Awkward questions every leader should ask themselves

Awkward questions to ask yourself

Is anyone following me?
The whole point of being a leader is to guide people towards a goal. If you are forging ahead towards your glorious vision but everyone else that you are going to depend on for this vision is milling around in confusion, you are likely to fail. In this case, you are not a leader; you are just a lunatic visionary wandering off on your own into the wilderness.

Why should these people trust me?
The relationship between leader and followers is one that is built on trust.

Leaders can’t do everything themselves. You have to trust that your followers will act to help you achieve the vision, even when you’re not watching over them. Leaders can’t see everything. You have to trust that followers will point out to you when you may be leading in the wrong direction.

Leaders also have to gain the trust of their followers. The followers need to believe that you are guiding them towards success rather than failure. They have to believe that your decisions are made in the interests of all rather than for selfish motives.

What do I need to learn here?
No leader is perfect. You do not enter a leadership role and become suddenly imbued with omniscience and infallibility. It is inevitable in a leadership role that you will face challenges that you are not prepared for, that you will have to make decisions with imperfect knowledge, that you will make mistakes.

As an effective leader you are pursuing a constant journey of learning alongside your journey towards the goal. This requires a certain level of humility. It also requires a willingness to celebrate your mistakes as learning opportunities and a willingness to expose your vulnerabilities to your followers. (And that’s another reason why you need a trust-based relationship.)

Who can I rely on to challenge me?
An insecure leader will view anyone who disagrees with them as a threat and will concentrate most of their efforts on defending themselves and neutralising the threat. They will surround themselves with yes-men and yes-women and leave themselves open to confirmation bias and dangerous blind spots.

If you are a secure leader who trusts your followers and is willing to learn, you welcome disagreement as an opportunity to test the robustness of your vision and your plan for achieving it. You will meet any challenge by looking for the truth in the other person’s perspective and looking for the flaws in your own.

What difficult things am I avoiding?
A leadership role can be a great opportunity to pass on all the jobs you hate doing to other people and to call it delegation. But leadership is primarily about taking full responsibility for results and for other people. With the pay and the power comes the pain.

The best question to keep asking yourself is “What can I do to help my team to get on with delivering value?” Sometimes it will be stepping back so that you can steer them in the right direction and sometimes it will be mucking in and getting your hands dirty to dig out the barriers to progress. Great leaders do what is needed, not just what they enjoy.

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About the author

David Winter is Head of Corporate Consultancy and Research at The Careers Group Consultancy, where they encourage people to ask themselves the awkward questions that will give them the best chance of growing and succeeding within their careers. David regularly trains other practitioners in advanced coaching theory and evidence-based techniques and has developed and delivered interactive workshops, thought-provoking webinars and innovative written materials on topics ranging from interview skills to strategic thinking. More blog posts by David Winter ››
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  • Sahan Wijesekara

    This is a very valuable discussion. I did realized that as a leader I have to accept both appreciations as well as hardships. Thank you for the value addition. Hope for the next article.

    Kind Regards,
    Sahan Wijesekara

    • Gemma, Citrix Interactions

      Glad you liked the post Sahan – thanks for your comments.

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