The 8-Fold Path to Enlightened Leadership


Like any skill, becoming a great leader is simple in theory, but not an easy path. It’s a matter of identifying the key behaviors of great leaders, and practicing them intelligently and diligently until they have been mastered. So what is it that great leaders do that makes them so great at leading? In this article, I will weave together the various observations I’ve made on leadership into a unified prescription for developing yourself as a great leader called the 8-Fold Path to Enlightened Leadership.

Similar to the 8-Fold Path of Buddhism, the Enlightened Leadership Path is comprised of three logical stages derived from the definition of leader. I’ve previously defined a leader as “someone who discovers, develops, or imagines something new, and then influences people to make changes that make the new thing real.” The three stages of the 8-Fold Path correspond to the three main activities in this definition: Imagine, Inspire, and Innovate. The three stages and eight individual steps are illustrated in the following diagram and described in detail below.


The Imagine stage is all about coming up with the “big idea” – the something new that will positively affect people after you, as a leader, provide the spark to make it a reality. The three steps of this stage are to: 1) Listen, 2) Challenge Assumptions, and 3) Ideate.

“Almost everyone knows something or has some insight – listen before you speak.” – Father of David Boies, “Superlawyer”

1. Listen. Learning to listen is the most common advice given by seasoned leaders, and rightly so. As I noted in Do You Want to Know a Secret? Listen, “listening…lets you be dynamic, limber, and agile. [It] fundamentally allows you to be in the moment, consider all options, and actively self-correct.” Listening also has “many obvious benefits, like exposing you to a broad range of ideas, building trust and rapport, and establishing a common narrative.” In the Imagine stage, it’s critical that your imagination be able to draw upon a vast array of ideas and concepts, things you can only have access to if you’ve “kept your ears open.” Of course, listening goes much deeper than just paying attention to others when they speak, true listeners express an openness and awareness that informs them at many levels. See the above article for more details and suggestions on how to develop your listening skills.

“When everybody knows that something is so, it means that nobody knows nothin’.” – Prof. Alois Xavier Schmidt, City College of New York

2. Challenge Assumptions. Challenging assumptions should be done of both your own ideas as well as others’. A simple way to do this is to get in the habit of repeating any statements of fact or opinion, adding the phrase “assuming ______,” and then filling in the blank. For example, “We can only build 1000 units, assuming our supplier can only ship one container of supplies.” Or, “Our competitor will only sell 10% of our sales volume this year, assuming they don’t lower their price point.” Once you get these assumptions out in the open like this, you should then challenge them. Why can’t you ask for more than one container, or switch suppliers? What’s stopping your competitor from lowering their prices? Challenging assumptions like this opens up possibilities and prepares you for full-bore brainstorming.

“Ideas are a dime-a-dozen, which leads to the intriguing implication that most ideas are worthless, and a precious few represent the nuggets we all search for.” – Chris LuVogt

3. Ideate. As I’ve noted previously, some people have a natural talent for immediately seeing the larger potential of great ideas, but this kind of ‘right-brained’ thinking does not come easily to everyone. Luckily, there are many ideation techniques that anyone can practice to formalize the process of developing and vetting ideas. I present one such framework in my two-part post on Thinking Big, namely the “Summarize, Generalize, Hypothesize, Synthesize, Prioritize, Evangelize” methodology. There are many other frameworks one can use to brainstorm, but the end goal of this step is to generate a realistic, substantial “game-changing” idea that you can then move forward with in the next two stages.


If you have a truly great idea, chances are you’ll need some help to make it real. The Inspire stage of the 8-Fold Path is all about developing the character you need to be able to convince others to jump on your bandwagon. According the model of great leadership I developed in Earning the Leadership Merit Badge, character is the distinguishing feature between an effective leader and a great one. The three steps of this stage revolve around developing the following three key skills and character traits: 4) Mastery, 5) Respect, and 6) Passion. Taken together, these give you the authenticity and integrity to be truly compelling, so you don’t have to rely solely on others seeing the merits of your big idea in isolation.

“If you’re going to be significant at something, you’ve got to learn it from the ground up.” – Father of Ron Johnson, CEO JC Penney

4. Mastery. Mastery provides the legitimacy you need in order to establish a fundamental bond with the people on your team. Let’s face it, if you’re trying to lead a group of people, but you have nothing in common with them, then you have nothing on which to build trust and commitment. Mastery, most critically of the core competency that gives your team its competitive advantage (engineering for engineers, selling for sales, etc.), goes an incredibly long way towards giving you both the “street cred” to lead, as well as the necessary fundamental skills to execute during Stage 3 (Innovate). It allows you to dive deep when problems arise, applying that attention to detail that your followers expect and deserve. As I said in The 4 Principles of Great Leader-Chefs, true masters do not just practice what they know and hold themselves to high standards of excellence, but they also challenge the prevailing assumptions and try to improve both their practice of the craft as well as the definition of the craft itself. In this way, they always maintain legitimacy and relevance, and the ability to lead others.

“People should be respected and trusted as people, not because of their position or title. Frequently, position or title do not reflect the true merits of a person.” – Mother of Herb Kelleher, CEO Southwest Airlines

5. Respect. Whereas mastery engenders respect from followers, it is critically important for a leader to return the favor. This kind of respect for others should be the default behavior of anyone who desires to lead, towards everyone they work with. It reflects a deep-seated attitude that assumes everyone deserves an opportunity to discover how their strengths can best contribute to the overall success of the team. It doesn’t mean that non-contributors get a free ride. Rather, it means everyone gets a fair chance to shine. Respect and compassion go hand-in-hand, and one of the easiest ways to learn them is a simple mental practice I mentioned in The Waiting is the Mindful Part – simply randomly (and silently) wishing happiness for the people you meet or even just see. You can start doing this just once or twice a day, but because it is so addicting, eventually it will become such a habit, you’ll do it for everyone.

“You should do what you’re good at, and do what you love.” – Danny Meenan, Reporter

6. Passion. Passion is a simple thing – if you’re not doing or thinking about something in your “down time,” you’re not passionate about it. Passion is not something that can be faked, and without it, you will lack the integrity necessary to keep followers for very long. You’ll also lack the driving force necessary to keep you striving for your goal. Ask yourself, “If there was no external force keeping me engaged, would I still be doing this?” If the answer is “No,” you might as well stop now and save yourself and your follower’s time – you’re not being authentic and true to your inner self.


So you’ve discovered something great and inspired a team to help you create it – how do you move forward and actually innovate? What techniques can you use to execute and make your idea a reality? The last two steps of the 8-fold Path are there to help you make things happen: 7) Leverage Strengths while Understanding Limitations, and 8 ) Challenge Yourself and Others.

