Wonder Why

Episode #8
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I’ll never forget my first day on the job as a systems programmer. I can still remember walking across the barren parking lot to the smoked glass entrance. Just south of Toledo and right off Interstate 75, those shiny offices seemed so out of place in the middle of a soybean field. I entered National Family Opinion, a large market research company, with a mixture of anticipation and panic. Perhaps because I didn’t have the slightest idea what I was doing.


I was still in college working toward my computer science degree, but the company let me take lunch or leave early to rush down the freeway for classes in Bowling Green. Taking one or two classes a term while I worked full time at NFO added years to my eventual graduation, but it seemed worth it.

I had been working in the university’s computer lab for several terms, mostly sorting printouts and answering the same question over and over. There was a post on the bulletin board in that lab for the systems programmer job. I didn’t know exactly what a systems programmer was, but intrigued, I tossed together a resume and sent it in. As I noted in episode one, I’d had a lot of jobs by that point, but none in computers, so I was more than a little surprised to get an interview. Let alone the job.

I was shown to my cube by Lee Norton, my new boss. I’d seen bathroom stalls bigger than that cube, but it had a glorious VT100 terminal on the desk. I had used one at school but this one? It was mine. I tried to look nonchalant to Lee.

I also tried to not look lost as Lee showed me my login credentials and got me set up. The VT100 was connected to a VAX computer made by Digital Equipment, quite state of the art in 1980. But with only a single survey class on one under my belt, being the “systems programmer” felt like being tossed into the deep end of the pool.

As I pored over the manuals trying to get my bearings, a computer operator came rushing over. One of the hard drives had stopped working. Could I help?

We scurried to the huge computer lab that took up what seemed to be one entire wing of the building. It looked like a clean room, glassed-in and filled with dozens of machines on a raised white tile floor. Opening the door, we were greeted with a blast of cold air and the deafening roar from the machines and the massive air conditioning system. Over on one side a small crowd had gathered around the dead hard drive. Its access panels were open, and people were standing around staring at it, like one might at a dog that had been hit by a car.

The drive held most of the currently active jobs and at least half of the company was stalled without it. The drive was a Digital RP07 — the size and shape of a washing machine. It cost more than a top-of-the-line Mercedes and stored all of 500 megabytes. Today, for 25 dollars you can buy a chip the size of your fingernail that holds a thousand times as much. Until that moment, I’d never even seen one, except in photographs. Could I fix it? Ummm…

I reached for the huge power switch and turned it off and back on. One of the lights on a board inside flashed green for a while, then red. And a matching error light on the display panel up top flashed in sync. I pondered for a minute, then turned to Lee who was hovering over me. “I think we need to call the repairman.” The operator promptly did.


It was right then when I wondered why. Why did Lee hire me? Months later I got the chance to ask him. And that’s what this is all about.


This is Leading Smart, the show about Managing in the Brainpower Age. It’s a field guide to the joys and challenges of leading and working in the modern workplace. I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

In this podcast, we’ll take a look at how people meet the challenge of managing smart people in this Brainpower Age. Each episode, we’ll explore everyday problems and provide practical tools you can use to be a better and smarter leader.

This is the third of our episodes looking at the challenge of hiring brainpower workers. In this episode we’ll look how to interview brainpower talent. This is Episode Eight: Wonder Why.


That first day was rocky, but I soon settled into the job. I read every manual I could find on the VAX systems — entire shelves of blue three ring binders, each inches thick. I even made friends with the Digital repairman to get access to company-only materials.

A few months in, I felt confident enough to ask Lee why he hired an inexperienced kid without a college degree for this important job. He said he knew I was green, but he could tell immediately that I was smart. He was impressed by my fearlessness and passion for learning everything I could. He was sure I’d figure it out and that it was clear five minutes into the interview. “See,” he boasted, “I was right.” We then both laughed about the broken hard drive and my clueless response that first day.


