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How the hiring process is like dating

Parallels to first dates, social media stalking, making it official, and more PLUS one new Chief of Staff req @ a CPG startup that we're working on (check our job board for an EA role, too!)


But First, 3 Shower Thoughts:

  1. There’s nothing like being sick for a whole week to remind you about what matters most in life — your health!

  2. Football season isn’t long enough. Give the people what they want.

  3. “I want to be a recruiter when I grow up”, said no one ever, but I really love what I do 😍


Finding The One...

The hiring process is kind of insane if you think about it — in most cases, employers and candidates are making decisions based on just a couple of hours of hang-time with each other.

You meet, you chat, you try to figure out if there’s a future together. Sometimes you both hear what you’re hoping to hear and things start looking pretty rosy. You wonder, could this be it? Could this person/job/employer be THE ONE?

Positively thrilling, but also daunting. Just like dating…which is fun, right? Right? sweats in Bumble swipes

Here’s what the hiring-is-like-dating breakdown looks like:

Finding Matches

Finding candidates or potential dates falls under the “active search” and “profile review & screening” steps of the dating and hiring process.

When employers look for potential candidates, they’re considering applicants to job postings, referrals from their network (up to 45% are internal hires), or they’re using a recruiter.

When a company has very specific requirements for a candidate, such as…

  • Specific skills (A, B, and C)

  • Unique skill mix (A, B, C, plus a little bit of X and Z which are unrelated)

  • Being nearby (see: not remote)

  • Certifications/degrees, etc.

  • On board with a below market salary or other things that could be disqualifiers on paper

…then in many cases they’ll use a recruiter. Otherwise, the hit rate of waiting for someone with these specific skills and experience to come their way is very low, if not zero.

IRL, this is equivalent to you going to a bar, seeing someone who meets your criteria, e.g. is attractive, seems personable and outgoing from far away, is surrounded by friends, etc., and approaching them yourself, or recruiting your friend to go over there and pitch them on why you’re so great :)

Online, this looks like swiping right on profiles for people who meet your specific qualities, interests, and personal values.

So, whether an employer is looking for candidates or someone is looking for dates, there is an active search followed by a profile review and initial screen:

The First Date / Nailing the Interview

Assuming things go well at the screening stage and you both decide to move forward, it’s time to set up the first date (the first interview!).

The best first dates are full of laughter, good/deep conversation over shared interests, and perhaps the most important thing: that spark ✨. In a similar way, I think a promising job interview can leave both people really excited about what’s to come, too. If the employer and candidate very obviously check all the boxes for each other as they start learning more, then it ends up being a slam dunk. Things actually are as they appeared, if not better than initially thought.

If the date is going really well, usually nobody wants it to end. And if schedules actually permit it, a really good sign of your interviewer being very interested in you as a candidate is going over their scheduled time with you. A 20-minute call turns into a 45-minute call. 60 minutes turns into 90 minutes.

Conversely, if you’re scheduled for 30 minutes and it only goes for 15-20, or they ask if you have any questions very early in the interview, it means that they’ve already made a decision that it’s not a fit and they’re trying to wrap up quickly, mainly because they don’t know how to break the news to your face or want to avoid having that conversation live for some other reason.

But if it’s going really well, then you’d be pumped to learn about the next step in the interview process while you’re still in front of each other, AKA, scheduling the second date!

Now this part is going to sound really crazy, but stick with me…

If someone is very, very interested in you, they will not dilly dally about a second meetup. If both people are excited about each other, and whether you are the pursued or the pursuer, you’re not going to get turned off by meaningful action, e.g. pitching a second date or responding quickly to confirm availability.

Responsiveness in general shows true intent and interest. And let’s not even get into the mind games of “playing hard to get” because life is truly too short (if you really thought you found the love of your life, then you’re gambling when you shouldn’t even be near the casino).

True story: I spoke to a founder once who wanted to wait to schedule a candidate they were really keen on to build up tension and I literally said to him, “Dude…no!!” 😂

Because guess what? True love and top talent wait for no one, so while you think you’re playing the game, the game is playing you and someone else is courting your person. Hesitating might mean that you lose out to someone more decisive, especially when you know they’re actively seeing other people/on the market.

And finally, for the love of God, please stop ghosting after interviews/first dates. Just as you'd appreciate a message back after a date, even if it's to say there wasn't a spark, candidates deserve a response. Don't leave people hanging! It’s bad juju.

Subsequent dates + social media stalking

If you have a really strong screening process, your subsequent dates/interviews tend to be more confirmatory than anything else. An employer is still evaluating if it’s a fit, but likely less so regarding factors that are on paper (e.g. resumes, profiles), barring any case studies or work trials. Rather, it’s more about culture fit or a vibe check:

Confirmatory: “Ok, this person actually is who they say they are.” / “Wow, I’m even more excited about them.”

