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Six Key Questions in Strategic Planning

Jan 24, 2019

Whenever you must create or reinvent the direction of your organization, there are six questions, in order, that you must answer correctly. You’ve heard the expression “garbage in, garbage out.” The quality of your thinking and decisions is determined solely by the quality of the information you begin with.

Strategic Questions Examples:

1. Where are you now? What is your current situation? If your business was in trouble and you hired an outside consulting firm to come in to help, the first thing the consultants would do would be to determine your exact levels of sales in every product/service area, the relative profitability of each of your products and services, the trends in each area, the amount of money you have and will have in the foreseeable future, and your position relative to your competition. These are all pieces of information that you can and must generate for yourself.

2. How did you get to where you are today? What were the factors and decisions that led to your current situation? Be your own management consultant. Be prepared to face “the brutal truth,” as Jim Collins calls it, about how you got to where you are today. Refuse to flinch or exaggerate, especially when you have problems with sales and profitability. Jack Welch insisted his managers practice the “reality principle,” which he defined as “being willing to face the world as it is, rather than the way you wish it could be.” You cannot resolve a problem or resolve a difficult situation unless you have the courage to face the current facts squarely whatever they are. Reevaluate all your business activities. Is everything you are doing necessary to win and keep customers? What savings could you generate by partnering with other companies to do work or carry overhead? Could you hare a warehouse or manufacturing plant with a neighboring firm? Can you hare an accounting department? What activities would you outsource without reducing quality or service to your customers?

Download to Learn the 5 Simple Steps for Project Management

3. Where do you want to go from here? What do you want to accomplish? Clearly describe the ideal desired outcome for your business. Project forward five years and imagine that your business was perfect. The greater clarity you have about where you want to be at a specific time in the future, the easier it will be for you to create a great business plan, or blueprint, that will enable you to get from where you are today to where you want to go. Be specific about your future goals and desired outcome. For instance:

4. How do you get from where you are today to where you want to be in the future? What are the steps that you will have to take to create your ideal future business? Make a list. Write down every single thing that you can possibly think of that you would have to do to achieve your goals in the future. 5. What obstacles will you have to overcome? What problems will you have to solve? Of all the problems or obstacles standing between you and your desired future outcomes, what are the biggest or most important? If you weren’t already a fast-growing, highly profitable company, why not? What is holding you back? What are the critical constraints or limiting factors for growth? Sometimes, just identifying and removing one critical block or obstacle can turn your company into a more profitable enterprise. 6. What additional knowledge, skills, or resources will you require to achieve your strategic objectives? What additional competencies or capabilities will you need if you want to lead your field in the years ahead? Every business begins and grows around a set of core competencies, but there are almost always additional core competencies that you’ll need to acquire or develop over time. If your company is already the market leader, then explore what new areas you can excel in. Most of all, ask yourself what you can do, starting today, to begin to achieve those core competencies to create your business of the future.

Ready to take the next step? Take our course in strategic project management to gain the knowledge you need to be a skilled project manager.  This article is excerpted, with permission of the publisher, from Now, Build a Great Business: 7 Ways to Maximize Your Profits in Any Market by Mark Thompson and Brian Tracy. Copyright 2010, Mark Thompson and Brian Tracy. Published by AMACOM. For more information:

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5 Strategy Questions Every Leader Should Make Time For

The best leaders don’t let themselves get too busy to reflect.


Have you ever noticed that when you ask someone in your company, “How are you?” they are more likely to answer “Busy!” than “Very well, thank you”? That is because the norm in most companies is that you are supposed to be very busy – or otherwise at least pretend to be – because otherwise you can’t be all that important. The answers “I am not up to much” and “I have some time on my hands, actually” are not going to do much for your internal status and career.

However, that you are very busy all the time is actually a bit of problem when you are in charge of your company or unit’s strategy, and responsible for organizing it. Because it means that you don’t have much time to think and reflect. And thinking is in fact quite an important activity when it comes to assessing and developing a strategy.

The CEO of a large, global bank once told me: “It is very easy for someone in my position to be very busy all the time. There is always another meeting you really have to attend, and you can fly somewhere else pretty much every other day. However, I feel that that is not what I am paid to do. It is my job to carefully think about our strategy.”

I believe his view is spot-on. And there are other successful business leaders who understand the value of making time to think. Bill Gates, for example, was famous for taking a week off twice a year – spent in a secret waterfront cottage – just to think and reflect deeply about Microsoft and its future without any interruption. Similarly, Warren Buffett has said , “I insist on a lot of time being spent, almost every day, to just sit and think.”

If you can’t find time to think, it probably means that you haven’t organized your firm, unit, or team very well, and you are busy putting out little fires all the time. It also means that you are at risk of leading your company astray.

