Here are 50 tough questions that will help you have an honest, strategy-building conversation with your key people about your organization, leadership, products, customers, people, revenue and competition.

This article was first published as a LinkedIn article in November 2017. It was reposted in the following Groups: Postal Innovation, The Harvard Business Review and The Economist Newspaper readers.

Having this conversation can save your business

Henry Mintzberg, Canadian academic and author on business and management, said that strategy is often emergent, where a company serendipitously reacts to events as opposed to doing research, analysis (Trend, Situation, SWOT, GAP and more) and strategy building.

If so, these companies can, by reading their trail of breadcrumbs, easily describe what their strategy was after the fact but they can’t tell you what their go-forward strategy really is. Clearly, this is not really a strategy at all.

Yet, establishing a business strategy does not have to be a formal nor onerous exercise.

Have the conversation

Strategy formulation can be as easy as having a conversation among key people within your organization. Not being afraid to ask and explore the tough questions is a powerful thing. When having a conversation, people can look at statistics together, discuss, examine divergent views, hear new ideas, look at unusual possibilities, learn new things, engage with each other, build bonds and reach conclusions together – leading to common understandings.

In today’s fast-changing world, there is already an innate Urgency to stay proactively ahead of events instead of reacting to them. Senior management, as the organization’s leadership, is already the basis of a Coalition required to lead any change initiative. Engaging with other people, from different functional parts of the organization, in a conversation will help to bring in divergent views.

By having that honest conversation, your group will be able to Articulate a Clear Sense of Purpose (Mission) and Vision that can then be communicated to everyone in the organization.  A mission is an organization’s big-picture-thinking, grand purpose or why it exists. A vision is what a company aspires to be in the future.

Everyone wants to understand the organization’s larger social role. Employees want to believe that they are contributing to something that is transcending or lasting.

In 1961, President John F. Kennedy articulated for the world, NASA’s “mission”: “Achieving the goal, before this decade is out, of landing a man on the moon and returning him safely to earth.” The following year, while touring the NASA facility, the President noticed a janitor with a broom. He walked to the man and said, “What are you doing?”

“Well, Mr. President,” the janitor responded, “I’m helping to put a man on the moon.” That’s the kind of understanding, focus, pride, enthusiasm and engagement that we all want our employees to have.

Some inspirational missions

  • IKEA creates a better everyday life for the people that they aim to serve.
  • Facebook gives people the power to share and make the world more open and connected.
  • Starbucks inspires and nurtures the human spirit – one person, one cup and one neighbourhood at a time.
  • Twitter gives everyone the power to create and share ideas and information instantly, without barriers.
  • Microsoft empowers every person and every organization on the planet to achieve more.
  • Patagonia builds the best product, causes no unnecessary harm and uses business to inspire and implement solutions to the environmental crisis.

Sadly, Apple’s current mission statement (2017) reads more like a marketing summary – “Apple designs Macs, the best personal computers in the world, along with OS X, iLife, iWork and professional software. Apple leads the digital music revolution with its iPods and iTunes online store. Apple has reinvented the mobile phone with its revolutionary iPhone and App store, and is defining the future of mobile media and computing devices with iPad.”

We prefer the Steve Jobs original – “To make a contribution to the world by making tools for the mind that advances humankind.” It’s a statement that warms the heart.

So, are you ready to lead your organization and outline how your organization will change the world?

50 Tough questions

Here are 50 tough questions that will help you have an honest, strategy-building conversation with your key people about your organization, leadership, products, customers, people, revenue and competition.


  1. How is business and why? (The Brutal Facts)
  2. Are we technologically behind or are we still relevant to our customers?
  3. Will we be still be relevant 5 years from now?
  4. Are we changing as fast as the world around us?
  5. What are the things that are wrong with our organization?
  6. What one word do we want associated with our brand in the minds of our employees, customers and partners?
  7. How does what we do improve people’s lives and the world we live in?
  8. Who have we, as an organization, historically been when we’ve been at our very best?
  9. What are our organization’s core values and do those values prioritize our employees, our customers and then our shareholder?
  10. What are the strategic uncertainties that keep us awake at night?


  1. What is our Big Audacious Goal that everyone can work toward?
  2. If this was the family business, what actions would we really take?
  3. What should we stop doing?
  4. How would we create in our organization a culture that fosters innovation?
  5. What critical performance variables to we track, measure and publish to the public?
  6. How would we improve security oversight over the reporting on funds right down to the branch office level?
  7. How would we ensure that we have trained, territory managers and a written process of periodic financial reviews at each branch office?
  8. How would we ensure that when we build or repair branch offices we are getting the best possible rates?
  9. How would we improve the continued reliability of our incoming raw-material supply (i.e. parcel shippers, parts, etc.) process?


  1. What is wrong with our products?
  2. What features of our products do people like?
  3. How can we improve people’s perception of our products and services?
  4. What is stopping us from introducing many more innovative products or services to our customers?
  5. What diversified products or services do our customers need, want and are willing to pay for?
  6. What are the gaps in what consumers want versus what is available in the market?
  7. What is stopping us from offering customers what they want?


  1. Do we know the profile of our typical or average customer?
  2. What would we change in order to give people more access to our services?
  3. Who are we not selling to because we think they can’t or won’t pay?
  4. How can we inject a positive emotional, customer experience in our product or service?
  5. How can we partner with our customers or provide added services to them to make them successful?


  1. Do our people look forward to coming to work?
  2. Does our HR process of quarterly goals and annual performance assessments encourage achievement of short-term successes and discourage disruptive innovation for growth that takes more time to prove successful?
  3. Do we have the right people with the right skills?
  4. How loyal, committed or engaged are our employees in helping each other and helping the organization succeed?
  5. Do we aggressively celebrate every employee achievement?
  6. How would we ensure that our people improve customer service or the customer experience in order to improve our overall sales?


  1. What do we need to change in order to increase our revenue?
  2. What are we doing to make every branch office break-even (revenues covering costs)?
  3. What would we have to do to make the organization self-sufficient and operate without a loss or a subsidy?
  4. What would we change in order to lower our operating costs?
  5. What would we have to do to generate and sustain an annual profit?
  6. How effective are our campaigns to increase our sales and do we track the effectiveness of those merchandising and marketing campaigns?
  7. What things would we have to change to increase the volume of business activity?
  8. Do we set appropriate annual and quarterly sales growth targets for our territory managers?
  9. What can we do to encourage and support domestic commerce and exports?
  10. How will it be rewarded?


  1. Who are all of our competitors?
  2. Why are our competitors successful?
  3. How can we do what they do?

Good conversation and good strategy building!

Remember the words of Rob Siltanen, creator of Apple’s 1997 “Think Different” ad campaign, “The people who are crazy enough to think they can change the world are the ones who do.”

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