SBS 2008, Hewlett Packard, WSS3, Search Server 2008 Express and a UPS – Oh the pain!

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In the words of Doctor Smith from lost in space, while everyone else was in Vegas having a grand old time, I was at a client site, having to come to grips with the beast known as Windows Small Business Server 2008. I rarely work with SBS2003 and had never used SBS2008 until now.

This was one of those engagements that is somewhat similar to those awful dreams that you have when you are trying to get to some place, but you never quite get there and your subconscious puts all sorts of strange and surreal obstacles in your path. In my case, the surreal obstacles were very real, yet some of them were really really dumb. Whatsmore, it is a very sad indictment on IT at several levels and a testament to how complexity will never be tamed with yet more complexity.

As a result, I really fear the direction that IT in general is heading.

So where to begin? This project was easy enough in theory. A former colleague called me up because he knew of my dim, dark past in the world of Cisco, Active Directory and SharePoint. He asked me to help put in SBS2008 for him, configuring Exchange/AD/SharePoint and migrating his environment over to it.

“Sure”, I say, “it’ll be a snap” (famous last words)


I haven’t use the coffee or tequila ratings for a while, so I thought that this post was apt for dusting them off. If you check the Why do SharePoint Projects Fail series, you will see that I use tequila shots or coffee at times. In this case, I will use the tequila shots to demonstrate my stress levels.

Attempt 1

We start our sorry tale a few weeks ago, where my client had ordered Small Business Server 2008 and the media/key had not arrived by the time I was due to start. The supplier came to the rescue by sending them a copy of the media and promised to send the license key in a couple of days.

The server was a HP Proliant DL360 G6, a seemingly nice box with some good features at a reasonable price. HP/Compaq people will be familiar with the SmartStart software and process, where instead of using the windows media, you pop in the supplied SmartStart CD and it will perform some admin tasks, before asking for the windows media, auto-magically slipstreaming drivers and semi-automating the install.

On client machines, I never use the CD from the vendor because there is always too much bloatware crap. However on servers I generally do use the CD, because it tends to come with all the tools necessary to manage disk storage, firmware and the like. I dutifully popped in SmartStart CD, answered a few basic questions, and it asked for the windows media CD.

Cleverworkarounds stress rating: Good so far

Next it asked me for the Windows SBS2008 licence key. Of course, I was using media that had been lent to us from the supplier because my client’s media (and keys) had not arrived. Thus, since I did not have a license key I was unable to proceed with the install using this preferred manner. HP, in their infinite wisdom, have assumed that you always have the license key when you install via their SmartStart CD, despite Microsoft giving you 30 days to activate the product. To be fair on HP, they are hooking into Microsoft’s unattended installation framework, so perhaps the blame should be shared.

All was not lost however. The SmartStart CD can be run after windows has been installed. It then will install all the necessary “HP bits” like graphics and system board drivers. So I booted off the Windows CD and fortunately, windows installer detected the HP storage controller and the disk array,  and proceeded to let me partition it and install.

Cleverworkarounds stress rating: Minor annoyance, but good so far

Small Business Server 2008 did its thing and then loaded up a post install wizard that sets the timezone, active directory domain name and the like. At a certain step when running this wizard, SBS2008 informed me that there was no network card with a driver loaded, so it could not continue. As it turns out, Microsoft’s initial SBS2008 configuration wizard simply will not proceed unless it finds a valid network card. But since this is the pre-install wizard, we are not yet at the point in the installation where we have a proper windows desktop with start menu and windows explorer. All is not lost (apparently), because SBS allows you to start device manager from within the wizard and search for the driver.

Fair enough, I think to myself, so I pop in the HP SmartStart CD and tell device manager to search the media.

Cleverworkarounds stress rating: Spider senses tingle that today might not turn out well


Windows device manager comes back and tells me that it cannot find any drivers.


Well after some examination, the SmartStart drivers are all self extracting executables and therefore device manager could not find them when I told it to. Of course, the self extracting zip files have hugely meaningful names like C453453.EXE making it really obvious to work out what driver set is the one required… not!

