Cracking the Nut (Part 2) – Tackling a Messy Problem

In the last post, we used the model to analyze a constrained problem.  Now, we’ll take on something a lot more open ended.

We work for Slimy Inc, an upstart company in the hotly competitive market for slime.  There is a dominant player in the market – BigSludge – and we are trying to figure out how to compete with them.  The traditional slime market is focused on commercial uses, and we’ve been having a tough time competing with BigSludge because they are the market leader and far larger than we are.  But, we’ve created some innovative new slime for kids to play with – a radical development in the slime market.  We’re definitely going to be first to market, though we have heard that BigSludge has a team investigating toy slime.

There is a raging debate within Slimy, Inc about how to compete with BigSludge.   Some people want to continue going after them head-on in the large commercial market, relying on our superior products.  Others want to put all the company’s efforts into the new kid slime product line (but is there really a big enough market, and will it develop soon enough?).  Another faction is pushing for an acquisition – BigSludge knows about the cool new products we’ve come up with, and they’ve had a couple of discussions with our leadership team about it.  As usual, there are dozens of variations of these basic ideas, and they’ve gotten tangled up with each other.  Emotions are running high and discussions have been going around in a circle.

We’ve been asked to take on this problem, analyze it, and get the decision landed.  The stakes are high – the decision will probably determine the future of the company and perhaps its very survival.  So, it’s time to get methodical.

Defining the Problem

We start here, as always.  The problem may seem obvious, but often the various stakeholders in the conversation have quite different notions.  So we’ll start with a statement of the problem, and it’s incredibly important that we write it down.  There is a great quote by Leslie Lamport, a well known computer scientist: “we write things down in order to realize how poorly we understand them.”  In our case, we land on this: “what strategy should Slimy use to compete with BigSludge?

Looking at the other tools in the quadrant, there are a couple that will be helpful.

Scope – what is in and out of scope for our problem solving effort?  In this case, let’s put the decision to pursue acquisition out of scope – that’s an interesting analysis, but it’s pretty separate from figuring out how to compete.  Our project may provide good insight, though: if we can’t come up with any compelling way to compete, then we may have a lot more enthusiasm about acquisition.  But we’ll confine our scope to competing with BigSludge.  We also have to make sure we get the key people to agree on our proposed scope!

Assumptions, Axioms, and Principles – I think of these as the foundation of the analysis, and they are incredibly useful to work through and write down.  They are related notions, but I try thinking about all of them to see which are most relevant to the problem at hand.

  • Assumptions – something you believe to be true, but you are aware that you might be wrong.  “There is a large potential market for toy slime that BigSludge will not be able to address for at least three years”.  Once you’ve identified your assumptions, you can decide how risky they are, how much your potential wrongness could hurt you, and hence how much you need to validate them.
  • Axiom – “a self-evident truth that requires no proof” – you simply accept an axiom without debate or validation.  In our case, an axiom might be “commercial slime is an essential need for current customers and nothing will replace it in the market during the next ten years.”  Your axioms can save you a lot of time, since you don’t need to bother analyzing them.  But, they are obviously dangerous, because if you are wrong about them, you can choose a really bad path.  DEC had an axiom that PCs weren’t a threat because they were too small to do “real computing” – and DEC paid dearly for that axiom by going out of business and being acquired in a fire sale by one of those scorned PC makers.  So one of my main reasons to poke on axioms is that groups generally have a set of them that are accepted unconsciously and unquestioningly.  It is worth teasing them out and stating them explicitly to make sure that they really should be axioms, and are not just questionable assumptions masquerading as revealed truth.
  • Principles – a core belief that you are going to follow.  Ex: “we will produce no toxic by-products in our manufacturing processes” or “we will tell every customer the turnaround for any order within 2 days of accuracy.”  Principles help you be clear about what you believe in, and they guide you in terms of what solutions you are willing and able to consider.

Goals and Defining Success – often when people are disagreeing about a course of action, it is because they don’t agree on what “success” means.  Are we trying to achieve a good ROI on our product development investments? Establish ourselves as the share leader in a new market?  Win share from BigSludge in the current market?  Grow revenue or profit by a certain amount?  Survive as a company?

I have found it best for the goal of a project like this to be succinct and measurable.  I also prefer if the goal

  • Doesn’t pre-suppose a particular strategy.  In our case, if we define the goal to be “create a large new market for slime”, then it heavily influences the approaches we can use to get there.
  • Is defined positively, not negatively.  I much prefer “radically increase our revenue and profitability” vs. “take share from our competitor”.  The negative approach can lock you into a zero-sum mentality, rather than creatively looking for any way to achieve your true goal.  Presumably what you really want is to make massive amounts of revenue and profit, regardless of what your competition does.

For our purposes, we will use this: “a successful strategy will yield a set of quickly growing product lines in the market that have higher profitability than anything we currently sell.”

Constraints – we are always under many constraints and we need to understand how they limit our options.  They might involve resources (money or people), legal requirements, etc.

