Always Answer

Job hunting is soul crushing. Everyone knows it. Even when it's by choice, it can still be a very humbling experience. Many folks looking for work have it much harder than I do, with much longer odds, and I'm thankful that I have the luxury of holding out for a position that I'm really passionate about.

Being on the market has made me think about a few things with much more frequency and clarity, and it's made me more sensitive to certain behaviors, especially my own.

When looking for a new job, whether its the next step on the ladder or a complete career shift, it will almost certainly involve talking to a lot of people. Not necessarily interviews or formal communication, just general conversations. You'll bump into people and do the  "What are you up to?"  dance. You'll tap your network for referrals or reach out to old friends to rekindle relationships in your new found free time. And yes, eventually you'll have Very Important Messages to send to people that may be able to offer you a job. And you know what? You're really, really going to want all of those people to answer when you call on them.

Answers don't have to be long, and they don't necessarily have to be what the person wants to hear, but I've resolved to always, always answer. A few promises to myself:

Next time a client or coworker reaches out with a question, I'm going answer it as quickly as possible. If I don't know the answer that's ok, but I'll be quick about saying so. Bonus points for pointing them in the direction of someone who can help.

Next time a long-lost friend reaches out to reconnect, I'm going to take them up on it. I may not know what will come of it, but I know what it will mean to them.

Next time someone needs a favor, I'll think twice before blowing it off. Just like in sales, "no" is still the second best answer you can get when asking for something. At least they'll know where I stand, and they don't have to waste any more time on a dead end.

Next time my mom calls, I'm seriously really going to pick up the phone. Seriously. On second thought, I'm just going to call my mom right now. You should too. I'm sure she'd love to hear from you, and I bet she'll answer.




A while back, I stumbled across Stewart Butterfield's Rules of Business on Medium. At the time we were having a lot of conversations about company vision and values at O3 World, and it got me thinking about my own personal guiding principles. Over the course of a weekend and a few bourbons I put my own manifesto on paper. Here's where I ended up.


Then ask again.

There's plenty of writing out there about the 5 Whys methodology. As members of a solutions-oriented teams, we're all biased towards action. We see a problem, we have an idea for a solution, and we execute. That's cool, but a couple of extra minutes of front to peel back the onion a bit can often lead to deeper insights and make sure time isn't wasted solving the wrong problem altogether. My favorite why is usually "Why is this even a problem in the first place?"


But always show your work.

I owe this one to the two founders of O3. One has a strong bias for going with his gut, making decisions on instinct and appreciating the same thing in the people who work for him. Fortunately, his instincts are often dead on. The other is a more quantitative guy, and though he has a good gut as well, the easiest and most effective to make your case to him is with numbers.

The tricky thing about this one is that you have to show your work a lot in the beginning, but once you've proven your intuition is sound, you can often skate by without the proof to back up your claims. You have to actively resist this for your most important decisions. Do your diligence. Even if it isn't required, be ready to show the work.


Pay attention.

I love data, numbers. They're easy to deal with. They organize well. If you look hard enough, you can probably find numbers that tell you what you want to hear. People are different.

When I was doing biz dev, we'd sometimes find ourselves in a situation where the person on the other side rejected our proposal because of the final number. Look a little harder though, dig a little deeper, and it often became clear that the real sticking point wasn't the number, it was something related to the person - how the project (or price) would make them look to their boss, what it meant for their department headcount, etc. The same is true when doing validation or user testing exercises. Scour your engagement and conversion numbers, but make sure you keep an eye on the people themselves, too. They'll tell you more than the numbers ever could alone, and you should act on that knowledge quickly. Tim Cook has his own take on this.


Including yourself.

Which leads us to number four. This one I adopted straight from Butterfield's piece because it struck such a chord with me. It also builds on the other points above. Showing your work? That makes it easier for other people to understand your decision making process, which makes it easier to either move forward or deliver a valid critique. Paying attention to people and not just numbers makes it easier to facilitate progress and equip your team with the tools they need. This is a good guideline no matter the size of the issue, from wide reaching business strategy to UX decisions to how long that email you're writing should be.

Justin Handler, a project manager I had the great fortune to work with for a few years, was incredibly good at this and really proved the value over and over again. Get an emailed question you have the answer to? Respond immediately. Trying to set up a meeting? Send specific dates and times, not open ended requests. Team struggling with a specific issue? Move mountains to remove blockers and open the way. Specific task hanging over your head? Make your own life easier and just fucking do it.


And do it as quickly as possible.

The best teacher I've ever had was fond of telling me "the road to hell is paved with good intentions" ... usually right after I finished explaining how I really wanted to turn my assignment in on time, but aliens had kidnapped my dog who had eaten my homework. He was right, if not entirely original. People will judge you by what you do. For them, for the company, for yourself. If you commit to something, do it. 

The corollary here is that when you say you're going to do something, there's almost never a reason not to do it as quickly as possible. No one ever got fired for exceeding expectations. If you for some reason you really, truly can't follow through? Own up to it as quickly as possible, and be honest about it. Silence is worse than failure.

This is the one I struggle with the most, since I default to wanting to make everyone happy and say yes to everything, whether I have the time (or desire) or not. Taking on more and not following through, or not following through fast enough, can be more damaging than just saying no in the first place.


Write pretty.

Because dammit, what's the point of doing anything at all if you aren't going to do it well?