Luckily, Ctrl+Alt+Del gave me task manager which allowed me to start a windows explorer session, and I was able to browse to the CD and run the autorun of the SmartStart CD manually. This loaded up HP’s fancy schamsy driver install software that produces a nice friendly report on what system software is missing and proceeds to install it all for you.

SmartStart did its thing, finding all of the driverless hardware and installed the various drivers. A few minutes and a reboot later and SBS2008 reruns its configuration wizard and this time finds the network and allows me to complete the wizard. This triggers another thirty minutes of configuration and another reboot and we have ourselves a small business server!

Cleverworkarounds stress rating: Spider senses subside – back on track?

Next I did something that is a habit that has served me well over the years (until now). I reran the Smartstart CD, now with a network and internet access. This time I told the driver management utility to connect to HP.COM. It scanned HP and reported to me that most drivers on the SmartStart CD were out of date. This is unsurprising because most of the time I do server builds for any vendor, I find that about half of the drivers, BIOS and various firmwares have been replaced by newer versions since the CD was pressed.

Since this is a brand new server build, it is a habit of mine to upgrade to the latest drivers, BIOS and firmware before going any further.

Among the things found to be out of date was the BIOS, the firmware on the RAID Storage controller as well as the network card. The SmartStart software downloaded all of these updates, and another reboot later, all are installed happily. Another hour of patching via Windows update, and we have a ready to go SBS2008 server with WSS3, Exchange, SQL Express and WSUS all configured automatically for you.

Cleverworkarounds stress rating: This SBS2008 stuff isn’t so bad right?

Okay, so things were good so far, but now here is where the fun really begins.

Windows 2008 SBS comes with a pre-installed WSS3 site called http://Companyweb. As we all know, search completely sucks in WSS3. It has a bunch of limitations and isn’t a patch on what you get with MOSS. But no problem – we have Microsoft Search Server Express now, a free upgrade which turns WSS search from complete horribleness to niceness fairly quickly.

For those of you reading this who run WSS3 and have not installed Search Server Express, I suggest you investigate it as it does offer a significant upgrade of functionality. Search server express pretty much makes WSS3 have the same search capabilities of MOSS 2007.

So, I proceeded to install Search Server 2008 express onto this Small Business Server 2008 box. I have installed Search Server Express quite a few times before and I have to admit, it is a tricky install at times. But given that this was a fresh Small Business Server 2008 install and not in production, as well as having successfully installed it on Small Business Server 2003 previously, I felt that I should be safe.

I commenced the Search Server 2008 express install, and the first warning sign that my day was about to turn bad showed itself. The install of search server express only allowed me to choose the “Basic” option. The option that I wanted to use, “Advanced” was greyed out and therefore unavailable.

Cleverworkarounds stress rating: Spider senses tingling again


Knowing this server was not in production, I went ahead and allowed Search Server Express to install as per the forced basic setting. The install itself appeared to work, but it died during the SharePoint configuration wizard. It specifically crapped out on step 9, with the error message

“Failed to create sample data. An exception of type Microsoft.SharePoint.SPException was thrown.  Additional exception information: User cannot be found”.

“Curses!” I say, “another trip to logs folder in the 12 hive”. For the nerds, the log is pasted below.

