In 2018 Decide to Work Deliberately

“I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.” – Henry David Thoreau

You may have heard this quote before. Maybe it resonated with you, or maybe not. What does it mean to live (and work) deliberately?

I’ve thought a lot about this over the last few years.

Earlier in my career, I certainly wasn’t deliberate. I “went with my gut” a lot. Some of it was my lack of experience. Some of it was an overinflated ego.

As I got more experience, I looked back at earlier decisions that I had made as a leader and realized how poorly considered some of them were. With just a bit more thought, I could have set myself and my team into a much better position. I’ve also been lucky enough to work with people who have modeled what approaching work thoughtfully can look like.

Consider all the decisions you make in a day at your job. You work on this project instead of that one. You choose the opening phrase you make in your pitch to a customer. You attend this training or decide to skip it. You invite one colleague to lunch and not another. You hire this person instead of that one. How much thought do you put into each of these decisions? Do you know why you made this choice? Do you ever go back and evaluate what worked out well or poorly and what you might do differently the next time?

Some of these decisions might seem obvious in the moment. Next time you encounter a decision that seems trivial, take a beat and just think about why the choice is so clear. Every choice you make means that you are also choosing not to do something. Have you considered both options? Every decision is the start of a chain of events. What are the assumptions you are making about the effects of this choice? Later, come back to your decision and test if your assumptions were correct. Was it still the best option? What did you learn from this that you will bring forward?

Thinking through your assumptions, and the implications of a decision, and evaluating the outcome is thinking strategically. Being strategic is critical for big company decisions, but is also valuable in the decisions you make all day.

It does take a bit of practice to do this, but as with anything you practice, it gets easier and easier. It will eventually become second nature.

So, next time you make a hiring decision or decide to work on project X tomorrow so you can do project Y today, ask yourself “Why is this the right thing to do?” If you can’t answer immediately, spend a minute and consider. You may find yourself realizing that it isn’t the right choice, and the next time you may spend a bit more time in making that decision.

“Look at every path closely and deliberately, then ask ourselves this crucial question: Does this path have a heart? If it does, then the path is good. If it doesn’t, it is of no use.” – Carlos Castaneda


[Thanks to Diane Guerts for editing help]

Building a Management Training Curriculum at Avvo

[This is a repost of]

This week, we kicked off manager training for Avvo technology managers. Before we could build a curriculum, we needed to decide what was important to learn and where we as a group needed the most development.

If I had done this with my organization at Adobe, years ago, I might have made a list of capabilities or requirements for our roles and then assessed each person against those requirements. I’ve since learned that the top-down approach tends to isolate and alienate people. It is something done TO them. They don’t feel investment or ownership of the process. If they disagree with the list or my assessment of them, it is hard to challenge due to the nature of the process.

When I was at Spotify, I worked with Paolo Brolin Echeverria and Mats Oldin to build manager training for my Tribe. They developed an excellent kick-off exercise that I repurposed for my team at Avvo.

The process is straightforward.

We began by individually thinking about the qualities of a good leader in our organization. We each wrote every important quality we could think of onto individual post-its. This effort took about 20 minutes. Then, one by one, we put each of our post-its onto a large board. As we placed each quality, we explained why we believed it was important for a leader at Avvo.

Kyle getting us started
Kyle getting us started

When we finished putting all of our post-its on the board, we affinity-grouped them. Affinity-grouping resulted in 30 groups of similar qualities as well as a few individual post-its that did not fit into any group. The grouping process required a lot more discussion so that we could all agree on the final groupings.

Nic, Ian and Jordan working on cleaning up the affinity groups
Nic, Ian and Jordan working on cleaning up the affinity groups

At this point, we had collectively described 30 essential qualities of a leader at Avvo, which is far too many to effectively focus on. To narrow things down, we each received six votes to put towards any group of qualities that we felt were the most critical. Then, we tallied the votes and took the top eight as our core qualities of a manager at Avvo.

The voting process also led to a lot of valuable discussions as we saw where we had voted as a group. Were these right eight? Were they the most important eight? The eight qualities that we picked were: empathy, develops autonomy, builds good teams, is real and trustworthy, is a big picture thinker, supports mastery, gives feedback, and has a bias for action.

