it to be brutally honest with me, it will be. No sugarcoating. No trying to please me.

(If I don’t tell it to be honest, it turns into a professional butt-kisser. Ask for the truth. Always.)

That’s the real skill, by the way. Not prompting tricks. Truth-seeking.

Your job with AI — and mine — is to proofread what it spits out, fact-check it, check the sources, and use it to get to the truth faster. It’s not always right. It won’t replace you. But it will make almost anyone faster at their job.

So back to the hiring manager’s question. Here’s where this lands for you:

If you’re a candidate: use AI to prepare for your interviews. Feed it the job description and your resume, and tell it to grill you — honestly — on your weak spots. You’ll walk in knowing exactly which questions you should be sweating.

If you’re a hiring manager: use AI to prep too. Drop a resume in and ask it what you should probe. The gaps, the vague claims, the conveniently missing dates. Then in the interview, don’t ask “Do you use AI?” — everyone says yes. Ask them to walk you through the last real problem they solved with it. The people who actually use it light up and get specific. The people who don’t, stall.

The tool is the same on both sides of the desk. The advantage goes to whoever stops treating it like a secret.

The best interview question for AI skills isn't "Do you use AI?" It's "Walk me through the last real problem you solved with it." One gets you a yes. The other gets you the truth.

PS — The first draft of this post was written by me. I’d show you, but like every first draft, it was shit. The version you just read was improved by AI and fact-checked by my own eyes. That’s the whole point.

This Happens a lot…

When we meet a prospective client for the first time, they almost always ask a question that surprises me:

“Do you actually screen candidates or do you just send resumes?”

To me, that seems like such a basic question.

But then I remember there are plenty of recruiters who do exactly that. They collect resumes, forward them to a hiring manager, and hope something sticks.

The other day, someone in my network saw that we were recruiting a VP of Product and immediately introduced me to who they described as “the best VP of Product ever.”

The problem?

They hadn’t read the job description.

The candidate may have been fantastic for a hardware company, but this role was for a legal AI company. Different industry. Different customers. Different challenges. Different experience.

A great candidate for one company can be completely wrong for another.

This Made Me Realize

Most people think recruiting is matching resumes to job descriptions.

That’s part of the job, but it’s only a small part.

Great recruiting requires understanding dozens of variables that don’t show up on a resume:

• Industry experience

• Technical skills vs. the job

• Company stage

• Leadership style

• Team dynamics

• Compensation expectations

• Career motivations

• Remote vs. office preferences

• Growth trajectory

• Communication style

Then the work really begins.

The candidate has to connect with the hiring manager.

The hiring manager has to connect with the candidate.

The interview team has to align.

The compensation has to work.

The timing has to work.

Any one of those things can break the deal.

I’ve also noticed that the best hiring managers approach interviews with curiosity. They want to understand a person’s story, what motivates them, the challenges they’ve overcome, and how they think.

The hiring managers who struggle often want to spend as little time as possible evaluating people while still expecting a great outcome.

Unfortunately, hiring doesn’t work that way.

This Means For You

Whether you’re hiring your first employee or building an executive team, remember this:

Hiring is a team sport.

Forwarding resumes isn’t recruiting.

Recruiting is understanding both sides of the equation.

You need to deeply understand the company, the role, and the hiring manager.

You also need to deeply understand the candidate, their motivations, strengths, concerns, and goals.

The magic happens when those two sides align.

The best hires rarely happen because someone had the perfect resume.

They happen because someone took the time to understand what success actually looks like and found the person who could deliver it.

This happened.

I was in Phoenix last year when I started noticing Waymos everywhere.

Not one or two. Everywhere.

They looked impersonal. A little eerie, honestly. No driver. No distraction. Just a self-driving car doing one thing — driving.

And then I pulled up next to one at a red light and glanced over at the car beside me. The driver was staring at his phone.

The robot was more focused than the human.

Back home this week, my town started freaking out about a new AI data center being proposed nearby. Everyone had an opinion. Energy usage. Water consumption. The end of the neighborhood as we know it.