[SPManager] [INFO] [10/21/2009 3:38:47 PM]: Finished upgrading SPContentDatabase Name=ShareWebDb Parent=SPDatabaseServiceInstance Name=Microsoft##SSEE.
[SPManager] [DEBUG] [10/21/2009 3:38:47 PM]: Using cached [SPContentDatabase Name=ShareWebDb Parent=SPDatabaseServiceInstance Name=Microsoft##SSEE] NeedsUpgrade value: False.
[SharedResourceProviderSequence] [DEBUG] [10/21/2009 3:38:47 PM]: Unable to locate SearchDatabase. Exception thrown was: System.Data.SqlClient.SqlException: Cannot open database "SharedServices_DB_ed3872ca-06b1-44c5-8ede-5a81b52265f9" requested by the login. The login failed.
Login failed for user ‘NT AUTHORITY\NETWORK SERVICE’.
   at System.Data.SqlClient.SqlInternalConnection.OnError(SqlException exception, Boolean breakConnection)
   at System.Data.SqlClient.TdsParser.ThrowExceptionAndWarning(TdsParserStateObject stateObj)
   at System.Data.SqlClient.TdsParser.Run(RunBehavior runBehavior, SqlCommand cmdHandler, SqlDataReader dataStream, BulkCopySimpleResultSet bulkCopyHandler, TdsParserStateObject stateObj)
   at System.Data.SqlClient.SqlInternalConnectionTds.CompleteLogin(Boolean enlistOK)

The long and short of this error takes a little while to explain. First we need to explain the historical difference between SQL Server Express edition and SQL Server Embedded edition (also known as the Windows internal database). From wikipedia:

SQL Server 2005 Embedded Edition (SSEE): SQL Server 2005 Embedded Edition is a specially configured named instance of the SQL Server Express database engine which can be accessed only by certain Windows Services.

SQL Server Express Edition: SQL Server Express Edition is a scaled down, free edition of SQL Server, which includes the core database engine. While there are no limitations on the number of databases or users supported, it is limited to using one processor, 1 GB memory and 4 GB database files.

Why does this matter? Well Microsoft, being the wise chaps that they are, decided that when you perform a SharePoint installation using the “basic” option, different editions of SharePoint use different editions of SQL Server! Mark Walsh explains it here:

  • When you use the "Basic" install option during MOSS 2007 installation it will install and use SQL Server 2005 Express Edition and you have a 4GB database size limit.
  • When you use the "Basic" install option during WSS 3.0 installation it DOES NOT use SQL Express, it uses SQL Server 2005 Embedded edition and it DOES NOT have a 4GB size limit.

It happens that Small Business Server 2008 comes with WSS3 preinstalled. Annoyingly, but unsurprisingly, the Small Business Server team opted to use the BASIC installation mode. As described above, SQL Server Embedded Edition (known on Win2008 as the Windows Internal Database) is used. For reference, WSUS on Small Business Server 2008 also uses this database instance.


Search Server 2008 Express, uses SQL Server Express edition when performing a basic install. As a result, an additional SQL Server Express instance (SERVERNAME\OFFICESERVERS) gets installed onto the Small Business 2008 server. Then, to make matters worse, the installer gets mixed up and installs some Search Server express databases into the new instance (a Shared Service Provider), but then uses the SQL Embedded Edition instance to install other databases (like the searchDB). Then later during the configuration wizard, it cannot find the databases that it needs because it searches the wrong instance!

The net result is the error shown in the log above. I tried all sorts of things like copying the Express databases into the embedded edition, but I couldn’t disentangle this dependency issue. Some parts of SharePoint (the search server express bits no doubt) looked in the SQL Express instance and the WSS bits looked in the Embedded SQL instance. Eventually, conscious of time, I proceeded to uninstall Search Server Express.

Cleverworkarounds stress rating: Some swear words now uttered


Uninstalling Search Server Express was attempted and tells me that it has successfully completed and wants a reboot. Unfortunately SharePoint is now even more hosed than it was before and I tried a few things to get things back on track (psconfig to create a new farm and the like). After more frustration, and conscious of time I decided to uninstall WSS3 altogether and then reinstall it according to the SBS Repair guide for WSS3.

This had the effect of stuffing up WSUS as well! (I assume because it shares the same Windows Internal Database instance), and after a couple of hours of trying all sorts of increasingly hacky ways of getting all of this working, I was forced to give up.

Note: Whatever you do, do not attempt this method. At one point I tried to trick WSS3 into temporarily thinking it was not a basic mode install so get Search Server Express to prompt for Advanced mode, but it made things worse because the configuration database got confused.

