Nurturing Connections with Approachable Leadership

Up next in our “Lieutenants - Lessons, Learning and Leadership” blog series is Angela Grady, EVP and Chief of Staff at Okta, a cloud company known for its Identity Management platform. Okta is playing a big role in the transition to a digital and globally distributed workforce. Angela has worked alongside some of the most impressive names in the tech industry: Steve Jobs, Scott McNealy, Marc Benioff and now, Todd McKinnon. While each of these leaders is known for their own style and legacy, Angela is known for her openness and ability to GSD (get shit done). She is the epitome of a lieutenant and is mentoring a new generation of leaders and lieutenants. In this Q&A, Angela describes why being an approachable, team-first leader is essential to execution and how nurturing the relationships you build leads to the greatest successes.

How would you describe your role? I’ve been at Okta for 6 years now. I came in to run global operations and then a couple of years ago, Todd asked me to be his Chief of Staff. I break my responsibilities into four buckets. The first is partnering with Todd on overall company execution, driving results, alignment and collaboration across the company. The second bucket is working with the board of directors to ensure they know what’s going on and understand the essence of Okta so they can contribute to our strategy at the right levels and with the right context. The third bucket is around the voice of the employees and customers, or what I call ‘field trips’. Taking Todd out to our offices all around the world so we can hear from our employees and visit with our customers, and understand what the issues and opportunities are in the various regions. Then the fourth bucket, my own personal passion, is leadership development and company culture. It's really challenging to hold onto a culture and have a set of values that you hold true to at a high growth company. It begins by setting the tone at the top, and then developing our leaders to embrace and uphold our culture and values.

Tell me more about the Board of Directors piece. A lot of CEOs want to micromanage the board and manage every piece of messaging, yet what you describe sounds like more of a nurturing role, and I think that’s relatively unique.

You're right about the micromanaging part, but Todd and I have a different perspective. I attend all the board meetings, and am responsible for keeping them updated on what's going on in the business and being a resource for them in between those board meetings. We've created a portal for them so they have the materials and information they need on hand to provide the right counsel and guidance when the time comes. Transparency and trust is key. Todd doesn't sugar coat things for the board. It's not the way he interacts with them, so I think he's very comfortable letting the communication flow and giving them that broader 360-degree view of the company.

How would you best describe the traits that make a great lieutenant?

I think one of the traits of a good lieutenant is being approachable and collaborative. Often a CEO is scary just by virtue of their title. It doesn't matter how open or straightforward they are. I’m here for those who may need guidance or just want to talk through an idea in advance of meeting with Todd. If you put up a wall or don’t open yourself up, you will have a harder time building those bridges and relationships across the company that are fundamental to being able to execute well. It's also important for achieving cross-functional alignment.

If you don’t open yourself up, you'll have a harder time building those bridges and relationships across the company that are fundamental to being able to execute well.

Another trait is a relentless focus on execution. Your ability to keep an eye on the ball. If you're lucky enough to have a killer market opportunity, it’s really important to know how to execute properly. To identify what the priorities are and keep people focused on those. This also ties back to approachability. If you can go to the depths of the different parts of the organization and gain people’s trust, it's a lot easier to identify gaps, get everyone aligned, and get the resources needed to better execute.

How would you say you achieve that approachability?

I seek out relationships and I try to leave my own ego at the door. If you can learn to let your ego take a back seat and just be a good sounding board, it's amazing how much more you learn and the relationships you can create. But you also need a point of view. You're not just there to take it in. But you can still have a strong point of view without shutting others down.

How do you handle or filter everything that comes at you in a role like this?

I could do a better job of that, to be honest. I let a lot of things through my filter that I maybe shouldn't, but I’m still very focused. I want to hear the input. If you say no too much, people won't bring you ideas and they won't seek you out. It's really important to form your theories by seeking input and feedback from the people who are actually doing the work. If you shut yourself off from that, or you somehow take an attitude that you know more than that person, no one wins.

How do you manage stress personally? What tips would you share with others?

The most important thing I tell people, especially young women who are considering having families and questioning how they will balance their lives, is that an organization will take from you whatever you're willing to give. If you're willing to do the work, even the best managers who look out for you and understand burnout are probably going to take you up on that. You are the best guardian in setting your own boundaries.

Thinking time is really, really valuable. If you don't give yourself room for that, you're not going to be as good as you could be, despite what you may think.

I think back to when I had my children in 1999 and 2002, we didn't have the ability to do our work at home in the same way that we have now. Technology allows me to work anytime I want, which means I can have dinner with my family every night. But if you don't have boundaries and don’t set your own limits to when you're going to be on and off, you're going to burn out. Even physical boundaries are important. Find a place in the house where you do your work. Set the boundary mentally, and then when you leave that space you know that you're done with that work. Don't go on vacation and still check in. The ability to disconnect is incredibly important, and it sets the tone for the rest of your team. Having thinking time is really, really valuable and it brings better ideas to the company and ultimately makes you a better executor and more productive. If you don't give yourself room for that, you're not going to be as good as you could be, despite what you may think.

You've worked at incredible companies that are flagships in the industry. If you had to pinpoint your most significant accomplishment, what would you say?

I pride myself on having deep, authentic relationships with people. Not relationships where you get a note out of the blue when someone is looking for a job, but the relationships where you stay connected in a real way, mentoring and nurturing along the way. I love showing gratitude to people and saying thank you. I'm somebody who likes to send a thank you note for the smallest thing just to recognize that people are working really hard. I still write physical thank you notes in my personal life because no one does that anymore. But I think it matters in this generation, taking a minute to say thank you, being grateful and recognizing people.

You've been in this chief of staff role at a few companies. Do you aspire to be a CEO?

I don't aspire to be a CEO. I'm more introverted than you might think and I enjoy being behind the scenes, making it all work. My extroverted-ness shows up in my relationships with people, but I really don’t enjoy doing big public speaking events. The role you need to play as a CEO — to properly drive your brand, your presence and your voice — is not the most exciting work to me. The most exciting work for me is making “it” happen. Making the company hum along, getting it done, being able to bounce into the details when I need to, but also still able to be very strategic — I enjoy having that grasp on both.

The most exciting work to me is making “it” happen. Making the company hum along, getting it done.

Tell us about your current CEO Todd McKinnon. What do you love about working with him?

He is so smart, thoughtful, measured, and confident. Even when he tells you that he’s not sure what’s going to happen, you still trust that he has a plan and he'll figure it out. He exudes this confidence and he's comfortable in his skin. You should always seek to work for people who are comfortable in their own skin. I was actually thinking about the four CEOs that I've had the opportunity to work within my career; Steve Jobs, Scott McNealy, Marc Benioff and Todd McKinnon. Each of them built a company with a particular emphasis or lens and it really came through in how it shaped the culture of each organization.

You should always seek to work for people who are comfortable in their own skin.

Todd is a product-oriented thinker, he's an engineer. There's a depth and an authenticity about him that I think comes out in his leadership style and the way he approaches the decisions he makes for Okta. Given what we sell and what we do, I can't think of a better leadership style to drive this company forward.

How do you want your closest friends to describe your professional legacy?

I’d want them to say I was someone who invested in bringing up the next generation of leaders. Which is an investment. I do a lot of mentoring with young women in the organization rising up in their careers. I give my input and advice, but I get as much from them as they get from me. I think that's an important attitude — realizing that just because you may have more experience or know more about a certain thing, we're still all in this always-changing industry together. And it is always changing, especially now.