Being a Strategic Leader Is About Asking the Right Questions

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Guest Post by Lisa Lai

Originally posted in the Harvard Business Review.

If you asked the world’s most successful business leaders what it means to “be strategic,” how many different answers do you think you’d get? Consider this number: 115,800,000. It’s the number of unique links returned when I searched online for “strategic leadership.”

There’s a good reason for all of those links: Strategy is complex. Thought leaders from all over the world have created sophisticated frameworks designed to help leaders grapple with their own strategies at an abstract level. But the reality is that strategy succeeds or fails based on how well leaders at every level of an organization integrate strategic thinking into day-to-day operations. This is less about complexity and more about practical focus.

How can you personally be more strategic as a leader? Consider asking yourself and your team the five questions below to drive clarity, alignment, and strategic insight. The questions build on one another, leading to a well-aligned, strategic perspective. If you make these five questions part of your ongoing dialog, you will inevitably become more strategic and more successful as a team.

1. What are we doing today?

Leaders are often surprised at just how much they don’t know about what team members are working on. Here’s why: Over time, organizations add more and more to the plates of various teams and employees. While leaders and team members talk at length about new initiatives and assignments, they focus less on legacy work that’s still being done. At some point leaders lose sight of just how much time people are investing in legacy priorities. Asking this question almost always brings to light significant work that managers aren’t aware is being done or that’s taking much more time than it should. You can’t move your team forward strategically without knowing the answer to this question with total clarity.

2. Why are you doing the work you’re doing? Why now?

Once you’ve taken stock of all the work being done by your team, the next logical step is to examine the importance of the work being done. This serves two strategic purposes. First, you gain clarity on what’s important and why it’s important from your team’s perspective. You’ll likely uncover situations where you and your team are uncertain or in disagreement. This drives important conversations with your team about choices, resources, and trade-offs. Second, you have the opportunity to attach value and meaning to the work being done by your team. Everyone wants to believe that the work they do matters. It’s your job to understand and articulate that with your own team and across the organization. The only way you get there is with scrutiny.

3. How does what we’re doing today align with the bigger picture?

Never underestimate the power of gaining total clarity about your own area of responsibility and then examining how well your work aligns with the broader goals of the organization. This is a discussion about gaps and outliers. If your team is working on something that doesn’t align with the broader purpose or goals of the organization, you have a responsibility to challenge the value of doing that work. This is true even if your team believes the work is important or meaningful. Does it bring value to your customers? Does it contribute to the highest priorities of the business? Work that benefits both your customers and your business should be the top priority. If you identify gaps not currently being addressed, more strategic discussion is needed. Are you doing exactly, and only, what most benefits your organization?

4. What does success look like for our team?

Chances are that you have a handful of measures that others use to evaluate your success. Do they tell the story of what success really looks like for your team? If you asked your team what success looks like for them individually and for the team overall, could they articulate an answer? The best strategic thinkers invest time here — not in trying to pacify their boss with a few measures that can readily be achieved, but in trying to understand what really drives success in terms of activities, behaviors, relationships, and strategic outcomes. The better you are able to align your team around a strong vision of success, the more likely you are to achieve it.

5. What else could we do to achieve more, better, faster?

Most leaders want to demonstrate their ability to “be strategic” by jumping directly to this question. If you haven’t done the work to answer the preceding questions, it almost doesn’t matter what you come up with here, because you may or may not be able to act on it. But if you do the work to answer the preceding questions, you are well positioned to be strategic in answering this one. You may identify new and better ways to serve the broader goals of your company. You may choose to redirect resources from current work that matters less in relative importance when compared to other new possibilities. This question is the most important of the five; every great leader needs to challenge their team to do more, better, or faster over time. It is, however, inextricably linked to the previous questions if you want to generate the best strategic insights.

The bottom line:

Being a strategic leader is about asking the right questions and driving the right dialog with your team. In doing so, you raise the team’s collective ability to be strategic. The more competent you become in asking these questions, the better positioned you are to drive progress for your team and your organization.

Lisa Lai serves as an adviser, consultant, and coach for some of the world’s most successful leaders and companies. She is also a moderator of global leadership development programs for Harvard Business School Publishing. Follow her on Facebook, Twitter, her Blog, or her website @ LaiVentures.com.

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