As the company grew and added more Digital VAX machines, I also grew into a capable systems programmer. The company was frugal and worked those machines well beyond their design limits, often putting as many as 100 users on them at a time. Within a couple of years, I was an expert at milking them for every bit of performance. I eventually took a job with Digital itself, touring the Midwest as a consultant, tuning similar machines for a range of Fortune 500 companies. That lead to my starting my own consulting firm, which I later sold to a company that was, in turn, sold to Microsoft.

And that all sprang from a hiring manager who saw a smart person with a thirst for learning and passion for the job. I wasn’t judged on the specific skills I had, or rather didn’t have, but on my potential. And that bet paid off handsomely, for both the company, and me.

When I look at hiring brainpower workers, those are the qualities I find most important. Intelligence. Passion. The ability to communicate. And a voracious appetite for learning new things. So when I’m interviewing someone for a brainpower job, those are the things I’m looking for. Not what they know or can do now, but what they will know and will do.


But how do you interview for those these so-called “soft skills”? As we discussed in the last episode, it’s not with tests or trick questions. What works best is a conversational style that makes the interviewee comfortable and encourages them to show themselves at their best.

I usually begin with the obligatory small talk. The weather, their journey in, and so on. The goal is to make them feel comfortable, and to make me and the situation less scary.

Then I give their resume the respect it deserves. They worked hard on it, and I like to show that I have read and understand it. I’ll ask them about any holes I see, gaps in their experience perhaps, and about any interesting or odd jobs they’ve had. They’re prepared for these questions; this is mostly to honor their effort and to hear their explanations in the flesh. You rarely hear anything new, shocking, or disqualifying in this part of the conversation. If you did, they wouldn’t be there in the first place.

Then to get things rolling, I’ll toss up an interview softball — some classic interview question. There are lots of these: “tell me about your favorite success from the last year.” Or “what do you do when you’re told your idea is silly?” Or “tell me about a project you worked on that went bad and what you did about it.” Just some standard interview question, to get them started. Here too, they’ve likely thought about these things and have an answer at the ready.

But the twist comes when you listen really carefully and use that to drill down. Perhaps they say, “I like to be really organized and keep lists of everything”. Yeah, you think, so does everybody. So I’ll ask “why?” You get some trite answer about list keeping. Don’t let it go. “How do you do that, specifically?” “Why do you use post-it notes?” “What if you run out of room on a note?” “How do you share post-it notes?” Keep drilling on the why. “Why post-it notes and not an online tool?”

The idea isn’t to understand their post-it note fetish, it’s to get them out of the canned answer and into something real. Into something they’ve spent time thinking about. And with any luck, something they’re passionate about. The best answer is someone who spends five minutes explaining their post-it note system, and why they’re better than any online tool. The point isn’t the question, it’s not even the answer, it’s the thinking. It’s the passion. It’s the why.

Microsoft used to famously do this with really silly open-ended, unanswerable questions. Like “How many manhole covers are there in Seattle?” There was even a cottage industry built on logging and sharing Microsoft interview questions. And there is the famous book “How would you move Mount Fuji?”, all about how to ace the tech industry interview process. The point of those questions wasn’t to get the right answer, it was to see you think. To see if you asked the right questions. To see if you could “get into” the process and get involved in trying to work out the answer. And to see if you can communicate your answer and the process behind it in a clear and thoughtful way.

These silly random questions are fine, and there seems to still be an online battle for the latest and most obscure. But I prefer to start with the canned questions and drill down from there. This makes them comfortable and takes it into their personal realm. Dive deep off what they are saying. It shows you’re listening, which is warm and respectful. But more importantly you’re likely to hit several important areas at once: how they think and talk about things, and also if they have any passion for some subject. They’re unlikely to have a passion for manhole covers, but they will on some topic, so I work to find that.

When it comes to the desire for learning, I like to ask: “tell me something you’ve learned in the last couple of days. Anything, not particularly about work, about anything. Just something you know today that you didn’t know last week.”

Here too, the answer doesn’t matter. Seriously, it could be anything. And you want them to get talking about it. Then you drill down from there. What didn’t they know? What surprised them about it? Did that lead them to question something else? And what did they do with that knowledge? And of course, why? Why does this topic interest them?

