why your DMs with leads fail

Ever sent a message to a lead that you knew was gold…

…and then watched it die a slow, painful death in “Seen” purgatory?

Yeah, that’s because most DMs fail for one ridiculously simple reason:

You’re starting too big.

You hit them with:

“What’s your biggest challenge right now?”

or the infamous… “what are you most excited for in 2026?”

Just terrible.

Here’s the problem:

These questions makes your lead stop and…

→ think deeply for 2.7 seconds…

→ decide to answer later

→ forget you existed

Because your question = work.

And they’re already swimming in a sea of Slack pings, half-read emails, and lukewarm coffee.

But, good news, the fix is simple.

You have to make the question super easy to answer.

Questions like:

→ “Are you guys local or international?”

→ “Is your team mostly remote or in-office?”

The best examples are a “this or that” question.

Because it preloads the answer in their mind.

No heavy lifting. No life reflection required.

Just a quick, friendly answer that opens the door to a real conversation.

Once they respond, they’re way more likely to invest time in the conversation.

When it gets rolling, you can start asking the juicy stuff.

So next time you slide into someone’s DMs…

Skip the deep therapy questions.

Start small.

Get the ball rolling.

And watch your replies multiply fast.

See you all next Thursday 👋

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