Five Magic Interview Questions


Some years ago, I ran across a list of what I consider the most eye-opening interview questions on the planet. Well, maybe that’s hyperbole. But the fact of the matter is these questions never fail me. They consistently open up the conversation into nooks that produce insightful and interesting commentary. And my favorite getting-to-know-you question set is only five questions long.

These were described as job interview questions when I first ran across them. But long ago I re-purposed the original interview question set by adding a fifth question and began using them during my web governance audits with wonderful results…


The original four questions — plus my fifth addition — are both straightforward and magical because they never fail to provoke discovery:

  1. What are your aspirations for yourself and your organization?
  2. What are the things you do well?
  3. What are the things you do badly?
  4. In the scheme of all the other competing demands at this organization, where does this task fit in?
  5. What is the biggest risk you face, and what’s at stake if you fail to address it?

Expect the session for the five questions with answers to last from 15 minutes to a half hour.

It has been a proven winner in many settings for getting issues out on the table and sparking interesting conversations – I’ve been told they also work well for those who are new on the job, especially managers who are wise enough to listen to their staff and observe relationships before they charge in to make changes.

The best advice when you take over a new team or a new job is to avoid the pressure to enact immediate sweeping changes to prove your value. Instead, do not do anything new or different for a while until you could figure out how everything works and what the rough spots were. Only then are you ready to take action. You gain practical advice about undertaking new opportunities and understanding new vulnerabilities, quickly and without much upheaval through these conversations.

I always recommend one-on-one meetings or a visit over coffee or a meal as the right environment for the interview. Here, you can run through these questions with each team member in an informal setting to get to know them and your organization better. The same questions when asked in a group setting won’t yield the same results because people will tend to clam up and do not always feel free to talk with candor.


My method for a web governance audit includes fact-finding and research through a variety of means besides the interviews. These methods include:

  • A web scorecard
  • A review of the core documentation supporting the team
  • An analysis of the Web team organization chart
  • An online survey for a large group of those who work on the website

Amid all these information streams during the audit, one of my favorite is the interviews. Wonderful knowledge about the heartbeat of the web strategy reveals itself after I find the key players on a web team and arrange to sit down with them and talk about how they do their job.

I always bring a checklist of best practices for that function to see how things measure up.

But it is during the first part of the interview when I ask my self-described “best interview questions on the planet” that I gain traction for the truth-telling spirit of the meeting that I am aiming for.

Next time you talk to someone new, as part of a job interview, a research project, a client engagement or something else, try out my questions and see whether you don’t get enlightening results too.