Cleverworkarounds stress rating: Installing SharePoint in basic mode is committing a crime against humanity.


Attempt 2


At this point I hear Doctor Smith abusing me like the poor old robot. “You bubble-headed booby, you ludicrous lump, adlepated amateur, dottering dunderhead”.

Since WSUS got completely screwed, as well as the Windows Internal Database through relentless uninstallation and repair attempts, I started to get nervous. Small Business Server 2008 is a very fussy beast. Essentially it can get very upset at seemingly benign changes. I felt that I had messed about so much that I could no longer guarantee the integrity of this server so I wiped clean and reinstalled.

I installed Windows as per the previous method, and once again the install wizard stopped, asking me for a network driver. Once again I popped in the HP SmartStart CD and proceeded to run the driver install program from the SBS configuration wizard.

This time, no network card was detected!

What the? During attempt 1, I happily installed the necessary HP drivers using the same %$^#% SmartStart CD! Why is it not detecting now??

Cleverworkarounds stress rating: Now thinking about how much fun everyone is having in Vegas while I am fighting this server


After some teeth gnashing, the cause of this problem hit me as I was driving home from the site. I had upgraded the firmware of the network card during attempt 1, as well as the storage controller and system BIOS. I realised that the stupid, brain-dead HP network card drivers likely could no longer recognise its own network card with a newer firmware.

The next day I came back refreshed, and found that indeed, there were newer network drivers at the HP site. I downloaded them and extracted them and sure enough, suddenly the network card was found and I was back in business. How dumb is that! Surely if you are going to write a driver, at the very least make it recognise the hardware irrespective of firmware!  

Once I got past this stupid annoyance, it did not take too long for SBS2008 to be installed and ready to go. Remember that WSS3 is installed for you in basic mode, so to change it requires an uninstall of WSS and then to reinstall it in a different mode. But the problem here is SBS2008 and its fussiness about messing with configuration. In going down this path, you risk future service packs and updates breaking because things are not as expected. Additionally you would have to create companyweb manually and it raises the risk of a misconfiguration or mistake along the way.

I logged a call with Microsoft and got a pretty good engineer (hey Ai Wa) and she was able to consistently reproduce all of my issues in the lab, but was unable to work out a supportable fix. In the meantime, I tried to force Search Server 2008 to install into advanced mode using a scripted install, using an article written by my old mate Ben Curry. Alas, I could not bend it to my will and at the time of writing this article, I had to give up on Search Server 2008 with SBS2008 for now.

For what its worth, I know that I can make this work by installing WSS3 differently, but I planned to properly nail this issue in my lab using the out of the box installs and then publish this article, but I didn’t have the sufficient hardware to run Small Business Server 2008. It requires a lot of grunt to run! So I will revisit this issue once my new VM server arrives and post an update.

But there is more…

If the whole Smartstart, network driver, SBS2008 with its dodgy scripted WSS3 install, with Search Server Express dumb installation assumptions were not enough, I hit more dumb things that resulted in showing how ill equipped HP’s support is able to deal with these sorts of issues.

The server, not surprisingly, supplied with a nice hardware RAID configuration and my client opted to buy some additional disk. When the disks arrived and were installed, we found that the RAID controller could see the disks, but we were unable to add the disks to the existing array using HP’s management tools. HP’s “friendly” support was unable to work out the issue and asked me to do things that were never going to work and insulted my intelligence. Eventually I worked out what was going on myself, via HP’s own forums. It turns out that the HP Server requires a write cache module to be able to grow an array. We had one of these installed. Upon further examination by opening up the chassis, we were missing a battery to go with the write cache module. HP were unable to determine the part number that we needed and we ended up working it out ourselves and telling our supplier.

Then HP stuffed up the order and after following up for two weeks, it turned out they accidentally forgot to put the order through to Singapore to get the part. It seemed that once we went outside of the normal supply chain system at HP, it all broke down. After two weeks and numerous calls, they suddenly realised that the part was available in Sydney all along and it was shipped over next day!. The irony was that next day the part from Singapore arrived!

