How to Ask Tough Questions at Work or in Life

At some point in your life, whether it be personal or professional, you are going to have to sit across from someone and ask them some tough questions.

When presented with these scenarios, you will generally not see everyone jumping into the pool to be a part of the conversation.

Many will shy away, some will be doubtful, and others will shrink into the background hoping not to be noticed.

It’s understandable because asking tough questions brings up emotions that make us question ourselves (despite whatever level of confidence we had going into the conversation).

Too often, we make the assumption that because the questions are tough, the answers will be equally tougher.

But this isn’t always the case.

When done correctly, asking tough questions can lead to a better outcome than originally intended.

Not because of the answers, but because of how we ask the question.

Here are 5 surefire techniques for how to ask tough questions more easily.

1. Be Direct

First and foremost, when asking a tough question, one must always be direct in their line of questioning.

Don’t engage in wishy-washy questions that take you five minutes to ask.

Focus on what you say and the answer you want to receive.

Be direct and on point, and use language that supports this train of thought.

No ‘shoulds’ and ‘coulds’, but rather ‘woulds’ and ‘dids’.

If there is a specific answer you’re looking for, direct the user to those answers by your line of questioning to find out what you need – don’t let them take you off-topic.

2. Be Prepared

In line with the first technique, you must be ready for what you are going to ask.

If this is a meeting that you have had time to prepare for, you must have the inquiries written down with you as a reference.

You might not get a chance to ask all of them, based on the conversation, but you must have them ready anyway.

We are all human and we all get flustered based on the situation at hand.

But being prepared is a great way to ensure that if you do get flustered by an answer, you have backup in case you need to bail out.

3. Be Honest

Tough questions are tough because they are seeking to find an element of truth.

Don’t engage in entrapment or other sneaky techniques to get the answer you want.

Be upfront and honest about why you are asking these questions and their content.

Being honest in a conversation where both sides are feeling the weight of the inquiry builds an element of trust.

It is then that both sides start to realize that the questions are not there to “get” someone, but rather, to understand the current problem.

4. Be Quiet

Do you talk or fidget uncontrollably when you are nervous?

It’s distracting.

But when you are quiet and focused, you immediately bring a level of calm to the conversation that was not there before.

Hopefully, this insulates the conversation from becoming a shouting match.

In the case of a conversation where the answers are coming loud and furious, this also has the opportunity to simmer it down and reduce emotions.

If you do need to fidget, hold your hands together so you prevent yourself from doing this.

When you do it the first few times, you might feel like you are holding yourself down.

That is a good sign.

It means it’s working and you need to keep doing it.

When we are quiet, our questions become measured and calm.

Plus, the other person immediately begins to focus more on our words versus the tone and volume.

5. Be Patient

As humans, we hate to see each other in pain.

So when asking a tough question, when we see someone struggling with it, we instinctively want to jump in and help.

While all the other points here seek to soothe tension, being patient aims to increase it as you wait for the person to respond.

It would seem like you are forcing the conversation on them.

It will create some awkward stares and silences.

But slowly, it will yield the answers and responses you seek as the other person is forced to look inward for a response.

This is good tension.

I have used this strategy a number of times when the conversation has become heightened and loud.

I watched as it diffused tempers, yielding answers you would have never thought possible.

The hardest part is stopping ourselves from jumping in and saving the conversation.

It’s key to remind ourselves that being patient is that we are not trying to save the conversation, rather we are trying to stimulate it.

Tough questions are a fact of life that you will never be able to escape

They are an inevitability as we continue to grow in our lives.

If the answer is worth the value and tension of making the inquiry, then the question must be asked.

Your goal should always be to ensure that your points or concerns come across clearly while ensuring you are getting the answers you need. 

Depending on the scenario, you might already be in a heightened mode of emotion.

So it’s key to ensure that you diffuse the situation as much as possible, so everyone involved feels calm, and secure, and communicates within a level of trust.

It is only when real conversation can begin.

Have you ever had to ask tough questions and it went better than expected?

What tactics did you use?

Let us know in the comment section!