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  • Writer's pictureNick Caldwell

Career Acceleration Starts With You


Giving back is a huge part of Reddit culture and one of my favorite parts of the job. A couple weeks ago I had the pleasure of hosting some bright college kids from the Gen-I Youth Network at Reddit HQ. They were very sharp minds and in all honesty I think I learned more from them than they did from me! During the Q&A a student asked:

“What advice would you give to someone who is just starting out and wants to get up the career ladder fast?”

I’ve been asked this question many times and had different answers at different points in my life. Now that I’m pretty high up the ladder, I tell people not to rush so much. Take your time, enjoy the ride! Looking back on my career, it has certainly been the journey and the people I met that mattered most. But, of course, smart ambitious kids don’t want the hear that answer! They want to know how to get promoted FAST!


So let’s talk about that. First, a little about me: I started my professional career at Microsoft and moved up the ladder there relatively quickly. I rose from entry level engineer to engineering manager in about 3 years, and became a partner level General Manager in about 12 years. (For those of you who don’t speak big-company: at Microsoft, a GM is responsible for the product management, engineering, and design teams in a product unit.) Now I’m VP of Engineering at Reddit, the country’s fourth most visited website (Yes, this is the best job ever).


Getting up to VP level in 15 years was difficult and is also one of my proudest accomplishments. If you’re a career climber, then I hope this blog post will help you with some practical inspiration for the early levels of the career game. Let’s go!


FIRST: Don’t wait for people to tell you what to do!

Most new employees assume that their manager is the source of truth in all things related to the company and their career — that somehow by simply following their instructions they will achieve upward momentum. Although this is generally a really good starting point, it is isn't the best approach. Doing only what your manager tells you to do limits your options to the set of things your manager a) knows about and b) wants you to work on. The trick to fast advancement is in aggressively expanding your available options.


But how? Story time.


I vividly remember my first day on the job. My manager was out on vacation and had totally forgotten about my arrival. By day two I’d run out of onboarding documents to read. And my manager was still out, probably laying on the beach somewhere. On day three I decided I’d had enough waiting around.


I scheduled meetings with my peers, all the line managers in the organization, the general manager, and the highest ranked team members I could find in the employee address book that would talk to me. If you’re ever new to an organization, make sure you do this early. There is a narrow window in which people will give you “new guy” meeting access and a free pass for dumb questions.


During each of these meetings I always asked, “what would you do if you had an extra person to help out?” I guarantee that if you ever need ideas to get ahead, at any point in your career, a 5-minute conversation with your peers or manager starting with this question will pay off because of how quickly it surfaces unmet needs. Ask it to yourself right now and you’ll come up three ideas in the next minute.


By the end of that first week I’d collected a list of requests longer than my arm: bug fixes, internal tools, cool project ideas, documentation tasks, etc. One guy named Kevin had an extremely good idea: “Rewrite the Word spell checker so that it works in more languages than English.” With Kevin’s encouragement and approval from my manager (of course!) I jumped at the opportunity.



If you ever see a red spellchecker squiggle in a Microsoft product, that’s probably me helping you out. The code I wrote ended up shipping in Word, PowerPoint, Excel, SharePoint, Exchange, and a bunch of other Microsoft apps. As a result, it’s used by a billion people around the world in more than 100 languages. Even better, the spellchecker provided me with a network and a personal brand. Anyone from around the company that wanted proofing tools in their app eventually found their way to my office.

Real talk: this project landed me about 3 promotions and it all started with that simple question. Now, I don’t want you to get the wrong idea — I’m skipping over all the late nights of coding, long meetings, cans of Mountain Dew, pouring through MSDN articles with broken sample code, scrambling to fix build breaks. Getting all those promos took years of effort and you will need to put the hours in no matter what. But my point is that I didn’t sit around waiting for the opportunity, I got out and found it myself.

Every day we are surrounded by endless opportunities to get ahead, if we’re only willing to stop, ask, and maybe learn something new.


SECOND: Don’t box yourself in. Ignore fear. Ignore labels. Ignore boundaries.

Despite the advice I just gave you, I didn’t just limit myself to asking teammates for ideas. With my mile-wide entrepreneurial streak, I tried hard to come up with my own ideas and pitched them to my managers. They were were surprisingly cool with having a line-level engineer who wanted to talk product strategy instead of just coding all day. About three years into my professional career I somehow got the brilliant idea that I could pitch ideas not just to my managers, but also to seasoned Microsoft executives. In retrospect, this was one of the most cringeworthy experiences of my life, but I’ll share it anyway.