So now we had two batteries.

Grrrr. It shouldn’t be this hard! Why supply a write cache module and not supply the battery! Dumb Dumb Dumb!

Cleverworkarounds stress rating: Really hating HP and Microsoft at this point.


… and piece de resistance!

Okay so we had a few frustrating struggles, but we more or less got there. But here is the absolute showstopper – the final issue that for me, really made me question this IT discipline that I have worked in for twenty years now.

My client rang me on Monday morning to tell me the server was powered off when we arrived on site. This was unusual because the rack was UPS protected and no other devices were off. We ran HP’s diagnostic tools and no faults were reported. The UPS was a fairly recent APC model, and we installed a serial cable to the server and loaded the APC UPS Management software. The software (which looks scarily like what 16 bit apps used to look like in the early 90’s), found the UPS and showed that was all hunky dory.

We decided to perform a battery test using the software. No sooner than I clicked OK, the server powered off with no warning or shutdown. Whoa!!

I put in a call to APC, and was told that the UPS was not compatible with HP’s new fancy shmansy green star rating power supplies. We had to buy a new UPS because of some “sine wave” mumbo jumbo (UPS engineer talk that I really wasn’t interested in). If the UPS switched to battery, this server would think power was dodgy and do a pre-emptive shutdown. The reason that the server was powered off on the Monday morning was that the UPS has a built in self test that runs every 7 days that cannot be disabled!

Cleverworkarounds stress rating: For %%$$ sake!.



Now I don’t know about you, but once a UPS cannot be “compatible” with a server, that’s it – things have gone too far. For crying out loud, a UPS supplies power. How $%#^ hard can that be? How is an organization supposed to get value out of their IT investments with this sort of crap to deal with.

Then add in the added complexity of Blade servers, Citrix, Virtualisation, shared storage, and I truly feel that some sites are sitting on time bombs. The supposed benefits in terms of efficiency, resiliency and scalability that these technologies bring, come at an often intangible and insidious cost – sheer risk from incredible complexity. If you look at this case study of a small organisation putting in a basic server, most of the issues I have encountered are the side effects of this complexity and the lack of ability for the vendors to be able to help with it.

As the global financial crisis has aptly demonstrated, when things are complex and no-one person can understand everything, when something bad does happen, it tends to do it in a spectacularly painful and costly way.

Finally, before you reply to this likely immature rant and tell me I am a whiner, remember this all you Vegas people. You got to have fun and marvel at all the new (complex) SP2010 toys, while I sat on the other side of the planet in a small computer room, all bitter and twisted, sprouting obscenities to HP, Microsoft and APC dealing with this crap. When you put that into perspective, I think this article is quite balanced! 🙂

Thanks for reading

Paul Culmsee

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A simple way to improve your estimating (and a cool pub trick) – Conclusion

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…and we’re back!

Well… that was a long commercial break wasn’t it 🙂

In case you missed part 1 of our version of the show “deal or no deal”, you missed the big cliff-hanger and you really should read part 1 first. For the rest of you, to quickly recap, I came out of the closet and admitted by secret teenybopper shame, told the world that my wife had a teenage thing for Jean Claude Van Damme, showed the effect of beer goggles and introduced the notion of cognitive bias and how it can affect judgement.

i also demonstrated how, by altering the frame of reference, to a problem something that at first seems completely unquantifiable “how the hell do I know how many SharePoint developers drive yellow cars?”, is actually not as “impossible” as you may first think.

At the end of the last post I left you with a $10000 dilemma. You had to make a “deal or no deal” decision about going with your estimate about SharePoint developers who own yellow cars, or to instead cast your lot with a bag of marbles with a 9 in 10 chance of winning the prize. Just to refresh your memory, here is the salient part of the pub conversation.

