Home First Time Home Buyer FAQs What makes a strong leader? The women of housing offer their thoughts

What makes a strong leader? The women of housing offer their thoughts

The women of the housing industry took to the stage on Wednesday morning during the Women of Influence Forum to share leadership stories and strategies on the final day of The Gathering by HousingWire.

For Michelle Sipe, the senior vice president of operations at insurance firm SimplyIOA, one of the most important leadership lessons she learned early in her career was the importance of being humble. 

“I was thrown into an industry I knew nothing about as a leader. And one of the things I quickly learned was that taking a humble approach — and being honest in meetings that I didn’t necessarily understand everything — ended up being super positive,” Sipe said.

“It was definitely nerve wracking, but I think really grounding myself and recognizing that I don’t know it all, and letting the team help me and coach me, I think was one of the most important things I did.” 

Rebecca Thomson, the national vice president of Anywhere Real Estate, shared a similar experience. 

“I’m in change management, and what I’ve learned is that to get out of a situation, you can’t keep doing the same things. And you have to be willing to fail by trying something new and being comfortable failing,” Thomson said. 

Emotional awareness

Thomson discussed the concept of strategic uncertainty. This involves being OK with the fact that you don’t know everything that could happen while still preparing those around you for what could go wrong. This way, when something doesn’t go how you want, it isn’t a catastrophe. 

“For us, it is about accepting that those little failures are a sign of progress,” Thomson said. 

In a similar vein, both women discussed the superpower of empathy. 

“I’m hyperaware of my team and how to encourage and influence them,” Sipe said. “I’m really passionate about taking the time to learn from others, and I think there is value in that.”

For Thomson, a lot of the value in empathy is being able to find what makes team members tick, then using their passions and strengths to develop them into future leaders. 

Sipe and Thomson also discussed emotions and vulnerability, noting that while showing emotions may have historically been considered a weakness, they now feel that it’s a strength. 

As Sipe has looked to navigate challenging interactions and seasons in her career, she said that being aware of her emotional state has helped her to become a better leader. She said she knows when she needs to take a minute to regroup and is able to give herself grace when she’s struggling with something.

“It is something I am starting to see more of with you younger friends and colleagues, and I think emotions are starting to be more part of the conversation,” Sipe said. “I think being aware of how our passion about something manifests itself in our emotions and being able to express that is really important.” 

Similarly, over the course of her career, Thomson said she has learned that vulnerability is a superpower. 

“People don’t want to work with robots and I don’t want the people I work with to be robots,” Thomson said. “They have the ability to talk to our clients, joke about life, and it just gives people permission to be comfortable and be authentic.” 

Getting in the zone

As leaders look to level up, Sipe said one of the best things she has done is to create a dedicated workspace for herself. 

“I open that door and I just get in that zone that I’ve created. And then at the end of the day, the most important part is that I leave bad-ass Michelle in there and then I get to be a bad-ass mom on the other side of the door,” said Sipe, a mother of two young boys.

If people are unable to create a dedicated work space, Sipe suggested they have an item that helps them get in the zone and focus on work. 

Thomson said one of the keys to her success as a leader is her daily workouts, which she uses to amp herself up for the day. 

“When you are stuck, sometimes moving around or knowing the people that you can call to work through things is important,” Thomson said. “We can then lift each other up and get that reset we need.” 

For Thomson, her two top priorities are family and health, something she stresses with her team by setting an example of how to prioritize them.

“You don’t get that time back,” she said. “And it is also really important — especially with all the change that we continue to see — to focus on the things that you can control, and understand that there are plenty of things that you can’t control and you can’t influence, so you can’t fixate on them.”

Join us next year at The Gathering 2026 in Austin, April 27-30, as we once again build the most powerful room in housing. Industry leaders, like those featured here, will deliver insights you can act on and provide the connections that move your business forward. Register now to lock in our lowest prices.

First Time Home Buyer FAQs - Via HousingWire.com