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Rethinking Asking the Stupid Question

Business Analysts ask questions; that’s what we are paid to do. We are encouraged to be inquisitive, “there are no stupid questions.” We are taught to ask “why” five times to get to the root of the motivation. Most of the time we feel good about asking questions – we’re prepared, we know what topics we want to cover and we know we are talking to the right person. And yet sometimes we realize that no matter how we twist our brain around, what we are hearing doesn’t make sense. It could be as simple as an acronym we haven’t heard before, or as complex as a decision that is so wrong-headed we can’t believe everyone just agreed to it.

What do you do when you have to ask a question you wish you didn’t have to ask? I have seen good business analysts unwittingly shoot themselves in the foot by using this common wishy washy preface.

“This might sound stupid, but…”, or “This might be a stupid question, but …”

Why do we undermine ourselves by prefacing our question or remarks with wishy washy language? The preface says essentially, “I’m insecure about asking this question and I’m expecting you to make me feel bad for asking.” Yes, that’s a harsh assessment – but I’m trying to make a point. You might think that because you are going to interrupt the discussion, the preface is a way of being polite. Is it? Putting the idea into people’s head that you are asking a stupid question nearly guarantees it, which is counterproductive to the importance of your question. Also, you want to save your “stupid” question prefaces for sneak attacks.

There are exceptions to all rules, including the “don’t ever say, “This might sound stupid, but…” rule.  In some situations the clever BA will want to launch a sneak attack by asking “crazy as a fox” question, for example, you perceive that people are going along with a line of thought that doesn’t make sense, and you’re about to bring them to their senses with cogent questions that cut to the heart of the matter. In this case, the wishy-washy preface telegraphs to the group that you’re about to pounce. Telegraphing your intent is a viable strategy to get people to pay attention.

We’ll leave the exception aside, and focus on a better approach to asking clarifying questions that require you to interrupt. In general, say what’s on your mind. It reinforces your credibility to present your ideas with confidence. Instead of flogging ourselves with the idea that “I should know this”, try adopting the Generous Listening attitude. What is a generous listening attitude? It’s the view that we Business Analysts are there to hear the essence of the other person is saying, and to it reflect back so they can hear themselves more clearly. It’s not merely replying “So what I hear you saying is …”, and it’s not asking a bunch of questions to further clarify what they are saying so we understand perfectly what they mean. Generous Listening is listening in a frame of mind that helps a person understand what they have conveyed to you and the group.

On the surface, the Generous Listening paradigm’s advice seems contrary to what we business analysts are told to do; Generous Listening advises us to avoid the questions “How?” and “Why?” questions. Before you dismiss this advice, consider creating a space in your toolkit for new questioning strategies. “How” and “Why” are great questions when appropriate, but they can shut down conversation instantly when you’d rather keep the conversation flowing and growing, and when you are interrupting for a clarifying question, usually all you want to do is get your answer, and let the discussion resume. As we BAs know, asking “How?” when a person does not yet know “What” results in mere speculation.  

Think about your frame of mind when you listen to a discussion. I know I’m listening for flaws in a person’s reasoning, overlooked cause-and-effect scenarios – my mindset is so tuned for critical analysis that I’ve assumed that there’s something wrong before they finish their sentence! Generous listening is the process of getting at the “what” in the other person’s mind and assuming the “what” is there even if they need help articulating it. The question “Why?” tends to spark defensiveness. Even when appropriate, it may be better to say, “Help me understand your thinking on this … “

Generous Listening recommends adding the following phrases to your toolkit to listen generously and expand a conversation:

That’s a great idea!

Please say more about that.

Interesting! What else?

What would that make possible?

What would that allow for?

Tell me more . . .

What would make that possible?

Help me understand . . .

When we ask questions such as, “What would make that possible?” instead of, “What could go wrong?” an entirely different conversation results. Try it! Incorporating these simple phrases will completely change the character of your communications.

Let’s get back to the short interrupt preface phrases.

Not great: “This may sound stupid but, have we assumed that … “

Do you really need the preface? Here are three alternatives.  

Okay: “It sounds like we have assumed that …, is that correct?”

Direct, but could put the person on the defensive: “Why have we assumed that …”

Better: “Would you say more about … , it seems that we have assumed that …”

Here are three additional phrases to use for a quick interrupt:

“I just want to make sure I understand, “DR” in this conversation means “disaster recovery, right?”

“Let me repeat what I just heard, you tell me if I got it right. …”

“Could I just verify what I’m recording for the meeting minutes / for my notes …  “

Tips for asking a question that you wish you did not have to ask:

Keep it simple.
Eliminate the preface, eliminate add-on questions. Phrase the question in words that the group will understand. By keeping questions simple, you avoid inadvertently inserting distractions into the discussion.

When we say “DR” here, are we talking about disaster recovery or a data repository or dead reckoning?”

The form of this question is “A, B or C?” The simplest form of the question is, “A?” Ideally someone will say, “disaster recovery”, you say, “Thanks” and the discussion continues smoothly. Alternatively, if you ask, “A or B”, someone might remember an issue related to the data repository and the discussion will veer off in that direction, leaving loose ends on the disaster recovery topic. Including the ludicrous possibility of dead reckoning adds a touch of humor which could be useful if you are trying to diffuse a tension-laden meeting, but it distracts people from the topic so use that gambit only when needed.

Be relaxed.
When asking a question you wish you didn’t have to ask, don’t make it worse for yourself by telegraphing your unease. Be relaxed, when you ask your question, wait for the answer, then let the discussion carry on. When you are nervous you will increase the anxiety level of the people around you, whether or not they are consciously aware of your discomfort.

Asking questions is our job! When building trust and a shared consensus of reality, making assumptions is the kiss of death. Asking questions, even a question that you are sure everyone knows the answer to except for you, shows that you are paying attention and striving for a solid understanding. Interrupting for clarification can be done without disrupting the flow of discussion and without undermining ourselves.

Don’t forget to leave your comments below.

Cecilie Hoffman’s professional passion is to educate technical and business teams about the role of the business analyst, and to empower the business analysts themselves with tools, methods, strategies and confidence. Cecilie is a founding member of the Silicon Valley chapter of the IIBA. She authored the 2009 Bad Ass BA series for BA Times and most recently the poem, A is for Analysis. See her blog on her personal passion, motorcycle riding, at
[email protected].