As famous management professor Henry Mintzberg has described, much of strategy is “ emergent .” It is often not the result of a strategic plan just being implemented, but driven by opportunistic responses to unexpected events. Stuff happens. Companies often engage in new activities – customers, markets, products, and business models – serendipitously, in response to external events and lucky breaks. But this also means that business leaders need to make ample time to reflect on the configuration that has emerged. They need to systematically analyze and carefully think it through, and make adjustments where necessary.

Many leaders don’t make that time – at least not enough of it.

If you are in charge of an organization, force yourself to have regular and long stretches of uninterrupted time just to think things through. When you do so – and you should – here are five guiding questions that could help you reflect on the big picture.

1. What does not fit? Ask yourself, of the various activities and businesses that you have moved into, do they make sense together? Individually, each of them may seem attractive, but can you explain why they would work well together ; why the sum is greater than the parts?

As the late Steve Jobs explained to Apple’s employees when he axed a seemingly attractive business line, “Although micro-cosmically it made sense, macro-cosmically it didn’t add up.” If you can’t explain how the sum is greater than the parts, re-assess its components.

2. What would an outsider do? Firms often suffer from legacy products, projects, or beliefs. Things they do or deliberately have not done. Some of them can be the result of what in Organization Theory we call “escalation of commitment.” We have committed to something, and determinedly fought for it – and perhaps for all the right reasons – but now that things have changed and it no longer makes sense, we may still be inclined to persist. A good question to ask yourself is “what would other, external people do, if they found themselves in charge of this company?”

Intel’s Andy Grove called it “ the revolving door ” when discussing strategy with then-CEO Gordon Moore; let’s pretend we are outsiders coming new to the job, ask ourselves what they would do, and then do it ourselves. It led Intel to withdraw from the business of memory chips, and focus on microprocessors. This resulted in more than a decade of 30 percent annual growth in revenue and 40 percent increase in net income.

3. Is my organization consistent with my strategy? In 1990, Al West, the founder and CEO of SEI – the wealth management company that, at the time, was worth $195 million – found himself in a hospital bed for three months after a skiing accident. With not much more to do than stare at the ceiling and reflect on his company’s present and future, he realized that although they had declared innovation to be key in their strategy, the underlying organizational architecture was wholly unsuited for the job. When he went back to work , he slashed bureaucracy, implemented a team structure, and abandoned many company rules. The company started growing rapidly and is now worth about $8 billion.

As a consequence of his involuntary thinking time, West did what all business leaders should do: he asked himself whether the way his company was set up was ideal for its strategic aspirations. What would your organization look like if you could design it from scratch?

4. Do I understand why we do it this way? When I am getting to know a new firm, for instance because I am writing a case study on them, I make it a habit to not only find out how they do things but also explicitly ask why. Why do you do it this way? You’d be surprised how often I get the answer “that’s how we have always done it” [while shrugging shoulders] and “everybody in our industry does it this way.”

The problem is that if you can’t even explain why your own company does it this way, I am quite unconvinced that it could not be done better. For example, when more than a decade ago I worked with a large British newspaper company, I asked why their papers were so big. Their answer was “all quality newspapers are big; customers would not want it any other way.” A few years later, a rival company – the Independent – halved the size of its newspaper, and saw a surge in circulation. Subsequently, many competitors followed, to similar effect. Yes, customers did want it. Later, I found out that the practice of large newspapers had begun in London, in 1712, because the English government started taxing newspapers by the number of pages they printed — the publishers responded by printing their stories on so-called broadsheets  to minimize the number of sheets required.  This tax law was abolished in 1855 but newspapers just continued printing on the impractically large sheets of paper.

Many practices and habits are like that; they once started for perfectly good reasons but then companies just continued doing it that way, even when circumstances changed. Take time to think it through, and ask yourself: Do I really understand why we (still) do it this way? If you can’t answer this question, I am pretty sure it can be done better.

5. What might be the long-term consequences? The final question to ask yourself, when carefully reflecting on your company’s strategy and organization, is what could possibly be the long-term consequences of your key strategic actions. Often we judge things by their short-term results, since these are most salient, and if they look good, persist in our course of action. However, for many strategic actions, the long-term effects may be different.

Consider a practice adopted by many of the UK’s IVF clinics – of selecting only relatively easy patients to treat, in order to boost short-term success rates (measured in terms of number of births resulting from the treatment). The practice seems to make commercial sense, because it (initially) makes a clinic look good in the industry’s “League Table.” But, as my research with Mihaela Stan from University College London showed, it backfires in the long run because it deprives an organization of valuable learning opportunities which in the long run leads to a lower relative success rate.

When you start a new strategy or practice it is of course impossible to measure such long-term consequences ex-ante, however, you can think them through. For instance, when we asked various medical professionals in these clinics what might be the benefits of treating difficult patients, they could understand and articulate the learning effects very well. They could not measure them, but with some careful thought they could understand the potential long-term consequences before even engaging in the strategic action. Actions often have different effects in the short and long run. Sit down and think them through.