Solution criteria – just like we did in the last post, we will need to come up with a ranked set of criteria for evaluating our options.  This is often the hardest part of defining the problem; fierce disagreements are often disguised arguments about the criteria.  For example, we have one group that wants to tackle BigSludge head on in their core market, which is large and well established.  Another wants to dedicate the company’s resources to expanding into the new kid slime market.  What’s going on?

The real challenge is that there are competing (and valid) criteria to judge potential strategies.  In this case, they are:

  • Size of the target market – one group questions whether the kid market is real and large.  There is no question that the current market is large.
  • Growth of the target market – the current market is mature and is growing with GDP.  We don’t know of anything on the horizon that will change its trajectory (per our axiom above).  The future of the kid market is much harder to predict; if the company can really nail an offering, it could be a huge and high growth market.  Or, it could stay tiny because only the early kid adopters will ever bother playing with slime.
  • Riskiness of our market prediction – obviously one is not risky in terms of its existing, the other is high risk.  Also, BigSludge has that research group that might get a clue and develop a competing offering in the kid market – it’s unclear how long we can have it to ourselves.
  • Ability to capture target market – to get the traditional market, you have to find a way to compete with BigSludge and take share or expand the market somehow.  The company probably has a pretty good sense of how hard this will be and has some ability to execute on it, but it may be very difficult to succeed.  To create a whole new market, even if the demand is there, calls for specialized skills and new partner relationships and the like.  Does Slimy have what it takes to pull this off?

The disagreement between the two groups is a disagreement about the value to assign to each criteria and the relative priority of the criteria.  This is really key to understand.  Until you start digging at the real basis of the disagreement, you will often go around in circles and everybody will just get locked more deeply into their point of view.

The faction that wants to go after the traditional market believes that (a) the opportunity in the kid market is small and will stay small, (b) betting on that market is much too risky and will take a lot of energy to pursue, and (c) Slimy doesn’t have what it takes to create new markets.  The other group believes that (a) the kid market has huge potential, that (b) it will grow quickly, (c) Slimy is in a good position to take a risk for huge upside, and (d) the company can learn how to sell to a new audience.  They also (e) doubt whether Slimy can compete effectively with BigSludge in their core market.  So the two groups differ on:

  • The value to assign to a criteria: is the kid market going to be large and high growth or small?   Can Slimy really make headway in the traditional market?  These questions can’t be answered perfectly, of course, since you are predicting a future outcome.  But you can certainly get data to support the analysis.
  • The relative priority of the criteria.  One group is risk-averse, the other isn’t.  This is a useful debate – how much risk is the company willing to take on?  What kinds of risk?

The key thing you can do with an analysis like this is move the debate from an unproductive place – “We should go after the kid market!” “That’s crazy, we should go after the money, and that’s in the commercial market!” – to a much more useful discussion around the real issues – can we get facts to assign values to the criteria more confidently, and how should we prioritize competing values?  These are still very hard questions, and they still require us to make decisions in the face of uncertainty.  But they let us focus our energies on reducing the key points of uncertainty and on having debates that we can actually settle.

We’ve now got the foundation in place for our problem solving effort – we know the problem to solve and its scope, we know what our goal is, we have articulated our principles and assumptions, and we know how we’re going to evaluate possible courses of action.  Next, we’ll move on to other quadrants of the model.

Cracking the Nut (Part 1) – How to Make Almost Any Decision

One of my favorite challenges is to take on a really hard complicated problem .. and figure out how to move forward based on a compelling and rigorous analysis.  Best of all is to do it with a small group of kindred spirits.  In a team that I was part of for many years, we called this process “cracking the nut”, and over the years I’ve developed a model for tackling a new problem.  I thought I’d share it in a series of posts, applying it to a couple of examples.

Getting Started

For the first example, let’s pick something straightforward and personal, but potentially hard: choosing among a set of job offers.  This diagram outlines the model (you can download a full sized version here):

Define the problem

Let’s dive in.  The first thing to do is make sure that you really define the problem.  For our job conundrum, that’s pretty easy: “figure out which of my job offers is the best”.  Of the tools in this quadrant, there is one that is really going to be helpful for us: decision criteria.  In other words, what actually matters about the new job.  There are many factors that might matter.  One team works in a really cool office, another is located in a great neighborhood, another is working on an exciting project, another has a dynamic leader, etc.  Those are all potentially legitimate reasons to pick one over the other .. the question is, what matters to you?

It can be quite hard to figure this out – you have to become a bit of a detective, because often your emotions will lead you to over- or under-weight different criteria vs. how they will truly affect your life.  One way I get started is to list all the characteristics that spring to mind about each of the jobs.  Then winnow down to the ones that I think are the most important.

Let’s say you have done this and came up with four rank ordered criteria.  You will probably be inclined to have more, but try to keep the list short – priorities get watered down if you have a lot of them.

