Two Things You Should Share With A Recruiter About Your Past Positions

You’re 5 minutes into a phone interview.

In spite of the obscene amount of coffee you drank this morning, your jitters are starting to subside. You’ve totally got this!

So far you’ve caught the recruiter’s attention, you’ve given them an executive summary of your professional experience, and you’re just starting to delve into your background — backwards, of course.


But now what? What do you actually say about each position on your resume? There are so many things you could say and so little time…ahh, decisions, decisions.

Only you can decide what to say about each position you’ve held. What you say will probably (read: should) vary based on the job you’re interviewing for, but there are two critical topics that you won’t want to leave out as you talk about each of your past positions.

chess pieces king and queen

Content is king but context is queen

What you say about your professional background matters in a phone interview, to state the obvious. But the context you give me about each position and the companies you’ve worked at matters a whole heck of a lot, too. Without it, I have no idea how to interpret what you tell me. And my interpretation will probably be wrong because, let’s be honest, there’s a 0.00001% chance that I’m deeply familiar with each of the companies you’ve worked at.

Let’s take a simple example.

One fundamental thing I want to figure out is whether or not you’re a good match for the seniority of the position I’m hiring for. And I don’t mean how many years you’ve been working. Seniority is a lot more nuanced than that. I want to know things like:

Who do you report to?

How much experience do you have working with C-suite executives?

Who reports to you, if anyone?

How big is your team, if you have one?

What is the scope of your / your team’s responsibilities?

So, once again, spoon feed me. Prevent me from thinking too much. Don’t let me draw my own conclusions. Give me the context I need to interpret the information you give me about the places you’ve worked and the positions you’ve held.

(As an aside — context is the same principle at work behind my resume advice to include a company description on your resume. )

What would you say…you do here?

Have you ever wondered what a friend or even a colleague actually does all day? Sure, you know they stare at a computer screen and send a lot of emails and probably go to some meetings. But what do they actually do.

You’re not the only one. I wonder this all day, every day about every person I interview.

And Tom’s answer from Office Space probably won’t get you very far —

“I deal with the goddamn customers so the engineers don’t have to. I have people skills! I am good at dealing with people. Can’t you understand that?!”

I’m constantly amazed how many people I speak to and, even after a 5-10 minute conversation, I still have no idea what they’re good at or how they pass the hours between 9 and 5. That’s bad news. At some point, if I can’t figure out what you do, I’ll assume that you’re not a doer at all. You’re a delegator. And a delegator is the last thing I want in a start up where everyone needs to get their hands dirty.

So, after you give me a summary of your professional experience and a little context about your role, be sure to tell me what you actually do on a daily or weekly basis.

And there you have it! The next time you’re describing your background to a recruiter, be sure to include plenty of context about past positions and don’t forget to make it clear what you actually do all day long.

The Distracted Goldfish



5 Reasons Why You Shouldn’t Describe Your Job Experience Chronologically

You’ve done it.

Your resume passed the test. A recruiter wants to schedule a phone interview to learn more about you. You’re one step closer to your dream job. Hooray!

Take a moment to celebrate. But don’t break out the bubbly quite yet. Patience, young grasshopper.

There’s a lot to think about when preparing for your first conversation with a company. It can be downright overwhelming! Research the organization, identify good questions to ask, brainstorm relevant stories from your past experience, think about how you want to present yourself… Where to even begin?!

The first step you should take is to figure out your answer to the question, “walk me through your resume” because there’s a 99.9% chance you’ll get a question along those lines.

As I’ve already mentioned, when you talk a recruiter through your past experience, you’ll want to assume they’ve never seen your resume before, do something to catch their attention right away, and start with an executive summary.

But there’s something else you can do to stand out even more, to go against the grain just a little bit.

A group of goldfish swimming with one swimming the wrong way

Begin With The End In Mind: Work Backwards

I love The Sound of Music. It was a staple of my childhood. But when Julie Andrews said, “let’s start at the very beginning,” she had it all wrong.