  • Me: Okay, so you are 90% sure that here are between 300 and 2000 SharePoint developers in the world with a yellow car?
  • Them: Yes
  • Me: So, let’s make this like the game show “deal or no deal”. If you are right and the answer is within your range, you will win $10000. BUT you have an alternative…
  • Them: Ok…
  • Me: What if I were to present you with a bag containing 9 red marbles and 1 black marble and offer you $10000 if you pull out a red marble. Pull the one black marble, and you miss out on the money. Do you want to stick to your estimate or do you want to draw a marble?

So have you decided? Now be honest and see how you went against the 4 outcomes that I have experienced when trying this on people. Here are the possible answers in order of popularity…

  1. The person chooses to pull from the bag of marbles rather than their ranged estimate. (This is the predominant answer for all people I have tried this with – perhaps 70-75% of all responses).
  2. The person chooses to use their estimate over the bag of marbles. (perhaps 25% of people have answered with this option)
  3. Upon hearing the bag option, the person wants to change their ranged estimate. (Happened to me once)
  4. The person doesn’t care which method.. (never happened to me)

So which is the right answer to this question?

(drumroll) Lets tackle the possible answer in order of likelihood.

“Take the marble! take the maaaaaarble!”

For the 70 odd percent of you who opted to take your chances with the bag of marbles, GONG! you lose!

Better double check your estimates in future because you have demonstrated that you are over-confident in your estimates. In other words, you are suffering from optimism bias. To explain why, think about the original question carefully. I asked originally for a ranged estimate that you were 90% confident with.

I then presented an alternative that has a 9 out of 10 chance of success – also 90%. From a statistical point of view, you should be completely ambivalent as to which option to use. Therefore, despite being asked for a range that you were 90% confident with, the range you actually estimated is not really 90% at all. It has to be less than 90% for you to prefer a clear 9/10 probability.

So that is why you are so stressed and busy! You keep giving crap estimates that make life harder for you! 🙂 Either that or you are too nice and when your project manager looks at you with those big, sad project manager eyes, your heart melts and you relent.

Isn’t that cool in a nerdy way? It is very interesting to see people’s faces as the penny drops to this logic and they suddenly realise just how bad some of their past estimates have been as a result. The consolation prize is just about 4 out of 5 people do exactly the same as you and take the marbles.

“No deal, I will stick with my estimate”

For the smaller group who decide that their estimate is preferred, you also lose.

In this case, the reason why should be pretty obvious. You are so paranoid about getting it wrong, that you have made an estimate that is more like 95% or even 99% confident. Why? your range is too wide for 90% because when presented with a clear 9/10 chance of success, you chose your original estimate. While that may sound like you are confident, in reality you are a bit of a wuss, because in fact you are under confident with your estimate. So grow some balls you weenie 🙂

Honorary mention – “I want to change my estimate”

At the Best Practice Conference in DC, I attempted this pub trick on Yoav Lurie from Synteractive, who is much more of a business and strategic thinker than us IT nerds. His response I think, deserves an honorary mention for being the closest to winning the game. In this example, I asked him to estimate in feet, the wingspan of a Boeing 747. I knew instantly that he was a good estimator because of the logic he used to come to a range.

“Hmm, well an aircraft seat is maybe one and a half feet, and there will be 10 seats in the cabin, with two passages that are probably two feet in width…so that ads up to…”

What do you notice about what Yoav did? Straight away, he related the wingspan of an aircraft (a clear unknown), to something he could make a reasonable estimate of (the width of an aircraft seat). After all, we have all sat in an aircraft seat in sardine (economy) class and know how cramped it is. He knew there were three rows of seats and related this to the width of the cabin, which he then related to the size of the wing. Deducing that the wing might be 4 to 6 times the width of the cabin, he then was able to make a very good ranged estimate of the overall wingspan of the plane.

I was very impressed at his estimate and how he arrived at it, but I still got him 🙂

As soon as I presented him with the bag of marbles alternative, without missing a beat he said “I want to change my estimate”. It took only a split second of presenting a clear 90% probability made Yoav realise that his estimate was not 90% and he was still a little overconfident.

