It is fine to challenge your leader.

Arm wrestling challenge between competing with colleagues and foes.

It is fine to challenge your leader.

Be prepared for an unfavorable outcome.


I recall when I was hired by Cable & Wireless as the management accountant, the General Manager informed me that I would be in that role for a year and then I would be the financial controller. A year came by, and I was not made the financial controller and so when the job was advertised, I applied for it and copied the Labour Department. The financial controller at that time had no intention of vacating the post as his plan was to be in TCI for another five years. While Labour Department approved the labour clearance, the Immigration Board did not approve the work permit. Therefore, I got the position as Financial Controller. However, it was not easy as management did not expect me to apply. Management even wanted to send me to Bermuda. There were even talks about having the financial controller work remotely. I ended up being in that position for seven years and eventually became the CEO for seven years.

It is fine to challenge your leader.

I don’t see anything wrong with challenging leadership. Challenging leadership can be a good thing as it can keep the leader on their feet. Not because you have the title leader means you know everything, and everybody should not have to agree with you.  However, when it comes to challenging the leader for their position, it can be very tricky especially if the outcome is not what you expected.

Make sure you use wisdom when running against your leader.  While you are not obligated to inform your leader, I do suggest that out of courtesy and respect, you should let the leader know your intentions to compete against him or her. If you are unsuccessful and should you decide to stay in the organization, it will be awkward working alongside the leader.

Be prepared for unfavourable outcome.

Running for any position can result in a favourable or unfavourable outcome. You may think you may win but not everyone that says they support you will support you. Some people will set you up so be prepared that you may lose too.

Due to lack of trust and the human nature of an individual, be prepared that you may risk losing your position or your duties and responsibilities may be reduced.

Overcoming leadership challenges

In the private sector, it is not easy to fire your colleagues but in politics, the Premier has the right to fire any of the ministers. However, is firing the best option? What if other members challenge you, will they get fired too?

Based on my experience, it is hard working with someone you do not trust, especially if that person tells you one thing and does something else. However, leadership should not be just about you, it should be what is best for the organization.

If someone in leadership contributes successfully to an organization, invite an independent person to meet with both of you to have a frank and open discussion. Try to work things out and move on. Everybody deserves a second chance.

Another way to overcome leadership challenges is to stop making decisions on hearsay.

Finally, do not be anxious about anything. Be patient.


No one should be afraid to challenge a leader. If you don’t agree with something, you should have that right to say so. Likewise, if you want to run for a leadership position, you should have the right to do so as well.

However, whatever you do, make sure you are transparent and honest. Lack of trust and lack of communication can destroy you.

In the end though, we must learn to love and forgive.

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