There are times when you know you need to ask a question … even when you are pretty sure you don’t want to know the answer.

  • When is the right time to ask these questions?
  • Is there ever a right time to ask these questions?
  • Should you even ask these questions?

It’s easy to dance around the tough questions and fill the time with “other” questions. The bottom line is … there are tough questions you need to ask. They’ve always been hard. And until you have the answers … preferably by directly asking … you’ll have a harder time moving the relationship forward.

I’m talking primarily about work situations here, but the same thing applies to personal relationships. Whether it’s picking a college roommate without ever meeting them in person or online dating. There are plenty of tough questions to go around.

It’s Gotten Harder

These questions have always been with us, but they have become harder to ask in this modern age where we don’t always sit across the table from someone and have the chance to look them in the eye.

Whether you are building a relationship with a co-worker, developing a partnership or seeking to advance your career there are questions you will need to ask.

Of course, there are a lot of questions we need to ask on a regular basis. Some are just to get the job or get your job done, to understand something or to clarify your thinking.

Some questions are easy

  • Asking for the job
  • Asking for the order
  • Asking for recommendations

Some questions are hard

  • Asking what it will take to get to the next level
  • Asking to go over someone’s head
  • Asking someone to do a potentially unpalatable favor

Everyone has challenges with different questions. Every situation is different. The point is … you just need to ask the tough questions.

Why Ask The Hard Questions?

The main reason why is because you really do need to know. As hard as it may be to ask. You need to do it. The upside is … Once you get the hard questions out of the way the relationship can move forward.

One interesting corollary to asking tough questions is that you might determine there is no synergy and no need to move the relationship forward.

The flipside of this is … What if you NEED to move the relationship forward? Then you’ve got a dilemma.

Ask the Questions

As hard as it may be, and no matter what the situation is, there are times you just need to ask the tough questions. The old adage of “There are no dumb questions” does apply here. The risk is that you end up looking foolish or exposed in a way you did not expect. The risk of not asking these questions are worse.

So, Ask the (tough) Questions. You’ll be happy to know you did. The other party will be happy you did too. Because they also know the tough questions need to be asked.

How have you handled the hard questions?

  • What are the hard questions you know you needed to ask, but didn’t?
  • What hard questions did you ask?
    • Did you get the answer you expected?
    • Did you get a completely different answer?
    • A better answer than you expected?
  • What advice would you give someone to help them ask the hard questions?


Jeff  is a veteran in the Enterprise Content Management industry. Over the past 20 years he has worked with customers and partners to design, develop and deploy solutions around the world. Jeff is currently the Director of Strategic Alliances at Winshuttle. He has worked for Microsoft, FileNet (IBM), K2, Captaris, Open Text, Kofax and Kodak. He speaks and blogs about ECM and the Intersection between Social, Mobile and Cloud Computing.