#18 Why "just catching up" is more strategic than you think

TL;DR:

December conversations look casual, but this is when people are the most reflective and the most willing to talk about what’s actually going on inside their teams. If you stay in intel-gathering mode instead of “please validate me” mode, you’ll get context you won’t get any other time of year.

Why “Just Catching Up” Is More Strategic Than You Think

December is the easiest month of the year to get someone on a call.

People slow down.They look back at the year.They think about what needs to change next year.

So a message like:

“Hey - hope the year is wrapping up well. Would love to catch up.”

…gets a yes at a much higher rate than usual.

But here’s the part that throws people:

If you’re job searching or thinking about a pivot, a “catch-up” can feel too light.

​Too casual.

Like it won’t move the needle.

And under that is the real fear:

You don’t want to show up looking like you’re asking for something.

Or worse - like you’re seeking validation or permission.

And that’s exactly when people freeze.

Because yes, they might be open to the conversation…but that doesn’t mean you feel confident walking into it.

The minute the call lands on your calendar, the spiral starts:

• “What am I supposed to say?”

• “Is this going to be awkward?”

• “Do I need a pitch?”

• “How do I make this useful?”

A client said this to me last week:

Not because he lacked experience.

But because he was treating networking like a situation where the other person gets to grant approval.

Once we removed that dynamic, everything got easier.

Here’s the shift:

December networking isn’t about trying to impress anyone.

It’s about gathering intel.

People talk more freely this time of year because they’re not in “go mode.”

They’re thinking out loud about:

• what's changing

• where the gaps are

• what they wish they had

• what next year should look like

You get the candid version - which is gold.

Here’s the exact approach I gave my client:

1️⃣ Lead with direction — keep it simple

No pitch needed. Just context so the conversation has a frame.

“I’ve spent the last few years driving X, and I’m exploring roles where I can do more Y next year.”

Clear. Grounded. That’s enough.

2️⃣ Share a through-line, not your entire CV

You’re not trying to impress them. You’re helping them place you.

• last 3–5 years

• your core value

• the direction you’re exploring

  
  

Short > detailed.

3️⃣ Ask about what they’re seeing [that's the point]

Skip the questions that sound like you want permission:

❌ “Do you think I’m a fit?”

❌ “Should I apply?”

❌ “Do you know anyone hiring?”

Instead, ask questions that actually get you somewhere:

“What’s shifting on your team for next year?”​​

“Where are you seeing priorities change?”​​

“What skills matter most right now on your side?”

People are already thinking about this.They’ll give you the truth.

4️⃣ Keep it reflective - not evaluative

You’re not interviewing them.

You’re not being interviewed.

You’re collecting context.

Try:

“I’ve been talking to people across [x companies/industry] to get a sense of what’s changing - I’d love to hear what you’re noticing.”

Easy, equal, human.

5️⃣ If there’s a next step, they’ll say it

When the conversation is grounded and not transactional, people naturally offer:

“You should talk to…”

“We might need someone like you next year…”

“Let me introduce you to…”

No pressure, no awkward asks.

Just doors opening because you showed up as a peer.

What happened for my client

After one call, he said:

And suddenly people were sharing real insight, real context, real openings.

Not because he “networked better.”

Because he stopped shrinking.

Final thought

If you’re reaching out to people this month, remember:

A catch-up isn’t small talk.

It’s a chance to hear how people are actually thinking about next year... and where someone like you could fit.​

​Take advantage of it.