One of the worst phone interviews I’ve ever experienced started with the candidate saying, “I graduated from Rice University where I majored in Economics and Business.”

Ok, not inherently terrible…

But then the candidate proceeded to describe every single position she had held throughout her 15 year career — in detail and in chronological order — for twelve minutes out of a 20 minute phone interview. I had specifically asked for a brief, 2-3 minute description of her background. And I had explicitly mentioned that the interview would only be 20 minutes. I lost track of the number of times she said, “and then….and then….and then.”

Snoozer city.

By minute #4, my eyes had glazed over. She was still talking about experiences from 10+ years ago.

By minute #5, it was clear she hadn’t listened to my request for a 2-3 minute description.

And by minute #7, to be brutally honest, I wasn’t paying attention anymore.

Sure, I could have cut her off, but I learned a lot about her communication style, her inability to read others, and her (lack of) listening skills by letting her continue to talk.

Yes, she went into my reject pile. Did you really have to ask?

To avoid falling into this trap, don’t describe your prior job experience chronologically. Instead, begin with the present day and work backwards from there.

Why? Here are five interrelated reasons.

1. Relevancy

Your most recent job is almost certainly what’s most relevant to the position you’re interviewing for. This is the experience that matters most to me as your hiring manager, so please start here.

And if your current role isn’t what’s most relevant, start somewhere else.

2. Catch (and keep) my attention

As I’ve mentioned elsewhere on this blog, I’m highly distractible.

The more relevant I find the first few things out of your mouth, the more likely you are to hook me. Making a positive impression quickly is the only way to catch my interest and attention. And that is critical to get to the next round of interviews.

3. Spend time on what’s most relevant

If you’re like 99% of other human beings, you’ll go into the most detail about the first position or two that you mention when you describe your experience. It’s only natural.

This is a problem when you describe your background chronologically because then you’re spending the most time on the things you did the longest ago. No bueno.

4. Stay flexible – and speed up

Starting with what’s most relevant gives you flexibility.

I don’t want more than a 3-5 minute description of your background. (Admittedly this varies between hiring managers). If I have specific questions, I’ll ask you to elaborate.

Telling me first about your most recent position makes sure you can stay within whatever time constraints a recruiter sets and still convey the important information. You then have flexibility to speed up or to go into less detail with every subsequent position you describe.

Consider checking in with your recruiter explicitly as you go. Ask questions like, “Is this too much detail?” or “Do you want me to elaborate more?” That way, you can adapt to what they want on the fly.

5. Stand out from the crowd

95% of job candidates describe their past experience chronologically.

Simply starting from the present day and working backwards will set you apart, which makes you memorable. And that is always a good thing to improve your chance of getting to the next interview.

Or, if you really want to break the mold, don’t take a job-based approach to the description of your background. Instead, talk about your experience thematically. Woah! You rule breaker, you.

The Distracted Goldfish



What hiring managers look for when they ask about your background — and what you should say first

The world’s most common — and seemingly most innocuous — job interview question is the one that asks you to describe your background.

I know, I know. It’s your least favorite question as a candidate.

“Ugh really?” you’re thinking, “Can’t you just look at my resume? I spent hours on it! Asking me to tell you about my background is a total throwaway question. It’s a waste of precious interview time.”

But is it really?

Not in the slightest. If you want to nail your interview, preparing the perfect description of your background will take some serious time and thought. In fact, if you only have time to prepare one thing before an interview, it should be your answer to this question. It sets the stage for the rest of the interview.

As you start to think about your answer to “Walk me through your background,” first assume the hiring manager knows absolutely nothing about you. Never ever start by saying, “Well, you’ve seen my resume, so I’ll keep this brief.”

Second, make sure you hook the hiring manager’s attention right off the bat to make sure he or she is giving you their full attention.

goldfish in a bowl with a hook

What does a hiring manager look for when you describe your past experience?

Why do hiring managers ask candidates to describe their backgrounds, anyway?