Strategy, by definition, is about making complex decisions under uncertainty, with substantive, long-term consequences. Therefore, it requires substantial periods of careful, undisturbed reflection and consideration. Don’t just accept the situation and business constellation you have arrived at. Leadership is not just about doing things, it is also about thinking. Make time for it.

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11 common strategic planning questions, answered, we’ve heard these questions asked by many people over the years—and i bet you’ve asked at least one of them..

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Ted Jackson

11 Common Strategic Planning Questions, Answered


After years of helping organizations simplify their strategy and reporting processes, it has become clear that many organizations struggle with similar strategic planning questions. Because all these questions are important—and the answers tend to help organizations get a better grip on their strategy—we decided to share the ones we hear most frequently below.

11 Common Strategic Planning Questions

1. what time frame should our strategic plan cover.

Your strategic plan should look as far into the future as you’re comfortable looking. But keep in mind, you need to be confident that your company’s environment will be stable during the period of time you choose. In the 1980s, Japanese automotive companies were looking out 40 years into the future—but this probably isn’t realistic for your organization. Most companies feel comfortable with a three- to five-year strategic planning horizon so long as they review their plan on a regular basis.

2. Who should be part of the strategic planning process?

The strategic planner is typically the leader of this process. They will also need the help of a cross-functional team that includes members of the board or leadership, along with representatives from finance, human resources, operations, sales, and any other critical functions.

That said, we recommend not limiting the planning process to just senior management. If you want the plan to work, it must engage everyone to some degree. So while the leadership team may be more involved in final decisions, those decisions should be based on input gathered from managers and their teams. What are their thoughts on the future of the business? What do they think your company is doing well, and where does it need improvement? What projects are people working on and how are those contributing to the big picture? Including this type of feedback in your deliberations is the best way to gain buy-in around the strategic plan.

3. How often should we review progress on our strategic plan?

The frequency of plan review varies depending on the goal of the review:

We recommend setting up these meetings at the beginning of the year to ensure you hit these cadences. At the same time, determine the appropriate participants for each and send out invites. Monthly meetings might include a director from each department; quarterly meetings require a smaller set of leaders; and annual strategic retreats are usually reserved for the highest levels of leadership. Getting these meetings on the calendar early not only reserves the times, but also sets an expectation for preparedness.

4. When should we change or update our strategic plan?

As mentioned in #2, an annual review of your strategic plan helps ensure the key elements in your plan are still valid. If there’s been a significant shift in the marketplace, for example, you may need to reevaluate your high-level goals and objectives. Or, you may need to add new projects, change or update how you’re tracking KPIs, or change your KPI targets. Periodic strategy refreshes allow you to keep the elements of your plan that are valid and adjust the parts that are not.

5. Do we need a strategic planning office?

Not necessarily. All organizations—even those with only two employees—need to spend time on strategy. If your company fails to prioritize strategic planning, it could get left behind during times of environmental uncertainty or in a tumultuous business market. So while your organization may not be large enough to have an entire strategic planning office or department, you do need to ensure that at least one person in your company has time on their calendar dedicated to your strategic plan.

6. Do we have to use a Balanced Scorecard?

No. That said, the Balanced Scorecard has proven to be a powerful and time-honored way to plan and execute strategy. Regardless of whether you stick to the Norton-Kaplan methodology or use a variation, understanding the basic principles of a BSC—having clear goals, linking your projects to those goals, and setting up leading and lagging indicators—could help your strategy immensely. And for any strategic planning model to work, you need to have the right goals and the right way to measure and achieve them.

7. Where do we start when it comes to devising a strategy?

Many companies aren’t sure how to begin developing a strategy—how do you see the best way forward? Here are two important questions to ask during strategic planning, both of which will yield important information that can help you chart a path:

Where are we now and where do we want to be?

As you get started with strategic planning, take the time to understand where you are now—your current business. Know the sales trends in every product/service area, the relative profitability of each of your products and services, the amount of money you have and will have/need in the foreseeable future, and your position relative to your competition, among other things. And because strategic planning is essentially a roadmap for the future, you also need to clearly describe the ideal desired outcome for your business.

Project forward five years—what do you want your business to look like? The greater clarity you have about where you want to be at a specific time in the future, the easier it will be for you to create a great business plan, or blueprint, that enables you to get from where you are today to where you want to go.

What obstacles lie in our path, and how do we go about removing them? Every strategic plan will face risks and potential derailments. Some of these risks can be foreseen (for example, the internal weaknesses you discover as part of a SWOT analysis ), while others cannot. This is one of the most difficult steps in developing a strategic plan, but the long-term success of the company is worth the temporary discomfort of having candid conversations. Management teams should outline the known risks along with financial impacts, and articulate the mitigation plans to prevent or curtail them. Sometimes, just identifying and removing one critical obstacle can turn your company into a more profitable enterprise.

