APPENDIX A

Questions to Inspire Strategic Thinking

To be an effective strategic thinker, you must regularly ask questions—both of yourself and others—to better understand how your work fits into your company’s big-picture objectives and the competitive forces in your industry. The following questions are drawn from the chapters of this book and are grouped together according to specific situations or problems you may face. By regularly referring to this list, you’ll be able to see challenges from new angles and shape your work to maximize your contribution while better aligning your team with organizational goals.

Understand Your Organization’s Strategy

What’s our strategy—and my role in executing it?

Reflect on these questions yourself and reach out to others in your organization—including your boss, peers, and employees—to better understand your company’s strategic objectives.

• What are the company’s major strategic objectives right now?
• What is our company already great at?
• What are the major needs, challenges, and opportunities we’re facing over the next six months? Year? In the long term?
• How does my team fit into this picture?
• What are the top priorities for my group? What are the big needs, challenges, and opportunities that we should tackle in the next six months? Year? In the long term?
• What role should I play in carrying out this strategy?
• What are the major needs, challenges, and opportunities I should take on in the next six months? Year? In the long term?
• What are my boss’s and colleagues’ major objectives right now within the organization? How can I support them?
• What is the strategic intent of the leaders at the level above mine?
• What are the key choices that I make in my jurisdiction?
• With what strategic logic can I align those choices with those above me?
• How can I communicate the logic of my strategy choices to those who report to me?

What are the risks to our strategy—and to me?

Considering strategic objectives, ask yourself where the biggest risks are for your team and your own professional life.

• What are the major sources of uncertainty in my team’s future?
• What are the external risks (for example, funding, competition with other units, potential reorganization)?
• What are the internal risks (for example, personnel changes, team dynamics, office politics)?
• What are the major sources of uncertainty in my own future?
• What are the professional risks to my success (for example, professional goals; experience, training, and accreditation; work logistics)?
• What are the personal risks to my success (for example, health, family, finances)?

Develop a Big-Picture Perspective

What is the purpose and role of my organization?

Reflect on these questions regularly, so you’re keeping organizational priorities front of mind.

• Why does the organization exist, and what is its purpose?
• If the organization didn’t exist, what difference would it make to the world? What would be missing?
• What does the organization offer our customers—and what does it not? How and why does this offering deliver value to these customers?
• What does this offering produce for the business and for shareholders?
• How do the people within the organization behave—toward customers, other stakeholders, and each other?

Who are my organization’s key stakeholders?

Brainstorm a list of people your company serves. Then answer these questions about each one to narrow down your list into a focused group of stakeholders.

• Does the stakeholder have a fundamental impact on the organization’s performance? (Required response: Yes)
• Can we clearly identify what we want from the stakeholder? (Required response: Yes)
• Is the relationship dynamic—that is, do we want it to grow? (Required response: Yes)
• Can the organization exist without or easily replace the stakeholder? (Required response: No)
• Has the stakeholder already been identified through another relationship? (Required response: No)

Where are opportunities for change in my organization?

Interview or survey your colleagues to better understand their fundamental beliefs and assumptions about your company’s current situation. Use their answers to identify areas that could be changed.

• What are some key assumptions inherent in your day-to-day activities—the established “rules” under which the organization generally operates? What core values are “givens”?
• What are some of your own beliefs about the organization? What makes it perform effectively at present? In what areas does the organization devote too much—or too little—time and resources?
• What is the organization’s competitive space? Are there ways it might be redefined?

What trends are happening inside my company?

Use these questions about your company’s people, processes, products, and strategy to note any early signals of change.

• Have there been any new hires or departures of key employees in the company? Has there been an increase in external hires?
• Have there been important changes in relationships and power dynamics that could impact my and my team’s efforts?
• Are my employees engaged? How might that impact the speed and quality of my and my department’s initiatives?
• What key process or technology changes are occurring in other departments?
• Are there patterns in the types of requests I am receiving from key stakeholders? What might these requests signal?
• Has my team experienced a change in the service they receive from internal colleagues?
• How might the introduction of a new product, service, or geography by my company impact my line of business? Does a series of new products signal a change in direction?
• Are there signals that a drop in sales of a key product might be due to internal factors?
• Does a series of acquisitions signal a new direction for the organization?
• Are there changes in resource allocation across the company?
• Are there signals that stakeholder priorities have changed?
• Given all these trends, what do these changes signal for my department or my own work?

Align Decisions with Strategic Objectives

How do I make a strategic decision?

When faced with a tough issue or problem, the following questions will help you understand the impact of your choice.

• What preexisting company goals or priorities will be affected by the decision?
• What are realistic alternatives to the choice I’m facing?
• What are the pros and cons of each alternative?
• What important information am I missing?
• What are the potential short- and long-term ramifications of my choice? What impact will my decision have one year in the future?
• What perspectives should I consider from stakeholders? What cross-functional considerations should I take into account?
• What trade-offs seem most appropriate to make in this situation?
• Why and how much does the team support my decision?
• (One to two months in the future) How did this decision pan out? Where should I make corrections, and what can I learn from what’s happened?

Set Priorities and Manage Trade-Offs

How do I create a plan to execute multiple goals?

When organizational goals don’t mesh, define a way to meet them by asking these questions.

• Can I work on all of the strategic goals at the same time? If not, what do I need to tackle first?
• Are there resources or knowledge that can be gained from an early opportunity that could help another objective later?
• How much can I and my team do at once? Do we have the resources to focus on more than one major strategic project at a time?
• What will it take to keep the current business going while we are driving new strategic initiatives?
• Do I have people in place that have the skills and know-how to move into new strategic territory?
• Will I need to hire new people or train existing staff? What’s the extent of this investment, and how will it be integrated with the current team?
• If the market or our resources change during planning, should our original assumptions about how to compete still prevail?
• Have our investigations suggested specific learnings that would substantially alter those assumptions?
• Are there serious disagreements between key stakeholders about executing the strategy? What’s the root cause of the opposition?
• Are skeptical colleagues raising legitimate concerns that might call for refashioning the way forward?

Align Your Team Around Strategy Goals

What key objectives should my team be focusing on?

Define your most important work with your team and align them toward it.

• Will success in this outcome drive the mission of the larger organization?
• Is it supporting, and supported by, our primary business goals?
• Will achieving it make a statement to the organization about what’s most important?
• Will it lead to the execution of our strategy?
• Is it the appropriate stretch?
• Are we excited about it? Do we have an emotional connection to it?

How can I inspire strategic thinking in my team?

Ask your team these questions to drive clarity, alignment, and strategic insight.

• What are we doing today?
• Why are we doing the work we’re doing? Why now?
• How does what we’re doing today align with the bigger picture?
• What does success look like for our team?
• What else could we do to achieve more, better, faster?
• How are we doing things differently than our competitors?
• What methods should we use to find out more about industry trends and innovations?

How do I communicate a vision to my team?

When the strategy changes, carefully consider how you’ll communicate the change by thinking about each of these questions.

• What does my team care most about? What do they know about the current status of our project, goal, or bigger strategy? How do they feel about the team and organization right now, and what are they expecting?
• How is the vision relevant to them? How would they challenge the vision? What would make them resistant?
• What are specific, measurable goals and deadlines? How can I help my team achieve them?
• How will they benefit in the end? What problems am I trying to solve that will make their lives better in some way?