Nobody was freaking out about the golf courses using the same water to keep grass green for a sport that, let’s be honest, is a pretty goofy game.

Here’s a thought — what if we built AI data centers in the ocean? Or in outer space? Some people are exploring this. We already put telescopes up there. Satellites. The International Space Station. Why not the servers powering the next era of human intelligence? The engineering challenges are real, but so was landing on the moon. If the pressure of energy and water consumption forces scientists and engineers to think differently about where and how we build these things, that’s not a bad outcome. That’s innovation doing what it always does — finding a way.

Just leave the water alone. And maybe start with the golf courses.

Which made me realize.

We imagine troubles selectively.

We worried the internet would destroy society. Then we gave everyone a smartphone and stopped worrying about the internet.

We worry about artificial intelligence taking our jobs. But I use AI tools every single day — in recruiting, in business development, in content creation — and my job is still here. More than that, I am more productive, more efficient, and delivering better results for my clients and candidates than I ever have before.

I’m old enough to remember when the internet was slowly rolling out inside companies. Some employees had access. Others didn’t. I was a fresh college hire with internet access while Larry, the night shift sanitation supervisor, wasn’t allowed near it.

That seems insane now. But that’s exactly how we treated a technology that changed everything.

AI in the workplace is that moment. Right now. Today.

The professionals asking how do I use AI well are going to look back at this era the way we look back at Larry and the internet. The ones imagining troubles are going to look back wondering why they waited.

Which means for you.

If you’re a job candidate — how are you using AI in your job search and in your work? Not just to polish your resume or generate cover letters, but to think better, prepare deeper, research companies faster, and show up sharper in interviews? AI-powered job searching is already separating top candidates from the rest. The question is which side of that line you’re on.

If you’re a hiring manager — are you asking candidates about AI tools and AI skills in your interviews? You should be. Not to catch them using it, but to understand how they think with it. The future of hiring is not finding candidates who avoid AI. It’s finding candidates who use AI as a force multiplier — while still possessing the critical thinking, resilience, and problem-solving skills to perform when the technology fails them.

The best hiring teams in 2026 are already screening for this. The ones who aren’t are going to fall behind.

AI recruiting tools, AI-powered candidate screening, and AI-assisted hiring processes are not replacing great recruiters and great hiring managers. They are amplifying the ones who know how to use them.

The troubles we imagine about artificial intelligence are almost always bigger than the troubles we actually face.

I have two client meetings and a few solid interviews today. I’m going to imagine good things.

You should too.

— Ben

P.S. Build the AI data centers in the ocean or outer space if you have to. Just leave the water alone. And maybe start with the golf courses.

A lesson in executive recruiting, hiring delays, and missed signals: why top candidates quietly disappear, how hiring teams lose momentum, and what noticing problems earlier can teach us about leadership, business, and decision-making.

One of the most underrated business skills is noticing.

Not intelligence. Not hustle. Not AI.

Noticing.

The ability to notice what other people ignore.

A shift in energy. A delayed response. Increased urgency. Silence. Friction. A change in tone.

Recently, we lost a senior-level candidate to one of the fastest-growing companies in tech.

No, I’m not sharing names. That’s not the point.

The point is: the signals were there.

We just didn’t act on them aggressively enough.

The candidate started taking days to respond to simple questions and emails. Then he’d surface again, answer a few things, and ask more questions about compensation, timing, and when the hiring company planned to make a decision.

He even gave us a deadline.

Meanwhile, the hiring company kept stretching the process.

Another interview. A new stakeholder. A little more waiting.

At the same time, they were developing an internal referral candidate while remaining highly confident in our top candidate.

On paper, everything looked fine.

In reality, momentum was quietly dying.

Then the text came:

He was withdrawing and accepting another offer.

And frankly? I couldn’t argue with it.

It was a damn good offer at a damn good company.

How could we compete?

We probably couldn’t.

But we could have noticed faster.

