Vol 10: Leading with encouragement

We all know it feels good when someone encourages you.

Or do we?

I’ve done a lot of presentations to upper management in my career. Almost always, after we’re done, we hop on a debrief call with a middle manager who tells us how great it was and what an amazing job we all did. But the thing is, while that technically qualifies as encouragement, it doesn’t feel encouraging. It felt like that person was grateful that we made them look good and worked hard, but that’s a far cry from truly seeing a person for who they are, and encouraging them.

When I think about moments at work that were truly encouraging for me, I think of things like…

• The time an executive pulled me aside to ask how I was doing and showed me how they had bookmarked the guidelines I created on their own computer

• When a co-worker quoted something I said in their Slack post, giving me credit for an idea and tagging me

• When someone who was in a training session at work posted on LinkedIn about how much it meant to them

Encouragement is tricky, because so much of it comes down to doing it at the right time, and doing it in a way that is meaningful to the person you’re encouraging. But maybe we're making it harder than it needs to be.

If you're concerned that the way you want to encourage someone may come off as dishonest or fake, odds are it's going to come off as genuine and meaningful. People who are dishonest or fake never worry about that. They say those things because they feel like they have to, or think it's part of their jobs.

Your concern and desire to encourage people in ways that resonate with them will actually help you do that. There's some real psychology behind this. If that's not enough, here are some other things you can ponder to help make your encouragement meaningful.

Ask yourself whether you're doing the encouragement for others or for yourself. In the story of the executive presentations earlier, the middle manager shares encouragement because they feel better after the big meeting and they personally benefitted from the work in question. Meaningful encouragement seeks to lift up someone simply because they're amazing—it's not connected to the encourager's success. A more appropriate thing for the middle manager to express in this case might be gratitude to the people who jumped through hoops to help them.

Be specific about what you're encouraging. Saying "nice job leading that meeting" is very different from pulling someone aside and saying "the way you shared your personal story at the beginning of that meeting was so well done and powerful—I think you really helped everyone else open up and share." We often take the easy way with encouragement, but it can mean so much more to tell someone exactly what you noticed and what it means to you.

Make it a regular practice. Even saying small things like "you've got this" or "I know you'll do an amazing job" help other people find confidence and feel better. Going deeper by recognizing skills and traits about them will help even more, like saying "you're such an effective speaker, I'm sure they will love hearing what you have to say." When people start to hear it more and more from you, it will start to feel less strange or unexpected.

I'm writing about this and practicing it because I'd love to live in a more encouraging world. We all have the power to make that happen, and I hope you'll give it a try. I know you can.

Real leaders: Bonnibelle Chukwuneta

Each month, I ask a leader in my own life to share who they are and what leadership means to them.

Bonnibelle describes herself as a writer, entrepreneur, and big sister.

Here's how Bonnibelle thinks about leadership, in her own words:

My leadership approach is one of leading by example. As the eldest child and daughter of Nigerian immigrants, I had to inspire those around me to help them achieve their best, and it’s a behavior that’s followed me throughout my career as a writer and manager. Whether it’s holding yourself accountable, encouraging open-mindedness, or being a better and kinder communicator, anyone and everyone can demonstrate “do as I do”.

Thanks, Bonnibelle.