One of the lessons people regularly reference is having the courage to ask for what you want.
That’s a common theme in startups — and it applies in a lot of places, including more traditional workplaces, and in personal relationships.
But asking for what you want doesn’t guarantee it’ll look / feel like what you expected, or that you’ll even want it when you get there.
Read MoreIf 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:
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.
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.
It’s always interesting to ask entrepreneurs what they think holds a startup together.
The answers vary — sometimes you’ll get a basic answer like culture, or hiring. Other times people will talk about measuring things and setting goals, or the ability to follow one’s passion.
Those are all good answers, but for me the most basic quality of entrepreneurship is really just emotional resiliency.
I wrote about that topic the other day, and about how accelerators help entrepreneurs develop emotional intelligence. I think when the people who work for and are around an accelerator care about helping entrepreneurs grow that resiliency, that has a lot to do with later success.
You can clearly see this in two of the world’s best accelerators, Techstars and 500 Startups.
Read MoreEvery day I go for a walk and pick up trash.
Although there a lot of reasons for it, the two main ones are:
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.”
Read MoreYesterday one of my roommates and I talked about the lack of diversity in tech / startups.
In particular, we were thinking out loud about pipeline problems. In plain English that just translates as: how to get a set of good, qualified applicants who aren’t all white, male, and from upper economic tiers.
This is a fairly regular conversation for me. It’s also something I’ve worked on in startups and corporate, at times directly via hiring and at times by supporting other people involved in or responsible for the process.
Even the best founders / tech companies struggle with this. It’s common to hear people say that they are open to having a diverse hiring culture….and then find out that they don’t know how or aren’t willing to make the effort beyond posting jobs in a few obvious places. This is usually followed by wondering why they seem to get the same type of applicants.
Other people have written extensively about why you might want to have a diverse hiring culture with respect to race, gender, sexual orientation, and other categories, so I won’t do that here…if you are looking for stats and research for the whys, here’s a good / fairly comprehensive resource created by Brittany Laughlin, GM of the Union Square Ventures Network and multiple times an entrepreneur.
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