The signs we missed

• Slower response times from a highly engaged candidate

• Increased focus on compensation and timing

• Repeated questions about urgency and decision-making

• A firm deadline that felt more real than we treated it

• A hiring process that kept expanding despite perceived momentum

• Confidence replacing urgency

One of the biggest executive recruiting mistakes I see is assuming top candidates will simply wait.

They won’t.

The best candidates usually have options.

And momentum matters.

The easy answer would be blaming compensation, timing, market conditions, or the candidate.

The harder answer?

We saw smoke and acted like there wasn’t a fire.

I take responsibility for that.

Could I have been more direct with the hiring team? Yes.

Could I have pushed harder and been even more blunt about the risk of losing the candidate? Absolutely.

I noticed what was happening but didn’t do enough to get others to notice with the same urgency.

That part is on me.

This lesson goes beyond recruiting.

How many problems in business (or life) quietly announce themselves before they become expensive?

Customers stop responding.

Your spouse feels distant.

A top employee becomes disengaged.

Sales calls feel colder.

You stop working out.

You know something feels off.

But instead of addressing it, we tell ourselves a story:

Everything is probably fine.

No news becomes good news.

Until it isn’t.

As humans, we’re quick to credit ourselves for success and blame circumstances for failure.

But growth usually starts with noticing.

Noticing earlier.

Noticing patterns.

Noticing what people aren’t saying.

The smartest person doesn’t always win.

The richest company doesn’t always win.

But the people who care deeply, notice earlier, and act faster?

They create an advantage.

One of the more interesting recruiting challenges is not finding candidates.

It’s helping hiring managers make a decision.

I have a client right now who likes to see a lot of candidates. The challenge is that what he likes in one candidate is often different from what he likes in the next one. So naturally, the response becomes:

“Let’s see more candidates.”

We reviewed the job description together.
We rescoped the role.
We aligned on priorities.
We adjusted compensation and background requirements.

Still… more candidates.

This happens all the time in hiring.

But honestly, this isn’t just a recruiting problem. It’s a modern life problem.

We live in a world with unlimited options.

Too many books to read.
Too many Netflix shows.
Too many productivity systems.
Too many shoes.
Too many LinkedIn opinions.

I can’t even buy shaving cream anymore without going down a 45-minute rabbit hole comparing ingredients, reviews, Reddit threads, and “top 10” lists.

At some point, you have to pick something.

Hiring works the same way.

The Best Hiring Managers Know When to Decide

A great hiring process is not about interviewing 27 people hoping the perfect human magically appears.

It’s about getting clear on:

• What outcomes the role actually owns

• What experience truly matters

• What skills are trainable

• What personality traits fit the culture

• What “good enough to win” looks like

Then interview candidates who align with that criteria.

Not every great candidate has a perfect resume.

Some people interview better than they look on paper. Others have unconventional backgrounds but solve problems better than candidates with cleaner resumes.

If a candidate peaks your interest, talk with them.

Then give a thumbs up or thumbs down.

Move forward.

Too Many Options Creates Fake Progress

Reviewing endless resumes can feel productive.

Sometimes it’s not.

Sometimes it’s just decision avoidance disguised as thoroughness.

Meanwhile:

• The best candidates get hired elsewhere

• Teams stay understaffed

• Work slows down

• Internal stress increases

• Hiring managers burn unnecessary cycles interviewing

The longer the process drags on, the harder the decision often becomes.

My Recommendation for Hiring Teams

In most cases, interview 3–5 strong candidates.

If nobody hits the mark:

• Revisit the scorecard

• Adjust the compensation

• Re-evaluate the requirements

• Clarify expectations internally

• Then continue the search

But eventually, you need to make a decision.

No candidate will check every box.

And no amount of additional resumes will completely eliminate hiring risk.

A Question Beyond Hiring

This idea applies outside recruiting too.

What options are you sitting on today?

Too many business ideas?
Too many books?
Too many strategies?
Too many podcasts?
Too much analysis?

