I sometimes wonder, where I may have been if people were more open to asking difficult or tricky questions of me. This post is not about regrets but more on general curiosity. Professionally, we all present a cover of ourselves in order to fit a generally acceptable mold. When you are getting to know people in these settings, there are all the formality and midwest-niceness that occurs. But we often let things that bug us, concern us, or stand out left aside, which prevent us from really getting to know one another. So, back to my ponder – I wonder what sort of relationships I would have if people just simply asked a difficult question.

I was once an independent contractor. And it did not work out for a myriad of reasons – one possible reason is because I started, said business, in the middle of a global supply chain crisis (not the best of timings). But there are certainly other things I take full ownership of. And what I have come to learn since ending that, is that people are more or less afraid to ask me, what happened? What does this mean? Etcetera.  

I get it – difficult questions can be challenging, especially if you are concerned about causing offense or receiving an unfavorable response. But the truth can be enlightening. And if your only truth is one-sided, can you really take it to heart? Long ago, I was told to read the book ‘Crucial Conversations,’ and I wish more people have. I also wish I used these tactics more.

Here are some of my tips on how to ask difficult questions in a professional and respectful manner. This is how I wish I would be more approached on my work history:

• Be clear and specific: Start by being clear about the question you want to ask. Make sure the question is specific enough to elicit a helpful response.
• Use a neutral tone: When asking difficult questions, it’s important to use a neutral tone of voice and avoid sounding accusatory or judgmental. Stay calm and composed, even if you’re feeling frustrated or upset.
• Provide context: Providing context for your question can help the other person better understand your perspective and why the question is important. This can also help prevent misunderstandings or misinterpretations.
• Focus on the facts: Stick to the facts when asking difficult questions, and avoid making assumptions or jumping to conclusions. Present the information objectively and try to avoid confrontational language.
• Listen actively: When asking difficult questions, it’s important to listen actively to the response. Take time to understand the other person’s point of view and ask follow-up questions if necessary.
• Offer solutions: If appropriate, offer potential solutions or suggestions to address the situation. This can show that you are genuinely interested in finding a positive outcome.

Remember, it’s important to approach difficult questions with professionalism, respect, and an open mind. By doing so, you can foster constructive dialogue and find ways to address any issues that may arise.

Just ask,

Nate Regina