If you're reconnecting because you need something, say so up front, acknowledge the gap, give a clean out, and keep any catch-up separate.
The idea
We're afraid of looking like we only show up when we need something, so we try to manufacture connection first with questions about the kids, the city, the new puppy. That makes you come across as more transactional, because you're trying to pay for the ask with forced small-talk currency. People know when they're being buttered up, and hiding your agenda creates distrust later. Being upfront neutralizes that, and if the person cares about you and is able to, they'll likely be happy to help.
How to do it
Lead with the ask. Be direct and specific.
If it's been a while, say so.
Make it easy to say no.
If you genuinely want to catch up, make that its own thing, separate from the request.
Example
The email that opens with "Long time no talk! How's [your city]? Saw your new puppy on Instagram!" and then pivots to "Speaking of which..." fools nobody. Everyone knows the ask is coming.
Script
"Hey Sarah, I'm reaching out because I'm organizing a fundraiser and would love your input on [specific thing]."
"I know we haven't caught up in ages, and I'm reaching out because..."
"No pressure at all if this isn't your thing or if timing isn't right."
"Would also love to grab coffee soon - completely separate from this request."
Kill the Vague Ask: Say what you want, how long it takes and why them, and build in an easy out so that "no" is safe.
Reconnecting After a Long Silence: Skip the apology. Send a short note that they came to mind, ideally with one real detail or shared memory, and leave the ball in their court.
Release a Stalled Favor: If an intro or favor has stalled, tell them there's no pressure. Lifting the guilt often prompts them to finally do it.
Have Your Ask Ready: Prepare a one-line, specific answer to "what would be most valuable for you?" and put it in your signature and bios.