“Develop your ability to leave your own ego at the door and to recognize the skills and traits you don’t possess and that you need to build a world-class organization.” – Warren Bennis, Scholar

7. Leverage Strengths while Understanding Limitations. Strengths and limitations apply to both yourself and those you are leading. As Jim Collins classically put it in Good to Great, you not only have to get the right people on the bus, but you have to make sure they’re sitting in the right seats. Great leaders are always evaluating their followers and determining whether skills and strengths match roles and responsibilities. As I said in Synthesize, Prioritize, Evangelize, “Not everyone on the idea-backing team should also be on the implementation team. Make sure that any backer you carry over has the requisite skills, knowledge, passion, and/or position of authority to be able to contribute.” This represents another situation where awareness and listening, without judgment, play key roles. Great leaders develop a habit of constantly measuring the performance of both themselves and their teams, understanding how roles need to change over time, and not hesitating to rebalance what people (including themselves) work on, in order to play to their strengths and not expose them to situations that expose their limitations.

“You can’t always control what happens to you…but you can control how you respond – you should never quit.” – Mother of John Hickenlooper, Gov. of Colorado

8. Challenge Yourself and Others. Great leaders have three characteristics that keep them and their teams moving towards their goal: Decisiveness, Impatience, and Persistence. Decisiveness sets the direction of movement, impatience sets the pace of movement, and persistence sets the expectation of the achievement of the goal. The leader sets all three of these for themselves and their team, dynamically and in such a way as to ensure forward progress. The best leaders are ones who have practiced decision making to the point where they are comfortable making decisions nearly instantly, who have a bias for action developed by always assuming that positive steps can and should be taken, and who have practiced failing or hitting roadblocks but continuing anyway. As I’ve mentioned before, meditation is one particularly effective way to train this last characteristic, persistence. Leaders who exhibit these traits are the ones that push their own limits and the limits of their team, challenging all involved to be their best, without overtaxing anyone.

Taking the Path

Although the three stages and their individual steps roughly follow each other sequentially, it should be clear that some or all of the activities in each stage or step will overlap with those in other stages and steps. In the above diagram, this sequencing is implied by the arrows leading from the top to the bottom of the diagram.

I’ve tried to give practical suggestions for most of the steps, but I consider this just the beginning of the development of this model. In future articles, I hope to flesh out each of the steps in more detail. Any suggestions or pointers are more than welcome. And for pointers on how to practice (in general), I highly recommend Jesse Bridgewater’s Practice Doesn’t Make Perfect.


3D Spherical Feedback – Redux


SphereLast month, I wrote a short blog post outlining a new technique for getting personal improvement feedback that I called 3D Spherical Feedback. I directly solicited several hundred of my friends, family, and professional colleagues from across the years to answer four short questions about me. The results have been enlightening, insightful, and yes, quite funny at times. More importantly, the process helped me reconnect with a lot of people that I had lost touch with. In this post, I will analyze both the process itself as well as the results for me personally. If you are more interested in knowing what I learned about myself, skip ahead to the section entitled Personal Results.

Design and Method

I used Google Forms to create a six page survey. On the first page, the respondent was asked for their name (optional), as well as primed to remember the most salient experiences they shared with the subject (me). The next four pages corresponded to the four questions from Want Great Feedback? Ask These 4 Questions, also shown below. The last page asked whether the respondent would like to have a follow-up conversation, as well as whether they had any further questions, comments, concerns. In a handful of cases, the questions were asked in person instead of online.

The Four Questions

  1. What do you think is Chris’s greatest strength?
  2. What do/did you appreciate most in your interactions with Chris?
  3. What do/did you wish Chris did more or less of?
  4. What gift would you like to give Chris?

Respondents were solicited in three ways, in the following order: first via posts to social media sites (LinkedIn, Facebook, G+), then via bulk emails to a list selected by the subject, and finally, via direct emails to a shorter list culled from the bulk list by the subject. As would be expected, response rates improved as solicitations became more personal and directed. All in all, somewhere in the neighborhood of 500 participants were solicited, well over 200 viewed the survey, and 123 responded. Each respondent received a personal note of thanks from me.

The online survey was designed as a step-by-step survey to better mimic an in-person interaction, where a question is asked and answered before the next question is presented. Likewise, the question about identity was front-loaded to mimic an in-person interaction. A small number of respondents expressed dissatisfaction with this design, wanting instead to see all of the questions and being able to make the anonymity decision after answering.

A number of solicited participants also expressed dissatisfaction with either the specific questions used, the impersonal nature of the survey, their lack of sufficient knowledge of the subject to provide an informed opinion, or the implication that they should not remain anonymous. These reasons (and presumably others) account for the drop-off between the number of people viewing the survey and the number who completed it.

Results & Discussion

Nearly all respondents answered all four questions. 15 of the 123 decided to remain anonymous. Only 5 specifically wanted a follow-up conversation, 16 specifically did not want it (this corresponded strongly with anonymity), and the rest left it up to the subject.

Half of the answers were ten words or less, with only 6 of the 492 (=123 x 4) answers exceeding 100 words, and the median answer length was 10 words. This is likely partially a result of the questionnaire, which specifically instructed the respondent to answer quickly, although a large text box was provided for answers of any length (the longest received was over 600 words).

Roughly 40% of the respondents were friends or family of the subject, 48% were colleagues, and 12% were both.

As a rule, the responses were overwhelmingly positive in tone. There are at least four large sources of bias that help explain this. First, the questions themselves are phrased in such a way as to elicit a positive response. Second, there was a selection bias introduced by having the subject choose which participants to poll and follow up with. Third, a self-selection bias was also likely in play, in which only respondents who had something positive to say bothered to respond at all. Finally, because the respondents were a mix of friends, family, and colleagues, yet the questions were more geared towards a work environment, it was not uncommon for friends and family to elect to not give a substantive response. This happened particularly with question #3, “What do/did you wish Chris did more or less of?”, which was often answered “Not sure” or “Don’t know” by personal acquaintances.

Respondents were also coded by relative strength of relationship to the subject: a function of how many years they had spent together, how long it had been since they had been in close contact, and how close their relationship had been. This relationship strength was later used in the textual analysis of the answers (below) to weight how much to count the text of the response.

In terms of design, I see a few opportunities for improvement. Moving the “Name:” question to the end of the survey would likely assuage respondent’s discomfort and may improve response rate. Choosing a different set of questions, more geared towards personal relationships, would also likely improve responses from that segment of respondents. Most importantly, however, a more personalized plea for participation, along with a deadline, would likely go the furthest to improving the quantity and quality of responses.

Personal Results

My goals for this exercise were twofold: one was to experiment with a new technique for gaining feedback. Fundamentally, I was trying to see if short responses from a large number of people from many relationship categories and phases of life could provide a more textured, nuanced picture than the typical low-quantity, detailed feedback from current co-workers only. The second goal was to get feedback so that I could get a more clear picture of who others thought I was, and to use that feedback to help guide my personal development, and even my career path going forward.

I received over 10,000 words of feedback from people who have known me since I was born through people I’ve only first met in the last year. From people whom I’ve worked closely with for years to people who only knew me briefly and in passing. I’m still going through them and will likely be doing so for months or years to come. As mentioned above, the feedback was overwhelmingly positive, to the point of making me feel almost narcissistic in having undertaken the exercise. If I were to do it again, I’d definitely change the questions to try to elicit more constructive feedback.

