One of the questions I’m initially asked by a new strategic planning client is, “How will we know what we’re supposed to focus on with our new plan?” Well, the easy answer is, “You’ll focus on what you need to focus on,” but the more appropriate answer is, “You’ll focus on what your answers to some critical questions tell you to focus on.” Now you may be thinking, “Those sound like a couple of non-answers and they don’t sound strategic at all.” In reality, my ‘appropriate’ answer is what enables you to think and plan strategically. The questions you do or don’t ask prior to and during your strategic planning process will determine if you create a plan that will actually guide you to a stronger future or a plan that won’t.

The questions you do or don’t ask prior to and during your strategic planning process will determine if you create a plan that will actually guide you to a stronger future or a plan that won’t.

One of the activities I’ll often do during a strategic planning retreat or planning session to get a group to start thinking strategically is called Peeling the Onion. It’s simply an exercise that causes the planning team to ask probing questions about themselves, their current and planned future strategies, customers, stakeholders, markets, products, operations, systems, processes, procedures, culture, etc. As the team probes and asks deeper questions, like peeling an onion, the more they probe and peel away current beliefs, the more painful it becomes because some of the answers are personally hurtful or revealing. As a result, there may be a few teary-eyes as people become defensive and territorial. However, the team’s answers to the tough questions spurs deeper, more strategic thinking and insights into what needs to change, what needs to stop, what needs to start, what needs to be accomplished, and who needs to be involved and who doesn’t.

The team’s answers to the tough questions spurs deeper, more strategic thinking and insights into what needs to change, what needs to stop, what needs to start, what needs to be accomplished, and who needs to be involved and who doesn’t.

Here are some of my favorite tough questions to help my clients think strategically:

• What will your ideal customers be asking of you 3-5 years from now? Why? What’s happening in their worlds to cause this?
• What are you trying to achieve / will you achieve by doing X?
• What happens if you don’t do anything about X now?
• Why is this / X an issue now?
• Who brought this forward and why do they care? What impact does this have on them?
• What are the short and long-term benefits of doing X?
• What are the short and long-term ‘costs’ of doing X?
• Who are the stakeholders and who will be most impacted if we do X?
• Who benefits the most and least by doing X?
• Who will be against this decision and why?
• How could you mitigate or respond to their negativity?
• What biases may you have brought / may be bringing to this discussion? Why?
• What is your Plan B and C?
• How will this impact and/or help your team members?
• What needs to happen within your work culture to support your team going forward?

Asking tough questions not only causes you to think deeper and more strategically, it also causes you to rip away what’s no longer working or that won’t help you going forward.

So, go ahead, ask a few tough questions, shed a few tears, and create a plan that will guide you to a stronger tomorrow.

Copyright MMXX – Liz Weber, CMC, CSP – Weber Business Services, LLC – www.WBSLLC.com +1.717.597.8890

Liz supports clients with strategic and succession planning, as well as leadership training and executive coaching. Learn more about Liz on LinkedIn!