Doing the work is more important than celebrating entrepreneurship

There’s a great phrase that a friend of mine from Boulder uses often. 

She calls it “doing the work.”

It’s one of those things that seems obvious, but isn’t well understood by startups or founders. 

Sometimes that’s because of ego and/or too high a degree of self-awareness, and sometimes it’s simply because “doing the work” can be a slow, painful process without much worth celebrating. 

Doing the work isn’t about appearances, it’s about the value actually delivered or created. 

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A strong culture isn't about what happens when things go well

Startups and corporates both constantly preach about the importance of culture.

It's something that's supposed to attract and keep the hardest working and most talented folks, and people who lead teams or found companies like to brag about how good their culture is, and how much everyone likes working there.

But good, deeply creative culture has nothing to do with sodas in a fridge, ping pong tables, bonuses, awards, or praising people.

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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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Where creative projects go wrong

Over the years I’ve worked with creatives on projects that include graphic and website design, physical product design, and UX / UI for apps and online platforms.

There are a few ways for a project to go to hell and leave everyone hating the process. The most common is when the ideation doesn’t match the expectation of the client (can be internal or external), even though they might already have approved it. 

Anyone who’s managed a project with a design component will recognize the cycle… 

  1. The ideation is approved, but is slightly broad / general
  2. Creative realizes they have room to stretch and gets excited, or conversely, plays it safe — leading to a 1st draft that is either specific but not what client had in mind, or overly generic
  3. Client provides extremely detailed feedback on a piece of work they don’t really like, which confuses the process
  4. Creative gets frustrated trying to fix something client doesn’t like, or creates entirely new draft which may or may not please the client (who by this time isn’t always sure what they want)

The critical moment usually happens between #2 and 3. At this point it’s still fixable but deadlines are tight and depending on how many people are involved there may be some serious frustration. 

What has to happen but often doesn’t, is a very timely, concise revisiting of ideation with the end client. You can’t fix wrong or misaligned ideation with more design, no matter how good the concept is to begin with. 

One other note: the phrase “end client” is an important one. A good project or product manager can sometimes alleviate confusion between the different people who are involved (brand, legal, marketing, PR, etc.) but whoever will actually own the end result needs to approve the ideation. That doesn’t always happen, and it’s also why big agencies rarely run a tight enough design communication cycle to avoid cost overruns. But that’s a topic for another time.