Signal high competence to the program manager by asking these questions

Program managers (PM) have a hard job.

Your job as an aspiring 1099 is to show you can make their lives easier.

When you talk to a PM, your goal is to figure out what their pain points and demonstrate how you can solve them.

But, simply asking smart questions that show you are listening and understanding their problem goes a long way.

You want the PM to think "this guy gets me!"

It'll soften up the PM to a favorable 1099 arrangement.

  • Who is the primary customer you work with? [Get detailed: Which office? Which program? Which GPOCs?]
  • What kind of initiatives or programs is the customer focused on? [Customer and client priorities end up becoming the PMs headache]
  • What specific areas of the program are you helping the client with? [You may think the PM runs a contract that helps with X but actually does Y type of work]
  • Has it been smooth sailing or have there been some challenges? [This will help you gauge what the PM really needs help with.]
  • How urgent is it to get someone to fill this position? [This will reveal more detail about how much leverage you have to go 1099. If they need someone yesterday, then you have leverage. If they are like "meh we can wait" then that's not great]

If you do your homework and ask specific questions that really get to heart of the PM's problems, you will appear super competent and be in a favorable position to land a 1099 gig, even before telling the PM how you can help!


If you have questions feel free to reach out to me directly at I can also add you to my informal mailing list in case I have updates or news or whatever.


I write a lot about getting to, talking to, and negotiating with program managers  in my book.

You can read more about it here:

Going 1099: How to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time

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