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30 smart questions every leader needs to ask

These are the questions you should be asking if you want to improve your company.

Whether you’re a CEO, part of the senior management team or an entrepreneur, ask yourself these questions to ensure you know not only how to get the best of out yourself and your employees, but your business, too.

  1. Why does this business exist? 
  2. The logical purpose is to deliver a satisfactory ROI, but it’s up to you to understand and articulate the emotional motivation that will also excite and inspire employees and customers. 

  3. Do we have the right people? 
  4. Consider the team around you – the roles they are in; the experience they have. Are there any holes in the team’s skill set, and if so, can these be filled through training or do you need alternative, or more, staff?

  5. Are we relevant?
  6. You have a target audience that you need to deliver to, but are you definitely giving them what they want? Check out your competition to see if you’re faring better or worse than them. Customer surveys and market research can help identify gaps and also customer loyalty.  

  7. What is it like to work for me?
  8. Being self-aware helps you work out your strengths and weaknesses, which enables you to ensure your senior staff fill any gaps. A 360-degree survey is an ideal way to better understand your leadership style and to find out more about what your team needs from you – as well as what they don’t.

  9. Why should people listen to me?
  10. Your experience is paramount to the success of your business, but how you communicate with your employees is crucial for supporting and inspiring them. Sharing a résumé/back story with onboarders is a good way to let people understand why they should listen to you. How you relate to your teams as a whole as well as to each individual also needs consideration.  

  11. What are our top-line results?
  12. You need to have a daily view of the cash position, tracking the margin of revenue in relation to budget, as well as weekly views of your 2 year rolling forecast. A measure of how you’re developing your people – including their satisfaction at work – is also paramount, as are measures that indicate your level of CSR. 

  13. What are my messages for our customers? 
  14. You want to deliver the best quality for what they want to pay. Ask: ‘Please tell us how we are performing and suggest how we can improve our service offering.’

  15. Where can we break convention?
  16. With so much of business today being about disruption, predicting trends and staying ahead of the curve can dictate success and indeed survival. Look at industries similar to your own to identify what they are doing differently and how you can use technology to better service your customers and leave your competitors in awe.

  17. What prevents me from making the changes I know will make me a more effective leader?
  18. Is it money? Time? Fear? Excellent leadership involves an often-fearless CEO who isn’t scared of making the tough decisions, even at the risk of making themselves unpopular. Research, planning and commitment are at the core. 

  19. Do I do enough to drive innovation and change-initiatives? 
  20. During periods of change, practise what you preach; show everyone a calm, considered approach to business improvement and re-engineering. Explain to all stakeholders what each specific initiative means for them; gather intelligence from customers and staff, and enlist their involvement.

  21. Is my leadership team capable of delivering on my expectations?
  22. Whether you have inherited a team or built it, you need the best available technical acumen and leadership behaviours – your team needs appropriate development and conversations with you, as well as their own regular 360-degree surveys.

  23. What is the plan for developing leadership capacity and succession? 
  24. Each member of the leadership team should be challenged in their everyday role and receive tailored development and support; each should be capable of leading this or another business within the next 3 years.

  25. Who are the 20% of customers that deliver 80% of our margin? 
  26. You need to collect and interpret customer data to fully understand their value to the business, and then you can allocate internal resources accordingly. This also means that you may not be able to continue servicing some customers.

  27. What customers do we need to attract?
  28. Customer data provides the strongest clues to what the customer requires now, but you must also find new ways of delivering for the future needs of the customer. This may involve products and services that haven’t been invented yet to customers you don’t have yet.

  29. How can we acquire the customers we need?
  30. Having understood present and anticipated customer needs, you need to educate your marketing, product design, and sales staff accordingly. Build targets and monitor relentlessly, demanding accountability from everyone in the sales process.

  31. What are my messages for our people? 
  32. Your values need to be made clear through documented indicative behaviours and by your own example of commitment and best effort. The present needs to be understandable and the future inspirational.

  33. How do we contain our costs?
  34. Your key processes should be systematically measured and regularly reviewed to ensure conformance to performance standards or targets set. Your aim is to continuously refine and improve. 

  35. Is the business where the customers need us to be? 
  36. It’s important to make decisions on what processes and skills are needed by each of your customer segments in each of their locations. You need to be electronically available and responsive 24/7, and physically accessible according to your product or service.

  37. Do our people know what is expected of them? 
  38. Make sure you’ve developed all the appropriate rules and procedures to direct the behaviour of all of your employees. These need to be incorporated in quality systems that are regularly updated and are instantly accessible to all workers. 

  39. Do I have the right approach to decision-making?
  40. Ensure your managers have the training, authority and autonomy to make decisions in order to achieve the best balance of customer satisfaction, ROI and safety.

  41. How can I motivate our staff?
  42. You need to help your team appreciate and articulate their purpose by giving them appropriate autonomy. Help them to develop and maintain mastery in their key activities, and the motivation will come from there. 

  43. What’s the best way to determine financial rewards and incentives?
  44. Negotiate market-competitive salaries and wages within the legislative requirements, and keep them constantly under review.

  45. How do I ensure safe work conditions and employee wellbeing?
  46. A CEO is also the chief safety officer. Design an appropriate support base of safety officers and ensure you have the procedures, clothing and equipment appropriate to your business.

  47. How do I stay inspired?
  48. For some leaders, it’s immersing themselves in their industry – reading, attending seminars, online training, mentoring, and liaising with their cohort – even in their downtime. Are you on top of major events for CEOs in your region? Have you considered mentoring? Inspiring others will in turn inspire you.

  49. Am I on top of staff training and development?
  50. Do a thorough assessment and provide education and training appropriate to the team’s needs. Your aim is to fully equip and enable your people to do the best possible job for your customers. Staff development helps attract and retain the best people beyond the usual turnover cycle. 

  51. Have we documented our core process for customer delivery?
  52. Make sure your process is tailored to each of your customer segments. You need to know and understand everyone in your business process sequence: from the supplier, to what value is added, to who is the customer.

  53. Do we have a secure store of all we need to know about our business? 
  54. It’s imperative that you use encrypted and protected data/information for performance measurement and planning, including financial, sales and marketing, operations, product and service quality, supplier quality and customer satisfaction.

  55. How do we know if our processes are up to scratch?
  56. You ask your customer, monitor their satisfaction, keep them informed of changes, deliver on effectiveness and efficiency, and search for innovation opportunities.

  57. Do we have a method for, and record of, successful innovation? 
  58. Strive for a systematic approach to benchmark your processes against best-in-class competitors, to improve operational performance and to create new ways of providing value to your customers.

  59. Are you still here?
  60. I hope so. Leading a business can be a joyful and rewarding journey. Especially when you ask the right questions.  

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