Week 22, 2023—Issue #258

Ask fewer questions, Teach again and again, and Develop strategic options

Andreas Holmer
WorkMatters
Published in
3 min readAug 23, 2023

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Photo by ThisisEngineering RAEng on Unsplash

Successful organizations do three things: they create value for customers, empower their people, and produce above-average returns.

Here are three ideas to help you do the same:

#valuecreation

Fewer Questions

The key to successful discovery is fewer, better questions

“The key to masterful discovery is leveraging high-impact sales questions. In other words, it’s not a volume game. It’s a quality game. For example, when you’re speaking with a c-suite executive, there’s a significant drop in success rates after just a few questions. Again, if you’re using well-framed, open-ended questions, you’ll find that a handful is enough to unpack your prospect’s business needs.”

From The Ultimate Guide to Asking Sales Questions by Gong

Andreas: This was a surprise to me. I don’t know much about sales, but I would have thought that more questions equaled better outcomes. But no. The more questions we ask, the less likely we are to convert. It’s something to keep in mind for the next sales call.

#personalfulfillment

Teach again and again

The best way to learn is to teach, again and again

“Richard Feynman…had a remarkable knack for explaining some of the most complex things in ways anyone could understand. [This is] how he approached understanding something deeply [that] helps explain some of his teaching skills:

  1. Spend time writing about a topic as if explaining it to someone.
  2. Then practice explaining it, speaking and drawing as if you were a teacher at the front of the class. You may figure out some other aspect wasn’t as clear as you thought and need to look into something.
  3. Refine any gaps you reveal until you can share the topic fluently and clearly.
  4. Then, simplify your language by replacing complex words and ideas with simpler ones and considering analogies to help people relate.”

From The Feynman Learning Technique by Sketchplanations

Andreas: I love this. Feynman was an extraordinary thinker, and his learning technique is totally on point. It makes me think of the proverb, “If at first you don’t succeed, try and try again.” There’s also a connection to the “build to think” mantra we use in design circles.

#organizationaleffectiveness

Develop strategic options

Organizations must strive for radical optionality

“The next era of competition is at hand. To succeed in an environment of high uncertainty, greater short-term pressure, and tighter resource constraints, firms must become even better and more efficient at developing options for future advantage while continuing to perform in the present. To achieve a state of radical optionality, firms must overturn some of the core tenets of strategy — by thinking while doing, exploring while exploiting, and striving for flexibility rather than fit. They must embrace complexity, learn to search and execute on ideas simultaneously, and engage with customers in their personal journeys. Accomplishing that will require new organizational forms and work practices, deeper integration between humans and technology, and next-generation performance metrics.”

From Radical Optionality by Reeves et al

Andreas: It’s high time to add “optionality” to your vocabulary. Long-term readers will remember the term from my series on complexity investing. In a business context, it means having multiple strategic options available. I think it’s key to organizational resilience and longevity.

That’s all for this week.

Until next time: Make it matter

/Andreas

How can we build better organizations? That’s the question I’ve been trying to answer for the past 10 years. Each week, I share some of what I’ve learned in a weekly newsletter called WorkMatters. Back-issues are published to Medium after three months. Subscription is free. This article was originally published on Friday, June 2, 2023.

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Andreas Holmer
WorkMatters

Designer, reader, writer. Sensemaker. Management thinker. CEO at MAQE — a digital consulting firm in Bangkok, Thailand.