The patterns of day-to-day life are very different in a startup.
At Microsoft, the sheer size of the organization builds a set of nearly automatic patterns, with constant demands for attention to specific projects and specific teams, and recurring requirements like quarterly financial statements, preparation for quarterly business reviews, monitoring and guidance of execution both locally at corporate headquarters and in worldwide subsidiaries. The challenge was not in determining what will get done but how to compress my schedule and manage my team more effectively by teaching and encouraging, rather than directing and demanding. With a full-time administrative assistant and a business manager (Microsoft’s equivalent of a chief-of-staff), more than 70% of my time was effectively directed by the undeniable needs of the business.
Running a team of 120 people in 80 countries in a company of 91,000 requires not just worldwide timezone awareness, but connection to the corporate and local constituencies that those 80 people need to have on their side. At Microsoft, 120 people is a lean team that must rely on many other organizations in order to execute anything from marketing campaigns to discounts to customer intelligence. These dependencies include corporate and field marketing and sales for multiple channels (direct/enterprise, indirect/enterprise, indirect/midmarket, indirect/small business; direct/government, indirect/telecommunications… the list goes on but you get the point).
Add to this the corporate governance team and process and you begin to see the layers of clockwork required to operate such a massive machine. Political influence and personal connection is the lubricant that lets these gears run, so to be an effective leader you need to be available and involved in the workings of each of these adjacent gears. This translates to understanding their challenges, finding ways to be relevant and helpful, and integrate your needs into their plans so that your goals are truly shared – you could say “adopted” in the context of adopting a child – by these other teams.
This is not much more complex than required – overall the structure at Microsoft is fairly lean for a company of its revenue and profit, and is constantly tuned by an executive who ran operations for Wal-Mart and his outstanding team. It’s just that the problem itself is really hard, and the clock is always running.
Switching to a startup of 65 people (mostly engineers) with a shallow hierarchy and a flat leadership team structure as an individual contributor leading strategy is about as different of a day-to-day experience as I can imagine (apart from not working at all, of course). No forced direction, no gaps between departments (including the fact that some departments are fully represented in a single person) and no mandatory schedule. Seemingly endless expanses of open time on my schedule. Titular responsibility for the company’s strategy.
And what is strategy, really? To me, strategy is a conversation – a conversation shared by all the operational leaders of an organization that accurately reflects the market, a belief in its future shape, and the appropriate actions required to match the company to that future shape. If the conversation is managed correctly, the appropriate actions will show up almost automatically based on how each leader is thinking. So to be effective in a role like this you have to be engaged with the operational leaders, understand and add value to their day-to-day work, and then reflect the company’s beliefs back to itself and to the market. Start with a blank slate, discarding your preconceptions, and go from there. But starting from scratch takes much more effort than keeping pace with an existing flow.
Eight weeks later, I am finally (mostly) adjusted to the changes – from the trivial (managing my own schedule and coordinating with other people’s admins) to the substantial (feeling emotionally satisfied at the end of a week where I didn’t have “important meetings” scheduled every 30 minutes) to the crucial (entering the rhythm of the company and adding value without direct authority).
I’m satisfied with the changes and find that for the most part I’m more lighthearted, more flexible, and softer in style than I was at Microsoft. My family certainly approves. There is a certain “West Wing” feeling of constantly dealing with issues of world-shaking importance that is missing, but in that space I think I’m finding room for more thinking and writing, and interest in other aspects of what’s happening in the software industry and beyond.