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Diversity & Inclusion

How to Have Difficult Conversations at Work and in Life: Tips From Okta’s Maya Rashed

A couple weeks ago, Maya Rashed had a conversation with her four-year-old niece. They were talking about animals, as toddlers and their aunts are wont to do, and Maya asked her critter-obsessed niece if she would like to work with animals when she grows up.


"She looked at me and said, 'Oh, I want to stay home and cook like the mummies do,'" remembers Maya.

Maya, the Director of Demand Generation for Asia Pacific and Japan at identity and access management company Okta, was surprised by her niece's response. Especially since Maya and her sister both work. "She's definitely not getting those ideas from home. There's clearly something that's still embedded in society and making girls feel like that's their role," says Maya.

For Maya, who has built her career in the male-dominated world of software marketing and sales, her niece's response reminded her of the gender difference she sees when it comes to expectations in the workplace.

"It starts when you're a kid with gender socialization. The ways in which women are raised can interfere with their careers and how they're able to step into the workplace," says Maya. "Women are raised to be a little more risk averse, a little more fearful to have those tough conversations."

Maya, who is based in Sydney, Australia, now runs a team of 20 and works with direct reports across all of Okta's marketing initiatives, from corporate communications to business development. She's fought stereotypes and carved out a career that she loves, but it wasn't always easy, and she's had to overcome some of those gender stereotypes along the way. While she now regularly has tough conversations—whether it's advocating for a promotion, giving feedback to a direct report, or strategizing with a superior—she had to learn how to do it.

"I was terrible. I only recently became good at it," says Maya of leading high-stakes conversations. "It comes with confidence in who you are or what you do. I still have days where I ask myself, 'Am I doing an okay job?' Trust me, everyone does."

Maya has plenty of advice for other managers or leaders who want to improve how they have tough conversations. She's shared her tried-and-true tips with PowerToFly—advice that's valuable for both managers and for their direct reports.

How to have difficult conversations with employees: "come from a place of caring"

Maya's advice on leading tough conversations as a manager centers around four key themes:

  • Mindfulness. "Make yourself as approachable to your team as possible, even to people who aren't your direct reports." For Maya, that means being conscious about creating a two-way street for dialogue, actively making herself available for conversation, and being mindful that her direct reports are all humans who have lives, emotions, and issues outside of work. "When your boss can understand at least some of what's going on, that can help put things in perspective," she says.
  • "Come from a place of caring." Maya credits her current manager with changing her management style by showing her how important it is to put employees first. "In the past, when I've worked at big corporate organizations, I've felt like just a number. That kind of approach doesn't lead to loyalty."
  • Offer solutions and growth plans along with feedback. "I'm upfront, the way I'd want my boss to have a conversation with me, but I always say, 'let's try and work on this together, and this is what I'm going to do to support you,'" says Maya.
  • Transparency and directness. Above all, Maya advocates for transparency. "You've got to be straight to the point," says Maya. "If we're transparent, there's a whole heap of knock-on effects [like rumors or misunderstanding] that's avoided."

Over the years, Maya has developed a unique script for getting through situations that require giving negative feedback, and it goes like this:

"'Hey, I have some feedback for you. I don't want you to respond to it right now, but I want you to hear what I'm saying and take it away for a little bit. Have a think about what I'm going to say and then, maybe in a couple of days' time, let's discuss it.'"

Maya says this approach works because it cuts out someone's opportunity to be reactive or defensive and gives them an opportunity to compose themselves and plan a response before reengaging.

Planning ahead is also a key factor of how she has conversations with her bosses, too.

How to have a difficult conversation with your boss: "plan it out"

Whether she's advocating for more responsibility or leading a conversation about her career goals, Maya's learned that preparation is key to having a good conversation with a supervisor. This is what has worked for her:

  • "Remain respectful and plan it out." Maya says she always works through not just what she's going to ask for or try to get out of the conversation, but also how she's going to approach it.
  • Be honest. If you're struggling with something that's going on outside of work, be upfront about that. "People aren't often transparent enough with the realness in those situations," says Maya, "but if you work for a good company—which I'm hoping everyone does!—your boss will want you to be successful, too. You don't need to give your life story, but it's helpful to know what's going on in your life."
  • Come to the table with a solution. Maya says these conversations go best when it's clear that you've "put some thought into it" and recognized that it's not just your boss's responsibility to change or solve things. "Have a thought about how you'd fix it, and how you're going to participate in that process. If you do that with your boss, they'll definitely respect that."
  • "Ask for perspective and advice." Though it's important to approach situations with a proposed solution, Maya cautions against going in with your mind made up. "There might be other factors as to why something's happening or trickle effects that your boss can help you understand," she notes.
  • Set follow-ups. Being clear about next steps is key to actualizing whatever it was you discussed with your boss, says Maya. "Put it in an email saying, 'Hey, this is what we spoke about. This is what I'm going to do for my part, this is the support I'll need, and this is where I want to get to.'"

"It may feel like this is a lot of work just to have a conversation," Maya says. "But if it's a difficult one and something you really believe in and want, it's important to make sure it's clear."

Finding a work environment that works for you: growing at Okta

While these tips will empower you to have tough conversations wherever you are, Maya knows first-hand that they're much easier to implement if you're in the right environment, and she encourages everyone to seek that out.

After more than a decade in corporate marketing, Maya has found that supportive environment in Okta.

"My boss here has taught me so much about caring, about mindfulness, about the power of listening." says Maya. "There's none of that 'knowledge is power' thing, and every level of hierarchy at Okta is so open and approachable."

She's felt enabled to go into those tough conversations about her career growth with her boss (and her boss's boss!) because she knows a company value is to "really empower our people." For Maya, that's meant feeling comfortable enough to say that she'd like a C-suite mentor (and getting set up with a mentorship program the very next day) and getting to have a one-on-one with company CEO and co-founder Todd McKinnon to discuss her career path and growth.

"At the end of the day, that makes it really easy for me to picture myself here for years to come," says Maya. "I feel supported, I feel valued, I don't feel like a number, and I feel like I'm being taken on a guided path to where I want to be."

If Okta's work environment and values sound like the kind of place you'd love to work at, check out their open jobs here.

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