Do you lead like a chess player or a poker player?

Legends spanning history from Marcus Aurelius to Bill Gates to Scott Adams have acknowledged the role of luck in achieving success. Despite this humble and public affirmation of chance’s important role in business success, the social connotations of “games of chance” (better known as gambling) are resoundingly negative.

Ashok asks how much is luck: Dilbert by Scott Adams

Answer quickly, chess or poker: which game has more prestige? Which game has an extra-curricular club with its picture in the high school yearbook? Which game gets played late into the night on boozy weekends with college buddies?

While I’ve never had the patience to improve my skills at either chess or poker, I grappled with this apparent societal contradiction for decades until a recent interview with Annie Duke, author of Thinking in Bets and other brilliant books, brought it all into focus for me.

I’m now convinced that teaching my daughters how to play chess instead of poker would be a major Dad Fail.

The key idea that brought it into focus for me is what Annie Duke calls “resulting.” Learning occurs when we reflect on the outcome of a choice we made, to inform our future choices. As Ray Dalio puts it, “pain plus reflection equals progress.” Daniel Kahneman, and others, explored how biology and society influences our decision making. In the realm of games, chess is deterministic: both players have all the information, and winning or losing a game is causally linked to the quality of decisions you make. Poker, however, is probabilistic: each player’s information is limited, and the outcome of any hand depends to some extent on which card flips over in front of which player (and their seating arrangements), so winning or losing a game is always a combination of decision quality and luck.

“Resulting” means categorizing a decision as good or bad based on whether the situation yielded a positive or negative outcome. This behavior drastically undervalues the role of luck in outcomes, and risks cementing poor decision making habits into the fabric of an organization. Conversely, active separation of the decision from the outcome, and objectively attributing the outcome to either luck or skill, is essential to improving decision making quality.

Business is a game of chance. The outcome of any complex scenario, whether it is an enterprise sale or a marketing program or a fundraising round or an executive search, depends somewhat on which events unfold in which order. In an organization led by a chess player, positive outcomes arise from “good” decisions alone, and negative outcomes arise from “bad” decisions alone. The implications are significant and pervasive: who gets promoted (or fired), which tactics become “best practices” (or taboo), etc., could all be a function of luck. Confirmation bias (among others) becomes cemented in the leader’s inner circle. In an organization led by a poker player, the culture includes open discussion about confidence levels and risk reduction, constructive dissent (i.e., playing “Devil’s Advocate”), and active eradication of cognitive bias.

So consider what example you set for your team, how you coach them to to make better decisions, who you involve in pre- and post-mortems of significant decisions you make. Are you “resulting” or are you leading them like a champion poker player?


How these two things happen speak volumes about company culture

17You can gain deep insights about an organization’s culture by understanding:

  • how decisions are made
  • how recognition, aka “kudos,” is awarded

Consider asking those two questions about a company the next time you are interviewing for a new position, in addition to the other best job interview questions.

The answers to these questions reflect the leadership style and organizational dynamic established by the leader. As a recovering consultant, I could not resist the impulse to reduce this concept to a two-by-two matrix:

Learn about a company culture by understanding how decisions are made and how recognition is awarded
Learn about a company culture by understanding how decisions are made and how recognition is awarded


In the lower left corner, we have a culture of lobbying and arm twisting where for decisions and recognition the forum is private and the basis is mostly on influence. This culture is often found in teams with weak leadership, where the boss is routinely peppered with closed-door “advice,” either thinly or thickly disguised as an agenda of personal advancement. Team direction changes frequently and indescribably, relying on informal channels of communication to disseminate the new direction. Expect high attrition from staff who value transparency and meritocracy.

In the upper left corner, we have a culture dominated by the “squeaky wheel” where for decisions and recognition the forum is public and the basis is mostly on influence. Tantrums, meeting hijack, and open conflict are reinforced as means to an end by the steady advance of a vocal minority in the organization. While also a product of weak leadership, the only improvement over the lower-left lobbying culture is that the rules of the game are publicly known. Anyone unwilling to compromise personal integrity for career advancement will not last long in this culture.

