What would you do?

Screenshot 2015-12-17 16.33.34
Photo credit: M. Kamran Meyer

I received a heartfelt request for help in my inbox this week. The writer has switched from a scientific field into account planning/strategy in the newer digital department of a well-known agency. He’s been in the role less than half a year.

Sadly, as you well said at the beginning of your book, employee development plans are non-existent. I was promised mentorship and that’s not really happening. It’s very frustrating because I made a big change and I just want to learn, not play around.

He goes on to ask what would I do if I were in his shoes and what kind of training he might look into to improve his skills in lateral thinking, strategic thinking, presenting, and creative writing.

What would you advise? Please add to the conversation in the comments below. This person will be reading and deeply grateful for our help.

So here goes, writer-friend; since you asked, here’s my advice:

From my perspective, while painful, I do think it’s best to stay in the role for one year. Our business moves fast and it is often surprising how quickly time flies when we are constantly under deadline. Your supervisor probably feels like you just started a few weeks ago.

Plus, I can say from my experience that this strategy stuff takes a load of time to get the hang of. I was more miserable than not when I started. And then slowly it began to suck less and less. Or suck in new ways so at least it was novel. Here’s a pertinent quote from Elizabeth Gilbert’s book Big Magic (page 150):

I recently read a fabulous blog by a writer named Mark Manson, who said the secret to finding your purpose in life is to answer this question in total honesty: “What’s your favorite flavor of shit sandwich?”

What Manson means is that every single pursuit–no matter how wonderful and exciting and glamorous it may initially seem–comes with it’s own brand of shit sandwich, it’s own lousy side effects. As Manson writes with profound wisdom: “Everything sucks, some of the time.” You just have to decide what sort of suckle you’re willing to deal with. So the question is not so much “What are you passionate about?” The question is: “What are you passionate enough about that you can endure the most disagreeable aspects of the work?”

Now, while you chew the shit sandwich on your plate at the moment, I do think an honest conversation with your supervisor is in order. Instead of complaining that what was promised has not materialized, start the conversation with an honest assessment of anything you think you have learned so far coupled with your sense of where you need to improve. Use the session to map the priorities of your clients and the agency. What one skill should you focus on next? When you can both agree to one skill, it will make it easier for your supervisor to keep it in mind when development opportunities (new projects on clients you are not working on, friends of the supervisor who might be able to teach you a case study, great video talk online, etc.) present themselves.

And on your side, with this laser focus, you can pursue people, books, talks, and conferences in your limited free time so that you will show demonstrable progress. When we pursue too many areas of development we gather scraps here and there that don’t add up to much. Have a look at this video of Josh Kaufman where he posits that we need to put in just 20 hours to bust through the frustration barrier of incompetence in learning anything. A lot less daunting than the whole 10,000 hours thing.

While I do recommend sticking it out for at least a year, I also believe we shouldn’t invest any more than a year making no progress. If you have the conversation with your boss, get aligned on your learning priority, make the extra time to pursue it, show demonstrable progress and then don’t get any additional interest shown or mentorship extended in your direction? Time to move on.

Now, on your specific requests, just keep in mind I am not recommending trying to tackle all this at once. That’s the boil the ocean strategy to learning, as the cliché goes. I’m an advocate of the elephant eating strategy, as in: How do you eat an elephant? One bite at a time. Here are some resources I would look into divided by skill.

Lateral thinking – This one is my favorite because ANYTHING you do that is not your daily grind will help. Have a read of Steven Johnson’s Where Good Ideas Come From as a primer for creativity then follow your curiosities wherever they take you: scroll through meetup.com and pick something you wouldn’t normally attend, take up a personal project like creating a podcast on a subject you want to know more about, sign up for the next class you hear about, no matter the topic. Be open to serendipity as well, even if you’re not that interested in a topic, but someone else wants you to explore it, like I was when my husband insisted I learn how to play video games.

Strategic thinking – This one is harder because I believe it comes from the hard slog of working through problems over and over. Studying ways of working, as in reading books, can help. My favorites include: Good Strategy Bad Strategy, Cultural Strategy, The Lords of Strategy, and Clay Christensen’s Jobs to be Done methodology. One less sloggy top tip: Attend a session of House of Genius. All types of people from the community come together to advise start-ups in an anonymous salon format. You will witness first-hand how a diverse group of people see a business challenge differently as well as having the opportunity to offer your advice to a fledgling business. And at the end when you learn who everyone is and what they do, you’ll want to meet each other based on the caliber of your ideas, not what’s on your business card. The number of people who want to talk to you is an instant metric of your strategic chops.