They might be lazy.

(Why look at a resume when I can ask the candidate?)

They might be insanely busy.

(No time to review this resume!)

They might be distracted.

(What resume?)

Or they might be all of those things.

But there’s actually a lot a hiring manager can learn from your answer to “Can you walk me through your experience?”

Personally, I look for two things.


Communication style

Excellent communication will be critical for us to work together productively in a fast-paced startup where there isn’t time to spell everything out in detail.

I want to know that you’re a structured communicator — that you organize your thoughts into a framework or logical sequence. This could mean starting with a high level summary to frame the conversation before sharing detail. I shouldn’t wonder where you’re going.

Similarly, please get to the point quickly and share only what’s important. I’m detail oriented but, if you’re joining my team, I don’t want to worry about all the details. So, be succinct without leaving out essential information. It’s a tricky balance!

If you can’t communicate your own background clearly and in a compelling way, that’s a big red flag for me. After all, you lived it.

Skills and areas of expertise

The other checkbox I’m looking to tick off as you describe your background is “fit.” Are your skills and past experience a good match for the role and company?

Take this opportunity to use buzzwords and keywords relevant to both your background and the role; show that you’re a good fit. But don’t be too obvious about it.

When I was interviewing to fill a marketing operations role, for example, I wanted to hear candidates reference specific technologies and tools, metrics, data cleanliness, and process.

Hopefully I’ve convinced you that nailing the description of your experience is critical. So where do you start?

start blocks.jpg

Start with an executive summary

One candidate I spoke with recently started her answer with, “I graduated from Rice University in 2008 with a degree in economics” and I knew immediately that the conversation was doomed.

Don’t start at the beginning. Instead, start with an summary of your background and experience. Tell me the highlights.

What are you an expert in?

What themes tie your background together?

What do you want me take away or learn about you?

Do you have a core philosophy that governs how you work in your role?

Starting with a summary gives me the conclusion first. It’s a huge opportunity because you can significantly influence the hiring manager’s perception of you. And the more you can tailor your answer to the specific role and company, the better.


Here’s what I mean:

“I have 10 years of experience in marketing, most of which has been building compelling brands for mid-sized tech companies. In the early days of my career, I was in the trenches and created a lot of content and visual brand assets. Now I have a team of people who do those things and I focus mostly on content and brand strategy.”

This is awesome. It tells me your area of expertise, the kind of companies you’ve worked at (which is important for context), and prevents me from doing math.

“My background has been entirely in start ups, anywhere from four employees to 250 employees. I’ve worked in a variety of functional areas from marketing and sales to product and operations. So, I’m an operational generalist and mostly an expert in learning new things and getting things done.”

This also works well — at least as a starting point. Again, it gives me context and a sense for what you’ve done in the past at a high level as well as what you think you’re good at.

“I’m extremely passionate about making things work better. For me, it’s all about people, process, and tools — in that order. Making sure that I have the right people on board and then improving processes creates the first layer of efficiency. And then leveraging automation tools takes that efficiency to the next level. Oh, and I always measure my success quantitatively with metrics.”

What I like about this description is that it tells me a little bit about how you operate — your core philosophy for how you approach work. It doesn’t tell me your core expertise, but that might be OK if you highlight various skills as you dig into the details of your background.

There’s no one right answer for how best to describe your past experience or background to a recruiter or hiring manager. But, start with a summary to provide a framework before you slot in everything else. After all, you can’t build a home without a solid foundation.

The Distracted Goldfish



How to catch a recruiter’s attention right off the bat in a job interview

[Or, alternatively: What oysters, popcorn, and mothers-in-law have to do with your next job interview]

I know candidates think they have it rough. And they do; being interviewed is exhausting and requires a significant investment of time and energy. But interviewing candidates is exhausting too. During hiring sprints, I’m sometimes on the phone for hours at a time, struggling to keep my phone charged and talking to a new candidate every 20 minutes. It’s back-to-back without a moment to catch my breath or get a drink (which is perhaps a blessing since there’s no time to pee, either).

