On creating opportunities, combating imposter syndrome, and effective leadership with Angela Grady, Okta's chief of staffFeatured

I spoke with @AngelaGrady, executive vice president and chief of staff to the CEO at Okta, a publicly traded identity and access management company based in San Francisco. Prior to Okta, Angela was SVP of operations and chief of staff at Salesforce, director of services sales at Sun Microsystems, and a public relations account executive at NeXT (founded by Steve Jobs). Angela joined NeXT right out of university in 1989. Through her time there, she learned the importance of market opportunity and the power of effective marketing. She then went to Lighthouse Design where she ran marketing, which included writing foundational user manuals and formulating the full packaging and branding. Sun Microsystems acquired Lighthouse, so Angela moved to a marketing director role there. When leaders she had worked with left Sun Microsystems to go to Salesforce (at the time, just a burgeoning company), she did as well. When she started at Salesforce, they had fewer than 500 employees. In 2014, leaders she worked closely with at Salesforce transitioned to roles at Okta, and she moved as well, starting in a global operations SVP role and transitioning into the EVP and chief of staff role in 2018. Angela shared her advice for creating opportunities, prioritization, career growth, combating imposter syndrome, and effective leadership. Work with people who see more in you than you see in yourself. At Sun Microsystems, Angela built out the full analyst relations program, something that was initially entirely new to her, but her boss had tremendous faith in her ability to achieve, and she began to see this in herself as well. Through this increased confidence and supportive environment, Angela was able to build and grow an incredibly successful program. A key to combating imposter syndrome is to work with people who not only expect more from you but also truly believe more in you than you do in yourself. Over time, you begin to see yourself from their perspective and reimagine your capabilities and potential. Follow great leaders through companies. People and especially leaders are truly the most defining parts of a company. Throughout Angela’s career, from NeXT to Lighthouse to Sun Microsystems to Salesforce and to Okta, she has sought out open minded leaders who inspire her and built her own reputation and brand in this way. When considering the next opportunity, she focuses on finding and following great leaders who she respected and trusted. Go where there is market opportunity. Find companies with the most opportunities (different divisions, product lines, or growth areas within the business), especially early on when you may still be determining what functional and industry areas you enjoy and thrive in. Build cross-functional relationships within your company. Frequently, the most impactful projects involve cross-departmental work. Having trusted allies, friends, and even just some existing point of contact with other groups in the company can be tremendously helpful. Moreover, through understanding how different parts of the company work together, you can make better decisions by considering the full picture and context. Be authentic. Too often people speak in meetings simply for the sake of speaking to check a box or prove their title, which can easily come off as disingenuous and be detrimental to your brand and reputation in the organization. Instead, focus on and be driven by the work and company itself. Talk because you care not because you feel like you need to. Be less of a mentor and more of a peer. Mentorship can frequently have a connotation of authority, indicating the mentor knows best and is simply instructing the mentee. Angela instead sees the relationship as an open, equal level exchange. Instead of providing one directional sage advice to younger women, Angela spends time with them to exchange ideas and learnings in both directions. These relationships are also much more organic and open, which further helps the mentee because the conversations are built on deeper mutual understanding. Do not be afraid to hire people more capable than yourself. As people move from employee to leader, they often find it difficult to lose the “go, go, go” mentality. As a leader, however, you need to find a way to scale yourself through building a team around you. Find people more capable than yourself in key areas. Their performance will only reflect well on you and your ability to identify, retain, and cultivate great talent. Be open to inventing the process as you go. Even if you know the pitfalls ahead, you cannot always be perfect. Do not put too much pressure on yourself to create endless contingency plans. There are always unforeseeable challenges and complexities. You will inevitably be figuring out a lot in real time as you go along, but that does not limit the caliber of your production. Have a distinct, separate work space at home. During quarantine, Angela has designated a separate room in her home as her office. She spends the working hours of the day there but in the evening, she closes her computer and leaves the room, marking the unequivocal end of work, which has been tremendously helpful in creating work life balance. Respect your boundaries. Fundamentally, boundaries make you better. Angela actively encourages her team members to not be incredibly responsive during their vacations. She truly wants her employees to be able to make full use of their space because the best thinking often comes from a distance. You need to step away to be more effective as a team member and as a leader and truly, as a person to even simply avoid burnout. While some emails may seem urgent in the moment, looking back, almost anything can wait, and your physical and mental health and well being always come first.