When and how to disagree with bosses or other influential people at work?

Alexander Shevchenko, Chief Legal Officer at WEB PAY, shares a practical framework for dissenting with influence. He outlines how GCs and senior in-house lawyers can challenge powerful stakeholders constructively – protecting trust, credibility, and business integrity in the process.

To disagree successfully without causing affective conflict and other adverse consequences, it’s important to:
(1) correctly detect situations that require raising objections;
(2) employ the techniques of disagreeing respectfully.

In some cases, speaking up is vital, while in others staying quiet is a better option.

How to determine when to disagree?

You have clear business reasons for objections (e.g., the proposed action lacks efficiency or puts the company under undue risk).
If you disagree because you personally do not like the proposed action or the proposing person, then stay silent.

The impact of the proposed action on the company or the team is substantial.
If it significantly influences business, corporate performance or culture, then raising an objection is appropriate.

You have assessed the likelihood of adverse consequences of speaking up or staying quiet against the benefits that disagreeing can bring.
Consider the circumstances, company culture, the personality of whom you are going to challenge, how they are likely to respond, and your relationship with them.

You have considered what others think.
The more people are likely to support your opinion, the more likely disagreeing will be successful.

“In some cases, speaking up is vital, while in others staying quiet is a better option.”

How to dissent respectfully?

Prioritise disagreeing in private over doing so publicly.
Challenging in private is less likely to provoke resistance.

Utilise such communication techniques as:
– being confident in what you are saying;
– positive non-verbal communication (eye contact, gestures, and voice tone);
– careful choice of words (be diplomatic, don’t criticise, explain the value of your ideas modestly);
– showing respect for the person’s proposal and, if applicable, representing your idea as a means of developing their proposal.

Ask for permission to dissent, e.g., “I have a different opinion. Would you mind if I share it?”.
Giving the person power to decide mitigates the risk of a negative reaction.

Rearticulate their position.
Restating will assure the person that their point has been understood.

Clarify the “why” behind the objection (concisely communicate the business reasons for disagreeing).
A position that offers a solution and is justified with evidence, examples, credible sources, and logical arguments has force.

Ask for their feedback regarding your position and welcome input in improving it. Be flexible.
Further discussion may lead to a win-win solution or a compromise.

Recognise their position, e.g., “This is my opinion, but it’s up to you to decide”.
This will reaffirm respect.

Finally, it may be reasonable to discuss with your bosses the process for challenging their opinions. e.g., “There might be cases when I will disagree with you. How would you like me to share my viewpoints?”.

What tactics do you use to object to powerful people’s ideas at work?

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