In a world, where generative AI is eating itself and clogging the pipes that once made the world wide web a magical place, Chris Glass’ recent update of his blogroll is a fresh glass of water, served with a swirly straw and a tiny umbrella. It is a reminder that while we all might visit the same 3-5 destinations on the web every day, there are so many tiny websites out there, maintained by people who still believe in the classic values of the open web.

In his own words:

Bored with this timeline? I made a blogroll because everything that happens comes to Cincinnati 10 years later than anywhere else.* *Mark Twain never said this.

Chris Glass

What a wonderful resource: Blogroll (

The three kinds of leverage that anchor effective strategies

Asides / Strategy

Jason Cohen writing on A Smart Bear about one of the fundamental concepts of strategy, durable, differentiated strengths.

“Leverage” means generating a large effect from a relatively small effort, created by riding tailwinds of natural abilities or hard-won assets, rather than fighting a battle for which you are ill-equipped. […] Leveraging strengths is the only way to do great work. (Not “fixing weaknesses.”) Better yet, leveraging differentiated strengths means you beat the competition. Best is when that differentiation is durable over time.

Without leveraging strengths (rather than spending far more energy shoring up a weakness that still won’t be great), the company will not succeed in creating something great. Without leveraging differentiated strengths, the company will not surpass competitors, will have a hard time winning and keeping customers, and will have an even harder time justifying profit-generating prices. Without leveraging durable, differentiated strengths, the company’s success will be short-lived, differentiation will be temporary, and once again it will be reduced to out-spending on marketing or lowering prices until it is unprofitable.

A winning strategy explains which strengths the company will leverage, how it will side-step rather than “attack” its weaknesses, which strengths can be leveraged for differentiated sales today, and which long-term moats the company is constructing.

The three kinds of leverage that anchor effective strategies

Once you understand that a great idea is not a competitive advantage. It’s a bet that the idea is valuable and you’ll be able to execute better than anyone else. But once an idea is proven competitors will try to copy it. Then it becomes a question of whether the idea is actually tied to a strategic advantage that cannot be copied or compensated for. Then, and only then, you have a durable, differentiated strength.

My favorite quote from the article

How do you beat Bobby Fischer? Play him at anything but chess

Warren Buffet

Everything Must Be Paid for Twice


One financial lesson they should teach in school is that most of the things we buy have to be paid for twice. There’s the first price, usually paid in dollars, just to gain possession of the desired thing, whatever it is: a book, a budgeting app, a unicycle, a bundle of kale. But then, in order to make use of the thing, you must also pay a second price. This is the effort and initiative required to gain its benefits, and it can be much higher than the first price.

[…] But no matter how many cool things you acquire, you don’t gain any more time or energy with which to pay their second prices—to use the gym membership, to read the unabridged classics, to make the ukulele sound good—and so their rewards remain unredeemed.

[…] This scarcity feeling creates one of the major side-effects of our insurmountable second-price debt: we reflexively overindulge in entertainment and other low-second-price pleasures –- phone apps, streaming services, and processed food — even though their rewards are often only marginally better than doing nothing.

Everything Must Be Paid for Twice by David Cain

… and then?


Interesting contemplation about how recent advancements in AI will make us all more productive:

You rush through the writing, the researching, the watching, the listening, you’re done with it, you get it behind you — and what is in front of you? … But in the more immediate future: you’re zipping through all these experiences in order to do what, exactly? Listen to another song at double-speed? Produce a bullet-point outline of another post that AI can finish for you? 

The whole attitude seems to be: Let me get through this thing I don’t especially enjoy so I can do another thing just like it, which I won’t enjoy either

and then? – The Homebound Symphony (

The plateau of meh


Most successful careers contain actually quite a few plateaus once observed up close. Wikipedia entries of famous people fascinate me, because they show that their paths are not as clean as one might remember.

There is a variant of the hero’s journey that is often overlooked, because it is far less dramatic and more mundane. One where the hero does not fight the fierce monster or rises up to the insurmountable challenge. Rather, one where the hero just has to endure a slog, has to dig deep to find motivation, has to live with the fact that between epic challenges and glorious victories there are a lot of days where things just go neither right nor wrong.

Pick a random famous person that you admire and look at their Wikipedia entry. You will find stellar achievements at the top, but once you scroll down, you get to the career plateaus where artists fight petty legal battles with prior management, where uninspired albums and movies are released, and where whole seasons are just meaningless struggle. Wikipedia entry often do not gloss over those periods or artificially dramatizes them like a lot of biographies.

Another example is the stock market: Over a period of 20 years, the ten best days make up for more than half of the stock market. That literally means that despite healthy total returns on 99.9% of the days nothing of substance happens or even worse, massive setbacks happen. Unfortunately, it is impossible to predict those ten days. The only viable strategy is to play the long game and stay invested in the market, endure the losses with the knowledge that you will make up for it in the long run.

