I had a conversation recently, where someone asked me what stuff I read/follow/consume in order to stay sharp as a digital strategist. It was a fairly simple and innocuous question, that ended up sparking a weekend’s worth of thought and producing the 1,700 words or so that follow.
These are the things that I think make a good digital strategist, but if you have thoughts on this as well (it’s a subjective thing obviously), I’d love to hear from you in the comments or on Twitter.
Ignore the experts and industry publications.
A while ago, I stopped reading Mashable completely. I don’t visit the site, and I almost never click on Mashable links that I see in tweets. I only occasionally pop over to PSFK or The Next Web, but really infrequently if at all. And I don’t follow Chris Brogan, Brian Solis, CC Chapman, or other people who are widely considered to be social media experts. I’ve got nothing personal against these publications or these people (I’m sure they’re all talented, intelligent, and lovely), I just don’t feel like they add value for me.
So much of what happens within the little circle (and it’s truly little) of social media expert-dom, is tail chasing stuff. It’s tweet-bait headlines, bold and unfounded proclamations, and lots of recycled thinking. In the social media age, it’s all about the tweet-byte (it’s the new soundbyte), and rarely with the bother of thought to support the re-tweetable snippet.

For me, where I tend to find the most value (in terms of making me a better strategic thinker), is in going way outside of the industry chatter. Which brings me to my next item…
Expand your purview.
I’m fascinated by things like behavioral economics, the history of the banana or the credit card, physical computing, and the way people work best. Some of my favorite things to watch or listen to are Modern Marvels, This American Life, those “Inside” shows on CNBC, and the “How Stuff Works” podcast.
I love knowing things and I love knowing about things. And though these things aren’t necessarily a direct analogue to my day to day job, I find that this breadth of random knowledge and understanding of stuff, actually helps me to be a better strategist. Understanding how something works or how people behave, is far more interesting (and valuable) to me than answering “WILL GOOGLE PLUS KILL FACEBOOK??? OMG!!!”.
Be a Jack/Jane of many (applicable) trades.
Expanding your purview doesn’t specifically mean that you need to go out and familiarize yourself with every piece of trivia and minutiae on earth. And maybe you don’t care about all of that random junk I listed above. If that’s the case, it’s your duty as a good strategist, to at least become well-versed in what the other departments within your organization do, how they do it, and what makes them tick.
At one point in my life (actually, at several points in my life) I thought that my mish-mash of jobs and odd educational path was holding me back. I was sort of good at a bunch of things, but great at nothing in particular. I’d dropped out of more schools than most people generally apply to, and flirted with degrees in English, design, web development, and lots of other things.
As it turns out, that total lack of focus and commitment early on in my life, has served me better than almost anything else I’ve done. It’s allowed me to have a surface level understanding of sales, marketing, development, design, finance, operations, and almost everything in between. I may not be able to code an app from scratch or create a 30 second TV spot by myself, but I sure as hell know a good amount about what goes into making each of those things. And when I sit across from a developer or a creative in a meeting, I am able to speak the language enough, and able to understand their needs enough, to get their respect and to get things moved forward.
Have an opinion and be a skeptic.
I used to work with someone that we called “The Contrarian”. He loved to just give an opposing opinion, mainly for sport and for his own entertainment. Don’t be that guy or girl, but do be a skeptic when everyone else is running off of the cliff with reckless abandon.
As mentioned above, it’s very very easy to get sucked into the cycle of back-patting and tacit agreement in the social media strategy space. But, there’s huge value in at least considering the zig, when everyone else is zagging. Even if you end up ultimately going with the majority, asking the tough questions will almost always make an idea better, faster, and stronger.
Being the lone skeptic in a crowded meeting, can be a lonely and difficult position, but it’s a critical role that makes any strategic organization better.

