20 Questions To Get You ‘Thinking Strategically’ As A Leader!


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Do you find yourself getting caught up in the ‘day to day’? Do you get dragged down too much into the detail? Do you sometimes struggle to ‘see the wood for the trees’? It’s a constant challenge for leaders at all levels of businesses, but those that overcome these challenges are often the most effective when it comes to leading and managing others.

We all know that we should take some time out to ‘think strategically’ and there’s lots of evidence that suggests it’s an important thing to do as a leader, but it’s not that easy.

What exactly should we ‘strategically think’ about? How do we identify the ‘key issues’? What should we focus on? Well, there are no ‘magical answers’, but the winning leaders we see take time to ….

  • Look at the bigger picture
  • Focus on all aspects of the business – not just the ‘numbers’!
  • Concentrate initially on the ‘what will be in place’ rather than the ‘how will we get there – that comes later!

So, to get you (re) started, I’ve put together 20 questions to ‘get you thinking strategically’ – obviously they are not set in stone, and you don’t have to answer them all! In fact, you don’t have to answer any – you choose what’s best for you and your business!

How you do it, when you do it, and who you do it with is completely up to you, but I would encourage you to do something!

Imagine, it’s 3 years from now…

1. Where will we actually be as a business?
2. What will we be doing differently?
3. What will actually be in place?
4. What will we have achieved when it comes to our customers?
5. What will we have achieved when it comes to our people?
6. What will we have achieved when it comes to our finances?
7. What will be happening then that isn’t happening now?
8. What won’t be happening then that is happening now?
9. How will we be feeling?
10. What will we be most proud of?
11. What will people be saying about us?
12. What will competitors be ‘envying’ about us?
13. Who will our customers be?
14. What will they be getting from us?
15. How will we be providing it (dramatically and demonstrably differently)?
16. What will have changed Politically, Economically, Socially and Technologically that impacts on our business?
17. What will we have STOPPED, STARTED, CONTINUED doing in our business?
18. What will our people be doing, thinking and feeling differently?
19. What will I be doing differently?

And an odd one to get you ‘thinking a bit differently’!

20. Carlsberg don’t run our business, but if they did, what would it look like?

For each of these questions, here are some ‘follow up’ questions….


What if we don’t do anything?

What do others think?

What are the key milestones that will tell us we’re ‘on track’?

Who needs to do what… by when?

So, go on, get your diary out, block a bit of time out, invite and involve others where necessary and get ;’thinking strategically’ – you know it makes sense!

Republished with author's permission from original post.

Andy Hanselman
Hi there! I help businesses and their people create competitive advantage by 'Thinking in 3D'! That means being 'Dramatically and Demonstrably Different'! I research, speak about, write about and work with businesses to help them maximise their sales and marketing, their customer service and their customer relationships.


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