In the lower right corner, we have a stable, humble culture of relative introverts where for decisions and recognition the forum is private and the basis is mostly on merit. This culture likely reflects the self-image and natural personality of its leader. I’ve chosen a cupcake as the image to reflect this culture because it is a satisfying individual treat. While it might be relatively boring, this culture will also likely be more successful than those on the left side of the matrix, as individuals who cannot compete on merit alone and those who crave public recognition will exit.

In the top right corner, we have the most transparent, extroverted, results-oriented type of culture in this matrix, where for decisions and recognition the forum is public and the basis is mostly on merit. The multi-tiered party cake represents the culture in which the success of an individual greats benefits for the group. Decision making and recognition are public and merit, meaning that the “rules of the game” are clearly demonstrated and objective. While this culture requires a strong leader who is not afraid to hire “A players”, it will likely have higher performance and lower turnover than the other squares in this matrix.

In this summary, I have done my best to withhold judgement and simply provide a framework for readers to identify a company culture so that they can best chose the one that fits their own needs. If you have other “cultural diagnostic” questions to share, please leave a comment!

Which of these six leadership hacks are you using?

One day I will get around to creating a Hype Cycle (à la Gartner) for management and leadership buzzwords. Somewhere in between blockchain and tiger team you will find leadership hacking.

I don't always use jargon, but when I do it is crisp and disruptiveLeadership Hacks are Cliché but Effective

No, I’m not talking about the guy that learned all the languages while blowing hard boiled eggs out of their shells (no hyperlinks: if you don’t get that reference already, I’m not going to torture you with finding out). Leadership hacks are those subtle yet amazing techniques that aren’t written down in Drucker, or HBR, or Military Doctrine. These are the six techniques that I’ve observed in the real world over my first couple decades of professional experience:

  1. The Compelling Event: to prompt action (or a decision) by a certain date. Also known as “pencils down.” Why it works? In a multi-tasking, oversubscribed world, this technique prevents the modern version of Parkinson’s Law from taking hold: that every task expands to fill the time allotted.
  2. The Three Legged Race: to get two team members to confront their differences and appreciate their complementary strengths. Long-term version also called “two in a box.” Why it works? Often we fall into the trap of confirmation bias when we can keep people, or issues, at arm’s length. By forcing close collaboration, this can be overcome.
  3. The Yes, And …: Remove the word no from your vocabulary. Just like in improv comedy, to succeed you need to encourage participation and contributions, and work on redirecting creative energy towards the goal. You might be pleasantly surprised by new thinking that arises. Why it works? Gives your team the chance to provide the solutions (and receive the praise) while you constantly reframe and reframe.
  4. The Pre-Project Press Release: Begin with the end in mind. At the start of a project (or software development cycle), write the press release that you want to cross the wire when the project ends. Why it works? Visualization is a time-honored technique in athletics, performing arts, and business. Resist the urge to run off quickly to take action without planning the critical steps by working backwards from the goal.
  5. The On-site Off-site: Take a team into a conference room full-time for a full day (or week) to reach the depth of focus required for a true breakthrough in thinking. Oh, and also actually finish a task that they start. Why it works? Our work days have been fractured into thinner and thinner slices of focus by technology and projects running concurrently.
  6. The Weekly Digest: Send your manager, your team, or your customers a digest of important and interesting highlights from your work week. Include graphics and short summaries linked to longer items or attachments for easy digestion. The best Weekly Digests are a mixture of what matters to the reader with the topics that the author wants them to keep front-of-mind, written in a style that is lighthearted and enjoyable to read. Why it works? We can’t rely on others to communicate the ideas that are most important to our own success. In the hundreds (thousands?) of emails that people receive weekly, it’s easy to miss something important. Sending a digest email at the same time each week makes it a predictable, and in the best cases eagerly anticipated, summary. Take the time to advocate on your own behalf. Or, in a more Orwellian sense, ensure that you are the one to document history on your own terms.

Which of these have you used successfully? What would you add to this list? Leave a comment and let us all know!

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What drives your actions: interruptions or initiative?