8. What is the difference between a strategic plan and an operational work plan?

Linking your operational work plan to your strategic plan is the ideal scenario. That way, the issues your department or division is focused on for the year are in line with your strategic plan.

This approach also allows for each department to see how their efforts directly impact your strategic goals, which adds an invaluable motivational element.

9. How many measures should our strategic plan include?

At each level in your organization—the enterprise level, division level, and department level—we recommend having 20-30 measures. We’ve found that a number in this range helps each level stay focused on what’s important, and review key data in meetings without distraction or fatigue.

Of course, 20-30 measures in every division described above could leave your company with hundreds of measures, but don’t worry—the goal is never to review every single measure in the organization at the same time. You should plan on reviewing only the information critical to your strategy in your department or division every quarter. That said, use common sense. If one of the measures at the division level above you or the team level below you is red, you might want to look at it before your review to make sure that it doesn’t impact your team.

10. How do we make our strategic plan flexible to allow for changes?

The best way to make your strategic plan flexible is to have a clear distinction between your goals, measures, and projects, as this enables you to make changes, additions, or deletions more easily. Goals should be updated every one to five years, and measures should be updated every six to 24 months. Projects can be adjusted on a quarterly basis, with completed projects being rolled off and new ones added. At this time, you may also need to make changes to some aspect of a project, for example changing the end date or adjusting the budget.

11. How can we organize and track strategic planning information and data?

Your strategic plan should touch a variety of departments and divisions. Even if you’re extremely well-organized, keeping track of all the data coming from different individuals and in different formats is very difficult. Some organizations attempt to use Excel or PowerPoint, but both of these tools fall short when it comes to strategy management. Excel was designed to track data, make tables, and run calculations, but it wasn’t designed to track progress over time, show qualitative analysis (comments), or link strategy elements together. PowerPoint is great for creating presentations, but you have to build a new deck for every monthly meeting. If you plan to use either of these tools, you can count on putting in hundreds of hours per meeting doing manual calculations, formatting graphs, updating versions, etc.

Automating the process with software like ClearPoint helps tremendously and will, in the long run, save your company a great deal of time and energy. Tracking and reporting tasks that would otherwise take days, takes only minutes with ClearPoint. Many of our clients have also found that managers are more inclined to stay on top of their metrics simply because the software is so easy to use. When you can produce more informative strategy reports in less time— and get people excited about metrics to boot—it’s a win all around.

What other key questions do you have about strategic planning? Shoot us a quick email or tweet us @clearpointstrat —we’d love to add your question to our FAQ list!

11 Common Strategic Planning Questions, Answered

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Key Questions for Strategic Planning

Contact us to help you address these and other important questions that may arise as you develop or revise your strategic plan.


10 Questions for your strategic planning session

1. What is the one thing your company did best this year? How can we leverage this more?

2. What is the one thing your company should improve upon?

3. Which employee(s) prevented you from doing your best this past year?  What should you do about it?

4. Which department, team or function(s) prevented you from doing your best? What should you do about it?

5. Which team member was most responsible for your company’s success this year?  How can we maximize this member’s impact on others?

6. Which department, team or function(s) was most responsible for your company’s success this year? What best practices can we pass on to others?

7. What is the single Key Performance Indicator you least liked hearing about this year? What strategies and action plans can we implement to improve?

8. What is the single metric you will measure your company’s success by? What can you do to make sure the goal is achieved?

9. If you had a clean sheet, what changes would you make to your company?

10. If a perfect competitor opened up across the street, what would they look like?

Performance Culture provides Strategic Planning and Performance Review Templates that can help you facilitate your next planning session.

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More From Forbes

Four questions to ask yourself as you develop a strategic plan.

Forbes Coaches Council

Strategic planning is a commonly misunderstood concept in the business world. Entrepreneurs and business owners may think they have a strategic plan in place simply because they have goals and a general idea of how to attain them, but it’s so much more than that, and it is a crucial discipline for leadership teams to adopt if they haven’t already. Strategic planning is a way for leaders to step out of the day-to-day activities of running the business in order to focus on long-term strategy and ask themselves, "Are the day-to-day activities aligned with long-term objectives? Why or why not? What adjustments need to be made?" It’s a way to step back and honestly assess performance, priorities and problems so you can be deliberate about course-correcting.

Without strategic planning, decisions can lack direction, and daily tasks often lack purpose. Time and energy are wasted on endeavors that do not align with your company’s mission and vision. Investing the necessary resources in strategic planning upfront can bring peace of mind by providing strategies and skills to help your company reap dividends for years to come.

