Beyond the resume: master the art of telling your career story

A Hands-On Workshop for Crafting Your 30-Second Elevator Pitch

Welcome to this special workshop edition of our newsletter, summarizing key insights from my recent podcast episode on career storytelling. For the full, in-depth discussion, you can watch the complete episode here:

Today, we're not just discussing theory – we're rolling up our sleeves and diving into a hands-on workshop on the art of storytelling. Specifically, we'll be working together to craft a compelling 30-second overview of your career. This interactive approach will help you immediately apply what you learn, transforming your career narrative from forgettable to remarkable.

Self-Assessment: How Good Is Your Story Today?

Before we go further, take a moment for honest self-reflection. How would you grade your current ability to tell your career story in 30 seconds? If you're like most professionals I've worked with, you might sheepishly admit to a "C, maybe at best." This is a dangerous position to be in! After all, you spend 2,000 hours a year working—shouldn't you be able to explain your work compellingly in under a minute?

The Critical First 30-60 Seconds

Before we dive into our workshop, let's address a crucial point: the first 30-60 seconds of your story are absolutely critical. This brief window is often all you have to capture someone's attention and make a lasting impression. If you can't engage your listener in this short time, you may lose the opportunity to share the full depth of your experience and value.  So this article focuses on that first crucial minute.

The Hollywood Trailer Approach

Think of your career story like a movie trailer, not a plot summary. When Hollywood creates a trailer, they don't try to recap the entire movie—they show the most exciting parts to get you interested in watching the full film.

Similarly, your career story should hit the highlights and make people want to learn more about you. It's not about summarizing every job you've had, but about creating something memorable that "travels" well (i.e., is easy for others to repeat).

Why Your Career Story Matters More Than You Think

In today's competitive landscape, your ability to articulate your career journey can be just as important as your actual accomplishments. Here's why:

1. Differentiation: In a sea of similar resumes and LinkedIn profiles that often blur together, a well-crafted story helps you stand out.

2. Product Management Skill: If you can't effectively describe your own career, how can you describe a product? This storytelling ability is a core PM skill.

3. Creating Champions: A good story helps people who don't know you well become your advocates.

4. Invitation to Engage: It gives listeners a clear entry point to ask questions and connect with you.

The LinkedIn and Resume Blur

Let's dive deeper into the first point about differentiation. In today's digital age, LinkedIn profiles and resumes have become increasingly standardized. They often follow similar formats, use similar language, and highlight similar achievements. This "blurring" effect makes it challenging for hiring managers, recruiters, or potential collaborators to distinguish one candidate from another.

Consider this: A typical recruiter spends only 7.4 seconds scanning a resume before deciding whether to proceed with a candidate. In such a brief window, a list of job titles and responsibilities rarely makes a lasting impression.

This is where your career story comes in. A well-crafted narrative can cut through the noise, providing a memorable and unique perspective on your professional journey. It's not just about what you've done, but how you've grown, what you've learned, and where you're headed. This narrative approach can transform a forgettable list of experiences into a compelling journey that resonates with your audience.

The Challenge: Why Most Career Stories Fall Flat

After reviewing dozens of career narratives from both junior and senior professionals, I've identified some common pitfalls:

1. Too much detail, too little structure: Many try to cram every detail of their career into their narrative.

2. Grandiose, abstract stories: Some use vague, high-level descriptions in an attempt to sound impressive.

3. Focus on what was built, not why it mattered: Getting lost in project details without explaining their significance.

4. Overuse of jargon: Using technical terms that alienate listeners.

5. Vague personal contributions: Unclear distinction between individual and team accomplishments.

To illustrate these challenges and demonstrate how to improve, let's look at some real-world examples. These examples are from professionals at various stages of their careers, and we'll see how applying key storytelling principles can dramatically enhance their narratives.

Example 1: The Chronological Trap

“So I started off my career as a software engineering trainee with Brilio, which operated in an onshore offshore model where client services were in Europe and the development teams were based out of Bangalore. But once I started C# coding, I realized that quickly it wasn't quite for me mainly because it was too slow for my pace, which made me look around and seek other roles within the company. That got me a hands-on opportunity to design database on a small initiative. Which was very successful and that led to bigger things and eventually I stumbled into client relations.”

This example illustrates a common pitfall: starting from the very beginning of one's career and providing a chronological account. While it's a natural way to think about our careers, it's not the most effective way to present them.

Analysis:

• Starts with early career details, which may not be the most relevant or impressive part of the journey

• Focuses on what they didn't like rather than their strengths

• Lacks a clear career theme or direction

• Doesn't highlight current role or major achievements

Improvement Needed: The story should start with the current role and major achievements, then briefly touch on how early experiences led there. It should also articulate a clear career theme that ties experiences together.

Example 2: The Current Role Focus

“I lead the growth product team here at Shopify. So Shopify has three product areas, core, self explanatory, merchant services, kind of additional features, and then growth. Everything around how new merchants get up and running using Shopify. This is from where you land on our website to signing up, setting up your store, getting everything ready to go to make your first few sales and then continue to adopt more of Shopify as your business grows.”

