We're closing in on midyear career discussions again. It's time to place your hopes and humility in the hands of your hierarchy. I still haven't recovered from the amputation of our midyear ratings, which allowed managers to send messages and employees to salvage careers after a temporary setback. They've been replaced with a time-consuming CareerCompass that contributes complexity and confusion instead of context and clarity.

Eric Aside

CareerCompass is an internal Web application that allows employees to assess their competencies and skills against standards for their career stage. Managers and selected peers can also assess employees through the tool. It's a nice idea, but the first version was a less than ideal implementation.

Don't get me wrong, even though I want the midyear ratings back, I initially found the less confrontational career conversations to be, well … constructive. Unfortunately, though HR and managers may mean well, their advice is often cryptic. Take the biggest offender: strategic insight. The common conundrum: "My boss says I should think more strategically. What on earth does that mean? What should I do?"

Good question. Ask your favorite manager or executive about improving your strategic insight, and he or she will likely suggest getting more involved in planning, focusing on the vision, thinking more about the business, and other such well-meaning nonsense. Yes, strategy happens in those activities, but attending a pro football game doesn't make you a great quarterback.

Strategy is not an activity; it's a way of thinking. It happens anytime, not just during planning. If you want to get better at it, wasting more time in meetings isn't likely to help. You need to mature your way of looking at work and the world. You're not an ignorant waif anymore. It's time to wake up and grow up.

Blind Faith or Cowboy Junkies?

A friend was recently comparing two coworkers to me—a guy who did whatever he liked and a gal who followed the current business strategy. My friend said, "[The gal] is a better strategic thinker." No, she's not. Neither is thinking strategically at all. The guy is a cowboy without a herd. The gal is tactically contributing to a given strategy, which is far better, but is not strategic insight.

There's a growth curve for strategic insight. Take a look and see where you fail, I mean, fall:

§  Ignoring strategy: The self-centered cowboy

§  Following strategy: The tactical contributor

§  Questioning strategy: The strategic tactician

§  Evolving strategy: The strategic thinker

§  Determining strategy: The strategic leader

Let's break these down, examine the pitfalls of each level, and discover how you make progress up the curve.

Yippee-ki-yay, project buster!

The self-centered cowboy ignores strategy, considering it bureaucratic mumbo-jumbo that might otherwise prevent him from creating cool innovative products. His heroes are the storied rebels that broke the rules and created the killer features that vaulted them to the principal and partner levels. Oh, to be that bold and bright!

Eric Aside

The principal and partner levels are among the most senior at Microsoft. I know a number of these heroes to cowboys, and none of them ignored strategy. They ignored middle managers who took the strategy too literally instead of truly understanding the intent. The rebels did the right strategic work and were rewarded for it by upper management. The moral of the story is, "Make sure you deeply understand the strategy before you start messing around."

Yeah, right. Never mind what the actual facts might be in those stories; we're not a startup anymore, and most cowboys aren't working on incubation efforts. They are working on established products and services, and cowboys in the big city will get lost and ignored no matter how well they rope or play guitar.

Why do cowboys get lost and ignored on big projects? Because their individual actions are like random noise. Without coordination, each cowboy's efforts cancel out the others. Their features may be cool in isolation, but they don't fit into a larger whole. Thus, no one sees them, no one uses them, and they add no value.

What's worse, all the random features created by cowboys only confuse customers more. They actually do more harm than good. A cowboy, setting out on his own to change the world, is only setting himself up for disappointment. Not because he doesn't have good ideas or because the big city won't give him a chance. A cowboy fails because he doesn't organize with others to drive the product forward.

Resistance is futile

The tactical contributor follows strategy, trusting the plans of the collective and finding creative ways to bring those plans to life. Many cowboys feel that tactical contributors have cowardly relinquished their freedom for the safety of the collective, with a "baaaa" and a "moo" for good measure. However, the real reason for being a tactical contributor is usually one of the following:

§  "I'm not interested in the responsibility of deciding strategy." As I talked about in "When the journey is the destination," not everyone wants to become a VP or Technical Fellow. Some are happy to make their valuable personal contribution, and then spend time focused on their other interests. Understanding and following the current strategy is the best way to have significant individual impact.

§  "I'm not prepared to take responsibility for deciding strategy." For those who aspire to lead technically or organizationally, to expand their impact beyond themselves, they need a place to start. Even if you disagree with the current strategy, your smartest initial move is to learn it and follow it. Only fools try to fight or evolve something they don't understand, repeating past failures. Intelligent people seek first to understand the strengths and weaknesses of the current strategy before they change it.

Following the current strategy doesn't mean giving up original thinking or creativity. It's actually quite the opposite. Many of the world's greatest buildings and works of art were inspired by the constraints of the land or medium in which they were made. Finding ingenious and beautiful designs that meet a fixed set of requirements is a challenge that great minds delight in solving.

