Ask the Hard Questions

Jordan Ann Powell

By Jordan-Ann Powell

Aug 29, 2017
Updated: Nov 20, 2025

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?

 

ask2

Jordan Ann Powell

Post by Jordan-Ann Powell

Jordan-Ann leads client strategy and services at Syrup, helping B2B brands connect every dot between vision, audience, and impact. She thrives on helping businesses see the bigger picture: what’s working, what’s not, and where to go next. Known for her calm clarity and commitment to doing things right, she brings focus and connection to every partnership. When she’s not guiding clients toward the next big idea, you’ll find her running trails, spending time in the community, or planning her family’s next adventure.