Are You Asking the Right Questions?

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As a leader, typically people come to you looking for answers. Many of us as leaders bite the bait and quickly offer answers. But what if offering answers isn’t the best way to lead? What if a better way to lead is to ask questions rather than offer answers? Jim Collins suggests that strategic planning is more about a search for the right questions than a search for the right answers. So if a key leadership role is to frame questions for the organization, what are the right questions that need to be front and centre if your organization is going to thrive and grow?

People Questions

The first question you need to ask is, “Would I enthusiastically rehire everyone on my team?” It doesn’t matter how good of a strategic plan you have, or how well things are going, if you can’t answer the people question with a resounding and emphatic “YES!!!” you have a people problem. Without the right people on your team, the execution of your strategic plan runs the risk of being derailed, hampered or poorly executed.

Strategic Thinking Questions

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If you were to bring your executive management team together and ask them (without collaboration or consultation) to write out your organization’s one sentence strategy, how many variations of that strategy statement would you end up with? Based on my experience working with nonprofit organizations and mid-growth companies I’d be on fairly good grounds to suggest you’d have as many variations as you have people in the room.

So here’s a few strategy questions that would be good to think through as a management team:

  • What is our one sentence strategy?

  • What is our 10-15 year dream for our organization?

  • What are the non-negotiable core values that dictate how we behave?

  • Why do we do what we do? In other words, what is our core purpose?

  • Who is our core beneficiary or core customer?

  • What are the 3-5 key priorities we need to focus on in the next 3-5 years years?

Focusing on these questions as an executive management team will begin to bring a sense of alignment and focus that wasn’t there before.

Execution Planning Questions

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A good strategic thinking process is only as good as the execution planning process. Here are some execution questions that will help you translate your strategy into measurable outcomes.

  • For how many consecutive months have we met or exceeded our goals?

  • What are the 3-5 priorities we need to make significant progress on in the next 12 months?

  • Of those 3-5 annual priorities, what do we need to do in the next 90 days?

  • What are the metrics or key performance indicators that we will use to help us measure our progress?

  • Who will do what, and by when? Be specific!

Cash/Funding Questions

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Cash is key to any nonprofit organization or business. Without it you’re dead! So here’s some critical cash/funding questions that you need to continue to wrestle with.

  • What kind of cash flow do we need to sustain and grow our organization/business?

  • Of all the things we do what’s the correlation between our expenditures and what we’re identified as our highest priorities? Are we spending a corresponding amount of money on our highest priority activities, products or services

  • What if we were to realize a 1% adjustment in our expenses, income, productivity, client base, donor base? What difference would it make? Obviously if you can reduce expenses and increase income, productivity, client and donor base, the net impact will be a stronger bottom line which will improve cash flow and sustainability.