  1. Impact of the project
  2. How skillful I am at the work
  3. Salary
  4. Work/life balance

Challenge yourself a bit here.  Think back on when you were happiest and most engaged in your work, and ask if that is really reflected by the criteria you picked and the order you put them in.  “Let’s see .. I loved my job on the WickedCool project.  Why?  Well, the woman running the project was amazing and inspiring.  I got to dive in to a bunch of new areas I’d never done before.   I worked like a dog, but it was so fulfilling to see the project ship and touch so many people’s lives.”  And think about counter-examples.  “I was miserable working on the Grumble project.  Nobody was inspired by what we were doing, it was the fifth version of a minor product.  I got home for dinner every night, but I just dragged myself through the day.”

Now, do the things that popped out as great or bad match your original criteria?  No, not really.  An inspiring leader and team didn’t make your list, but that was critical in both WickedCool and Grumble.  Work/life balance was lousy when you were happy, and good when you were miserable.  Salary didn’t come up.  And if you were learning all the time on WickedCool, you were probably lame at your job for a fair amount of time in the beginning.  But the impact point did make the list.

So perhaps this is a more accurate set of criteria:

  1. Inspiring leader/inspired team
  2. Impact of the project
  3. Chance to learn new skills

Keep going, keep challenging yourself.  Pose hypotheticals – if I got offered a job working for somebody great who is doing something I don’t care as much about, would I take that rather than working for a less exciting person on a project that inspires more passion?  Another good tool is to demote a criterion to a constraint.  You might need a certain salary in order to support your family, but as long as you make that much you won’t prioritize one job over another because the first one pays better.

Again, the whole point in a personal decision like this is to figure out what really matters to you.  Not what is supposed to matter.  Not what matters to your inner critic or your mother or would impress that teacher who liked somebody else better.  To you.


This quadrant focuses on what you need to understand better in order to make the decision.  You want to focus on things that will actually affect the decision, are not known, and are knowable within a time frame that is relevant.  In the case of the job hunt, you’d look at the criteria that we identified above, and see whether you actually do know how the different job options stack up, and if you can know.

Take “inspiring leader/inspired team”, for example.  If you went through a whole set of interviews with people on the team, then you should have a decent read on that one.  But if it’s one of the most important things to you, then it may be worth digging some more.  Maybe you can take somebody on the team out to lunch and explore it more informally.  If they are offering you a job, they want to sell you – it’s a big investment of their time to find somebody and make an offer, so they will presumably be motivated to encourage you to join.  If not, that’s a potential red flag – you learned something even by being turned down.  Talk to somebody who works with them and whose judgment you trust, if possible.  Talk to somebody who left the team.  Do the best you can to figure out how a team or company or neighborhood or whatever really stacks up on your key criteria.


This quadrant covers the project management aspects of the decision.  In the case of picking a job, it might not be too complicated.  But, there may be other stakeholders (do you have a spouse/family/etc who would be affected if you picked one job over another?).  You probably have a deadline – the date by which you need to make a decision.  There might be a workback, in the sense that you have to notify your current employer/team, or you have to negotiate salary, or you need to sell your house or give up your lease or whatever.  Make sure you have all of these aspects captured.

Evaluating Solutions

Now that you have done your research, go back to your set of options, and test them against your criteria.  You’ve spent a bunch of time figuring out what truly matters to you, so focus on that – don’t let surface things that influence you emotionally take precedence.  You definitely shouldn’t ignore your emotional reaction – a gut feel that something is wrong is always worth listening to.  But, a gut feel that you will be a much cooler person if you work for a company in a particular area code should be given the importance that it deserves .. whatever that happens to be for you.  Now you can really stack up your options with a clear idea of how to evaluate them, and figure out which one is the best choice for you.

So that’s an example of using the framework to make a constrained decision.  Next, we’ll give it a spin on something much more open-ended.

Five favorite books .. of insight from unexpected places

I’ve found many intriguing ideas about teams and projects from books on seemingly unrelated subjects.  I’m convinced there are universal principles that can be used in any environment for virtually any goal that you set your mind and heart to achieve.

Dance Choreography

Twyla Tharp is a very well known choreographer who founded her own dance company in 1969 and has performed many works that heavily influenced her field.  She is still active, and in 2003 she wrote a terrific book called The Creative Habit.  In addition to many interesting stories and anecdotes from her long life in dance, it is filled with practical advice on how to organize and carry out complex creative projects (complete with many exercises for you to try).

“The first steps of a creative act are like groping in the dark: random and chaotic, feverish and fearful .. For me, these moments are not pretty.  I look like a desperate woman, tortured by .. a message thumping away in my head.”  She tells us how to go from that stage to performance of a completed dance .. and to keep doing it, as she has, through a long and productive life.


I’ve always been fascinated by the way that movies are made.  I see remarkable similarities between the creation of a movie and a V1 software project.  You have an originating vision that must evolve as you go, you bring together experts in many different disciplines who often have trouble getting along, the team must solve very challenging design problems, and there is a long period of refining the raw material into a polished and compelling final product.  There is often a tense relationship between the creators and the funders, and the final outcome is the product of many people’s contributions rather than being completely under the control of any single person.

