8 Ideas For Tesla’s Next Software Update

My wife and I taking delivery of our Tesla Model S at Fremont Factory in 2015

I’ve been driving a Tesla Model S for three years now and I simply love it. It’s the first vehicle I’ve owned that gets better with age. With every software update, a new set of tricks and features appear at my disposal. It’s hard to imagine commuting and driving along winding roads now without features like AutoPilot and Forward Collision Warnings (features that were automatically added to my car after I had already bought it).  

Naturally, as a product person, spending several hours commuting in my Tesla everyday, I dream up some feature ideas of my own from time to time. And I’ve decided to share some of them here. According to the six degrees of separation theory, someone at Tesla is bound to have a look.

Who knows?

Maybe something will stick.

Eight Feature Ideas and Improvements For Tesla

1. Curated radio and podcasts

I utilize my commute to stay up on my favorite audio content (news, tech, leadership, …), but the media playback experience can be cumbersome while driving, as you have to know exactly what you want to play and select it specifically. I know from my time spent in the TV industry that people love to be entertained with as a little decision making as possible.

It would make things easier if the car analyzed my listening behavior and curated an ongoing, custom feed just for me. Aggregating both on-demand media (like podcasts), and also recorded segments of live broadcasts that match with my topics of interest — combining the playback ability of DVR and the machine learning of personalized media streams.

Resulting in a linear, Pandora-like talk radio station, with a mixture of sure bets and new suggestions.

2. Instapaper integration

I also utilize Instapaper to catch up on articles I want to read, by listening to them on my commute – but I do this manually through the iPhone app and it’s a bit clunky.

It’d be great if Instapaper could be integrated directly into the Tesla’s media interface, playing the audio transcripts like they were any other digital radio station.

Actually, Instapaper’s competitor, Pocket, announced last week that they are focusing on this read aloud ‘podcast’ use case – so fingers crossed for more attention here.

Listening to Instapaper read aloud my backlog of articles in my Tesla

3. Autopilot and motorcycles

When Autopilot is engaged, the Tesla maintains a perfectly center position in the lane – even when a motorcycle passes by in the gaps between cars, which is not ideal (Note I have APv1).

If the car could sense the motorcycle approaching from behind and move to the side of the lane (yet remaining within the lines), the motorcycle would have more clearance as it passed.

Occasionally, as the motorcycle passes by my car’s front bumper, AutoPilot thinks the motorcycle is another car, suddenly appearing in dangerous proximity, and proceeds to apply the breaks. This can be dangerous if the car behind is not paying attention.

Making this change I think would place Tesla as a loved brand among motorcyclists and as an added bonus, this would increase the percent of miles driven using AutoPilot (driving up that KPI).

My drawing of how Tesla might better handle land splitting motorcycles

4. Fort Knox Mode

When I leave my car somewhere, at the airport for example, I’d like to be sure it’s safe and sound.

The iPhone app could notify me if the car is unlocked, or moved, by someone other than myself. This would come in handy when parking at a valet, too – knowing if the car gets taken out for an unauthorized joyride.

And if there were no notifications, I could be more confident in the safety of “our beloved Tessa” (as it’s known to my children who consider the car part of the family).

5. Cool on arrival

Remote cooling the cabin of the vehicle so that it’s comfortable when you return to it on a hot day. You can do this manually today through the Tesla app but you have to remember to do it. Imagine if instead you could schedule a time you expect to return to the car, or better yet, the GPS on your phone could automatically begin the process once you return to a certain proximity.

6. Commute analytics and recommendations

Departure time recommendations based on traffic conditions. I’d love to plot average commute times I’ve had over the last year or so, and see how they historically vary by time of day and how they are changing. It might advise me to leave 15 minutes earlier than normal on Thursdays, where I could save 10 minutes on my commute time.  

7. Weather

A brief weather report for where I’m going (as entered into the Navigation system). Automatic, unless switched off. For longer drives, this might cause me to grab an umbrella or jacket for the destination.

8. Phone app

Contact Favorites.

We need contact favorites.

When I want to call my wife, I have three options: I can either use voice command (and then select which “Jeanine” out of 3 potentials, and then select between her home and mobile number), or scroll through the 1600 contacts in my phone, or I can dial her number manually. None of these are great options when cruising along at 70 MPH.

With 5 to 10 pre-set “favorites”, you could just tap phone icon and tap the pre-set people.

