Roadmaps in Agile, part 1

As a product manager in an agile development model, one of the most difficult things to do is building a roadmap. This is because making feature commitments for six to nine months out feels contrary to the spirit of being “agile” and maintaining flexibility to change course to support the needs of the business.

Why is having a roadmap when you’re agile so hard? One word: sales. It’s relatively easy (provided you know how to do it) to move requirements around when the only people you’re communicating with are internal stakeholders. It’s much harder when a sales guy has already told the Big Prospect that the frimfram feature is going to be added in third quarter, based on a roadmap that he saw six months ago. Sales cycles have their own momentum, they have their own set of unforeseen requirements that weren’t planned for, and they’re very hard to sync up with a roadmap that’s moving to respond to current and future needs of the company and customers.

So how do you do it? There are three important dimensions to any roadmap, and those are priorities, cost/benefit, and time. Getting the first two properly defined is critically important; once you have that, distributing the roadmap across time is more of a mechanical exercise (but not without its hazards). First, though you have to know:

What do we need to do? If you’re a product manager who documents every requirement you ever unearth from a customer, prospect, sales guy, internal operations perspective, or executive, stores it in a backlog, and periodically revisits the backlog to organize and categorize it, this step might actually be relatively easy. If not, it will require some legwork–talk with each stakeholder, make sure customer voices are represented through input from the sales force (and/or SalesForce), write everything down, send the list around and make sure that nothing got missed.

What do we do first? Prioritization has to be done as a conversation; there’s no way around it. You can do prioritization in a vacuum if you’re using a static set of priorities (high, medium, low, for example), but if you’re stack ranking your requirements (which I firmly believe is the best way to go) you need the appropriate stakeholders to get together and make the tradeoffs. To do a good job in stack ranking, it helps to set some ground rules (e.g. the requirement contributes to current revenue, builds groundwork for future revenue, or reduces operational costs) and set some rules about how those translate into ranks (e.g. current revenue more important than future revenue). There are some finer dimensions to the problem; generally there are different types of requirements and different types of people who will work on them, so if you slice the prioritized list by those dimensions do the priorities still make sense? (They should.)

What’s the cost and benefit? Ideally this should be done before prioritization, since it informs it, particularly the benefit part. If you have a major initiative that’s supposed to drive new business, someone should be able to estimate how much new  business it will drive. Engineering requirements can be estimated by cost. Combining the two can help to drive prioritization. It’s important to know the details of the business model behind the requirement, too. If the revenue plan for the requirement assumes that it will help to drive revenue for two quarters, it had better be released by the middle of the year.

When do we do what? Here’s where the rubber hits the road. Up until this point, it’s better to deal with requirements as high level objects–epics of work that can span multiple teams and releases. But to actually assign features to releases, you need to be able to at least guess at a high level division of work (we’ll work on this for three release cycles before it becomes available to the public) and of responsibility (both teams A and C contribute, so we need to put something in both team’s work plans).

The reason that time based planning is trickier, too, is that it needs to make explicit assumptions about certainty. You can do a pretty concrete plan for releases early in the calendar year, because you know that the business requirements won’t change too much between planning time and the release date. But the back half of the year is far trickier. So each release during the year needs an increasing “change reserve,” unallocated capacity that can take on new requirements. Alternatively, management has to be comfortable with the proposition that the out quarters will be highly subject to change.

Once you’ve done the basic blocking and tackling, the real fun begins: how do you communicate this nuanced plan in a consumable format to management and sales? Well, that’s part 2.

Grab bag: Omens of change

Grab bag: Tuesday is the new Monday edition

Grab bag: Forgotten and unforgettable

Remembering Gilly Sullivan

UVA Today: Gilly Sullivan, Former U.Va. Alumni Association Director, Has Died.

If the worth of a man is measured in the impact that he left on the lives of others, Gilly Sullivan was the most important man I’ve ever known. He was dedicated to helping students at the University of Virginia and to ensuring that Mr. Jefferson’s principles of student self-governance were consistently upheld, and he was able to produce miracles in a way that no one else associated with the institution seemed able.

I had three separate interactions with Gilly. In one, he was the bearer of the news that I had won an alumni-sponsored scholarship that I didn’t know existed and had never applied for. In the second, he helped save the magazine that I had cofounded just an issue before when our business manager decided not to sell any ads and not to tell me about it.

