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When considering assertiveness in the workplace, what are the actual parameters? What does it entail for women and why is it a topic of discussion?
Oswald’s Women’s Leadership Council hosted Kelly Keefe, President & CEO at ERC, to share her insights on these questions and how they should apply to Oswald Companies.
Kelly opened the discussion by asking “What does being assertive mean?”
One definition includes, “Standing up for, or expressing, yourself without physically harming another person or their feelings.”
Kelly added that assertiveness should also include:
- Authenticity: If you don’t take this opportunity, someone else will. Always start a discussion with the end in mind — with your clients, boss and peers.
- Win/win: Both you and the other person involved have feelings. Give friendly advice and embrace any feedback.
To change your habits for a win/win, Kelly went on to share these 11 tips:
Define what assertiveness means to you
- Write it down and understand where you fit on the map.
End relationships that are not working
- It’s okay to move on to a new position, department or job. Don’t go home miserable each night.
Don’t believe everything you think
- Change your negative soft talk. We all do this. Train yourself to turn off the negative talk.
Find a role model
- Take this seriously.
- Find a role model from a different generation. You’ll be amazed what you can learn from each other.
Resolve conflicts
- Someone has to do this, so why not you?
- Demonstrate the power to be the one to do this.
Speak Up
- Someone has to do this, so why not you?
- Someone needs to hear you!
Express your feelings
- Don’t permit bad feelings to fester for months or even years.
- Do this in a timely manner. The receiving person will respect your candor.
Quit apologizing
- Stop saying “I’m sorry.”
- Own your mistakes. This is a sign of character & people will take you more seriously.
Get straight to the point
- Respect the other person’s time.
- Don’t apologize before and after your point.
Talk for yourself
- Don’t expect others to speak for you.
Welcome and be respectful of feedback
- Feedback is a gift and should be regarded as such.
- Receive it in a positive manner.
Kelly closed her talk with comments from Oswald’s Bob Klonk, Chairman & CEO. Kelly asked Bob how he defines assertiveness at Oswald. Here’s how he responded:
- Be a leader without a title.
- Everyone can get better each day.
- Don’t be afraid to ask.
- Show others by your actions.
- If you think there is a glass ceiling, break it.
About the Author:
Michelle Mindell is Senior Client Executive and Team Leader in Property & Casualty at Oswald Companies.
The Oswald Women’s Leadership Council was created to empower, develop, and advance Oswald employee-owners, in support of professional and personal development, and an inclusive environment that advances the success of women and the organization.
This event occurred in 2018 and the article was updated in 2025.
