Hard Conversations

Consider this- whenever you feel uncomfortable about something see that as a sign of progress. If you are uncomfortable confronting something then put that to the top of the list. Ask the hard questions first. The real key to success in business, and I think somewhat in life, is being willing to have hard conversations. Almost as important is having them happen quickly. Like punishing a dog right after it pisses on the rug- the "conversation" with that dog loses all meaning within 60 seconds. If you let too much time go by you lose the clarity of the conversation- memories get fuzzy and facts evaporate. That applies to conversations with yourself and others.


The companies I see fail, or fall into decline, are often taken down by leadership that shied away from hard conversations. At the heart of those conversations are usually real truths they don't want to address out of fear. They put them off since it makes them uncomfortable and it only creates bigger harder problems to push off again later. Eventually they melt down and have the hard conversations, which have only multiplied, but it's too late. They are in a weakened position and can only confess to screwing up, they have lost all leverage. I am speaking from experience here, more than I would like to admit to.


Business rewards the brave who don't let fear sabotage potential.

Idea: Making Indy "Cool" with Cultural Micro-Loans

At a recent Meridian Institute event at the IMA there was a panel discussion that nicely devolved into asking the age old question- "How to be cool?"
The question was framed by one of the panelists- Kristian Andersen, a friend and business associate of mine.

Kristian essentially answered his own question with the equally age old wisdom of "anyone trying to be cool is well on the way to being uncool".

What an elusive thing "cool" is! The minute you grab it it slips away. But ask any kid graduating from college where they want to live and chances are you are going to hear the word "cool" used. Also, there's a good chance "Indianapolis" will not be one of the words they use. We need to change that.

Since cool can't really be manufactured I want to put forward that it can be incubated. You can make sure the soil has the right PH levels.

I think we can accomplish this by having cultural micro-loans, available to anyone with a half decent idea.

Cool is bottom up not top down. Find people, groups, organizations, that are just getting going and gently feed them. Just a little at a time as they find their legs. Think outside of the usual arts orgs or non-profits. These organizations are great but they are slllooooow. Let's fund and realize ideas quickly.

I would urge the city or an individual or some organization to set up this micro-loan system online, I know a company that can help :). Perhaps it could allowing voting on some of the higher dollar ideas. This would be like a very local Kickstarter in a way. Perhaps it could be set up where the full funding is triggered once 25-50% is crowd sourced.

Think about the huge impact this could have on the city! It would create buzz and attract artists, musicians, entrepreneurs and nerds from all around. Think of what the impact could be on our economy- the businesses that would come out of this, the tourists and talent that would flock to our city. Even if 90% of the investments fail to bring a return just a few success would more than justify the investment.

Breaking and Entering

I like routines and that is especially true when it comes to my Web/Internet activities.

I go to the same 10-15 sites/services a day. I have habits around my laptop usage (Gmail, Twitter, Facebook, CNN, etc), my home computer usage (add Weather and learning sites), my iPhone usage (NYT, Facebook, Twitter, Text, etc), my iPad usage, etc. So I almost engage mindlessly at times, without thinking. Sometimes I'll just pull up CNN for no particular reason and then wonder, why did I do that?

I think I'm pretty typical of heavy tech users. Our fingers do the walking to our usual stops. So the challenge is how to break and enter that routine. This applies to Software as a Service businesses, online communities, wiki/info sites, and has relevancy for any Website. One visit is nice but routine, daily use is the real deal.

I think about this in terms of our Content Management System. How do I get my clients to make that a regular stop? How do breaking into their routine?

Increasingly I think the most effective way is to enter via a side door, an existing routine. I'm writing this blog via my Gmail account. I send it as an email to Posterous, then it is automatically posted to my www.jebbanner.com blog. They have found an effective way to enter my routine. Otherwise I doubt I would post half as often as I do. It may only be a couple clicks to get to their system but that seems huge in my mind.

In my comfortable email environment I can type away without worrying whether the post will be accepted when I hit submit or what the formatting rules are. I am more likely to engage when I am comfortable. Consider how to apply that to anything you build. Where are your target users living? How far can you go to break and enter their routine without them leaving their comfort zone? Focus on those solutions over fancy bells and whistles within the app or site itself.

The Death of Email?

Facebook's COO Sheryl Sandberg recently proclaimed that email was dying since only 11% of teens use it on a regular basis.

So is email on the way out? Will texting take over?

I know experts like to look at teen/20s behavior as a harbinger of things to come. It makes sense since these kids are often tech pioneers.

But I think in the case of email Sheryl's got it wrong. Teens aren't using email since they aren't communicating anything long form. Texts are essentially short form emails.

Also, keep in mind that the current crop of teens are getting their first taste of technology via cell phones. As tech creeps younger I think we will see more kids getting online via the family/school computer before getting a phone. This means more may have email accounts before phones. I'm seeing this with my 10 year old and her friends who for the most part do not yet have phones but do use email and IM.

When it comes to long form communication, which is very needed in business and life in general, I don't see anything replacing email. Perhaps more communication may be occurring via Social Media platforms like Facebook but to me it's still just email.

Success Markers

In the past I measured success by how hard I worked, how many hours, how many weekends, consecutive days, how stressed out I was, etc

I felt guilty if I suddenly found myself with time on my hands. What had I done wrong to not be busy!

That instinct still sticks with me but I'm learning to resist it. Now I see that not-busy-guilt as a welcome signal that I'm probably doing something right.

Being busy is addictive. That alone should be reason enough to question busy-ness.

On top of fighting the Busy addiction, evolution taught us to find the safe path and stick to it. We are born with a herd mentality that was once useful fending off lions and rival tribes. Unfortunately evolution is a lagging indicator. It's a very slow learner.

In my attempt to expedite evolution I have begun actively resisting these instincts. I now measure success around quality of engagements not quantity of activities. Committing fully to whatever I'm doing at that time. Moving freely between reflection and conversation, work and play. Sectioning off all the other stuff until its time comes back around.

I'm certainly not batting 1000. I'm still scattered and distracted more than I would like. I was pulled away from this post 3 times before finishing. But I do have an understanding of how to measure success.

I look for success markers around little things: not checking email at night, taking walks during the day, not multi-tasking, delegating, leaving work early, reading, having a focused conversation, finding time to play with my kids, writing blogs like this...

What about money? I also see money as a marker but like evolution it's often a lagging indicator of success. I believe that to some degree money will take care of itself if I can hit my day to day markers.

Not everyone measures success the same, I'm not implying that my definition should be yours. We all have our own markers. The better I get to know my markers the better I can make that measurement. What are your markers?