To try to get a gist of the most important points, I’ve run the feedback through some textual analysis and produced some “word clouds” (below, thanks to Word Cloud Generator – Jason Davies). Two of these are summaries of colleagues’ comments, and two are from friends and family. They also come in two flavors: single words or sentence fragments (these are cut off in the middle of words). I was amazed at what some people said, and that some of what I considered my more hidden strengths were the first things to come to mind for some.

Word Cloud - Colleagues
Phrase Cloud - Colleagues
Word Cloud - Friends
Phrase Cloud - Friends

Reading through the responses, there is no doubt in my mind that this exercise has been eye-opening and immensely useful for me. In terms of the methodology, I don’t think this would replace the typical 360 feedback used in corporate settings, as it does not address the particulars that was designed to address. Nevertheless, it is a powerful way to expand the feedback net to gain insights that are more about the whole person, and not just the professional persona we put on at work.

Thanks to all who took the time to respond — I will be forever grateful for both your thoughtful responses and for the “gifts” you gave. I was overwhelmed by by your kindness. By far the most common gifts were some combination of health, happiness, love, peace, and friendship. I also received at least a dozen books, plenty of wine, several job offers, and a bunch of vacations. Not to mention the child(!), 3 puppies, grain of Tibetan sand, Japanese vase, and book of Persian poems. But the gifts that made me pause and think the most were the numerous offers of time, the wishes that I find a suitable challenge, and the hopes that I could find my voice and a become the leader some of you seem to think I am. It is these gifts that I will be focusing on making a reality in the coming days.

And thanks for the one box of chocolates — of all my vices, this is one I hope to never give up!


3D Spherical Feedback


I recently read: Want Great Feedback? Ask These 4 Questions* by Brian Rumao, Chief of Staff to LinkedIn’s CEO, Jeff Weiner. It got me thinking about 360 Degree Feedback, and how to take it one step further.

Traditional corporate feedback systems flow downward — managers rate their reports on some regular fixed schedule (e.g., quarterly or annually). 360 Degree Feedback is intended to provide a broader view to the person receiving the feedback, soliciting input from the person’s manager(s), directs, peers, cross-functional partners, and even internal and external clients. You can view it as the collection of people in a person’s “work circle” — thus the name 360 Degrees. Getting 360 Degree Feedback is expensive and time-consuming, and as such, is typically done infrequently — on the order of only a few times during a person’s career, if that — and only for managers or executives.

As helpful as 360 Degree Feedback can be, though, it’s still very “two-dimensional.” It focuses almost exclusively on the interpersonal relationships that play a part in the person’s work life. But so much of our lives are spent outside of work, relating to people we don’t formally work with. And as we move more and more into a Knowledge Economy, and possibly even a Purpose Economy, work and personal lives are constantly being more intimately intertwined. We can, in fact we should, be asking anyone we have a relationship with how we are doing.

Clearly, asking everyone you know for in-depth feedback does not scale. But as I’ve thought about this, I began to realize that we may be able to trade off quality of feedback for quantity, and at the same time, be able to to expand the circle of feedback givers into a sphere by including friends, family, and non-work colleagues. The law of large numbers could help ensure that even though the feedback is low-resolution, it would still accurately reflect the truth. And more importantly, that truth would be truly 3-dimensional and “spherical” — coming from all perspectives.

So here’s the experiment I’m asking you to help me with. If you’re reading this, chances are good that you know me. I’ve taken the 4 Question Framework and put it into an online questionnaire. Before reading Rumao’s article, can you take 2 minutes, right now, to answer the 4 questions about me?

>> Take the Survey Here <<

I’d be more than happy to have a follow-up discussion with you in person, via video chat, or on the phone. And I promise to write a follow-up article describing, on a meta-level, how the experiment worked out.


* Here’s a link to the original article, if you want to read it in depth – I do recommend it!



Do You Want to Know A Secret? Listen…


What would you reply if someone asked you, “What’s the secret to a happy life? What’s the single most important life skill that I should develop?” Would you say it was discipline, persistence, conscientiousness? How about compassion, gratitude, or humility? Would you suggest they develop their empathy or instead focus on being as efficient as possible? I’m increasingly of the opinion that listening is the most critical core life skill. Listening acts as an enabler and foundational component for most of the other useful life skills.

Listening showed up at the top of the list of “best advice” when I analyzed CNN Money’s articles on the topic in Thrice Filtered Leadership Wisdom. Listening is also typically mentioned or lauded by anyone teaching leadership or communication skills. For example, in How To Win Friends and Influence People, Dale Carnegie encourages the reader to be a good listener, let the other person do a great deal of the talking, and try honestly to see things from the other person’s point of view. Likewise, one of Stephen Covey’s Seven Habits of Highly Effective People is to “Seek First to Understand, Then to be Understood.” Of course, how can you possibly understand someone else if you haven’t listened to them?

Few would argue the importance of listening, but what makes it critical and foundational? What is the power of listening? Aside from the many obvious benefits, like exposing you to a broad range of ideas, building trust and rapport, and establishing a common narrative, listening also sets you up to build and develop the other life skills that in turn make you happier, healthier, and more productive. Here’s how…

Awareness and Agility

On the surface, listening is just “paying attention to sound,” but of course there is much more to it than that. Auditory listening is just one manifestation of a more general type of listening, namely being aware, being conscious, and paying attention. As I mentioned in Living the SWEET Life, Daily, awareness lets you short-circuit your habitual thought processes. This in turn leads to agility: the ability to rapidly adjust based on the current state of affairs, with little effort. Thus, listening, and paying attention in general, lets you be dynamic, limber, and agile. Awareness fundamentally allows you to be in the moment, consider all options, and actively self-correct.

To understand its power, it’s helpful to think about what listening is not. If you are not listening, then what are you doing? Usually, you are absorbed in your own thoughts. You are distracted, your attention is elsewhere, and not on the person who is trying to communicate with you. If you are not aware of what’s going on and being said, and you only check in haphazardly or reactively, the input to your decision making apparatus (i.e., your brain) is limited and biased, making it more difficult to react in a timely and appropriate manner. Why would you starve your brain of potentially useful information at the outset, without even considering it? Are your own thoughts really that important and productive?

Other Ways of Listening

If listening leads to agility in communication, imagine what it could do for you when you apply it to more than just conversations. What does that mean? Communicating with others is just one possible modality of gathering information about your world, and other people are just one source of information. You can get so much more from using all of your senses, and focusing not just on others, but yourself and your environment. For example, what if you decided to “listen” to what your nose and tongue were telling you, as you ate or even just as you walked down the street or met with another person? What if you could really absorb and be aware of everything in your visual field of view, including the facial expressions and body language of people you were talking to, as well as knowing exactly what’s around you physically, how it’s moving, and what it’s likely to do next? What if you decided to listen to your somatic sensations, really listen to your body? Wouldn’t it be amazing if you could sense the smallest twinge of pain or really be able to notice when some part of your body was inflamed, or be aware when your body has dumped cortisol and adrenaline into your bloodstream? Most importantly, what if you listened, really listened, to your own thoughts and emotions? You might be surprised, or even enlightened, by what you hear. This kind of awareness is not the stuff of superheroes and science fiction. It is achievable and, remarkably, not that difficult to learn, although it takes lots and lots of practice.

