Ten outreach attempts. Ten silences. For one content creator hoping to land informational interviews at companies they admired, the networking playbook was being followed to the letter — LinkedIn messages, phone calls, emails, even second and third attempts through different channels when the first didn't land. And still, nothing.
It's a familiar frustration, and one worth pausing on before assuming the strategy itself is broken. Reaching out cold, trying multiple channels, following up when the first attempt goes quiet — these are exactly the right instincts. The problem usually isn't effort. Its aim.
Stop Reaching Sideways — Reach Up
The instinct to contact peers in a target company's communications department makes sense on the surface, but it often backfires. Staff a few rungs below leadership frequently lack the authority to greenlight a hire, may be out of the loop on which roles are actually being considered, and — perhaps most uncomfortably — might quietly view an ambitious newcomer as competition rather than a contact worth cultivating.
The better targets are the people actually shaping the budget and the org chart: a Head of Communications, a CMO, sometimes even the CEO at a smaller company. These are the people who know which problems the company is willing to spend money solving right now, and who control the purse strings for freelance or temporary work if a full-time role isn't on the table.
Reframe the Meeting as a Pitch
Talking to a senior leader instead of a peer changes the nature of the conversation itself. It's still an exchange of information — you're not walking in with a hard sell — but the mindset shifts. Show up thinking like a consultant: what does this organization actually need, and where do your skills intersect with that need?
Sometimes that means pointing them toward someone else in your network who's a better fit for a role you've spotted. Sometimes it's asking sharp questions that help the company articulate a gap they hadn't fully named. And sometimes, if you play it right, it means the two of you invent a role or project together that didn't exist before you walked in.
Make Yourself an Easy "Yes"
None of this works if your personal brand doesn't hold up under a quick LinkedIn search. Before a senior leader agrees to give you even five minutes, they're likely to glance at your profile — so it needs to make your value obvious at a glance: clear wins, clear skills, clear evidence you know their industry or client base.
The goal is to walk into that conversation already positioned as someone worth a leader's time — not just a name in their inbox, but a candidate whose value proposition is baked into every touchpoint, from resume to profile to the pitch itself.