Leadership Moments: Taking Big Risks is Hard. Here’s How to Make Them Easier.

Over three decades in business, Nina Link has held numerous roles as CEO, president and board director in the media business, including as the longest-tenured CEO of the Association of Magazine Media. She is also a colleague of mine at The ExCo Group, a senior leadership development and executive mentoring firm that I joined last fall. In this “Leadership Moments” interview series, I’ll be focusing on key lessons that executives have learned during their careers.

Here’s the conversation I had (edited for space) with Link.

Q. You’ve been a mentor for four years. What are some patterns you’ve seen?

A. A big one is that many people are risk-averse because of this incredibly uncertain business environment across almost every sector. They may have strong leadership skills, but if they’ve built their careers in a legacy business, taking risks – doing something bold, rather than making incremental changes — is something they are uncomfortable with.

Q. So how do you talk to people about risk?

A. I love the saying, “change or die.” But then I really help them break down the possible consequences of a decision. What’s the downside? What’s the upside? And what happens if you don’t make a decision? I also believe in not putting all your eggs in one basket, but throwing a number of ideas against the wall and testing them before making one big leap. If you don’t fail sometimes, then you’re not really a leader and your organization is not going to be successful in the longer term. You learn so much from failing, but people really struggle with that.

Q. To take those company-wide risks, people in different departments have to work together in new ways. How do you do that?

A. You set the vision, and you are the cheerleader. You bring as much clarity as you can, even though there are a number of uncertainties. You communicate a lot, and you mix up teams, even at different levels. That helps develop new leaders. Companies can be very siloed in their decision-making, so when you put different disciplines and talents together, you can come up with something far more successful.

Q. And once you have those new ideas, what’s your best advice for getting them off the ground?

A. People often don’t know how to develop champions to help them do something bold. You have to be able to enlist people who can see the new path and help you move forward. When you’re not alone, it can make a big difference in risk taking. There’s a lot of fear of failure, with people concerned that making a mistake will affect their career.

I also use tactic that I call “pre-bickering.” It’s sort of like planting seeds. You have to know who’s going to give you a problem and won’t be on board before you present an idea. If I knew there were certain issues that some board members were going to object to, I would meet with them first and I would say, “This is not going to be something that you’re going to fully embrace. I think it’s best for the industry and here’s why. I’d appreciate any support you can give me.”

And then I would just hear them out, so that by the time we would get to the meeting, they still might not like the idea, but they won’t sabotage it. And if you can engage them early in the process, they may even start to think it’s their idea.

Q. Tough conversations around performance are always hard for managers. What advice do you give people on how to handle them?

A. One of the most powerful things I use has been an ExCo tool that helps people clarify the distinction between delegating and empowering. When a manager tells an employee they are delegating something to them, it means they have much more interaction to make sure the work is getting done and there are more check-ins. Empowering is when you’re really giving someone much more authority and control. You still have check-ins, but that trust has been developed.

Q. What are some other challenges you’ve seen?

A. Across the board, people are almost drowning in work, without the time to be able to stop and think and be strategic. They are pulled in so many directions. A lot of it is because of how they’ve organized themselves and how they work with their direct reports. Many of them have been successful doers and they are really struggling with how to move into that real leadership role, and have others do the work.

People also need to know what they’re supposed to be doing, and I’m always surprised at how often people don’t know where they fit in. I’m known as the Queen of Context. You need people to understand why they’re doing what they’re doing, to take them along on the journey. So many times you’re just told, “this is your project right now,” with no idea really of how it fits in the bigger scheme.

Q. Have you always been the Queen of Context?

A. Yes. I was a writer and also a systems analyst. I’m a left brain-right brain person, and I can’t function well without context, so I’ll just keep asking questions if nobody gives me the context.

Q. Did you have to navigate some gender headwinds earlier in your career?

A. Oh, yes. In the media business, it used to be all men at the senior levels. At first, I would get upset about how they would kind of pat me on the head for being a nice woman. They didn’t know how to talk to me in a business meeting, and even in a social setting they would talk about their wives. They were so uncomfortable.

So I used humor a lot and it worked really well. I would make it more lighthearted. If they said something off-key, I’d say, “Oh, did you really mean that?” I would not get outwardly upset about it, and I earned their respect over time. But it was hard. You thicken your skin. You figure out how to work with it. I’m a people person, so I can always find a way to make a connection, but it’s work.

Q. What other advice do you give women about surviving and thriving at work?

A. I find that many women say there are aspects of work that are not fair, whether it’s the pay or the assignments or the work environment. My feeling is that if want to continue working there, you have to figure out how to navigate the politics, find ways to promote yourself and ask for what you want. You have to connect with people in the organization at senior levels so they know who you are. You also have to volunteer for certain things to get more visibility.

You have to be astute and see where the opportunities are and where you can shine with the strengths that you have. Many women think they’ll be recognized if they do a good job, but stepping up and stretching yourself is a good thing. I talk to a lot of my female clients about helping them understand their value, how to present their value, and how to negotiate.

Q. Where did you get your drive to be a leader?

A. Starting in grade school, I’ve always had a vision of how things could be better or different, and I was always able to step up. I love to work with people and I’m willing to do the hard stuff.

I’ve put my hand up for things that I knew I wasn’t totally qualified for and I’ve had some flops, but I also was able to move up. I’ve always been interested not just in what I was supposed to do, but in other things where I could bring value.

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