Uncertainty: The real story of leading

Let us now praise those who search, who do not spin a story of imagined success, or a story of Phoenix-like recovery from failure. Let us praise not knowing for sure, because that is the sure thing – in business, in startups. In life. Let me now praise Path. This aptly named startup is getting interesting – that is, if you’re interested in leadership.

“…We’ve made a lot of mistakes,” said Dave Morin, CEO of Path, a San Francisco startup that saw a lot of attention in the business press and from celebrities with real cool cred in tech. (Ashton Kutcher and Brittany Spears. You be the judge.) And, according to the NYTimes update, Morin also played the flashy role of first and best believer in the inevitability of his vision. For a leader like him to confess to mistakes after playing the tech celebrity so well, let us praise that reflection and humility.

dark path

Most of us know two narratives about about leaders and startups. The first is the story of a leader with a brilliant idea. With some adjustments along the way and nod to the hard work behind the curtains, the story is one of seemingly inevitable success. The leader is responsible for it, with appropriate nods to the team that made it possible. It’s the revered American story of individual effort and independence.

The other story is “what I learned from failure.” We love this story because it is in fact mythic. Think Moses in the wilderness, Jesus in the desert, Dante’s hero in the dark wood. If hubris is the hero’s flaw, the desert teaches her humility, also known as self-awareness. I don’t know Dave Morin, but it sounds like he’s in the desert. I’m grateful that his story isn’t a simple version of success or failure. Morin is more like you and me, not knowing for sure. Until “it” happens, we don’t know for certain what “it” is

Uncertainty is almost unbearable for prolonged periods. There’s a good argument for experimenting with action, even any action. It’s the empirical way we cut a path through the dark wood. Those experiments may seem to how we pulled ourselves out of quicksand. But they’re still only techniques. And they don’t always work. Better than a lesson from inevitable success and instructive failure is the lesson that we have to face uncertainty alone and look within. What sort of person makes it out of the desert?

In my experience, leaders – maybe everyone – want something from work. Beyond a living, we are always seeking something else, too. Purpose, power, acknowledgement, respect, community, competition, meaning, and many other things.

The leader who makes it through the desert is the one who finds her purpose under the company, the product, the team. What makes us want to do this, our chosen work? What do we want to get out of it? That is the theme of story we are in.

Purpose-driven career requires courage and fortitude


Quote of the Week: Last week, when [The Drucker Exchange] asked about the importance of purpose in a career, reader Anthony Ghosn had this to say:

The challenge is that the individual power [of a purpose-driven leader] is a threat to the shallow management and executive control that we have all experienced in organizational behavior through executives driven by fear and short-sighted initiatives.The real breakthrough is when the organizational leader unleashes the power of purpose-driven aspirations.

The leader that can stand back, let go and watch the power of a collective purpose-driven organization will realize unmatched success. It is a balancing act, and this approach requires fortitude and courage, but many organizations have succeeded and have sustainable organizational models with ‘purpose’ as an underlying and guiding principle.

via What Peter Drucker Would Be Reading | The Drucker Exchange | Daily Blog by The Drucker Institute.

Entrepreneurs: Controllable thoughts are key to resiliency

Entrepreneurs:  The data say they are great at starting companies that fail.  That takes resilience.  For those who love the thrill , there are few other ways to work that are as satisfying.  If they are not already resilient, entrepreneurs do well do bulk up on it. Thanks to Eleanor Chin, who recently talked to WEST members, I have some recommendations for leaders who would be resilient.

What it is and what it does

Resilience is the ability to grow and thrive in the face of challenges and to come back from adversity.

Resilience makes it possible to step back from the situation with a growing degree of equanimity.  I use equanimity to mean acceptance of a realistic view of my responsibility in the success and failure.  It includes an equally realistic view of forces beyond my control.  Some of the things outside any one person’s control are people, circumstance, big-picture dynamics like the economy and markets, and large scale systems like public policy and infrastructure.

The chopstick fly-catch

If you remember your Karate Kid, the student no longer needed the teacher when he could snatch the fly out of the air. Sure, it’s a cliche.  But one path to greater resilience, Daniel-san, is grasping thoughts out of thin air.  It’s how you can take control of them and create a different outcome.