In the third, which began before I got to the University and continued the whole time I was there, he was the guardian angel that helped ensure the survival of the Virginia Glee Club as an independent organization when the UVA music department wanted to subsume it into a mixed chorus. He did it by ensuring that the music department couldn’t claim any control over the Glee Club’s alumni-funded endowment, thus ensuring we’d have some way to survive without department support. He was similarly instrumental in helping the revival of the UVA Women’s Chorus.

I wrote a Wikipedia entry for Gilly a few months ago but never shared it with the broader world until this week; I wanted to dig deeper to find more information about the man. For all his influence, he left a remarkably small impact on the news world–a few articles around the time he retired and that was it. He deserved more praise than he got, but I think he knew how much of a difference he made to students like me.

Grab bag: good news, sad news

Grab bag: Bye bye DRM edition

Macworld Keynote 2009

It’s not going to be a Stevenote (and on that note, best wishes to Steve as he gets his hormones back in balance and gets some protein in his system). But I’ll be watching all the more closely, to see how Phil Schiller takes on the challenge of igniting excitement in the Mac faithful. Like many product managers, I have picked up a few tips about presenting product over the years from Steve, and Phil will have his own style and his own techniques which I can hopefully also snarf.

Product predictions? I like John Gruber’s, and can lend credence to the iLife prediction because I finally got the most recent version as a Christmas present. Pretty sure there won’t be any new iPhone products announced today though (outside of the iPhone version of Delicious Library).

I’m pretty sure that Apple won’t be announcing the Mac Wheel today, though (hat tip to Chris Eng for the pointer):

Apple Introduces Revolutionary New Laptop With No Keyboard

Grab bag: Back to work!

Stupid breakage of the day: Ubiquity and MobileMe

This morning I tried to log into MobileMe, which has mostly been working well recently, and got an unsupported browser screen telling me I needed to be running Firefox 2 or later, or Safari. Only problem was I was running Firefox 3.0.5.

I figured it was a bug in MobileMe’s browser check logic, so I used some JavaScript to check what my browser was reporting as its user agent:


It told me I was running

Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv: Gecko/2008120122 Firefox/3.0.5 Ubiquity 0.1.4

Looking at the user string, I wondered if all the addons at the end, in particular the Ubiquity one, were breaking the browser check. So I disabled Ubiquity and restarted the browser. But the user agent string still showed Ubiquity.

I had just updated to the newest Ubiquity release this morning and was starting to think that something in the add-in was causing the problem. So I uninstalled it … and the user agent string was still the same.

Now I was curious. Did it leave a setting behind that the uninstall didn’t clean up? I looked under the hood in the browser preferences at about:config and searched for Ubiquity, where I found a very interesting preference under general.useragent.extra.ubiquity. There didn’t seem to be an option to delete the key, so I simply set its value to an empty string.

Doing the browser check now reported

Mozilla/5.0 (Windows; U; Windows NT 5.1; en-US; rv: Gecko/2008120122 Firefox/3.0.5

And I could log into MobileMe again.


  1. Uninstalling an add-in doesn’t always totally uninstall it.
  2. You might be better off without Ubiquity.
  3. Apple needs to fix the MobileMe browser check (aka Trampoline).

Grab Bag: Almost 25

Grab bag: Delicious Make Television

Favorite albums of 2008

It’s been almost a year since my last “best of” list, so it must be time for another one. Amidst the death spiral of the big music companies, there were a lot of good albums this year, so as before this includes more than a “top 10”:

21d34tcce7lShe & Him, Volume One. Okay, so it’s Zooey Deschanel. But it’s also M. Ward. And the two of them together make some pretty beautiful music. The cover of the Beatles’ “Should’ve Known Better” is one of the nicer surprises on the album, but some of the originals (“Sentimental Heart”) in particular are quite good, and if Zooey’s singing voice is occasionally a little mawkish, her self-harmonies on a few of the tracks are worth the price of admission.

11puaiaefnlNada Surf, Lucky. It wouldn’t be a top ten list from me without a Nada Surf album. This one doesn’t reach the heights of The Weight is a Gift or Let Go, but there are gems nonetheless, like the bizarre polka of “Ice on the Wing” and the yearning pull of “Beautiful Beat” and “Are You Lightning?”

517yq33iftl_sl160_My Morning Jacket, Evil Urges. There aren’t enough good Southern fried jam bands led by falsetto vocalists with undeniable funk tendencies in the world, and this is the best of them. I love the two-parter “Touch Me I’m Going to Scream” for the name and the music, and “Highly Suspicious” and “I’m Amazed” combine to ensure that the band will never be mistaken only for a bunch of left-wing Skynyrd impressionists.