Also, the “mute” button should NOT be adjacent to hangup. It’s easy to tap the wrong one while driving. For this reason, I tend to use the steering wheel buttons when doing conference calls in the car. Alan Cooper calls this notion hiding the “ejector seat lever”.

Alan Cooper on hiding “ejector seat lever” in About Face 3.

With all that being said, it’s been a great three years driving my Tesla, and I expect nothing but more good things to come.

It really is a kick to have the question, “What will my car do next?” always floating through your head, and I look forward to finding out.

– Preston, driver of a Model S

Preston Smalley produced in collaboration with Mark Mizera.

The Power of Asking For Help

Lifebuoy. Photo: ranieldiaz via flickr/CC BY 2.0

At what point in facing a challenge should we resort to asking for help?

The trick here is the word “resort”.

In spite of our better judgments, most of us wait until we’re stuck in the quicksand of a problem before we turn to someone for advice or counsel. But why wait until we’re desperate to seek out assistance? Why let ourselves get to a point of anxiety and frustration when it’s often altogether unneeded?

Why not, instead, make asking for help a built-in part of our work process?

There’s this metaphor in a book by Stephen Covey I read a while back, about the importance of sharpening a saw between cuts, so that the saw doesn’t get stuck in the wood it’s working through.  

“We must never become too busy sawing to take time to sharpen the saw.”

Dr. Stephen R. Covey

When we get busy, it’s easy to spend all of our time working and grinding away at whatever to-do item is looming overhead. But we should remember to find time to “sharpen our saws”, in the sense of finding ways to get better and more efficient at our work. Allowing us to ultimately get more done.

Asking for help is one of the many ways we can seek to “sharpen our saws” as we’re heading into new tasks. And the earlier we seek assistance, the less likely we are to get stuck.

Broaden your perspective

Leading product management for a team can be a lonely job. Often your peers — like the head of engineering or marketing — can’t relate to the specific challenges you face.

I found myself in this situation back when I was running product for Plaxo. As described in a previous post, I was facing a whole host of frustrating challenges. Fortunately, my boss at the time was super supportive and recommended I join Collaborative Gain, something he had received a lot of value from over the years.

Collaborative Gain is an organization founded by Phil Terry that’s anchored by a semi-annual retreat with “asking for help” as its cornerstone.

As a participant, you join a year-round “council” of 15-20 professionals in your line of work, from different organizations and industries. The council remains stable over time (save for an average turnover of 2 or 3 members a year).

This week marks my 14th retreat with my council.

Around the time of my first retreat I was considering applying Lean Startup methods to try various pivots we might make with the business. It was a big moment for myself and the company, and I wasn’t totally confident in my approach. Through what we call a “Request For Help” I led my council through the situation, and the approach I was considering. They not only gave me the confidence I needed to proceed, but also helped me fine-tune the approach, and advised me on how to best position it to my staff.

We often think our situations are unique. But more often than not, they fit into larger patterns that actually are quite common. Having access to a wider range of perspectives and experiences illustrates this, and allows you to apply the lessons already learned by others.

Ask your boss

External peers really help in diversifying your perspective, but perspective isn’t the only thing we should be asking for help with.  

It isn’t always comfortable for you or your boss, but if there’s something in their power that could enhance your performance, it’s necessary that you make it clear to them. It might be something you need their help fighting for. It might be a new challenge. A promotion. Or a more flexible schedule.

Whatever it is you need, be proactive and make it clear to them.

Hit the books

Pursuing higher education is often connected with career advancement, with the educational virtues regarded as almost an afterthought. A means to an end. But a big reason I went back to school for my MBA was fill-in a personal knowledge gap — to understand how product and business leaders think. One of the most valuable aspects of my time at Haas was applying the HBS Case Method where, again, we gained perspective around what previous business leaders did right or wrong by placing ourselves in their shoes. By covering dozens of cases we racked up experience that would have taken decades to learn first hand.

Of course, education comes in many forms, and you never know what new lesson might change your entire outlook on things.

Ask for feedback

Feedback is a gift, and if you don’t ask for it you won’t always get it. For an individual, it might be 360 surveys. For an organization, it might be employee NPS.

If your boss isn’t giving you regular feedback, or maybe they skipped your recent review — take initiative and ask for it. Present your self-review to them and ask for their assessment.

Whatever format suits your situation, don’t wait till it lands at your feet. Be proactive about identifying weaknesses and figuring out how to work around them.

