Business Problems and Solutions

Ask the Right Questions: 2 Problem Solving Questions that Make the Difference

To solve a problem, we need to understand the root cause, then define and deliver a solution. And that starts when you ask the right questions.

Detective Spooner pauses, rethinks, and asks a more direct question of the hologram.

“That, detective, is the right question.”

Solving business problems is the same – without the killer robots and murderous subterfuge. We need to ask the right questions to get to the heart of the problem and understand what to do next. While asking the wrong questions leads to erroneous conclusions and moves us away from the goal we are trying to achieve.

This article shares the impact of asking the wrong questions, explains what the right questions to ask are, and provides a practical demonstration of the power of asking the right questions.

Here’s what you will learn:

The Impact of Asking the Wrong Questions

A few years ago, I experienced the lows and highs of an emergency room visit when someone dear to me suffered life-threatening complications from a recent surgery.

The good news: the doctor and nurses who worked with the patient were skilled, reassuring, and each did their part to ensure a positive outcome. But among the competence and poise was a broken tool that could have led to a disastrous result. The hospital’s blood tracking software.

The software tracks the prescribed blood from hospital lab to patient and prevents the wrong type being given – which can cause symptoms ranging from a severe flu like reaction to death. It works by scanning the barcode on the patient’s wristband, the barcode on the bag of blood plasma or platelets, and compares the details in the system. If it’s a match, the software approves the transfusion. All within a handful of mouse clicks.

However, it took the Senior Nurse and his cohort three escalating support calls, scanning seven barcodes (two on the patient, five on the bag of plasma), and 20 minutes before a software support technician – far from the hospital – could override the software and approve the transfusion in the system.

As a Senior Project Manager in Software Development, I watched the spectacle with a morbid fascination. What was the problem the software was trying to solve? What inputs did it require? How did the end-user behave when the software didn’t respond as they expected?

Part way through the 20 minute battle, rather than wait for the software’s approval, the Senior Nurse manually began the blood transfusion. To me, this was a wonderful example of how to never lose sight of your goal, no matter what is happening around you.

Clearly, the software team asked the wrong questions during the design phase. Or nobody asked the right questions. Two critical impacts from this was the system was unable to handle multiple barcodes (a common scenario in hospitals) and universal O-negative blood being given to an A-negative patient (a standard transfusion combination).

What other issues were there because of the 20 minute trip to the Twilight Zone?

  • Did the Senior Nurse miss his scheduled break and continued his shift tired and frustrated, leading to an increased chance of mistakes in the care of other patients?
  • Was this the night the Senior Nurse quit, driven to leave his vocation by critical software that didn’t work?
  • What if it was a new nurse, fresh from training, responsible for the transfusion? If they didn’t start the transfusion until after the software gave the all-clear, what would that 20 minute delay have done to the patient who needed the blood?

The effects of asking the wrong questions range from the straightforward – financial impacts – to the insidious – low employee engagement and high staff turnover – or worse.

So, what are the right questions to ask?

The Right Questions to Ask When Solving Problems

Black lab puppy chewing on a dog toy, looking at the camera while the dog's owner tries to take the toy away
Asking the right questions encourages the right behaviours. Photo by Camylla Battani on Unsplash

To understand the business problem we are working to solve, we need to research both the objective and subjective forces behind the problem. How people are performing their work and why they are doing it.

The right questions get us answers to the physical and behavioral reasons behind people’s actions and motivations.

The right questions to ask are:

  • How can I encourage people to… insert desired behavior?
  • What barriers do I need to remove for this to happen?

For example:

  • How can I encourage customers to buy my product or use my service?
  • How can I encourage my team to follow my leadership?
  • How can I encourage my website visitors to follow through on my calls to action?

And for each encourage question ask, What barriers do I need to remove for this to happen?

Additional Reading in The Become a Better Problem Solver Series

How the Encourage/Barrier Questions Work

Two tone terrier dog staring at the camera
The right questions are memorable, easy to use, and get you the right answers. The questions tell us what we need to do and the answers tell us how to do it. Photo by Justin Veenema on Unsplash

Combining Strategy and Action into a Single Question

How many strategic plans, crafted with care and presented with passion, fail because of poor execution? The problem lies in the lack of solid ground between proposal and action. There is no mechanism to transform the strategic goal into executed results.

What makes the encourage/barrier questions different and powerful is they are both strategic and actionable at the same time.

The questions help us understand what we need to do, and the answers tell us how to do it.

Iterating through the answers is how you add details and actionable steps to the plan the questions create. In the business world, especially project management, this is called decomposition. Which is a good thing. The complete opposite of when decomposition is a vital clue in a police procedural TV show.

Iteration and decomposition help you create solutions with clear and actionable activities.

A rule of thumb for iteration

  • The bigger the problem or the more vague it is, the more I iterate
  • The clearer the problem, the less I iterate

An example of strategic questions that generate actionable answers

You want to improve your project delivery and make your project management process more efficient and less burdensome. A top-notch plan.

