Unawkward icon

Unawkward

Manager Coaching

Say it out loud before you have to. Then hear what to say instead.

A rehearsal room for the conversations that come with managing people. An AI plays the other person, you speak out loud, then coaching quotes your own words back.

  • No account
  • Rehearsals stay in your iCloud
  • 7-day free trial
Runs on
iPhone
Speaks
English
Unawkward screenshot: Home screen with upcoming conversation and Rehearse button, captioned “The conversation you keep putting off”

Nobody teaches you how to manage people. You usually find out you are bad at a conversation while you are in the middle of having it.

Unawkward is a rehearsal room for the difficult conversations that come with managing people. You describe the situation, and an AI plays the other person. They defend, they deflect, they go quiet, and they do not fold just because you were polite. You speak out loud. They answer.

Then it tells you what to say instead — about the conversation you actually had, not managers in general.

Unawkward screenshot: Rehearsal chat transcript with suggestion chips, captioned “Say it out loud, before you have to”

Rehearse out loud

  • You talk, and the other person talks back in real time
  • Rewind a moment that went wrong and take it differently
  • See where the other version would have gone
  • Feedback that turns into an argument, a slipped deadline, saying no to your own boss — or describe your own
Unawkward screenshot: Rehearsal transcript with turning point and two branches, captioned “It forks when they push back”

Coaching that quotes you back

  • What worked, the hard moment, the turn, and one thing to change
  • Each point fixed to a timestamp, in your own words
  • “Change one thing” comes with an actual sentence to use
  • Say how prepared you feel before and after, and watch the gap
Unawkward screenshot: Debrief with suggested line and what worked, captioned “Not a score. The actual words”

Ready for the real one

  • A prep card for the ninety seconds before: your opener, your non-negotiable, one tactic
  • What to say if they push back
  • Allow calendar access and it picks out the meetings worth rehearsing first
  • Only meeting titles are shared, and you can turn it off
Unawkward screenshot: Prep card with opener, non-negotiable and tactics, captioned “Ninety seconds before you walk in”

Private by default

  • No account — you never give an email address
  • Rehearsals stay on your iPhone and in your own iCloud
  • Each rehearsal is processed by an AI service, then discarded
  • Practice, not advice: not HR, legal or medical guidance

Screens

Select one to see it full size.

Available in

  • English

More information