That being said, Yoav’s method of relating something known to help frame the reference to something unknown is the only time anyone has used any sort of rigour in forming an estimate and very impressive for the pub setting 🙂

The right answer

Okay, so as you may have guessed by now, the right answer is to shrug your shoulders and say “I don’t care” or wave your hand at me and say “pfft, whatever”. (This is one of the few times saying you couldn’t care less is the right answer). In doing so, you have placed equal weight upon the choices, based on the assumption that both are 90% probabilities.

Neat pub trick huh? It certainly gets people thinking.

How to calibrate yourself

Douglas Hubbard talks about “calibrated estimates” in his books and has an appendix of calibration questions, that are designed to help you perceive and account for cognitive bias in your estimating.

What you should take away from this exercise is that when asked to estimate on something you are uncertain about, make your initial estimate. Then, pretend you are in the game show and you have to pick between this estimate and the marble. If you feel that you would take the marble over your estimate, increase the width of your range until you feel that it doesn’t matter which option you pick.

Conversely, if you are one of the wimps who are under confident, then reduce the width of your range, until you feel that you have no particular preference of your estimate vs. the marbles.

In the same way that reframing a problem led from something being unquantifiable to something that indeed had a upper and lower range, by reframing the estimate against a unambiguous probability such as a bag of 10 marbles with 9 red, helps you to account for cognitive bias in your estimates.


So to reiterate my key points to this post

  1. Many things that seem unquantifiable are easier to quantify than you think, once you think in terms of ranged estimates and probability.
  2. Your bad taste in fashion and music when you were a teenager still manifests itself today and it is called cognitive bias.
  3. There are easy methods that you can use to calibrate yourself better so that your estimating radar is more finely tuned.

Most importantly of all however, you learned that my wife liked Jean Claude Van Damme in the 80’s and you know that I am in big trouble when she reads this! 😛

Thanks for reading


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A simple way to improve your estimating (and a cool pub trick) – Part 1

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Okay I’ll admit it, I used to really suck as a time and effort estimator. I happen to have a business partner who is much better at it than me (hey Peter), and every time I sought a second opinion from him on my estimates, he would almost always make a much less optimistic assessment then me. Of course, Peter was almost always right too, dammit.

So, why was Peter much more accurate with his estimates?

The answer to this question, all one has to do is think back to their teenage years, where they went through that awkward stage where you look back and cringe at the posters that were on your wall and your choice of fashion. For many, this period demonstrates some utterly appalling choices of taste. Mine are particularly cringe-worthy, given that these days I am a bit of a metalhead. My favourite song at the time was Respectable by Mel and Kim. I thought that Karate Kid II was the best film of all time (and that the girl in it was hot). Mind you, my wife has an even more shameful secret. She had a crush on Jean Claude Van Damme! Mwahahahah 🙂

These are examples of a phenomenon I like to call “Teenybopper bias” 🙂

Now, there is a point in telling you about my wife’s secret shame and it isn’t to see her reaction when she reads this (okay, well maybe a teenie bit). These examples of “what the hell was I thinking” are a form of cognitive bias that took place at the time the opinion was formed. In terms of teenybopper bias, the root of the bias is likely the same hormones that caused your face to break out with acne and hair to grow in funny places. Another very common cognitive bias that afflicts people whether young or old is good old “beer goggle” bias illustrated below.

There are many, many forms of cognitive bias documented, such as optimism bias, anchoring, hindsight bias and the recency effect to name a few. Now let’s take the final image above and pretend we asked someone at the pub for an estimate on a project at 8pm, 10pm and 1am. I’d be willing to bet that the estimate gets more optimistic on a par with how optimistic the perception of the people in the image above become.