Dot voting in progress
Dot voting in progress

Individually, we then assessed ourselves against the eight core qualities on a three-point scale: “I need training on this,” “need training, but it can wait,” and “I can train others on this.” One by one, we went up to a board that had the eight qualities mapped on a spider graph. We put dots on a line for each quality where we rated ourselves. We explained why we chose that assessment. This led to further good discussion about how to assess ourselves against these qualities.

Our collective spider graph
Our collective spider graph

The group as a whole found this exercise to be very valuable. We had excellent discussions on what it means to be a good leader at our company, including the values we agree on, and the ones that we don’t. We were also able to prioritize those collectively in a way that everyone feels ownership and allegiance to them.

And we came to an understanding of where we need to develop the most as a group. This mutual understanding will inform the curriculum for our management training – my original goal.

A diversity challenge: tech start-ups have a great opportunity

For decades we’ve been complaining about the lack of diversity in the technology industry. We’ve worked on the pipeline problem. We’ve worked on reducing bias. We’ve worked on the sourcing problem. We’ve worked on the retention problem. The net result thus far is that we’ve barely moved the needle.

Most of the companies that are investing in diversity programs are the larger companies. For them, their continuing lack of diversity is a public embarrassment.

At scale though, it is a far greater challenge for a company like Google, Microsoft, or Facebook to get to any percentage of tech workforce that mirrors their customer base. The numbers are too large to move the needle. It’s far easier for startups.

A critical part of building an inclusive culture that supports diversity is reducing the “otherness.” Inclusiveness is also much harder to do in a large company. If Google hired 1000 developers of color across all their offices, those individuals might never encounter another person like themselves on a daily or weekly basis. They may still be the only person of color that their peers see at work. They will be spread too thinly across the population.

Large technology companies should still work consistently to improve their diversity, but startups are much better suited to solve the diversity problem for the industry as a whole.

A startup with a development team of ten, four of them being women, has a ratio of 40% female developers. Any woman who interviews with the company will see that they are welcome. Any man that interviews will understand that they would be joining a company that takes diversity seriously and will be expected to conduct themselves appropriately. This would be the same for any other underrepresented group. If the company is serious about building a diverse workforce, they will find it easier to continue to be diverse as they grow.

Bringing in a diverse workforce at the early stages of a company will also mean leadership opportunities for those employees as the company grows. It will help address the lack of diversity in industry leadership, which further helps build minority representation. It will also eventually mean more startups started by underrepresented industry groups, which will continue to fuel diversity in the industry. Some of these startups may be acquired, putting their leadership into the leadership of other companies and increasing diversity in those companies as well.

According to most surveys, startup founders’ biggest challenge is hiring development talent. Meanwhile, there are ever-larger numbers of coding schools and boot camps graduating eager junior developers, willing to work hard, and coming from largely underrepresented populations in the industry. There are also many experienced minority developers at the larger companies who would be interested in being in an environment that lets them feel free to be themselves.

Unfortunately, most startups neglect the critical cultural aspects of building their company as they chase product/market fit, funding or customers. What many of them haven’t considered is that building a diverse company will help them find the right product for mainstream audiences, that sources of capital are increasingly valuing diversity in their funding decisions, and that diverse teams build better products that attract more customers.

So, I call on my fellow startup CTOs and CEOs to take on this challenge. If we succeed, we will not only build a better industry; we will also create better companies for our shareholders, our employees, and ourselves.

Talks: 1st half 2017

I’ve been remiss in posting since I’ve been back in Seattle. Readjusting to life in the states, and adjusting to the new role has kept me busy. I hope to rectify that in the future. I have been lucky enough to be invited to speak several times this winter and spring in the US and Europe. If you’ll be there or live nearby and want to meet up, drop me a line on twitter and let me know!

Articles I’ve liked recently (stuff I’ve been reading lately #3)

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How Spotify Builds Products – my slides from May 2016 talks

These are my slides from the talks I gave at infoShare in GDansk and to and Think Money in Manchester. The talk in Poland was a shortened version of this content. This is a sort of mega-mix of many of my previous talks. This talk ends up presenting a bit more of a coherent picture on how Spotify’s culture and organization go hand-in-hand with it’s data-driven product development.

As with most of my talks, the majority of the content was in the spoken parts instead of the slides. I will hopefully have a video to share soon from one of these talks…