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  • Writer's pictureMartha Olsen

Ask Better Questions

“Question everything.” - Albert Einstein

All good positioning and messaging rests on a foundation of customer-driven discovery.


I’ve been told I ask good questions. It helps that I’m basically a curious person. To be curious is to be customer driven. To want to know (and be able to articulate) how any product or solution can solve meaningful and relevant problems in the world. Whether or not you were born curious, nosy, or naturally inquisitive, the good news is that questioning is a skill that can be honed.


There are good questions, and great questions, but no perfect questions. The best we can do is aim for questions that come from genuine curiosity, love of connecting through our messages, and the willingness to walk a mile in the shoes of our intended listeners.


Consider the messaging brief, the classic tool to align everyone internally on customer/market communications strategy. Early on, I would interview subject matter experts (SMEs) and ask check-the-box questions like "who is the target audience?" and “what is our value proposition?” Their eyes would glaze over as they defaulted to familiar talking points. I was essentially asking them to do my job – the art of surfacing the positioning and messaging in a way that is clear, compelling, differentiable, and even inspiring.


I learned quickly that building a truly inspired messaging brief does NOT mean taking dictation from SMEs. And if my questions are uninspired and routine, our positioning and messaging can end up focused on a product’s features and capabilities and won’t help connect with customers’ aspirations, challenges, and motivations.


Great discovery-based questions help create these connections, they help us get to know the customers we seek to serve, they help us empathize, understand why things are as they are, and what changes we seek to make in the world.


Discovery is typically associated with the early stages of a product’s journey – from hypothesis to design to delivery. Bring that same curiosity to every stage in bringing solutions to market. Think of discovery like a baton passed during each of the important hand-offs in the race to market – between engineers and product managers, between product managers and product marketers, between product marketers and marketing communicators or sales enablers. “Why did we build this? Who will it help? How does it make a difference?” These are all questions important to effective communications.


Take your questions from good to great


How can you push past traditional questions to make your messaging brief be more relevant, even exciting?


New to this? You may be the most valuable person in the room. Because a fresh perspective can help overcome the curse of knowledge – a cognitive bias that occurs when product teams get caught up in company pressures and market dynamics, and take for granted what actual customers know and think. A seasoned pro? We can all keep perfecting the art of the question to unlock hidden insights and capture ah-hah moments.


Instead of: Who is the target audience?


Try: Who is this solution designed for? What insights do we have about them? What do they do, think, and feel today? (Persona-building can play a very useful role in messaging and marketing).


Instead of: What is the customer’s challenge?


Try: Why and why now? What shifts in the world are changing the rules of the game? How are we helping customers adapt to this change and remain competitive? (See Andy Raskin who has much to say on the power of narratives framed around the why and why now?).


Instead of: What are the customer’s pain points?


Try: What obstacles or challenges will this solution help the customer overcome?


Instead of: What are the key features and benefits of our solution?


Try: How does our target customer describe the solutions they need and the value they are seeking? What meaningful impacts and outcomes will they experience by using our product? How will it fundamentally improve their processes, results, experiences etc.?


Instead of: What are our key differentiators?


Try: How will we differentiate our solution in terms of what our customers care about?  When our target customer evaluates different options, what decision criteria will matter most? And don’t overlook that “do nothing” is also an option you’re competing against.


The key is to go beyond the traditional "who, what, where" questions and uncover the deeper "why and why now" that motivates your customers.


Get past your assumptions


Discovery-based questions also help challenge assumptions and avoid habitual or unsubstantiated positioning and messaging. 


In Think Again, Adam Grant makes the point that we can never be 100% sure of what we know. The world is simply too complex and changing too fast. That's true of the markets and customers we serve. We need to also develop the ability to unthink and unlearn.


Great questions are ones that can guide us to some of that unlearning, to take the polished overwrap off our assumptions and ask anew, “Why are we doing this? What unmet need in the world are we solving for?” High performance companies are characterized by learning cultures, where re-thinking is routine. Research by Deloitte shoes that companies with learning cultures are the most innovative and more likely to be first to market.


Questions help create stronger connections


Over time, I've honed my questioning skills to bridge the gap between what product teams want to convey and what markets want to hear. As the positioning and messaging experts in the room, we are the "last mile" of go-to-market strategy and execution. Our work empowers campaign builders to build, content creators to write, trainers to guide, and sellers to sell.


Ultimately, the messages we create help build deeper connections across internal teams and also with the market and customers.


Keep practicing the questions that can help you get closer to these important outcomes.

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