Do you want to achieve your goals? Then you MUST ask yourself the right questions

Carson Young
Driven By Questions
7 min readJan 2, 2018

The success of any goal is dependent on the questions you use to set and evaluate that goal. If you truly want to achieve your goal, take a minute to stop and understand the questions you will use to make that possible.

Goals are based on situational questions. Every situational question ever asked has an element of either reflection or progression. Understanding this and using it to your advantage will help you get better at achieving your goals.

When we ask a situational question we are trying to understand and evaluate something that has already happened.
eg: I feel like I wasted a whole day yesterday…What did I actually accomplish?

OR

We are trying to decide on a direction that takes us where we want to be.
eg: I want to earn six figures by the end of this year…What has to change for that to happen?

It is unlikely you will set a goal to change unless you are unhappy with how things are currently. It’s also unlikely that you will set goals if you don’t have a dream of achieving something new in the future. Until you pause to ask the questions about how satisfied you currently are or what you want to change moving forward, you will likely just continue at your current pace.

Imagine a business department that has had diminishing sales for the past six months. If the sales manager doesn’t ask why sales are declining and only wants to hear lofty projections of what could happen to get back on track, they are likely going to miss the root cause of the problem and continue to suffer. If however, that sales manager only looks backward to ask what’s causing the downward trend but doesn’t ask how to fix the problem moving forward, they will see the business crumble and fail.

Asking questions to understand the past only matters if you care about changing the future.

Photo by pan xiaozhen on Unsplash

There are those who say studying the past is most valuable because learning from the experiences of others and ourselves will allow us to chart the path of our future.

Study the past if you would define the future.
Confucius

While others say that focussing on the future is what truly matters because there is no way to change the past.

We are made wise not by the recollection of our past, but by the responsibility for our future.
George Bernard Shaw

As with so many other things in life, finding a good balance is what matters. Too much of one approach will certainly create missed opportunity in the other direction.

Understanding the differences of these reflective vs progressive questions, will help us develop and work toward the right goals as well as evaluating our progress over time. This article will help you determine when to use questions that direct our attention forwards or backwards when it comes to setting goals. To do this, we’ll stop focussing on goals and focus directly on questions for a minute.

Progressive Questions can be used to set goals and chart a clear path. They help us look forward with a purpose.

At the end of each day I like to ask myself “What is the most important thing I want to accomplish tomorrow?” and record my response in a journal.

This progressive question makes me think about my priorities for the coming day. When I wake up the following day I have something important to work toward rather than getting sucked into emails and ‘fires’ that need put out. I also know that if I accomplish that item I’ll have a good response to record for my reflective question at the end of the next day.

Great progressive questions often need a followup question to clarify the path desired. They will start broad and then get narrowed down through a series of focussed questions. Using examples from a business setting is the most effective way to demonstrate how progressive questioning can work.

The vice president of sales will be asked what the annual revenue forecast looks like. To get this number he would ask each of the managers beneath him what their teams can add to the revenue projections. Those managers need to be asking what performance their teams must produce each day to not only maintain, but increase their current sales numbers. It is easy to see that if the VP simply threw out a big number without asking the supporting questions, he could very easily give an inaccurate forecast.

Photo by Zach Miles on Unsplash

A more personal version of this example may sound more like “Where do I want to be ten years from now?” Although everyone will have a different answer, and the exact milestones required to achieve that goal may not be stupendously clear, anyone that truly has a ten year goal certainly has to use milestones to get there. After using questions to determine your high level goal you need to ask more questions to break it down into smaller milestone goals. The question to develop those milestones might look like: “What can I do this week/month/year to get closer to my ten year goal?”

When we ask a situational question we are trying to understand and evaluate something that has already happened, or we are trying to decide on a direction that takes us where we want to be.

Reflective Questions can be used to establish a baseline. They help us stay grounded (in business or personal matters) by evaluating progress over time to ensure we are not slipping backwards.

Another question that I ask myself and record in my daily journal is “What is the most important thing I accomplished today?”

This question helps me pause and consider the activities I chose to spend time on that day. If nothing stands out as truly valuable or important, I am motivated to focus on a better use of time the next day.

In my business I regularly run reports to answer questions such as “How many new client projects did I launch this month?” and “How does that compare to the previous month?”

By looking back at this trend over time I can easily quantify whether I need to expend more efforts acquiring new projects or if my current efforts are adequately moving the needle.

On a daily basis it may seem that the answers to such reflective questions are inconsequential. It is important to regularly make time to gather our answers from a period of time (such as monthly or quarterly) and reflect on those results as a whole. I call these sessions ‘elevated reflection’ because you are looking at responses with a new high level perspective rather than the daily ‘in the weeds’ perspective. I promise you will be surprised at how clearly trends pop out when you group together daily reflections and read them with a wider perspective. During these sessions of elevated reflection you can learn hidden truths about your habits and motivations.

It is not uncommon to be surprised (maybe even disappointed) with the answers you uncover when asking reflective questions. One of the easiest things to do is justify those answers to explain away any undesirable results. It is important NOT to add justification to reflective answers. If you don’t like what you find, then it is time to ask a follow up progressive question about how you will change that result moving forward.

A great example of this came up during my monthly budgeting as I ran the report on how much gas money my wife and I had spent:

“$150 over budget in November?! Well that’s because we went to visit your parents for Thanksgiving.”
“In October we were almost $150 over as well…but that month we had an extra trip out of town for work.”
“September was over budget, but only because of the vacation we took that month.”

While I may tell myself that each of these months had a special circumstance to justify going over budget, the reality is that I regularly spend more than planned on gas money. I either need to limit trips and stay within the allotted amount, or get realistic and adjust my budget to spend less on another category to accommodate for my true gas needs.

Taking time to ask the question and reflect on how much I spend for gasoline each month is absolutely useless if I do not intend to take action and adjust my plans based on the answer I find.

We can learn from history, but we can also deceive ourselves when we selectively take evidence from the past to justify what we have already made up our minds to do.
Margaret MacMillan

When we ignore answers or choose to interpret them with some amount of justification, then asking in the first place was a waste of time. This is true for all reflective questions. Asking questions to understand the past only matters if you care about using the answers to change the future.

Asking questions to understand the past AND setting goals for the future will only matter if you care about changing the future.

Start this new year by asking some progressive questions to determine where you’d like to go. Also make sure to think ahead about what good reflective questions you will use to measure progress during this pursuit.

If you aren’t going to ask the right questions, don’t waste your time dreaming up a goal that is doomed to fail.

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Carson Young
Driven By Questions

Co-Founder of Driven By Questions publication. Dedicated husband, entrepreneur, & lifelong learner. Passionate about communication.