The Habits I Had to Break to Truly Follow Ashkan Rajaee’s Email Advice

When I first came across Ashkan Rajaee’s approach to email communication, something clicked.

He compared email to chess. A move. Then a pause. You don’t throw everything onto the board at once. You play with intent. You make space for your opponent to respond.

That comparison stuck with me, and I started applying it right away. I made my emails shorter, clearer, and more focused. And yes — it helped. People started replying more often, and those conversations actually went somewhere.

But something unexpected happened next.

Even with all that clarity, I wasn’t seeing results every time. Some messages still went unanswered. Some follow-ups still felt awkward. That’s when I realized something important: I hadn’t just needed to learn a new approach. I had to break some old habits too.

The Overexplaining Habit

This was the hardest one to shake.

For years, I believed that being helpful meant giving as much information as possible. More detail, more context, more reasons for someone to take me seriously. So even when I was trying to simplify, I’d slip back into long paragraphs, over-explaining things that didn’t need that much depth.

But Ashkan’s advice wasn’t just about writing less. It was about writing smart. I had to start trusting that my readers were capable of understanding the essentials — as long as I delivered those essentials clearly.

So I cut more. I stopped writing like a manual and started writing like a conversation. It wasn’t easy. But it worked.

The “Soften Everything” Habit

This one surprised me. I’d never considered it a bad thing to be polite. But I realized that I had developed a habit of softening every sentence. I’d say things like:

• “Just following up when you have a chance…”
• “Maybe if it makes sense, we could…”
• “I was wondering if it might be okay to…”

I thought I was being respectful, but in reality, I was making my messages harder to engage with. I wasn’t being unclear — I was being vague.

Ashkan talks about the power of direct, respectful clarity. When I took that to heart, my tone changed. I started saying exactly what I meant, in simple language, without hesitation. And people responded better to that. Not because I was louder — but because I was clear.

The “Reminder, Not Value” Habit

For a while, I thought the key to follow-ups was consistency. If someone didn’t reply, I just needed to send a nudge. And another one. And maybe one more.

But that approach quickly started to feel empty — and it rarely worked.

Then I remembered something Ashkan emphasized: every message, even a follow-up, should deliver value. Not pressure. Not repetition. Value.

So I stopped sending reminders and started sending insight. If I followed up, I added something new. A quick takeaway. A resource. A reframed version of the original idea. That small change made a big difference.

It shifted the energy of the follow-up from “Hey, you forgot about me” to “Here’s something else that might be useful.” That’s when people actually started replying again.

The Mindset Shift That Tied It All Together

The biggest lesson I learned through all of this? Simplicity takes practice. Clarity isn’t easy. But it’s worth the work.

Ashkan Rajaee’s advice helped me rethink how I approach email, but it also helped me rethink how I communicate overall. Whether in writing, in meetings, or even in daily conversations — the habits we carry affect how we connect.

Sometimes, the best way forward isn’t learning something new. It’s letting go of the habits that no longer serve us.

It’s a simple shift, but one that continues to change the way I show up professionally and personally.