Article: Estimation Games

My colleague Corina sent me a great article last week about the games that are played during the process of estimating IT project workload:

The apparent inability of IT people to accurately estimate the effort, time and cost of IT projects has remained an insolvable problem. In interview after interview with business people, our group has found that poor estimation is one of the major factors in the breakdown of relationships between IT people and their clients.

The article reminded me of the famous Programmer Time Translation Table. What's interesting is that the article focuses on the interpersonal aspect of the estimation process:

Almost all research into improving software estimation miss a vital point: it is people who estimate, not machines.
This simple point underpins the real problem in estimation. In fact, our research has shown that within certain conditions, IT people are pretty good at estimating. Further, our research has shown that the major precondition for improving estimation accuracy is the existence of an estimation environment free of inter-personal politics and political games.

Their take is similar to Daniel Kahneman's Thinking, Fast and Slow recommendation that the first thing to do if we are to fight our cognitive biases is to learn to recognize them. In other words, if you can't identify it, you can't fight it.

The article goes on to describe several of the games that are played as part of the estimation process:

It is our belief that over the 30 plus years of commercial computing has developed a series of sophisticated political games that have become a replacement for estimation as a formal process. More importantly, like all good games they are passed on from generation to generation by "children" IT people learning from "adult" managers who of course learnt the games from their adults when they were children and so on.

If you have ever been impacted by this problem (and if you work in IT, you have!), read on!

A few thought on sales from David Cummings

We had a new sales intern starting about 10 days ago. This was the occasion to dive into some relevant advice from David Cummings I read a while back.

The first 30 days for a new sales rep is all about shadowing existing team members as well as training with the sales manager. Then, by the end of the month, it’s time for live calling and prospecting. Training is a critical part of the sales rep on-boarding process.

The sales team should be working towards a reproducible, and profitable, sales process. As part of that iteration, a sales playbook should be at the top of the sales manager or entrepreneurs list of items. A sales playbook is the how-to manual for a sales rep.

Last but not least, interesting advice about connecting the Product to the Wallet:
Last week I was talking with an entrepreneur about their new product focus. After digging in, he volunteered something that really stuck with me: their new direction connects the product with the wallet in a way it never was before. Similar to the idea of candy, pain-killers, or vitamins, products that can clearly demonstrate an increase in revenue for the customer are more desirable.
With a good ROI demonstrator, pretty much every product should be able to do this. It is one of the keys of a successful sales process.

What's a blog good for, anyway?

Literally billions more people now have a much simpler way to express themselves online thanks to the ease-of-use that is characteristic of any service that seeks to focus on one particularly aspect of communication, a big contrast to a blog’s ability to do anything and everything relatively poorly. It’s fair to ask just what a blog is good for anyway.
This sentence from Ben Thompson's latest Stratechery article rang true on my side. I started blogging back at the end of 2006, over at Blogger. I blogged there for a while, then switched to Posterous for the ease of use of its email-to-post feature. When Posterours was shut down by Twitter, I moved over to Posthaven, where this blog still lives.

Over the course of those years, I tried a lot of other publication services. Facebook, of course. TwitterQuoraMedium. Each of them offers a specific set of features that makes them for specific use cases. Facebook makes it easy to stay in touch with your friends. Twitter is instantaneous. Quora gives you reach over a specific audience. Medium offers amazing publishing tools.

Yet I find myself coming back to this blog. It's the only place where I can control my identity on the web. I am this blog, and this blog is me. It's the only place where I can control exactly how what I have to say is presented. The domain name is mine. I pay for the service so that I can avoid ads. As it turns out, I'm not the only one feeling this way:
And there, in that definition, is the reason why, despite the great unbundling, the blog has not and will not die: it is the only communications tool, in contrast to every other social service, that is owned by the author; to say someone follows a blog is to say someone follows a person.
And that's definitely something no other service will give you.

Catching up on 2014!

Long time no posts... Let's blog back to life in 2015 with a selection of posts from 2014 I found interesting but never got to posting:

Management Clichés That Work by Steven Sinofsky

The following 15 clichés might prove helpful and worth making sure you’re really doing the things in product development that need to get done on a daily basis. Some of these are my own wording of other’s thoughts expressed differently. There’s definitely a personal story behind each of these...

Plenty of them are must-follow lessons.
It was 10 years ago and I was CEO at my previous company. I had been called out by an employee on one of our core values of only hiring "passionate" people. I fumbled my way through an excuse, but they were right. We had done a great job with a purpose and vision, but the values were vague, trite, and ultimately useless in decision-making or inspiring people. It was like asking the contractor working on your house to "make it more interesting."...
Easy to say, harder to do!

Policing by consent by Jason Kottke

In light of the ongoing policing situation in Ferguson, Missouri in the wake of the shooting of an unarmed man by a police officer and how the response to the community protests is highlighting the militarization of US police departments since 9/11, it's instructive to look at one of the first and most successful attempts at the formation of a professional police force...
Interesting re-read after the recent events in France.


The basic gist is that in situations where costs come before revenue (like, say, a sales force for selling to enterprise), chasing growth over making money increases the amount of long-term profitability. Seriously, read the whole thing.

Suster’s article was not about Box specifically; for that I refer you to Dave Kellogg’s piece, Burn Baby Burn: A Look at the Box S-1. He concludes that the Box numbers are very reasonable and that the business is scaling well...

