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The collateral damage of a missed opportunity

May 21, 2009

Sometimes life just steps right in and provides an illustration of a key principle, almost as if on cue. My apologies for the length of this, but the topic merits it.

For those of you who have read my bio, you know that I work in Seattle but commute from a small town in the Midwest. There’s a separate blog post needed to explain why, but the town I live in is small enough for us to know everyone, and be very actively involved in our community.

Last week someone at our high school wrote racist comments, a death threat, and the names of a number of the black students at the school on a stall door in one of the boy’s bathrooms. No ambiguity here. Horrible, fundamentally unacceptable, reprehensible thoughts. Scary too.

How the school responded to this presents a crystal-clear example of how ambiguity + fear of failure = colossal missed opportunity for a community and for its students. And it offers a heartbreaking follow-up to my post last week about ambiguity and alignment of your principles and ethics.

Here’s what happened:

  • A death threat naming six of the high school’s black students was discovered on a bathroom stall door at around 2:30 pm last Thursday.

Here’s what was done:

  • The six students were pulled from class that same day by the administration, informed of this, asked if they knew of anyone who might have done this.
  • The next day the police department was pulled into this, and spent the day at the school investigating the incident.
  • This same day – the day after the discovery – the administration met with the six children’s parents.
  • A letter was finally sent home to students this past Tuesday, identifying this as a student safety issue, and stating that “racist or threatening behavior will not be tolerated.” You can see it here.

Here’s the issue. With one exception, what they did wasn’t wrong, it just could have been a whole lot righter. And bolder. And more educational, for everyone.

The one thing they did wrong? Waiting until the following day to tell the parents. My heart goes out to the parents of those six children when those kids came home and told them what had happened at school that day. How alone they all must have felt. I don’t need to dwell on the tragedy here, the local Fox affiliate got there way before me.

So, the police got called in to investigate, and a letter went out to the students and parents. A safety issue. My daughter summed this up well by saying it screamed ‘this is not our fault.’ I was profoundly let down, feeling decisions were guided by a desire not to fail, not to make a mistake, and to minimize the visibility of this incident.

Retreating to this being primarily a safety issue is a red herring. This is unequivocally a racism issue. And it’s not about the high school. It’s about the entire community. Whoever wrote these threats does not live at the high school. Any one of us may be running into this kid on a ball field, in a supermarket, anywhere. The school provided the medium for the expression, but those racist thoughts leave the school ground at 3:05 and go somewhere.

The school administration got the whole visibility opportunity wrong. They claimed raising visibility would satisfy “that person’s need to do it and maybe there is more that will happen.” Huh? I can’t think of a better way to ensure this doesn’t happen again than getting the entire school and community to get out in public, now, and express their opposition to this kind of behavior.

And “out in public” is where the six students and their families need to feel supported, and safe. These six children and their families should feel comfortable knowing more than the school and the police are looking out for them. Worse, time matters here, a lot. These children and their families needed that support the moment this was discovered. Importantly, the opportunity for members of the community to show their support in a timely manner was also taken away too.

What if the actions were guided by a fear of not succeeding? Success is not about catching whoever it is who wrote the graffiti. It’s about demonstrating unambiguous intolerance to racism, in the school system and community as a whole.

How could this have been handled differently?

  • They could have held a school-wide assembly to inform the students not of the threat as much as of the intolerance of racism. Of the vigilance to eradicate it.
  • They could have called a joint City Council-School Board emergency public meeting to shine a bright light on these two institutions’ intolerance to racism and vigilance to eradicate it.
  • They could have held a community-wide rally to ensure no one missed an opportunity to show support for these children and their families.

Hiding this or minimizing its visibility means that if whoever it is who made these threats is never caught, then he or she or they will have won. Even if caught, the legal process will be conducted in rooms, in buildings, away from the community.

What a spectacular opportunity to bring the community together and shine a big, bright light on this. And what a colossally great learning opportunity, missed. My daughter is taking a “Race, Prejudice, and Intolerance” class in that very school, right now. Holy cow, why not get the entire student body in on a real-time lesson. How many people can say they’ve taken part in an anti-racism activity, as a student, in their own school?