Part of your strategy involves correcting the requirements gathering process. You want to stop returning to your stakeholders to find out their needs, like an annoying notification that won’t go away. The current results of this inefficient back and forth are scope creep and cost overruns.

How can I encourage my stakeholders to provide an accurate list of the things they need?

  • Make it easy for stakeholders to provide their needs.
  • Build trust to encourage collaboration between the sponsor, stakeholders, and project team around technical and business priorities.

How can I encourage myself and the team to make it easy for stakeholders to provide their needs?

  • Provide easy-to-use documents and feedback submission processes.

What barriers do I need to remove for this to happen?

  • There is a high paperwork burden when filling out forms and project documents.
  • The questions asked are ambiguous, leading to vague answers, nor do the questions cover every aspect of the stakeholders’ jobs, which results in vital information being omitted from their answers.

Your strategy is to:

  • Improve the requirements gathering process.

The action steps are:

  • Create documentation that is clear and easy to use.
  • Ask the right questions when interviewing stakeholders.
  • Ask the sponsor and key stakeholders to confirm priorities.

Which results in:

  • An accurate list of requirements.

Intentions, Results, and Usage

When you ask the right questions – how can I encourage people and what barriers do I need to remove – you get the right answers. Which enables you to solve problems with the right solution.

The result of asking the right questions is an actionable plan to increase engagement, reduce frustration, build trust, lower waste, increase productivity, and resolve whatever category of problem your problem falls into.

The questions can solve a distinct dilemma, such as increasing end-user engagement for an app, or provide a roadmap for broader professional development, such as improving one’s leadership skills.

Ethical influence and leadership is the idea that your positive behaviours encourage people to trust you. To grow that trust, the encourage/barrier questions help you determine which behaviours to adopt and to how to put them into action.

The Right Tool for the Job

The right time to ask the encourage/barrier questions is when solving a problem that requires a change in behaviour.

For example, increasing conversion rates on a landing page, improving the quality of work the team produces, or reducing employee dissatisfaction.

Preventing Blind Spots in Your Thinking

When you ask how can I encourage people and what barriers do I need to remove it sounds as if they give the same answer. After all, if you encourage your colleague or client, aren’t you removing existing barriers? Well, not quite.

The encourage/barrier questions provide different perspectives to the problem by defining positive behaviours and highlight the negative impacts of assumptions and unknowns.

Imagine a fantastic carrot cake with the finest ingredients. When it’s baked, no-one can resist it. Which is what you want – you encourage people to buy it, eat it, and come clamoring back for more.

Slice of carrot cake on a plate with a fork
Photo by K8 on Unsplash

If we don’t consider the barriers that prevent the world’s best carrot cake from being created, we risk the following conversation:

“Did you bring the fresh eggs from the chicken coop and the unbleached flour?”

“I did. You get the carrots from the farmer’s market?”

“Yep. By the way, why are we doing this outside?”

“Because I thought it would be fun!”

“How are we going to bake the cake?”

Language is Important

Language matters because our behaviours are sneaky and sabotage us when we want to change.

Profile shot of a brown and white husky with bright blue blue eyes
The Husky – nature’s loquacious and dramatic, but lovable, four-legged manager. Photo by Ilya Shishikhin on Unsplash

If the manager repeats, I must stop talking over people, all the brain will hear is I must talk over people. And what happens? The ingrained habit takes over and nobody in the meeting gets to speak. Which is no surprise to anybody.

The language in the questions helps us look towards where we need to go.

Picture a galloping horse, snorting, charging, and kicking its way around the field. You’re on its back, thigh muscles gripping the saddle like your life depends on it. You see two gates, fast approaching. One is open, the other closed. You focus on the closed gate. “Don’t hit it, don’t hit it.” You repeat.

Therefore, an important behaviour to perform, while not holding the reins in a death grip, is to face the way you want to go. Towards the open gate.

The same applies to problem solving.

When our loquacious manager says they, must not talk over people, they’re looking at the closed gate. Disaster beckons.

The right question to ask, and the one that points toward the open gate, is how can I encourage myself to listen to my team in meetings?

Our effusive manager identified a barrier – talking over people – when evaluating why his team was reticent in meetings – how can I encourage my team to speak up? Because of the iterative nature of the encourage/barrier questions, the manager identified a behaviour he can change – to listen more.

Recap: The Power of Asking the Right Questions

The right questions get us to the root of the problem we’re working to solve. They help us understand the reasons why people do what they do and how they do it.

The Right Questions to Ask Are:

  • How can I encourage people to… insert desired behavior?
  • What barriers do I need to remove for this to happen?

The Encourage/Barrier Questions Are the Right Questions to Ask Because…

They are iterative:

  • You ask the question and get an answer. Then ask again, using the previous answer as the subject of the new question.

They are the right tool for the job

  • The right time to ask the encourage/barrier questions is when solving a problem that requires a change in behaviour.

