The Secret to Selling Yourself in Seconds

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It’s been over a year since my first article about how to tell a story about yourself. I’ve amassed significant feedback from its use in the wild. 

I discussed the importance of making a powerful first impression and the anatomy of impactful storytelling. I also added stress for many readers by recommending that all stories should be a brief 90-second snippet.

I’ve even watched groups of executives in transition timing themselves and practicing together—sometimes with big smiles and appreciation—and other times with frustration and agony. 

While I’m not backpedaling from my prior commentary, I’ve come to understand further recommendations in my experiences of late that I need to share.

Today is the time for more color and revisions regarding the 90-second challenge and the differences between a good impression and being impressive. 

For what it’s worth, I will never write an article universally applicable to all career scenarios. 

An astute reader like yourself will recognize that how an executive navigates their career is highly subjective. Therefore, my work and perspectives are not gospel. And thank goodness for that. 

You will never wholly optimize your career or craft a universally perfected narrative. 

No objective rules exist to master such a personal, nuanced, and ever-changing subject. Yet, there’s beauty in your creativity and how you use it to meet your career needs. 

Let’s hop into revisions. 

90 Seconds, Really?

I’ve received a lot of pushback on consolidating your stories into 90 seconds. 

“Jacob, how am I supposed to explain my 25-year career in a minute and a half?” 


One. You’re not supposed to win someone over in 90 seconds with your life story. 

Snarky sarcasm aside—let’s unpack.

What I mean is—you’ll need to tactfully highlight key growth moments or milestones in your career that are relevant to your audience—and omit anything irrelevant to your audience. And let’s be honest, most of your career is not as relevant as we’d like to think.

Two. I didn’t mean 90 seconds—literally. 

The 90-second challenge is designed to remind you that you shouldn’t monopolize the conversation waxing poetic about yourself and reciting a robotic monologue of yawn-inducing chronological hogwash. 

The nitty gritty details about your career often do not matter anymore. And what you’ve done in the past isn’t as impressive or transferable in many cases. 

Building confidence and earning the trust that you can perform moving forward and solving new challenges is all you need to accomplish. Even if the challenges you’ve solved before are seemingly the same as the challenges a prospective employer faces today—there are unique circumstances that you must unpack. It’s not always, been there, done that, can do again.

The point is to concentrate on what matters most to the person you’re speaking with, introduce what matters to you, and ideally, find a shared identity, mission, and purpose.

If you don’t know how to do that, you’ve:

  1. Not done the proper research on the organization, role, or individual you’re speaking with.
  2. Not asked the right questions to steer the focus of the conversation into more meaningful and productive territory. 
  3. Overestimated your qualifications for the role, and you aren’t the right candidate. 
  4. Gotten yourself into a poor fit interview process.
  5. Found yourself oblivious to empathy and may come across as overly self-interested.

A strong-fit, competitive executive understands how to dissect the individual and organization’s needs—and directly apply how they can help them overcome their challenges while concurrently “telling them about themselves.” 

If this takes you 108 seconds, great. 

If this takes you 28 minutes, and you pause to involve the other party, ask thoughtful questions, and engage in meaningful dialogue that gives you more context on the role—and you’re still telling someone about yourself—you’re likely still winning. 

Sometimes the process carries on for months, especially for big-time C-Suite decisions, mergers and acquisitions, or significant re-orgs of behemoth conglomerates. 

Yes, even telling someone about yourself over months or years is also okay. That could be a lesser-known advantage of proactively updating the right folks in your network throughout your career. Gotta keep those irons in the fire hot and ready at any time! 

No perfectly crafted script or timeline is the right answer. 

Harboring empathy and understanding of the challenge ahead is much closer to the right answer, albeit only sometimes enough to win the deal.  

Regardless, it’s not about you; it’s about them—until you have an offer to be the solution—then it’s about WE.

A Powerful First Impression?

Knowing what I now know, I wouldn’t advise you to overly concern yourself with the impression you leave. 

You may now think I’ve officially flown the cuckoo’s nest. Please don’t take this out of context. 

You’re supposed to leave a good impression—why would you advise me not to focus on a good impression? 

Yes, the lasting impression is critical to your success, and you should think about how other’s perceive you (If you care about their opinion of you). 

Hell, you can even masterfully calculate a game plan to take more robust control of how you’re perceived. Though, that may be overkill and lead to disingenuous manipulation. 

Being casual, relaxed, and empathetically curious is more critical to success than thinking about how to leave an impressive impression concerning your body of work. 

I digress.

I’ve found in practice that most executives confuse leaving a good impression with trying too hard to be impressive. Unfortunately, they are not the same. 

It’s more important to find alignment than to prove that you are impressive. 

Being aligned as a team to solve upcoming business challenges is impressive. Plus, too often a rare feat at the highest of executive rungs. 

Naturally focusing your energy on their needs is what earns the strongest impression. 

Applying this strategy means asking more (pointed) discovery questions, listening to understand, deciphering what’s not being said (reading between the lines), and openly discussing topics that can sometimes be challenging. 

Pro tip: Being the first to openly admit failure, disappointment, or embarrassing mistakes that you’ve made can invite the other party to participate. It’s like you’ve permitted them to remove the facade and not always be so damn perfect.

And yes, you can do this while answering the “Tell me about yourself” question.

For example.

Tell me about yourself.

“Let’s see. I’m a father, husband, and adventurer living in Northwest Montana. I led a decade-plus career as a marketing and product executive in Silicon Valley before founding and leading a multi-million-dollar senior executive career transition company. 

Now, there are several areas we can explore from here—wins, losses, and some severe screw-ups—but before we go on, I’d like to understand why we’re on the phone today. I suspect you’re working on a go-to-market strategy for the coaching industry and need fresh perspectives. What are some of the challenges you’re facing? How can I best show up for you today?”  

This approach is short and direct. Perhaps more importantly, it asserts the conversation forward and provides an agenda for possible talking points. 

Of note, you can only cover some of your expertise in a single conversation. GOOD. You must give your audience a flirtatious and compelling reason to keep talking to you beyond this call—instead of the vapid, scripted fools you compete with. 

In summary—you’re not there to talk about you. Even when the question is, tell me about you! You are there to talk about them and their challenges. 

Is there alignment? How do you know?

What questions must you ask to determine whether you’re a good fit for them? And what questions can you ask to decide whether or not they’re a good fit for you?

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