When we look back at situations, we wonder why we did that.  Often it was counter-productive.  Maybe we’re ashamed. Why yell when I could have asked a question?  Why fire someone when I knew that the problem was more complicated?  That reaction can be traced backward to the event.  Take a look at the illustration below.

What Albert Ellis has shown is that if you identify the thought triggered by the activating event (his term), it’s also possible to address that thought with others that can dramatically affect the emotion that it produces.  And since emotion often evokes the bodily fight-or-flight response, it’s a way of breaking the grip of bodily survival response that, be honest, don’t serve us at work.ABC from BIG IDEA

To come back from adversity, we need to have some distance from the thoughts that automatically trigger unbalanced judgments about ourselves.  It can be tough to do in the heat of the moment.  It takes practice.  But when it begins to change reactions, it is also making you more resilient: less likely to be knocked off your feet by those reactions and more likely to get back up when you are.

If you’re working with coach, she can help you apply this method to day-to-day “activating events.”  If you’re not already working with a coach, I’d be glad to introduce you to the practice.

In the meantime, here’s a worksheet to help you think it through:  ABC worksheet

Be your own change leader: Boston Discover Meetup, Mar. 27


The difficulty of leading change in an organization comes from the change that takes place within.  That’s why two colleagues and I get together every month for a Meetup that’s all about tuning the instrument for change: you.

Boston Discover Meetup
Click to join the Meetup!

Because we are all busy, stressed, and over-committed, it makes sense to say, “I’ll think about change when I can breathe again.” And who are we kidding?  Sometimes that’s the best any of us can do.  But we believe that you could be missing the most important information about the change you want to make.  There’s crucial data in the little picture.  It’s staring back at you from something that happened this week.

With a little attention, reflection and the sense we make of it can power your change initiative.  You know the one:  It’s the vision you have of a future you as a remarkable start up co-founder or big company senior leader, or expert and guru, or workplace humanizer, social transformer, good father, mother, spouse, friend, or citizen.

Know a little to have a big impact

Boston Discover Meetup is a conversation.  It uses discussion and a methods of reflecting on experience that we’ve learned over the years.  It started because we wanted to recognize that reflection is important and under-appreciated.  We have  become a little community committed to helping each other have a bigger impact on the world.

We set aside an hour or so to catch our breaths, collect and make sense of meaningful moments from the recent past, and see ourselves more clearly.  We believe this frees us to be the change agent we want to be.  It’s a “course” in the sense that we’re learning, but ourselves and our experience are the text.  We’re not teachers, though.  We’re learners, too.
Greater Boston Discover

Is this Meetup for you?  The best way to find out is to give it a try.  But you might find it helpful if any of these statements resonate with you:

  • When it comes to generating creative solutions, I may be using the same old ideas.
  • I can see that I need to broaden my network and work with people unlike me (in my company, my industry), but I don’t know where to begin.
  • There’s nothing really wrong with my job or my life, but I’d like to feel the kind of zest I used to.  I wonder where it went?
  • I am feeling sort of stuck.  I have a goal that I’m blocked from achieving.  I want to get off the dime, but I don’t move.
  • I’m doing everything I can to bounce back from a setback.

Here’s a one-pager (pdf) that you can share with friends.  Boston Discover Meetup – Thursday March 27, 6:00 p.m. 

And here’s an introduction to the  Boston Discover Meetup founders (pdf).



You are a center of competitive advantage, from author Dorie Clark


“Make yourself a hub,” said Dorie Clark, author of Reinventing You, Reimagining your Future at the TEC forum at Foley and Hoag on February 26.  Clark offered four other great strategies for making sure people see, know, and can say a few good words about your distinctive value.  I’m not going to give them away because she does that at her website and in her book (links below).Be the hub, bub!

“Organizations naturally develop ruts and siloes,” Clark said. It’s a natural result of getting work done.  As teams and functions focus on work, they screen out input that competes with their need to satisfy customers (external and internal) right now. And that opens the door for leaders and contributors who want to create personal competitive advantage.

