How to transform your career by transforming a large company
I am one of many startup people to be acquired by a large company. One Wednesday morning in December 2009, I awoke to an announcement about an “exciting company-wide all-hands announcement!” Strange timing, Wednesday morning, but okay. I joined by phone, a field consultant stationed far from Austin headquarters. Listening in, we were told the company had entered into an agreement to be acquired by IBM.
Three score and thirteen companies ago…
IBM? What? The moment was surreal. The ups and downs came minute by minute, with text messages flying every direction while the call was still happening. Didn’t we make money by running circles around big, slow companies like them? Then again, all our stock and options cash out immediately, woohoo! But wait, don’t they already have a product like ours — maybe 4 or 5 products like ours? And what will we be working toward at this giant, faceless mega-corporation? But they probably have great benefits! Or, wait, do big companies still have big benefits? And don’t large companies pay poorly?
Since that day, an additional 73 companies have had the same pleasure of being acquired by IBM (if I didn’t lose count while checking the Wikipedia page).
Some acquirees departed almost immediately. Many coworkers departed during the first year or two. Some saw themselves as “startup people” and wouldn’t have it any other way. Others just saw it as good timing to try something different. On a slightly amusing note, a few colleagues had been acquired by IBM two or three times before and had seen their fill. It turns out post-acquisition departures are quite common. But are there opportunities people are missing?
Big company, big problems, big rewards.
I figured I wouldn’t stick around, but I had been caught offguard by the announcement and didn’t have any passive job searches teed up in the background. My client consulting work was going really well, and I had time to deliberate my next career move. I had shifted from product development into consulting, and it had been a great change at the time. But in my honest moments, I had to admit that I was now bored. I was competent, impactful, and valued — but bored doing it.
I collected a nice stock payout. That felt especially good because I had failed to negotiate for a written offer of stock options at my previous startup; so I hadn’t seen a dime when they were acquired. This time, I had been a part of a startup that won, and I had gotten a tiny piece. I wasn’t an early-stage entrant, so I wasn’t going to be starting my own VC fund, or retiring early, or buying a house with cash. But it was a sizable check nonetheless. And I figured I wouldn’t see another one like that for a while.
But in the wake of all the acquisition-related departures, it wasn’t long before I saw a retention bonus larger than my original stock payout. This surprised me, and it opened my mind to maybe sticking around a bit longer. It was as though they were trying to say: We brought you in because we know we need to make some changes, so help us make them.
It turns out large companies can pay really well, but you need to follow a simple formula: (1) add value, and (2) make sure your management team understands the value you add. Many people struggle to add value at large companies. But that is opportunity #1 at a large company. Think like an owner, find and address needs, and you can benefit enormously.
Trust can be exchanged for opportunity.
I had always been vocal with product management. Prior to consulting, I had led a product team at a software startup. So I knew the value of good feedback, and I was unabashed about giving it. I often expressed opinions about product direction. Not long after the acquisition, several good product people departed. I was invited to join the product team as a user experience designer. It sounded like a fun way to try out a new career, and if it didn’t work — well, I was planning to leave anyway, so nothing lost. I had planned to leave for another startup, but my new manager told me, “Why be a big fish in a small pond when you can be a big fish in a big ocean?”
I knew I would be unlikely to convince an outside company to hire me into a job for which I had no formal training. But in this case, I had built enough trust with an adjacent team that they were willing, even eager, to take a risk on me. And that is opportunity #2 at a large company: Connect with people in adjacent roles, and prove you’re capable; then they will take risks and give you opportunities that you would not get elsewhere. And you can meet a lot of people at a large company, so there are plenty of at-bats.
Going back to the beginning can be fun.
When I was in sixth grade, my teacher, Larry Beatty, would run a game every Friday afternoon called Social Studies War. He divided all the desks into letter-graded rows: the A row, the B row, C, D, and yes, the F row. He would pose questions on social studies topics, proceeding sequentially down the rows of desks until someone could answer correctly. Then, that person would grab their stuff and move up, passing everyone who had given a wrong answer, and settle into their new desk where the question had begun, sometimes moving up a letter grade or two. The game would continue until class let out on Friday afternoon, and whichever row you were in, row A through F, you were stuck there for a full week until the next game. I have no idea if this teaching method is politically correct, but it certainly awakened our competitive spirits.
The A row was hyper-competitive, and that’s where I often sat. But there was a stretch where I had been in the A-1 desk for several weeks. Quite frankly, I was just getting bored of it. I had nothing to gain, but quite a bit to lose. So I needed to know my stuff, but there was no joy in the hunt, no goal into which I could channel ambition.
I languished like this for weeks, until one day, I blurted out to the teacher, “Hey, I’ll give up my A-1 desk and go to the very last seat in the F row, if you make her (the girl in the A-2 desk) go back to the second-to-last seat in the F row.” Mr. Beatty immediately and enthusiastically agreed.