The more Capitalist Hero biographies we read, the more we start to believe that initiative, drive, spark–whatever you call that motive force inside a leader that turns ideas into reality–is the essential quality that we should bring to work every day. Except, of course, when you shouldn’t.

[Note: I was recently reminded that this knock-knock joke is not quite as funny when “cow” is replaced with “husband.”]

Ironically, the vast majority of leadership roles–across industries, up and down the ranks of various size organizations–require the opposite type of trigger for action. Interrupt-triggered leaders, meaning the ones who are masters of prioritization, delegation, and execution of tasks that originate externally, are far more effective in the situations where you show up to work with a 5 gallon pail only to have 10 gallons of, er, sunshine piled on your desk every day.

I came across the idea for this post buried deep in a refreshing book by Ben Horowitz called The Hard Thing About Hard Things. I believe it was in a chapter about memorable hiring mistakes. In fact, most of the book is about memorable mistakes from his career as a technology entrepreneur, interspersed with hardcore West Coast rap lyrics, which makes for a very refreshing alternative to most Silicon Valley Hero books I’ve encountered.

So with the concept of leadership actions triggered by interrupt vs initiative out in the open, here a couple questions for you to consider as you take the concept with you to work tomorrow:

  • Am I more naturally triggered to act by interrupts (reactive style) or initiative (proactive style)? Here’s a test to help you decide: imagine a meeting gets canceled at the last minute and you find yourself with a free hour. Do you grab that crumpled bar napkin/receipt/sticky note off your desk with the “big idea” you wrote down last week and start working on it, now that you finally have some time? Or, do you wait a couple minutes for some hot new emails to arrive, and if nothing comes, take a lap around the office asking if anyone needs a “roadblock removed?”
  • What style of leader will my team need most in the next 12 months? Remember, there is no judgement between interrupt- vs initiative-triggered leaders. They are just different styles, suited for different situations. I won’t, however, open up the can of worms about whether the interrupt- or initiative-triggered leader is the cause or the effect of the organizational situation. Let’s just acknowledge that when they fit, the right kind of work gets done at the right pace to move the group forward.

Who is the quintessential interrupt-triggered leader in your life? Who is the embodiment of initiative? When do you find that one style is more effective than another? Leave a comment and let the leadertainment community know!

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.

4 counterintuitive leadership traits

“The difference between a leader and a dreamer is who gets followed.” I can’t attribute that quote to anyone in particular, maybe it was a fortune cookie. It’s also possible to substitute “tyrant” for “dreamer” and create another set of leadership lessons.

Segway Guy
Not being followed.

Much of what has been written about leadership styles emphasizes being visionary, creative, decisive, and fearless. My sense is that too much of these traits undermine the trust of the team you lead and erode your credibility. I’m not trying to write the next revolution in leadership theory (heroic, post-heroic, servant, virtual, 21st century — all taken) or even to suggest that the points below are academically complete. But they line up with my experiences in life so far, and they work. What do you think?

  1. Don’t try to right, just be clear. How often do you make a point of having the last word? If you want to build a team who points out risks in your plans and builds solutions collaboratively, you need to give them airtime without insecurity. Thanks to Ping Fu (what a name!) for that lesson in Build Magazine.
  2. Show your vulnerability to build a reputation for strength. It can be very humbling during a tough period to know that your role model has experienced similar setbacks and grown from them. Rather than acting invincible, be open about your weaknesses, failures, and fears to show that you, too, are human. Surprisingly, your team might regard you as a stronger character because of those revelations.
  3. Don’t try to be dynamic if you can’t first be consistent. Do you set sweeping strategic goals or drill down to every minute detail? Do you codify tribal knowledge into efficient process flows or do you rearrange the furniture to spark creative innovation? Do you sway with the ups and downs of individual relationships or lock a laser beam on the goal? Yes, we should all develop multiple leadership styles to be more successful in a wider range of situations and with diverse teams. But trust is a prerequisite, and consistency builds trust. To clarify your current strengths, ask for some feedback or try a more scientific assessment such as Tom Rath’s.
  4. At some point, everyone just wants to be told what to do (even if that is just so they can argue with you). The questioning/Socratic method of coaching is great for learning and building ownership. Don’t forget the root of the word “executive:” you’ve got to pull the trigger at some point. Those on your team looking for directions to follow will do so readily; those looking to challenge your authority will enjoy getting another chance!