At some point, focus matters more than options.

Pick the path that best aligns with your criteria.

Move.

You can always adapt later.

But sitting still and endlessly reviewing options is rarely the strategy that creates momentum.

— Ben Martinez
Founder, Ramp Talent

AI is becoming a massive advantage in business.

But there’s a downside that hiring teams are quietly starting to notice:

Some candidates are losing the ability to think through problems without it. I heard a term the other day (Hat Tip to Chamath) that describes what I have been noticing, it’s called Resilient Thinking.

One client, let’s call them ACME Soap, noticed that some younger marketing candidates could create polished AI-generated work all day long, but struggled in unscripted situations. Brainstorming. Strategy discussions. Explaining why something would work instead of just generating output.

Another client, we’ll call them Espera Health — encourages engineers to use AI during coding exercises. But many candidates still fail because once the AI output breaks, they can’t troubleshoot the problem themselves.

That’s one of the hidden cons of AI:

It can create the illusion of competence.

You can sound smart.
Move fast.
Generate impressive-looking work.

But if you don’t understand the fundamentals, eventually it shows.

The customer asks a hard question.
The strategy changes.
The code fails.
The CEO pushes back in a meeting.

And someone still has to think.

AI is incredible when it amplifies capability.
It becomes dangerous when it replaces critical thinking, curiosity, and problem-solving.

The best candidates today are not anti-AI.

They’re AI-enabled people with resilient thinking.

Let me say something that most recruiters won’t:

A lot of hiring problems have nothing to do with candidates.

They start with the company not being honest about where they are—Point A.

What companies say vs. what’s actually true

What they say:

“We need a Senior Software Engineer.”

Reality:

• The codebase is messy

• No clear product roadmap

• Leadership changes direction weekly

• The last two engineers quit

That’s not a “Senior Engineer” problem.

That’s a stability and leadership problem.

What they say:

“We need a VP of Sales to scale revenue.”

Reality:

• No consistent pipeline

• Weak product-market fit

• Founder still closing all the deals

• No repeatable sales motion

You don’t need a VP of Sales.

You need someone to build the engine from scratch—or fix the one that’s broken.

What they say:

“We need a Head of Marketing.”

Reality:

• No clear ICP

• Messaging is all over the place

• No attribution

• Expectation is “make us go viral”

That’s not a marketing hire.

That’s a strategy reset.

Why this matters (and costs real money)

When Point A isn’t clear:

• Job descriptions become generic

• Interviews become inconsistent

• Candidates get confused

• The wrong person gets hired

And now you’ve:

• Burned $30K–$100K+ in recruiting fees

• Lost 3–6 months

• Damaged team morale

All because no one slowed down to define reality.

What great hiring managers do differently

The best ones I’ve worked with are brutally clear about Point A.

They say things like:

• “Our team is underperforming and I don’t know why yet.”

• “We’ve outgrown our current leader.”

• “We need someone who can come in and challenge everything.”

That level of honesty changes everything:

• Better candidate targeting

• Cleaner interview process

• Faster decisions

• Stronger hires

A simple framework you can use tomorrow

Before you open a role, answer this:

1. What is broken right now?

2. What has already been tried?

3. What would success look like in 6–12 months?

4. Is this a builder, fixer, or scaler role?

If you can’t answer those clearly…

You’re not ready to hire.

Final thought

Most companies don’t fail at hiring because of a lack of talent.

They fail because they skip Point A.

And in recruiting, skipping Point A is expensive.

Most people aren’t tired from working too hard.
They’re tired from working on things that don’t matter.

That’s the uncomfortable truth about entrepreneurship.

The job isn’t just to work hard. It’s to do the kind of work that feels uncertain, exposed, and sometimes inconvenient… but actually moves something forward. Real work isn’t clean. It’s not always impressive. And most of the time, it doesn’t look like “productivity” from the outside.

It’s sending the message you’ve been putting off.
Following up again when you don’t want to.
Having the conversation that could go sideways.