“We all need people who will give us feedback. That’s how we improve.”

Bill Gates

Early in a career, it can feel like everyone but yourself has it figured out – and if you want to move up, you’ve got to start being the one with the answers. But the people who move up and lead prosperous careers do have something figured out — asking for help.  

Everyone has their gaps. Gaps in perspective, gaps in wisdom, and gaps in a skillset. The gaps really aren’t important though – what’s important is what you do about them.

Asking for help should be an early stage of our routine. Something we do automatically – like muscle memory. Without prideful or timid hesitation.

By viewing assistance, and advice as tools in our wheelhouse, and not just last-resort, life-saving devices, we can save ourselves a lot of time and frustration.

Everyone needs help.

Get it early, and get it often.

Preston Smalley produced in collaboration with Mark Mizera.

Designing A Work-life Balance in The Bay Area

Commute traffic in the SF Bay Area. Photo: thomashawk via flickr/CC BY-ND 2.0

A few years ago my Bay Area commute was really getting to me.

One and a half to two hours behind the wheel. Home around seven thirty in the evenings. Never in time for dinner with my family. My little ones already in bed, having also missed them in the morning as I headed off to work early. It was depressing.

Not what I wanted for my life.

Eventually, I worked it out that I’d stay late at the office two nights a week (bringing leftovers for dinner). Then I’d leave early two days a week, so I could be home by five thirty. It made a huge difference.

More time at home with my family, fewer hours in traffic.

And since then, I went on to make it so I could WFH one to two days a week, for the same reasons. Now, when I’m not traveling to my company’s headquarters in Philadelphia, I’m seeing my family a lot more and actually getting to spend quality time with them.

I noticed these changes in my schedule not only improved my time out of the office, but they improved my time on the job as well. Getting to spend more time with my family has made me more present when I’m on the job – better enabling me to listen and mentor, which is a large part of my role. And getting myself more time out of the “trees” more often – away from the drawing board – also helps me to better see the “forest” of product strategy. A win-win, all around.

Now everyone may not be in a position to dictate their schedule to this degree, but everyone has the ability to be proactive in finding their own personal work-life balance.

So what’s the right ratio of work:life these days?

Writer Jessica Wildfire illustrated in a recent article that widely held definitions of “work” and “fun” aren’t held by everyone – and some people enjoy their work more than they enjoy their peers’ various ideas of fun.

I can certainly relate, deriving great satisfaction from my own work. But there are other aspects of my life, which I also enjoy, that can get pushed aside if I’m not strategic about how I spend my time. And careful not to let work automatically “win” over everything else.  

The challenge is staying competitive amongst those who choose not to fight this temptation. Those who do allow work to always “win”. Perhaps telling themselves that they’ll dial it back after this next release, this next quarter, once they retire. Or those who have no intention of dialing it back at all.

Columnist and Senior Editor at The Economist, Ryan Avent discussed in a recent article the growing trend of seeking passion and fulfillment in a person’s work today, whereas previous generations may have seen it as more of a means to an end. The piece went on to discuss that the more people enjoy their labor, the more time they’re able to spend laboring – in turn driving up the competition amongst individuals pursuing the same trade.

So if you’re someone who seems to benefit from a decent amount time away from the drawing board, and you’re competing against those who may not need as much of a break, how do you stay competitive and make time for other areas?

For me, the remedy is being proactive and strategic in finding ways to ensure my time is being spent where I want it to be, and being intentional about the way I spend my time in each of the areas – work, family, fun, etc.

These are a few things I like to keep an eye on and some basic “hacks” for maintaining my optimal work-life balance.

A Glimpse into My Personal System of Checks and (Work-life) Balances

Keep an eye on the big picture

Even with a self-tailored work schedule that “guarantees” a balance in my schedule, I still find that if I’m not careful about scheduling meetings and events and how I organize everything – my work-life balance can quickly get out of whack.

My answer to this is Calendar Bird’s-Eye View in Google Spreadsheet.

Calendars – whether in Outlook, gCal, or your phone – can quickly “bring you into the trees” of all your scheduled appointments. Making it hard to “see the forest” of how you’re spending your time and coordinating major events coming up (both work and personal).