Becoming an Active Listener

We spend most of our lives learning to habitualize and ritualize our thoughts, beliefs, and actions. But this approach of laying down default behaviors and then strengthening them with repetition over time is exactly the opposite of what makes us most effective at dealing with the dynamic, changing world we live in. Listening, paying attention, and being aware of our inner and outer world, in every way possible, is what fundamentally enables us to be good communicators, effective leaders, and agile, facile contributors to ourselves and others. It places the conscious mind back into the loop. Listening is one of the few habits we would all do well to ingrain deep in our psyche.

Unfortunately, it’s all too easy to lose the habit of being a great listener. How do you learn to listen? It turns out to be disarmingly simple – learn to listen by practicing listening! For example, here’s a simple exercise you can do to practice auditory listening: whenever you are conversing 1-to-1 with someone, and you are about to inject your opinion, experience, amusing anecdote or advice, simply stop and hold it back. Let the other person continue until they’ve completely spoken their piece. Then (and only then) return the favor, but before expounding on your own personal thoughts, try to let the other person know you’ve heard them by simply summarizing what they’ve just said (this is sometimes called active listening), and let them respond. You may end up never getting to make your point, and that, in itself, is the point.

Inward Listening

It’s been said that the greatest gift you can give someone is your undivided attention. Imagine, then, the enormity of the gift of learning to listen to yourself. If you could hear and understand all of the activity going on in both your body and mind, you could be agile about adjusting to it, developing it, and improving it. This is what I meant earlier when I alluded to listening helping to make you happier, healthier, and more productive. True listening also involves developing the ability to attend to all sources of information (one’s self, others, one’s environment) from all modalities (senses, emotions, thoughts). Again, to learn to do this, you must practice. Luckily, this is already something that’s been well understood for thousands of years, and the techniques for practice are meditation and yoga. Or, if those sound too intimidating, just simply practicing mindfulness (it really is quite easy).

Discipline, persistence, conscientiousness, compassion, gratitude, humility, empathy and efficiency – all of these are laudable traits. And all of them are amplified by the agility imparted by listening and awareness. When will you start your listening practice? It’s easy, and only takes a few seconds or minutes each day. Here’s a recent article to help you get started. And here’s a Beatles song to inspire you…


Thrice Filtered Leadership Wisdom


As I prepare to attend the Wisdom 2.0 conference next month, I’ve been thinking a little bit about how to go about extracting the sum total of all humankind’s wisdom from this vast collection of information we’ve created called the World Wide Web. It seems like it should be do-able, although likely not easy. After all, wisdom is just a final endpoint along the classic data, information, knowledge, wisdom progression, and we’re already well along the way to encoding all of human knowledge via artifacts like Wikipedia and Google’s Knowledge Graph. One logical starting place would be to crowdsource the collection of wisdom. In my experience, however, typical crowdsourcing solutions (think: Yelp or Netflix) suffer from a lack of appropriate weighting of votes. I’m much more satisfied with systems that rely on aggregating the knowledge of subject matter experts (e.g., Michelin or Rotten Tomatoes), rather than systems that try to discern a quality signal by collecting the wisdom of the crowds. You can think of these opinions as “twice filtered” – first by the SME’s, and then by the algorithm.

When CNN Money published The Best Advice I Ever Got and The Best of Our Best Advice, in which they polled seasoned and successful business leaders to offer up their most useful nuggets of wisdom, I took note – here was some already twice-filtered wisdom (first by the adviser and then the advisee). And while the anecdotes and backstories provided in those articles are interesting and make the wisdom more tangible, I wanted to see if there were any common themes across the 41 interviewees. I talked briefly about one technique I used to summarize all of this wisdom in A Simple Semi-Automatic Text Summarizer, but that analysis only scratched the surface and missed a few key themes. So I’ve dug into the articles more deeply, categorized and prioritized the largest themes, and present them below in order of importance – a third layer of filtering. It’s gratifying to see that many of the most important themes like listening, mastery, passion, strengths and limitations, and persistence are all topics I’ve touched on in other leadership articles in this blog. I hope to follow up and expand on many of these themes as well, but in the meantime, I just present the filtered and grouped key observations. (Note: I paraphrase many of the quotes, and I attribute the advice to the original adviser when I can, and not the advisee.)

1. Listening

  • Listen to your employees, be completely engaged when you do so. – Herb Kelleher, CEO Southwest Airlines
  • Almost everyone knows something or has some insight – listen before you speak. – father of David Boies, “Superlawyer”
  • Be open to listening to people. – mother of Herb Kelleher
  • It’s good to solicit your people’s opinions before you give them yours. – boss of Lloyd Blankfein, CEO Goldman Sachs
  • No one is interested in talking all night long about your business. Quit being a business bore and listen. – sister of Julian Robertson, Founder, Tiger Management
  • The best advice is often the most painful advice, and you have to trust the person who’s giving it to you. – Beth Comstock, SVP General Electric
  • Have a coach. They watch you and get you to be your best. A business coach is somebody who looks at something with another set of eyes, describes it to you in [his] words, and discusses how to approach the problem. – John Doerr, Venture Capitalist

2. Mastery

  • If you’re going to be significant at something, you’ve got to learn it from the ground up. – father of Ron Johnson, CEO JC Penney
  • Invest yourself in what you’re building in order for it to grow.  Talk about what was wrong, what was right, what was working, and what wasn’t. – father of Ellen Kullman, CEO DuPont
  • If you don’t perform, you’d better look for another job. – boss of Peter Drucker
  • Do your best today, think about tomorrow, and maybe dream a bit about the future. But doing your best in the present has to be the rule. – Colin Powell, Secretary of State
  • Don’t just accept or reject the null hypothesis, use the data to enhance your description of the world. – Prof. Harry Roberts, Univ. of Chicago
  • Your people will be very influenced by how you carry yourself under stress. – boss of Lloyd Blankfein, CEO Goldman Sachs

3. Respect

  • Show your co-workers and employer respect – at the very least, show up on time. – “Bigfoot”, friend of Anthony Bourdain, Chef
  • Practice the golden rule. – Vice Admiral Robert Kihune
  • People should be respected and trusted as people, not because of their position or title. Frequently, position or title do not reflect the true merits of a person. – mother of Herb Kelleher
  • Everything in business is about relationships (especially with customers), and you should never take them lightly. – David Jackson, Co-Founder Altos Computer

