Your Response To “Tell Me About Yourself” Sounds Like Everyone Else’s

JOB SEARCH STRATEGY WITH EARLY.

Nobody is born a natural storyteller.

It’s a skill, the same as writing or public speaking, and most of us only pick it up when we are suddenly forced to.

Take the job search. Before an interview, you prep your answer to "tell me about yourself," and I would happily bet a hundred bucks it comes out as some version of "I've spent six years in the industry, I'm looking for a new challenge, and my strengths are..."

Which is just fine, but it’s also the same run of the mill answer half the other applicants are giving.

If you want a startup career with a bit more color to it, the kind where opportunities start coming to you instead of you forever chasing them, learning to tell your story is one of the best things you can do.

I say all this as someone who used to be terrible at storytelling. Fixing that is what led me to build an accelerator teaching people to own their story, and an audience of more than 65,000 I now share it with for free.

So, let me tell you about my Dad. He will hopefully forgive me for this, but he sucks at storytelling, and on one particular afternoon, he helped me realize what I needed to change.

I was stuck in a car for four and a half hours with my parents, my in laws, and my very pregnant wife. It was my in laws' first trip out to the Pacific Northwest, and I was dreading how we were going to fill the silence.

To fill it, my Dad started telling one of his stories.

For the first few minutes, everyone was locked in.

Fifteen minutes later he had wandered off the start of the story and into one of his old law cases.

My mother in law turned to my wife and struck up a completely separate conversation.

Thirty minutes in, we were hearing about the babysitters we had growing up, and my father in law was staring out of the window.

Forty five minutes in, my Mom was asleep in the back seat with her mouth wide open.

Then, finally, the story reached its big finish.

"So Russell ate the meatloaf sandwich."

Everyone just sat there in silence. I turned to him and said, "You talked for the better part of an hour and the ending is that your brother ate a sandwich?""

Everyone burst out laughing, and then an uncomfortable thought hit me: this was exactly how I told stories. This rambling “all inclusive” style of storytelling is very common unless you know how to capture attention.

In this issue, I am going to show you how to own your story, and give you a simple framework to build it so it sets you apart in your job search and carries you through the rest of your career.

Table of Contents

• You need to stop hedging your story

• It matters even more at a startup

• How to build confidence in your story

• My framework to nail your story

• Don't make them guess

1. YOU NEED TO STOP HEDGING YOUR STORY

A company is hiring a person, not a list of achievements. So how you tell your story in your applications, interviews, and anywhere you’re present online, is incredibly important.

If you’re able to be clear on who you are, what you've done, and where you’re going in your career, you’re going to give the interviewer much more to grab onto and talk about with you.

I don’t like being purely theoretical about this, so let me show you the difference between an okay story and one that will make you stand out, using my own experience.

When I quit my job in Seattle and moved to New York, I had two ways to tell that story.

Here is the first: I was in a pretty miserable job, so I quit, moved across the country, and spent a month or two between roles hoping the experience I had would be useful to whoever I was talking to.

Here is the second: I was working at a company in Seattle, and I could see the opportunity I actually wanted was in New York. I knew it would be almost impossible to break into that world from the other side of the country, so I quit, I moved, and since then I have been meeting a stream of interesting people and getting sharper and sharper on exactly what I want to do next.

Every word of both is true and they have the same facts. It’s just that the first version is hedged and apologetic while the second one is owned.

This is the thing I see come up again and again when I coach Early accelerator members. People will not own their story and they apologize for their own history even if no one has questioned it. It’s a strange polite thing we do that works against us.

“It was only a small team. I was only there a year.”

“Does it look weird that I spent that time doing my own thing?”

“Well we worked as a team to achieve the result really…”

We’re so used to second guessing ourselves that we flinch every time someone asks what we’re good at or excited about and it leads to muddied results.

Hedging is your worst enemy in the interview process. When you are hedging, you do not connect with the person across from you, you do not come across as confident, your experience stops sounding interesting, and you’re simply not as memorable.

Now while you can’t change what’s on your resume, your story is entirely yours to shape (within reason, of course!).

2. IT MATTERS EVEN MORE AT A STARTUP

A startup is a small team who are going to spend nearly every waking hour together and much of that time will be hard stretches.

So when they interview you, they are not only working out whether you can do the job. They are working out whether they want to be in the trenches with you for the next few years. At a startup, likability and fit are part of the actual job. More than anywhere else, startups hire the eccentrics, the passionate, the oddballs, the misfits, the obsessives, and the freaks.

That is good news for you, because it means your story and your personality are a real lever.

There is a specific way to pull it: do your homework on what the company is building and why it matters to the founders, then make your honest connection to that mission part of your story.

When someone can see that you care about the same problem they have poured years of their life into it shows that this isn't just one of a hundred jobs you're applying to, there's purpose and passion behind your application.

The version that makes the interviewer's eyes glaze over is the polished, buttoned up, just the facts one.

I have sat through interviews where the candidate shared a flawless resume and picture perfect answers, but it left me feeling like they weren’t excited about the role.

That can work in the corporate world but it’s a different ball game for startup hiring.

Hiring managers want to hear how you’re owning your career instead of how you’re ticking perfect boxes.

3. HOW TO BUILD CONFIDENCE IN YOUR STORY

So how do you get to the owned version of your story? Well, not by bluffing.

The confidence comes from going back and actually looking at what you have done. When I sit with someone stuck in the hedging trap, we pull up the receipts:

• What’s the impact you actually drove?

• Recall the customers you worked with. How did you solve their issues?

• What mistakes did you make? How has that changed your perspective?

• What did you learn from the people you worked alongside?

• What stage of company have you worked in, and how will that experience translate into your target companies?