One Friday afternoon several months ago was no different. It was the end of a long week and while the potential for weekend sunshine had me excited, my afternoon had been filled with a number of phone screens already, including a few doozies. *Yawn.*

I took a deep breath and dialed my next candidate. Enter Mike.

“Hey Mike, it’s Sydney calling from XYZ Enterprises. How are you?”

“I’m excellent!” he replied with a level of enthusiasm only appropriate for a Friday afternoon, “I’m going to eat oysters with my future mother-in-law in a little bit!!”


Insert cartoon-style blinking on my part. Huh, what? I had fully expected the canned response I get from the vast majority of candidates — a simple “good, thank you” or maybe “fine, thank you, and you?” if I’m lucky.

Shaking myself awake I replied, “Oh really? Well that sounds like a lot of fun! Or I guess that depends on how you feel about your future mother-in-law. I know sometimes that can be a controversial topic. Where are you headed?”

And so the conversation continued for a minute or two with small talk of oysters (Hog Island? Have you been to Tomales Bay to shuck your own?) and mother-in-laws (You get along swimmingly with yours? That’s awesome, me too!), the latter being admittedly dangerous territory.

Mike’s response to my standard “how are you?” greeting was totally off-the-wall but also disarming because it gently broke interview social norms. It caught my attention and gave him an opening to talk about something other than the weather which in turn allowed him to build rapport. Importantly, Mike’s response also fit him to-a-T; it was authentic to his slightly wacky personality in a way that immediately gave me insight into his character. I was ready — even excited — for the rest of our 20 minute conversation.

You only have seconds to make a first impression

Exchanging pleasantries and summarizing your experience are likely the first two things you’ll do in an interview, which means those are your only moments to make a first impression. There’s debate about how long it takes to form a first impression, but it’s on the order of seconds, not minutes.

When you do or say something out of the ordinary right off the bat like Mike did, it’s a breath of fresh air for your hiring manager. I’m not talking about anything outrageous, just enough to hook and reel me in. After all, there are social norms to uphold and you don’t know my sense of humor. [Note: Be very careful using edgy humor. More on that at a later date.]

So take it seriously! You need to be stellar — at your absolute best — when you first answer the phone and talk through your prior work experience in an interview.

Let’s say that you only have 30 seconds to catch my attention before my mind starts to wander and I get distracted by a YouTube video of cats eating ice cream that a friend just sent me. Do you have a plan to stand out from the crowd?

black sheep goldfish stand out

Say something to stand out and hook your interviewer in the first 30 seconds.


Here are three simple behaviors that reel me in as I’m engaging in small talk with a candidate and when they start to describe their background.

1. You’re incredibly articulate

Do you leave your friends and family speechless when you’re debating politics or other intricate, heated topics? Do colleagues fawn over your presentation skills and immediately agree with each one of your persuasive points? Lucky you!

The silver tongued are naturally engaging to listen to. If this is you, you don’t have to do too much out of the ordinary to impress me. Simply exchange pleasantries and talk about your background as you normally would, making sure you follow the other best practices on this blog, of course.

Not you? No worries. Most people aren’t extraordinarily eloquent, including yours truly. I can put together sentences that include both subjects and verbs but that’s where my power of persuasion ends. The good news is that this isn’t the only way to catch my attention.

2. You’re SUPER energetic, friendly, and engaging to talk to

Can you develop rapport with a brick wall? Do near strangers share their life stories with you? Well then, put that skill to use and work it!

When your interviewer asks, “how are you doing?”, set yourself a part. Don’t just say “great, thank you” or “fine, how about you?” Instead, give the hiring manager a more interesting response like Mike did. Show interest in what the hiring manager is saying. Ask them a question about themselves. Offer up information about yourself. Quickly find something in common that allows you to connect. And yes, that can be something as random as oysters or mothers-in-law.