Hubs are people who remain curious about what’s going on across the siloes and actively develop an authentic network of colleagues, friends, and business buddies.  They can be within and should be beyond the organization.  This network helps them:

  • Interpret different perspectives, including pressures affecting others, metrics and personalities that drive behavior, professional identities that inform at-work values
  • Communicate how things get done
  • Notice and highlight trends and changes
  • Connect influencers across siloes
  • Find the other hub people

For leaders in larger organizations, being a hub is practically a necessity.  If you want to be a strategic thinker, and you do, you need to think about more than one time frame at a time.  Being able to ask good questions about the implications on folks you know in operations and marketing will trigger a real and perceived multiplier effect.  You don’t need to have all the answers, but you need to think across the organization both as it is and as it may be.  Being the hub will help take you there.

For entrepreneurs, being a hub extends your senses.  A challenging part of your role is listening to the rails for the sound of the oncoming train.  You want to anticipate the rumble and the roar before others.  To do that, you need a wide circle of people who are paying attention to other signals.   While you’re listening and reporting for them, they’re helping you notice changes that may have an impact on you, your company, and your prospects.  Your network stretches across ruts to sense the emerging future and recognize its current incarnations.

Get more estimable Dorie Clark goodness at www.dorieclark.com.  And her book Reinventing You: Define Your Brand, Imagine Your Future is a valuable and brisk read for the transitions when you need to change people’s perception of what you do, how you do it, and how well you are able to do it.

Entrepreneurs: Traits to develop, but you are not alone

Do you have the right five or seven or ten things you need to be an entrepreneur?  I don’t think so, and that’s great news.

The thrill of running the  show is attractive.  It plays to your strengths. But the litmus test is whether you’re willing to find people to augment you – your skills, experience, ability. If you have the whole package, failure is still likely.  Without others, it’s almost certain and they’re the key improving your odds.  That’s the hidden message in this HBR blog post on The Skills Most Entrepreneurs Lack.  Serial entrepreneurs in the underlying study were ranked higher than a control group in four traits:

  • Persuasion
  • Leadership
  • Personal accountability
  • Goal orientation

Together they can make for a leader with vision who is committed to winning others to that vision; one who makes great demands of herself, who delivers, and who will keep on striving.  These strengths help drive under-resourced, under-funded start ups through significant obstacles.

Leading edge of learning

But as some start-up veterans will tell you, these leaders can drive others crazy. That’s because they don’t demonstrate the traits that help make strong organizations, the kind people that want to belong to. But that’s where entrepreneurs have the biggest chance to open themselves to the leading edge of learning.

If you’re employee number four or seven or more, and not a co-founder, you need something different:

  • Empathy:  You need some appreciation for the challenges of your work, your contribution, abilities you need to develop, and occasionally, for the sacrifices you’re making.  We’re all adults here, but the work is hard.  Entrepreneurs need to develop empathy.

Key traits, from HBR.org

  • Planning and organization to guide you from today to the accomplishment of the company’s vision.  Entrepreneurs can answer to their intuition when they’re solo.  Unless they can recruit psychics, a plan and process helps keep the team on the road together, even if plans change as part of pivoting.
  • Analytical problem solving:  You need to understand how decisions are made. Entrepreneurs’ intuition made be as sound as in Blink, but “that don’t scale.”  It’s encouraging to see the empirical approach that dominates many start-ups these days.   There are times when a leap of faith, a big bet is the right play.  It’s after you’re out of data.
  • Self-management:  People need a degree of consistency in leadership. The average start-up employee has a higher-than-average tolerance for ambiguity. But entrepreneurs throw a long shadow. You want the leader and the company to succeed. But your Spidey sense is always alert: Is this boat stable? Is the captain still in charge? Self-management in your leaders gives you a sense of consistency and that makes trust possible. It also makes leaders more effective on all fronts.

Leaders: You probably already think of your market space as an ecosystem.  Think of your company the same way.  Make the most of the people around you to find the uncomfortable edge of your leadership development and seek support in learning.

  • Who’s got it? Note, honor, and foster traits and abilities in others that you don’t have to the same degree.  Strong leaders aren’t afraid to recognize others for strengths that they themselves don’t have in spades.
  • Don’t delegate it: It’s a relief that you don’t have to do it all yourself.  It shows humility to be open to others.  But it is your responsibility to know yourself and make the most of your raw material as a manager, leader, and entrepreneur.
  • Learn from those who have strengths you don’t.  You may never be a paragon of empathy or planning and organization, but you can learn.
  • Investigate the inside job: What’s keeping you from getting better at say, listening, a skill that enables empathy?

Often the best way to identify your leading edge of learning is to ask for feedback.