4. Passion

  • You should do what you’re good at, and do what you love. – Danny Meenan, Reporter
  • Don’t give up, and continue to follow your passion. – friend of Mika Brzezinski, co-host Morning Joe
  • Connect your passions to your career. – Scott Griffith, CEO Zipcar
  • Follow your own instincts, rather than the views of naysayers or others who see the world in a different way. – Ace Greenberg, Bear Stearns

5. Challenge yourself and your assumptions

  • Failing simply just leads you to the next great thing. – father of Sara Blakely, Founder Spanx
  • Successful people do not let lack of experience get in the way of taking on a new opportunity. – Sheryl Sandberg, COO Facebook
  • Break new barriers all the time. – Simen Agdestein, Chess Coach
  • When everybody knows that something is so, it means that nobody knows nothin’. – Prof. Alois Xavier Schmidt, City College of New York

6. Leveraging Strengths

  • Don’t let your ego or desire to succeed blind you to what you’re really good at. – Warren Bennis, Scholar
  • Take your employee’s strengths and find a place you could emphasize them, so it won’t seem as if your team is competing directly with one another. – Keith Reemtsma, Columbia University
  • Don’t try to change ordinary people into extraordinary ones – hire extraordinary people in the first place. – Phil Knight, Nike co-founder

7. Understanding Limitations

  • Develop your ability to leave your own ego at the door and to recognize the skills and traits you don’t possess and that you need to build a world-class organization. – Warren Bennis, Scholar
  • It is better to be alive [and a] little weak than [to] be dead in good health. (98% perfect and on time, rather than 100% too late). – Gérard Pélisson, CEO Accor Hotels
  • Fix the things you can change and don’t worry about the things you can’t. – Alain Chuard, Co-Founder Wildfire
  • None of us are smarter than the markets. – Jack Bogle, Vanguard Founder

8. Persistence

  • You can’t always control what happens to you in a game or in life, but you can control how you respond — you should never quit. – mother of John Hickenlooper, Gov. of Colorado
  • Don’t give up, and continue to follow your passion. When you fail or things turn for the worse, there will be a day when you realize this was the best thing that could happen to you. – friend of Mika Brzezinski, co-host Morning Joe

9. Position for Growth

  • Invest ahead of the growth curve. Think beyond the status quo in terms of the skill base, the experience, and the quality of the people around you. – Warren Bennis, Scholar
  • Invest your time in growth businesses, not non-growth. – Arthur Levitt, Chairman American Stock Exchange

10. And more…

  • First, get the cow out of the ditch. Second, find out how the cow got into the ditch. Third, make sure you do whatever it takes so the cow doesn’t go into the ditch again. – Albert C. Black Jr., CEO On-Target Supplies & Logistics
  • Money, pedigree, and valuable relationships create leverage, but so do ideas. So you need to write – put what’s in your mind on paper.  – Jules Stein and Lew Wasserman, MCA
  • Incorporate volunteerism in your company, for the benefit of your employees. – Alan Hassenfeld, CEO Hasbro



10 Techniques for a Successful Career


Last year, I had the great honor and privilege of leading a small team of newly hired engineers at Google. Towards the end of the year, as the team began to break up and shift onto other projects, I wanted to summarize my “best advice” for them as they headed off on their own, so I wrote a 10 step guide for career success at Google. As I read over the advice, however, it became apparent that most of it was generally applicable to all sorts of jobs, so I’ve decided to adapt it slightly and publish it here.

  1. Track your accomplishments daily, weekly, and quarterly. A simple daily log, weekly summary, and quarterly progress report are all you need. Keep them as short as possible without missing any important work you have done. Whenever possible, include direct references or hyperlinks to any supporting detailed documentation you produced. You will be amazed at how much you’ve accomplished when you look back. You will also be amazed how easy it will be to make the case for promotion or update your resume and prepare for a change in jobs. You may be tempted to use a tool to automate this tracking – don’t, that defeats the whole purpose. Keep it manual.

  2. Become the go-to person for something, and then obsolete yourself. Repeat. And when it’s time to move on, as the stock market saying goes: buy (into new projects or companies) low, and sell (yourself to the next one) high. In other words, move on when you’ve accomplished the bulk of what you can contribute on a project and have automated yourself out of a job, and a new project has a lot of low hanging fruit for you to pick. Build a niche, but don’t let yourself get pigeonholed, and don’t hold on to something because you are familiar with it. Remember: eventually, all work is thrown away. Learn to let go.

  3. Focus on the customer, and all else (including your career) will follow. To loosely paraphrase the Buddha, grasping (e.g., for promotion or other recognition) invariably leads to suffering and the opposite of the intended effect. Learn to let go of your ego and focus on the greater good. You will naturally excel and achieve without even thinking about it.

  4. Identify your strengths and leverage them extensively. The book Now, Discover Your Strengths can help you do this. Likewise, identify your weaknesses, and either a) shore them up, or b) learn workarounds. Get to know yourself well enough to know which of these two approaches you should take for any given weakness. Above all, be honest with yourself.

  5. Read, read, read, and never stop learning. Read whatever interests you, but choose your reading material wisely, with a focus on quality. Don’t read crap, and don’t read too narrowly. If someone you respect recommends a book or article, try to read it with an open mind. If you like something you’ve read, re-read it. To help get you started:

    1. Read and internalize the book: The 7 Habits of Highly Effective People.

    2. Read and internalize the book: How to Win Friends and Influence People.

  6. Listen. Listen to your customers, your manager, your executives, your teammates, and anyone else you work with. Try to understand where they are coming from, ask questions, and always assume the best intentions. Let them finish talking before you chime in. You will be amazed at what you learn, and how it will help shape and expand your view.

  7. Consciously choose your manager. If your manager is not great, let them know (also let them know if they are great!). If they don’t change for the better, let their manager know, and start looking for something new. Your career is too short to spend years under someone who can’t help you grow.

  8. Continually assess your situation. Ask yourself, “Is what I’m doing a) leveraging my strengths, b) something I enjoy, and c) something I am passionate about?” If the answer is no, start taking steps towards correcting the deficiencies. Be open to reinventing yourself in the process.

  9. Realistically measure your stress level, and learn how to manage it. You’re probably subject to a lot more stress than you think. Just living in the modern world is probably more stress than the human body was designed to handle. Add to that life in the modern workplace, and you’ll understand why there are so many people suffering directly and indirectly from the effects of stress. Try out many techniques and see what works for you (exercise, yoga, massage, meditation, etc.).

  10. Don’t forget your family and friends. It’s easy to let work become your life, but your health and happiness depend critically on your close personal relationships. Have a life outside of work. Actively manage your relationships, and constantly renew the ones you value most. If you have a reasonably active social life, you’ll be much happier and productive at work.

(Oh, this list goes up to 11….)

11. Take a course on mindfulness and emotional intelligence. For example, there is one offered by the Search Inside Yourself Leadership Institute. Attend all sessions and do your homework, mindfully and diligently. Don’t let it end there – internalize what the class teaches, and practice practice practice. The awareness, mindfulness and emotional intelligence you develop will be the keys to dramatically improving your productivity and happiness.