William Goldman is one of the most successful screenwriters in the industry.  He wrote many famous movies, including Butch Cassidy and the Sundance Kid and All The President’s Men.  He’s also written some of the best books about the movie business, including Adventures in the Screen Trade and Which Lie Did I Tell?  Check out either one to learn about making movies (with great anecdotes about famous movies and the often deeply odd people who make them).  One of his well known mantras is: “Nobody knows anything”.  By which he means, nobody has a clue how a movie will do until it is released – the expectations of the most experienced movie makers are routinely confounded.  The same can be said about radical new software products!


I really like to read poetry, which can often be a rich source of introspection and insight.  Catching Life by the Throat, by Josephine Hart, lets you read some wonderful poems and learn about the poets who wrote them.  What I love about the book is that it captures the energy and excitement of a great poem and conveys some of the all-consuming passion to create.  “I was a word child, in a country of word children, where life was language before it was anything else.”  “Poetry, this trinity of sound, sense and sensibility, gave voice to experience in a way no other literary art form could .. it threw sudden shafts of light on my own soul and drew at least the shadow outline of the souls of others.”  The act of creating anything new springs from passion and is refined through unceasing and painstaking effort.  This is a passionate book about the magic of poetry.


You may have heard about Josh Waitzkin because of his father, who wrote a fun book called “Searching for Bobby Fisher” about the development of his son into a chess prodigy.  The book, which was also made into a movie, is a fascinating glimpse into the peculiar world of obsessive chess players.  Mostly ignored by mainstream society, the subculture occasionally bursts into view, as it did during the cold war or when its stars were pitted against supercomputers in man vs. machine contests.  Josh had a long period of prominence in the chess world, starting when he won the National Chess Championship at 9 years old.  He then went on to become a Tai Chi world champion as well!

From these experiences, Josh wrote his own book called The Art of Learning.  He shows how he takes on a new discipline and applies the same approach to it that he learned as an obsessive childhood chess player.  He copes with losing, deals with adversity, and is very systematic about achieving an extreme level of skill and ability.  He’s also able to learn from just about anyone – as a child, he got some of his best insight into chess from playing street hustlers and gamblers.  The book is an unusual blend of autobiography and instruction, with a wealth of anecdotes about the extremely different and equally obsessive worlds that Josh has inhabited throughout his life.


I decided to learn how to draw as an adult, and I love doing it.  Many excellent books helped me along, but one stands out particularly when it comes to letting creativity flow (in any field).  Julia Cameron wrote The Artist’s Way to help unblock artists and get their creative juices flowing.  It became unexpectedly successful and the series that it spawned has sold millions of copies.  It does have some new age religious ideology that doesn’t resonate with me, but it is chock full of productive exercises to help you work through blocks and loosen up.  She lays out a 12 week process for breaking through obstacles, finding what really inspires you, and making it happen.  I think that any great achievement starts from a deep passion.  Once you know what you are inspired to do and you begin pursuing it with conviction, you are on the path to a life of meaning.  This book can help you find it.

Have you found insight in unexpected places?

Everything You Need to Know About Startups, You Can Learn From Mythbusters

I’m in the midst of another startup, with three friends, and we’re having a great time.  I realized last night how perfectly you can prepare for one of these adventures by studying one of my favorite TV shows, Mythbusters.  If you don’t know it, then you should probably stop reading and go watch an episode.

I reject your reality and substitute my own” – Adam

The core of every startup I’ve done is an overmastering conviction that you are doing something deeply important and new – that you have stumbled on an insight that nobody else understands as deeply and powerfully as you do.  You gather around you a small band of people with a similar conviction to pursue your crazy dream together.  Your day is not full of reviews and alignment meetings and sync-ups and constrained by “the way we do things here”.  You do them any damn way you please, and nobody around you is a naysayer.  Naysayers are not welcome and do not flourish in startups.  Only obsessive true believers, please.

They don’t just tell the myths, they put them to the test” – Narrator

The danger, of course, is that you might all be wrong.   Startups are highly prone to groupthink.  The brilliant vision you are chasing with all your heart and soul might not be something anyone wants.  To quote another sage, John Maynard Keynes has a great line about this: “It is astonishing what foolish things one can temporarily believe if one thinks too long alone.”

So, you have to mix in a ruthless focus on testing your ideas with customers.  This is the heart of the Lean Startup methodology, which I love and which we are using at Highspot.  You build something as quickly as possible that lets you evaluate your beliefs, and then you adapt based on what you find.  Just like the Mythbusters crew is constantly trying ideas, having their approach fail, and trying again and again, a startup is a succession of attempts to find a model that yields a product people want to use and a way to make money from it.

As Kari says, “I guess we don’t have a Plan B because we kinda expected Plan A to go off without a hitch.”  Adam’s response will resonate with most (successful) entrepreneurs:  “You should never, ever, ever expect Plan A to go off without a hitch. Usually, Jamie and I, it’s Plan D.”  Or in a startup, Plan Z.

And with any luck, you will end up with a conviction that is “Confirmed” and not “Busted”.

