My Favorite Management Hack of 2020

2020 was a rough year for everyone, even for those of us blessed to be able to work from home. Psychologically and emotionally, it’s easy to feel disconnected and lonely when you don’t see people outside your household for weeks and months on end. And this presents some unique challenges for maintaining culture and productivity, and keeping morale up in general.

The Challenge

When the pandemic hit in March and everyone in the world started working remotely, we were worried about how to keep people connected and plugged in. We had to adapt quickly to keep communication flowing and make sure that everyone felt connected and a part of the community that we somewhat lost when everyone stopped going into the office.

We developed a solution that has worked really well for us, and I’d like to share it. I hope you find it useful, but I’d love to hear if you’ve found other things that work as well.

The Solution: Monday Morning

Immediately after switching to full remote work, we switched up the cadence of company meetings. We went from an all hands once a month to two in the same week.

Every Monday morning at 9:30 we get everyone together (via Zoom) to kick off the week with a company-wide coffee hour.

Mmm, a cup of coffee together is a great way to kick off the week!

In this meeting we go team-by-team over what we accomplished last week and our goals are for this week. And we check on what we actually got done last week compared to what we were planning to do:

An example team dashboard

This is just a simple Google sheets deck that we have all of the leaders of the company update on Friday afternoon, with one slide per team:

This is the whole thing

The whole meeting takes about 30 minutes, and it’s a great way to kick off the week. Everyone knows what’s happening around the company, including in all of the other teams. Everyone seems to like it, and there are some interesting byproducts:

  • Our short-term goal setting has gotten much better. Goals are set on a weekly basis, which has resulted in more accountability and velocity. Teams are looking at goals on a shorter time horizon now, which leads to more tangible outcomes every week.
  • Wins and losses come at the end of each and every week, which is very motivating if the team hits their goals, or if the team doesn’t hit their goals. Either way, the entire company sees it.
  • We’ve become much better at estimating how long it will take to do something. If you’re bad at estimating it can completely destroy morale and trust, this shorter-term focus has made the act of slicing up work into achievable chunks much more efficient.

The Solution: Friday Afternoon

On Friday afternoon there are two more things we do every single week.

At 1pm, after the leadership team updates the Monday morning deck, we meet as a group to review everyone’s updates together, ask questions, and talk about challenges. Some of the best discussions and collaboration happen during this meeting, and this is the main place and time where cross-team dependencies are often discovered and planned around. We also talk about wins, challenges, and collect shout-outs for people who have done outstanding work over the past week.

Then at 4:30pm, before everyone takes off for the weekend, we wrap up the week with our Friday Afternoon Happy Hour:

Not everyone drinks at happy hour, but we do keep it happy!

We try to keep happy hour fun and lighthearted. We celebrate wins, give shout-outs to people who did something extraordinary over the course of the week, and show the company any fun or funny things that happened during the course of the week. We try to leave some room for people to talk and have fun as well (we’ve had some GREAT Zoom backgrounds!), but generally we try to send people into the weekend on a high note.


These meetings have become routine for us now, and pretty much our entire company loves them. Our communication is better, teamwork is tighter, goal-setting is more accurate, and velocity is way higher.

Honestly I would have a hard time *not* having these meetings now. They’ve worked *so well* to create a tighter company all around that I don’t know that any set of in-person meetings could really replicate, let alone surpass, the results.

This may not work for everyone, but it works great for us, and I hope that at the very least this sparks some ideas for making your company more efficient and maintaining your culture during this–or any future–challenge to working together.


Dais and the Internet of Insurance have brought me into the insurance world, and I love it.


I am proud of my role as the founding CTO of Uptake, a data science company for heavy industrial machinery. We led the company from 2 employees to Forbe’s Hottest Startup of the Year and over 400 employees.


Data Companies Eat Software Companies

I was in the car this morning listening to a BBC report that, for the first time in a long time, the mortality rate in the US went up instead of down. The average life expectancy actually got shorter this year. That’s scary, but it got me thinking about software and a trend that I’ve noticed. A trend that is going to separate the winners from the losers over the next five years.

There’s a clear line developing between the future haves and have-nots in the digital world. A line of thinking around where the value lies and what you can and cannot make money on.

Traditional software companies have focused almost exclusively on building software and charging for it. This is outdated thinking and looks to me a lot like painting a giant target on your forehead. Using this model today is like charting your course by looking in the rearview mirror. Meanwhile you don’t realize that you’re going off the road.

If you look at what the most forward-thinking companies are doing you can start to see glimpses of where the world is heading. Here’s a hint: they’re all giving their software away. Why? Because software doesn’t matter.

Have you been watching as tech giants who understand where things are going give away all of their best technology? Look at Google, who isn’t locking its AI technology, Tensorflow, away in a deep, dark vault — instead it’s giving it away. Same with Facebook, who gave away its React technology and looks to be headed in the same direction with its own AI stack, FBLearner.

Why? Because on a long enough timeline all technology becomes commoditized, and they know it.

The reality is that all of the supposedly “hard tech” is becoming more accessible by the day. Most if not all predictive algorithms are out there for anyone to use. Scalable architecture is getting easier to build every day. There’s really nothing you can’t do with open source technology now, the barriers to entry are dropping constantly. Some of the technology that’s out there right now for free just blows my mind. Tools like OpenAI Gym would have been sold for megabucks just two years ago. They’re free now.

So what does matter then? Where’s the real action?

Control over the data. That’s what matters. You can replace technology, you can’t replace data you don’t have.

The kingdoms of tomorrow will be built on an empire of data, and the land rush is happening in plain sight, right now, if you know where to look.

Most companies won’t come out and say that data is the most important thing, but actions speak louder than words. When IBM acquired and Merge Healthcare for multiple billions of dollars, many people were puzzled. There’s no obvious synergy there, the acquisitions happened because the value was in the data.

The most interesting companies today are working hard on giving away software that other companies charge tons of money for. Why? In order to get access to the data.

I agree that software is eating the world. But in the technology food chain, data eats software.

The really interesting dynamic here is that all of the software-driven startups are effectively creating a hit-list of areas where free technology can come in and take them out at the knees, undercutting them in order to get the data. I suspect we’ll see quite a bit of disruption to the status quo in the coming years, there are lots of companies out there who aren’t thinking about this correctly.