Does that seem like an abrasive, if not invasive question? Why would anyone have the nerve to ask that, let alone expect you to answer it? And yet, in a job-interview setting, it happens. And when it does, it might not even be confined to “this year.” (That was just the title I chose for this post, given its timing.) Interviewers might ask about the “biggest failure in your career.​”

We all know the question “Tell me about a time xyz happened. How did you handle it?” That is an interview staple by now. Taken to the extreme, the question can be one specifically about a bad outcome. We all know how it feels to be in that place. To say it doesn’t feel good would still be bragging. At the very least, it feels like being stuck at the bottom of the staircase of the Pilgrim Monument in Provincetown, Mass. (Yes, you recognized that correctly in the photo.)

And now, with that one interviewer question, the floodgates open to release all that negativity into the conversation! Or do they?

There is no reason to start hyperventilating. As I said in an earlier blog post, there are the interviewers’ words, and then there is what they are really asking.

You don’t have to take up the interviewer on his or her specific wording. Not only do you not have to, in this case I caution against it. If you start out by saying “My biggest failure was…,” the very way it is worded implies there are two or more instances failure also happened, almost as big as that “biggest” failure. There is a substantial risk the interviewer will probe for those.

Therefore, you might want to rephrase the beginning of your answer to go something like:

“Well, there was that time things didn’t go as planned at all.”

Anyone can relate to that. You can do without using the word “failure” and still acknowledge the reality of failure. Saying things “didn’t go as planned” doesn’t suggest as much that the failure was brought about by you personally, and shifts the focus from your person to what happened.

Interviewers really want to know how you emerged from that time of failure. I can’t think of one successful professional who can truthfully say he or she has never failed. Interviewers worth their salt know that. They know the path to real success is never without setbacks and miscarriages.

So, rather than being blindsided by this question, come prepared to transform it into a story of learning and growth. Interviewers will see you as all the more experienced and resourceful for that, with the capacity for solutions for the problems of the future. On that note: Happy New Year!

​The other day, I heard about a new condo association that had recently emerged in a multi-unit house in the neighborhood. When I probed about any contractor opportunities connected to this association, I learned they had hired a professional condo manager to oversee all that. Then it turned out the real news was about trouble in paradise…
 
Some of the condo-association trustees apparently weren’t happy with the cleaning crew and with the way the condo manager was dealing with contractors overall. One trustee then vented liberally in a pointed e-mail to the manager—with all other trustees CC’d on it:

Umm…okay, the e-mail was so sharp, I chose not to show it. (But the photo made you look!)
 
The gist of the e-mail was that the honesty and priceworthiness of the cleaning crew was questioned, as was the manager’s competency in supervision and financial oversight.
 
Perception is not reality.
 
While some trustees did have questions, all were not on the same page even about the scope of the issue. That e-mail presented “facts” that really came down to observations interpreted in certain ways. Nevertheless, those “facts” were followed by hastily drawn conclusions, not to mention salvos of finger pointing.
 
Substandard communication puts all team members on the spot.
 
Functionally, a condo association is a team. In the case of this team, its “forming” was not long ago. Meaning, the team is now probably going through its “storming” stage. And yet, one trustee (i.e., team member) chose to speak for everyone—prematurely, in more than one way.
 
Now the entire condo association is left with the fallout, which is at least two-pronged: one, they have to scramble for common ground in assessing the issue; and two, there will be some fence mending needed, since the manager is not exactly thrilled with the slew of accusations directed at their own practices and at the contractors they work with. And again, it doesn’t help that all trustees are not on the same page as to what the problem really is all about.
 
For starters, I hear the author of that e-mail has since apologized.
 
In baseball, it is called an “unforced error” for a reason.
 
It didn’t have to come down to this situation. Whether any of the work by (or the dealings between) the condo manager and the cleaning crew was dysfunctional remains to be seen. Do I need to point out there are more adaptive ways of identifying concerns, and more professionally obliging ways of discussing them?
 
Perhaps this is a good time of the year to remember some of the benevolent notions, including the acknowledgement of ambiguity, giving the benefit of the doubt, and articulating needs. Come on—the season of goodwill, rejoicing, and cheer is just kicking into high gear!

It is that time of the year again—people dress up and put on certain specific impressions. Bars and streets are full of colonial-era figures, astronauts, and pirates…not to mention witches, ghouls, and vampires. Or whatever I personally have managed to come up with over time—see this collage.

​In short, people go to varying lengths to shape and communicate appearances, to be easily recognizable to others for who and what they are supposed to be.
 
Of course, people do that all the time. On Halloween, a costume is used to convey a certain impression. On any other day, what is used to achieve just that is a brand message.
 
Interviewer question: “Tell me about yourself”—or a particular facet thereof
 
The following was inspired by what a job seeker told me recently. So imagine you are at a job interview, and you get the common question “Tell me about yourself.” You start to proceed along one of the usual paths, such as how your childhood interests foreshadowed your later vocational choices.
 
But then the interviewer interrupts you: “No, no, no. Tell me what you do in your free time.”
 
If you feel taken aback by that “qualifying” question, to the point of being blindsided—keep a level head and try to understand…
 
What are they really asking?
 
They may be looking for clues of how you handle your work–life balance: Do you “relax” from your desk job by being a couch potato, watching reruns of early Law & Order seasons? The “historical” interest of it notwithstanding, that wouldn’t seem very “balanced.” What might go over better is if you say you do something “active” to refuel, to reenergize, such as running, cycling, or climbing.
 
Or they may try to probe how your “free-time self” is alignable with your “on-the-job self.” They might like to hear you say you play team sports (preferably with some kind of competitive incentive). Moreover, you might score brownie points by injecting that you alternate these times with times you focus on intriguing books. (“What are you reading right now?” is an interview question in its own right.)
 