Most businesses practice strategic planning annually, but the best ones do it more frequently, such as twice a year or even quarterly. When addressed infrequently, strategic discussions can become overwhelming to the business owner. On the other hand, when companies believe they can strategically plan as they go through the year — rather than setting aside specific times to really focus on it — it often ends up being dropped for the sake of seemingly more pressing tasks. That’s why for me, Q4 is always strategic planning season. Making sure it is a seasonal rhythm and knowing when it is coming allows me to dedicate the necessary time, attention and reflection.

As the saying goes, “He who facilitates, doesn’t participate,” so for leadership teams that do this strategic planning internally, at least one member may be at a detriment. In my experience, it can be worth hiring an outside facilitator to lead the sessions so that all leaders have the chance to fully participate. The external facilitator can also bring value as an outsider, asking questions from a different perspective, or playing the part of the voice of the customer or competitor.

I offer two types of strategic planning sessions, one that's focused entirely on the business and another that focuses on professional development and team building. One of the first things I do at the start of each session is ask the attendees a series of questions to help them evaluate their long-term objectives and current trajectory. Here are four questions every leader and team should ask when setting out to build a strategic plan:

1. Where do we want to be in 3-5 years?  

To answer, conduct a SWOT analysis to clearly identify the company’s internal strengths and weaknesses, as well as external opportunities and threats. To develop a long-term strategy, you must know your strengths so you can build a strategy that accentuates them. Don’t know your strengths? Conduct a marketing competitive analysis or customer survey prior to planning sessions to get a clear picture. Companies that guess at their strengths and competitive advantages very often get it wrong because they are too biased. An outsider’s perspective is imperative.

2. Where are we today in relation to these goals? 

An honest assessment of your company’s current trajectory toward your objectives is the only way to form an effective strategy to achieve them. Pretending you are further along than you really are will only set the company back in the long run. However, don’t let your team get discouraged if you are nowhere close to reaching your goals. That’s where strategic planning comes in, and the next two questions will guide you as you move forward.

3. What obstacles lie in our path, and how do we go about removing those obstacles?

Often, this means addressing and tackling those internal weaknesses discovered in the SWOT. While this may be the most difficult step in developing a strategic plan, the long-term success of the company is worth the temporary discomfort of candid conversations.

4. How are we going to measure our progress and know when we’ve reached our goal?  

This final question is of utmost importance, and something many companies forget to consider. Be very precise and specific with this, not at all general or generic. If you cannot measure progress, you cannot rally people toward the goal.

For example, I once helped develop a strategic plan for a country club in one of Houston’s wealthiest neighborhoods. When the general manager started there, he was determined to change the second-tier perception of the club and create a unique and wonderful family club experience. We set out to define the long-term strategy of how to do that, identifying multiple objectives and initiatives, owners for each initiative, and the steps and phases involved with each. When it came time to decide how we would measure success, the GM said it was simple: “When we have a waiting list.” At the time, anyone could walk in, take a tour and immediately write a check and become a member. When they reached capacity and finally had a waiting list, they knew they had succeeded in improving the member experience. The day that waiting list was created, two years later, was a day that was celebrated by everyone on the team!

For many executives, the idea of formulating and implementing a strategic plan is intimidating, but if you carve out the time to ask these tough questions and answer them truthfully, I think you will find that strategic planning is well worth it. It can inspire and empower your employees with a clear vision and direction, and it can ensure everyone is rowing the boat in the same direction toward meeting and surpassing your growth goals.

Sheryl Lyons

strategic planning discussion questions

  40 Strategic Questions to Ask

Asking intelligent questions of employees or customers and analyzing their responses is critical for executives who are responsible for making decisions and setting corporate strategy. Ask the wrong questions of the wrong people, and you will not receive the necessary organizational intelligence needed to drive optimal outcomes. Worse yet, you might waste valuable time and resources in the process. Instead, find the right strategic questions to ask.

At 9Lenses, we are experts at helping leaders ask the right strategic questions and analyze the feedback to: determine the success of existing strategies, identify gaps in the strategy, and establish optimal strategic actions going forward. Consultants, Fortune 500 companies and SMBs alike have used our digital client engagement platform to automate this questioning process, asking thousands of questions to tens of thousands of stakeholders.

Below are 40 strategic questions to ask your employees or yourself from   our platform  that you can use that evaluate strategy comprehensively. These questions cover such areas as: General Strategy, Competition, Product, Pricing, Customers, Sales, etc. – just a small sample of the areas that our platform is capable of pulsing.

Strategic Questions to Ask

Assessing your current strategy.

1. Does your organization’s corporate responsibility strategy match the availability of your current resources?

This question addresses your strategy in terms of the funding, time, people, and information necessary to make the strategy work, determining its feasibility.

2. How often does your organization assess its strengths, weaknesses, opportunities, and threats in order to understand the current business climate?

Measuring these aspects of the strategy will help to analyze the company’s current approach to strategic evaluation and reveal if it is necessary to analyze it more often.

