Failure to Win, or Winning Failure?

Once again I find myself sitting here in one of the many cafeterias at Microsoft. This time I have "ditched" the office for a quiet place to work — as an escape from the drop-in conversations and intravenous connections to email and instant messaging — to sit and think, and hopefully complete some key deliverables that have been piling up this week. It’s been a productive week, but I’m in a new role on a new team, and on top of learning the new acronyms and getting caught up with the rhythm of the business, I feel like I’m still trying to catch up from a 3-day training class last week. So after a great dim sum lunch with my friend Mike and a quick stop at the music store to covet some gadgets that I can neither afford nor justify to the wife, I came here to get some work done.

And then I noticed the carpet. Yikes. I know its been down for a while now, but I never really stopped to look at it. I think I had a long-collared silk shirt with the same pattern back in 1978. But I digress…

So anyway, after sitting here for a couple hours, my mind keeps going back to something Mike and I talked about at lunch, and I just felt the need to jot something down (and share a picture of really ugly carpet). So here goes:

One of the things I really like about the Microsoft culture is the competitiveness between individuals, between teams, and sometimes even between the various business units. I’ve always been very competitive, and I like how the company uses that to inspire people to reach above and beyond what is expected. The downside of this strategy, of course, is that someone has to lose (or, in a more politically correct description, fail to surpass the achievements of others).

There is absolutely nothing wrong with losing — as long as you can learn from your failure. Seth Godin has a new book out called The Big Dip that documents and celebrates people who quit or have failed, but who learned from their experiences and leveraged that to go on to something bigger and better. And that’s where Microsoft — and most other companies — can improve: get better at the post-failure process.

I don’t have a clear picture of what that process would look like within Microsoft, nor am I the stellar example of entrepreneurial success. I was lucky enough to sell my own startup for enough money to pay back my creditors and vendors, pay off my credit cards, and take my family on a nice vacation. However, I wouldn’t trade my experience — pitching my company to dozens of venture capital and angel investors, constantly tweaking my business model to every bit of feedback, and making any adjustments I felt were necessary to move my business forward — for anything. Spending 3.5 years in the startup trenches was the best things I could have done for my career. And I could have kept pushing the company along, partnering instead of selling — but I saw that other companies in our space were closer to the end goal, more agile, and better funded, and so made the decision to accept the offer to sell the company.

Sometimes companies come to this same crossroads and follow this same path. Not often enough. How many times do companies race to be the poster-child for Innovators Dilemma before they recognize failure and do the right thing — to stop, assess what they have learned, and try a different direction? What would the post-failure process look like? I suppose that the first step is getting businesses and entrepreneurs — and middle managers — to agree that it is ok to fail. Seth is doing his best to sell that concept. Hopefully his next book will touch on life after failure, and how to learn from it. I’ll have to do some more thinking on this and come up with a basic post-failure workflow….

Christian Buckley

Christian is a Microsoft Regional Director and Office Servers and Services MVP, the Founder & CEO of CollabTalk LLC, an independent research and technical marketing services firm based in Salt Lake City, Utah, and CMO of, a blockchain-based video technology company.