In a Tech-Infused Future, People Matter More Than Ever

David Oskandy, General Counsel and Secretary at Avanade Inc., sits down for a discussion on leadership style, with a little life advice mixed in for good measure.

CCBJ: What led you to your role at Avanade?

David Oskandy: A buyout of my former company gave me the opportunity to consider returning to the technology sector, which intrigued me. The industry is so dynamic, so fast-paced and filled with many bright people who are constantly innovating. Some former colleagues reached out and asked if I’d be interested in the general counsel position with Avanade. Their business leadership team was appreciative of my history of transforming legal teams at other companies I’d worked for. Given my affection for the technology industry – and the fact that Avanade is the most successful joint venture in tech with great partners like Microsoft & Accenture, not to mention the leading digital innovator on the Microsoft ecosystem – it appeared to be a natural fit.

Tell us about your leadership style and what influenced it.

It’s important to inspire a team and never lose sight of that. The team needs to understand where you’re going, why you are doing it and what the value proposition is. That’s not only for the team as a whole and Avanade but also for individuals on my team. I always try to lead by example and give very clear guidance on any initiative I put in someone’s hands. I always try to keep employee experience in mind. At Avanade we try to make our people feel inspired, confident and cared for. That means listening to my team and drawing as much as possible from them, including the different sets of skills of each member and their ideas. The more diverse the team is, the better it is – the melding of different perspectives, life experiences, strengths and weaknesses brings out the best in everyone and makes for the strongest possible performance. You need to build consensus for big decisions, so that people feel included and that their opinion matters. You need to encourage an open atmosphere where people feel comfortable speaking up and offering a different take on things. I make decisions with the team. I never ask anything of anyone that I’m not willing to do myself. I encourage the people on my team to see themselves as leaders, which includes not being afraid to make big or tough decisions and, of course, always being thoughtful about them.

What qualities do you look for when hiring new people for your legal team?

Intellectual curiosity and flexibility. People who really enjoy learning and growing, both intellectually and in their careers. The word “ambitious” captures it in a large sense. Not ambitious for position or power, but ambitious to grow and become the best lawyer and business person they can be. I’m hiring someone not only for a specific position but also with an eye on the next one, and the next one after that. It requires candidates with a certain level of intellectual agility.

I also look for people who enjoy working with other people and understand the importance of communication, because even though we are a technology consulting company, we are very much in the people business.

Whats the best career advice youve received?

Be courageous in building the career that you want. Don’t try to follow somebody else’s format. Build the career that you want, in a way that’s going to fulfill your interests and satisfy your curiosities. Also, get as broad a set of experiences as possible, as early in your career as possible. As a general counsel, you need to know about everything that’s happening at a company, from law to business, to ethics and public policy, to employee experience. Your finger has to be on the pulse. To build that up, you really need to go out and get those experiences, to make yourself that fully formed person who can understand everything that’s going on and do every job that’s required.

The other really important thing is communication. These days, to be a good in-house counsel, you’ve got to be able to communicate in a variety of ways, especially now that most people communicate via text and other technological channels. The communications are shorter, more to the point and frankly less personal. You have to adapt to that in order to capture people’s attention and convey the information in a way that fits the rhythm of their lives.

How about the best life advice?

Live generously. Think of others before you think of yourself, and share your own gifts and talents prolifically. I have tried to live my life that way, and I certainly was raised that way, and it brings me joy. I think the greatest joy I get in life is through sharing and living as unselfishly as possible. The return you get is enormous, in terms of spirit and what you learn from others.

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