4 Statements Leaders Need to Be Saying More Often

Charlie Gilkey
2 min readOct 29, 2021

A client of mine is going through a catalytic shift in her career where she’s bringing on someone to manage her current business while she’s moving on to manage someone else’s business. It’s going to be a challenge, especially with learning how to shift between founder-CEO in one business and managing director in the other.

After a bit of her tail-spinning trying to figure out things she can’t know yet, I reminded her that this was a completely new journey for her. The goal right now isn’t to have it all figured out, but to learn to practice new ways of being.

Since she’s an extroverted social processor, I told her that she’s going to need to get used to saying the four following phrases:

1. I’m sorry. She’s going to make mistakes, stay in one context when she needs to be in the other, or drop some balls.

2. I don’t know. In this new situation, she won’t know what to do. Having a brand new manager for her business and being a manager for someone else’s business will both be new to her. Rather than stressing about not knowing, she can just be honest that she doesn’t know how to do it at the moment.

3. Let’s figure it out together. This one’s meant to avoid her falling into her old patterns of figuring out everything when she has a manager who’s there to help her and is actively taking her old job from her. She’ll likely be able to use it with her new boss, but in that context, she’ll be the one helping her boss work learn how to lean on her more.

4. I need to let this go. She’s going to hold on to parts of her old job that’s not hers — especially the worries from that old job. Her manager knowing that she needs to let it go helps her manager jump in and help. For her new boss, it’s more likely that she’ll forget which context she’s in and step into her boss’s lane.

The statements fit together nicely, depending on the situation. She may need to let something go, feel sorry for letting it go, not know how to let it go, and then need to figure it out together. Or maybe she’s sorry that she doesn’t know. You get the point.

I was able to share the four statements with her quickly because they’re what most leaders need to be saying a lot more. Her context is unique, but the challenges are universal.

But there’s another statement she (and we) need to practice saying more that deserves its own essay. Stay tuned.

This post is part of a series of “atomic essays” published on Twitter. The previous post from this series about writing techniques for getting un-stuck.

Charlie Gilkey

Author of Team Habits - http://www.productiveflourishing.com/team-habits/ - and the best-selling Start Finishing. Executive coach, investor, and philospher.