I talked to a person at a company today about trainings for our state agency. I realized that I had been talking to the Exec Director of said company. After researching their website, it does not seem like they have an assistant. Would it be too awkward if I email the Exec Director from my personal email to ask if they need an assistant?

2 Comments

1. Paulla Fetzek, MSEdOctober 28,2026 at 1:18PM UTC

   Hello!

   While you didn't mention directly, from your email do I take it you like this person? As I'm sure you know, working with someone and working for someone aren't the same thing.

   As for contact - I'd reach out to the HR or Hiring Department of the company this person works for an inquire if such a position exists. It may be someone fills that role but doesn't have that specific title. And it may be the Exec Director doesn't want one.

   All the best!

2. Steven MockNovember 7,2026 at 5:05AM UTC

   Not awkward at all if you keep it short and professional. I'd reference the training conversation so they remember the context, and say something simple like you noticed they may not have support in that role and you'd be glad to help if they ever need an assistant. If you can, use your work email rather than a personal one — it reads more credible and keeps the boundary clear. And frame it as an open offer, not an application for a job that may not exist yet. That way there's no pressure on either side.