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.

Stressed? Here’s the MBTA Approach

With the recent ongoing snow storms in Boston, we’ve all been feeling stressed. There are many stress management techniques to choose from, and I thought looking at the MBTA as a case study would provide another perspective. Hey, they are a $1.8b revenue company that managed to turn a profit last year, so they must be doing something right…right?

The Onion recommends a similar technique to improve health and professional satisfaction
The Onion recommends a similar technique to improve health and professional satisfaction
  1. Pretend nothing’s wrong while your performance suffers. This includes telling people about problems long after they’ve happened, providing hopelessly optimistic expectations, and general denial that anything’s wrong.
  2. Shut down completely. Give people a few hours’ notice, and then just stop doing your job for a while. Maybe you will take the opportunity to resign from your job. If, however, you’ve chosen a temporary shutdown, continue to step 3.
  3. Resume underperformance combined with abject denial of any problem. Maybe you’ve drawn inspiration from the thought that every crisis in life is temporary. Maybe you’ve realized you are a publicly funded monopoly without any real consequences for failure. Either way, keep your head high while you flail!

We can learn from any case study, whether it is a success or failure. Hopefully you’ll find a more effective stress management technique on your way to career fulfillment. Have any suggestions? Leave a comment.

Are you a normal thinker in a power-law world?

Along with celebrating the holidays, eating cookies, catching up on sleep, eating cookies, and doing fun projects with the kids (did I mention the cookies?), one reason I enjoy the year-end is the chance to chip away at the stack of unread books piling up in my house. A particularly thought-provoking book in this year’s batch is Peter Thiel’s Zero to One, which has earned a spot on my recently revised Essential Reading List.

This post is not a book review, but rather a highlight of an idea Thiel introduces early in the book and has appeared in my daily thoughts since reading it. He reminds us that conventional Western thought trains us to think of outcomes as following a normal (random) distribution, but in fact both the natural and business world follow a power law distribution. Accepting this re-framing of the world around us is easy in theory, and changing our choices in life as a result can be very difficult.

Some are mean, some have no mean
Some are mean, some have no mean

The idea itself is not original – from the application of mathematical theories to the emerging computer science field in the 1950s, to Malcolm Gladwell’s 2006 New Yorker article, to Taleb’s Black Swan – but Thiel’s framing of the concept, and its implications, is novel.

Many of us are taught to value breadth over depth, and to avoid “placing all of our eggs in the same basket.” We are coached to believe that well-roundedness is a virtue but hyper-specialization is “weird.” The entire premise of the liberal arts education system, from classical to modern times, is to provide foundational knowledge in a broad range of topics. [Personal note: not all institutions follow this mantra. The feedback I heard after being rejected from MIT’s undergraduate engineering program was that I was “too well rounded.”] As students and professionals, we are graded on a curve (the normal distribution). We are advised that portfolio diversification is the safest and most profitable theory of investment.

But strategy is about trade-offs. A business must choose to specialize in a certain market, geography, or product domain in order to reduce competition and increase profit. We cannot diversify our professional lives by being partially invested in many careers. At some point, we must choose to specialize in a function, industry, or growth stage in order to excel.

Sure, it’s interesting to think about whether phenomena like marathon finishing times, portfolio company performance, emissions, or health care spending follow a normal or power law distribution (at least for a few moments). But how can we apply this new way of framing the world? Here are a few ways to put this theory to action in life:

  • Think, plan, and go deep – from an early age. Find out what you (and your kids) are passionate and talented in, and build expertise. The most knowledgeable and talented people in any discipline are always in demand, regardless of market cycles.
  • Take risks with definite outcomes. Be certain, which means being certainly right or wrong, not indefinitely indeterminate. Too many of us hide behind a fear of failure and instead drift along in the middle of the pack without achieving much.
  • Concentrate your investments in a much smaller number of areas: in your professional pursuits, and your personal interests. As the new year begins, instead of asking yourself “what else can I start doing?” think about what you can stop, in order to focus your mental and physical energy on the few things you do best and enjoy most.

Does this resonate with you? Sound completely crazy? Leave a comment and let me know! Regardless, have a happy, healthy, and prosperous 2015.

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.

Hold on, were you just trying to delegate?

Let’s go back to the basics here folks. Whether you have 3 months or 3 decades of leadership experience, an essential skill to keep your team effective and engaged is delegation. A wise man once said “delegation is about deciding what you don’t do, and prioritization is about deciding what no one does.”

