The person who has your back

A wingman can help your career take off.

In jet fighting, dating, and AA, you’re more successful when you have a wingman.  A person that has your back, checks up on you, and will help get rid of enemies if needed.

With everything you want to accomplish, wouldn’t it be great to have a wingman for your career?  It’s so easy to get excited about all the great plans you have only to run out of steam on some of them and completely abandon the rest. You need someone to help you stay focused. You need someone to keep you on track.  You need an Accountability Wingman.

What exactly is an Accountability Wingman?

An Accountability Wingman is someone you share your plans with and then promise you will follow through with them.  You know how it’s so easy to blow off promises to yourself?  Yet, when you promise someone else, you are much less likely to blow them off.  Same concept here.  Just by putting your plans out there – somewhere beyond the inside of your head – it makes them that much more real. And what happens if you start to slip? You can’t pretend you never made your plans because your Accountability Wingman will nicely, but firmly, let you know.  Because of them, you are accountable to someone other than just yourself.   Whether it’s completely finishing your LinkedIn profile, publishing an article in an industry magazine, or getting your side business started, it’s a lot harder to blow off it when you’ve told someone else.  Because now it’s out there and you are going to look like a flake if you don’t follow through.

How to choose an Accountability Wingman (AW)

While committing your plans to almost anyone will help you follow through, some AWs are better suited for the job than others.

Here’s what to look for:

  1. Someone whose opinion you respect and you would hate to let down
  2. Someone who is responsible and punctual
  3. If this person asked you to be their wingman, you would gladly say yes

Here’s what you don’t want:

  1. A spouse or significant other. (It’s almost as easy to break resolutions with a spouse as it is with yourself)
  2. Someone with a crushing work schedule
  3. Someone who is always late

What to do before meeting with your AW:

  1. Write down exactly what you want to get done in the next two weeks. Be specific
  2. Map out all the milestones and deadlines
  3. Figure out how you want to be accountable.   A daily update via email? Text? A phone call?
  4. If you miss a deadline or update, what do you want the consequences to be? A gentle email from your AW? A smack on the nose with a rolled up newspaper?  $10 into your AW’s PayPal account?
  5. Think of your backups to keep you on track. Outlook calendar reminders to send in your update? An alarm on your phone?

How to ask and work with your AW:

  1. Briefly explain what an Accountability Wingman is (email this link if you want) and point out how they have all the sterling qualities of a good one and you would be honored if they would be yours
  2. If they agree, set up a time to go over your plans and system for updating
  3. Get their honest feedback on your plans. Are they clear?  Do they seem too vague? Too ambitious?  What suggestions do they have?
  4. Are they kosher with the update system? Once again, get their feedback and suggestions.  Do this throughout the process

What to keep in mind:

  1. Your AW is not your mother, your shrink, or babysitter. Do not put them into a position where they ever feel like they have to nag you or take advantage of their generosity
  2. Once you get in the habit up of sending an update, it gets much easier
  3. When the two weeks (or however long you gave yourself) are up, do a post mortem and figure out what would improve this process next time
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