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How to be assertive while avoiding 'bossy' label
Saturday Star
|February 14, 2026
IF you’ve ever held back your true opinion in a meeting for fear of being labelled as difficult, or softened your emails to avoid sounding too demanding, then you know the exhaustion of the likability trap.
Taking a curious and open approach to resistance can shift the team conversation from opposition to collaboration.
(Freepik)
For many, the line between being a respected leader and being called bossy or aggressive often feels razor-thin. It’s also a frustrating double standard where the same behaviours that get your colleagues praised as decisive or natural leaders can get you sidelined as “not a team player”.
This fear of the bossy label also does more than just undermine your confidence — it slows your growth. When you hesitate to speak with authority, other managers and your executive leaders could easily mistake your caution for lack of a strategic point of view.
Here are some proven strategies for being assertive without being bossy, so that you can own your power without losing your authenticity:
Lead with headline
We often over-explain because we want to justify why we're taking up space. This is the wrong approach. In most leadership circles, long preambles and wordiness can be perceived as uncertainty. Senior leaders want your conclusion first so that they can process your recommendation immediately.
Think of it like this. Your headline is the bridge between your expertise and their attention. Keep in mind what’s in it for them so they have a vested interest in what you share next.
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