Happy New Year, and best of luck in your career of choice!




Earning the Leadership Badge


I recently had two minutes to prepare a one minute speech about my leadership style. That forced me to concentrate on the key elements of being a great leader. I talked about the importance of showing the way instead of pointing the way, as well as the importance of causing order-of-magnitude impacts versus incremental improvements. But it got me thinking: what is a truly great leader?

I’ve written in the past about a few of the attributes of great leaders (see: The 4 Principles of Great Leader-Chefs), but that’s a little different than exploring what it means to be a great leader. Why bother talking about the definition of leadership? Two reasons. First, we all spend most of our lives following others, and need to be able to discriminate between the truly great leaders and the mediocre ones. Second, I find that it’s common for people to talk about what a great leader does or how one acts, but far less common to talk about how to identify one. It’s all too easy to mistake someone who merely looks like a great leader for the “real McCoy.”

Defining Leadership

A simple image search for leaders vs managers will show you all kinds of attributes for leaders. One of the most common lists that’s floating around the web says things like, “A leader coaches employees, depends on goodwill, generates enthusiasm, says ‘We’, gives credit, asks, says ‘Let’s go’, shows the way, ” etc. These may be enabling attributes for being a great leader, but they are not sufficient. In other words, a manager who does all these things may still not be a leader, much less a great leader.

Here are a couple of definitions of a leader, one from me and one from Daniel Goleman:

  • A leader is someone who takes people from one “place” to another. -Chris LuVogt

  • A leader is someone who has a sphere of influence. -Daniel Goleman

There are two key elements in both of these definitions: influence and change. We can synthesize these elements to make the definition a little more concrete:

  • A leader is someone who discovers, develops, or imagines something new, and then plays a key role by influencing people to take actions which make changes that in turn make the new thing real.

While it is commonly a very effective technique for a leader to personally take direct action towards the goal (showing the way), it is by no means necessary. That is more about the how of leadership, not the what. There have been many leaders throughout history that made their imagined realities real by simply convincing others to take action. The key element is that the leader convinces. He or she imagines or discovers a new reality, and then convinces others to make it real.

Thus, unless you are instrumental in turning a new idea into reality, you cannot really call yourself a leader. Success as a leader depends critically on this ability to innovate. In a recent talk, Astro Teller defined true innovation as that which results in order of magnitude improvements (10X instead of 10%). Similarly, Clay Christensen distinguishes between disruptive innovation and sustaining innovation. In both cases, these are just two points along an innovation continuum, one which I suggest is the same continuum we should use to evaluate leadership.

A Matter of Effect Size

If a leader influences people to cause change, an unusually effective leader is arguably one who:

  • exerts an unusual amount of influence

  • in order to cause large-scale change.

In other words, the greater the influence and the greater the change, the more effective the leader. I smell a “quadrant diagram” in our near future, but first we need to talk about how to measure change and influence.

One could be tempted to measure change in terms of the number of people’s lives that have been positively and significantly affected. While this is important, it can’t be all there is, as it confuses leadership with positions of power. In other words, just managing a large organization that wields a lot of power doesn’t make one a leader.

Instead, to measure change, we need to measure the amount of change. What did the leader start with, what was the endpoint, and what was the delta? This is a concept that is familiar to nearly anyone in business, finance, or science. Yeah, you made a million dollars, but if you started with a billion, that’s not quite so impressive. This goes back to Teller’s innovation definition, which at its core is one of relative magnitude (10% versus 1000%). So measuring change is about looking at the relative differences.

Measuring influence is a bit harder. It’s fundamentally about change as well, but specifically about changing people’s minds. While it’s important in measuring a leader’s influence to look at how many people’s minds have been changed, it may not always be the case that the leader changed them directly. Instead, and more likely, they changed the minds of people in powerful positions, who in turn convinced others to make the change real. In other words, the truly effective leaders multiply their influence through its carefully selected application. This is one reason why upper levels of management are sometimes called the “leadership team.” They have the ability to “convince” (through direct edict, if necessary) their whole organization to take a certain path. However, this doesn’t, of course, make them leaders, since they may or may not use that ability to effect large change, and to the extent that they enforce their will instead of convincing others, they also fail to be leaders on the influence dimension.

You can visualize all of this in the following quadrant diagram:

In the lower left, where relative change is small and the use of influence is also small, you have managers. As these two dimensions grow, a person can also grow into an effective leader. But one has to beware of the people who may look like leaders superficially – the lucky ducks and the worthless charmers. The lucky ducks are the people who through luck or judicious leverage of circumstances, are able to make large changes, but not through the use of influence. These folks should not be dismissed out of turn, but also should not be confused with true leaders. Likewise, the worthless charmers may seem to wield a great deal of influence, but somehow never accomplish anything big.

Effective vs Great

Somewhere along the line here, I stopped talking about great leaders and instead focused on effective leaders. Someone can be an effective leader, without being great. For example, Steve Jobs, while possibly the most effective business leader of our time and someone who affected the lives of nearly everyone in the developed world through his exceptional gifts of vision and charisma, was nevertheless arguably not a truly great leader. He was notoriously hard to work for, demanding, and some even say demeaning. These hardly sound like characteristics one would associate with being great. And Jobs isn’t the only well-known and successful leader to fall short in this way.

What’s the missing third dimension, the thing that distinguishes an effective leader from a great one? In the words of John Hamm in Unusually Excellent, it is character: being authentic, trustworthy, and compelling. It is, as Jim Collins says in Good To Great, humility. Simply put, it is the quality of the leader’s core values and how well they live them. So, in the end, the how does matter. Influence and change can make an effective leader, but how a leader achieves these goals is what makes the difference between an effective leader and a great one.

The Leadership Merit Badge

The title of manager is something that is bestowed, whereas the title of leader is earned. Being called a leader is a way of being recognized for actual accomplishments. I like to think of leadership as a badge, one which is earned and which if not continually renewed, eventually expires. It can be bestowed by anyone on anyone else, and ideally should be the result of exhibiting high levels of influence and relative change, while living one’s values. Paradoxically, the higher up in an organizational hierarchy one goes, the harder it becomes to exhibit true leadership – the starting point for measuring change is bigger (so the delta becomes more difficult to enlarge), the ability to exercise true influence likewise becomes more difficult, as the person begins to rely on their position of power to change people’s minds, and staying true to one’s self gets harder and harder as the pressures of managing a business or organization get overwhelming.

Take a moment and think about the people you are following. In other words, who is it that influences you and inspires you to action? This may or may not be someone in your formal management chain. Take a moment to evaluate them – what is their vision, have they delivered large-scale change through their influence, and do they live by their values? In other words, would you give them the leadership badge? Would you give them the gold star “great leader” badge? Maybe they haven’t earned it yet, but do they at least have a good chance to earn it? If not, shouldn’t you be following someone else?

