Whenever I begin a new exercise program, I feel great and wonder why I waited so long to start. It\u2019s the same way with strategic planning. We all feel better when we are strategically fit. Unfortunately, as with physical exercise, a million little daily demands often keep us from doing what\u2019s best for our long-term career health. A lot of my executive coaching clients use me as their personal trainer for strategic planning. They could do strategy without me, but they want to do it right with the least amount of effort. I always start with a fitness assessment. To determine if you are strategically fit, ask yourself these questions.\n\n Does your strategy address the why and the what questions?that is, the business rationale and the applications plan\u2014as well as the how and the who questions\u2014that is, the technology and organizational elements? There are a lot of grand ideas without the legs to make them happen. Conversely, a lot of people draw up tactical to-do lists without the raison d\u2019\u00bftre. Make sure you cover all the bases.\n Can your strategy be summarized in a few sentences? A health-care executive recently told me, "I think I have a strategy; I\u2019m just unable to articulate it." If you can\u2019t pitch it, you don\u2019t have it. \n Are the benefits articulated as well as the costs are? A lot of strategic plans I review have entire appendixes dedicated to costs, while the benefits are bullet points listed on a single page. The value proposition should be as detailed as the costs. \n Do you have an implementation plan backed up with the money and resources to realize it? Can you measure and monitor success?\nBy definition, a good strategy gets implemented. That means you need commitment from all of your stakeholders. Many IT executives assume that their stakeholders are the same people for all strategic dimensions. It\u2019s not so. For the why and what questions, your stakeholders are your business counterparts and the people who help them think about IT. For the how and who questions, the primary stakeholders are your direct reports within the IS organization. The how and who strategies are driven by the why and what strategies. If you try to get your business counterparts to participate in the how and who questions, you will bore them senseless.\nIf your answers to the those questions uncover some weaknesses in your planning, you can use a strategy process that I recommend for my clients. I have adapted it from a Harvard Business Review article titled "Making Strategy: Learning by Doing" (November-December 1997) by Harvard Business School Professor Clayton M. Christensen.Step 1: Assess your current positioning. Do a classical SWOT (strengths, weaknesses, opportunities and threats) analysis of your department\u2019s state of affairs. Get your stakeholders to pick the top five issues and opportunities for further analysis.Step 2: Analyze the top issues or opportunities to identify the forces that are driving them. Ask "why" five times until you get to the underlying causes. At this point you will have five to 20 root causes. Ask your stakeholders to pick the one or two most important root causes. Write "driving force statements" (see Christensen\u2019s article for examples).Step 3: Define your objectives and measurements for each root cause. Step 4: Identify two or three actions that would best address each root cause and further your objectives and measurements. These are your strategies. Document them using Christensen\u2019s strategy matrix.Step 5: Define a project-based implementation plan with assignments and resource requirements for the next year. Christensen says that an outside facilitator can help a management team work through these steps in a few intense days. If you are new to strategic planning, you probably won\u2019t feel comfortable asking senior executives to give you three full days offsite. Do the best you can. You don\u2019t have to be brilliant to generate a great strategy. Strategy is a guess about the future, tested in real-time and iterative in nature. It\u2019s a process, not a project. And as Christensen says, a good strategy-making process will do a lot to improve your ability to think strategically.