5 Lessons in a 5 Year Career

Nearly 5 years ago, I was irresistibly drawn to Product Management like a cartoon character lifted by the nose to a windowsill by the aroma of a pie. I'm now a Technical Product Manager, something impossible to have predicted, much less imagined, when I stumbled out of college with my liberal arts degree, blissfully oblivious to the existence of Excel functions. But reflecting back on the challenges and lessons of the last 5 years, the shortest hurdles to jump were technical, much harder were the problems common to anyone new to a fast-paced, high-stress, cross-functional role. These are the lessons I learned, and continue to learn, hopefully some of which resonate with you.

1. Put other people first.

The compelling reason for putting others first is that pretty much any other motivation will make you miserable. If you base your career on personal ambition, on getting ahead, then there is always someone younger, more talented and ambitious to keep you from feeling successful. If your sole mission is to build great products, even at the expense of the people you work with, you're toiling on a sandcastle, and when those new-tech waves eventually reach landfall, rendering your product obsolete in the market, you will have little to show for it. Always start with people—users, clients, colleagues, family. Make them your mission. Striking the exact balance between them is hard, but at least you've already solved half your problems by focusing on the only thing that matters in the end—people.

Putting others' needs on par with your own is not easy. It's a daily struggle that gets easier with practice and harder without. But with time and practice you'll find—as part of the strange, inverse logic of the universe—that the more you genuinely care about others' opinions, interests and well-being, the better things tend to work out for everyone (including you). Treat people below you on the corporate totem pole with a little extra kindness and those above you with a little extra feistiness.

2. Define yourself.

One tension that simply must be embraced is that in making others your mission don't let anyone else define you. In Product Management, there are many stakeholders all with competing interests and an aspect of the role is to work across your stakeholders to strike a balance that delivers the highest net value. Once a decision has been reached (especially without consensus), it's important to be explicit on the reasons for the decisions, let people check your math, always be open to new objections, and never be afraid to reverse bad decisions. Yet invariably when the dust settles, some people are still unhappy.

Remember that every criticism—however clumsy and crass—is a potential opportunity for improvement. It's your obligation to consider it fairly and, if valid, do something about it. In Kipling's words: "Trust yourself when all men doubt you but make allowance for their doubting too." Stay humble. Make it easy to admit mistakes by defining yourself as life-long learner, rather than the expert in the room. Conversely, be generous with others' mistakes. Never attribute to malice or laziness what can be explained by sincerity lacking information. If you define yourself by working hard, thinking hard, wrestling with feedback, and putting people first, then there's no criticism you should fear.

3. Sharpen the saw.

It's the small daily disparate requests you need to watch out for because they'll sap all your time and brain-space if you let them. Devise rules of thumb for handling them. Is the request not worth anyone's time? Say no. Is it worth someone's time but not yours? Delegate. Is the request important and only you can do it? Batch them throughout the day. With your newfound freedom, budget time to learn new things that will make you a more valuable employee. "Sharpening the saw" is a vivid metaphor from Stephen Covey's 7 Habits of Highly Effective People, meaning you've got to keep your skill set sharp to keep growing. It's not only good for the company, it's good for you. And remember, you're your only advocate for growing your career.

Take inventory of your skills and knowledge. Decide whether you want to generalize or specialize. Identify skills you'd like to learn. Budget time to improve your skill set. Many companies have their own online training portals; if yours doesn't, explore professional certifications or online learning platforms like Udemy, Code Academy or Youtube. Go back to school. Subscribe to industry blogs. But remember: the key is consistency, so the biggest thing is to find encouraging, likeminded, growth-oriented people and surround yourself with them for motivation.

4. Plan. Don't react.

In the day-to-day work trenches, it's easy to get sucked into details and lose focus on the big picture. It's really easy to get into a reactive state and, in trying to kill the fly on the wheel, miss the looming iceberg. This is especially a risk if you're accountable for large, critical, complex deliverables like getting a product to market. If you have the luxury of setting your own calendar, then remember to regularly recuse yourself from the day-to-day trench work and ask: am I working on the most important thing I can be working on and is this the most effective way to accomplish?

You can plan at many levels. When planning for the day, ask what meetings I have, do I need to prep for any of them, what are 20% of things that contribute 80% of the value? When planning for an initiative, close your eyes and ask: What does the perfect outcome look like? Then reverse engineer it. Get as explicit as possible. Have a problem but can't put your finger on the root cause? Get out an ol' fashioned notepad. Write the problem at the top (e.g. "I can't focus"). Under it, write "Why? Because..." and answer your own question. Keep doing this till you can't answer anymore (e.g. "Why? Because I'm tired. Why? Because I went to bed late.." etc.) That's likely your root issue and not you can do something about it. Find what planning techniques work for you and be sure to turn them into outlines and templates so you can re-use them.

5. First drafts only.

As a recovering perfectionist, I used to think most things weren't worth doing if they weren't done perfectly. I now realize the opposite and inverse are true: most things done perfectly aren't worth doing and most things worth doing shouldn't be done perfectly. It took me a long time to realize this and break the habit, but once I did it made me much more effective.

When planning out work, deliberately ask how well it needs to be done and give yourself permission to answer honestly. If someone asks for something, say an executive summary, don't be afraid to ask whether they need Grade "A" work or if Grade "C" work do. You'll be surprised how often Grade "C" work suffices. I used to think I needed to provide fully formed, airtight responses to everything. In my new paradigm, I recognize that that's either impossible or else a waste of time. The only (or at least the most efficient) way to reach a sound result is through playing catch with ideas, the more tosses between you and another person the better. My new policy is to work complex problems and solutions out with other people first, ideally in person but email/messenger work too. So far, so good.

There you have it. Five lessons from a five-year career. Though if you'd ask me again tomorrow I'm not certain I'd have picked these five. Anyway, it's at least cathartic to translate thoughts to words. If this helped you clarify your thoughts, either in agreement or disagreement, then this will have been worth sharing.