It’s not building polished slide decks that no one opens.
It’s not tweaking spreadsheets that don’t change decisions.
And it’s definitely not doing work just so it looks like you’re doing work.

There’s nothing more draining than putting hours into something that goes nowhere. You prep for a meeting, and your work doesn’t even come up. You send a summary, and no one reads it. You build a report, and nothing changes.

That’s your signal.

If no one is reacting to your work, stop and question it.
What happens if you don’t do it?
Does anything break?
Does anyone notice?

If the answer is no, you’re not doing meaningful work. You’re doing comfortable work.

I’ve been there. I used to build out board decks for staffing updates. If I was lucky, I’d get through a few slides. Truth is, no one really cared about the deck. They just wanted to know I was on top of things.

What the process did give me was clarity. It forced me to know my numbers, know my gaps, and know my story. But the format? Probably not the best way to get there.

There’s almost always a better way…you just have to be willing to find it.

And here’s the part most people overlook:

We sit all day. We think all day. We stare at screens all day. Then we wonder why we feel off, stuck, or burned out.

You don’t fix that with another “mental health day.”
You fix it by moving.

Go mountain biking.
Go for a run.
Do push-ups.
Do hard, outdoor, hands-on work, yard work and get your hands dirty, farm-type work, anything that gets you out of your head and into your body.

There’s something about real physical effort that resets you. It clears your mind, sharpens your thinking, and makes the work that actually matters feel a lot more obvious.

So if you take anything from this, let it be simple:

Do something uncomfortable every day.
But make sure it actually matters.

That’s the work.

The other day I interviewed a candidate who opened with questions about the job title and pay before they could even tell me why they were qualified for the role. The vibe was, “You’ve seen my LinkedIn, so you already know I’m an A‑player.”

That’s like giving yourself the nickname “Bad Ass” before you’ve actually done anything bad ass.

A lot of candidates walk into interviews convinced they can do the job OR that they’re even better than the job. That’s okay and it might be true. But you still have to show it before you start pushing for a bigger title and more money. First, get the company or at least the recruiter to actually like you, trust you, and see the fit.

You might be great. Just don’t lead with “I’m great.” Lead with proof. Stories, results, examples. Then ask for flexibility.

In this case, the hiring manager actually is open on title. But there’s a right time to go there: after you’ve shown you can do the work, after you’ve built some trust, and after you can tell they want to move you forward…but not in the first two minutes of the call.

This past week while on vacation in Cabo, I kept hearing the same thing from locals: “You’ve got to go to Chileno Beach.” Fewer tourists, more locals, great water. One problem: the parking lot is chaos.

The first day, we circled forever. We’d watch people pack up, then race a line of cars for the same spot. After a while, we gave up and went to a different beach. Annoying, but interesting to watch how people handled a scarce resource.

The second time, we changed one thing: we went earlier. Same lot, same demand, different timing. Within seconds, we grabbed a prime spot at the front.

That’s hiring.

The parking lot is the job market. The spots are roles. The cars are candidates. Companies “open spots” when they’re ready to hire. Candidates start circling when they’re ready for a move. Your outcome has a lot less to do with how deserving you are and a lot more to do with timing, fit, and how you show up.

If you’re searching right now, it might feel like day one at Chileno: you circle, you try, you leave empty‑handed. That doesn’t mean there’s no space for you. It might mean you need to adjust your timing, your approach, or your expectations.

A few practical takeaways:

• Show up earlier: start your search before you’re miserable or unemployed.

• Be ready: dial in your resume, LinkedIn, and story so you can move fast when a spot opens.

• Stay flexible: sometimes you take a “good enough” role as a temporary spot while you wait for a better one.

For hiring managers and recruiters, the same rules apply. Most of the people you want already have a spot. Your job isn’t to yank every parked car out of their space. Your job is to find the ones already in motion—or quietly thinking about moving—and help them make a clear decision.

Finding parking in a crowded lot and landing a job in a crowded market feel the same from the driver’s seat: slow and competitive. But with better timing, sharper prep, and a little patience, you usually end up exactly where you need to be.

