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Asking the Right Questions to Solve Problems Better

Critical Thinking and Problem Solving

“If you define the problem correctly, you almost have the solution” – Steve Jobs

“We cannot solve our problems with the same thinking we used when we created them” – Albert Einstein


Quotes from two of the most influential people of the last hundred years – and advice we would all do well to take today when addressing business problems.

It sometimes seems like problems are everywhere in 21st century businesses – barely a week (or a day?) goes by without a meeting taking place to solve the latest problem, whether that be how to fix that bug in the latest software version, how to compete in an ever-more-crowded marketplace, or how to make an office move work for all staff.

Of course, it’s not really a modern phenomenon at all – businesses have always operated in this environment – it’s just that the problems are different these days. However, our goal, that we should solve these problems, is the same.

In my consulting work with management teams, we often look at solving business problems – and one of the hardest things for a team of senior leaders to do is to step outside the problem and look at it objectively.

They’re in the problem because, often, they were part of the team that created it in the first place. Our natural tendency is to use short-term, tactical thinking to solve problems, but this often provides a short-term solution which either leads to the problem rearing its ugly head again in the future, or to another problem coming along as a result of the solution to the first. Solving problems is a vicious circle.

So what’s the answer? In fact, there are two – and they’re both related to the questions we ask.

Answer 1: Ask Neutral Questions


One challenge when we solve problems is that we don’t think big enough. I was recently doing some work with the senior management team of a scale-up in London, who were finding that since the company had reached a critical mass, internal communication was getting harder and harder. It’s a universal problem which vexes even the most experienced leadership teams.

To open the workshop, I encouraged them to put together the questions we should attempt, as a group, to answer during the days. The questions they came up with were along the lines of:

  1. How can we encourage people to read the intranet when they switch on in their mornings?
  2. How can we get important news to people’s personal mobiles?
  3. How can we re-design our emails to make them easier on the eye?
  4. How many company meetings should we run to ensure good attendance at each?

On the face of it, these aren’t bad questions – they’re action-focused and are worded in a way that something practical should come out of asking it. But in fact, they’re poor questions to ask when solving a problem, because they get very narrow answers.

No ground-breaking ideas will come out of these, because the desired solution is integrated within the question itself.

What might come as a result of, for example, question 3?

Probably the marketing team will do some work on an email template which might take a day-or-so then spend the following couple of months trying to stop the CEO brain-dumping into this pretty new template.

Eventually, after much re-design and head-banging, a new, fresher company newsletter will go round that people still won’t read because everyone’s too busy to read company newsletters. The problem still exists.

Instead of these loaded questions, we should be asking neutral questions which encourage genuine reflection. It might be better to ask the following 4 questions to really understand the problem and to encourage out-of-the-box thinking in its solution:

  1. What exactly is the problem we’re trying to solve?
  2. Is it really a problem – is there a serious impact on the business?
  3. How do people like to receive information these days?
  4. What could we do to ensure that all relevant employees receive the information they need to work effectively?

Answer 2: Ask Expansive Questions

Critical Thinking


Asking neutral questions is great, but on its own, this isn’t going to give a deep understanding of the problem and its context that’s needed to effectively develop a solution. We also need to ask the right range of questions. At a high level, if we’re solving a problem, we want to know the following, in this order:

  1. What is the problem we’re trying to solve (definition and impact)?
  2. Where does the problem sit (background and current context)?
  3. What ideas do we have to solve it?
  4. If we action these ideas, what might the positive and negative implications be?
  5. What actions do we need to take to implement the solution?

The drawback with my earlier illustration of questions developed by a leadership team is that the questions addressed point 5 here – specific actions around a narrow range of solutions. These questions have a place, but only when we’ve understood points 1-4.

To help us develop strong solutions to problems, we can categorise the questions we need to ask as follows:

  1. Strategic questions:
    • Where are we trying to get to?
    • What’s stopping us getting there?
    • What impact is this having on the strategy?
  2. Analytical questions
    • Where’s the problem come from?
    • Why are things the way they are?
    • What events or decisions have led us to this point?
  3. Innovative questions
    • What could we do to solve this problem?
    • If that’s not possible, what else could we do?
    • What would an expert in this area try when developing a solution?
  4. Implicative questions
    • If we take these actions, what other problems might they cause?
    • What unexpected benefits could this solution bring?
    • What impact could this solution have on other areas of the business?
  5. Tactical questions
    • What steps need to be taken to deliver this solution?
    • Who needs to be involved in the solution?
    • What can we do right now to get this started?

If we work through this process, it helps us to develop solutions which are both innovative and effective, which is the advice given by Albert and Steve at the beginning of this blog post.

To learn more about how to identify and solve business problems, why now join our Critical Thinking & Problem-Solving course, where we explore all these areas during 3 highly-practical days of asking questions and taking actions.

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About Neil Shorney

Neil Shorney
Neil Shorney is Director and principal trainer at Navanter, a boutique sales and leadership training consultancy based in London, helping clients around the world to operate more effectively. Neil has been involved in project management since 2001 and has a passion for bringing sales and project teams together by giving soft skills to project managers and organisation skills to salespeople.

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