Whatever you do, don’t hide your energetic, relationship-building personality behind a layer of formality. Most candidates are far too formal in interviews. I want to hire a human with emotion and personality, not an overly serious robot. Be professional, but let your personality shine through too.

And remember to use your best “phone voice.” It’s hard to develop rapport without seeing the person you’re taking to, so you have to overdo variation in your vocal intonation a wee bit. Monotone is, well, monotonous.

Hard to imagine yourself being over-the-top enthusiastic? That’s ok. Give it a try anyway. Cocktail hour small talk isn’t my strong suit either, but everyone can learn to engage in a few minutes of superfluous chitchat.

3. You share an interesting tidbit about yourself 

Not incredibly articulate or super energetic? The good news is that everyone can share an interesting, unusual, or impressive tidbit about themselves in the first minute of small talk or when starting to describe their background.

I once had a woman launch into the summary of her background by talking about popcorn, specifically how she would be popcorn if she were a snack food. It was a little cheesy (no pun intended) and I did momentarily wonder “where on earth is this going…” but it caught my attention and provided her a foil to quickly share important attributes about herself. Most importantly for a start up hiring manager: she thrives under pressure. Even though it was a bit contrived, her story drew me into the conversation and made her incredibly memorable.


As you think about what hook to use in your next interview, remember to be authentically YOU! Your hiring manager wants to understand who you are as a person. And don’t worry too much if you aren’t naturally super articulate or overly energetic, like I mentioned above. I realize that my draw to candidates based on these attributes is superficial and won’t get anyone through an entire interview process. But it sure helps to grease the wheels a bit.

Are you a recruiter? What catches your attention?

Are you a candidate? What “hacks” do you use to catch someone’s attention?

The Distracted Goldfish



How to summarize your background in a job interview, tip #1

If you’re in the midst of job interviews, you already know that the most common interview question you’ll get is some variation on “walk me through your resume.”

Maybe it’s “please summarize your experience for me,” or “tell me a little bit about yourself,” or “explain your background for me.” But it’s all getting at the same thing.

walk me through your resume

“Why, of course!” you say.

“Easy!” you think.

I mean, you lived it, right?

Not so fast, career dreamer.

This seemingly innocent question is also one of the hardest to get right. Potholes, quick sand, and cliffs all await you as you verbally re-live your background or tell your interviewer “a little bit about yourself.” It’s a proper Tough Mudder obstacle course but without the mud slinging and trophies.

obstacle course


Assume your interviewer has never seen your resume, cover letter, or LinkedIn profile

Summarizing your background can’t be that important if the hiring manager already has your resume, right?

Nope. Wrong.

“But…but…” I hear you say. “C’mon, hiring manager! Stop being lazy. You have my resume and I worked on it for approximately a billion hours so just read it and you’ll know everything you need to know.”

I’m with you. As an interviewee, I hate being asked to summarize my background. But the “just read my darn resume” attitude also once got me turned down from a job I really wanted. More on that another time perhaps.

So, now that I’ve been on the other side, I’ll let you in on a secret. Your interviewer isn’t lazy. They’re just really really REALLY busy. And distracted.

Let’s be honest. The person interviewing you — hiring manager or not — has barely looked at your resume and cover letter. They aren’t going to remember yours over any of the other hundreds they’ve looked at. Or maybe they’ve only looked at your LinkedIn profile and not your beautifully designed resume and carefully crafted cover letter. I personally rely more on LinkedIn profiles than resumes because the consistent format from profile to profile allows me to more quickly digest someone’s background.

Whatever you do, don’t start describing your experience by saying “you have my resume, so I’ll be super brief.” Instead,

  1. Assume your interviewer doesn’t know a thing about you,
  2. Spoon feed them what they need to know; don’t make them work for it, and
  3. Yes, you still have to make your resume, cover letter, and LinkedIn profile perfect

But this is just the beginning. Stay tuned for more on other common pitfalls you might encounter when you next get that dreaded “tell me about your background” question.

The Distracted Goldfish