Failure is always an option” – Adam

One of the realities of startup life is that they mostly fail.  Going in, you have to have a crazy passionate belief that you can succeed, but you also know that the odds are not in your favor and you can’t allow yourself to be crushed if it doesn’t work out.  As Kari says, “If we’re wrong about this, we’re going to have a really bad day.”  But you have to embrace that possibility and forge ahead anyway.  I’ve met many people in comfortable big company jobs that talk about doing a startup .. but can’t bring themselves to leave their “gilded cage”.

“We have no idea what we’re doing.” – Grant

Another thing I love about startups and Mythbusters is the perpetual willingness to dive in and just figure something out you have no idea how to do.  You don’t apprentice with the person who has 20 years experience, you don’t go to school and get a degree .. you just dive in and make out the best you can.  And you mess up a lot.  Hence the Facebook mantra that they have tried to maintain to this day – “move fast and break things”.  Most large companies have long since lost that spirit by the time they get big and successful.  In a startup, if it needs to be done, you just do it.  By hook or by crook, the best you can, as quickly as possible, and with energy and passion.

If I had any dignity, that would have been humiliating” – Adam

If you are concerned about remaining in control and maintaining your dignity, go somewhere else where your needs will be respected.  Like honey badgers , “startups don’t care”.  You do what needs to be done.  But there’s a really great thing about it, too: “It’s funny what gets us excited, isn’t it?” – Jamie.  You will end up getting passionate about really oddball things that you don’t think twice about when other people are doing them for you – setting up your email hosting, picking desks for the office, stocking the frig with supplies.  It’s like parents getting excited and emotional about the minutiae of raising and taking care of the kids.

You SO wish you were me right now.” – Adam

When it all works, it’s just one of the best feelings in the world.  You dream up some concept, you band together with a group of kindred spirits, and you make magic out of thin air.  As Tory says, “Do ya think I’m excited? You better believe I’m excited. We just built a rubber moose and now we’re gonna crash cars into it. It doesn’t get better than this!

What Makes Mentoring Work

If you haven’t had or been a mentor, it’s something that is worth thinking about.  The right mentor can be inspiring, opening your eyes to new ideas and helping you tackle bigger and bolder challenges.  It can also be a lot of fun for the mentor, who gets to coach enthusiastic people without having to deal with the day to day stresses of direct management (I think it’s a bit like being a grandparent – you get to do a lot of the fun parts, without all the responsibility).  I’ve been lucky enough to have some really good experiences with mentoring, though I’ve also seen plenty that didn’t work out so well.

Picking the Right Mentor

Since this is a relationship between two people, obviously it matters a lot whether there is a good fit.  What kind of person should you look for as a mentor?  Some things to consider:

  • The mentor probably should be further along in their career, but maybe not too much further.  You want the mentor to have some wisdom and perspective you don’t have (yet).   However, if they are vastly more senior, they may not be as useful in terms of helping you get your job done.  A lot of really senior people have forgotten how to be effective at more practical jobs.  They may have really interesting ideas and advice to share that are eye-opening and inspiring (or depressing!) to hear about, but often those insights have relatively little relevance to you day to day.  So if you are shooting the moon in terms of connecting with somebody much farther along than you are, keep in mind that you may get less immediately useful advice.
  • Look for somebody with different life experiences.  When I first become responsible for a business, my background was in pure engineering.  I was lucky enough to have a mentor who had successfully created a billion dollar business within Microsoft.  He was full of insights that I desperately needed to understand, and I learned a tremendous amount from him during our discussions.  I bombarded him with questions about working with the sellers, pitching to enterprise customers, helping to close deals, and doing the crucial back office arm wrestling with the sales team.
  • It’s helpful if you have something in common.  There are many benefits of diversity, but there is a lot of evidence from relationship research that people who have more in common tend to be more likely to form lasting relationships.  I’ve found that it can be harder for mentors to really connect and add value if they come at the world with a radically different model than their mentee.

At the end of the day, probably the most critical thing about making a mentoring relationship work is “do you like each other and want to spend time together?”  Mentoring is usually optional, and everyone is very busy, so it will take an effort to get and keep meetings on the calendar with a hundred other priorities competing for attention.

What Do You Talk About?

You might get a mentor who has a very well defined notion of what to do during your 1:1, and has a plan for it.  You might also sprout wings and discover that you can fly (hey, it could happen!).  For everyone else, you want to have a plan – most mentors feel like they’ve done their bit if they have actually cleared space on their calendar and are ready to meet with you.

I like to prep for a mentoring session by bringing in a set of topics to see which ones intrigue the mentor.  I usually bring in three or four for an hour discussion, so we have good fodder even if one or two of them aren’t a success.