The meta-achievement of any career is making it through those plateaus of utter mundaneness, keep honing your skills, putting yourself out there, increasing the luck-surface-area, being ready for the next meaningful step without knowing when and what it will be. Because one thing is true: If you keep trying and learning, the plateau of meh is temporary.

I was reminded by all of this by Jeffrey Zeldman telling the story of his career in the advertising industry and the messiness behind every success:

The ability to keep coming up with more ads was why this Moses-looking dude had a roomful of shiny trophies, and I did not. If I wanted a career like his, I would have to seek deeply in my soul for the strength and willingness not to give up. Career aside, if I wanted to create meaningful work, I would need to develop the patience and willingness to watch people kill my darlings, and come back with newer, fresher, better darlings. […] But keeping a positive attitude when an idea I’ve fallen in love with gets rejected remains the second most important thing I can do on a daily basis as I practice my current craft. […] The well is never dry. We only run out of ideas when we choose to stop doing the work.

Sticking To It – Automattic Design

Photo by Wolfgang Hasselmann on Unsplash

The Internet Isn’t Meant To Be So Small


Nice essay by Kelsey McKinney to remind us that the internet has – despite growth and broad adoption – become too small and limiting in recent years. It’s a call to action for us to break out of our echo chambers and embrace the vastness and potential for growth that the internet can offer.

It is worth remembering that the internet wasn’t supposed to be like this. It wasn’t supposed to be six boring men with too much money creating spaces that no one likes but everyone is forced to use because those men have driven every other form of online existence into the ground. The internet was supposed to have pockets, to have enchanting forests you could stumble into and dark ravines you knew better than to enter. The internet was supposed to be a place of opportunity, not just for profit but for surprise and connection and delight. Instead, like most everything American enterprise has promised held some new dream, it has turned out to be the same old thing—a dream for a few, and something much more confining for everyone else.

Source: The Internet Isn’t Meant To Be So Small | Defector

God Did the World a Favor by Destroying Twitter


By far the best paragraph that I read this week came from Paul Ford:

How will these smaller groups of happier people be monetized? This is a tough question for the billionaires. Happy people, the kind who eat sandwiches together, are boring. They don’t buy much. Their smartphones are six versions behind and have badly cracked screens. They fix bicycles, then they talk about fixing bicycles, then they show their friend, who just came over for no reason, how they fixed their bicycle, and their friend says, “Wow, good job,” and they make tea. That doesn’t seem like enough to build a town square on.

God Did the World a Favor by Destroying Twitter

I’m off going to the library to get a book about bicycle repair.

The OKR Operator’s Manual

OKRs / Tips and Tricks

I’ve recently come across the Operator’s Manual, a post by Ian McAllister. It’s a compilation of tips for communicating data, dates and deliverables. Basically, how to live up to “be bright, be brief, be gone”. 

Taking inspiration from that post, below are some tips that I frequently share when it comes to OKRs. My standard line is “OKRs are deceptively simple, but tricky to get right” or as I just recently heard from Isaac “a minute to learn, a lifetime to master.” Below is an overview of some of the tricky aspects. None of them are rocket science, but each represents a hard-earned lesson:

Introducing OKRs

Articulate the “why” for OKRs: The original sin is starting the conversation with “I think we should do OKRs” without specifying what you want to improve with them. OKRs can help with many things such as increasing transparency, aligning teams on clear goals and targets, surfacing disconnects between teams early, bringing strategy closer to execution, improving focus, … Pick one or two challenges upfront and be clear on how OKRs shall help. Unless you create clarity for what you optimize for, OKRs are easily dismissed as another management fad.

OKRs are not an extra thing: OKRs are set to fail when they are handled separately to the rest of the product management process. Instead, they should be tightly integrated into how teams work and manage their products. Product decisions and feature prioritization should be grounded in their alignment to the Objectives and their ability to move Key Results.

Keep it simple: It can be tempting to design OKRs from the get-go for an entire organization all at once with multiple levels. That becomes overwhelming quickly. It helps to pick one leader and design a single set of 1-2 Objectives with 2-4 Key Results each for their area of responsibility. Think of it as a cheat sheet that they would use for the 1:1s with their boss. Don’t overthink it and avoid the temptation to put too much detail into too many Objectives and Key Results. Start with 1-2 Objectives with 2-4 Key Results and take it from there.

OKRs are not individual performance management: OKRs can be an input for an individual performance review conversation. But they should be one of many inputs. As somebody once told me: “I’m not going to force myself to promote jerks just because they deliver on their OKRs.”