And that list I came up with about how this could have been handled differently? It can all still be done too.

And this isn’t personal or about the people involved. It’s about the direction they chose. I know the school principal and many of the school administration and teachers. These are smart, caring, very hardworking people. People that make you proud that they do what they do to provide a great education for our kids. That’s why it’s so heartbreaking to witness the straightforward, sensible path that produced this missed opportunity.

A fear of failure produced this. Nothing done wrong, but plenty of collateral damage, and six students, their families, and the community poorer for the experience.

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Posted in Empathy, Failure, fear of not succeeding, meaningful failure, Success, Values | 9 Comments »

Ambiguity and alignment

May 13, 2009

My last few posts have been very much “inside the world of vc and high tech” and I wanted to get back to the broader theme that underpins this blog – meaningful failure and what you can learn from failure.

I had one of those wonderful experiences last week where a friend connected me to a friend, and I subsequently found myself deep into a conversation I hadn’t expected.  In this case, I was on the phone with a former technology executive who left his career to pursue his passion for poetry.  There we were, getting to know each other, locating some common ground in our shared interests of startups and writing.

One of the subjects we lingered on was how whether you’re at work or at home, you’re the same person deep inside.  And that the converse is perhaps more interesting: what happens when you’re a different person at work than you are at home?  I was thinking alignment of values and areas of ambiguity.  This sent me in an interesting arc.

When I first started thinking about this I thought the issue was more about decency and less about ethics. 

Except people can be incredibly decent, treat others well, communicate compassionately and still be unethical.  They can define “truth” in a way that is not true at all, and exploit this ambiguity motivated by fear, or greed, or insecurity, you name it.  But it means who they are on the outside (defined truth) is different from who they are on the inside (actual truth) 

Which made me think of Entellium.  This is old news, but offers a rich example.

Entellium was a high flying venture capital backed startup in Seattle, where the CEO and CFO created a second set of financial statements that overstated revenue and presented these to their employees, board, and investors. Only these two executives knew about it, and they compartmentalized the truth, keeping it deep inside.  For a long time. 

John Cook of TechFlash summed it up well:  “More than $50 million in venture capital down the drain. Over 200 people out of work. And two Internet executives — both fathers — going to federal prison.”

They didn’t do it because of greed – they didn’t even profit from this deception.  In fact they ended up spurning a $100million offer from Intuit, knowing the fraud would come to light during the accounting review.  

One of the executives admitted the fraud was driven by the fear of failure.  A missed sales objective one quarter and the fear of confronting that caused them to overstate actual revenue.  And then the next quarter of course they were even further behind, and well you know the way these things play out.  So, they lied to their board and employees.

And to their families too, who were blindsided by the fraud.  The police showed up at their houses and took the execs away in handcuffs in front of their wives and children.  Imagine what was going through their heads, and the heads of their families in those moments.   And the comment I kept hearing from people who knew both men was “they were such decent people.”

So I guess you can be decent and have a very ambiguous ethical foundation.  In fact, the belief that your your ethical foundation has ambiguity is the tell-tale that you are no longer behaving ethically.  Entellium was all about the difference between what was true and what could be gotten away with.  There’s plenty of ambiguity to go around in those last six words. 

But deception is a whole number, there are no fractions of it.  There is no ambiguity.  So it’s really not about being a different person at work or home, it’s about always being the same person inside and outside.  Having truth be the connective tissue between the two.

David Foster Wallace said this well in his 2005 commencement speech at Kenyon College “The trick is keeping the truth up front in daily consciousness.”

If it’s up front, then it’s there for everyone to see.  A nice alignment between who you are inside and who you are outside.

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Posted in Empathy, Failure, fear of not succeeding, meaningful failure, Self-knowledge, Success, Values | 9 Comments »

A-players hire A-players, B-players hire C-players

April 28, 2009

This is one of those sayings in the startup world that is so accepted that it’s crossed the border of familiarity and become a full-time resident of the land of trite.  