Vibe check: “I can see this person working here or working for me” / “I can see myself getting serious about or marrying this person”

If all goes well in subsequent interviews, usually candidates get to the reference check stage (or references are being checked along the way). This helps answer the question, “what do other people who were very close to this person think about them?” A confirmatory step in its own right, references are also an opportunity to dig a bit more — what might be a questionable red flag or is the opposite of what I’d expect to hear/learn?

The equivalent to this in dating is social media stalking or asking for the download on the person from mutual friends. Ideally, you’re looking for glowing reviews and if you come across anything negative, it ends up being irrelevant or inconsequential. (PS — I mean stalking here in the lightest, most innocent sense, e.g. browsing someone’s profile to peep their sense of style if that’s important to you 👀, not actual cyberstalking, which is criminal).

When you’re pages deep on your date’s Instagram and accidentally like their Cabo pic from 10 years ago.

Browsing their Instagram or Twitter will likely give you a sense of your date’s social circle, personal interests, and how they interact with the people around them.

Red flags at the reference check or social media stalking stage include:

  • Dishonesty, inconsistencies, or disrespectful behavior

  • Other incompatible or dissonant behavior, e.g. person says they’re reliable but references say otherwise

  • Negative attitude

  • Speaking poorly about exes or past employers (!) There are always ways to frame things positively. Be thoughtful about how you talk about others, even if the situation was less than stellar.

Making it offish: The Offer

Assuming everything checks out, you’ve made it! It’s time to commit and make it official. And timing here is everything, too. Everyone wants the real-deal official “boyfriend/girlfriend” title (read: an irresistible offer), and employers want their #1 candidate.

And they will pull out all the stops if necessary. Job was scoped at $200k but they really want the more senior candidate? Here’s $300k because we don’t want to get into a bidding war. You’re more motivated by equity? Let’s break down what your potential upside looks like and how you can help us build the equity incentive plan for the company. Want to hit a specific cash comp number you had in mind? Let’s get creative about base + bonus and how you can hit that target. All true stories from some of our placements.

How a candidate and company negotiate during the offer stage is also very revealing and can strengthen the mutual commitment and excitement to seal the deal. Making it official by dropping the B or G word does the same.

But things can also fizzle out at this stage, the biggest factor being timing in my opinion. I’m very happily betrothed to Scott Britton , and I’ve been out of the game for a while, but my rule of thumb when I used to be single was this:

If I’m seeing you for 3 weeks and you don’t make it official by then, it’s time for me to move on. Might sound like an arbitrary rule but it helps weed out time-wasters and yes, f-boys.(PS: come to this substack for career advice, stay for the dating advice?!).

I digress ✋. If you’re in multiple processes as a candidate and an amazing offer comes your way, be transparent with your other suitors. If you’re really interested in one of them, then tell them that. Share that you received an offer but are really keen on continuing the conversation and that you want to make it official with them. We’ve placed plenty of candidates who received other offers before our clients could wrap their interview process.

To bring this back to dating, imagine if someone said this to you:

“It’s been amazing getting to know you and I’m pretty sure I’m obsessed with you (lulz), but what I’m really looking for is commitment with someone I can see myself being with long-term. I’d love for that person to be you, but I need to consider other people if this isn’t aligning for you. How do you feel about this?”

You spoke your truth, laid it all out, and put the ball in their court. If they really want you, but for some reason fumbled at this stage, they will scramble to re-engage ASAP. If not, they’ll hopefully share their feelings, too, and you can leave things on a high note.

At the same time, maybe the company that’s dragging their feet, who might be uncertain about you, or who has otherwise cooled their once hot & heavy pursuit isn’t a good fit anymore. Set boundaries and do what’s right for you.

Breaking up: Rejection and moving on

Not every date leads to a long-term relationship, and not every interview leads to a hire. Rejection is part of the process. But I’m a big believer that each "no" you hear is a step closer to the right "yes”. They’re part of the dots that make up your experience.

You can't connect the dots looking forward; you can only connect them looking backwards. So, you have to trust that the dots will somehow connect in your future."-Steve Jobs

And even if you get in a relationship or take that job that ultimately doesn’t work out, or even ends up being a harrowing ordeal, it’s still part of your blueprint and the grander plan to lead you in the direction that you’re meant to journey — to land at the right company, in the right job, doing purposeful and fulfilling work, or to be with the person you’re meant to build your life with.

When we reframe things from “Why is this happening to me?” to “Why is this happening FOR me?”, we lighten up and become more open to opportunities and actually make space for them to come into our lives. So if something doesn’t go your way today, don’t lose faith. Because tomorrow might present a whole different journey or opportunity to explore. 🙏

Search Spotlight

Chief of Staff @ CPG Startup

Our client is a CPG startup at the leading edge of developing products designed to enhance everyday life. Powered by a deep love for science, they are pioneers in creating direct-to-consumer products that set a precedent in product quality, safety, and transparency.

