5 Challenging Questions A Leader Needs To Ask Themselves



When was the last time you experimented with something at work?

Maybe you got an idea for a new product. Doesn’t matter if it succeeded or not. Innovation comes from experimentation.

When was the last time you did this?

That long?

How do you expect to stay ahead of the game if you continue to sell or offer what you did last year? Two years ago? Five years ago? Longer? The recent collapse of Toys R Us reveals the danger of allowing your products to become obsolete, never mind anything else.

A related question is, what do you do to encourage your employees to experiment?

You see, if you’re experimenting, then you’re innovating. If you’re doing nothing or discouraging others from doing so, then you’re maintaining the status quo.

Think about what that actually means…



What five people have had the greatest impact on you in your current role?

Maybe you have to extend this reflection back over the entire time that you’ve been employed or have been working. If you’re struggling to think of five people, then you’re not trying. Everyone influences other people, whether it’s a little or a lot.

What did they teach you? Are you still applying those lessons? Fully? Consistently?

What five books have had the biggest impact on you in your role? What did they teach you? Are you still applying those lessons? Fully? Consistently?

Charlie Tremendous Jones says 'You will be the same person in five years as you are today except for the people you meet and the books you read.'

If you’ve not read much on Peter Diamandis, the Greek American engineer, physician, and entrepreneur, I recommend that you do.


Peter famously asks what your five-year goals are, and then asks how you could accomplish them in six months.

That may not work for you, but it stresses the need to focus your energies in such a way as to have the greatest impact. If you’re taking five years to make a difference on something that could be done in much less time than that, then you’re not pushing yourself. You’re cruising instead of working.

One last thought on “impact” – Decide whose lives you want to impact the most in the next six months, and then ask yourself how you will do that.



What does your organisation do to motivate staff?

  • Do you pay them a little more than your competitors?
  • Do you make sure that they work in a safe environment, that the facilities are warm when they’re supposed to be and cool on the few hot days of the year?
  • Do you promote a tolerant working environment?

And if you do those things, do you think that they will motivate people? If so, then you’re in trouble. People expect these things. When they get them they say, “I deserve it.” When they don’t, you demotivate them.


What motivates people?

Several things.

Challenging work is a big one. Are your staff bored? If they are, then you need to find out why and correct it. The longer you leave it, the more demotivated they’ll become.

The reason that so many people are bored is because they’re capable of so much more than what you give them to do. So you have to ask yourself how you can make their jobs more challenging for them. The answer probably won’t be easy to find. If it was, then you would’ve given that work to your staff already. That they’re bored means that you haven’t.

Maybe you don’t think that boredom is that big of a deal.

Here’s the thing. People who are bored can do their jobs without concentrating. When you fail to concentrate, you are easily distracted, and you make mistakes. In some jobs, this can cause serious injury or even death. In others, it can cost the company millions of pounds.

Britain’s low productivity seems to be a perennial problem. You can help to boost it by giving people work that will stretch them, and you’ll motivate them at the same time.

Another thing that motivates people is the opportunity to grow.

In an earlier article we talked about how the organisation could help employees to achieve their personal goals.

Their career goals are important, too. And as you’re probably not guaranteeing them a job for life, when you help them to develop professionally, you not only make them more qualified to work in your organisation, you also prove that you care enough about them to risk the possibility that they will take their new-found skills elsewhere.

That helps you to build trust - a rare commodity in the workplace today.

People are also motivated when they’re promoted.

The flatter hierarchies make this more difficult, but not impossible. Ask yourself this question: “What new position could we create that would use the enhanced skills of Employee X?”

Create that position, give it the pay that reflects the responsibility it carries, and then put that employee in that position.



Ask yourself this question: “How do you inspire others?”

Inspiration causes people to achieve more than they planned to or thought they could.

It makes them want to work harder.

What do you do that makes your employees want to work harder?

It’s one thing to order people to work longer hours. It’s quite another to find when people want to do it. And you have to keep an eye on this, however. You don’t want people burning out because they’re too dedicated.

You need to be the leader that not only checks to see if the windows and doors are closed and locked, but also that you chase out those who just want to work another half hour or hour before going home

Work isn’t home, and the two shouldn’t be confused.



Now pretend that you’re just starting your career.

Ask yourself, where will your organisation be in ten years? In 20 years? Longer?

It’s difficult to project more than a few years ahead because technology changes so rapidly.

The Internet, for example, only became available to the general public in 1991. And companies like Amazon, Google, Facebook, Twitter, and a host of others came later.

So another way to look at this is to pretend that you’re now at the end of your career. You see yourself on the home stretch; the last few weeks before you retire.


Ask yourself these questions:

1. What would you say to your 21-year old self?

At this juncture, you’re probably at the beginning of your professional life.  If you’re this age, then read some biographies of successful men and women who have already made their mark and see what wisdom you can glean from their experiences.

You should also seek the advice of those who are in their late 50s and beyond to see what they have to say. If you do this, then choose people who have done well in their careers, especially those who are at the pinnacle of what you think you’d like to do.


2. What would you say to your 30-year old self?

Thirty-year olds have probably had a least one good job already. They are starting to get a feel for the kind of work they’d like to do for the foreseeable future.

They may be married or be in a long-term relationship. They may even have children. Responsibilities like these make people want to settle down. What advice would you give to someone at that age?


3. What would you say to your 40-year old self?

At 40, you’re about two-thirds of the way through your working life. It’s true that some, certainly among the Baby-Boomers, who have no intention of retiring; but you can’t count on your health to permit you that luxury.

Maybe you’ve come to the end of an interesting run of jobs in one area, and now you want to pursue something else. What would you tell a 40-year old who wanted to do that? An MBA perhaps? A terminal degree?


4. And what would you say to your 50-year old self.

Fifty is not the end of your working life, though many organisations would like you to think that it is.

The late Sir George Solti, artistic director of the London Philharmonic Orchestra and many other world-renowned bands, lived to be nearly 85, though he was booked to conduct concerts many years past then.

That being the case, retirement is probably some distance away. What would you tell your 50-year old self about how to spend the next ten or twenty years?

You probably noticed that as you thought about each of these different ages, your perceptions changed.

And that’s a good thing because you need to think about your life like that. It can help you to plan your personal and professional development. Life seems to start out slowly, gather pace, and then race to the end.

The best time to start thinking about how you will spend your working life is at the beginning, though you also need to reconsider it at various times through your life.

This exercise is good for that. Thinking through your career is also valuable for helping you to mentor those who are younger than you, and it’s the sort of thing that you ought to train your managers to do, too.

The goal here is not to simply fill in some blanks. Instead it’s to help you think clearly about what you should do next and to help others do the same.

If you fail to do it, then you’ll drift. Wherever you end up will probably be different from where you wanted to be.



Five challenging areas. Experimentation, Impact, Motivation, Inspiration, and Orientation.

Each worthy of thought and introspection. Each with the potential to release greater talents from within you and from within others. How will you make the best of the questions and your answers?


If you would like to be challenged further, please – email here

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