A couple of things that have worked well for me:

  • Pose a problem I’m wrestling with.  Obviously you will get more value if it is in a domain they know about.  For example, if they are an experienced manager, they are likely to have been in a situation similar to one you are dealing with and have ideas about how to handle it.  At least they can usually give you lots of cases where they tried things that didn’t work!  Once, I was working with a direct who was really struggling, and I talked things through with my mentor.  I knew in my heart that it probably wasn’t going to work out, but I didn’t want to admit it.  After we talked, my mentor said something that really stuck with me: “Every time I have failed with somebody, I always waited too long.  I’ve never moved too quickly.”  That’s been true for me, too.  I don’t like to give up on anyone, especially a talented person I like but who is in a role where they aren’t and won’t be successful.  Getting a trusted outsider’s opinion can help you realize when you’ve dug yourself into a hole.
  • Hunt for best practices.  Yes, I will admit that I am a bit obsessed with best practices – that’s a lot of what I write about on this blog – because I love to find tools, ideas, approaches that are really effective.  I’ve gathered a tremendous number of great ideas from other people, and I’m always on the hunt for more of them.  I’ve found that most successful people have a “toolbox” that they apply in a wide variety of situations.  Some people are very “meta” and will be able to quickly articulate those best practices.  So you can ask “When you <do some activity>, what works really well for you?” (where the activity might be anything from managing a team to doing an all-hands presentation to preparing a board review to architecting a high-scale distributed system).  Others are not so good at this, so you need to tease the best practices out by asking more specific questions: “Last fiscal year, how did you get your scorecard targets right, and what worked/didn’t work well?”  “When you built the back end for that service, how did you minimize the time to recovery when the database instance failed?  How would you change your design if you were starting over?”

As a mentor, I use some of the same conversations that I have with my directs as a manager (and which I’ll be writing up as separate posts), like “what do you want to be when you grow up?” and “how to ace your exit interview”.  These are exercises that I think can really help people introspect and come to useful insights.

Have you had great or awful mentoring experiences?  What worked and didn’t work?


Are you being a spasmodic Hercules?

I’m a fan of Anthony Trollope, who was an amazingly prolific British writer in the nineteenth century.  While working full time for much of his life, he produced 47 novels and a variety of other works.  The novels were typically hundreds of pages long and many of them are regarded as classics; if you want to try one with a lot of contemporary resonance, you might like “The Way We Live Now”.  It’s about a financial manipulator who insinuates himself into upper crust society (a terrific miniseries was made of it starring David Suchet).  How did Trollope produce such a huge body of consistently excellent work?  This quote from him offers a clue: “A small daily task, if it really be daily, will beat the labors of a spasmodic Hercules.”  He was very self-disciplined about writing, finding ways to weave it throughout his life even while he was in a demanding full time job.

Trollope’s experience reinforces something I’ve often seen and experienced – the power of habit, and conversely how difficult it is to achieve something big if you try to pursue it with isolated bursts of activity.  Some things can be done in short sprints of effort, applied at uneven intervals, but many important and transformative things cannot.  You won’t learn a foreign language or start a company or play an instrument well or get in shape, without putting in the time and doing it regularly.

This is not a new idea .. Aristotle (who managed to achieve a thing or two) wrote about it a few thousand years ago, when he said “you are what you do habitually.”  You may know about a more recent take on the notion in Malcolm Gladwell’s book “Outliers”, where he talks about the magic of working 10,000 hours to master an activity.  Gladwell has found many fields where the people who hit that number have become dramatically better than everyone around them and achieved remarkable results.  You aren’t going to accumulate that kind of experience unless you are doing it virtually every day for many years.

I think that there are two reasons why a habit can let us achieve so much more:

  • The investment adds up over time.  When we’re forcing ourselves to do something, we often have a very poor sense of how much actual productive time we’re devoting to it.  We vividly remember the times when we worked on our project, not the long stretches when we didn’t.  We also remember all the time we spent thinking about doing it.  But none of that really matters – what counts is the time you spend doing it.  By making it a habit, you spend a lot less time thinking about it or planning it or stressing about not doing it .. and your regular investments of time really add up after a while.   It’s just like the difference between saving money as a conscious act of repeated self-denial vs. having it deducted automatically from your paycheck.
  • Habits take less willpower.  This may seem counter-intuitive, but I’ve found that it’s far easier to do something as a habit.  Once you have an ingrained habit, you don’t have to constantly force yourself .. it’s just what you do.  For instance, take working out.  For the past several months, I’ve worked out pretty much every day.  At 6:15, off I go for a 45 minute session.  I don’t think about it, I don’t will myself to go, it’s just the way it is.  I used to work out regularly much less often, and then try to supplement it with additional time that I had to schedule.  And that was always a struggle – a thousand other priorities competed with a workout, and they often (usually) won.  As a habit, it just happens.

There is some good advice in this article on how to make a habit really stick – committing for 30 days, doing something daily, starting with a manageable piece, and so forth.  I thought this blog entry from Martin Varsavsky was also very interesting – he has founded seven companies, runs a large non-profit, and he writes and speaks prolifically.  He writes about how he keeps so many things going at once, and it is by having carefully streamlined his life.  He’s cultivated a set of habits that save time, and has eliminated many that waste it.  Like television.  I find many of his ideas to make sense (our family “cut the cord” on television ten years ago, and it has been a great success for us).  I radically disagree with some of his other decisions, like not reading books – I’ve been an obsessive reader since I was 4 and would be miserable without having books as a constant presence in my life.  But the point is not whether you agree with his decisions .. it’s to think about your own life as carefully as he has and find ways to optimize it for what makes you feel happy and fulfilled.

