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How To Ask Brilliant Questions To Make Smart Decisions


How To Ask Brilliant Questions To Make Smart Decisions

Have you ever wondered if I would have only known then what I know now? It makes no difference who you are, this has happened to you. It’s happened to me. No one escapes this feeling at some point.

Sometimes, the choices you made resulted in little owies. Other times, I’m sure it was much more painful.

Regardless, any time you’ve made a poor decision, at least one of two things was wrong. You either had a faulty decision-making process or you didn’t have accurate or complete information.

Even if you have the world’s greatest decision-making process, nothing other than pure luck can overcome a lack of information when making your decisions. Sure, you can blindly get lucky, but I certainly wouldn’t want to take that chance.

Today, I’d like to talk about how to ask brilliant questions to make smart decisions. The techniques I’ll run over can apply to anything in your life, but I’m going to concentrate on the business world, especially as it relates to job interviews and making sound career decisions.

All good things come in threes.

Anytime you’re asking questions in a job interview or questioning someone as it relates to business, you can prepare yourself by first asking three questions:

  • What do I want to know and why is it important to me?
  • How will I ask it?
  • How and when will I use the information?

As it relates to these three questions, what I’ve noticed is that most people (for whatever reason) spend way too little time on the first question of what they want to know and virtually no time on why they want to know it.

They spend even less time determining exactly how they’ll ask the questions. And, very few consider the strategy of when they’ll use the information. That’s when—as in a specific moment in time—they’ll use the information to their advantage.

Not to stray from our focus today, but I’ve written several articles about the many great benefits you can realize from asking questions. I’ve included some show notes to articles you can check out to see how to sell yourself, show your organizational skills, and demonstrate passion and interest. Of course, you can always grab Interview Intervention, which has loads of insight on these topics.

But, I want to focus primarily on how to ask your questions to gather information to make great decisions (perhaps career decisions).

First Question: What do I want to know and why do I want to know it?

Now, the first question to ask is, “What do I want to know and why do I want to know it?”

You must know what information you need to gather and why it’s important to you. When you’re evaluating a job change, the best place to start is your requirements. I spent considerable time in an earlier podcast titled The First Thing To Do When You Want To Change Careers speaking about your “whys.”

Your whys are such great places to start because that’s what you care about! Why would start in any other place?


Second Question: How will I ask it?

Before I get to how to structure your questions and those other benefits, there’s something really important to understand.

Your goal in a time compressed situation such as a job interview or a business meeting is to gather as much accurate information in the least amount of time. You do not want to run the risk of wasting time or getting insight that, while nice to know, isn’t necessary for you to make the best decision for you or your company.

If you ask a poorly designed question, you not only run the risk wasting time but also not getting the information you need. There’s also a domino effect because you’ve now burned up time you needed to ask additional questions.

Here’s why. When two people are speaking, in any situation, you have biases that were formed from your life experiences. These biases cause you to interpret words and gestures in a particular manner. There are natural communication gaps. There are distractions. All of these issues make it difficult for you to accurately exchange your message with another. Without diving too deeply into this commotion, realize these issues are present.

I’m sure you can think of many situations where you’re speaking to another. You thought you said something clearly, but the other person misunderstood you. This isn’t much of a stretch.

When you ask job interview questions, you could put the interviewer at risk of not providing the information you need if you ask a poorly designed question.

I consider a poorly designed question to any question that leaves interpretation for why you want to know what you want to know.

Here’s an example: Let’s review two job candidates to illustrate the point.

The first candidate, a senior executive, is interviewing with a human resources executive for a technology consulting firm.

The second candidate is a professional services software developer interviewing with the same HR executive. Both decide to ask the same question, but for two entirely different reasons:

“Can you please describe your client portfolio?”

The senior executive is interested in whether there is sufficient balance between industries and clients to ensure the company remains healthy in the event a significant client leaves or there is an economic downturn in one of the industry sectors.

The software developer wants to understand the different types of clients and their locations because she is interested in understanding which sectors she’ll be supporting and where she will likely travel.

How will the interviewer know how to answer the question?

Rarely will the interviewer clarify the question with a response such as, “Why is that important to you?”

Most people will make an assumption regarding why you want to know. Their assumption will default to why they would want to know that information.

More often, she will simply start speaking and provide superfluous information you find unimportant for your needs or decision process. Consequently, you waste time.

Instead, I’d encourage you to position the interviewer in advance to narrow her response so she can address your most pertinent needs. For example:

Senior Executive: “Can you please describe your client portfolio? I’m interested in understanding your current distribution because I want to ensure the organization is financially balanced and stable in the event we lose a client or there is a sector downturn.

Software Developer: “Can you please describe your client portfolio? The reason this information is important to me is that I want to understand the types of companies I would consult for because I have more experience implementing solutions in some sectors than others. That will also provide me with a sense of where I’m likely to travel.”

Adding your rationale at the end is the key to getting the insight you want as quickly as you can possibly get it. The sooner you get the information you need, the more time you create to ask additional questions.

[I mentioned Interview Intervention earlier. In the book, I spend a lot of time breaking down all the benefits you can gain from asking well-structured questions. It’s my belief you can optimize your questions so you are selling yourself and also gathering the insight you need. So check out the book. I give it away free if you join my Tips for Work and Life BlogClick here to get the book from the milewalk Academy!]


Third Question: How and when will I use the information?

Think about your job interview. One of your goals is to sell yourself and another is to gather insight to make a good career decision. That means, some information you gather during the session needs to be used immediately and some can be contemplated.

I call this short-term and long-term use of the information.

Any question you ask that yields information you can immediately use to sell yourself or make a decision is short-term.

Any question you ask that yields information you’ll ponder is long-term.

Let’s take a look at a few examples:

Short-Term/Role-Related: “I was wondering whether you could share what you consider the qualities and characteristics of the most successful individuals on the team I’d be joining. The reason I’d like to understand this is to ensure that I would fit well with my potential teammates.”

The interviewer will now highlight those characteristics for the candidate. You, in turn, can make notations of these qualities, which are essentially what the company wants to duplicate and hire. You now knows the type of person the company seeks and can use this information during that interview as well as subsequent interviews to craft responses that illustrate how you possesses those qualities.

Long-Term/Role-Related: “I’d like to get a better understand of the career development and longer-term job opportunities I might have. There are a few areas which interest me, and I want to determine whether I’d be putting myself in a position to realize that a few years from now.”

This type of information is something you can contemplate after the discussion.

So, I hope you’re getting the picture that asking great questions that lead to great decisions comes down asking yourself a few key questions. It also comes down to:

  • The quantity of your inventory of questions (What will I ask?)
  • The quality of your inventory of questions and their alignment to your needs (Why is that important to me?)
  • Their structure and effectiveness in yielding the information you want as opposed to what the other party thinks you want (How will I ask it?)
  • The benefit of knowing the information (How will I use the information?)
  • When you will use the information (When will I use it to make a determination?)

As always, I love to hear from you: What are your best question-asking techniques?

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