Selecting Key Results

Outcomes over outputs: When defining Key Results, if at all possible, avoid output-Key Results. Outputs are basically tasks that need to get done (Launch feature X, reach milestone Y, revamp marketing website, …). They are tactics to get to an outcome, but they are the outcome itself. Walk the extra mile and identify what the benefit is that you want to achieve with a specific feature or activity (increase in user engagement, more leads, better customer conversions, …) and use that as your Key Result. Techniques like the five whys help. That discussion can become quite esoteric (“Why do we exist? What is our purpose?”), but that is only temporary and typically an indication that the team is on the right track to better and more refined OKRs. Rick wrote a good post about this: Binary: Good for code, bad for OKRs

Fewer but better OKRs: Every single time I’ve introduced OKRs we ended up with more than the recommended 3-4 Key Results. I’ve come to accept this as a necessary rite of passage, because after a few OKR review meetings the team realizes that the conversation always centers around 2-3 Key Results that really matter. Once you come to that realization, go ahead and deprecate the other Key Results. They are typically the ones that turn out to be green/on track while nobody feels good about the overall progress.

Be an OKR pragmatist, not an OKR dogmatist: There are lots of different flavors and nuances with OKR implementations. John Doerr had “output” Key Results in his examples and even within the almighty Google not everything is as clear cut as it looks from the outside. Try to understand the underlying concepts behind OKRs, but also feel free to break the rules when they hurt you. In the same way as database normalization comes with clear drawbacks the further you progress, there is value in not being too dogmatic about OKRs. Know the rules well, so you can break them effectively. (Hat tip to Isaac for the punchy headline)

Don’t start with an OKR tool: When introducing OKRs, the first step is to understand the methodology and create a rhythm around setting, reviewing and scoring OKRs. You can do that with a shared document to set, track and review OKRs in a smaller team or one specific level in the org hierarchy. A tool will distract at the beginning and easily derail the effort. Once you roll OKRs out across multiple teams and organizational hierarchies, a tool can help manage the complexity. But start small and simple first, build the muscle and then move to a tool. I wrote more on that here.

Reviewing progress

Commentary over number: Knowing where a metric stands is important, but understanding what drives that metric and what the implications are is by far more important. I recommend addressing three aspects in the commentary:

  • Data (what): What does the data say, is it going up or down, by how much
  • Insight (so what): What does it mean, is this good or bad, what are the causes for this behavior, what can we learn from this, have we identified new risks to our plan, …
  • Action (now what): What should we do about it, do we need to adjust our plans, …

Once you get to a spot where the commentary is consistently good in OKR reviews, OKRs become this amazing learning tool that accelerates how quickly a team understands its customers and its product.

Embrace the red: Encourage Key Result owners to give a fair and balanced assessment of the status of their KR. Being “red” is not necessarily bad – pretending not to be is. Once a team “embraces the red” OKRs shift from a performance management tool to a learning device that facilitates highly impactful conversations about what teams learn as they build, launch and operate products. I wrote more on that here: Embrace the Red.

No watermelons: Avoid the temptation to declare a Key Result as “on track” when it is actually “at risk”, i.e. the watermelon (“outside green, but when you look inside it’s red”). If it’s at risk, declare it early, which brings us to …

No surprises: Leave it all on the table and make sure that you create maximum transparency when reporting your Key Results. I’ve seen too many rationales that assume a hockey stick growth curve only to be surprised in the last OKR review of the quarter or semester. Hope is a bad strategy. One way to address this issue is to track the confidence level for each Key Result as part of the review conversation: each Key Result starts at 50% by default, i.e. a 50-50 chance to hit the goal. As you progress through a quarter you will learn more and the confidence will move up or down and allows a team to communicate confidence even if a Key Result is backloaded. It creates an embedded feedback loop in case confidence levels swing hard towards in the last weeks of a quarter: What could we have anticipated earlier or better mitigated risk? Christina Wodtke has more on that in her book Radical Focus.

Final Words

Every OKR implementation is different and the above are just a few of the lessons that I learned over the years. I’m sure I’ll be able to add more over time. By the way, most people know Measure What Matters by John Doerr, which is a great intro into OKRs. Once you understand those basics, I highly recommend The OKRs Field Book by Ben Lamorte. Lots of hands-on advice in there on how to get started and what kinds of pitfalls to avoid. 

Big “Thank you” to Isaac for his generous contributions to this post. He’s also been the one who got me back on the OKR bandwagon.

Photo by Ryan Graybill on Unsplash

Embrace the red


One of the biggest success factors for OKRs is culture. A healthy team culture of trust is fertile ground for successful OKR implementations. One of the core principles is to “embrace the red” in OKR reviews.

It’s important to celebrate what teams are doing well. At the same time, learning and growth happens in areas that are blocked or need attention. As teams create new categories, targeting new audiences and inventing new products, there will always be aspects that need to improve, i.e. show up red on the OKR scorecard. The red key results are the opportunity to improve the eventual outcome as soon as possible.

It is easy to slip into a mentality that suggests anything in red is negative – and uncomfortable to address. Focusing on red key results will generate the fastest growth. It opens up the path to improvement, growth and scale.

Once you “embrace the red” OKRs shift from a performance management tool to a learning device that facilitates impactful conversations about what teams learn as they build, launch and operate products.

Image: Engine start button on Unsplash