Good morning,

Craig Wortmann has a question for you: What are some of your acts of boldness at work?

Maybe you’ve asked for a promotion, or a raise. Maybe you volunteered to lead a big project. Or perhaps you are pushing for a new office policy or way of doing business. That’s great! Now Wortmann has another question: how often do you do these things?

If you’re like most people, probably not that often, says Wortmann, a clinical professor of marketing. Because boldness is hard. Today we’ll get some advice from Wortmann on how to get better at being bold so that you feel more comfortable asking for what you want.

How to Get Getter at Being Bold

Think about something you want at work: something that’s a stretch, unlikely to be simply handed to you; something that you’ll need to persuade others to give you.

When you want something like this, you should be bold, Wortmann says. That doesn’t mean barging into your boss’s office to make your demands. Instead, it means being intentional about how you make your ask. He offers tips in this episode of The Insightful Leader podcast. Here’s some of his advice:

Schedule the time to talk: Because boldness makes many of us uncomfortable, we can be tempted to bury our request in another conversation. Don’t give in to this urge. Instead, “Have you called a time-out and structured a conversation that is only about this? It’s not in the flow of work, like, ‘Oh, by the way ...,’” Wortmann says. “Slow down for a nanosecond and make the conversation concrete: ‘I would like to talk to you about this and only this for the next 15 minutes. Can you give me that time? And I will do my best not to insert other stuff that we’re working on in here to muddy the waters.’”

Prepare for resistance: It’s not being bold if nobody’s resisting, right? So Wortmann advises that you come in ready to address that resistance head on. If it’s a skill you’re lacking, perhaps you explain that you’re taking a class on your own time to develop it. Or if it is failure that your boss is worried about, you can point to the last time you were able to overcome an obstacle that has tripped you up in the past.

Find the right balance: This piece is crucial, Wortmann explains. Know what level of boldness you will need—maybe think of it on a scale of 1 to 10. And then make sure that you’re balancing that boldness with warmth and humility. Because boldness on its own can make you come off as a jerk. And that’s unlikely to get you what you want. (Plus, most of us don’t like being jerks, which may be why we often shy away from boldness in the first place.) In these moments, leaning on honesty can go a long way. Wortmann describes this as, for example, “our ability to just say, ‘I’ve tried this a bunch of times. I feel like a couple of times I’ve let you down and the team down. Here are the lessons that I’ve learned. I’m ready. I’m ready now for a leadership position. Do you agree with me?’ Notice how I transitioned from humility to boldness. That’s what it is.”

You can listen to the full episode with Wortmann here.

What Could Russian Cyberattacks Look Like for American Companies?

The U.S.—and much of the world—is imposing strict sanctions against Russia for its invasion of Ukraine. Many experts believe Russia will retaliate with cyberattacks. Insight spoke late last week with former National Security Agency Director Adm. Michael Rogers, who served as commander of the United States Cyber Command. He is currently a senior fellow and adjunct professor at Kellogg.

Here’s part of what he said businesses might start seeing:

“They could experience ransomware attacks, denials of service, network degradation, and lockouts, for instance.

Certain organizations should be on particularly high alert for these attacks. For example, if you are a company or a brand that is uniquely associated with America, like Coca-Cola or McDonald’s, you are an extension of America to the outside world. Those companies should be thinking about whether they’re prepared to deal with significant cyber activity directed against them. And that’s because targeting those companies sends a broad message to the U.S. government—not just to the company.

If you’re a company that’s doing business in Russia, you also probably have a little higher probability of being a target of a cyberattack. In addition, I think Russia will be looking at the government, the military, and economic infrastructure, like if you run a pipeline or parts of an electrical grid. Major financial institutions are probably also a major target.”

You can read the full interview with Rogers here.