Insights 15: Challenging the boss / hierarchy - Recipe for disaster or true leadership?

“Conformity is the jailer of freedom and the enemy of growth” John F. Kennedy

“If it doesn’t challenge you, it won’t change you” Unknown

"Don’t show up to prove, show up to improve” Simon Sinek

Context for reflection:

Recently, I have been asked about the futility of challenging the boss or the organisation. It is a vexing question in organisations resistant to change and managers threatened by leadership. There is no easy answer, but what’s the choice?

As one person put it: “we were asked to work on a project, we spent late hours, early mornings only to find that, in the final analysis, senior managers made the decision prior to considering our input, without clarifying.” Clearly deflated and feeling a sense of mistrust, the group lamented that it was career limiting to challenge openly. It was better to remain silent.

I asked whether anyone had asked how or why this had happened. Answers were vague and based on assumption.  As a group, we agreed that it takes courage and honesty to seek the truth. It may not be popular or the “done thing”, and so often the unspoken becomes the lie we live with. …and sometimes this is convenient but shows our fear of a better way. Try the difficult conversation. When approached with the right intent it may lead to a “aha” moment for you and the other person. Leave it and live with the assumption, which if communicated to others, becomes our way of doing things – our culture. Challenging constructively is a key to leadership that takes respect for the other and courage in self. The truth may also test our understanding of the boss and hierarchy. It requires courage to not merely be the recipient of instruction but to enquire, seek to understand, and influence step by step. Start with patience and belief in yourself. And consider the alternative, to back off and live with a sense of futility based on assumption. In this space we lose as individuals, the team lose, and the organisation doesn’t learn. It’s not a choice, if we want to lead.

A few question to contemplate:

• Do you understand your leaders and their goals?

• How does your leader see your communication? Does it resonate with his / her style?

• Do you negotiate a supportive boss relationship that enables you to challenge?

• How can you approach the elephant in your room? 

Drafted in all humility as I continue my journey of discovery. It is indeed challenging, with so much to remember and learn.

Andrew Pons

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