Flip The Script - Take Control of Your Interview (PUBLISHED)
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Questions Interviewees Should Ask



What problem are you trying to solve by making this hire?
Why is it important?
What are the consequences of not hiring the right person?
What are the deliverables for the first the 30/60/90 days
What will success look like in a year

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111 GREAT Questions Candidates Should be Asking
Imagine wrapping up final interviews with a company knowing that you not only had the chance to share your story and skills, but that you gathered all the information you could about the company, team, and role in order to understand whether this is the right opportunity for you. Asking focused questions connected to your personal priorities is empowering and builds your confidence at each step of the process, especially when you need to determine whether to accept an offer.
If you want that feeling, it’s time to design a 360° strategy for your interviews. Building your plan will enable you to get the most out of the process, just like structured interviews help interviewers achieve their objectives. Asking targeted questions around your priorities to specific people will make the conversations more illuminating and productive. And, candidates who ask the best questions stand out.
This section of the book exists to help you create the plan and take action to make your interviews work for you. As you dig into the question database, you’ll find a common question paired with insights about why it will not get you the information you need. Each of the common questions is then reframed with what you can ask instead, and highlights about why that framing will unlock valuable details about the role, team, and company. This is a chance to bring your voice and power into the process and builds upon the content and exercises from the previous sections of the book. I have aligned questions by persona and topic as a starting point. I encourage you to think about what questions you need to ask and who is the right person for you to ask them to—you may align the questions differently!
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Framing is the process of breaking down a problem into a set of choices, trade offs, and options that enable a team to make a call and move forward.
A few benefits of good framing are:
Common language: Framing enables a shared, well understood sense of the problem. Even on its own, establishing a common language can facilitate better conversations and move teams forward.
Question prioritization (AKA finding the "eigenquestion"): One of the critical disciplines of framing is to "find the right question." Too often debates start with "solutions," before we determine if we're asking the right questions, in the right order. We'll discuss the term "eigenquestion" in a bit, but good framing of problems often requires rotating perspective. As we saw in the YouTube example, changing the question may be the best course for illuminating a path forward.
Options enumeration: Great decisions start with a clear set of options, as hard problems are rarely as simple as a "yes/no" on a single option. The book is a good resource full of data and stories of how teams that consider options make better decisions.
Inclusion: For most people, their ability to participate in a debate starts with feeling heard. Good frames give a spine to the variety of options and opinions suggested by others. Once they are all in place, people can let go of their initial opinion, and objectively discuss the alternatives.
Faster decisions that stick: A common complaint of structured decision making is that it can be time consumingーwhy bother constructing alternatives if one of them is already obvious? To be clear, this toolkit should not be used on every decision. On the flipside, when faced with a difficult decision, I prefer to evaluate the process based on a different type of speed. The worst decisions in these cases are ones that are arrived at quickly, but are just as quickly reversed, and thus the apparent speed turns into an illusion. Good framing helps produce "decisions that stick."
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First-principles thinking is one of the best ways to reverse-engineer complicated problems and unleash creative possibility.
Sometimes called “reasoning from first principles,” the idea is to break down complicated problems into basic elements and then reassemble them from the ground up. It’s one of the best ways to learn to think for yourself, unlock your creative potential, and move from linear to non-linear results.
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