How to WOW Your Boss: 4 Miracle Questions

February 20, 2013

I don’t know your boss, but I know exactly what he/she wants from you—to make his/her life easier.  There’s nothing a boss hates more than to feel as though an employee is one more thing that she has to manage.  One of the simplest ways to get “out in front” of your boss is to proactively set useful review meetings with her.  First, put in a simple request if you don’t have these meetings on the calendar already; I’d like to schedule 30 minutes every 1-2 weeks to update you on my work and get feedback from you.  Often at this point you’ll see hesitation on your boss’s face.  Usually that’s because she’s not sure it’s a good use of time.  She has so many ineffective meetings on her calendar that she shudders at the thought of adding another one.  At this point, assure her that it will be a good use of time.

Now, make good on your promise.  The day before the meeting, spend 30 minutes answering the following four questions:

  1. What were my successes since we last met?
  2. What have been my challenges since we last met?
  3. What’s my focus for the upcoming week/month?
  4. Where do I need support?

Then structure every meeting around these 4 questions. Be clear and to the point with your answers.  When you’re done, ask for any thoughts/advice.

The beauty of these questions is that they force all sorts of productive behaviors.  You get clearer on what success looks like because you and your boss are defining it together regularly.  You get real-time performance feedback (not 1-2 times/year which is essentially useless for behavior change).  You’re proactively planning your work.  You’re asking for targeted help.  You’re strengthening a key relationship.

Be prepared. Be focused. Be authentic. Be inquisitive. It gets easier and more effective the more you do it. I promise it will WOW your boss, if for no other reason than so few people do it.

Are you using this sort of approach already? Please share your stories below for others to see.

–Doug Sundheim

P.S. With a slight tweak of the questions, you can use this approach to WOW clients too.