I recently got an email from a reader with the following question:

How would you approach making a spontaneous, impressive first impression when meeting someone you admire — like a dream mentor, executive, role model, etc. — in an unexpected moment?

I love this kind of question because it forces me to deconstruct and teach something that may have started to feel like autopilot in my own life.

And this particular question is very important for your life and career:

It takes considerably more energy to change an impression than to make one—so we need to pay close attention to those early interactions, as they shape the long-term arc of the relationship (or lack thereof).

This isn’t about being fake or overly polished. It’s about being intentional with your presence to make the most of that tiny opening. It's about capitalizing on that "lucky" break. It's about creating your own luck.

So, here's my open letter in response to that reader's question:

5 tactical rules to make a great first impression...

1. Preparation is an asymmetric investment

An asymmetric investment is one where the downside is limited but the upside is potentially significant.

In my experience, a short, focused block of preparation prior to an event, dinner, conference, or gathering is a clearly asymmetric investment—it has limited downside (the time) and significant upside (all of the potential value from the new relationships).

Take a few small actions to prepare:

• Spend 15 minutes reviewing the attendee list if it’s available. If it isn’t, ask the organizers if they have a sense of likely attendees. You can usually get your hands on something.
• Make a mental note of any recent news, interviews, interests, or updates from people you admire that may be there.

It requires very little effort, but it can create the perfect opening for a thoughtful question, spark, or connection point.

That's Rule 1: Preparation is an asymmetric investment.

2. Simple is much better than impressive

There's a trap that most people fall into when they meet someone they admire:

They try to sound impressive in order to stand out.

This generally manifests as a long, winding intro on their entire background and a list of titles, jobs, and awards.

Unfortunately, what you say vs. what the other person hears are two very different things. The "impressive" intro often ends up being perceived a lot like this classic meme:

Try this three-part model to simplify your personal intro statement:

1. Name
2. Primary professional focus (or interest)
3. Something related that you've been focused on or excited about

So, my version might look like this:

Hi, I'm Sahil Bloom. I'm a writer and I'm getting excited about how I can create more community around my ideas to deepen their impact.

Notice that I didn't say anything about (1) the size of my following, (2) any accolades or recognitions, or (3) the specifics of my writing.

The entire intro would take less than 10 seconds and likely open the door to a handful of natural follow-up questions from the other person (e.g. what do you write about, how do you currently reach people).

I like this simple model because it forces brevity and leaves a lot of "meat on the bone" for follow-up discussion.

It also naturally engages a pattern interrupt (more on this later) in that your intentional humility will stand out from a crowd who all seem hell-bent on telling you about their professional wins within 10 seconds of meeting you.

That's Rule 2: Simple is much better than impressive.

3. Interesting questions make you interesting

Stop trying to be interesting—instead, focus on being interested.

Interested people ask great questions, and great questions are the best way to leave a lasting impression.

In other words, interesting questions make you interesting.

Here are some interesting questions I love:

• What are you most excited about right now? It gets the other person talking about something exciting in their life (personal or professional). It's a 10x better alternative to the "what do you do?" standard fare opener.
• If you could put one piece of advice on a billboard for the world to see, what would it be? Someone recently asked me this one and now I'm obsessed with it. It often sparks a longer dialogue on the most important advice the person has received, which makes for engaging conversation.
• What's been your best purchase under $100? Always sparks a fun line of thinking.
• If you had an entire day to yourself with zero responsibilities, how would you spend it? This is a great question to get away from the traditional career and professional conversational track and explore deeper values and interests.
• What have you changed your mind on recently? This tends to uncover some cool insights and personal development.
• If you could have dinner with 3-5 people from any point in history, who would you choose and why? A fun thought experiment for a deeper conversation when you find yourself in a more drawn-out setting (like seated next to someone at an event meal).

Note: If you feel awkward jumping into any of these, you can open with "Someone asked me this recently and I thought it was really interesting..." to make it feel natural.

All of these questions are ​doorknobs​, meaning they invite the other person to respond with a story as they walk through the door. By asking doorknob questions, you create conversational momentum.

Think about your own response to these questions before using them, as you’ll likely encounter situations where the person flips them on you to get the conversation moving.

That's Rule 3: Interesting questions make you interesting.

4. Lean into your pattern interrupts

When you're a kid, you're taught to fit in.

But here's the truth: The thing you fear as a kid (being different) becomes the thing you get rewarded for as an adult.

I call these pattern interrupts—the things about you that interrupt the normal pattern that people have for you.

Most people lean away from their pattern interrupts, but if you want to make a great first impression, you should lean into them.

As it turns out, the things that make you weird are often the things that make you memorable.

If you're an accountant who loves stand-up comedy, say it. If you're a finance professional who moonlights as an opera singer, own it. If you're obsessed with meditation, share it.

Some of my most transformative professional relationships were sparked through sharing my quirky health routines (cold plunging, sauna, running, lifting, etc.) in a first interaction. It's different from what someone would expect from a writer, and it allows me to lean into something I'm energized by in a conversation. It also turns out that a lot of high performing executives are thinking about their health nowadays, so it's perfect.

An impressive person might meet 100 consultants, accountants, lawyers, doctors, or investment bankers in a year. But the one who’s obsessed with photography or runs a side business roasting coffee beans? That’s the one they'll remember.

That's Rule 4: Lean into your pattern interrupts.

5. Embed (and execute) the thoughtful follow-up

If you want to turn a strong first impression into a genuine long-term relationship, you need to catalyze a follow-up.

The best follow-ups are natural—they’re planted in the initial conversation.

A few examples I often turn to:

• Mention a book you’re reading
• Reference a podcast episode you loved
• Talk about a unique article you came across

All of these are organically relevant to a conversation and create a very natural follow-up for later.

Then, within a few days of the interaction, actually follow up:

• Send an email with a simple note (e.g. "Great meeting you. Here’s that podcast I mentioned. Thought it might resonate!").
• Send them a copy of the book with a handwritten note.

Note: My NYT bestselling book has a follow-up outreach guide with specific strategies to execute these follow-ups, including how to guess their email address if you didn't get it and some other creative approaches. ​Order it here​.

An important reminder for these follow-ups: There's no specific ask, no request, no transaction. Just genuine attention to detail. The bar for thoughtful follow-up is low—almost no one clears it. So when you do, you stand out.

That's Rule 5: Embed (and execute) the thoughtful follow-up.

The Little Key to a Big Life

"A very little key will open a very heavy door." - Charles Dickens

First impressions are an opportunity. A potential asymmetry.

A little preparation, a curious question, a thoughtful follow-up. A small energy investment with the potential to unlock massive opportunity.

That mentor who changes your outlook. That business partner who complements your skills. That new opportunity that was previously invisible.

Your presence and intention are the little key that unlocks a very heavy door.

Follow these five simple rules and you will make a great first impression.

You will have the little key to a big life.