3. How effectively does your organization form and make profitable use of partnerships?

Partnerships can be helpful assets to your company, but they must actively be sought out and well-utilized.

4. If you were in charge of strategic planning for your organization, what changes would you make?

Asking your employees for their own ideas can not only provide interesting suggestions for future initiatives, but also can reveal any discontent with current strategy. With the high importance of strategic planning, it is crucial to ensure your company is creating analytical, actionable plans.

5. How efficient is your organization from an operational standpoint?

Determining operational efficiency can assist in revealing the reasons behind the success (or lack thereof) of your current strategy. By discovering the operational inefficiencies inhibiting success, your company can identify key process improvements.

6. How well does your organization utilize its people as an asset to help it improve, stay competitive, and strategically meet goals? Are people used efficiently or is talent wasted due to lack of effective strategy?

A major problem in many companies is a lack of utilization of existing resources, including the use of people and their particular strengths. Employing an effective strategy can better reveal the particular assets of your employees that can then be engaged to better the company overall.

Assessing your Competition

7. How often does your organization analyze the competition in order to understand competitive advantages and disadvantages as well as identify areas for investment or needs for improvement?

Regular assessment of the competitive landscape is a crucial determinant of corporate strategy, and fine-tuning the frequency of this evaluation will help to reveal how your company’s doing in terms of competitor analysis.

8. How well does your organization strategically differentiate from the competition in terms of the capabilities of its product? How clear is your organization’s strategy for this?

This question helps to analyze and assess competition in a clear, specific way that will yield insight into the differentiation strategy.

Assessing the Future

9. How clear is your vision for what corporate responsibility should be like in your organization in the future? Is the direction that the organization wants to go in clear and understandable?

Clarity is an important part of strategic success, and this question can help determine the intelligibility of your strategy from the perspective of your employees.

10. Is our long-term view reflected in our short-term priorities? Are we pouring effort into initiatives today that have connections with where we expect ourselves and the market to be in the future?

Strategy without long-term perspective is useless, and clear, direct thinking about the future can help ensure the durability of your strategy.

11. Is your organization pursuing growth and new business/market development with as much passion as it does operational efficiency?

This question still addresses the importance of planning for the future, but also focuses on the sense of urgency for growth. Finding the balance between day-to-day operations and new developments is critical for your company’s future success.

12. How effective is your organization’s strategic vision?

A strategic vision involves a clear view of the desired future position of an organization within a market, giving your company a goal to plan around that, when implemented correctly, will produce results.

13. When developing and implementing strategy, does your organization effectively balance short and long-term priorities?

This question further addresses the balance between concentrating on daily operations and on future growth that must exist in your company.

14. How efficient and organized is your organization’s plan for how to improve and evolve the strategic objectives over time?

Just having a set plan for the future is not enough; it must be structured, logical, and well-communicated in order to help direct your company.

15. How do the potential negative consequences that could occur with the implementation of a new strategy compare to the potential positive outcomes?

If the results of these questions suggest that a new strategy is necessary, your company must ensure that this new plan will not cost your company more than it will benefit it. This return analysis helps to evaluate if the pros of new strategic implementations can outweigh the cons.


Assessing your connections.

16. How many established outlets does your organization have through the Internet (social media, websites, etc.)?

By assessing the Internet outlets of your company, you can discover insight into how well your business is utilizing available online resources.

17. How many established connections to other businesses does your organization have?

Connections with other businesses can be used to create new partnerships and go-to-market opportunities, and therefore determining how many connections already exist for your company can help assess current strategy.

18. How many established connections does your organization have with consistent and dependable customers?

Customer advocates can be a lucrative avenue for your company to sell products and thus generate revenue, so determining the extent to which your company capitalizes on these relationships can help assess the effectiveness of your distribution strategy as a whole.

Assessing your Outlets Overall

19. How effective is your organization’s delivery model?

Your company’s delivery model is the method for getting your offering to your customer, and a successful model is a key aspect of your go-to-market strategy.

20. How much potential benefit for the organization does the distribution strategy have?

It is crucial to determine the positive outcomes that the current distribution strategy permits in order to analyze if your company is effectively utilizing its delivery outlets.

21. Considering all possible outcomes, how much risk does the distribution strategy have?

On the other hand, it is important to determine the risk in this strategy. Answering these questions separately then comparing the results can help to fully analyze both sides of the issue.

Product Offering

Assessing your market.

22. To what degree are your offerings clearly differentiated in their market?

This question is important to ask in order to analyze how your company is distinguishing its products from that of competitors and thus working to permeate the market as much as possible. This type of question is important to ask when assessing your competition (see also #8), as well as when analyzing your product itself.

23. How much ease and expense is required for your customer to switch to a competitor’s offering?

It is important to understand product stickiness and customer switching costs to determine how your customer values your product.

24. How often does your organization analyze the competition in order to understand competitive advantages and disadvantages as well as identify areas for investment or needs for improvement?