This example shows an improvement in that it focuses on the current role and is very easy to understand, but it still misses important details you want to share in your first few seconds.

Analysis:

• Clearly states current role and company

• Provides context about the company's structure

• Explains specific area of responsibility

• Doesn't provide a career overview or journey

• Lacks personal achievements or unique value proposition

• Doesn't seed hooks for further conversation about career path

Improvement Needed: The story should briefly mention the career journey leading to this role and highlight a key achievement or two. It could also add a statement about career philosophy or future goals.

Now, let's look at how we can start improving these stories by applying some key principles.

Practical Tips for Improvement

1. Start with Your Career Theme: Begin with a clear statement that encapsulates your professional journey.

2. Highlight Reel: Choose 2-3 pivotal experiences that showcase your skills and impact.

3. Avoid Jargon: Speak in clear, accessible language.

4. Add Weight Without Jargon: Focus on concrete achievements, recognizable brand names, or unique skills.

5. Speak Naturally: Aim for a conversational tone that invites dialogue.

6. Unique Value: Clearly articulate what sets you apart.

7. Tailor for Your Audience: Have versions ready for different contexts.

8. Seed Conversation Hooks: Include intriguing details that invite follow-up questions.

9. Prepare Your "Greatest Hits": Develop a set of compelling 1-2 minute stories about your key accomplishments that you can reference for follow-up responses.

10. Future Direction: Hint at where you're heading next to invite questions about your goals.

Example: Applying a Career Theme

“I've spent the last decade and a half leading product teams and launching products in both larger organizations as well as startups in enterprise as well as consumer space that scale user engagement and bring new products to life so that we can generate more revenue. Most recently at GoodRx, I am the single threaded owner for all of consumer experience across all platforms with a cross functional team of 90 to 100 members that are responsible for creating an end to end frictionless experience so that we can acquire new users as well as retain our existing customers.”

Before: This initial version suffered from similar issues we saw in the earlier examples - vague terms, lack of specific achievements, and no clear career theme. After applying some of the tips above, listen to version 2.

“I'm passionate about scaling products and building product teams. I'm known to bring a unique blend of making everyone feel heard, but making hard decisions when need be to drive focused execution in every project. In the past 15 years, I've had three pivotal experiences in companies with hit products, and my work helped deepen the customer relationships. First was at Bill.com, which is a business payments company. I eliminated the manual process of invoice processing by using Google's AI technology, which was in nascent stages in 2016.”

After: Notice how the improved version starts with a clear career theme: “I'm passionate about scaling products and building product teams.” This immediately gives the listener a framework for understanding the subsequent experiences shared.

Analysis of Improved Version:

• Starts with a clear career theme and unique value proposition

• Provides a specific example of an achievement with context

• Sets up for further discussion about other pivotal experiences

• Avoids jargon and speaks more naturally

Example: Avoiding business jargon and adding weight naturally

While it's tempting to use industry jargon to sound more professional, it often has the opposite effect. Instead, focus on adding weight to your story through concrete achievements and recognizable milestones.

“So my background spans different roles in consumer growth and monetization. So I started out my career in brand marketing at an agency, helping tech clients like PayPal with their brand architecture and information architecture. I then quickly realized I wanted to move in-house versus, you know, working in agency life. So I discovered product marketing and took on a role at LinkedIn, which had just IPO'd and worked horizontally across several business lines, helping with things like content strategy, user research, campaign management and optimization.”

Before: The initial version was filled with vague terms and industry jargon, making it hard for the listener to connect with the story or understand the speaker's true value. Now listen to the improved version.

“My career has spanned roles across consumer growth and monetization, initially as a product marketer and then in product management. I'll share a few highlights from my time at LinkedIn, Credit Karma, and Headspace. I started my career as a marketer at LinkedIn, co-owning P&L for the JobSeeker Premium subscription, growing it from 30 million to 100 million in a few years. This was a time when LinkedIn was starting to focus on monetizing the free user base and diversify revenue streams beyond the flagship recruiter product.”

After: The improved version replaces jargon with specific achievements and clear language.

Analysis of Improved Version:

• Starts with a clear career theme

• Provides specific achievement with numbers (e.g., "growing JobSeeker Premium from 30 million to 100 million in revenue")

• Gives context to the achievement (e.g., "LinkedIn was starting to focus on monetizing the free user base")

• Sets up for further discussion about other experiences

Example: Making your story more personal and conversational

A great career story should feel like a conversation, not a recitation of your resume. It should give insight into your passions and motivations.

“So I started in product management about 14 years ago at Blackberry. And there I got to take the lead on conceiving and launching an app from zero to one. The experience of like being able to put something into market and see people use and enjoy it. I just, I got hooked. Prior to that, I'd worked in schizophrenia genetics research as a software engineer and program management. And I think product to me really felt like the home that I had been looking for.”

Before: I loved hearing about the passion for product management, but I suggested adding a clear career theme and trying to tie her passion into a compelling career overview.