What’s the difference: training, coaching, teaching, mentoring?

Four Scenarios, Four Styles

If your development style resembles Gordon Ramsay’s, read this post and then get professional help

Subtle differences between the interactions of training, coaching, teaching, and mentoring can produce drastically different outcomes. Just as it is important to have a variety of leadership styles available to help you lead effectively in different situations, you must also be comfortable switching between development styles as appropriate. For additional reading on these topics, check out this list.

Training – to help a person master a specific skill in a direct (or “hands on”) interaction, use Training. To use a situation outside of work as an analogy, let’s imagine you want to help your daughter (or son, spouse, or roommate, depending on your situation) learn to make her own breakfast. The Training style involves getting the ingredients and recipe out, and working next to her at the stove to make an omelette together. After a few attempts, she will do more and more of the task herself until she is independently proficient.

Coaching – for a specific skill, but now in an indirect (or “hands off”) interaction, use Coaching. For the omelette example, this means talking to your daughter before (and/or after) breakfast for a conversation. Ask questions to reinforce knowledge and help her anticipate setbacks before they occur. Give tips and tricks that have helped you succeed at the same task. Great coaches also help to boost confidence and reduce anxiety to improve performance.

Teaching – increase capability in a general suite of skills through direct interactions with Teaching. You can help your daughter master a number of breakfast recipes from crepes to congee, over a series of lessons in the kitchen. A wise teacher in this case will also include effective dish washing in the curriculum! Teachers help build skills in a number of tasks, plus help to generalize the approach they teach to enable success in related (but not identical) situations.

Mentoring – the most abstract development method, mentoring builds capability in general skills through indirect interactions. Mentoring your daughter in this analogy would include conversations to explore why independence and proficiency in meal preparation is important, what she enjoys most and least about what she’s learning, etc. Great mentors fill in blind spots, clarify motivations, and remove mental obstacles to success over longer-term interactions.

Because it is hard for a consultant to explain anything without a 2 x 2 matrix, I have included the table below for reference.

How do these definitions match your experiences? Thanks for your comments!


You need three things to succeed. As a coach, I can only give you two

Sometimes a softer, coaching approach gets the group closest to the pin

Recently a member of my team was struggling to meet client expectations. His direct manager (who reports to me) kept me aware of the situation, and was putting in more of her own time than any of us wanted in order to help him keep his head above water. After the pattern continued for about two weeks, it was time to intervene. The three of us sat down and discussed the framework below:

  1. A clear vision of success – the first thing I can do as a coach is help you understand what success looks like. I can describe this in my terms, I can show you prior examples of success, and ultimately I want to hear you articulate how this vision applies to the current situation in your own words so I’m sure we’re on the same page.
  2. Skills to complete the work – in the spirit of “if this were easy, it’d be done already,” you are likely going to have to reach a new level of capability to succeed. Let’s identify which core skills you need to build (technical, interpersonal, communication, etc.) to achieve the vision above, and how you can quickly build proficiency and confidence.
  3. Motivation –  this last part must come from you. Ideally our discussions will tap into some of your longer term aspirations, and you will be motivated for a while. Maybe you will have to find motivation on a shorter time scale: avoiding a negative performance review next month, or just not seeing my smiling face first thing every morning to ask you what the plan is! Of course I will help you with a framework to identify your own personal motivators, but at the end of the day, motivation is entirely internal.

This collaborative, coaching style of leadership might come naturally to some of us, and might need cultivation in others. You can read an example from Michele Fabrizi, a leader who found success through a strong coaching style, at one of my favorite new sites,

For a more detail about leadership styles and how to select the most effective one for different business scenarios, check out this classic from HBR by Daniel Goleman. (image above from HBR)

What do you think of this framework? Try it out, and let me know the result!