How to show up as the leader your organization needs with Jean Olivieri

Leadership isn’t a static skill. In times of transformation - or when stepping into a new leadership role - it can be challenging to know where to begin. This week, I sat down with Jean Olivieri, who has held senior executive roles from midsize to Fortune 500 companies, to chat with her about how to lead change successfully - no matter what starting point your company may find itself in.

I’m excited for you to hear from Jean, whom I first met as a young person, trying to figure out how I wanted to show up as a leader in my own right. At the time, she was the only executive-level woman in our department, and she was (and still is!) someone that I admire for her ability to rally her team and drive results.  

“It’s not a cookie cutter approach to leadership.”

There are times of uncertainty during every stage of business, and it’s the role of the leader to motivate their people, even in the most difficult times. Jean says that it’s about understanding the individuals on your team. “You know what motivates one and not another, right? So if being present at high level discussions motivates somebody, and they love to present, and they love to do that, give them those opportunities to do that. It's not…a cookie cutter approach to leadership. You have to know your people really well. They need to know that you're in it with them… if there's any blockers, it's your job to move them.”

The best way to understand your team: talk with them. Work together to discover what those potential obstacles are and make a plan to overcome them together. When setting these new expectations for your team, readers of my newsletter know that making agreements is more effective than setting on-way expectations. According to Jean, “Nobody likes to be told what to do and then be criticized because what they did wasn't good… [Leaders and their teams] should say, ‘let's roll up our sleeves together and figure out what we want the end goal to look like here’.”

Ask yourself: What drives each member of my team? What actions can I take as their leader to ensure each person is performing their full potential? 

“Structure follows strategy.”

When building a new team (or revamping an existing one), Jean says that “Structure follows strategy.” Leaders should first consider the business objectives of the company then determine how their team needs to operate. “You don't necessarily go in thinking about how you structure the team. You have to go in and really understand and connect to the company's mission and goals.” Then behind that, you can build out what that structure looks like, making sure you have the best person in each role. Jean stresses that “talent always wins,” so where you “place heavy [strategic] bets, and you want to make sure that you have a strong visionary and executor in that role.”

For leaders building a team for the first time, know that you likely won’t be given the resources to build out your ideal team initially. This means much of what you’re thinking won’t be executed for six months, nine months down the road. New leaders will have a lot of internal selling to do, and Jean suggests beginning by hiring two or three people who are on the same page as you are. Then the three of you should consider what you’re trying to do, and you can build from there. “In any company I've ever worked for, nobody lets you go in and just hire a big team,” says Jean. “It's usually ‘hire two people and then let's see what we're going to do here,’ and then maybe they'll give you two more heads and then another two more heads. So you just have to constantly be saying, ‘okay, what's important now?’.”

Ask yourself: Given the objectives of my organization, what shifts could be made to more effectively align my team with our priorities?

“It’s a lot easier to build something than it is to transform something.”

Before you can know what kind of leader your organization needs, you need to identify the point of departure. In Jean’s experience, the start-up phase can be much easier than evolving a well-established function, saying “It’s a lot easier to build something than it is to transform something.” With the start-up phase, you can define your vision and get the right people in place from the beginning. This means you have team members with the optimal skills and experience to execute, along with buy-in for your strategy.

In contrast, when you’re transforming an existing organization, especially one that's been functioning one way for a long time, you’ll likely be required to make tough people-related decisions. You’ll have to identify who you can count on, and who may be preventing what you're looking to accomplish. This can be especially difficult if you're an outsider. “They don't know that you come from a place of good, that you're really just trying to make this a better place to work, streamline operations, do all that stuff. It's really hard to convince people that the way they were doing it before wasn't right,” says Jean.  

She reminds leaders that coming into a situation like this is a longer play. “You have to bring them in, say ‘you guys have been doing amazing work, but here's what the company is looking to do, and in order to do that for them, here's our contribution.’ And you'll have some people who jump on the boat and some people who don't.”

Ask yourself: What is your team’s present state or point of departure? How can you adjust your leadership approach to that situation? 

As Sir Richard Branson said, “Every success story is a tale of constant adaption, revision and change.” Your leadership should change and grow with time. With a deep understanding of the needs of your team and your organization, you can effectively lead through anything. 

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When your company grows, your leadership must do the same