I was writing a work email and found myself spending an embarrassing amount of time staring at it before hitting send.
The message was short, the ask simple. I’d already read it aloud three times, checked the grammar, closed my browser, and pulled up the draft on my phone as if it might look different in a smaller font.
I wondered: Should I wait until tomorrow morning after they’ve had their coffee, add a “just” to soften the tone, or remove the sugary sweet compliment about the recent podcast episode that “made me laugh so hard” so they don’t think I’m a stalker?
Was it too soon to follow up after our SXSW meeting? Did I seem too eager?
I was treating a professional email like a text to a crush. Still, many of us approach our work emails with the very same fear: What if I come across as too much?
So we tone down our enthusiasm and trim down our messages until they sound safe and professionally detached—then wonder why people didn’t say yes to our vague, middling outreach.
After working as a marketing strategist with more than 200 business leaders and entrepreneurs, I’ve realized that, when we try to avoid sounding like “too much,” we censor the very things that make communication work: the clear point of view and the direct ask. In other words, playing it cool is costing you results in marketing and sales, founder storytelling, and partnership building.
Here’s what I say to my clients about using their enthusiasm to get more yeses in the workplace.
Don’t let playing it safe stop you from asking
When opportunities fail to materialize, it’s often not because someone rejects us. It’s because we never ask.
Early in my career, I almost talked myself out of emailing someone I’d admired for years to ask for a personal endorsement. It felt ridiculous. He was a marketing legend and thought leader I’d admired for nearly a decade, reading his blog ever since I was an undergrad. A mentor from afar, really. Who was I to ask? What if he said no?
Had I never sent the email, I’d never have received the yes, the recommendation letter that followed, or the chance to build a friendship with someone I had admired for years.
When you do ask, make it easy for a yes to follow. Most people are more willing to help than we assume, but they shouldn’t have to solve a puzzle to figure out what you’re asking for.
A strong ask usually answers four questions for your reader, who will be asking themselves:
- What do you want? Say this near the top of the email, not buried in the last paragraph. Be specific: “Would you consider endorsing my book?” or “Would you be open to a 20-minute coffee chat?”
- Why me? Then explain why you are reaching out to them specifically. Maybe you’ve followed their work for years, read their book, heard them speak, or met them briefly at an event.
- Why you? Next, give a bit of context about yourself. Link to your LinkedIn, website, or a couple of relevant pieces of work or media features.
- What is the next step? You don’t have to send every detail in the first email, but you should make it easy to respond. If you’re asking for a meeting, suggest a few windows in the coming weeks. If you’re exploring a potential collaboration, share the rough timing and ask if they’d be open to receiving more details.
Don’t let professionalism quash your personality
Nowadays, it’s easier than ever for people to run their message through AI or let it draft an email from scratch. The result is often a grammatically perfect message that isn’t so perfect when it comes to grabbing eyeballs, sounding like every other email in any given inbox.
Even if you’re not using AI, you may be tempted to tone down your email, deleting the sentence that sounded a little too much like you. Perhaps the compliment too and maybe even the emoji.
But I think sounding too interested isn’t the biggest risk—it’s acting so uninterested that people believe it to be true.
I’ve been called “enthusiastic” more times than I can count and wondered if it made me come across as less professional. Now, though, I think that might be the point. I want my feelings to jump off the screen and for people to know I care. If I sprinkle in a few smiley faces and exclamation points in the process, so be it.
Before you hit send, ask yourself: Which sentence did I delete because it revealed something about my actual observations or thoughts? That’s usually the sentence worth keeping.
This doesn’t mean every email needs to be funny or overflowing with exclamation points. It means making the person feel like they are reading a real email from a real person, not a message that could have been blasted to an entire list.
Instead of writing, “I love your work,” mention the article, podcast episode, or idea that stayed with you. Better yet, show how it changed what you did: “I tried the process you recommended, and it already helped our team move faster this week.”
Embrace the power of the thoughtful follow-up
Opportunities rarely happen from a single email. They happen because you’re willing to play the long game. I’m now jokingly known as “the follow-up queen” because of how much I live by this philosophy.
One pleasant, specific follow-up email after a meeting is what moves a conversation forward. If you discuss a raise, a project, or next steps on a phone call, follow up in writing, creating a record for both parties and keeping the conversation moving.
A good rule of thumb: Follow up once after about a week. If you don’t hear back, wait another week or two before trying again. After two or three unanswered follow-ups, step back and give it some space.
Silence does not mean the relationship is over. It means you shift from fighting the void to staying thoughtfully visible. You can share a relevant article or podcast when it connects to your previous conversation. Congratulate them on a company milestone. Send a short update when you have something meaningful to share.
Don’t feel guilty for circling back. Sometimes it’s just not the right timing, or they don’t have the budget yet. This isn’t a personal rejection.
I once landed a marketing project with a big client after nearly two years of thoughtful follow-up. It wasn’t because I sent the same email over and over. It was because I engaged with their newsletter and LinkedIn content, showed up when they had an event in New York City, shared occasional short updates, and stayed gracious, relevant, and on their radar until the timing finally made sense.
The biggest opportunities in my career didn’t come from perfect emails. They came from emails I almost didn’t send. So if you’re still staring at a draft thinking you’ll tweak it a little more or look again later in the hopes of it feeling less cringe, I urge you to hit send, close your laptop—and start dreaming about the next ask you want to make.