There is no reason to take it too personal, because there is no reason to be too “personal.”
 
Prying as the question may sound, it really is an offer made to you to take control of the direction the conversation takes from there. You might as well take them up on that offer and present those “transferable” personality traits about you that go to show how the job in question is compatible with the personality you bring to it.
 
If you need to put on a figurative kind of “costume” to look like a good fit, then you may risk setting yourself up for a poor outlook on job satisfaction and job longevity. You might want to let your best judgment be your guide: If you don’t have to resort to any kind of “disguise,” that may be its own answer.

​One fine summer in California, I drove from Paso Robles to Salinas. I could have gotten there quite fast by taking U.S. Route 101. But I chose to take the Cabrillo Highway—State Route 1, which winds along the coastline and passes through Big Sur, with plenty of vista points. And then this view appeared in front of me—not one of the vista points, but it made me stop and take this photo.

​The photo shows the San Simeon–San Luis Obispo County line, near the Breaker Point peninsula. (This was before the severe drought that—sadly—caused much of the green to turn to brown.) I felt as though this particular view was trying to tell me something. I wondered what it was—besides the rugged, scenic serenity—that compelled me to not only take this particular photo but to also have it printed on canvas and hang it on the wall.
 
And then, over time, I realized: This was a visual analogy of where I was in my career journey. Let’s take a look at some of this photo’s characteristics.
 
Slight ups and downs are visible in the immediate road ahead.
 
That is to be expected in any career endeavor. I think anyone can relate to that.
 
Not sure where the road leads beyond the short stretch that is visible.
 
The continuation of the road is concealed behind the landscape around it. Will there be just one bend, followed by another stretch leading straight ahead? Or will the roadway take winding turns, perhaps hugging cliffs? For starters, the horizon—or what we see of it—suggests the road ahead will be going uphill.
 
Whatever lies beyond the horizon is shrouded in fog and clouds.
 
This section probably needs to be navigated with caution, at a slower speed. And you might want to make sure your car has fog lamps, just in case.
 
There is no one else around to go down this road.
 
This is your journey, at this point in time. Whoever else happens to come down this specific stretch of roadway will not continue on the same journey. They will focus on different details, and they may take a different turn when they get to a crossroads. And they will find different things to stop for. Case in point: I doubt anyone else would have stopped right there to stand in the middle of the road to take a picture. (Incidentally, the camera was pointing north—to my “true north,” perhaps?)
 
It turned out later I wasn’t quite yet where I thought I was.
 
I thought I already was in Big Sur. But later, as I reconstructed my path on the map, I found I still had a good six miles to go before “officially” entering Big Sur territory. I wonder how often I have made the same misjudgment about the place I was in as my career journey progressed. (In the case of Big Sur, at least I did get there soon afterwards.)
 
All in all, I can say I am glad I didn’t take the fast and easy route (U.S. Route 101). I would have gotten where I was going in less than half the time. But it wouldn’t have been half the experience at that. The meanderings of the Cabrillo Highway were worth it.
 
Oh, and about the fog and clouds on the horizon: They never deterred me from continuing on my journey. Although it was uncertain what lay ahead, there still was enough filtered sunshine to indicate things were going to be bright.

It is human nature to form snap judgments—to size up situations and objects in a matter of split seconds. That goes back to prehistoric times, when that capability often was critical to survival.

Granted, the human species has long been evolving. Normally, present-day humans give one another a little more time of day before passing judgment. Even so, you don’t have an infinite amount of time to keep someone’s interest beyond the initial “Hi, I’m Jay.”

It is not by accident that the general recommendation is to keep your brand message (a.k.a. elevator pitch, a.k.a. personal infomercial) so contained as to be delivered in 30 seconds or so. Of course you want to have more “ammo” in your “arsenal,” but you want to conserve it until you can inject it into the conversation, speaking turn by speaking turn.

So, in that 30 seconds your interlocutor is open to your spiel after graciously saying, “Tell me about yourself,” here’s what you might want to get across—meaning, what they are probably really asking:

1. What are you intrigued by?
2. What are you passionate about?
3. What type of challenge do you enjoy?
4. What type of result do people seek you out for?
5. Who benefits from what you do?
6. And, what makes you unique about the way you do what you do?

Consider the following example. First, here’s this version:

I majored in psychology, and my first job out of school was as a research associate. Later I pursued a career in publishing. To that end, I took a Certificate in Publishing program at Boston University. That career didn’t really get off the ground, but I did get a job as a workshop specialist at a One Stop Career Center. Soon I also became a Certified Professional Résumé Writer.

And now this version:

I help professionals connect the dots of where they have been so they can get faster where they are going in their careers. I elicit from clients how they have been contributing, how those contributions have benefited people and organizations, and what the assets are they want to be seen for. What I find particularly striking is when clients see new opportunities where they didn’t even realize they had something to offer. My own career path used to be somewhat meandering; that’s how I get where a wide variety of different professionals are coming from.

Judge for yourself: Which version offers more “hooks”? Which version is more likely to hold your interest past that first 30 seconds?

Right. The first version revolves all around some bullets in that person’s biography. They may even happen to strike a chord here and there, where people may see common denominators, but all in all, the first version takes the “Tell me about yourself” prompt a little too literally.

Now the second version ties in key clientele right away. It gives the listener an idea how this person approaches clients, and what they get out of our professional interaction. The part about clients discovering how some of their assets are marketable is particularly illustrative of the way they benefit from this person’s services. Finally, the mention of a “somewhat meandering” career path goes to show this person has a broad professional history he or she can apply working with many different types of professionals.

So what was your story again?