Is Your Professional Development Glass Half-Full or Half-Empty?

One of my favorite former managers, whom I am now fortunate to call a friend, used to say that “hindsight is the only option in the absence of foresight.” Perhaps that’s the reason I can now look back on the first 1.5 decades of my career and offer some insights about personal development.

In our careers, and perhaps in life, we progress through phases:

  • thinking that we know everything
  • realizing we know very little about anything
  • demonstrating that we know a lot about something (or for the fortunate, a small number of things)
  • accepting that we can never really be certain about anything, while remaining curious about everything
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What is an Executive, you ask? Usually I reserve sidebars like this for comedic asides, but US tax dollars commissioned the Occupational Outlook Handbook (http://www.bls.gov/ooh/management/top-executives.htm) and I want you to read it. Someone actually went to work over a series of hours to weeks and wrote this sincerely for the benefit of the US Economy. So please stifle all laughter when reading in the presence of public servants.

Previously I have written about specialization and capability development in career progression. In summary, as we follow a single career track our knowledge and proficiency become deeper and narrower, until we jump across to another track. Recently I realized two opposing corollaries to this concept.

The farther we progress on a single career track, two things arise

Pessimist’s view: the number of capabilities that you need to develop in order to advance gets smaller, and the chances that you have to practice or demonstrate them become less frequent. In my first year out of college, I was terrible at everything; pick any one skill and I would have 10 chances a day to practice doing it better (let’s start with “never hitting reply all“). Let’s say you are an executive with 25 years experience in the top decile of your industry, by some generally accepted scorecard. Maybe the thing at the top of your professional development list is “maximizing shareholder value from acquisitions.” Those are going to come along, like, once every 3-5 years? Even if you are in Private Equity or advise on deals you might only be personally responsible for a handful in a year. So the stakes become higher and the at-bats become scarcer. Pretty bleak.

Optimist’s view: your capability profile is positively differentiated from other professionals with equivalent tenure on other tracks, giving you an advantage in “disrupted” organizations. So if you are risk-tolerant enough to jump onto another track after developing significant capabilities, you are likely to find yourself in high demand (and it’s never too early to prepare a transition). Let’s say that on average, across industries, job descriptions for a given equivalent seniority level (e.g., “Vice President”) have 12 qualifications. If you are a top performer in, say, Marketing for a Software firm, and you see that there has been a major disruption in another industry, say, B2C Media or Telecom, you could find yourself in a situation where your skill set is a scarce and valuable asset compared to the incumbents who have been dutifully advancing their proficiency in the set of skills that was most valuable for the previous decade but is now less relevant. Will an executive search committee offer a prominent and strategically important role to an industry outsider in a time of disruption (read: crisis)? That will have to be the subject of another post!

So if you have managed to get this far in the post and are asking yourself, “What does this mean?” Here are is my advice, take it or leave it:

As you advance in your career, stay aware for opportunities to hone your craft, because the most important ones will become less frequent. At the same time, be willing to switch specializations because what is common in one organization could be rare and valuable in another.

What are the best job interview questions?

Mediocre interview questions are boring for everyone and don’t create clear differentiation between candidates, leaving the hiring manager to draw on gut instinct (also known as good old fashioned bias) when making a decision.

“How is this an issue?” Some interviews are doomed from the start.

Good interview questions help the hiring manager understand the relative strengths and weaknesses of a set of candidates in the context of the role’s requirements. Good interview questions are predictable enough that a candidate can provide composed, complete answers that put his or her best foot (feet?) forward, exhibiting both technical capabilities and unique personality traits.

Great interview questions make the experience engaging and informative for everyone involved. The best interviews build a positive reputation for the employer, regardless of whether the candidate receives an offer. The best interviews build confidence in both parties that there is a strong mutual fit and build positive momentum into the offer and joining phases of the hiring process.

So what are the best interview questions? Here are a few categories you should test for, regardless of the job description, along with a few examples I’ve encountered in my experiences on both sides of the interview table.

  1. Domain knowledge: “Tell me about five subjects on which you’d consider yourself an expert and how you gained knowledge in the area.”
  2. Interpersonal dynamic: “Think of a time where you discovered a mistake that would have caused significant cost to your team if it was not corrected. What was the mistake, who made it, and how did you resolve the situation?”
  3. Adversity and its aftermath: “Tell me about the most significant failure in your last role. What specific, personal contribution did you make that created the failure?”
  4. Unique contributions to success: “Tell me about the most significant success in your last role. What specific, personal contribution did you make that created the success?”
  5. Self-awareness and commitment to development: “What would you say is your main development area today? How did you become aware of it, and what are you doing to improve in that area?
  6. Professional relationships: “Looking at your resume, tell me in one sentence for each transition why you left and how you found the next role.”
  7. Mental fatigue: Near the end of the interview, ask the candidate to stand up in front of a white board and work through a tough logic puzzle like these involving weighty things, calendar cubes, or other popular techie puzzles. It’s not the answer that matters, it’s how the candidate demonstrates their ability to apply structured thinking under pressure.
  8. Mutual evaluation: Last, let the candidate ask any questions he or she has for you, so that everyone walks out of the room with the information they would need to make a decision on an offer. Are the questions about strategy, career progression, pay, coffee quality, weekend emails? You can learn a lot from what questions candidates ask in what order.

Please leave a comment if you have feedback or suggestions on this post. Happy hiring!

Be Thankful for the Worst Moments of Your Career

Thanksgiving is a fascinating holiday because it unites the American population — all too easily fragmented into racial, ethnic, religious, and socioeconomic tribes —  with a day of celebration characterized by overeating, football, parades, sitting in traffic, and shopping. God Bless America.