Tactical contributors are highly valuable employees, but they aren't quite ready to make the leap to strategic thinker. Before they can determine new strategy, they must learn to constructively question the current strategy.

Is that right?

The strategic tactician questions strategy, while still following it. This is not to be confused with idiots who complain about everything without providing any constructive alternative. The strategic tactician is still tactically following the strategy and wants to see it succeed. She simply knows enough and thinks enough about the strategy to question assumptions and approaches that seem suspect.

Some people are afraid to take this step. They don't want to seem like troublemakers, and they trust that decision makers know what's best. For the bashful out there, here are a few facts that might get you to the strategic-tactician level:

§  Decision makers are absurdly imperfect, just like the rest of us. They don't always have the right or complete information. They can be blindsided by their own biases. They might even be incompetent, though Microsoft has some real talent in these ranks.

§  Troublemakers aren't thoughtful. There's a big difference between thoughtful questions and annoying questions. If you ask a question you could have easily answered yourself, or you complain for the sake of complaining, you are being annoying and causing trouble. However, if you've thought about a situation carefully, and truly care about getting things right, you aren't causing trouble. You are pointing out areas that need a better explanation or potentially a change in direction. Most decision makers will thank you for your input and think well of you at the next review. If yours doesn't, perhaps it's time to switch projects.

§  The current situation is constantly changing. When the strategy was devised, it was based on what people knew at the time. Today is different. New issues come up. The market, technology, competition, and customers change. Leadership changes. Requirements change, sometimes in subtle ways. All these changes can cause the current strategy to become inadequate or inappropriate. It's your job to notice, check if the strategy still makes sense, and question it if it doesn't.

So how do you notice when to question the strategy? When your gut stops you and asks, "Wait, why are we doing this?" At that point, get the answer. Ask your friends and coworkers, "Why?" Keep asking till you either get a good explanation or have no recourse but to question the decision makers. They will remember you as a strategic thinker, not a troublemaker. Does that mean you are a strategic thinker? Not quite, but you are ready to make the leap.

I suggest a new strategy

The strategic thinker evolves strategy, adjusting it to account for changing conditions or gaps in approach. The big leap to strategic thinker is that strategic tacticians point out issues, but strategic thinkers resolve them. A strategic tactician brings up a problem with her manager, but a strategic thinker also lays out a practical plan to resolve the problem that fits within the current strategy.

In many ways, it's really not a big jump between strategic tactician and strategic thinker. You just must be willing to take responsibility for change, instead of leaving it to someone else.

Often people confuse strategic thinking with breaking the rules or making up your own rules. That's cowboy talk. A strategic thinker evolves the current strategy, coming up with resolutions that stay within its spirit, but expand or adjust it. That's why the tactical contributor stage of truly understanding the strategy and applying it is so important.

As a strategic thinker matures, he will start generalizing the strategy, evolving and expanding its impact. For example, say his team is suffering because they aren't documenting their interfaces sufficiently to comply with regulations. It's much faster and easier to document them from the start, especially with tool support, but no one is in the habit.

A freshman strategic thinker might propose adopting Sandcastle for documenting his team's managed code. A sophomore strategic thinker might add Sandcastle to the product-line build. A junior strategic thinker might add documentation completion statistics to build reports and quality gates. A senior strategic thinker might establish his Sandcastle build and report solutions internally on CodeBox or externally on CodePlex, and encourage his network to adopt the solution across Microsoft. A senior strategic thinker is one small step away from being a strategic leader.

I am not a leader of men

The strategic leader determines strategy for her group, her division, or perhaps even for the company. The difference between a strategic thinker and a strategic leader is that the leader defines strategy for whole new areas. While you can become a strategic leader on your own, it helps to have existing leadership sponsor your ideas.

Eric Aside

You don't need to be a manager to be a strategic leader. Architects are strategic leaders. Designers are strategic leaders. Experts who work out the next great approach to security, performance, or reliability are strategic leaders. It's an approach and mindset more than a role.

Often this can be done by circulating white papers with new strategic ideas, creating grassroots community around your plans, or taking on leadership roles within your network. However, you must be prepared to lead the effort to bring your strategy to life. When it's your idea, it becomes your responsibility to see it through.

Anyone can become a strategic leader, though not everyone may want that responsibility. The key is to not focus on yourself and your interests; they are too narrow and won't engage others to join you. Instead, focus on the interests of your customers, your group, your company, and the world. How can they be better served with the capability and resources we have to apply?

It's so easy to go after your own pet project, but you'd be putting on cowboy boots. Being an inspirational leader means walking in someone else's shoes, and serving their needs for a greater purpose. Remember that and you may become a great leader indeed.