To keep an eye on the bigger picture of how and where I’m spending my time, I maintain a birds-eye view calendar which shows where I’ll be in the morning/afternoon/evening of each day. I then color code whether I’ll be at my local office in Sunnyvale, headquarters in Philly, working from home, OOO on vacation, or in transit traveling. This way I won’t overbook a work trip on top of an important personal event that week. If the proportion of the colors doesn’t seem right, I’ll immediately know and be able to make adjustments.

Excerpt from my Calendar Bird’s-Eye View Google Spreadsheet

Your desired ratio may be different than mine but having a bird’s-eye view – and one that is easy to visualize, like color-coded blocks, can help you maintain your preferred ratios between work and home/family/etc.

Safeguard your “me-time”

Each and every day will throw a peppering of obligations and distractions at you, so take proactive measures to ensure that certain parts of the day aren’t jeopardized. It’s important in our hectic world that we get some time to think and work on our own projects and ideas – and these are the ones that tend to be most jeopardized because no one else will be advocating for them but you. Software developers, call this “flow” or getting “into the zone” but it’s not just useful for those roles.

Find a means of accountability for the other, also important, areas

This could mean investing money in a new exercise program to supply with an extra bit of motivation (shoutout to my fellow Pelaton’ers!), or it could mean scheduling recurring activities with a friend that you’ll find ways to make time for because you don’t want to bail on them.

For me, a great one I’ve found is signing up to coach my kids’ teams. I found this is the best way to periodically be extra present for their sports. I can’t do it all the time but each year I’ve picked one to do which gives me one more reason to get my work done and get to their practices and games.

Coaching baseball for one of my son’s on a day where I proudly awarded him the “game ball” 

Outsource as much as possible

I once read if you could delegate something and the other person could do it 70% as well as you could… do it.

Why not apply this to areas of life… to the time spent doing things you’d rather allocate toward something else?

I’m fortunate enough to afford the outsourcing of things like yard work and cleaning my pool (with a robot) – activities I’m not wild about.

See if there’s anything taking up your time that could be delegated to someone else, and allow you to focus more on something else.

As important as being smart with your time may be, it’s also good to remind yourself why you’re working in the first place.

A post by my friend and career coach, Larry Cornett really spoke to me last year. When he was experiencing some doubt about where his time was being allocated a while back, he made the calculation that 3 ½ total months of his life had been spent in traffic over the last 4 years at his previous job.

In his post, he writes that this was the day something inside of him “snapped,” and ultimately moved him to rethink how his time was being spent. For Larry, this meant ultimately leaving his corporate career to foster an independent one. It really made me think about why we work, though. All of us, in general.

Whatever your situation – as far as commute, homelife, etc. – we all make a thousand choices every day about the way we spend our time, and where it’s allocated.

There’s no reason not to be proactive with our time and choose how we spend it wisely.

Preston Smalley produced in collaboration with Mark Mizera.

It’s that time again… I’m riding to put an end to MS.


As many of you know I ride each year in support of a cause close to my heart: raising awareness and money to support an end to multiple sclerosis (MS). I got involved in the cause in support of my son’s godfather who was diagnosed a number of years ago and thru conversations with you have learned how many others are impacted by MS.

Support BikeMS 2015This year I’m stepping up the distance to ride 120 miles over 2 days including a spectacular route over the Golden Gate Bridge and up the coast before heading into Sonoma. I also am captaining my own team in an effort to rally other folks at Comcast to join the hundreds of other Comcasters around the country that also ride for their own fitness and this cause.

Now for how you can help… 🙂 You’re support will go toward treatment and cutting-edge research to both stop and reverse the damage done to the nervous system by this disease. Three ways:

  1. Make a tax-deductible donation to Bike MS.
  2. Investigate if your employer offers a matching program.
  3. Want to ride yourself? Join my team.

Finally, I would like to thank each of you who have supported me in years past. God bless you!


I’m riding to help end MS and need your support


I’m doing a 2-day 90 mile bike ride (Sept 20-21) for the second year to support an end to multiple sclerosis (MS). I am riding with and in support of my son’s godfather who was diagnosed about 6 years ago. 

Generous donations from people like you last year helped me raise $2,800 which combined with other riders came to over $2M to help in research and treatment!

You can help by sponsoring me today thru a tax deductible donation.


