How to Become a Digital Strategist

Now that I am “of a certain age”, I find myself meeting with more people seeking advice on becoming or advancing their careers as digital strategists.  It can be tricky to break into and to navigate as the area of strategy has always been ambiguous and the role of ‘digital strategist’ can mean very different things across different organizations.  Since I have had a few of these chats recently—which I thoroughly enjoy—I thought I would share some of the advice that I have found myself repeating.  Before I do, a few important caveats:

  • This is coming from the perspective of someone who has focused on marketing, working largely within digital agencies and consultancies.  They may not apply in other organizations.
  • These things have worked for me, and come from my own personal experience.  They may not work for you, and others have very different perspectives (which you should listen to).
  • These don’t come close to replacing larger and more important points about navigating your career like finding your own strengths, mentors, passion, and purpose.


Now that I have appropriately set, if not completely watered down your expectations, here are 5 pointers on starting out and getting ahead as a digital strategist.


1. Find a Place to Learn

The best things that happened to me early in my career was being part of a large, experienced, ambitious, and terrifically opinionated strategy team at a digital agency (you know who you are).  These strategists intimidated me, challenged me, and humbled me.  They also supported me, and helped me to understand what great digital strategy work is and how to get there.  It was a great place to start. 


So, look for a place in the smart room.  Avoid roles at organizations that are looking to hire a few, smart, young people as strategists to compensate for their lack of ‘digitalness’.  These may seem like attractive roles, but are usually terrible places to start a career in strategy.  You will not learn, grow, or understand how high the bar truly needs to be set.  Do not become The Digital Expert, and be suspicious of organizations that need one.


2. Start Narrow, Then Go Broad

At one point very early in my career I was the lone planner in a digital agency and I worked on everything that came in through the door.  At the time, I loved the challenge, the variety, and the chaos. Now, I know that it was a mistake. My work was incredibly uneven and I was put in positions where I could not succeed (though I did not recognize this at the time).  While perhaps not as exciting as a ride, I would have been far better served to find a situation where I could have started out by focusing on a sub-discipline of digital strategy (analytics, UX, research), and grow to become a more integrated, generalist strategist.  This only comes with experience.


Tim Brown is known for espousing the term T-Shaped people to describe the ideal candidate for working at IDEO.  The horizontal bar of the T represents the ability to collaborate across disciplines and the vertical bar represents depth of a particular expertise.  While digital strategy requires both, it is important to keep on strengthening that vertical bar, as it is your foundation.  So start by focusing on a specific area of expertise that interests you and that can lead to broader strategy work.  Don’t leave your development solely to your client work—add a course or certification every year, and broaden out over time.


3. Become a Great Facilitator

When I first moved from client side to agency side, I encountered an environment where everyone was competing for the ‘silver bullet’; that single insight, idea, or creative “aha” that quiets a room and announces your staggering brilliance.  I was game, and even garnered a few “aha’s”, but my approach completely changed after my first time with a truly great facilitator. He was the CCO, and he came in and completely reoriented the structure, values, and atmosphere of a work session by leading a process to collectively reach an idea.  He found a way to get to better thinking by empowering this broader group, and he got exactly what he needed.


The most interesting digital strategy work is messy, and requires a number of different disciplines working together to solve.  Reorient your focus as a strategist to be the one responsible for leading the development of the strategy, not the one individually creating it.  Adopt a highly inclusive approach that invites contributions that you can then synthesize and use.  It will not be comfortable at first, so invest in a facilitation training course and practice.  Learn how to keep responsibility while distributing access and ownership.  You will need it.


4. Ask The Right Questions

One of my all-time favourite clients was the CIO of a multi-national corporation based in the Netherlands.  We were in the middle of a kick-off meeting chock full of PowerPoints and Gantt charts when he stoically rose from his chair and announced that he had 3 ‘hamvraag’.  While this translates directly (and deliciously) from Dutch to English as ‘Ham-Questions’, it refers to a crucial question.  Holding up three fingers, he described what he considered to be the three questions that this digital strategy had to answer.  In answering them, we would then address every other item detailed meticulously in the decks and charts.  We did not pay much attention to this at the time, but once we started to put our recommendations together we realized that he was exactly right.


So before you start pulling data, thinking of solutions, or even opening a browser make sure that you stop and think of the right few questions you need to answer as part of your digital strategy.  If you are starting out, ask your client or manager to articulate them for you.  Focus all of your energy on answering these, to the exclusion of everything else.  Good clients and managers will recognize this and value it over a fat deck filled with graphs and screenshots. This also extends to the digital news and articles that you track and share socially.  Take the time to think about what it means, and the interesting questions that may arise for you to chew on.


5. Prove It, Then Sell It

“YOU are the one who needs to prove ROI!!!”  This line—a subject line, I believe—is from an email that I received from the CEO of an agency that I worked for after a particularly difficult presentation (specific names and colourful language omitted for brevity and taste).  In short, our recommendations were challenged and our case was weak.  It was a painful but important lesson to plan for the worst and always build a strong case.  As a digital strategist, it was also an important recognition of the value that I could bring to the table for an organization in proving and selling work.  I remember it to this day.


So the next time you are developing a digital strategy recommendation, think of the smartest person you know.  Now pretend they don’t like you or your ideas.  Next, picture them at the back of the room for your presentation.  You are their last meeting of the day before they start vacation.  And…you’re up!  Going forward, consider this your audience.  Take the time to prepare the case that illustrates the benefits from your recommendations.  Write out (and I mean literally write out) your rationale for why you would invest this money if you were in their shoes.  Get to know the supporting details and the data.  Believe me: the next time you run into this person along with your boss, they will invest in you.