The poor girl. I hadn’t really thought it through carefully. It seemed like a fun way to give us something to shoot for. She spent the rest of the afternoon with her head down, crying softly into her desk. Even as a 12-year old boy, I felt bad for her. I think by the end of that day’s Social Studies War, I had bounced back to the C or B row. My co-victim kept her head down and wouldn’t answer any questions, and she ended the day right there in the F row, second-to-last seat. Thankfully, she recovered nicely the following week. We both eventually made it back to the A row, and in the end, it was so much more fun to work toward the top than to be at the top.
I’ve often thought of that experience in reference to my career. When you are at the top of a certain game, there often aren’t many ways to go up. The thrill of ambition is starved by decreasing upward mobility. So is that it? The end game of a career is to battle for a few privileged seats at the top? Or risk everything on your own startup?
Is there a way to revisit those exciting early days when learning is intense and rapid and the joy of growth is frequent?
Yes.
Formal education is always available. Small companies are often willing to let you “wear multiple hats.” And large companies can be the most fertile opportunity of all. You just have to resist the career linearity that entraps so many large company dwellers in a prison of boredom. Seek exponential growth. A career change isn’t always necessary, but if boredom ails you, don’t be afraid to go back to the F row.
“Life has a lot of chapters.”
John W. Gardner, a former cabinet member, professor, and author of Self-Renewal, said in a great speech on personal renewal:
“We have to face the fact that most men and women out there in the world of work are more stale than they know, more bored than they would care to admit. Boredom is the secret ailment of large-scale organizations.
“… you’ll begin to wonder what it all added up to; you’ll begin to look for the figure in the carpet of your life. I have some simple advice for you when you begin that process. Don’t be too hard on yourself. Look ahead. Someone said that “Life is the art of drawing without an eraser.” And above all don’t imagine that the story is over. Life has a lot of chapters.
“I said in my book, “Self-Renewal,” that we build our own prisons and serve as our own jail-keepers. I no longer completely agree with that. I still think we’re our own jailkeepers, but I’ve concluded that our parents and the society at large have a hand in building our prisons. They create roles for us — and self images — that hold us captive for a long time.”
They create roles for us that hold us captive for a long time: nowhere is that more true than in a career. But you are not your role. You are so much more. You do not have to be defined as a narrow set of skills, increasingly specialized. I do not believe this. We do not have to accept this. You can try something different, and there are people around you who would give you that chance, if they trust that you know how to grow.
Let’s return to my career change.
Pain is how you know you’re about to grow.
When I left the A row of my consulting role, and joined the F row of the product design team, I was initiated with a two-week design bootcamp. On a Monday, I was given a high-level problem statement, assigned a mentor, given a quick tutorial on Adobe Illustrator, then put to work. I was to conduct a “playback” — company code for a design presentation — in a couple days. I set to work, good-naturedly buzzing about in Illustrator, drawing layouts and filling artboards. It reminded me of my high school days doing newspaper layouts in Aldus Pagemaker, and it was kind of fun.
The first playback day came on Wednesday. I started showing my mishmash of wireframes and talking about how awesome it was all going to be. A few minutes in, a product manager interrupted me: “What are you even talking about?” He proceeded to scold me for jumping into the solution without introducing the problem, not giving sufficient background, not fully introducing what we were looking at.
It was a hard moment. And an amazing moment, because of what happened next.
Intellectual humility is the fastest path to mastery.
I bit my lip and listened to the feedback with intellectual humility. I was a very capable person, with enormous proficiency — at other things. I knew I was not the expert at this. So I listened carefully and stenographed notes with the energy of an intern. To achieve mastery, I would need to first be the student.
The product managers and designers probably left my first playback with deflated hope. Maybe they had made a mistake risking their hiring power on me. But I saw a silver lining: If I could learn from it, and improve rapidly, then I would easily exceed their expectations later. That awakened the “thrill of the hunt” that comes with learning and growth.
Stepping back from Illustrator, I sketched furiously on paper. I wrote out problem statements, auditioned different storylines, and sketched out ideas. I did research and ran ideas past my mentor. I arranged and rearranged. And finally, belatedly, I started back in Illustrator.
The second playback came that Friday, at the end of the first week, halfway through the bootcamp. I was a little sheepish because most of what I was about to show was in sketch form. I had scanned everything into a PDF, and I ran the playback by going through the PDF of my scratchings.
And it went smashingly. “Great setup!” “Good problem description!” “Coherent storyline!” “Definitely see how this could help out the target persona!” They were less-than-awed by the quality of the artifacts but left this second playback with renewed hope that I was not a total waste of money.
I had learned my first lesson in user experience design: users, goals, problems, and storyline first. In short, a coherent design starts with coherent content. (I had many more lessons to learn.)
Illustrator was my best friend and worst enemy over the following week, as I worked to polish the design. The end of the two-week bootcamp came, and I did my final playback to a full room of product leaders and executives.
“See, I told you he can do design!”
“That was good. That was really, really good.”
“We need to put this into the product!”
To my surprise, product management decided they liked the concept design so well that they were going to carve out an engineering team in the current in-progress release, and I was going to productize it. I was elated, and I set to work iterating with an engineering team. We had only a couple months, but I was able to help them make tradeoffs due to my engineering background.