Interesting re-read in the wake f the Box IPO.

Most of you have never heard of Energy Future Holdings. Consider yourselves lucky; I certainly wish I hadn’t. The company was formed in 2007 to effect a giant leveraged buyout of electric utility assets in Texas. The equity owners put up $8 billion and borrowed a massive amount in addition. About $2 billion of the debt was purchased by Berkshire, pursuant to a decision I made without consulting with Charlie. That was a big mistake.

Unless natural gas prices soar, EFH will almost certainly file for bankruptcy in 2014. Last year, we sold our holdings for $259 million. While owning the bonds, we received $837 million in cash interest. Overall, therefore, we suffered a pre-tax loss of $873 million. Next time I’ll call Charlie. 

A must-read. Waiting for the 2014 letter!

Article: Spend Time Educating the Team on How the Business Works

Good advice from David Cummings:

One area that’s under appreciated by many entrepreneurs is the value of educating team members on how different aspects of the business [...]. There’s value in taking time to make sure everyone has at least a cursory understanding of different departments and key drivers of the business model. [...]

People inherently want to grow and learn as part of their own journey, and providing a more broad-based education in a startup helps. Spend time educating the team and the team will return the favor with more ideas and innovation.

I've seen this in action several times: when behavior from the sales team is perceived as being wrong and/or stupid by the client project team, a short explanation of its rationale usually goes a long way into alleviating concerns.

Article: Why I Just Asked My Students To Put Their Laptops Away

Clay Shirky at his best (as usual):

Regarding teaching as a shared struggle changes the nature of the classroom. It’s not me demanding that they focus — its me and them working together to help defend their precious focus against outside distractions. I have a classroom full of riders and elephants, but I’m trying to teach the riders.

He goes on with remarks that are more widely applicable (internal company meetings anyone?):

The structure of a classroom, and especially a seminar room, exhibits the same tension. All present have an incentive for the class to be as engaging as possible; even though engagement often means waiting to speak while listening to other people wrestle with half-formed thoughts, that’s the process by which people get good at managing the clash of ideas. Against that long-term value, however, each member has an incentive to opt out, even if only momentarily. The smallest loss of focus can snowball, the impulse to check WeChat quickly and then put the phone away leading to just one message that needs a reply right now, and then, wait, what happened last night??? (To the people who say “Students have always passed notes in class”, I reply that old-model notes didn’t contain video and couldn’t arrive from anywhere in the world at 10 megabits a second.)

Based on personal experience, I don't really understand why teachers allowed us to use our laptops during class. The amount of students using them to do anything but listening to the class was just overwhelming, especially once wireless connexions became widely available.

Article: Shipping is a Feature

Steven Sinofsky published this back in April:

I chose to focus on what I think is the most challenging aspect of being a PM, which is achieving clarity and maintaining a point of view for a product when all forces work against this very thing. What customers value most in a product is that “it just work” or “does what it is supposed to do,” and yet at every step in a product, the dynamics of design work to make this the most difficult to achieve.

He goes on to list 5 lessons life taught him about product management. Two of them really resonated with me:

Shipping is a feature. Every PM knows this but it is also the hardest thing to get right. As a PM you throw around things like “the enemy of the good is the perfect” or, well, “shipping is a feature” all the time, yet we all have a hard time getting a product out the door. There’s always more to do to get it right.

This one sounds so obvious that it feels almost useless to say. Yet I've seen more than once great features get pushed further down the timeline again and again because it just wasn't ready yet. Humans are prone to the planning fallacy: underestimating how long it will take to get things done. Working against it is a full-time job!

You get paid to decide. Some people love making decisions on their own. Other people need socialization and iteration to make a choice. Either way can work (or not) as a product manager, but to be great you really do have to decide. Deciding anything important or meaningful at all means some people will disagree. Some might really disagree a huge amount. The bottom line is a decision has to be made.

This last one is especially difficult in the context of building a truly open source product, where every committer has an equal voice in the outcome of the product. Sometimes two visions are just not going to align exactly and a choice has to be made. Having a final decider helps a lot.

The whole piece is great - go read it!

Article: The Dribbblisation of Design!

Paul Adams over at Intercom has a great article about the design process of an useful product:

Once you have a clear mission, vision and product architecture, you can start to think about the other details. The goals people have, what makes them happy, fulfilled, successful. The jobs your product does for them, where it works well, where it doesn’t.

He points out the need to implement design around jobs-to-be-done:

At Intercom, we’re working with Clay Christensen’s Jobs framework for product design. We frame every design problem in a Job, focusing on the triggering event or situation, the motivation and goal, and the intended outcome:

When _____ , I want to _____ , so I can _____ .

For example: When an important new customer signs up, I want to be notified, so I can start a conversation with them.

This gives us clarity. We can map this Job to the mission and prioritise it appropriately. It ensures that we are constantly thinking about all four layers of design. We can see what components in our system are part of this Job and the necessary relationships and interactions required to facilitate it. We can design from the top down, moving through outcome, system, interactions, before getting to visual design.

One feels almost forced to match this with the well-known Steve Jobs quote:

''Most people make the mistake of thinking design is what it looks like,'' says Steve Jobs, Apple's C.E.O. ''People think it's this veneer -- that the designers are handed this box and told, 'Make it look good!' That's not what we think design is. It's not just what it looks like and feels like. Design is how it works.''