55332s50Okkervil River, The Stand Ins. This band earns their presence on this list both for this album and their previous, The Stage Names, which I just discovered this year. Hat tip to my college classmate Darius Van Arman of Jagjaguwar for signing these guys.

61lilxzuxcl_sl160_Gemma Hayes, Hollow of Morning. A welcome return to the US market by the big-voiced wistful Irish vocalist. Her second album was never released stateside–I have yet to hear it–but her first, Night on My Side, was one of my favorites a few years ago. The new album takes the voice to some familiar places but also some quieter ones; Hayes seems both stronger and more fragile after a rough few years, and it makes for gripping listening.

45826s50Bon Iver, For Emma, Forever Ago. Hard to avoid this album this year, even if you’re consciously trying to listen to fewer angsty indie rock boy music. This album avoids being only angsty indie rock boy music by dint of its rough isolation and its complete bitter sincerity–a bracingly honest musical statement that can’t be listened to in a noisy room.

61oap4rqc9l_sl160_aa115_David Byrne/Brian Eno, Everything That Happens Will Happen Today. It sure isn’t My Life in the Bush of Ghosts II, and it didn’t have to be. There are some really brilliant songs on the album, David Byrne is in fine voice, and Brian Eno’s musical textures are as squelchy/crunchy/sweeping as ever. So what if Byrne doesn’t touch his guitar nearly enough and Eno’s beats are as white as ever? Well, actually fixing those two things would have made the album a lot better, but it’s still good enough to be on this list.

49317s50Elvis Costello and the Imposters, Momofuku. Put Elvis Costello into a room with a solid bunch of musicians and turn on the mikes and this is what you get–a searingly raucous set of new tunes that tear the status quo a new hole and rock their way into your jeans.

51vixffxrvl_sl160_The Fireman, Electric Arguments. WTF is Paul McCartney doing on this list? Showing the youngsters how it’s done, mostly–some soaring electric moments, some amazing (but not saccharine) ballads, and a healthy dollop of experimentation. Much nicer than his Starbucks release from last year.

21eg6jnaynlCat Power, Jukebox. If Chan Marshall keeps releasing records like this, she’ll make a strong case that she’s this generation’s leading interpreter of popular song–an unlikely successor to the likes of Ella Fitzgerald or even Dusty Springfield, but a strong contender nonetheless. As in Springfield’s case, the backing band doesn’t hurt either. Nice slice of Memphis-ized greater and lesser known songs.

51t8uq6xiql_sl160_Bob Dylan, Tell Tale Signs. I’ve said it before and I’ll say it again: many artists would kill for songs as strong as the stuff Dylan throws away. Tell Tale Signs is effectively a direct sequel to the first three Bootleg volumes, which covered the period up through the mid-80s, and while it mines leftovers from a far smaller proportion of his sessions (Oh Mercy, Under the Red Sky, World Gone Wrong, Time Out of Mind, Love and Theft, and Modern Times), the result is a compelling set of tracks that prove Dylan’s continued vitality.

51822s50Beck, Modern Guilt. After a lightweight party album (Guero) and a disposable “serious” album (The Information), I was skeptical about the new recording, and bringing Danger Mouse to the party felt like a desperate grab for relevance by an artist several albums past his peak. Well, I was wrong–Danger Mouse was an inspired addition to the party (though the one non-DM track, “Chemtrails,” is one of the best on the album), and the album is tighter than anything Beck’s done in years. It hits you in the dance bone and gets out of there in 30 minutes. What more could you ask for?

43196s50Radiohead, In Rainbows. The album so nice they released it twice–digitally and physically–and so wonderful that they earned a place on my best list two years in a row. This year’s release of the live recordings of the material on the “Scotch Mist” video podcast gave me renewed appreciation for the soundcraft behind the sonic textures.

57005s50Shannon Worrell, The Honey Guide. I’ve written about the album at length, so I’ll just say that (a) there’s a reason that it’s been in my sidebar for months and (b) “If I Can Make You Cry” may be one of the strongest individual songs of the year. Shannon, when are you going to come up to Boston?

54044s75Vampire Weekend, Vampire Weekend. A candidate for fun party-music album of the year, this album features a bunch of white kids playing Afropop music and totally pulling it off. That their lyrics are about trust-fund kids from the Cape is a precious conceit, but the songs are fabulous nonetheless.

You can also see the list at Lists of Bests.