I’m a fan of the “so what?” line of questioning. When developing a plan, or goals, or any part of a strategy, stop and ask “so what?” at each turn. You’ll be amazed at how it helps to form your ideas, and stress test your plan.
Be wary of statistics.
I once saw a presentation in which the speaker said something to the effect of “50% of users are actively doing X” in order to support his point that the client should do “X”. My first thought was, “What about the other 50%? Are they NOT doing X? How is this supporting your point?”.
We marketing types LOVE statistics. 72% of our time is spent trying to find any report or study, which has some snippet or stat (usually pulled totally out of context) that we can use to support the point that we’re trying to make, to sell in the idea that we’re already married to.
I love data, but I hate marketing statistics.

I’m not saying that statistics don’t have a place in strategy, because they most definitely do. I’m just saying (maybe hoping…wishing) that we strategy types were smarter and more honest about the stats that we chose to use to support our ideas.
Consider the source at least, and then think about what the data is really saying. Was that report on “The Power of Social Ads”, actually funded by, or put out by Facebook? If we take that little snippet and put it BACK into context, does the story we’re telling still hold up? Let’s not insult our clients with fluff that we don’t actually believe in.
Say “no” a lot.
Let sales people be the “Yes” men and women. A good strategist needs to know when and how to say “no”. Just because the newest whizbang social-digital-mobile-game-changing-omg-whoopdeedoo-app-site-etc just came out, doesn’t mean that we should suddenly shift all of our time, attention, and resources to being there.
Understand the client’s needs, their capabilities, their resources, and their appetite for adopting emerging technologies and platforms. THINK whether or not this change to, or addition to, the plan actually makes sense for them in the bigger picture.

Just because you can do something, doesn’t mean you should do something.
Use common sense.
Common sense is one of the most underrated skills that a strategist can have and use. It’s incredibly easy to over-think and over-analyze and over-complicate things. By nature, we strategy folks have a great desire to make things complex. There’s a feeling that if something is too simple, that it can’t possibly be smart strategy…and that’s a dangerous way to think.
Be sure and stop yourself often, and ask “does this make sense?”, or “would a user do this?”.
Learn how to build stuff.
One of the people in the digital/strategy/nerd space that I admire most, is Noah Brier. I’ve followed Noah for years now, and had a rather loose, digitally-based acquaintanceship with him, where communication has mainly happened via Twitter, email, and the occasional blog comment string.
Among the many things I admire about Noah, is his ability to build things as someone who doesn’t have a formal background in programming or development.
He’s built things like BrandTags and MyFirstTweet, and more recently, built an actual business called Percolate.
I can’t speak for Noah, but I’m guessing that his time tinkering and learning how to build things himself, has elevated his professional career in a pretty dramatic way.
Not unlike being a Jack or Jane of all trades, knowing how to build stuff gives you context and understanding, that allows you to be a better strategist.
I’ve spent hundreds and hundreds of hours over the years, learning how to build websites, fiddle with databases, understand the basics of APIs, and just pick at how things work. I’ve had scant formal training at best, and I can’t program much from scratch; but damn if I can’t find some basic scripts online, and try things out until I see how something functions.
Be a user, not just an evangelist.
I can’t tell you how many meetings I’ve been in over the years, where someone is selling in a program, based on some technology or platform that they themselves have never used. Strategists that are tone-deaf to user needs, and that only view platforms from the brand’s perspective, are destined to fail.
It may sounds painfully obvious, but don’t push a QR code program if you have a flip phone. Don’t talk to me about how Twitter is a game changer if you haven’t logged in for months. Please spare me your brand page “engagement” strategy, if you don’t follow brands on Facebook and have never yourself been a page admin.
You don’t need to love every technology that comes out, but you do need to be familiar with it. This space moves incredibly fast, and the best way to stay on top of where things are, is to be immersed in it personally.
What am I missing?
This is obviously just my personal opinion. What am I missing? What else makes for a great strategist? Comment away, or respond on Twitter. Would love to hear the thoughts of others.
