Traverse Trepidation

If you wait for trepidation to fade, you won’t ship

You are going to feel some trepidation.

There is no perfect project.

No perfect work environment.

No elixir keeps you free from fear.

As a leader, you have to get comfortable with dancing with that gut feeling that “nothing is going to work.” Trepidation comes whenever we do something, and it hurts because it might not work.

Something eventually does.

Then another thing, and another thing.

You have to show up, traverse trepidation and get to ship.

No one can count on your fear. We can, however, rely on your projects.

Get to work. 

Client Discussion Framework

You don’t ever want someone to find out something

Surprises happen.

However, professionals find ways to minimize the surprise on their end.  The easiest way to do that is to communicate early and often.

When I take on projects, I use this framework to keep clients, customers and bosses engaged and aware.

How to use this

Go through it step by step. Each step requires some sort of communication. Don’t move on to the next step until you’ve answered each question you see. Use that as your tripwire.


You keep your client in the loop with these 6 steps of the process.


What has to happen to make this project succeed

  • Who is this for?
  • What does success look like?
  • At what point do we stop/quit?
  • Is there any ways for these requirements to change?


So now that we know what the requirements are, what can we do to make things “pop”

  • What is the worldview of our customer?
  • What is the context for this project?
  • Do constraints exist? Should we add them?
  • How do we “wow” knowing our constraints?


How are we going to execute the plan now that we have now.

  • Is there a particular framework we use to get this done?
  • What is the team?
  • Who helps us get this done?
  • What is our check-in schedule? What do we need there?


This is the work, where we test things and see

  • What is our minimum viable product?
  • Do we have a test group of customers/stakeholders that we can show this to?


Lets see if this is what we want

  • Do we have the green light from stakeholders to put out the finish product
  • What changes would you like to see?
  • How much time do we have?What isn’t possible?


Now that its finalized, time to ship

  • When can we do a post-mortem?

This isn’t a perfect model, sometimes these questions spring more questions. That’s a good thing, the more you know, the less people have to find out.

And the last thing you want, is people finding out.

Happy projects everyone!

“All models are wrong, some are useful.” – George Box

Life isn’t built on models, it’s more complex than that

Models are necessary. They help us ship work and translate our taste.

It is important to recognize, however, that by using a model, we are making something fit.

Any time you find yourself making things fit, you are missing a piece of the story.

It’s an abstraction. Mostly, you are pulling your camera(perspective) out, and as such, a bit of the picture becomes blurred to you.

That piece still exists.  You just stop seeing it.

Remember, the map is not the territory.


Do the Work, Whatever it Takes To Turn it In

Sometimes, the ends do justify the means. Get to work

I have apps like freedom on my phone that block out the entire internet because I know I don’t have the self-control just to sit and type.  Sometimes it’s hard for me to work.

The work I turn out because of that app doesn’t have a mark on it.  I didn’t earn any points for trying to avoid Facebook.

I don’t care if you

  • You have to squeal
  • Listen to comedy albums out loud
  • Take an afternoon nap

You do whatever it takes to get the work done.

Disorder is Here. Get Used to It.

Disorder is here to stay, in fact, it never left

Human beings are complex creatures.

With complexity comes disorder.

We like “simple.”  Things that are the way they are “supposed to be” never are that for too long.

And to tell the truth, they weren’t that for an extended period (relatively) anyway.

  • The idea of a “job” as we know it is only 200 years old
  • Car culture is only 75 years old
  • Venture Capital as we know it has only been around for 40 years

The last two items on that list mean there is someone in your family that is still alive who didn’t have a car growing up, or thinks it’s crazy to raise money without going to the bank.

Humanity is always changing.

Don’t get left, because later, there will be jet packs :-).

Get Simple

Simple is great. It isn’t easy.

Going from complex to simple takes a lot of work.

It requires taste and understanding.

For example:

Turning your phone from 10 buttons to 3 is a lot of work, and for it to work seamlessly, you have to master the context of usage.

  • How does someone use the phone.
  • What exactly would we miss?
  • How do we plan for it?

Answering those questions makes the user feel like he or she won’t miss anything, and that is basically the Holy Grail in client service. People love simplicity so, early and often, they push for it.

