You’ve already met my Executive Assistant, Karen Montgomery. Now, let her shoot straight with you about how people in roles like hers should say perhaps unexpected and unwelcome things to those they serve. A tough topic treated by a wise woman. Enjoy. Learn. Apply. You’ll lead better for this!


They say great leaders are also great followers. Many of us, while leading our own people, groups, or organizations, also follow other leaders. So, in our roles as the “follower,” how do we best serve a leader? Specifically, how do we know when and how to give advice or feedback to that leader?

Someone told me recently that criticism is often interpreted as anger and that disagreement is often interpreted as dislike. Wow. That hit me hard. I grew up the fourth of five children, and you better believe I had to learn to speak up if I ever wanted to be heard! Criticism and disagreement were the bread and butter of the family banter. This has carried into my adulthood and so I’m rarely short on opinion!

Okay, so occasionally I’m asked for my input. Sweet. That makes it easy. But what about the times I’m not being asked? I think there are several considerations for determining when to speak up and when to hold our tongues.

Timing. If decisions need to be made quickly or your boss is short on time, that’s probably not the moment to insert advice or opinion. Instead, that’s the time for a sincere, “Yes sir. I’ll take care of that.”

The history. Is the matter at hand related to one you’ve previously handled? Are the stakeholders or the challenges or the circumstances similar to ones you’ve encountered before? If there’s a history or a precedent that relates to the current discussion, then a reminder is called for. Offer a brief history lesson for past decisions and the reasons behind them. We’re all forgetful at times and need a refresher about where we’ve gone before.

Ask permission. Before launching into your opinion and all the supporting evidence, ask your leader if they would like to hear your thoughts. Most of the time they will say yes. And this has the added benefit for setting the stage so your ideas will be heard.

When that opportunity arises, speak briefly, calmly, and humbly. Remember that disagreement is often interpreted as dislike for the person. Your boss might hear it as calling into question their identity. So keep any argumentative attitude or speech in check. Respect and affirm their ideas and direction and humbly offer another option.

Leave the criticism at the door. Remember criticism is often interpreted as anger, and you’re not angry. You’re just offering an opinion. Lastly, give them space to decide and then respect the decision.

Stephen often says those who challenge us, make us better. Part of your responsibility as a follower is to make your leader better!