They prevent blind spots in your thinking

  • The encourage/barrier questions provide different perspectives to the problem by defining positive behaviours and highlight the negative impacts of assumptions and unknowns.

They are strategic and actionable

  • The language in the questions helps us look to where we want to go.
  • The questions help us understand what we need to do, and the answers tell us how to do it.

The encourage/barrier questions are so powerful because when you execute on the answers, you develop behaviors that positively impact everything else you do.

For example, how can I encourage clients to provide an accurate list of the things they need, leads to:

  • Building relationships
  • Creating easy-to-use processes
  • Encouraging collaboration

And those helpful and encouraging behaviours, when done consistently, become a habit. Specifically, a keystone habit.

The next article in the Become a Better Problem Solver Series, Develop the Be Helpful Keystone Habit, explains what a keystone habit is and why they are so potent.

Bonus: Practical Example of How the Encourage/Barrier Questions Work

Imagine you’re the project manager for a large, critical project that promises to make a positive difference in the workplace.

It’s behind schedule.

How do you solve this big problem?

How can I encourage my team to meet their deadlines?

  • Provide accurate time and sprint estimates.
  • Prioritize the project activities and user stories.
  • Improve the team’s time management.

Those are a good start, but what are the barriers that currently prevent the team from meeting their deadlines?

  • The team gets invited to more meetings than they need to attend.
  • There is constant scope creep.
  • Team morale is dipping.

You can see already a plan forming. You have a list of positive habits to encourage and detrimental behaviours that need to stop.

Let’s review our answers and decide which we want to iterate through and which are decomposed enough to give us items we can take action on.

Improved Time Management:

The first action is to reduce the number of meetings the team needs to attend. This will increase the amount of productive time they have and help ease some frustrations.

By prioritizing project activities, the team knows they are working on the right items at the right time. And they have more time in the day to do so.

The team’s time management improves because of fixing other problems. No need to dig deeper.

Provide accurate time and sprint estimates:

There are plenty of variables to consider when giving accurate estimates. Understanding the feature request, level of experience of the people doing the work, and the estimation process, for example.

None of those are clear within our answer of provide accurate time and sprint estimates and so we need to decompose or iterate our way deeper.

How can I encourage myself and the team to provide accurate time and sprint estimates?

  • Prioritize the features in the backlog so we know what’s important to the project sponsor and which have technical dependencies.
  • Create user stories that are unambiguous and understood by every member of the team.
  • Have the right people work on the right tasks for their level of experience.

What barriers do I need to remove for this to happen?

  • There is a feeling that everything is important, to be worked on RIGHT NOW!
  • There is little trust between the team, project manager, and the project sponsor.
  • Scope creep causes the sprints to devolve into chaos.

The plan takes shape

To get your project back on schedule, you have a list of actionable changes you and your team need to make:

  • Reduce the time the team spends in meetings.
  • Have the right people do the right work.
  • Create complete and clear user stories.
  • Prioritize the backlog.

The changes will create the following results:

  • Engender trust – everyone understands the work that needs to be done and all agree with the time frame in which to do it.
  • Reduce scope creep – There are no surprise features during sprints, and if one arises, the team and sponsor understand its priority and potential impact on the current sprint.
  • Increase team morale – everyone knows they are working on the right tasks in the right order, and their workload is achievable.

Ready to solve your organization’s tough business problems? Ask these powerful questions and follow through on the answers:

  • How can I encourage people… insert desired behaviour?
  • What barriers do I need to remove for this to happen?


  1. Defined by the Project Management Book of Knowledge, decomposition is a technique used for dividing and subdividing the project scope and project deliverables into more smaller, manageable parts. Which is a business language way of saying you have broken down the work into parts that are small enough to be assigned to a single person or team. ↪︎ return
  1. I was tempted many times to “encourage” my old Triumph Spitfire to start by using a hammer – not recommended. Always seems to work in Hollywood for some reason though… maybe because it’s James Bond and a Trabant. ↪︎ return
  1. From the Equine Helper article on riding for beginners: “A horse can feel any body movement you make while you’re sitting on their back. When you look where you want to go, your body position adjusts to look that way.

    For example, if you’re sitting on the horse and you look to your left, you turn your neck. Your horse can feel that, and it signals to them to go left. So if you look up you tell them to keep going straight. If you look down, you’re essentially telling your horse to stop.↪︎ return
  1. The A-team was an American TV series from the 1980s. One of its most quoted lines is Hannibal’s “I love it when a plan comes together!” And because you can’t have the A-Team without a certain level silliness, here’s the team flying a tank from the 2010 movie. ↪︎ return
  1. Two short clips from the movie I, Robot with Detective Spooner asking questions of the hologram, Dr. Lanning. ↪︎ return
  1. I’ve always had a thing for Huskies, thanks to Jack London’s Call of the Wild and White Fang. But I doubt even my laid back Black Lab could cope with this level of drama. ↪︎ return