Do middling, middle managers run Microsoft? That's the consensus among the former Microsofties who shared their work stories with me over the last couple months. The new work week starts with another Microsoft Confessional -- the fourth in four days -- from 13-year company veteran Boris, which isn't his real name, of course. Boris was smart enough to see the end coming, and he made preparations in the days before his May 2009 layoff. He learned to read middle managers the way a genuine fortune teller might read tea leaves.

People being asked to leave are one view of Microsoft. But those leaving voluntarily are another perspective. In looking at Microsoft, I'm hugely concerned about the departures of two important and long-time Microsoft executives: Mike Nash and Bill Veghte, revealed on February 4 and January 14, respectively. Both men are 19-plus years veterans working for the Windows and Windows Live groups. Nash is headed to Amazon, and Veghte departs following last year's executive shuffle that put Steven Sinfosky in charge of the group (as one of five Microsoft presidents).

Historically, successful shipment of a new Windows version ends with big promotions. Windows Vista was the exception, leading to demotions, sideways transfers and departures (Microsoft wouldn't call them firings). But Windows 7 is a huge success, so what gives with Nash and Veghte  leaving Microsoft?

The departures of Nash, Veghte and also Chris Liddell, Microsoft's former chief financial officer, are canaries in the coal mine. They signal something  fundamentally wrong. Boris' story and the three before it -- "Killed over politics," "Deeply dysfunctional family" and "Poor worker bees" -- offer some insight into what is part of the problem.

Boris' story is the longest of the quartet of confessionals; as such, I've added subheads to make it easier reading. With that introduction, Boris' story:

My career out of college started with working as a technical writer for a few now-defunct engineering software firms. I recall my first day on the job, being assigned a massive Compaq 'portable' as my workstation, and teaching myself MS-DOS and batch file programming via the Compaq's user manual. We had a cool array of hardware around the office for porting: IBM AS/400, Silicon Graphics Iris and Indigo, some of the early Sun SPARCstations, and my favorite, a NeXT Cube.

During the next five years I moved up from a junior writing position to managing an entire department of writers and illustrators. I was largely self-taught as a manager. We made some good hires, got the work done on time, wrote what I still think were some actually helpful manuals, and introduced a bit of publishing innovation with on-demand printing, electronic distribution of documentation on the Web (in 1995!) and CDs, highly modular content, and so on.

In the mid-90's, on a goof, I applied for a job with Microsoft. I was convinced a friend was pulling a fast one when they called for an interview. A month later I was a full-time, blue-badge Microsoft employee.

Through most of my career at Microsoft I worked as an editor of one sort or another, working on both developer and end-user content. In the early years, I was aligned with the Developer Evangelism team and got to work with a really amazing cross-section of smart, influential people in the software industry. Jeff Richter, Don Box, Aaron Skonnard, Charles Petzold, Mark Russinovich -- the list goes on and on.

For a few years I was part of the user assistance team for one of the big orgs, working on UI, help, SDKs, articles, books -- whatever they threw at us. We shipped some very good products and got a lot of recognition in the form of industry awards. I worked on launching a few companywide internal tools and standards projects that made important contributions to the way we build products and communicate with customers. One is still in active use today, almost 7 years after we started. That's a long time in MSFT years. I'm very proud of that since I was a key contributor from the very beginning.

Hamstrung by Ineffective Management

My career trajectory slowed a bit at Microsoft, in part because I mostly worked on small teams and there simply wasn't room for advancement. Also in part because, during the first few years, I didn't understand how the MSFT review and promotion system worked. The reality is quite a bit different from many people's expectations.

It was clear to me at a certain point that Microsoft had turned the corner. There were still a lot of smart people beavering away on various projects, but they were largely hamstrung by multiple levels of largely ineffective management. Who you knew, or how well you could influence those above you, counted more than results.

There were a ton of bozos. Arrogant bozos. Not to suggest that I'm some sort of genius. Far from it. But the intellectual rigor demonstrated by much of the management -- and strategy -- was sadly lacking. In some ways it was funny, but mostly depressing.

The end of the road came in early 2009. Half of my team was let go in the January layoffs. We scrambled forward with vendors for a few months until the remaining editors were canned in May (me included). Out of a starting staff of nearly 20, four remained, all managers. I'm not sure what they manage.

