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4 of the best “naïve” yet strategically probing questions you can ask in business

A list of questions: Where, what, when, why, how, who

A list of questions: Where, what, when, why, how, whoOne of the things I absolutely love about my role as a business analyst is that I get to ask all sorts of naïve questions of my clients.   Being a business analyst creates the permission to call out the ‘elephant in the room’ and to ask those deepest, darkest political questions that others might be avoiding.  Clearly, this must always be done with respect, rapport and from an angle of curiosity – and when done well, those “naïve” questions can yield some extremely interesting outcomes and can create debates that help solidify and clarify organisational or project direction.  It helps avoid problems before they occur.


Even when working on projects, a group of apparently harmonious business stakeholders might suffer from invisible and insidious conflict bubbling away beneath the surface.  It’s just waiting to jump out – and if it isn’t exposed and dealt with early, it will grow and grow until it reaches an explosive proportion.  The conflict may have been festering for weeks, months or even years.  Naïve questions are a great way of exposing this conflict, ensuring everyone is on the ‘same page’ and pushing in the same direction.   Having some external challenge can be a great way of exposing this conflict and creating contentious yet productive debate.  In this article,  I’m going to share a few “naïve” questions with you that can help in these situations.


There are many questions that we could ask; here are just a few of my favourites.  These questions work in many situations – whether you’re working in a mid-size, small or multinational organisation.  They work when undertaking projects, as well as when considering business changes, challenges and business strategies.  They are useful for business analysts and business stakeholders alike:


1. Who is the customer, and what would they say?  A great question to keep people customer-focussed when discussing a decision or change is to consider how a customer would view things.  Clearly, it will be necessary to balance a range of vantage points, but it’s crucial to consider the voice of the customer.   This is essential whether developing a new product, a new website or even making an internal process change.  Imagine you’re a high street retailer and you’re changing your returns process so that a customer has to queue in a different part of the shop – will they like that? How will they react? Will the new process be beneficial, or disadvantageous to them?  What’s in it for them?


2. What do we actually sell or do in this company and why?  Right, I just know some people reading this will be thinking “What a ridiculous question to ask – that’s obvious.  Every business knows what it sells”.   Perhaps you’re right – and it’s sometimes necessary to ask this question in a more subtle way–but let me ask you this: Would every member of your exec team and every member of staff in your organisation describe your proposition in broadly the same way?  And would your customers describe the proposition in the same way too?  Perhaps not. Different departments may well have different worldviews on the organisation, its products and why it exists.

Imagine a life insurance company, does it exist to:

    • Provide valuable financial protection for those with dependents
    • Provide part of an overall financial protection package that an intermediary/broker can sell to a customer
    • Provide a tax-efficient investment vehicle by “wrapping” investment products with life insurance
    • Make an underwriting profit
    • Make sufficient return on investment for its shareholders
    • Raise tax revenues for the government

Your view on what the organisation does is likely to depend on whether you’re a policyholder, an owner, an exec member or an employee – and of course, it’s likely that some kind of sensible compromise would be met.  But can you imagine the challenge that would ensue if different directors in an organisation, or stakeholders on a project, had vastly different views on what the organisation is doing?    Supposedly “simple” questions like this can create useful debate—and debate that should be had as early as possible!   On projects,  a related question is “What problem are we trying to solve here”.


3. How do we know we’re selling or doing the right thing?  Some organisations “do what they’ve always done”, and there have been notable large companies that have failed due to their inability to keep pace with the market.  A keen eye on the business environment is key.


4.  … And how do we know we’re selling or doing it in the right WAY?  Are our processes fit-for-purpose? Are our customers happy? Are we collecting sufficient data and insight about our customers, and can we really tell?  Arguable, the days of simply “selling at” customers have gone – and if our organisation isn’t reaching out to customers in the right way… our competitors may well get there sooner.



These are just a few possible naïve questions.  So what questions do you ask when working on projects or working with your colleagues? I’d love to hear from you – please add a comment below.




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This post was written as part of the IBM for Midsize Business program, which provides midsize businesses with the tools, expertise and solutions they need to become engines of a smarter planet. I’ve been compensated to contribute to this program, but the opinions expressed in this post are my own and don’t necessarily represent IBM’s positions, strategies or opinions

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4 thoughts on “4 of the best “naïve” yet strategically probing questions you can ask in business”

  1. This as wonderful and useful article .. naive questions really helps us to dig the problem further to understand the root cause. People who have enough domain knowledge would hesitate to ask such questions as it can question their capabilities. So it is really important to create an environment before asking such naive questions. One I can think is that I will go ahead and tell the client that I will be acting as a layman person and proceed with this question. Or if we are in meeting I will probably say that lets assume that I don’t have any sufficient domain knowledge and I will ask you few questions that one would hesitate to do so and will continue the meeting.

    Please mention if you have better way to put it before you ask such naive questions. Thanks

    1. Hi Nutankumar,

      Thank you so much for the comment, and I’m really pleased that you found my article valuable.

      You raise a really interesting point. As you quite rightly say, it’s important to set an expectation at the outset that we might be asking questions that seem very “basic”, but are actually extremely important.

      The approach that you suggest of explaining this up front is a really good one. It’s really important to have a good rapport with the stakeholders, so they know *why* you’re asking questions — it would be rather counter productive if they felt it was a waste of time! So explaining up front is a very good idea.

      I often use phrases like “That’s really interesting, just to get this clear in my own mind… can you explain who the customer is in that situation?”.

      The beauty with this type of question is it seems very natural, and the person will respond: Perhaps they’ll say:

      “Of course, in this situation it would always be a retail customer”.

      However, often one of their colleagues will then interject, and perhaps they’ll say:

      “Well, it’s not *always* a retail customer, sometimes we sell business-to-business too…”

      This then creates the opportunity for a wider debate. We might ask “Ah, OK. What’s the difference between those customer segments. Are there any others? Which customers do we actually target here?” Plus the opportunity to follow up with more “naive” yet important questions!

      One thing I always think is that a good business analyst creates an environment where asking “naive” questions is OK. By asking them ourselves, we make it “OK” for others to ask them too. Perhaps someone who is usually reluctant to do so will chime in. This really helps getting to the root of a problem. It’s always a team effort!

      Thanks again for your comment, Nutankumar.

      Kind regards, Adrian.

      1. Thanks Adrian for your valuable reply. It is really important to create the environment in a natural way.
        One thing i like being a generic Business Analyst is that I can play my newbie card and will not go with any preconceived notions where other Domain BA’s may do.
        You rightly mentioned that we need to create a good Rapport with the clients before entering in such situations.

        I think “How to create good Rapport with Clients” would be a nice topic for discussion.

  2. I usually tell people early in the project that “hi, I’m the business analyst, and my job is to ask all kind of questions, including really stupid ones. ”
    People usually accept that and don’t get hung up on when I ask “ok, but what do you mean by ‘trade date’?”

    Of course, I have to prove at the same time that I am not actually stupid. That’s the tricky part 🙂

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