My Big Mistake

On my blog In The Tent I've been interviewing people that I've worked with over the years. The most recent interview was with my old Office 365 boss Dave Thompson. When I asked him for his best career advice Dave told me that he had asked Mike Maples the same question decades ago and Mike had said to him "Change is good."

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How can a guy that has been at Microsoft so long be writing about change? My career has had a lot of change, often to different projects where I knew the people. However, several years back I made a complete change: new team, new culture, and a new set of people. In that case, change didn't work well for me and I made some very big mistakes.

There were two things that went wrong.

First, I came in with a lot of my own ideas and passions and things I wanted to do differently. Although I took some time to learn the culture and context, I didn’t take enough time to let people get comfortable with me and to learn to trust me.

The second mistake was that I moved into an area I wasn't passionate about. I've done everything from backend systems to user experience, IoT devices to cloud services, applications to platforms, but the truth is that I prefer working on customer facing emerging areas. An internal platform or process won’t ever leverage my strongest skills, and this team was entirely focused on an internal platform and process.

The bigger failure was in the first mistake. I didn't mesh with the team; they didn’t mesh with me; and in the end they didn't want me around. I was isolated from the group, and I certainly felt it. I've come to believe that one of the worst human experiences is to feel this way. I was in a relatively empowered position, and it was horrible, so I can only imagine what it feels like when you are less empowered.

Sounds bad right? But in this case change was good! I made a bad mistake, my career took a hit, and I felt miserable…but I learned several important things and my empathy improved from the tough lesson.

These days I always advise people new to my team: “Take your time, go slow; you don't have to immediately 'show results' or 'have an impact'. Your job is simply to understand what is going on, get your feet wet, get comfortable, until you reach a point where you feel that you have sufficient context.” Equally important is that others need to see that you've taken this time to build context. This is especially true for people in leadership positions. If you take your time, later, when you have a suggestion, your team will be ready to listen to you. Not because you’re the boss but because they want to. Being patient in a culture like Microsoft's is hard as people often feel that they must show immediate results, but this can work against you.

I also say to new folks, "you deserve to be here." And I mean that. When you were hired, we made the decision that you were right for this job, and you don't have to prove anything to me or anyone else. You belong.

With time comes humility, and in my job, over time, you come to understand that you don't write one line of code, give detailed help to any customer, design or spec the guts of any feature. All of that happens through the work of the people on your team. I believe you have two main jobs as a leader. One is to create the "opportunity envelope." You help uncover the opportunity, get the funding, channel the concept, and create an open playing field for your team. The other is to set the culture. With a strong culture a team of strong engineers can accomplish anything. They can change course and/or deliver an entirely new service where nothing existed before. I've seen it terribly broken and working well and it always depends on the culture in the team.

In our team we run on two principles: ownership and approachability. I believe that empowerment comes from having a good degree of autonomy over your work. Giving people ownership drives satisfaction, empowerment, and trust. Of course, there are two sides of ownership - empowerment as an owner, and an "owner's mindset" where you care deeply about the outcome. 

The second principal, approachability, grew out of my tough career lesson. Approachability applies up and down the management chain between employees and their managers, but perhaps most important is approachability among team members themselves. As you look to your left and right are the people you see supporting you, and are you supporting them? My team expects this from each other and their management. This is perhaps the most critical element of our culture. It is also the direction Microsoft is headed.

The final lesson is that sometimes people deserve a second chance. I will be eternally thankful to Bob Davis, who I will add is one of the best business leaders I’ve experienced in my career, for recognizing my mistake for what it was and for giving me that second chance. Under Bob I came in to lead a new team, took my time, and built wonderful relationships with my team. Six months later we uncovered an unrecognized customer need and pivoted to build a new managed service from the ground up. I’m in a job that fully utilizes my skills, that I’m passionate about, and I work with a team that I love. I’ve never been happier.

The lessons don’t always come easily, and they can come at any time in your career. The important thing is to remember that there can be learning in everything, and sometimes the lowest points can bring the biggest insights.