Guess who coined it?  Steve Jobs.  That’s right, Steve Jobs, when he was getting the Macintosh off the ground.  It’s a phrase we used at RealNetworks a lot, and one that my partners and I use as a result. 

But that it’s trite doesn’t mean it isn’t relevant or true.  It is.  Absolutely. 

And it’s a subtle but important concept to really understand.  What do A-players do for you?  Everything.  Most important, it’s the tone they set in the organization and their influence on the behavior and performance of others. The hiring is critical too, but that’s a byproduct of everything else.

  • A-players are at the top of their game.  This means they know the difference between good and great.  In the work they do, and in the standards they set for those around them and those in their organizations.
  • A-players aren’t threatened by someone better than they are.   Rather, they’re relieved.  That stuff they were struggling with?  They’re happy to get that into the hands of someone who can run with it, faster and more nimbly.  How liberating.
  • A-players know what they don’t know.  A corollary to the point above is that A-players know when they don’t know something, and ask questions.  They have the security to not need to know the answer to every question, and know how valuable intellectual curiosity is.
  • A-players can’t tolerate C-players.  So they make sure the C-players are replaced.  And guess what? The rest of the organization is relieved and inspired.  They know who the C-players are, and have felt the drag on performance.  It may sound harsh, but it’s true.

To me the most essential capability A-players bring to an organization is the tone they set for it.  Their definition of “good” is so much greater than a B or a C player’s, it’s as if they’re speaking a different language.  In fact they are, and it’s critical the organization you’re in all speak the same language. 

This is why starting up companies is so liberating for A-players.  I remember when I was at LSI Logic in the early days, fresh out of college with my head spinning in this startup.  The CEO, Wilf Corrigan, made a comment to me once about why he loved being CEO of LSI Logic so much more than being CEO of Fairchild Semiconductor (which he had been before founding LSI).  He said “because I created a company with only people I wanted to have there, not ones I inherited.”  At the time the answer sounded sensible, but now I realize what he meant was he could hire A-players from the start. 

But don’t get me wrong.  A-players are not a homogenous bunch.  There’s a huge, huge spectrum of abilities and characteristics among them.  Some can be incredibly thoughtful and compassionate, others can be intellectual bullies and seemingly heartless.  But the connective tissue that binds them all together?  They know where to set the bar/standard and how to hold themselves and everyone around them to it.

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Posted in chicken killer, Empathy, fear of not succeeding, Intellectual curiosity, Self-knowledge, Values | 4 Comments »

Man On Wire – Best Startup Movie Ever?

April 1, 2009

I saw Man On Wire for the first time in February; I’d read a snippet somewhere about this being the story of the man who tight-rope walked between the two World Trade Center towers in 1974.  And at a certain level, that’s exactly what this movie is about.  It’s exquisite.  The tight-rope walker, Philippe Petit is almost a caricature, his vision and ambition equal parts boundless and focused.  I’ve seen the movie three times now, and each time it’s more revealing.

What viscerally strikes me is how it tells the story of starting up a company.  This is all about having an idea so audacious it’s almost not believable to someone who hasn’t drunk your kool-aid, yet.  It’s about staying focused on the one reason why you will succeed and not the 10,000 reasons why you will fail.

Man On Wire reveals four super-compelling principles that underscore what it’s like to be in a startup, and if you haven’t been in one, it’s a wonderful way to get a sense for what it feels like to be there:

  • A meticulously constructed plan, discarded.  Philippe Petit spent six years planning this act, including building scale models of the towers’s roofs, constructing a tight-rope the same length as the towers in a field, and on and on.  And guess what?  The day of the “coup” huge elements of the plan had to be thrown out, the real world just didn’t cooperate.  This is “why the numbers in your operation plan are wrong” writ larger than life.
  • Repeated visualizations of the outcome.  This is one of the critical mechanisms to ensuring you’re focused on why you will succeed.  Philippe from the moment he learned of the Towers construction, visualized walking between them.  For years and years visualized walking that wire, how he would do it and succeed. This is critical when you only get one shot at an opportunity, like he had. 
  • Significant emotional toll.  Getting something done that’s ambitious, with a visionary leader means you will do things that are difficult and way outside your comfort zone.  You will find out who the chicken killers are, who can be relied on and who can’t, and most importantly what you can rely upon yourself for.  It’s messy and painful, and you will be different as a result of this experience.
  • The fear of not succeeding.  Philippe’s obsession was on success.  Startups are all about being laser focused on why you will succeed, and your only fear is success NOT happening.  I just can’t say this enough.  People who are afraid of failure may very well get great things done, but just not at startups.

For me the most piercing and fiercely honest confession of the entire movie is when Philippe describes the moment when he committed himself to walking that wire.  A simple shifting of weight from the foot resting on the tower to the foot resting on the wire.  Silent and internally deliberate. 

Compare/contrast this with the article in this April’s Outside Magazine about why people participate in risky sports, and profiles BASE-jumper Ted Davenport.  Neuroscientist Russell Poldrack asserts that there are three ingredients to risk taking: desire for adventure, relative disregard for harm, and acting on your desires without fully thinking them through.  That last factor strays way, way too far into the landscape of recklessness and separates Philippe from Ted.  There was nothing reckless about Philippe Petit.  Deliberate, honest, ambitious, meticulous.

So see this movie for the reasons I outline above.  Also, let yourself ask the other questions.  Like “how can someone afford to spend six years planning this”?  How “real world” is that?  We’re not getting the full story here, but it sure is enjoyable. 

Before your Netflix delivery arrives watch Philippe break Stephen Colbert out of character on the Colbert Report, and you’ll hear Philippe describe that moment when he shifted his weight onto the wire.  Mesmerizing.

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Posted in Business planning, chicken killer, Failure, fear of not succeeding, Intellectual curiosity, meaningful failure, Self-knowledge, Success, Values | 1 Comment »

Effective networking – as easy as public speaking

March 19, 2009

Over the past few weeks I’ve had a series of conversations with people about what makes an effective networker, and following up my post about the Seattle 2.0 Awards event, “networking” seems like a timely/relevant topic.

To me networking is the ability to develop a real and sincere personal relationship with someone around a topic that the two of us find interesting, relevant, and important.  It’s bidirectional, about giving and getting.

No surprise it has nothing to do with LinkedIn or Facebook.  Just look at the About LinkedIn page: “We believe that in a global connected economy, your success as a professional and your competitiveness as a company depends upon faster access to insight and resources you can trust.”  This is under the heading Relationships Matter.

Wait a second, this is about stuff for you, it’s not about relationships. 

Networking is about taking “what goes around comes around” to heart, and focusing on what you give to someone, beginning with an understanding of that other person.  It’s creating some durable residual value through a conversation, and the goal is to produce a lasting memory of you and your talent/intellect.  Along the way they’ll learn about you, but that’s secondary; it’s the byproduct.

OK, but this can be scary to do.  You are going to reach out to someone you don’t know or know well and ask for something.  In some aspects, this puts you in a situation similar to public speaking (and we all know how comfortable that can be for people).  You need to “perform” and expose some vulnerabilities.  It gets a lot less scary for me when I don’t view this as networking, and instead view this as a way to form and nurture a personal relationship.

Perhaps in this first conversation you do have a favor to ask, or maybe you just want to establish the relationship, or have this person keep an eye out for a role or opportunity relevant to you.  It’s this slice of memory that will provoke them to make the introduction you just asked for, remember your name and repeat it to a relevant contact, or to take your call and grant you a favor someday later when you ask it.

I do this all the time for people, and I don’t mind it one bit.  As a matter of fact, I love it.  I just did it while writing this post.  Someone I know has taken on an ambitious consulting project, and a former colleague of mine who has since become a rock-star marketing exec could help her out.  I loved connecting them, a good fit of two thoughtful, talented people –  who I have real and sincere personal relationships with.