Now take a moment to think about yourself. Regardless of whether you want to be a leader of others (as only few can be), we all should be leading ourselves in our own lives. Are you actively trying to change yourself for the better? Are you challenging yourself to improve? Are you staying true to yourself as you do it? In my next post, I’ll write about a particular technique I use to help me stay on track and always improving…stay tuned!

I’d like to acknowledge the following article, which helped inspire the writing of this post: “Management is (Still) not Leadership” – Harvard Business Review.



A Simple Semi-Automatic Text Summarizer


This one goes out to all the data geeks in the crowd….

In other posts, I’ve mentioned a text summarizer I’ve used to help me glean the salient points from a large amount of text.  The problem this tool addresses is simple: let’s say you’ve got several articles, or a book, or some other large chunk of text, and you want to discern the larger themes and semantic trends, of the text.  Trying to solve this problem algorithmically in a robust way for arbitrary text with enough quality for a public-facing product is a very hard problem.  But using a simple, time-honored approach borrowed from classical Information Retrieval can be good enough for occasional, personal use.  I’ve been using a simple script to do this, and I recently posted it on the web – give it a whirl:

At this point, you may be asking, “What the heck is he talking about?”  Okay, how about some concrete examples. As I mentioned in a previous post, I wanted to quickly discern the most important themes from a series of 41 posts on CNN Money that highlighted the best advice some successful business leaders had ever received.  So I plugged them into my summarizer, and this is what popped out (these are only the top terms):

Let me outline the lay of the land here: these are the words and phrases that appeared in the text of the 41 articles, sorted by a measure of “importance”.  You’ll note that the words have been mangled a bit – this is a process called stemming, which maps different forms of the same word to a semantically similar root (and also does something a little strange – converts the letter “y” to an “i” when at the end of a word).  The point here is that “drinking coffees” is semantically similar to “drinks coffee”, etc.  You’ll also note that some non-meaningful words like “the” and “of” are missing.  The summarizer is just trying to bypass these unimportant words and get to terms that express the core meaning.  The second column of the table is how many times each term has occurred across all of the documents, and the third column is how many unique documents this term has occurred in.  The last column is a magic number that takes the first two columns as well as other things like how long the word is, how many syllables it has, etc., into account to try to guess the importance of that term.  If you are at all familiar with “word clouds”, you could basically render these terms in decreasing font size to get a word cloud.

Interpreting the output takes a little practice, but can help lead to a better understanding of the underlying text, especially for larger chunks of text.  In this case, for example, I scan down the list and ignore terms that appear in most of the articles (like “advice”), or which don’t have a lot meaning (like “because” or “really”).  If I do that, I identify a handful of possibly interesting terms, including: “people”, “company”, “interest”, “start”, “person”, “listen” and “think”.  If I go back and search through the original source documents for the context these words were used in, I quickly discover that one common theme is around establishing and building relationships with others through careful listening.  It’s interesting to note that when I summarized these articles manually, without the help of my tool, I identified “Listening and Respect” as the most important theme.

Here’s another example: when I pointed the tool at this blog, here’s what it said were the most important concepts that I’ve been writing about – I’d say it’s right on:

To be clear, the tool has limitations (not the least is its ability to parse HTML properly and ignore scripts and boilerplate/sidebar text on pages – I may work on that).  Also, I call the tool semi-automatic because it does require some interpretation.  Regardless, I’ve had a lot of fun trying different source texts (like, the Bible, or the Constitution , or the lyrics of various “concept albums”), and would love to hear from you what you discover playing around with it.

It’s also important to understand that the source text should be “of a piece”.  For example, I’ve tried using the tool to summarize the headlines on major news sites, and what comes out is a mish-mash of terms from across the (unrelated) news articles.  In order for it to reveal an underlying theme, there has to be an underlying theme.  Perhaps it may also be valuable in doing just that – revealing a lack of cohesiveness.

I post this under the “leadership” heading because leaders often need to be able to quickly summarize large amounts of  text – as a leader, I can imagine using this kind of tool in a wide variety of ways – from summarizing a stream of tweets or blog, to summarizing a person’s resume (as an example, see mine below).  The possibilities are tantalizing… Here’s that link again:


Synthesize, Prioritize, Evangelize – Thinking Big, Part 2


The Big IdeaGreat leaders think big. They take the seed of an idea and grow it into something larger than anyone else would have thought possible.  In my previous post “Summarize, Generalize, Hypothesize – Thinking Big Part 1,” I wrote about a few techniques for identifying great ideas, and turning small ideas into big ones.  In that article, I focused primarily on the nascent stages of idea development, of getting in the habit of mentally inducing something larger and more impactful.  That part of the process is naturally a personal, internal one – with the ultimate goal of becoming so ingrained that it happens automatically within a few seconds of hearing or thinking of an idea.  But great ideas are ones which also survive a vetting process where others who are likely to have valuable input, and who may also eventually be involved in implementing the idea, also contribute to the expansion and filtering of the details.

Ideas are a dime-a-dozen, which leads to the intriguing implication that most ideas are worthless, and a precious few represent the nuggets we all search for.  Because most ideas are free, they have a couple of interesting properties.  First, people will share them freely, and second, ideas are (or should be) easy to throw away.  These two properties naturally lead to the next two steps in ideation: Synthesize and Prioritize.  The third step, Evangelize, helps bridge the process of ideation that began with “Summarize, Generalize, Hypothesize” with the rubber-hits-the-road reality of execution, while simultaneously building the momentum and passion necessary for success.

Unlike the first three “internal” steps, these last three “external” steps are neither mutually exclusive nor discrete, nor even done “in serial.”  They can and should be practiced as a cycle that gets repeated a number of times, with each step running somewhat in parallel, each time increasing the size of the circle of people involved.  This is illustrated in this diagram:

Thinking Big Flow
Thinking Big Flow


This phase is all about getting others involved, a little at a time, to improve upon your core idea, flesh it out, or even help discover its true core.  You will quickly find out if the idea is no good, because either people will tell you so directly, or no one will want to follow up on it.  But if the idea  is great, you’ll get all kinds of feedback, volunteers, and other support you’ll need to build a foundation for execution.


Synthesis is simply the art and act of actively soliciting others’ ideas and rolling them together into a grand vision.  There are many ways to do this, from sharing it with a trusted partner, to formally brainstorming it with a group of colleagues, to building a full-fledged “business case” or doing a SWOT analysis or building a prototype, and pitching it to upper management or potential investors.  The point here is to start small, and increase the “size” (in terms of number and influence) of participants with each round of the cycle, so that the idea gets more solid with each review.  As an example, in this article by successful entrepreneur Steve Blank, he says “…my partner Ben’s office was the first place I would go when I thought I had new ‘insights.’ And we’d run them to the ground for days before we’d even let anyone else know.”

It is easy to get caught up in the excitement of potentialities when synthesizing, and forget that, most of the time, ideas don’t pan out.  That’s why prioritization should follow close on the heels of synthesis.