Update Aug 18, 2014: I reached my $3,000 fundraising goal! Going to stretch to $4,000…


I’m riding to put and end to MS. Support my team.

bike_trainingcrew_bannerHi Friends and Family,
I’m doing a 2-day bike ride (Sept 21-22) to help end multiple sclerosis (MS). I decided to ride with and in support of my son’s godfather who was diagnosed a few years ago. If you are familiar with MS you know that while there are treatments available to try and slow the disease their effectiveness is sporadic and there is no cure .

If you can sponsor me and my team in this ride, your donation will go toward treatment and cutting-edge research to both stop and reverse the damage done to the nervous system by this disease. Ways you can help:

  1. Make a tax-deductible donation to Bike MS.
  2. Investigate if your employer offers a matching program.
  3. Share this link with someone else that might be able to help.

If you can’t help financially now, maybe you’re a cycler and you can offer me some advice before I hit the road for 90 miles. Thanks! 🙂

UPDATE: Thanks to all who supported me in 2013! We raised over $2,800, which with the rest of the riders that weekend, contributed $2 million to research and treatment of MS!

How to miss a childhood

As a father of three, I was deeply moved by this mother’s reflection on a note she got from this day care provider…

I can recall a time when you were out with your children you were really with them. You engaged in a back and forth dialog even if they were pre-verbal. You said, ‘Look at the bus, see the doggie, etc.’ Now I see you on the phone, pushing your kids on the swings while distracted by your devices. You think you are spending time with them but you are not present really. When I see you pick up your kids at day care while you’re on the phone, it breaks my heart. They hear your adult conversations. What do they overhear? What is the message they receive? I am not important; I am not important.

I can remember back when I first got a smartphone and my oldest was just a baby. I thought then about how I didn’t want to be one of those parents that was so immersed in my phone that I was not present with my children. We banned phones while eating as a family and I always kept my phone in the other room at night.

However as the years have passed, I can identify with too many of the situations observed by this mother and think I need to take a renewed approach to being present. One exercise that helped was imagining my little kids as teenagers at a time when I very much want to talk and interact with them… yet they were too distracted by their own devices. I would hate to feel that we didn’t set a good example of how to be human and how to be present.

How I organize my personal finances

Maia Garau recently visited eBay as part of our “principal in residence” program and discussed with us the growing field of service design (which she teaches at RISD). My favorite line she quoted was from the Economist which defined a service as “…anything you can’t drop on your foot.”

It got me to thinking about some great end-to-end “services” that I use to manage my finances and yet what’s still missing.

Bill Management

I hate getting bills in the mail and my wife hates how they clutter up our house. So when we were first married I didn’t want to look at the bills and she’d stuff them away out of site–not a good combo for our FICO score.

logo-paytrustThen I discovered Paytrust which goes far beyond the other bill payment services available in that they actually receive your bills. When you sign up Paytrust, they give you a personal PO Box in Sioux Falls which you use as your mailing address meaning for example my PG&E (power & gas) bill gets mails to them and not my home. They scan, OCR, and post the bill online as a PDF with all the appropriate metadata (amount due, due date, etc). Bill payment is easy either by EFT or by having Paytrust mail a check on your behalf (meaning I can even pay my gardener and dentist).

There are several benefits to having Paytrust handle your bills this way:

  • It’s safer as you don’t have to worry about someone stealing bills out of your mailbox (and you don’t have to worry about organizing and storing them).
  • It’s a great papertrail. I can’t tell you how many arguments I’ve won with Customer Service agents over the years since I know exactly when I paid each bill and for how much.
  • They mail you a DVD at the end of each year with all your bills PDF’d for your tax records.
  • Whether I’m at work or at home or my wife wants to view the bills–we can do it from anywhere.

You can tell that this service was thought thru E2E from bill receipt, to payment, to auditing later–which sets it apart from the competition. The only drawbacks is that the service costs $12.95/mth (vs. many banks offer pure payment services for free) and Intuit (who bought Paytrust about 5 years ago) hasn’t made any major improvements in a few years–but at least they haven’t messed it up. 🙂

Daily Account Monitoring

As a big Scott Cook fan, I always wanted to love Quicken over the years but just never did. It always felt like work to keep it’s register in sync with all my accounts and payments. It also didn’t help me during the week when I wanted to know just how much money I had at any given moment and what was coming in and going out.

