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These are the questions all leaders should regularly ask themselves

Our advice columnist takes on the universal question of what makes a great leader.

These are the questions all leaders should regularly ask themselves
[Image: HS3RUS/iStock; nanmulti/iStock]

Editor’s Note: Each week Maynard Webb, former CEO of LiveOps and the former COO of eBay, will offer candid, practical, and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at dearfounder@fastcompany.com.

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Q. How do you think about leadership and culture and inspiring people?

—Executive at a software company

 Dear Executive,

As a leader, you must be someone who can both be counted on and who people want to be with.

There are all sorts of leaders, from command-and-control leaders who bark orders and expect everyone to toe the line, to inspirational “servant” leaders who put the entity’s needs above their own. The most inspiring CEOs are committed to changing the world, and they are able to do so by putting the destiny of the company ahead of their own ego or needs. (Where it gets really tricky is being able to simultaneously take care of all the entities that they are part of—their company, their family, their team.)

Your leadership style is personal; it can be approached in different ways. Yet in order to determine if you still deserve the role, every great leader needs to examine their performance and periodically ask themselves:

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  • Am I driving/leading the company forward, or am I holding it back?
  • What unique contributions am I making to the success and future of the company? Would I rehire myself? Why?
  • Am I getting managed into compliance by the team? Or am I challenging the team to get to previously unimagined capabilities?
  • When I do challenge the team and then later look back with hindsight, was pushing them the right thing to do, or did it cause unnecessary churn and a failure to reach the desired result? Why?

Sometimes, when you’re tired or overwhelmed, you need to harden your resolve and dig deeper. I have a lot of belief in real leaders and their willingness and commitment to do the unthinkable. However, if you no longer have the burning desire to take on the challenges and responsibilities that come with the top job, you may need to put the company’s success ahead of your own.

Being a leader is hard work, and it requires tons of personal sacrifice. When you are thinking about leadership, you should also be thinking about leaving a legacy, which means thinking beyond yourself. Here’s what you do have to think about:

  • Have I codified the secret sauce that makes me special?
  • Are my values inculcated firmly? Have I taught people how to modify them when needed?
  • Do I have, at the ready, successors who can carry on the mission (and hopefully improve it)?
  • Have I embraced servant leadership? Have I put the cause ahead of my agenda and beliefs?
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