The power of looking for patterns that don't match

Pattern matching at it's most basic is about finding things that seem to fit together. 

In venture capital that often means looking at startups and interpreting what works well, or what makes a good entrepreneur. There are plenty of problems with the method - Chris Dixon wrote about a few of them in 2012, and there is significant research that suggests that pattern matching through things like gender and race may unconsciously lead to much narrower ideas of what works, and poorer outcomes for picking winners.

But one of the things that's not dug out as often is that looking for patterns that don't match is a valuable skill. Another way of thinking about it is: everyone wants to know what makes a winner, but not enough people want to know why something doesn't work, why a pattern you expected to fit, simply doesn't. As it turns out, those tend to be the underpinning to finding patterns that create growth in a company (and probably as an individual, too). 

For example, one of the most complex questions in an early stage business is: we've found something that works, but how do we know it will last? You can pattern match your way to more users or customers ("hey this works let's do more of it"), but unless you're paying attention to which patterns don't match, you'll likely get hit hard when a tactic doesn't work. There's a very small peek at that struggle in a recent update from Mike Wilner at Compass, which matches designers/developers to small business owners & entrepreneurs who need a smart, basic website.

Both sides of the coin are important. You have to be willing to seek things that don't make sense, because they can help you hedge against your own unconscious bias. And it increases your ability to see things at a much larger scale, instead of simply chasing things that fit what you've already run into. 

Countering gender bias

Negotiation is everywhere. 

Though not always obvious, negotiation rarely happens in isolation. How you negotiate in one area (like salary) immediately affects other areas (like long work hours, unpaid overtime, and possibilities for promotion). 

One place where this is critical is the powerful, often unspoken, element of gender bias. For women and non-gender binary confirming individuals, “good” negotiation is a double bind. You sometimes have to play the game the way that men do, but you also face punishment for reasons that are difficult to call out (think Hilary Clinton being attacked for being “too aggressive” vs. criticism for being “a weak leader who cries in public”). 

It’s a very subtle line to walk, and there’s already great deal of research into how gender bias works… 

The Ellen Pao suit against VC firm Kleiner Perkins from earlier this year illustrated how troubling that double bind truly is. If you pay close attention to workplace dynamics, many of the scenarios from that case, like preference in seating charts, will sound familiar (some of Pao’s testimony is here, and the full stack of court documents is here). 

And while hidden negotiations and bias have implications for people on the unequal side of a power balance, it also, as the HBR piece from above suggests, has an effect on everyone. Creativity, productivity, autonomous decision making, and quality of work all suffer when gender bias is at play. 

But how do we realistically and practically combat gender bias when it is hidden in so many cases? Here are a few insights from a recent email exchange I had a few months ago with two of the smarter folks I know who work in technology / startups… 

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Letting people fail

If you’re anywhere near the startup ecosystem, you’ll consistently hear the mantra of “fail fast.” 

Personally, I’d rather focus on the outcome, which is / should be about learning fast. But failure does teach us…and if we’re paying attention it gives us information that we can take further than the specific moment or situation. 

What gets less attention is the importance of letting other people fail, and that’s a shame because it’s a critical skill that isn’t well understood or talked about enough. 

Mentoring / advising, for example, has a lot of moments like these. Good mentors understand that you can’t control a situation, nor can you save someone from themselves. 

It’s useful to break that moment down, because where people need to fail and learn from that failure can be subtle. 

As a mentor it often looks something like this for me: 

  • Big problem or set of complexities, entrepreneur recognizes they exist and tells me about them
  • I clarify what’s happening to make sure I understand, then try to help them frame their own understanding
  • Here’s the important moment: Entrepreneur looks at me and says or implies outright “this sucks / I don’t know what to do / this is really hard and/or complex”
  • Even if you’re a good mentor (friend, boss, etc) it can be easy to skip right to “ok here’s how you fix it” or “why don’t you try X.” 
  • In reality, what needs to happen in that moment is that the entrepreneur (friend, family member, employee) has to recognize the structure around the problem they’re having, and you can’t make them do that. 

This can happen in a personal or professional context. The key is to understand that there is a choice involved.

If you are the person working through the problem or set of complexities, sometimes it means realizing you are in a bad piece of structure that you need to get out of. Sometimes it means recognizing that you’ve created some or a lot of that structure. Often it is both. 

If you are the person helping or advising, this process can be uncomfortable. The person may ask you directly to do something that you don’t feel will help them. Or you may care about the person and their growth, and want to make sure they don’t experience hardship or pain. 

Here are a few questions that help me avoid skipping steps, and prompt the entrepreneur to do their own work. 

  • “That sounds intense — how would you like to structure our time so I can be of help?” *suggests that they should ask for / define what help they need
  • “How are you thinking about approaching the problem?”
  • “What do you think needs to happen for you to work on it?”
  • “Is there a general beginning / middle / end that you see for solving this?”
  • “What information do you think you need to solve this problem and/or where do you go to get that?”

I’m speaking mostly here about entrepreneurship, but you can apply this approach to most situations, including co-workers, family, friends, significant other, etc. 

Letting someone fail can be one of the most graceful and compassionate things you do, and if you’ve created a supportive work environment, friendship, relationship, etc. they’ll learn fast and be on their way to greater things. 

 

On why belief matters, and how information is coded into experience

Every day I go for a walk and pick up trash.

Although there a lot of reasons for it, the two main ones are:

  1. It needs to be done — (a matter of faith / belief)
  2. There is information coded into the experience that I can’t otherwise get to

That first reason is quite simple to break down: I don’t believe that there should be trash on the streets. 

The second is a bit more complicated, and reaches into a bunch of things— like human centered design / experience design, empathy, entrepreneurship, and how we build ecosystems from an individual up to global level. 

There is an important relationship between the two, and it’s a relationship that’s largely about action, about testing what we believe and what we are most suited to work on in the world. 

In the startup ecosystem this is expressed via investors saying things like “we want founders who are obsessed with solving problems” or founders saying “I won’t rest until I’ve understood and solved this problem for my target customer / market.”

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Telling one story a day about the people who use what you create

Building a company from scratch is exhausting. 

Entrepreneurs need various kinds of support to stay afloat —understanding friends and family, tough advisers / mentors, a good reading list to encourage contemplation, these are all important.

But the best source of support is the people actually using what you build. Their stories are the ones that open up your world when you’re thinking too narrowly, and provide inspiration to keep going. While solving a problem for one person typically doesn’t justify a stable small business or a rapidly growing startup, it’s the starting point for everything else. 

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