Role Summary:

The Chief of Staff will play a critical role helping to drive the company's strategic direction and operational effectiveness. This position blends the roles of Chief of Staff, business development strategist, entrepreneur, and analyst, offering an unparalleled opportunity for professional growth and impact. The successful candidate will excel in a high-velocity environment, spearheading initiatives that foster cross-functional collaboration and business development while championing innovation and efficiency across the organization.

Key Responsibilities:

  • Facilitate optimal information flow throughout the organization, ensuring all teams are aligned with strategic objectives and key insights from executive meetings are disseminated and acted upon effectively.

  • Represent the executive team's vision and priorities, enhancing internal and external communications and operationalizing the company's strategic goals.

  • Lead business development activities, managing inbound opportunities, prospecting new ventures, and launching partnerships.

  • Improve operational processes, identifying and implementing enhancements to drive efficiency, alignment, and effectiveness across various departments.

  • Embrace ownership of diverse initiatives, ranging from content creation to systems implementation, contributing to the company's growth and innovation ethos.


  • Management consulting and/or VC, PE, or investment banking experience with experience at a consumer startup

  • Outstanding strategic thinking and execution skills, capable of leading projects with minimal guidance and making impactful decisions based on incomplete information.

What They Offer:

  • Competitive salary + equity and a comprehensive benefits package, including health/dental coverage, 401(k) matching, unlimited PTO, L&D stipend, and more

If you're interested and want to learn more about the company, just apply here! I’ll get back to you ASAP if your experience aligns with what they’re looking for.

Know someone who could be a fit for this role? Feel free to share this blog post!

Check out our job board for the full list of opportunities with our clients!

Job Opps

🍴Chief of Staff @ Boqueria - bringing Spanish flavors to life

My thoughts: I love love love Boqueria — it’s an awesome tapas restaurant in NYC. BUT, this role is 100% an executive assistant role!

When I see verbs like “compile, assist, handle, arrange” it is pointing to an admin-heavy role. There is nothing wrong with that, I just think this role is mis-titled and they’re looking for a very senior executive assistant.

That being said, I don’t know a single person who has the following preferred experience and is also looking for $80-120k/year:

  • Experience working in the restaurant or food and beverage industry. (my guess is 1-2 years is needed to qualify?)

  • Experience preparing Board, investor, and other critical presentations. (you definitely need more than at least 3-5 years of total experience to be preparing board decks? If fewer, then you command a higher salary given your career slope)

  • Experience coordinating interdepartmental planning processes (this sounds like something that someone further along in their career would do, for example 5+ YoE).

So, I’m a bit lost. I think it’s super important to have multiple people gut check a JD before posting it to make sure that holistically it all ties and you can actually find this person at the salary range you’ve set. Otherwise you’re spinning wheels.

💰 Salary: $80K – $120K/year

📍 This role is in NYC.

📥 Apply here.

🔧 Engineering Chief of Staff @ CIRCOR – flow control products

My thoughts: I rarely see engineering CoS roles so I had to highlight this one! CIRCOR is a world leader in the development‚ engineering‚ manufacturing‚ distribution‚ service and support of fluid handling systems. Their flow control products play a crucial role in industries like oil & gas, power generation, and aerospace & defense.

As the Engineering Chief of Staff, you’ll be the Chief Engineer’s right-hand person, diving into everything from new product design to making sure their factories are humming along.

Ideal candidates will have:

  • A Bachelor’s degree in Engineering (Mechanical, Aerospace, Civil, Electrical), with bonus points for a Master’s or MBA.

  • Over a 10+ years of engineering experience, with at least 5 years dedicated to the kind of engineered products that help planes fly and machines do their heavy lifting (hydraulic and electro-mechanical devices are your jam).

  • Superb skills in steering projects, crunching data, and making decisions that count.

📍 This role is in Tampa, FL.

📥 Apply here. 

💼 Chief of Staff to Head of Product Work Management @ Atlassian - team collaboration software

My thoughts: This is a unique role given the Chief of Staff’s principal is the Work Management for All (WM4A) product leader and not a C-level executive, but it doesn’t mean the role is junior by any stretch!

They’re looking for an exceptional Chief of Staff to provide strategic support, help them optimize processes, and drive cross-functional coordination.

Ideal candidates will have experience with:

  • Strategic problem-solving and execution: Convert high-level strategies into actionable plans

  • Communication and engagement: Adjust their communication to meet the diverse needs of various audiences, enhance engagement, and effectively address team dynamics.

  • Data-informed decision making: Support decision-making processes with data, simplifying complex analyses for different stakeholders to ensure a data-driven approach.

  • Leadership and team development: Constantly connect people and ideas, and strengthens the team's performance and cohesion.

💰 They’re offering 3 salary bands based on geographic zones in the US (here’s a link to learn more)

Zone A: $231,500 - $308,600

Zone B: $208,300 - $277,800

Zone C: $192,100 - $256,200),

📍 This role is remote if you so choose! 

📥 Apply here.

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