Cliche aside, the skill required in effective delegation is assigning tasks to your team members that achieve leverage and learning. Terry Pearce has a classic (i.e., VHS!) training video about leadership speaking in which he tells the story of dropping off his daughter at college: the main message about delegation is that unless it hurts, you haven’t delegated a large enough task. But what does this look like on a graph, you ask?

Successful delegation takes self-awareness on the part of the manager and the team
Successful delegation takes self-awareness on the part of the manager and the team

The ideal level of delegation gives the team member enough autonomy to achieve a task that requires a slight “stretch” of skill (i.e., learning) to complete at the required level of quality. Yes, the manager could have completed the same task at a higher quality level (per unit time), but the free time created in the organization allows the manager to take on a higher complexity task that, presumably, no one else below him or her in the team could achieve. This is what I mean by leverage.

Locating this curve for each employee/manager combination requires self-awareness and feedback on both sides. The team member needs to raise awareness of his or her skill level, and the manager needs to raise awareness of his or her level of control or autonomy with delegated tasks. From the manager’s perspective, you must be willing to sacrifice control for the sake of leverage and learning, without setting your team up for failure. Staying too far to the left is demeaning and stifling for your team. Too far to the right, and you will assign tasks that my former (rugby loving) manager would call a “hospital pass:” drop it and your team loses, catch it and you’ll get knocked out.

As a manager, signs that you are too far to the left on the curve include:

  • you ask a team member to circulate a document for feedback among a group, and then scold him or her for sending an email to that group before letting you proofread it
  • you ask a team member to facilitate a meeting, and then chime in after every one of his or her comments with a “clarification”
  • your team members have asked (directly or indirectly) for more responsibility and authority to set direction in achieving the team’s goals

As a manager, signs that you are too far to the right on the curve include:

  • many of the tasks you assign need to be reworked at the last minute
  • few team members volunteer for tasks on offer because they are intimidated by the complexity of the task or the risk of failure

So, I challenge you to use this post as a prompt to reassess your ability to delegate. Have a conversation with your team members to reach alignment on where you are on the curve. Find low-risk ways for your team members to fail constructively, and watch the benefits of learning and leverage accumulate.

There are only 4 jobs in business: which are you pursuing?

Here’s a quick post to summarize a conversation I had a few weeks ago about my own career path (thanks, Michael Schreck). Hopefully, this framework will be useful for other people exploring career development options.

At some point in our careers, we must choose to specialize. For some people this occurs very early, for example entering an apprenticeship at age 16 to learn a skilled trade. Others make this decision after working in the same functional role across industries, or in different functional roles in the same industry, or after a stint in consulting.

So what are you going to specialize in? Let’s simplify by stating that all business roles follow one of four tracks:

  • Fund raisers: These people raise funds to support transactions and investments, typically through private equity funds, hedge funds, exchange traded funds (ETFs), mutual funds, or debt/equity offerings. You will succeed in this job if you love building pitch books, are already a famous and massively wealthy investor, and/or are such a fantastic salesperson that you can convince people to part with millions of dollars for the chance to own a sliver of something that won’t exist for years.
  • Deal makers: Once the funds have been raised, it’s time to put the dry powder to use by buying something. While many corporate development teams, venture capital & private equity groups manage deal flow and close transactions on their own, the deal makers that grab the largest share of the spotlight are investment bankers. Spending an unsustainable percentage of your life revising pitch decks is also a hallmark of this career path. but for those who succeed in riding the M&A waves, countless bespoke suits and limited edition watches await.
  • Profit takers: Once the fireworks around the deal have faded, someone’s got to execute the strategy. The owners of any business, ranging from a sole proprietorship to a limited liability company to a corporation, bear the risk of the ongoing operation, and also have the first cut of the retained earnings. [Updated thanks to a helpful comment by Pete Bondi] The owner’s role is to create: new products, services, and content that attract customers and retain competitive advantage. Recent studies show that most CEOs of large corporations have finance backgrounds, and all have had to climb the ladder by succeeding in operational and sales roles, in addition to any functional experience. US tax return data shows that higher earners are more likely to be self-employed, so the appeal of “owning something” can also be quite lucrative.
  • Advisors: After some feedback and discussion about this post, I’ve added a fourth category to include career consultants. Now anyone who has run a consulting business would put themselves in the third category above, but there are plenty of talented people who can lead long, fulfilling careers as non-partner, subject matter experts on the consulting track, without ever participating in the execution of their analyses.

Which path are you on? Why? Are you at an inflection point in your professional development? Sometimes eliminating an alternate path can help increase dedication to the path you’re on – so take a good hard look at the grass on the other side of the fence and make your decision.