When he talks about innovation, Astro Teller (the head of Google X) always emphasizes the importance of brutal prioritization of ideas (See for example this summary: Some thoughts on innovation from Astro Teller).  Starting with the fundamental observation that the vast majority of ideas are bad (or at least not “big”), it follows that most ideas should be killed  as quickly as possible.  This should be done using the simplest reasons first – like “not physically possible” or “illegal or immoral.”  Some ideas that are not immediately killable should be explored in a brainstorming or conceptual “white paper” mode (as described above).  The few ideas that survive this should then be built into a prototype or “minimum viable product” (to use the language of Eric Ries’ “Lean Startup”), and then tested to see if they are actually good enough to iterate on and productionize.  The point here is that you should assume your ideas are bad until you can prove them otherwise.

To truly lead, though, your ideas must be big.  What makes an idea big?  Teller offers a simple checklist – consider these three things:

  • Is the problem it solves big?
  • Does it actually solve or significantly ameliorate the problem?
  • Do you have a reasonable starting point?  (e.g., sure it would be great to build a time machine, but there’s no reasonable place to start)

It pays to not get too attached to your ideas – chances are they won’t survive the Synthesize and Prioritize steps, at least not intact as they originally sprang forth from your head, and you have to be okay with that or you’ll never get to the point of executing.  And it also never hurts to be reminded during this process that less is more, and you should always try to boil the idea down to its core.*


When first synthesizing, you’ll naturally be sharing your idea with a small group of people.  But once the group has hardened the core of the idea and reduced it to its smallest coherent state, it’s time to expand that circle.  Always look to be adding new members to your “idea-backing group” that are from a diverse set, but especially go out of your way to include potential customers and potential backers.  Structure how you present the idea as a solicitation for help, not as an edict.  And involve the current supporters in your solicitation for new members.

As the number of people who know about the idea increases, some will naturally fall by the wayside, while others will hang on.  It’s important to monitor two things about this process.  First, the retention rate needs to be something significantly larger than zero.  In other words, if the overall size of the group of supporters doesn’t grow with time, that’s a possible sign that the idea doesn’t have what it takes to fly.  Second, the core supporters need to be identified and actively engaged, to keep the momentum building.

Some feel that evangelizing is an art form, but there is a science to it that you can, and should learn.  “Made to Stick” by Chip and Dan Heath provides an excellent framework around building up ways to make sure that others remember, understand, and even support and adopt your idea.

It may take one round, or dozens, of this cycle to get to the point where you have the will, the vision, the design, and the resources to begin execution, but rest assured that if the idea is truly big and great, it will survive the process and be ready for full-scale implementation.  Be careful, though – not everyone on the idea-backing team should also be on the implementation team.  Make sure that any backer you carry over has the requisite skills, knowledge, passion, and/or position of authority to be able to contribute.  Otherwise, as with the prioritization of ideas, you’ll need to ask them to step aside, even if only temporarily, until that point when they can contribute again.


*Greg McKeown had a great article recently in Harvard Business Review that makes this and other related points: The Disciplined Pursuit of Less


Summarize, Generalize, Hypothesize – Thinking Big, Part 1


The Big IdeaGreat leaders think big.  They can spot a great idea, develop it, and then make it happen.  Some people have a natural talent for seeing the larger potential of great ideas, of knowing which sparks are capable of being fanned into bonfires and which are destined to cool and die.  They innately take something and run with it, imagining all of the myriad possibilities and implications.  Their brain is wired to work that way.  However, this kind of “right-brained” thinking does not come easily to everyone.  There are a few techniques, though, that anyone can practice, and if converted into habits, are the first step towards thinking big and becoming a great leader.

Summarize, then Generalize

The first technique starts with the seed of an idea and then mechanically explores it in every direction.  Every time you come across an interesting idea when you read an article, have a stimulating conversation, consume high quality media, or use a cool piece technology, try this simple exercise:

  • First, summarize.  Create a “tweetable” headline that captures the core idea – the part that made you say “Hmmmmm…”  Make it short enough that someone gets the idea in 140 characters or less.  Really try to whittle it down to the fewest words possible without losing the essence.
  • Then, generalize.  Step through the words in the headline and insert, delete, or replace each salient word or phrase with related concepts, especially if they are broader than, reciprocal to, or parallel to the original.

As an example, take a look at this summary taken from the opening paragraph of a recent article in the Association for Computing Machinery’s monthly journal:

The annual ACM International Collegiate Programming Contest develops teamwork, skills, and algorithmic mastery.

If you believe this contest is a great idea, why not take it to the next level?  Instead of “annual”, why not bi-annual, or monthly, or weekly, or ongoing?  Why just collegiate – why not high school, why not elementary school, why have it limited to schools at all?  Instead of a single Programming Contest, why not make it into a suite of contests that test a variety of skills – an “Academic Olympics”?  Why limit it to just sponsorship by the ACM – maybe a consortium of professional groups, or some governmental agency?  Taken together, this great little idea could grow into:

The ongoing Dept. of Education International Open Academic Olympics develops teamwork, skills, and mastery of a wide range of skills, at all stages of life.

As with any brainstorming exercise, it’s important to not throw away ideas that seem too big, too hard, or are otherwise unsuitable too quickly.  Take note of them, come back to them later, and pick the one or two that really resonate.

Hypothesize – Ask “What if?”

The second technique* is naturally complementary to the first, and also relies on simple textual manipulation. If the parts of the headline that you changed are represented by BEFORE and AFTER, then list out all of the sentences of the form “What if instead of BEFORE, we had AFTER?”  In the example above, you might ask “What if instead of being annual contests, we had ongoing contests?” or “What if instead of programming contests, we had all kinds of academic contests?”

For each such question, mentally tick off all of the implications, both positive and negative, of living in a world where AFTER is true.  Don’t worry about how to make that world a reality yet.  Here you’re trying to suss out the benefits and drawbacks of the idea.  This is a prerequisite for determining whether you may even want to pursue the idea.  It doesn’t have to be a full-on analysis – you can always do that later on.

Making it a Habit

These techniques work best if you have internalized them and do them automatically, but they won’t come naturally to you at first.  To help you do that, let me propose a 30 day challenge.  For each of the four weeks in the challenge, pick one of the four modalities mentioned above (written material, conversations, media like TV/movies/radio/music/art, and technologies), and focus on that modality for the week.  Each day, write down the results of the three steps (summarize, generalize, hypothesize) for at least one idea.  This is a brainstorming exercise, so try not to self-edit.  At the end of four weeks you should have at least 28 ideas – spend the last couple of days polishing them and getting ready for the next steps, which I’ll talk about in a follow-up post: Synthesize, Prioritize, Evangelize.

* This second technique has its roots in a meetup I helped found.  It was originally suggested by a co-founder Jesse Bridgewater, with inspiration from the TED talk tryouts.  It’s a great way to have interesting conversations – ask each person that comes to your social gathering to bring one “What if…” – you’ll probably find you won’t even get to them all!