Developing your second in command

One of the most important tasks you will ever face as a manager in marketing (or manager of anything) is developing your second-in-command. With a strong second-in-command, you can do things like travel to speak at events, do advanced research and development, focus only on your top priorities for maximum productivity, or even go on vacation.

Without a strong second-in-command, you will forever be in the weeds, keeping the trains on the rails, and frustrated at your lack of personal professional growth. You’ll also never go on vacation for more than a day.


Here’s a simple test to determine whether your second-in-command is strong enough. Suppose you got a notice that you just won an all-expenses-paid two-week dream vacation to the place you’ve always wanted to go – but you have to leave tomorrow. Could you go? Is your marketing team structure set up well enough that your second-in-command could simply pick up and run with the ball for a couple of weeks? If the answer is no, then you need to invest in your second-in-command.

How do you invest in your second-in-command? Developing them requires both knowledge and practical application. Knowledge should come from training and writing down everything (or in this day and age, recording training videos). I do this for my team at SHIFT Communications; I’ve made an entire training library of step-by-step videos with screen casting software.

Practical application only comes from actually doing the work – and delegating every possible task to your second-in-command. This doesn’t have to be an immediate, all-or-nothing proposition. When Buddhist monks on Mt. Hiei prepare for some of their most grueling trials (such as 9 consecutive days without food, water, or sleep), they work up to the experience. When runners prepare for a marathon, they don’t knock out 26.2 miles on the first day. Preparing your second-in-command requires a similar mindset for preparation. Give them a little more every day. Let them run small programs and ladder up to bigger and bigger programs and campaigns.

Measure your progress by asking yourself the dream vacation question repeatedly. Check yourself to see how much closer you are to a “yes” every week, until you reach a point where you feel yes, your second-in-command could keep the trains running for a couple of weeks without you.

With luck, not only will your second-in-command be ready, you’ll also get that dream vacation.

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Is this the most difficult time to be in marketing?

Mark Schaefer recently posed the interesting question, “Is this the most difficult time to be in marketing?”

Maybe. To be certain, many of the factors Mark listed, such as overwhelming amounts of information and rapidly shifting change are valid and true. That said, what really makes marketing either difficult or not today is dependent on your personal answer to one key question:

How good a student are you?

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By student, I mean someone who studies the profession of marketing to learn and master its intricacies. A dedicated student is one who acquires and tests knowledge. One of my martial arts teachers and mentors, Ken Savage, has often said that to be a true student of anything, you must acquire academic knowledge and then put it to the test. When you take ivory tower theory and marry it with practical application, you create wisdom. The very best students can learn in a self-directed manner in addition to learning from great teachers.

The current state of content marketing lets us deceive ourselves that we are learning. But it’s learning in the same way that snacking isn’t the same as eating. We read dozens of status updates, pithy quotes, and short ‘stackable’ blog posts about the topic of marketing (“9 ways to blog about marketing!”) and feel as though we’ve learned something. The reality is that we’ve barely gotten the academic knowledge. Reading it is certainly not the same as applying it.

You have to be curious.

You have to try, and fail, frequently.

You have to get your hands dirty, often.

When you look at the skills Mark listed in his article, they all require actual learning, being a dedicated student of marketing. You won’t advance your capabilities from just reading a few blog posts on the topic or going to a conference for a couple days.

You have to be an actual student.

If you can be, and you can be a student for life (or at least the duration of your career in marketing), you will find that this isn’t the most difficult time to be in marketing. While the details and technologies change, while the landscape is ever shifting, your dedication to study will not only allow you to keep pace, but to eventually lead the pack.

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Should you self-publish or work with a publisher?

Self-publishing has undoubtedly made the book publishing process much more democratic. People can publish themselves or work with a publisher, and on the whole, that’s a good thing. We see this happening across so many media channels. YouTube democratized TV. Podcasting democratized talk radio. Blogging democratized op-eds; Twitter democratized news to the point where some mainstream media news shows are little more than someone reading tweets aloud. Self-publishing means more content – good or bad – is available, and it lets the free market work to determine who really is excellent.


The question many of us have faced, and that you might be facing, is whether to self-publish or try to work a book deal with a publisher. The answer, unsurprisingly, is that it depends on three factors: marketing, money, and quality.


Do you have your own marketing engine? By this I mean a large, responsive following in social media, a large email list (1,000 or more subscribers with high open rates and high clickthrough rates), experience with (and budget for) advertising systems, and/or access to people who can do this for you? If so, the primary purpose of a publisher – marketing and distribution – is already something you fulfill.

If you don’t have the network, a publisher will probably do a slightly better job of marketing your book than you will. In my case, my marketing capabilities exceed that of most publishers, so I chose the self-publishing route.


Do you want to publish a book as a loss-leader for a speaking career, or do you want to make money from it? For many authors, book deals are unprofitable, sometimes deeply so. Publishing a book as a loss-leader with a publisher means taking very small advances (since you have to pay them back through sales or cash out of pocket), and having the publisher leverage their distribution deals to get your book seen.

If you want to make the lion’s share of the cover price for every book sold, self-publish instead. Amazon lets you keep anywhere from 35-70% of the cover price; vendors like Gumroad (which I use for my books) let me keep 95% of the cover price.


Some publishers, depending on your deal, offer you the services (usually at your cost) of a copy editor and/or proofreader who can help you improve the quality of your book. If you go the self-publishing route, quality is entirely up to you. If you want a professional editor, you’ll have to find one on your own.

Despite the existence of works like 50 Shades of Grey, quality does still matter, especially with business books. Whichever route you choose, make your writing the best quality you can afford.

More Reading

If you’d like greater insights into choosing how you distribute your books, go check out the blog of my friend and martial arts mentor/senior Jon F. Merz. He writes frequently from the independent author perspective, and has lots of useful advice to offer from someone who makes a living writing independently.

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