This question can reveal whether or not your company is evaluating your competition often and in a thorough manner.

25. Based on your knowledge of current efforts to promote your services, what are the major internal barriers to selling your services to clients?

By determining impediments to selling services, your company can find ways to avoid these hindrances and strategise better as a whole.

26. How well does your organization maximize existing resources in order to deliver the product offering?

This question evaluates the method for getting your offering to your customer in order to reveal certain resources that your company could be better utilizing.

27. How aligned are your organization’s offerings to meet market demand?

Not only do you want to be producing the offerings that leverage your organization’s resources, but you also want to be delivering the right products for your target market.

Assessing the Value to your Customers

28. Does your product offering encourage innovation for the customer through versatility, usability, and efficiency?

The more innovative your company’s offerings are, the more valuable they can be to your customers, for innovation is key in any product.

29. How well do the organization’s products solve the customers’ problems and meet their expectations?

Evaluate how your product meets the expectations of your customers in order to ensure the value in your offerings.

30. How frequently does your organization deliver new value-adding ideas to your customers to keep them engaged?

This question addresses how fresh your company is staying with your product and your customers, which is crucial in terms of retaining them as clients.

31. What is the direction and state of our innovations? Is the direction right for now, 5 years from now, and 10 years in the future?

A great tactic to use when analyzing the strategy of your company is to envision your product years from now and determine if your product roadmap is truly innovative.

32. Does your organization have several strategies for differentiation, innovation, customer alignment, and a detailed plan of forecasted strategies?

This multifaceted question assesses how well your company is planning for the future in terms of your offerings.

Pricing & Promotion

Assessing your pricing.

33. Considering factors such as competition and timing of discounts, does your organization provide the right amount of discounts and at the right price?

Discounting, when executed correctly, can be a great tactic to utilize, and this question addresses how well your company is using this strategy.

34. Does your organization’s pricing strategy match with the availability of your current resources?

This question addresses prime optimization, which is how well your organization prices its work in comparison to other organizations without forfeiting profit.

Assessing your Promotions

35. Does your organization promote itself through its people? Do the people actively promote your organization?

One of the greatest resources that many companies fail to use is their own people. Employees of an organization can be a company’s best proponents if they are actively and enthusiastically promoting the organization.

36. How effective is your organization at using product placement to subtly appeal to the customer?

Product placement deals with strategically implementing your offerings in context without advertisements, and can be a useful promotion strategy when employed correctly.

37. How often are your organization’s web strategies updated in order align with current organization news and capabilities?

Web strategy must be updated frequently in order to be useful to your company, and this question addresses the regularity of these revisions.

38. Is your organization’s website professional, visually pleasing, and effective at generating customer revisits?

Analyze your website design in order to determine if your company is fully optimizing its web presence.

Assessing your Sales

39. How effective is your organization at ensuring loyalty of current customers by extending various incentives for loyalty to your offerings?

Loyalty marketing is a promotional tool that can help your strategic advancements, as long as the incentives are right for your market, customers, and product.

40. How often does your organization convert leads for potential sales into actual sales in the long run?

This question, though basic, must be asked in order to reveal any problems in your current sales strategy that could be modified in order to better your company’s sales overall.

We hope you find our list of strategic questions to ask your employees or yourself valuable and beneficial to your company. These questions represent a small sample of our diagnostic library that we draw upon when running 9Lenses diagnostics for our clients. Because each question tends to elicit an in-depth response, we tend to ask fewer questions per assessment so as not to overwhelm participants. Beyond asking the right questions, it’s important to involve the right set of stakeholders, to analyze the responses for new insights, and measure any changes in performance over time – all of which is possible with our platform.

strategic planning discussion questions

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20 questions to ask during strategic planning for a nonprofit

strategic planning discussion questions


This easy-to-follow guide to strategic planning for nonprofits will help you ask thoughtful questions with your team to make a smart plan for the year.

strategic planning discussion questions

Rachel Mills

Where do you see your nonprofit in the next year? Developing a strategic plan determines which direction you want your organization to take, then maps a route to get there.

A strategic plan doesn't just set your fundraising goals for the year. It articulates your mission and values, then puts a plan in place to hit your targets across fundraising, advocacy, and education. Unfortunately, roughly one-third of nonprofits report not having a strategic plan in place (or even knowing if one exists).

Below, we offer a step-by-step tutorial on how to write a strategic plan for a nonprofit. We explain which areas your plan should cover, which of your people to include, and how to put the plan in place.

What is strategic planning for a nonprofit?

A strategic plan is a living document that outlines your goals for the year. The document is divided into different sections, including the research, people, marketing, and technology required to hit your objectives.

The strategic planning process always begins with a revisit to your organization's mission statement and values.

By returning to your core cause, you prevent "mission creep" from year over year. In other words, it realigns your priorities with the reason your organization exists.