What important goals could you be achieving by turning them into habits?

Managing Up vs. Sucking Up

“Managing up” has a bad reputation – it’s often seen as a synonym for sucking up.  Isn’t it a waste of time that could have been used productively to move the team forward?  I disagree.  If you have a manager, managing up is part of your job.  And it should be.

Why Bother?

Let’s think for a minute about what a manager is supposed to do.  Among other things, they should

  • Have a clue about what you are doing and help, as appropriate (and no more than appropriate)
  • Backstop you to make sure your projects aren’t going off the rails
  • Manage up to their manager
  • Advocate and scout on your behalf
  • Understand key risks the team faces and make sure they are being managed
  • Give you guidance and hold you accountable

Now how are they supposed to do all that, if they don’t get any information flow from you?  If you’ve ever managed somebody, you may have discovered that mostly you have no idea what they do all day long.  This plays into one of the things I’ve noticed, which is that people often become easier to manage after they become a manager.

Many people push back on this idea of managing up.  They might object that

  • My accomplishments should speak for themselves, right?  Well, no.  Most managers see a tiny fraction of what you do.  They often can’t tell how much of the outcome you were responsible for.  And, they (should) care not just about what you achieve, but how.
  • Isn’t this overhead that makes us less efficient?  Yes.  Tough.  Part of the reality of being in a team is that it takes overhead to get groups of people to work well together.  Get over it.
  • Isn’t this a disguised name for sucking up?  Sometimes.  Stay tuned.

Ways to Screw This Up

From what I’ve seen, a lot of people aren’t very good at managing up.  They tend to fall into one of two traps:

  • Refusal to engage.  “I shouldn’t have to manage up – my work should speak for itself.”  If your manager is basically engaged in the same activity that you are, this may in fact be true – say your manager is a lead programmer who is in the codebase with you all day long.  But if your manager is not deeply and directly involved in your work, this is probably not going to work out well for you.  By failing to manage up, leaving your management chain in the dark, you are hurting the team and hurting yourself.  You are sabotaging your manager’s ability to do their job well.  If you hear phrases from your manager like “I feel out of the loop” or “I don’t have good visibility into this project” or “where did <this disaster> come from – I thought we were on track”, then you are probably failing to manage up well enough.
  • Looking like a suck up.  Managers vary a lot in their ability and desire to discourage this kind of behavior.  They are never as immune as they think, but even the lame ones can tell if you are really obvious about it.  Once they decide that you are a suck-up, they won’t trust what you tell them.   Your peers are also very good at sniffing it out .. and they won’t like you better for it.  Two quick tests to check yourself:
    • Are you reporting at least as much bad news as good?  If so, you are much less likely to be seen as a suck-up.  Don’t spend your “manage up” time taking victory laps.
    • Are you talking about other people’s accomplishments more often than your own?  That’s another good antidote.

When you bring bad news to your manager, they will often be inclined to start trying to fix it (with or without you).  If you want help, then that’s just what you were hoping for.  But often, you don’t want help.  You own the problem, you are on it, and you are just keeping your manager informed.  So make sure that you are clear when reporting a problem whether you want help.

Food for Thought

Here are some principles that I have found helpful:

  • Managing up is part of your job – help your manager be effective in doing their job
  • Be transparent: bad news is the news they have to have.  Don’t sandbag your management chain – they hate that.
  • Be very explicit in your own mind and with your manager whether you want help with a problem that you are reporting
  • Shine the light on others more often than yourself
  • Figure out how your manager likes to be kept in the loop – it varies a lot depending on the person

Are you doing this part of your job well?  What’s worked for you?

The Sacredness of Ownership

sa·cred (sākrid) – secured as by a religious feeling or sense of justice against any defamation, violation, or intrusion; inviolate

The word “sacred” is not one to be used lightly, but I chose it on purpose to talk about a principle I believe is at the heart of any healthy team culture: ownership.  I’ve spent most of my career building large scale software projects, and these are intensely complex systems.  No one person can understand all that complexity and track all the infinite detail of a large-scale project.  And it only takes one person writing a few lines of sloppy code to introduce a security hole that can cause tremendous damage to your customers and to your company.  The success of the whole venture rests on the decisions that the people at the front lines of the team are making every day.  So they’d better feel like they own their work, and they’d better be right!

What It Means to “Own” Something

Does “owning” something mean you get to do whatever you want with it?  No.  In defining ownership, many people focus on making decisions, which is important.  But to me, the most important thing about being an owner is that you are accountable for the success of what you own.  Therefore, the first and most important thing that an owner should do is to define success.  This sounds easy, but it isn’t, and many people do this wrong.  If you are a developer and own a feature, success doesn’t mean that you wrote good code and checked it in.  Success means that the whole feature team understands the feature and why it is needed, you coded it, you nailed the basics like performance and security, it works well, it shipped, and many happy customers are using it to solve real needs that they have.  A good owner defines success in terms of impact, not activity.  They include key stakeholders.  They feel accountable for the whole success, not a narrow part of it.