Memorable, perhaps not for the intended reasons
Memorable, perhaps not for the intended reasons

Thanksgiving also prompts us to reflect on the aspects of our lives for which we are grateful. If this habit of reflection and gratitude is not already part of your regular routine, the holiday is a convenient trigger to start. Since so many other pundits will focus on being thankful for the happy, fluffy stuff (like kittens, having a Twitter account that isn’t censored by the government, etc.) I decided to take a different angle and prompt you to reflect on the worst moments of your career; the moments that we so easily sweep under the rugs of our memories.

Why be thankful for the worst moments? Two main reasons:

  1. Without the worst moments of failure, our best moments of success wouldn’t shine. Few of us will experience the extreme “rags to riches” arc of Dhirubhai Ambani (founder of Reliance Industries, one of India’s largest firms) or the drought-erasing victory of the 2004 Red Sox, but every moment of success is more enjoyable in contrast to relative failure.
  2. Our mistakes offer meaningful lessons and accelerate our growth. One of Ray Dalio’s principles is “pain + reflection = progress.” It is easy to read about concepts in books and articles, but the most powerful case studies are the ones we live through.

We’ve all had “forgettable” moments in our careers: the presentation that ends with confused silence, the spreadsheet error that gets through to the Board recommendation, the budget models that go through countless revisions over many bleary eyed weekends (to name a few of mine). Here’s an approach to making the most of those tough experiences:

  • First take a few moments to feel, truly and vividly, the painful feelings of failure and disappointment. Afterwards, it’s much easier to move past the negative experience without lingering regret or embarrassment. Don’t despair: life goes on. You are not an inherently bad person because of a poor choice or error.
  • Then reflect on what faulty reasoning or gap in skills led to the mistakes. We can take on new challenges with confidence provided by new skills and perspective. Be thankful that this failure occurred as early in your career as it did – you will now benefit from the learning for the rest of your days.

Just like roses can’t exist without manure, and a delicious turkey dinner can’t exist without a sink full of stinking dishes, professional blunders are an inevitable part of any career. Be thankful for the learning opportunities they provide, and soak up the satisfaction of success even more fully when it arrives.

Image credit: Business Insider

Is your job as hard as you want it to be?

First: a Veterans/Remembrance Day moment of appreciation to all military veterans out there. The rest of us will never actually understand the level of service and sacrifice that you made. Thank you, truly.

Now, some of that leadertainment you came here for. Many people find themselves restless at work, struggling to find balance. If you are, like me, a modern day corporate Goldilocks seeking professional balance that is “just right,” perhaps this framework will be helpful to you.


  This is not what I meant by “hard.” Entertaining, though, on a few levels.

What I’m proposing is that a job can be hard on you physically, mentally, both, or neither. Ok, I won’t wait up late for the Nobel phone call, but perhaps you haven’t taken stock of your job this way before, or thought of ways to change the balance.

Why is your job hard?
Why is your job hard?

Once you’ve placed your current job on the matrix, ask whether the role fits what you want from your career at this stage. Maybe your commitments at home are growing and you’d happily take on some career Atrophy for more bath time with the kids and date nights with your spouse, or the flexibility to start volunteering. At the other end of the scale, perhaps you are a recent empty nester and are ready for the Exhaustion of a tough growth challenge with a startup organization. Many of us are very happy with Heavy Lifting or Deep Thinking roles, once have found the right match for our strengths.

In an upcoming post, we’ll dive in to the concept of purpose at work. For now, think about why your job is hard, and whether you are satisfied with the answer. If not, collect your thoughts and reach out to your manager, your peers, and your team, and make a plan to change it for the better.

Fired? Ready, Aim… Preparing for your next career transition, no matter how urgent

One day, you will walk into your home without the job you had when you walked out. That day might be very far off in the future, or might have been just a few days ago. Regardless of how much time you have to prepare, here are a few broad steps you can take to be in the best position to transition to the next phase of your career as smoothly as possible.

DSK will need a different type of weak ties in the future
DSK will need a different type of weak ties in the future

This topic should be on a few people’s minds, considering that for the past few months in 2012 more than 4 million people in the US, or >3% of total employment, have lost their jobs each month…and whoever called economics the grim science hasn’t seen the “JOLTS” report that provided these statistics!

  1. How long can you hold out for a great job? Understand your risk tolerance, burn rate, cash position, and “reinforcements” (tapping into credit, retirement savings, family loans, organ sales*, etc.) as you deplete cash.
  2. What is your value proposition? Clarify how you are going to market your capabilities to prospective employers. Remember to start with why, and understand how the next role helps close the gaps towards your medium term ambitions. The written form of the value proposition is your resume, plus your online profile. Keep in mind that usually these will be scanned quickly by someone other than the hiring manager, so take advantage of available resume writing advice to update yours.
  3. How strong is your career pipeline? Just like in sales, you need a network of contacts, a set of prospects to “close” and a steady stream of new leads coming in each week. Remember that weak ties are the most valuable (dork version of same concept) connections in your network. Until you get to the point of submitting an application: don’t ask for jobs, ask for connections (people will offer a job if they know of a fit).
  4. Are you talking to people more than looking at a screen? In the world of tablets, smartphones, and apps, we forget that there are humans out there that want to shake your hand and look you in the eye before they hire you. Look for ways to follow your passions and build weak ties to enhance your job search.

Look for expanded posts on each of these topics in the future. What have I left out? Where am I wrong? Leave a comment, thanks!

* don’t sell your organs. Not even the musical kind.
Image Credit: Richard Drew