Other people haven’t been able to experience exactly what you have.

If you ask yourself these question, what you are left with is a pile of raw material: the moments, the wins, the mistakes, the turns. But on their own, they are just receipts.

The next step is shaping them into something a person can actually follow and remember, and that is exactly what the framework in the next section does.

4. MY FRAMEWORK TO NAIL YOUR STORY

Matthew Dicks, who teaches storytelling everywhere from Yale to Amazon, says:

"Our minds are not designed to remember a pie chart or facts or statistics or platitudes or ideas that are not attached to imagery. So the risk you take if you're not telling stories is that you will be forgotten. 100%. You will be forgotten."

The job now is to take all that raw material you just dug up and give it a shape, without overcomplicating it.

The shape I use has three parts: present, past, and future.

Present is where you are now, led by the work you are proudest of.

Think of it as your anchor: before you take anyone back through your history, they need to know who they are talking to today. When you write yours, keep it to a line or two, what you do now and the one or two results that make you proud of it. This is your chance to frame how they think of you through the rest of the interview so make sure you're describing yourself as exactly what they need through the lens of your background.

Past is where you walk back through the turns that got you here. It’s tempting to recount your job history in order, but I want you to resist that.

When you write yours, pick out three or four turning points instead, the decisions, the risks, the moments that changed your direction, and connect them so they lead naturally into your present.

Within those turning points there is usually one that matters more than all the rest, the single beat, a few seconds long, where everything changed. Matthew Dicks calls these the five second moments of transformation, and they're the ones to slow right down on.

Don’t rush past the transformation, because that beat is what an interviewer walks away remembering, and repeats to the rest of the team when they decide whether to hire you.

In addition to the transformation, make sure that the wins, learnings, and skills that you gained in each role stack perfectly together to match what the hiring team has listed in the job description. Instead of saying, I did this and this and this you're telling them a story that naturally stacks all the experience and skills they're looking for.

Future is where you connect all of it to where you are going, and, most importantly, to the role in front of you.

This is the part that makes an interviewer feel like your whole story has been building toward their company.

When you write yours, name what you have seen or learned that makes you right for this specific problem, and say plainly why this team excites you.

Here is all of it put together, the way I would actually tell it:

Notice the shape: the first paragraph is the present, the middle is the past with that third rejection as the five second moment, and the last is the future, landing squarely on the company in front of me.

Also notice I own Avo's failure, I don't apologize for it. I share what I did and where things took a turn for the worse without it impacting my confidence or my ability to do the job at hand. If anything, I use the failure as a reason why I'm going to be good for the job because I've seen what can lead a company to fail and will be able to see the warning signs before the damage hits.

One last move, once your story is built, tailor it to the company you’re interviewing for. Make sure everything points back to the company and the role. Every skill, example, and story should be able to be directly tied to what they're looking for in the job description.

If you can't directly tie it to the JD and if there's no clear explanation to "why is this in here", eliminate it.

Your goal is to be able to tell this story in under 2 minutes. Anything over 2 minutes will have your interviewers asleep and eat into their ability to ask you the questions that will lead to an offer.

5. DON’T MAKE THEM GUESS

However clean the story you just built is, there is usually one part of your resume that does not sit neatly inside it.

If you had a career jump, like spending a couple of years off, moving from sales into marketing, running your own thing for a while, or taking a detour into a company that didn’t match your mission for your career, that’s ok. As long as you address it and don’t leave recruiters guessing.

If you leave it and just hope the recruiter doesn’t see, they might write their own story about the jump.

Instead of letting them think 1+1=10, you should:

• Give the real reason: the decision you made and why, told with the ownership we talked about earlier, not dressed up as an excuse.

• Highlight what you gained: there's definitely something you gained, learned, or accomplished during that time. Own it and do what you can to relate it to the job to be done in the target role and a character trait they're looking for.

• Connect it to now: draw a straight line from that decision to why you are the right person sitting in front of them today.

Your challenge this week

This is exactly what we run new members through in our Early job search accelerator. Now I’m challenging you to do it in one hour this week:

1. Ask yourself the questions I laid out in part 3. Read back through them once you’re finished.

2. Write your three part "tell me about yourself," present, past, future.

3. Pick out your five second moment, the single beat where everything changed.

4. Record yourself saying the whole thing out loud and play around with the tonality and structure of it. I often find people write the thing that should go first, last in their story. Don’t be afraid to move things around.

5. Read it back and be ruthless. Cut any line that could have come out of any other applicant's mouth or that can't be directly tied to the company and the job description. If it sounds generic, it is, and it goes. Then, for bonus points, grab a friend and do a mock interview to get practice and feedback.

Hell, if you reply to this email with your outline, I’ll read through and give you a pointer. I read every response.

Let’s go get you that job! 🏆

Kyle

Founder of Early

P.S. Whenever you’re ready, here are the three more ways I can help you this week:

1. Apply to join the Early Accelerator - Get coached directly by me, surrounded by a community of hundreds of badass startup operators. This is everything I learned when landing my role as Uber employee 250 and transitioning post-layoff to a Series A with top VC investors. We give you everything you need to make your startup job search a success. Structure, accountability, strategies, investor-grade company data, target company lists, negotiation assistance, everything to help you win.

2. Download the Clarity Playbook (FREE) - the exact process I walk every Accelerator member through to lock in their Role, Impact, and Company before they ever write a post or send a resume. Start here!

3. Use the Proof of Work Finder (FREE) - this prompt finds the highest-leverage Proof of Work you can create for a target startup, builds it with you, and pressure-tests it so it doesn’t read as generic. Send your Proof of Work to the team and create a huge gap between you and the second-place candidate.