Meetings with executives – making them useful and messing things up

How to make meetings with executives most useful:

i) For projects in early stages, use the time to align on the problem statement/goal and ask any related tough clarification questions

ii) For projects in execution, create simple docs/slides that share progress toward ETAs and bring forth all the hairiest disagreements and decisions the working team is facing (without throwing peers/partner teams under the bus).

How to mess things up: 

i) Not demonstrating urgency/speed

ii) Covering up misalignment within the working team

iii) Attempting to impress the room with beautiful presentations vs. prioritizing discussions on hard questions and outcomes (any celebration of progress happens best when it ensues vs. when it is being pursued)

The Three Sides of Risk

I interviewed Morgan Housel a few years back as part of a side project where 2 friends and I interviewed folks we thought were inspiring and/or thought provoking.

Morgan had written a few wonderful articles about investing on The Motley Fool and I reached out after one resonated deeply. Many years later, he’s still writing as part of his fund – “The Collaborative Fund.” And, I’ve shared a few of his posts over the past year or so.

Today’s post – The Three Sides of Risk – is an example of why I’m a fan of his writing. He shares a poignant story from his time as a ski racer growing up on the slopes of Lake Tahoe. He joined two of his friends to ski in forbidden terrain at one of the largest resorts in Lake Tahoe. After one run where they experienced a mini-avalanche, he decided to call it a day.

His friends, however, decided to one more run.

Sadly, that run proved fatal. And, below are his notes at the end of the story.


I’ve been risk-averse in other areas of life ever since, too. I drive the speed limit. I obey the seatbelt sign on airplanes. I invest in index funds.

I don’t know if Brendan and Bryan’s death actually affected how I invest. But it opened my eyes to the idea that there are three distinct sides of risk:

  • The odds you will get hit.
  • The average consequences of getting hit.
  • The tail-end consequences of getting hit.

The first two are easy to grasp. It’s the third that’s hardest to learn, and can often only be learned through experience.

We knew we were taking risks when we skied. We knew that going out of bounds was wrong, and that we might get caught. But at 17 years old we figured the consequences of “risk” meant our coaches might yell at us. Maybe we’d get our season pass revoked for the year.

Never, not once, did we think we’d pay the ultimate price.

But once you go through something like that, you realize that the tail-end consequences – the low-probability, high-impact events – are all that matter.

In investing, the average consequences of risk make up most of the daily news headlines. But the tail-end consequences of risk – like pandemics, and depressions – are what make the pages of history books. They’re all that matter. They’re all you should focus on. We spent the last decade debating whether economic risk meant the Federal Reserve set interest rates at 0.25% or 0.5%. Then 36 million people lost their jobs in two months because of a virus. It’s absurd.

Tail-end events are all that matter.

Once you experience it, you’ll never think otherwise.


It is a powerful post. If you have a few minutes, I’d suggest reading it in full.

Speed of execution

Speed of execution is a powerful capability to have in our arsenal.

The underappreciated aspect of moving fast is that a significant part of our ability to do this plays out in our own minds. And, to that end, there are three super powers that help us make speed our ally –

1. A relentless focus on forward motion/progress (at the expense of any illusion of perfection) on things we control

2. Obsessing about the work without worrying about how the credit will be distributed

3. Being incredibly hard to offend

Sometimes, even small margins in speed of execution can have massive downstream impact on our products, businesses, and careers. And, each of these superpowers helps with those margins.

Of course, if we’re able to operate with a combination of these, the results tend to be formidable.

Showing up as we really are

“I can’t think of a sadder way to die than with the knowledge that I never showed up in this world as who I really am. I can’t think of a more graced way to die than with the knowledge that I showed up here as my true self, the best I knew how, able to engage life freely and lovingly because I had become fierce with reality.” | Parker Palmer

As we run the various races that are part of our day-to-day, it is easy to forget that the objective isn’t to be the first.

It is to be the only.

Nailing it and trying hard

We’ve been attempting to teach our kids to ride scooters/bikes recently. While there are a few experiments in progress (read: reflections to follow once we have experiment results), there was an interesting recent ritual where we’d come back home after a walk/ride and our older kid would ask – “Did I nail it today?”

I answered “yes!” unconsciously for a few days before realizing that the question and my response was making me feel uneasy.

I realized that she’d picked it up from my unconscious reaction on one of the days. And, she figured this was a great way to get some validation for the progress she made.

Once I came to this realization, I began switching my response to – “Did you try hard today?” And, if the answer is yes, then that’s great because it is the effort that counts.

A few days in, this re-framing is slowly beginning to become the default question/self talk.

Long may that continue.

Boom de ya da

In 2008, the Discovery channel released a wonderful 1 minute ad titled “The World is Just Awesome” with an incredibly catchy line – “Boom de ya da, Boom de ya da.” I think I shared the video on this blog when I first saw it.

Years later, we’ve been revisiting the song a bunch as we found a version that the kids have taken to and that we sing as part of their bedtime routine.

As we’ve been isolating in response to COVID-19, we’ve taken many walks around the park near our place and spent a lot more time appreciating the dandelions and trees. So, the timing of the rediscovery of this song couldn’t have been better.

We have been fortunate to inherit such a wonderful planet. It is truly awesome.

And, it is on us to do our part to ensure it stays awesome for the generations to follow.