It is very tempting to define success in terms of what you control.  This is a classic mistake that people make, especially when they are early in their career.  They only feel accountable for the part they fully control.  “But I’m the developer .. isn’t it enough that I write great code that works?”  NO.  The customer does not care if you wrote good code.  The customer cares if you solved their problem.  Shareholders don’t care if you wrote good code.  They care if customers love the product and buy a lot of it.  You need to feel accountable for the whole success, even though you almost certainly don’t control it.  If you did everything right that you control, and the feature fails to be successfully used by many happy customers, then you failed.  The reason this is so important is that people generally try very hard to succeed.  If you define success broadly, you won’t settle for the excuse that “my part works – it was the other bonehead who blew it”.  You’ll go the extra mile, you’ll escalate if somebody else is screwing up and taking the whole ship down.  It doesn’t matter how beautifully you polished the handrail on the Titanic.  You still drowned.

Decision Making and Overlapping Ownership

One thing that’s confusing about ownership is that multiple people can seemingly own the same thing.  For example, the people designing a product and the engineering team that builds it all need to own what they work on.  Doesn’t that violate the whole idea of ownership?  No, if you internalize the accountability model.  All of the groups contributing must feel accountable for the whole success of their work.

Great, but then how do decisions get made?  The answer is that it depends what you are deciding.  For example, the ultimate decision maker about the way to code a feature better be the developer.  But there are other stakeholders – developers might have to do a code review with their lead or a fellow developer.  They might need to follow development guidelines set up by the development manager, so other people can understand the code and it fits in with the rest of the system.  The designer needs the feature to actually meet the user’s needs.  The developer still owns the code and is accountable for its success, but they must honor the (legitimate!) roles of other people in achieving that success.


Let’s say you are the owner and hence the decision maker.  One of your responsibilities as owner is to understand who else has a stake in the decisions you are making and what their role is.  Sometimes this is obvious, or you can just use intuition and it all works out.  That’s often the case in small teams.  But as you own more important and complicated things and are part of larger organizations, you will run into the limits of the ad hoc approach.  That’s when it becomes useful to think explicitly about the other stakeholders and their roles.

Once upon a time, the Windows team realized that decision-making was a mess – people weren’t sure whom they had to consult, who was the butt on the line for key decisions, etc.  And so things fell through the cracks or there was gridlock, and accountability was lacking.  As a result, they created a role/stakeholder model that has been used with a lot of success at Microsoft (called OARP).  There are industry equivalents (a popular one is called RACI) – which one you pick isn’t that important.  The key thing is to be explicit about the roles in a particular decision and make sure everyone understands what their role is.  Writing this down will often reveal misunderstandings (“what do you mean I don’t get to review the decision before it is finalized??!!!”) and problems (“we have to review this with twenty people before we lock the decision down?  That’s not going to work.”).  In general, the owner’s life and the team’s efficiency will improve radically as you reduce the number of reviewers, approvers, and other obstacles to progress.

Dealing With Misbehaving Stakeholders

Just because you have done a great job defining the ownership model and gotten everyone to understand it and agree to it in theory doesn’t mean that’s actually how things are going to work out.  People will frequently violate their role, often through the best of intentions.  Maybe your lead says you are the owner but they don’t respect your ownership and are always micromanaging you or giving direction to your team without including you in the conversation.  Maybe people elsewhere in the organization who are supposed to review decisions start turning into participants or are making decisions on your behalf.  And so forth – the opportunities for misbehavior are legion.  Sometimes they happen because people are too eager to help, often because people are being thoughtless, and sometimes from malice.

Your responsibility as the owner is to treat these as problems and get them fixed.  That super-helpful senior manager who comes down and straightens things out for you without you asking for help?  Problem.  Either you blew it, or that very helpful manager did, or you both did.  The participant who thinks you are blowing it as an owner and second guesses your decisions without confronting you about it?  Problem.

If someone in your management chain comes in and starts proclaiming this and that, there are two common reactions: 1) denial/rejection/anger and 2) “yes, sir, thank you”.  Both are wrong.  The right response from the owner is “good input, thanks”.  Then YOU go take action.  Don’t ignore what the manager thinks.  Sometimes they are giving you new data, sometimes advice (hopefully good).  Sometimes you are screwing up and they feel a need to jump in.  But if you are going to be a good owner, then you have to get the dynamics right.  You own the decision until ownership is taken away.  That should always be an explicit act – you might ask the manager to take over, they might inform you that they are taking over; that can be the right thing, but it is a very important change in the state of the project.  If ownership is leaving you and going somewhere else, you are no longer accountable for success.  That’s a big deal, and everyone needs to be clear about it.  You don’t have the right to demand to stay on as owner if your manager becomes convinced that you are not up to it.  You do have the right to demand clarity.

Final Thoughts

In my opinion, ownership is a crucial tenet of a healthy team culture.  How to take action on it?

  1. Figure out what you own.  Make sure everyone (including your manager) agrees.
  2. Define success.  Don’t be narrow.
  3. Figure out who the stakeholders are and respect their role.
  4. Go own the hell out of it.  Everyone is depending on you to get it right.
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