If that doesn’t work, keep exploring. “Do you read books, listen to podcasts, watch YouTube, explore forums? What are some of your interests?” Here again, it’s not really the subject. It’s in many ways, better when it’s a subject that has nothing to do with work. With any luck you may share a favorite book or podcast, even a passion or hobby. For me, it’s almost better if it’s something I know nothing about. “Tell me more”, “how does that work?”, and “do people really do that?” These conversations can be enlightening and pure joy, as well as to help you to understand the candidate.

If that doesn’t get them rattling on about something, ask them directly. “What is something you’re passionate about?”

Throughout this, what you’re looking for is a gleam in their eye. Something that lights them up. Something that they can’t stop talking about. Something they’d do without wondering why. If you don’t see this, if they can’t show passion about something, anything, it’s going to be hard to see them doing that at work.


Some organizations have developed an interview style that seems just shy of hazing. They like confrontational interviews or putting the candidate in challenging or frustrating situations to see how they react. I gather this is to test them on their strength of character or their willingness to push back.

Those are valid things to plumb for, but I find you can get there through a conversational approach. Find something they state with passion and push back on it. “I think post-it notes are a lousy way to keep track of things.” And then keep pushing to see if they get frustrated or strident, or work to dissuade you.

Some are quite fond of the skills testing interview. Making people write code or design structures right there on the white board. Or perhaps give a presentation to a hostile room. The interviewers work to find anything to nitpick or annoy the candidate. To throw them off their feet. Although it seems clever, I think this is a lazy way to interview. It’s easy to set up hoops to jump through and requires little or no work on the part of the interviewer. Worse, it puts people off and can even be insulting.

Still others like to make the prospect do all kinds of research and prepare both documents and presentations on the subject. I’ve seen some so complex it seemed as if they were just trying to get some free work done by their interviewing candidates. If the candidate has a job, and more than one of these kinds of interviews to prepare for, they’re likely to just decline rather than perform like some trick pony.

In general, I find these aggressive forms of interviewing uncomfortable, often cringeworthy. For many candidates the confrontational format makes them simply shut down. And anything that even feels like hazing rarely ends well. Perhaps you get to see how they handle pressure, but smart, talented people don’t enjoy being played. They find themselves wondering “why do I have to put up with this?” And if they have other options, for organizations that don’t pressure them like this, they’ll probably take them.

I also wonder how you take an interview experience that was deeply stressful, if not downright terrifying, and suddenly switch gears. “Well, that’s done, you passed, now let’s talk about how great it is to work here.” As an applicant I’d find myself reeling, confused, and feeling conned. If the organization is going to this level before they even know me, what’s it going to be like when they do? And, is this kind of confrontation a regular part of work here? Why is that? Do I want to be a part of that?


I prefer to approach interviews with warmth and respect. I want my organization to reflect that, and I want the candidate to see that from the very first impression. Certainly, I need to understand how they handle push-back, but I don’t need to test their response to the worst of it to see how they are at their best.    

The goal of a great interview is for both the manager and the candidate to feel like everything just fits. The candidate belongs, and the job responsibilities seem a good match for them. But this is just the time when you, as a leader, need to be careful. A good fit can be for a variety of reasons, and some of them aren’t necessarily positive. In the next episode we’ll explore the dangers of a “good fit” and how that can lead to problems of diversity and exclusion. But that’s next time.

In the meantime, wonder why. The best interviews of brainpower workers are spent mostly exploring a lot of “why” questions. Why does the candidate get up in the morning, why are they in your office, and why do they see themselves on your team? You should be asking yourself why they make a great addition, why they will add ever-increasing value, and ultimately why should you hire them? By the time the interview is over, neither of you should be wondering why. You should know why.


Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my website, CLWill.com. That’s C-L-W-I-L-L.com.

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That’s it for this episode. In the next episode we’ll continue our look at hiring brainpower workers. Next we’ll look at the challenges and risks of a comfortable hire, it’s called “Fits and Starts”. I hope you’ll listen. Until then, please remember that each of the several dozen decisions you make today are part of Leading Smart.