This is taking your values as a person and applying them in a professional context (something I touched on in an earlier post) and doing this in an interpersonally “deliberate” manner. 

And then I thought, well there is networking I hate and am not comfortable with.  It’s the “forced” networking of work-related events – when you’re in a crowd and making the small talk that on occasion produces an interesting and memorable discussion.  This is perverse because in my role as a VC a big part of my job is to get out into the market, to attend events, and to “network.”  I am horrible at small talk, and I admire people who can establish ease and comfort quickly with someone new, and find some common ground.  I am still learning here.

But I approach this in the same way I had to learn to speak in public.  It doesn’t mean I’m always comfortable, it just means I’ve trained myself to do it.  And there are a lot of conversations along the way that just seem to fill space and time, but there are also those moments when I meet someone where we can establish an actual, meaningful conversation.  And then I’m right back in my comfort zone.

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Posted in chicken killer, Empathy, fear of not succeeding, Intellectual curiosity, Self-knowledge, Values | 2 Comments »

Guest post coming Monday

March 13, 2009

I wanted to let you know that OpenAmbition will be showcasing its first guest post, from Jenny Hall, former CEO of Trendi.com, which was a social networking destination focused on young women’s fashion that was shut down in October of 2008.  Jenny will be sharing what she learned as a first-time CEO through the success and eventual failure of Trendi.

I met Jenny the first time a little over a year ago, when she was trying to raise a Series A financing for Trendi, and for  reasons I explained to her, my partners and I were not able to fund her company.  Jenny touches on a few of the reasons in her post on Monday, but in many respects, what she describes are what many entrepreneurs wrestle with in an emerging but crowded market, where so much is learned in real-time. 

Like with many of the entrepreneurs I am fortunate enough to encounter, she and I have kept in touch, and when she stopped by my office a few weeks ago to tell me about her next startup idea, the subject of Trendi of course came up.  Jenny talked me through some of what she had learned, and how valuable the failure of Trendi had been for her personally (but not painless for her, for her employees, or for her investors). 

When we moved on to discussing her next startup idea, it was inspiring to see how much was informed by what she had learned through Trendi’s failure, how she had embraced what many would have tried to forget or move on from.  And so it seemed like she had a story to tell that the followers of this blog could relate to, find interesting, and hopefully find some meaning in too.

I hope you all enjoy it, look for her on Monday.

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Posted in Business planning, chicken killer, Failure, fear of not succeeding, fundraising, meaningful failure, Self-knowledge, Success, Values, Venture capital | Leave a Comment »

Peripateia and the value of getting it wrong

March 9, 2009

One of my kids favorite TV shows is “Dirty Jobs”, and I have to say that what I’ve seen of it, I have liked, because the host Mike Rowe comes across as genuine and inquisitive.  He’s there to understand, not to judge.  That alone is a wonderful set of values for children to see and explore, regardless of medium.

So, when a friend forwarded a link to Mike Rowe’s TED talk  (embedded below) on the merits of hard work, my intellectual curiosity was high.  His job is to question assumptions and to get all of us to understand the real, human aspects of jobs that other people are unaware of or assume just get done. 

He talks about how he’s “gotten it wrong” a lot, but that getting it wrong informs the essence of what he does and how he does it.  He shares the meaningful failure he encounters as an apprentice on a sheep ranch where it’s his job to castrate the lambs. 

He does his research ahead of time and determines the “humane” way to perform said castrations (with a rubber band).  Then he gets to the ranch, and finds the castration performed there is quite different (with a knife, and more); on the surface a more grisly method than he or we could have imagined.  Let’s just say that this would make killing an actual chicken seem simple and an easy choice.

But in the process of telling the story he introduces the concept of peripateia – the sudden or unexpected reversal of circumstances or situation (remembering it from his days studying Greek classics).  What a wonderful way of describing meaningful failure. 

Mike’s castration dilemma is so clearly framed, his assumptions apparent (“the ‘humane’ way is the right way”) and then, through first-hand experience, not only questions that assumption, he casts it aside when he realizes the definition of “humane” needs to be questioned. 