Overcoming cognitive bias

Kailash writes about the risk that cognitive bias can play in project failure, particularly in the perception of risks.

overcoming biases requires an understanding of the thought processes through which humans make decisions in the face of uncertainty.  Of particular interest is  the role of  intuition and rational thought in forming judgements, and the common mechanisms that underlie judgement-related cognitive biases.   A knowledge and awareness of these mechanisms  might help project managers in consciously countering the operation of cognitive biases in their own decision making.

The essential difference between Peter and myself in our estimating, is that Peter happens to have a much more finely tuned radar to optimism bias in particular. Douglas Hubbard of Applied Information Economics fame, writes about the effect of cognitive bias extensively in his two books and offers a simple, yet highly useful method to quickly improve the quality of estimates which I will explain with an example below.

The great thing about learning about your cognitive biases and the methods for mitigating them, is that you can use it in the pub too. While I don’t recommend this method for picking up members of the opposite sex, it’s a pretty cool icebreaker.

Thus, I will demonstrate how to improve your estimating accuracy by a mythical pub conversation. Imagine you are onto your third beer…

  • Me: “How many SharePoint developers worldwide own a yellow car?
  • Them: “What the…I haven’t the faintest idea!”
  • Me: “Well, I can understand that, so let’s do an estimate. Give me a range that the answer could fall in, that you are 90% confident with.”
  • Them: “I still can’t give you an estimate, I can’t possibly know something like that.”
  • Me: “Well, could there be a million SharePoint developers who like yellow cars?”
  • “Them: “Don’t be ridiculous, there would be nowhere near a million SharePoint developers – period.”
  • Me: “So you do have an upper bound then, less than a million. Remember this is not about the exact answer, I want a range that you would be 90% confident with.”
  • Them: “Okay I get it. I think it is somewhere between three hundred and two thousand.

Note that at this point, we have already made the initial breakthrough. At first the person found it impossible to make an estimate, yet when I related it to something they did have a fair idea of (the thought of a million people), they made some mental associations and realised they did have some idea of limits after all. Thus, by presenting a better frame of reference that they could use to approach the problem, they were able to move from “I have no idea” to a wide range of possible values.

The width of the range reflects the uncertainty that someone has about the answer. The more the uncertainty, the wider the range. Some project mangers hate being given a ranged value because it really mucks up their task or project work breakdowns. As a result, they always want the “ball park” or something that is a single value. I completely understand why this happens, but what these people forget is that an estimation is uncertain by definition. The obvious way to express uncertainty is with a range of values! So asking someone for an estimation and then complaining that it is not accurate enough actually makes no sense. A manager might not like the “width” of the range, but you can’t force someone to reduce their uncertainty just because it doesn’t fit the plan. Unless you provide them with the means to reduce this uncertainty, you cannot and should not try and artificially reduce this range through pressure and coercion.

But despite my observation of the flawed logic of dealing with uncertainty in estimating, a ranged estimate alone is not enough yet. We still have not accounted for the sorts of cognitive bias that I described earlier in the article. So without further adieu, I present a simplified version of Hubbards ‘calibration’ techniques that account for bias. Let’s continue the bar conversation.

  • Me: Okay, so you are 90% sure that here are between 300 and 2000 SharePoint developers in the world with a yellow car?
  • Them: Yes
  • Me: So, let’s make this like the game show “deal or no deal”. If you are right and the answer is within your range, you will win $10000. BUT you have an alternative…
  • Them: Ok…
  • Me: What if I were to present you with a bag containing 9 red marbles and 1 black marble and offer you $10000 if you pull out a red marble. Pull the one black marble, and you miss out on the money. Do you want to stick to your estimate or do you want to draw a marble?


I’d like readers to think about this before continuing with this article. Make a ranged estimate of the number of SharePoint developers worldwide who drive a yellow car, and then decide whether you want to stick to your estimate or take your chances with the marbles.


(Cue game show music where you have 10 seconds to decide with a little ping sound at the end.)

The suspense is now killing you I am sure. Want to know the correct answer?

Find out after this short commercial break (game show speak for wait till part 2 of this series 🙂 )


Thanks for reading


Paul Culmsee

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