“So I got started in product about 14 years ago and really just became fascinated with learning how to know what to build and how to craft a really excellent product. So over the arc of my career, I just basically went to like smaller and smaller teams with increasing leadership positions so that I could learn what makes a great product and what makes it successful in market. And for me, it's that intersection of really interesting customer problems, product crafting and product strategy is really what continues to drive me as a product leader. So let me tell you about what I worked on, and I'm going to start with the most recent stuff first and go backwards.”

After: The improved version maintains the personal touch while providing a clearer career trajectory and themes.

Analysis of Improved Version:

• Clearly articulates career theme and passion

• Outlines career progression (e.g., "went to smaller and smaller teams with increasing leadership positions")

• Sets up for further discussion about specific roles and projects

• Demonstrates strategic thinking about product development

Seeding Future Conversations

One of the most powerful aspects of a well-crafted career story is its ability to set up future conversations. Your 30-second pitch shouldn't just be a self-contained narrative—it should be a launching pad for deeper discussions.

Think of your career story as a menu of topics that your listener can choose from. By briefly touching on key experiences or skills, you're offering multiple entry points for your audience to engage with you further.

For example, if you mention that you led a major product launch, a listener might ask about the challenges you faced during that process. If you highlight your experience in both startups and large corporations, they might inquire about the differences you've observed.

Here's how to effectively seed these conversation hooks:

1. Mention intriguing projects: Briefly reference unique or impactful projects you've worked on, but don't go into full detail. This leaves room for questions.

2. Highlight diverse experiences: If you've worked across different industries or company sizes, mention this diversity. It opens up various avenues for discussion.

3. Allude to challenges overcome: Briefly mention a significant challenge you've faced in your career. People often want to hear more about how you navigated difficult situations.

4. Reference key skills or methodologies: If you've mastered specific skills or methodologies that are relevant to your field, mention them in passing. This can lead to more technical discussions if appropriate.

5. Indicate future goals: Conclude with a brief mention of where you're hoping to take your career next. This can lead to discussions about future opportunities or industry trends.

By seeding these conversation hooks, you're not just telling your story—you're inviting your audience to actively engage with it. This turns a monologue into a dialogue, making the interaction more memorable and impactful for both parties.

The Importance of Communication Speed

One often overlooked aspect of effective storytelling is the speed of communication. In many professional settings, the ability to convey information quickly and clearly is highly valued. If you can engage in rapid, back-and-forth dialogue about your experiences and skills, it signals competence and senior-level thinking.

When you remove jargon and speak naturally, you enable this kind of fast, engaging communication. It makes the conversation feel less like a formal presentation and more like a dynamic exchange of ideas. This can be particularly important in interviews or networking situations where time is limited and making a quick connection is crucial.

Tying It All Together: My Own Career Story

To illustrate how these principles can be applied, let me share two versions of my own career story. The first is a more generic version, while the second incorporates the techniques we've discussed for added weight and specificity.  Notice how the second provides more specific details and achievements, creating a richer narrative without relying on jargon. It gives clear "hooks" for further questions about specific roles or transitions, enabling a faster, more engaging dialogue.

Version 1 (Generic): “My career is in two stages - the first was a dozen years working for startups, three of which I founded. And then Act II was as a product manager, working at scale (Google, Meta) and Credit Karma, going through hypergrowth. In all of these companies, I've always been a hands-on entrepreneur. Focused on the product and driving new products, either for the first time, in the case of startups. Or expanding an existing product line, as I did in my last three settings.”

Version 2 (Added Weight and Specificity): “The first stage of my career focused on startups where I joined a startup, co-founded a dot.com that imploded, and then was founding CEO for two companies. One was bought by IBM and the other by Google. Act II began when I joined Google as a product manager. I helped launch Hangouts as the lead PM and then organized the PM team for today's Google Photos. I left Google to try my hand at hypergrowth, joining Credit Karma to transform their product from a free credit score website to the "money button on the phone". As the company transitioned to Intuit, I left and joined Meta to lead several core products including Video and Groups for Facebook. In my heart, I'm an entrepreneur. But I've learned you can be an entrepreneur at any stage of company, whether it's expanding product lines with Google, Meta, and Credit Karma or getting companies off the ground as I did with my startups.”

Workshop Activity: Craft Your Story

Now it's your turn to put these principles into practice. Follow these steps to craft your 30-second career story:

1. Write down your career theme in one sentence.

2. List 2-3 pivotal experiences in your career.

3. Identify your unique value proposition.

4. Draft a brief statement about your future direction.

5. Combine these elements into a 30-second story.

6. Practice delivering your story aloud and time yourself.

7. Refine and iterate based on how it sounds and feels.

Remember, this is an iterative process. Your first attempt doesn't need to be perfect. The goal is to start crafting a story that you can continue to refine over time.

Crafting an effective career story is a skill that requires consistent practice and refinement. Don't be discouraged if your first attempts don't feel perfect—even seasoned executives often struggle with this. The key is to keep iterating and refining your story.

Remember, your career story is a powerful tool. Invest the time to craft it well, and you'll find doors opening more easily throughout your professional life. Keep practicing, keep refining, and watch how it transforms your professional interactions.