He describes in twenty minutes what some entrepreneurs I know have taken years to internalize, and he draws on some key themes I’ve explored:

  • Getting it wrong is something you need to embrace, it’s what enables you to both perform better and to comprehend your purpose and goals more insightfully.  It’s meaningful failure from another point of view.
  • You need to know when to stop what you’re doing, and question your core assumptions.  This is hard, as I’ve mentioned in previous posts.  When he stops what he’s doing, he demonstrates incredible integrity and purposefulness.
  • Facing up to the unfamiliar, the unpleasant, is precisely what presents you with the opportunity for discovery and learning, and improving the quality of your results.  This is a benefit of chicken-killing I hadn’t thought about.

But the impact of Mike Rowe’s honesty doesn’t stop there. 

He has a transparent methodology (no takes, no scripts, it’s all real) that underpins the credibility of his “product”.  What I loved about this anecdote is that he even had to question that foundational element of his show; he had to stop the filming because his core assumptions about the subject matter were so precarious.   That takes experience and a confidence in your process and values.  He didn’t rationalize, he didn’t talk about the cost of stopping production, he just did it because he knew he needed to.

Back to peripateia.  That doesn’t exactly roll off the tongue, but what an elegant term to describe how you bring meaning to failure, from getting it wrong. and finding meaning from the doing.  I want Mike Rowe on the board of the next company I fund too.

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Posted in Business planning, chicken killer, Failure, fear of not succeeding, Intellectual curiosity, meaningful failure, Self-knowledge, Values | 3 Comments »

Ask, Tell, Help

February 18, 2009

How often do you encounter a a situation at work where your personal values inform how to solve a difficult/ambiguous situation?

In 1998 I had just joined RealNetworks, and was running the RealSystem G2 launch; it was quite an adjustment professionally.  Real had just acquired Vivo Software where I had been the VP of Marketing, and I now had a much bigger job, with much bigger company ambitions.  G2 was Real’s next generation internet media platform, and was intended to become essentially a multimedia operating system for the web.  We never spoke those ambitions publicly, but they were very, very much the ambitions.

We had the upper hand on the internet a/v market.  Microsoft’s Windows Media Technology (WMT) platform was embryonic and poorly integrated across their vast product/platform landscape.  We routinely pushed the Windows Media guys around like how the New England Patriots pushed their opponents around.

But these were the conditions that provoke a response from Microsoft, and I remember the day we learned that Will Poole had been moved to Windows Media from Internet Explorer 4 – the understanding being the “A” team was now on WMT, the same team that had just crushed Netscape. (The Patriots analogy is eerily relevant here – I’ll save that for another post).

Two years earlier we had licensed RealSystem4.0 to Microsoft, and their players could play back our content up to version 4.0, but not our newest G2 content.  This was intentional and was common practice back then – a way to “provoke” upgrades.  We’d get our broadcast customers to produce audio and video in our newest version, and everyone would need to get the new RealPlayer to access the new content – our players were explicit and helpful about how to do this.

Microsoft saw an opportunity.  They made the Windows Media Player automatically become the default player on someone’s computer for our 4.0 content without telling them, and when it got to our G2 content it stopped and produced an error message.  Microsoft made sure the error message was cryptic (a core competency, apparently), implying there was something wrong with Real’s product, and that was it.  End of the road.

This caused a furor for us and our customers.  Competitive technology geopolitics at Cuban Missile Crisis levels.

So, I got called into a meeting with all the senior execs at Real to sort out what to do.  Our president (at the time) has an incredibly insightful mind, and summarized the problem as if he were explaining it to a child.  “Look, during installation you should ask the user if you can play other media types, then you should tell the user if you encounters one you can’t play, then you should help the user locate a player that can.  Pretty simple stuff.

But he wasn’t talking about a solution to this geopolitical skirmish, he was talking about his values, and applied them to a situation at work.  It was so simple; you ask for something before taking it, you tell people if you have a problem, and you help people.

