Dear Leaders

A weekly letter with actionable leadership ideas.

Leading with Assertiveness

By Hamza Shayk

Dear Leaders,

Ever had that nagging feeling in a meeting? The one where you know you should speak up, but there’s this invisible force pushing you back into your chair? Maybe it’s fear. Maybe it’s insecurity. Or perhaps it’s just Monday morning blues. Especially if you’re a New York Giants fan.

Let’s call that force what it truly is: a lack of assertiveness.

I come across too many executives who want to grow as leaders yet lack the appropriate amount of assertiveness and, due to the uncomfortable nature of it, avoid working on improving it.

Know this: The more refined your assertiveness skills, the more effective you are as a leader. I’ll even say that unless you master assertiveness, your growth becomes stunted to the degree that none of the other skills will increase your effectiveness as a leader. There’s no getting around it.

So, what really is assertiveness?

It’s the ideal middle ground between timidity and aggressiveness on each extreme. In this context, timidity refers to passivity or a lack of confidence in expressing oneself, while aggressiveness indicates overbearing or forceful behavior. Not assertive enough and you’re flirting with timidity. Too assertive and you can easily come off as aggressive. As a leader, you can’t afford either.

The Real Cost of Not Being Assertive

Loss of Respect. If you don’t stand for something, you’ll fall for anything. Leaders who don’t assert themselves lose their team’s respect. Leadership requires direction. Without assertiveness, direction wanes.

Missed Opportunities. Decisive moments need decisive leaders. Hesitation or uncertainty costs opportunities, time, and resources.

Team Confusion. Without a clear voice at the helm, teams flounder. They need guidance, clarity, and decisiveness. An absence of assertiveness creates ambiguity.

 Assertiveness in Action

In Team Discussions: Leaders must guide, not dictate. When a team member shares an idea, an assertive response might be, “I appreciate your input. Let’s explore its feasibility.” This acknowledges the contribution while maintaining the leader’s guiding role.

In Conflicts: Disagreements are inevitable. Instead of avoiding or dominating, tackle issues head-on. Say something like, “I understand where you’re coming from. Here’s my perspective.” This approach respects both sides of the argument. On the other hand, an approach such as “This is how we’re doing it. End of discussion.” shuts down dialogue, breeds resentment, and stunts innovation.

In Decision-making: Leaders make tough calls. An assertive leader might declare, “After considering all factors, this is our best course of action.” Clear, decisive, and grounded.

The Rewards of Mastery

Empowered Teams. When you assert yourself effectively as a leader, you empower your team. You serve as the “rock” that your team can rely on. That sense of security leads to stability at the very core. And, naturally, teams with a strong foundation have more cohesiveness and perform better all around.

Clarity. Decisions get made. Paths get chosen. Progress gets tracked. The ship sails smoothly.

Respect and Trust. Your peers and team members can discern if you’re the type who speaks up and honestly, or if you’re the kind who remains silent only to speak behind others’ backs (I see this too often also). Don’t be the latter; if you gain that reputation your days as a trusted leader are surely numbered.

In Conclusion

So, what do we do about it? Do we sign up for an “Assertiveness 101” class? Maybe. There are also plenty of good resources online, including some assertiveness workbooks that you can get started on. But real change starts with a simple shift in mindset:

Value your voice. Recognize that you bring something unique to the table – a different perspective, a new idea, a dissenting opinion. Let it be heard.

Next time you’re in that meeting feeling the weight of that invisible force, dig deeper. Find the courage to say what you have to say and say it, not in a bulldozer fashion but in a manner that’s firm and respectful.

I assure you, how you’ll feel by speaking up will outshine that feeling of regret that is oh-so synonymous with timidity.

At the very least, you’ll respect yourself more. At best, well, the possibilities are endless.

Wondering if we're a fit? Me too. Let's find out:


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