Microsoft Marketing chief Chris Capossela on how to revamp career

1. Mistakes are not the end of the world

If you go on YouTube and search, ‘Bill Gates Crash’, the very first video will be me, onstage with Bill, plugging a scanner into a Windows 98 PC and the blue screen of death appears (the operating system crashes) with Bill standing right next to me, in front of 8,000 people. It was a big public blunder on my part but Bill was pretty graceful about it. He made a joke about it that the crowd loved and we kind of moved on.

I had failed in such a visible way, it was all over the media for the next couple of days and there were lots of jokes at my expense. Bill just focused on fixing the product and I remember him saying that I should think about what we would have done differently so that that didn’t happen again. Then he just moved on and never talked about it again. It was a nice example that you can fail spectacularly and still live to prove yourself the next day. I had embarrassed the company and him, yet he did not break a sweat, he did not yell – nothing. And that never happened again because I learned from it.

2. It is ok not to have a 10-year plan

I did not have a long term plan. I did not start at Microsoft and say that someday I want to be the Chief Marketing Officer. I think a lot of young people put a tremendous amount of pressure on themselves to think that they need to know what they will be doing in 10 years and then to make all the right steps between now and then. I had no idea what I wanted to be 10 years from then. Instead, I tried to find things I would be really excited to come to work and do every day. Even though lots of grownups were telling me, “You need a long-term plan”, I could not do it, and instead, I just kept looking for things that were exciting and inspiring.

I wish I could go back and tell myself that that is the only way you should do it, because I got nervous about not having that long-term plan, because doing something you love might lead to something new that you could never have planned. That is what happened in my career. One unusual thing led to another unusual thing. I have had jobs in sales, in marketing, in engineering and in operations. That is very unusual. You typically might stick with one thing. If I had taken their advice, maybe I would have stuck with only one thing and then missed out on all these crazy, fun and inspiring jobs that I got to do. So one piece of advice I give to new employees is that it is OK if you want to have a 10-year plan and it is OK if you don’t. If you want to have a 10-year plan, you have to be willing to re-visit the 10-year plan when something interesting pops up. 

3. Every little task will teach you something

Working on big things and working on really small, niche things are both really wonderful things to do. For example, I have had a chance to work on Microsoft Office, which is big and lots of people know it, and I have also had a chance to work on Microsoft Project, which is tiny and very few people know it.

A lot of times, people only want to work on the big, fancy thing but Project was one of my favourite jobs in my 28 years at Microsoft, even if it was not fancy. If you went to a party with a bunch of Microsoft people and they said, “Hey, what do you do?” And you say, “I work on Project,” they would probably think, “Ok, I don’t know what to say to you now,” but if you say you work on Xbox, they would go, “Wow! Let’s talk!”

And yet, the Project job is just amazing. I learned so much. I think working on the big, fancy stuff has its benefits but sometimes you can learn even more from working on the small, quiet stuff, even if it does not appear to be glamourous. When I thought about taking the Project job a lot of people asked me “Why would you ever take that job?” I’m really glad I didn’t listen to them because I don’t know if I would have gotten this ‘glamorous’ job as CMO if I didn’t learn all the things I learned on Project.

4. To be a leader, be curious how things work

I did not pay a lot of attention to promotion velocity. I made a lot of lateral moves. For example, when I moved from sales to marketing, I had to start over. I wasn’t getting a promotion. I was willing to sort of take steps backwards because the job seemed really interesting. In that sense people were not really betting on me since I was really junior and I was cheap. I spent a lot of time working around the base of the company, and then every now and then someone would be willing to make a huge bet on me.

Then I would get a huge jump, then spend time working around that base again, then years later someone else would bet on me. So my promotions to Chief Marketing Officer didn’t happen in this gentle line that start from the bottom left and goes gently up to the upper right. They were these weird stairs and then a long, flat line and then a big stair step and then a long, flat line. I think in high tech, hiring managers are willing to make some gambles, so a couple of people along the way were willing to make a big gamble on me.

I think it is in part because I did all these crazy jobs that gave me weird experiences that nobody else really had. So I could convince them that my weird experiences were interesting, as opposed to somebody who had spent their whole career doing one discipline. I used it almost as a selling point – that I had spent a lot of time in the field, a lot of time in engineering and so forth. That worked out well for me.

5. Use this interview hack

I have gotten a lot better at telling a hiring manager why they should hire me or not.  That eases the pain because I don’t go through a long interview process. I will say, “Hey if you want somebody who has done this for 10 years, I’m not your person, but if you want somebody who has done these other things and maybe no one else you are talking to has done them, then I am an interesting candidate.” So I have short-circuited my interview loops by being very upfront with the first interviewer.

For example, when I interviewed for Microsoft Project, I had never worked for Project, so I said, “If you want somebody who has been working for Project for 10 years, clearly I’m not it, but if you want somebody who has done messaging for Bill Gates, who has worked in our subsidiaries, been to 38 of our subsidiaries in Europe, the Middle East and Africa), seen our customers and engineering team at it together, then I am your person.

When you do it that way, it makes the person who is hiring think, “What do I actually want? I thought I wanted someone with 10 years’ experience in Project, but maybe I actually want this crazy person who has done this. That’s kind of interesting!” Often, that will cause them to rethink what they want for the job, and I have gotten a few jobs that way, because I have essentially redefined it by knowing what I bring to the job and being clear about what I don’t bring to the job. It also saves me a lot of angst and anxiety because if I am getting a no, I get it in that interview.

6.  Make peace with rejection

If you saw all the jobs I got rejected for, my resume would look very different. It’s one thing to look on LinkedIn and see all these jobs I have had. It looks perfect. But LinkedIn needs a feature for “I interviewed for this job and I got rejected shamelessly. Ruthlessly.” You would see lots and lots of rejections throughout my career.

So you have to be willing to try and to fail. The rejection was terrible. I got better and better at handling it, but at first it really hurts. You feel like because you’re not good for this job, maybe you won’t be good for any job. And of course that’s crazy, but those are the mind tricks that the imposter syndrome plays on you.

You think, “When are they going to figure out that they never should have let me in through the doors of Microsoft in the first place? Well it seems that they are figuring it out because now I have gotten three rejections in a row.” Those types of things can really weigh on you. Ultimately, I have just made peace with the fact that at some point, the company is going to say, “That’s it. We’re done with you. It’s been great, but it’s time for somebody else to do this job,” whatever the job will be.

That is the reality for every human being on the face of the planet. When I realise it is not so much about me, then I feel brave to come to work each day and do the bravest thing I can do that day. Because if it is going to end at some point anyway, then I might as well take matters into my own hands and try to do my very best work, because then at least it is me putting myself out there as opposed to some other set of circumstances causing my boss to want someone else to do my job.