It’s okay to be bored.

That’s where creation actually starts. Not when you’re busy. Not when you’re reacting. When it’s quiet… and there’s nothing but your own thoughts.

From that blank space, something begins to form. An idea. A plan. A direction. Most of it won’t be great but that’s not the point. The point is you made something out of nothing.

If you can learn to think, write, and speak clearly, you can create. And once you create, you have a choice: act on it… or ignore it.

Acting on your own ideas, even imperfect ones, is almost always better than blindly executing someone else’s.

I spent years inside big companies like, PepsiCo, Honeywell, and Energizer Holdings. Big companies are where direction often came packaged as “strategy,” but felt disconnected from reality.

Some of it made sense. A lot of it didn’t.

It was polished. Approved. Safe. And often… useless.

We’d sit through annual compliance trainings, check the box, move on. Did it improve behavior? Maybe. But it definitely created the illusion of progress without actually building anything meaningful.

That’s the trap…confusing activity with creation.

Real creation is harder. It’s uncomfortable. It requires you to sit in that quiet, slightly restless place and do something with it.

Most people avoid boredom. They reach for their phone, a meeting, noise, food, or a drink. Almost anything to escape boredom.

But boredom isn’t the enemy. It’s the starting line.

A lot of what we enjoy today - products, companies, ideas - came from someone who had the space to think… and the willingness to follow that thought all the way through.

So instead of trying to eliminate boredom, get better at it.

Sit with it. Think. Write. Build.

Then go do something with what shows up.

The other day, a hiring executive told us something simple:

“Just send the top candidates. We’ll interview them.”

No request for a stack of resumes.

No fishing expedition.

No “let’s see 15 and narrow it down.”

Just: bring me the ones that matter.

It stood out.

Because a lot of hiring leaders do the opposite—they want volume. More resumes. More options. More noise.

But this was different.

This was trust.

They’re paying for a service. They expect us to understand the role, filter hard, and deliver people who are actually ready.

Simple idea. Not easy to execute.

But it’s how it should be.

There’s a bigger lesson here.

In any job—recruiting, sales, leadership, anything—people are either trusting you to do the work… or they’re not.

If they’re not:

• You haven’t earned it yet

• Or they don’t know how to let go

Either way, something’s off.

The goal isn’t to send more.

The goal is to be trusted to send less.

Do your job.

Prepare relentlessly.

Know what great actually looks like.

Deliver work that doesn’t need to be double-checked.

Then do it again.

And when someone trusts you enough to step back and say,

“Just bring me the best…”

Don’t take that lightly.

They didn’t make your job easier.

They made your standard higher.

The one thing that will immediately improve your chances of landing a job or closing a deal?

Preparation. Focus. That’s it.

And yet… it’s shocking how often people skip it.

I’m constantly surprised by how many candidates I speak with who’ve done little to no research on the company. Not even the basics. You can feel it within the first 60 seconds.

I was reminded of this again recently while working on a senior technical role. Candidate after candidate started interviews without really knowing what the company did, who they served, or why the role even existed.

It puts you on your heels instantly.

Instead of building momentum, you spend the first five minutes playing catch-up—covering things that could’ve been handled with 10 minutes of prep.

Not a great way to start.

Then every once in a while, you get someone who gets it.

I spoke with a candidate recently who had gone deeper—looked at the company’s investors, understood the business model, and came in with thoughtful ideas on how they’d help the company grow.

Completely different conversation.

More engaging. More strategic. More impressive.

That’s the person who stands out.

Here’s the reality:

There’s no excuse anymore.

You’ve got unlimited access to information. You’ve got AI tools that can break down a company, prep you for interviews, and help you think through smart questions in minutes.

You don’t need to chase down a busy friend for advice.

You just need to care enough to prepare.

At the end of the day, this isn’t complicated.

The candidates who prepare win more.

The ones who don’t… keep wondering why they’re not getting offers.

Your move.