Similar to a business plan, a strategic plan is meant to be a living, flexible document. As every nonprofit knows, there are countless disruptions throughout the year — not limited to budget restraints, natural disasters, and global pandemics . You know changes happen. Your strategic plan ensures you set your sights on your most important initiatives, even within a changing environment.

7 steps for strategic planning for nonprofits

A good strategic plan is an all-encompassing document. It addresses every department, resource, and individual within the nonprofit organization, and how they'll contribute to your year-end goals.

1. Gather all stakeholders together 👯

Many organizations make the mistake of only involving board members and chief executives in the strategic planning process. by expanding initial discussions across all staff and volunteers, you gain fresh (and often, more accurate) perspectives on what you can accomplish in one year..

Gather your team and consider the following questions:

2. Conduct original research 📊

Nonprofit strategic planning involves taking a hard look at what works — and what doesn't — within your organization.

For a fair assessment, always back up your claims with facts and metrics.

Interviews, surveys, and past year results offer insights into gaps and opportunities for the upcoming year. Try the following exercises:

3. Revisit your vision, mission, and values 💯

Nonprofit leaders should revisit their vision statement, mission, and values at least once a year (if not once a quarter). This ensures every goal you set and project you take on aligns with your cause.

Sometimes, your mission, vision, and values need to change. If research (in step two) shows your mission isn't clearly defined, your vision isn't realistic, or your values aren't clear, it's time for an edit. Within your nonprofit strategic plan, consider the following:

4. Set your objectives 📌

Your strategic goals should encompass programming, advocacy, and fundraising.

As an exercise, list these three buckets on a whiteboard. Have your team list everything they wish to accomplish within each category (there are no bad ideas!). After 30 minutes to an hour of brainstorming, have everyone vote on their top two priorities within each category.

Having trouble getting the ball rolling? Try these questions to start your brainstorming session:

5. Create a roadmap toward your objectives 🗺

You have 12 months to accomplish the goals set in step four. Work backwards from each goal, setting deadlines, delegating tasks, and assigning milestones.

Hopefully, your human resources department or manager can assign a project manager for this step in the process. A project timeline should accompany each goal, breaking down the following:

6. Pick tools to accomplish all of the above 🛠

You have your purpose, goals, and people in place. Now, determine what else you need to hit your targets.

In the short-term, your team may need a project management system to delegate tasks, a CRM system to keep track of donors , and a giving platform to raise funds and increase donor retention.

Your nonprofit strategic plan should include a budget for all tools and technology needed.

When considering which resources you need, consider the following:

7. Get buy-in from your team 💪

Lastly, present your strategic plan to your executive director, board of directors, and funders. Ensure each person is aligned with your mission, objectives, and budget.

As you present your strategic plan in an executive or board meeting, remember to return to the following points:

Givebutter can help you accomplish your strategic priorities

A strategic plan is an essential document within the nonprofit sector. A strategic plan is the roadmap for the upcoming year, aligning all stakeholders on your priorities, mission, and objectives.

Givebutter can help you raise funds to accomplish your year-end goals. With 70+ features at your fingertips, it offers the tools your team needs to hit your fundraising targets and amplify your message. Plus, with the lowest platform fees in the industry, Givebutter helps you keep more of the money you raise.

Ready to launch your next campaign? Sign up for your free account to start fundraising today.

Rachel Mills

Rachel is a fundraising and marketing consultant for nonprofits whose aspiration since she was 16-years-old is simply this: help others, help others.


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BUS303: Strategic Information Technology

strategic planning discussion questions

Strategic Planning

Read this chapter, which serves as a guide on writing a strategic plan by guiding you through the situation analysis and developing an organizational strategy formulation. The authors note that  "the strategies and actions implemented at the functional (department) level must be consistent with and help an organization achieve its objectives at both the business and corporate levels and vice versa".  In practical terms, think about implementing a new IT strategy at a medium-sized firm of 20–199 employees. Who would need to be involved in the planning and implementing the strategy?


Have you ever wondered how an organization decides which products and services to develop, price, promote, and sell? Organizations typically develop plans and strategies that outline how they want to go about this process. Such a plan must take into account a company's current internal conditions, such as its resources, capabilities, technology, and so forth. The plan must also take into account conditions in the external environment, such as the economy, competitors, and government regulations that could affect what the firm wants to do. Organizations must also offer value to customers and graduates must provide value to their employers. As such, the value proposition becomes the basis for developing strategies. Given its importance for both organizations and students, we begin with the value proposition and then discuss the strategic planning process. Just as your personal plans - such as what you plan to major in or where you want to find a job - are likely to change, organizations also have contingency plans. Individuals and organizations both must develop long-term (longer than a year) strategic plans, match their strengths and resources to available opportunities, and adjust their plans to changing circumstances as necessary.

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