But, casting a shadow over an exciting couple months, the product managers and designers who had already taught me so much, one-by-one began to resign. A product manager, a designer, another product manager, another designer — leaving to pursue other opportunities.
I was sad. I had hoped to learn so much more from these people. Change had come way too soon. But with change came opportunity.
Big company, big opportunity.
Three months in, I was asked to take on the role of product design lead. I had shown a lot of promise, I guess. Surely this was too soon. I didn’t feel ready, but I was the best available choice, and so my manager was willing to take the risk on me.
I had no time to wallow in self-pity. There was a major release to get out the door, and I was in charge of rallying the design team and working out the detailed designs for a huge engineering team to build.
I worked closely with key customers and business partners to gather user needs and feedback, and evaluate preliminary designs. This came naturally to me, since I had spent a lot of time with clients in my past consulting role.
The big reveal.
I knew there was a giant conference coming up the following spring. So I began to talk with my new product manager counterparts and plant an idea: what if we could get onstage and really blow people away with some amazing stuff? Great idea, everyone said. But what would be innovative? Designers love these types of questions.
I crafted a set of problem statements and goals, a storyline, and a set of design sketches. It started ugly, just like I had in my design bootcamp.
I gathered feedback, then refined the fidelity. The story inspired the product management team, and they carved out space in the release to make it happen.
The engineering team was inspired and wanted to find a way to make it happen, which was key because it was not going to be a layup. We worked closely to figure out how to put it all together, cutting some features but delivering all the essential ones. We landed the capabilities we needed and got on stage.
As a former consultant with a deep engineering background, I personally helped put the finishing touches on the live demo seen by 10,000 people, which showed two users collaborating in real time to get their work done, using forms built in a drag-and-drop form designer that was now newly extensible.
The product is the reward.
Glowing analyst reviews specifically called out my design work:
More impressive to me is the new task UI (“Coach”) designer, which features reusable composite controls that dramatically simplify authoring of complex task user interfaces without so much javascript and css code. For example, a data entry and a graph control can both point to the same data and communicate with each other automatically without scripting. IBM has also carried forward real-time collaborative editing from Blueworks Live into the Coach designer. Very cool.
The live demo was a success. But I had also worked tirelessly throughout the release with customers and the internal team to insure it would serve real users. Buzz was palpable at conference sessions. Customers crowded feedback sessions to ask for details. People tried it in hands-on labs. Customers responded with large new signings.
The business partners I had worked with launched new UI library extensions, creating a virtuous cycle of user experience improvements.
And IBM Design was funded shortly afterward. My design work had seen the light in a big way, and millions of dollars were about to flow into what would become possibly the largest-ever corporate expansion in user experience design.
If you want to grow, test-drive a second career.
To be clear, at this point I still had way more to learn about user experience design. I will share those lessons later. The key lesson for now is that you can explore your multipotentiality with a career change, and a large company can be a great place to do it. You just need to earn enough credibility that someone will take a risk on you. Then, if you approach it with intellectual humility, you can grow quickly and have a lot of fun achieving new things.
Should someone else have gotten these opportunities instead of me? Yes, probably. Others were certainly more qualified. But I was there, and I was open to being a beginner again. I was willing to set my ego aside and learn and work hard. I ran an A/B test on a new career, and career B worked out better than I expected.
Today there are software engineers who hear me speak as a user experience designer and assume I couldn’t possibly know anything about software engineering. Other times I speak to designers who hear me talking like an engineer, and assume I must not be much of a designer. Of course they are both wrong.
It is immensely rewarding to seek depth and mastery in multiple aspects of life. It is wrong to assume a person can only master one thing. That is only true statistically, and then only because most people believe it and self-fulfill it. Even when you master two career paths, there are people who dismiss it as an impossibility simply because they can’t conceive of it. Don’t let someone else’s limited thinking imprison your career and life satisfaction.
Transform a company, transform yourself.
Six years after my design bootcamp, I’m still at IBM. Why? Because there has been no shortage of opportunities to make an enormous impact. Still, I’m under no illusion that big companies are all sunshine and lollipops. I lead design for a large, complex and sprawling organization that is coming from behind. Transformation is not always as glamorous as it sounds. In the fog of war that comes with it, people can sometimes mistake you for the problem rather than the solution! Many of my workdays are excruciating. But some of my workdays are exhilarating — the summit view that rewards the climb. Transformation needs open-minded people who are willing to take a leap into the unknown.
Don’t underestimate the opportunities for growth a large company can bring to your career. The bigger the problems, the bigger the opportunities for success. And if you find yourself embroiled in a transformation, ponder this lighthearted analogy: Aligning a large company is like aiming the death star. It can take a while to get lined up, but then you destroy an entire planet! (If that offends you, pretend you’re firing a Hug Star that encircles planets in a warm fuzzy energy hug.)
Career expansion comes when you connect with people, show them your value, and develop enough trust for a decision maker to take a risk on you. Once given that opportunity, you can grow faster than anyone else by seeking critique and taking it with intellectual humility. You will do great, and even if you have setbacks, you’ll feel more alive than ever.
How will you know when it’s time to go back to that last seat in the F row? When the growth slows down.
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