So, I got tasked with spearheading the Ask, Tell, Help initiative, and spent the next six months rounding up industry support for this, eventually causing Microsoft to sign on.  The legacy is visible today to anyone installing iTunes, Rhapsody, or Windows Media – the application asks you for what media types you would like it to be the default.

I think about Ask, Tell, Help pretty frequently.  It reminds me that my values are my values regardless of whether at work or home, regardless of how charged or ambiguous the situation is.  And keeping clarity about those, and a tight grip on them, enables successful navigation of difficult circumstances.

Don’t you think, or rather don’t you desperately hope, that the folks who had a hand in the mortgage/banking crisis would have made different decisions if they’d have applied their personal values to the ambiguous and charged landscape of credit default swaps?

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Posted in Business planning, Empathy, Intellectual curiosity, Self-knowledge, Success, Values | 3 Comments »

Why “I don’t know” is a great answer

November 27, 2008

Here’s a news flash: You can learn a lot about someone by asking a question and seeing how they answer it.

 

That’s so obvious, and we’ve all heard it a million times. I spend a lot of time listening to pitches from startup company CEOs, as well as spend a lot of time with the CEOs of my companies, and in both cases, end up asking a lot of questions.

 

The questions, that’s where the really hard part of making productive use of time is. Anyone who has the ambition and the drive to start a company is generally smart, and has spent so much time on their business that they’re awash in information about it. Anyone who is CEO of a startup is the same way, except they’re not pitching a vision to you, they’re living and managing it. In either case, it’s their job/role to have anticipated the key questions, and have the answers to them.

 

So, it’s hard to ask questions that dig below the surface, that reveal something that hasn’t already been thought of. If you’re lucky enough to have thought of one, it can accelerate everyone’s understanding of the business and the people running it. Conversely if you’re the CEO, when those questions are asked, it will put you in a potentially awkward position. Do you have an answer, and should you have had an answer.

 

This is true about life in general, so while what follows is specific to my job, I find it’s the same calculus with friends, spouses, children, parents….

 

I love it when we get to that juncture and the CEO says “I don’t know the answer”. It’s even better if they then say “there are a number of ways to try and answer it, let’s start….”. Now you’re about to take a trip to a very rich landscape indeed. A landscape where you’ll find out something potentially valuable about the company, about the CEO, and about your ability to work together to solve problems.

 

But there’s another direction that frequently gets taken. When the CEO produces an answer. I choose that verb deliberately. The answer is produced right there, like a big patch applied over a void. The void is hidden, not explored. This is where ego and insecurity hijack intellectual curiosity and drive it right past a tremendous source of opportunity.

It’s where the person being questioned feels the need to have an answer for every question, that somehow exposing that they don’t know is bad or weak.

 

Once you become familiar with the “answer for every question” mentality, it becomes a warning sign of significance. I hate it. It spoils all the fun. Worse, it destroys credibility at an alarming pace, but in a very quiet and nuanced way – because you can’t possibly have all the answers in a company that’s still more vision than substance.

 

And it turns out, the people who most often fall into this trap are the folks who have left the large technology companies to start up a company. It reveals the culture they had to navigate through to succeed in the “big company” world. The problems generally were so well understood you could have and were expected to have all the answers. And if you didn’t, you could “patch and pivot”, loop back, and get the answer – accountability was so diffuse, and decision cycles so long.

 

But what gets missed here is that the answer isn’t important, at all. It’s seeing that juncture where you don’t know the answer – that’s the super valuable piece of information. That may tell you about a core set of assumptions that are off, or an area of opportunity that’s been missed or overstated.

 

I love the landscape that is revealed in not knowing the answer. I love working with people comfortable with traversing it. I love it when a CEO sits me down to talk through a tough problem, and will state the truth: “I know I’m missing something here, help me figure it out”. When I hear that, I know the fun is about to begin.

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Posted in Business planning, Intellectual curiosity, Self-knowledge, Values, Venture capital | 3 Comments »

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