Ask the Hard Questions

by Jordan-Ann Powell | Aug 29, 2017

Let me start off by getting something off my chest… I try to avoid conflict at all costs.

I love to make people happy – some might even say I’m a people pleaser. However, I often find myself in situations where I need to pull up my boot straps and face conflict head-on. And let’s face it: that’s typically the better thing to do in the first place.

It all starts with having the courage to ask hard questions.

As an account lead, I consistently deal with obstacles and challenges. I am often hesitant to ask the hard questions or say the hard things because it’s just easier to sweep those things under the rug. It may be easier to avoid the conflict and avoid the tough questions, but EASIER ISN’T BETTER.

Asking the hard questions (and getting answers to those questions) requires more time and energy, but it’s so worth it. And really, it’s better for everyone.

This is something that’s taking a lot of courage to commit to. If you’re like me, this is going to be a struggle. It helps me to make a few smaller goals to help accomplish a big one.

Here are a few things to help us get started:

1. Listen. That’s it. Listen. Listen without expectations. I can’t stress how important this is to close off your own inner-dialogue and listen to the person across the table. Hear their frustrations, fears, and hopes.

2. Empathize. Understand where the other person is coming from. This doesn’t mean you have to agree, but you can acknowledge understanding and compassion.

3. Ask 2 Questions. There’s always more to know. There’s always more to understand. Sometimes, these are the uncomfortable questions to ask — but after truly listening and empathizing with someone, they are likely to be received well and spark a great, meaningful conversation.

It’s not going to be easy, but what are the tough questions that you can ask this week both at work and in your personal life?