The End -- a Relief

Some of us saw the end coming. I was working on a post-Microsoft business plan, but had envisioned another 12 months of employment for planning and scraping together a bankroll. In the event, on a Thursday afternoon, a friend and I intuited -- partly from sudden, unnanounced travel status of certain managers -- that the end was much closer. Friday we brought in suitcases and took home our personal items. I used my StayFit allowance to buy a gym membership. Monday we printed out any important personal papers. Tuesday we sat down with our GM and got the news.

In my case it was a relief. I wanted to leave many times over the years -- and in fact did once -- but the salary, the benefits and to be honest the good people, too, kept me there. Devil you know. But I walked out the door that day knowing it was for the best and, though it might take a while, I'd come out of the experience OK.

I spent the summer with my family, relaxing, and taking a wider look around the industry. It was much needed, much appreciated time away from the Microsoft hot house. Thanks to the severance package, unemployment and some careful budgeting, we haven't yet needed to dip into our savings. In the longer term we may need to move somewhere less expensive to reduce our housing costs.

Of my former colleagues, only two of us are now employed fulltime in the industry, though at significantly lower compensation. Another seems to have steady consulting work. Clearly the tech publishing industry (including tech writing/editing) has changed significantly, and probably permanently. I don't think the need for communication experts has vanished, but it remains to be seen how we fit into the changing landscape of the industry.

From six to 13 Management Layers

It's a bit hard to equate the different [Microsoft compensation] level systems over the years, but I basically started at what today would be a level 59 and finished a level 61. That's not much of a bump in a dozen or so years. Assume what you will. I know what went down. I know the value of what my team accomplished (we measured it, with business-relevant, industry-relevant metrics). I know what my contribution was to the team. I am more than satisfied that I pulled my weight and more.

When I started at MSFT in 1996, there were six people between me and Bill Gates. In 2009, there were 13 people between me and Steve Ballmer. My inability to climb the corporate ladder cannot alone explain that away. When layoffs hit my team, only the bottom two layers of the org were affected -- the entire bottom layer of individual contributors (ICs) and two first-level managers. Who's working here?

Ironically, I once wanted to climb up that ladder. But I'm glad it never happened. Through friends, I saw the costs: Huge amounts of additional hassle, not a lot of additional pay, effectively no training or support, unbelievable politics, etc.

On the other hand, MSFT philosophy is up or out. Review depends more on managing perception up the chain of command than actual results. (I tested this theory and it's true. I managed a single set of metrics up the management chain, just spinning the results differently depending on who I talked to and what they cared about. The metrics were useless as the tools they came from were broken. Result = promotion.)

There's little or no interest in sustainability. No recognition for doing a job consistently well over time. No incentive for effective cross-team work (unless you can get another team to do work you can take credit for).

Swimming Against Reward-Driven Culture

Interestingly, [internal] MS Poll results show that the ability to work effectively across teams has been consistently one of the lowest-scoring poll items for over a decade. (Yes, I looked it up.) I've seen managers bend over backward to bring a poll score from 75 percent to 80 percent. I've never seen anyone try to address the cross-team problem.

There are good managers at MSFT. I've seen them. There just aren't very many, and they're swimming against an internally focused, reward-driven culture that puts the highest value on visibility.

It can also be very, very difficult to work in a non-engineering role or organization within an engineering-dominated company. Management focus was just on completely different things than what my teams were doing. Successful or not, it was seen as a distraction. Arguably, good management should be able to multitask, look at the world through different lenses, make situation-specific decisions, strategize in a diverse and complicated world. Realistically, that's a rare set of skills.

Long story short, there were many good and bad experiences over the years. The bad stuff made me stronger and more confident in my abilities. The good stuff is work, friendships, and experience I'm still proud of. I know, for a fact, that we helped people. So that's my story. I remain proud of what I did and [I am] hopeful for the future.

Other stories in this series of confessionals:

• 'Killed over politics'
• 'Deeply dysfunctional family'
• 'Poor worker bees'
• Why former employees say Microsoft can't innovate

I'm still collecting stories. Please e-mail joewilcox at live dot com. Stories can be anonymous, but I will need to verify identities.