Mint Money ManagementThen a few years ago a board member for Mint visited a class of mine at Berkeley as a guest speaker. I tried the service out the next day and have really been pleased with it ever since. Since it’s a web service, it’s always up-to-date, synced with my accounts and I can access it from anywhere. It alerts you if you have any irregular behavior such as large deposits or withdrawls. It leverages crowd sourcing to learn how to better categorize transactions. However my favorite feature is how it learns over time what you usually spent in a given category and establishes a “budget” for that amount (letting you know if you’re over or under it later).

Finally the Mint iPhone App connects me to this rich set of data on a daily basis in a simple way. Of course it could be improved such as I’d like to be able to dig into changes in my 401K (chart of how it’s trending, which holdings are up/down), be able to re-categorize transactions, and “predict” my cash flow out a couple months based on past data and budgets.

Quarterly Lookbacks

Download Excel Financial StatementI read Rich Dad, Poor Dad around 2001 and quickly understood the value of regularly assessing our income/expenses and balance sheet. Yet nothing at the time met my needs (Quicken, MS Money, etc) so I looked to Excel to do the work for me in the way that I found most intuitive. It puts all of our monthly income and expenses, assets and liabilities onto one sheet of paper. Simple, visual, straightforward. We update it every 3 months and graph our progress over time.

Download Financial Statement Template
[MS Excel XLS – 194KB]

I imagine that perhaps someday, Mint could replace this manual aspect of my E2E experience but just not yet–however it does make filling out the statement way easier.

In summary I have incredible brand loyalty to both Paytrust and Mint due to their well thought out service design (I’m a NPS promoter) and see how powerful a differentiator it can be in what is a crowded field.

What services do you find most useful and why?

Update 9/14: With Intuit acquiring Mint they now own two of the services I mentioned above. I hope they do a better job continuing development of Mint than they have done with Paytrust and would love an integration of the two services. If anyone on those teams would like to chat I’ve got a number of ideas… 🙂

How I triage email using color

Let’s face it, many of us now receive more email that we can read. So if we’re not reading all our email, are we at least reading the most important messages? If you haven’t customized your email client, I doubt it.

Most major email clients (e.g. Outlook) treat all messages the same and sort by time stamp. Unread messages are typically shown in bold. Here’s an example inbox:

Standard Email Inbox

Notice in this example, there are some messages which are more important than others. For example Jill Executive (presumably a big shot at the company) is asking about some super important presentation coming up. And my wife apparently needs me to pickup the baby, also very important :). Yet the emails from David Shah were automatically generated when he created the projects and not critical to read.

Now, I know many of you are thinking… well Preston, why don’t you setup some filters and have some of those messages moved to folders. I’ve experimented with those but I always end up “losing” a message which was not filtered the way I had intended. Also, as with all hierarchical organization schemes, finding the messages later in folders can be challenging. Some of you may also have some other nifty email program which you’ve found to be better—but those of us in Corporate America are stuck with Outlook (at least for the time being).

About a year ago, I stumbled upon a new way to deal with this problem using a little known feature within Outlook which can automatically color messages based upon certain rules you setup. By doing this you can make less important emails appear less noticible and more important emails stand out. Here’s an example:

Triaged Email Inbox

Notice how an inbox of 8 messages at quick glance looks like just 4 messages. Amazing! In this way the likely most important messages will be most visible in your inbox whereas the less important ones you more likely don’t need to respond to will fade into the background.

Here’s how it works from within Outlook 2003. Click on Tools—>Organize from the menu.

Click on “Using Colors” and then on “Automatic Formatting”. Here are the rules I setup (in this order as they’re run sequentially):

  • Condition: Where I am on the CC line
    Font: Grey
  • Condition: Where I am the only person on the TO line
    Font: Blue
  • Condition: Where I am on the TO line with other people
    Font: Green
  • Condition: From: <My Manager’s Name>, <Executives Name> Where I am on the To: line with other people
    Font: Red

Note that this system works best in an environment where people appropriately use the TO and CC lines. You should always put a person on the TO line if they need to respond and the CC line if its simply to inform.

Archiving and Finding Messages

I’ve found the color system to work well with my archiving and search system I’ve setup. I have a daily auto-archive setup on my inbox to archive anything older than 14 days to a file for that quarter. In this way each archive file does not get too big. Then I have all my archive PST files open in Outlook which allows Windows Desktop Search to index all the messages. If you haven’t tried Windows Desktop Search, it’s based on the one in Vista but available to install on Windows XP for free. You can even do complex queries like “date:last week” and “status from:John Doe”.

If you’ve found other interesting ways to organize and triage email, let me know.