That’s why it’s important to look out for false simplicity. People go out of their way to look simple because it makes them look good. As a result, things get lost.

The quickest way to see “false simplicity” for what it is to ask follow-up questions.

If they don’t have an answer, they haven’t thought about it; someone will.

Stop Playing the “God Game”

We aren’t capable of playing the “God Game” well.

What is the “God Game?”

The “God Game” is when you try to control every outcome, have every contingency, and command every action.

Two problems with the game

  1. When you believe you know everything, you are blind to the unknown. This tactic can be catastrophic (i.e., Hillary Clinton’s campaign for President, “Stay” for Brexit).
  2. Working with humans is like a garden, leading them is the necessary fertilizer and water. We can’t command a flower to grow the way we want; we can only feed, water, and cultivate it. Playing the God Game makes us control others’ growth and development.

Playing the God Game blinds us and burns us out.

Let your people grow.

What Does it Look Like Around Here?

What is the worldview?

If I went to your office and asked about the biggest fears around there, what answers would I get?

Would it be the same answers you would get?

How about these questions:

  • What does success look like to you?
  • What project is exciting you now?
  • How do you feel now compared to six months ago?
  • What is your toughest problem, and how can I help?
  • What is something I’ve done in the last few weeks that has made your life easier?

These are questions that give you an idea of someone’s worldview. If you are looking to lead, set tone, and create, it’s a great place to start.

Note – you don’t need to be someone’s boss to ask these. Let’s get this out the way: boss does not equal leadership 🙂

On Leadership – Taking the Point – December 2016

Leadership is service

When I was younger, I didn’t see that at all.

In my head, it was either:

  • The leader was the boss and, as the boss, everyone had to listen to what the boss said.
  • People had no one to lead them other than themselves. Think of the characters Clint Eastwood played in westerns: he did it his way, and people could follow if they wanted.

Both those things are fantasies, and when I found myself in a position to lead a team or a group, I did it from one of those binary positions. The results were often disastrous.

After a few blow ups from people thinking I demanded too much or didn’t care, I realized that my models weren’t good.

After spending some time working on fixing the models, I went to work taking some leadership positions. I got my hands dirty. I learned a lot.

The most important lesson was that leadership is a journey. It doesn’t stop.

The second most important thing is that I got better when I told people where I was to help speed up their leadership journeys. It gave me time again to adjust those models.

That’s why leadership is the theme this month.

This month’s theme ties into a “big idea”

At the end of last year, I wrote a post that resulted in my picking four themes for 2016. They are the guiding light (strategic)  for my ideas. Each month on this blog, I break things down into the practical (tactical). This year I want to tie them together, so each month, I have to write the reason they connect.

Reread candidate

Turn the Ship Around!: A True Story of Turning Followers into Leaders  by L. David Marquet– I couldn’t put this book down and after reading it gave it a place on my great book shelf. Marquet does a great job here simply explaining his process of leadership and giving life examples on how it worked. I can think of no better manual to hand to someone who wants to lead.

Note: This month’s theme is going to be shorter than usual. Instead of all month, I am going to spend the last few days wrapping up the year with some end of the year lessons. These will be longer posts, so be ready! It will end the same way.

Taste is the Key to a New World – Lessons From November 2016

A New World Exists Based on Taste

It comes through the work.

Good taste is hard to find because it’s hard to cultivate.

There is no way for you to get to where you are going without putting yourself out there, without being vulnerable and doing the work.

The biggest lesson for me unpacking this theme was how much all of it went back to doing the work. If you look at any master, they have their dojo, and they set up performances. You can talk all you want; remember that there is no substitute for being there.

It also isn’t free. You have to give to get. Some of the pain comes from showing your work, but if you don’t, you end up with more of a headache.

Your brain adjusts to seeing things with “taste” that you can’t see without doing the work.When it comes to paintings, artists see things that laypeople can’t see. Musicians hear music differently. Your superpower grows with you. It is unique to you –  There is no one “real” taste. We are all different.

The payoff, though, is tremendous. Ship.

Growing taste opens up a whole new world.

Books – My Goodreads Account

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