I came up with an idea called the “Microsoft Content Marketplace.” Web 2.0 was the hot thing at the time so I pitched it as (and here is an exact quote) an “ajax-enabled web 2.0 site for connecting content creators with e-commerce content buyers across rich multi-media types.” (Ugh!!) Using that buzzword bingo elevator pitch, loads of persistence, and a demo hacked together in two weeks with a friend, I actually managed to get a meeting setup with four Microsoft Vice Presidents.

I remember the day of my very-first-ever executive meeting quite well. It was terrifying. I decided that perhaps by dressing up for the meeting I could somehow boost my confidence. So, I wore a blue double-breasted suit with shiny black patent leather shoes. I wore a tie with a little gold bar to hold it in place. I carried around neatly printed project plan notes in little binder, along with a stack of crisp, stapled copies for the meeting attendees. I looked much much worse than a used car salesman.

It was an hour-long meeting and I spent about 30 minutes of it just explaining what Web 2.0 was before I got to my product idea. Half of the execs left and the few that remained were clearly doing so out of politeness.

At the end of the meeting one of the VPs said, to my utter surprise, “Yep, it’s great idea, I’ll connect you with the right people.” Which I later learned was big company polite-talk for “never want to see you again, thanks!”

I met that same executive two weeks later coming out of an elevator and he told me more honestly, “Nick, that was one of the worst pitches I’ve seen at this company. It doesn’t match up with any of our executive priorities and there’s no alignment to any customer problems that I’m aware of. But in my 20 years working in tech I have never seen anyone your age with the guts to setup a meeting like that. I will remember you.

Fortunately, he meant that in a good way. A couple years later this exec gave me an opportunity to partner with his Microsoft Labs incubation team, and many years after that he gave me my first executive level interview. Didn’t get that job but he gave me shot.


THIRD: Career Speed = Skill x Effort x Luck

Many of my greatest opportunities came from being in the right place at the right time, knowing the right person, the office grapevine, or put another way: luck.

One last story.

About a 7 years into my career a guy named Kunal knocked on my door asking for help. Kunal was a friend and occasional collaborator who I’d met through a network of machine-learning enthusiasts at Microsoft. Of course, you should have guessed what he wanted: access to the source code for the spellchecker. No surprise there, but what was very interesting was exactly why he needed it.

Kunal, closed the door and in hushed voice, starts to tell me about a new project he’s involved in. He says it’s special: a collaboration between Microsoft Research and the product teams in SQL Server.

“So what?” I said, “Sounds like an experimental project that will never ship. What’s so special about it?”

Kunal turned his laptop to face me and open on the screen was an email sent from Bill Gates to a big chunk of his executive leadership team titled “Info Navigator.” The first few paragraphs were an outline for a radical new product idea. Bill wanted to create a tool that allowed everyday people to explore business data with natural language and interactive visualizations — a sort of Siri for data.


Info Nav prototype question and answer system hooked up to an Olympics data set.

As I slowly read the mail and fully understood its goals I determined two things. First, this project was basically impossible. The NLP technology required didn’t exist. The skills needed to build it were scattered across the entire company. The timeline proposed was hilarious. Even if you could pull it all together, the chances of building a user experience that people actually liked was slim to none. And on top of all that, senior executives from four different organizations were involved. It was an absolute 5-alarm fire in the making.


Second, and despite all that, I knew in my gut that I could get the project done. Some people run from a fire. Some run towards it. Some people are born in the flames. By the end of the week I’d setup a job interview for the Director role and taken my first step toward becoming a VP.


Why mention all this? Well it was a career-making opportunity that I only heard about because of a chance meeting with an acquaintance.


I believe that the speed of your career progression is the product of three things: skill, effort, and luck. Skill is the quality of work you are capable of naturally producing. Effort is the amount of time and energy you actually put into any task. Those parts of the equation are very straightforward: if you are talented or just work really hard then you’re off to a very good start. But the final piece of the equation, luck, is often the most neglected.


Create your own luck. You do it by proactively looking for opportunities, growing your network, creating a brand so that people bring opportunities to you, opening yourself to risk, and being unafraid of failure or embarrassment.


For most of us, there is no bypassing the grind — climbing the ladder takes effort. But the luck you create for yourself is the difference between an average career game and a speedrun.


rock on -nick

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