Presenting – Again, another area where you just have to practice. I was terrified to speak in front of senior people when I first started out. I found getting into karaoke was a good way of tackling the shaky knees phenomenon. Then, once you’ve conquered straight-up fear, learning how to organize your thoughts and how to rehearse is crucial. Luckily, if agencies are going to pay for any training, this is often an area they are willing to invest in. I’ve been through four different presentation skills seminars and they were ok. You’d be surprised what you learn simply by watching a recording of yourself and learning to take feedback from your peers. But I have recently learned about a company called Oratium that conducts a workshop that is supposed to be great and I hope to attend. Last, I’ve been exploring Improv classes and stand-up comedy to improve my dexterity with humor, which is my natural style. Oh, and check out a Pecha Kucha night if there is a chapter in your city. It’s a great way to be both exposed to many different disciplines and ideas (for your lateral thinking) as well as presenting styles.

Creative writing – Last up – creative writing. While I have an English degree and thought I was a decent writer, I know that working through the process of writing a book and especially working with an editor has made me a much better one. Write for your own blog, guest blog, submit articles to publications, or start writing a book even if it’s a long-term goal. But no matter which path you choose, hunt down a pro-editor and invest in having a piece of yours revised. It took me four tries to find Marissa van Uden, and then she chewed through my whole book twice. If you can find the right tough love, you will get better.

That’s my starter for ten, dear anonymous strategy friend out there somewhere. Now I’m curious to see what the rest of our brilliant tribe will add.

11 thoughts on “What would you do?

  1. I’d say, on top of the excellent advice above, make sure you have the basics of strategy/planning nailed. Go to an APG course, find an old school mentor. Follow the best on Twitter, seek out their slideshares, learn. Apply the thinking wherever possible. Ask your colleagues to indulge you to try new things. Read the heavy duty stuff in the media like Warc. Apply that.

    Work out where your strengths are and use them wherever possible.

    Connect with a virtual network of strategists. Pretty much everyone I’ve spoken to outside the huge capital cities feels alone – but there’s so many people out there to connect with, you don’t have to feel on your own.

      1. Cool, I’ll check the book out!

        Weaknesses are a funny thing. Theres a difference between the ones you can work on and the ones that are permanent. I guess it helps to know the difference!

      2. Yep, Strengthsfinder is an excellent tool, definitely second that – it’s in part thanks to that test I was able to articulate why I’d be a good strategist. I took the test while I was looking what I wanted to do next. Also brilliant to manage teams in a way complementary to everyone’s strengths using their classification in 4 categories (Executing / Influencing / Relationship building / Strategic thinking). All the texts & docs are online now. http://www.gallupstrengthscenter.com

  2. Heather, you’ve done a great job tackling this and I agree with all your suggestions. I especially like the part about writing. It is an art I believe deeply in and attempt to get better at every day. A wise copywriter, Mark Fenske, believes that strategists write far more than copywriters. So make that a hobby. A ritual. A daily exercise that sadly won’t garner you steps on your FitBit, but will make you a more compelling presenter. Also, I would think that another possibility might be some improv training. I think a scientific background can be great for strategy – solving problems/applying a process. But planning and strategy can also be very messy. Embracing the messy – saying “yes and” could be great practice.

    Unfortunately, not all supervisors are great. It takes time in the job – to go from being the “doer” to being the leader and director of doers. As I look back on my career, the early years were more like an apprenticeship. I watched what my boss did. How he handled meetings. I read past documents, presentations, reports. I dare say I “copied” a bit before I developed my own skillset. Don’t wait for this to come to you. So if your boss isn’t great at mentoring yet, then go in search of what you can do on your own. Mentorship also takes time. Have you suggested a way to find time for those kind of discussions?

    The idea that your mentor and your supervisor are the same person isn’t true. Sometimes my best mentors were not the people I reported to. Were not even in my company. So connect with people you meet in the industry – just as you have here with Heather. Try to attend conferences whenever possible. They don’t all have to be expensive and they don’t all have to be about this industry. But exchanging ideas with sharp people is its own form of mentorship.

    I don’t have all the backstory, but I hope something in here is helpful.

  3. Heather, maybe some volunteering mentorship every now and then with other planners could help. I’m game. Skype, email, texting, you name it. Put us in touch!

  4. Hello!

    It’s an all too familiar story, sad to say, especially when people have experience in other industries and working environments.

    I’ve not encountered structured planning or strategy training at any agency in the USA – feel free to correct me – but we have done immersion sessions and workshops on account planning, integrated comms strategy, insight generation, better briefing and so on with some agencies that still have training and education budgets.

    As to what I would do. Hmm. First off, yes, working has shit sandwiches, agency life is hard, and some of it yes you just put up with. Sometimes you need to stay a year to make your next employer not freak out – every 2 years is pretty standard until you get senior in agency land. BUT there are exceptions – if somewhere is obviously terrible, get out. Rosie left one big traditional agency after 6 months because terrible, get a job at a digital agency she loved.

    I believe one of the big problems in agencies in USA is how linear careers are. People are hired into the same job, in the same category. This leads to institutional calcification and a lack of empathy and understanding. Media people rarely move to creative, digital, shopper, research – but the more broadly you understand the landscape, the more strategic you can be

    {I would argue a strategy has to be able to allocate budget based on objectives, so if you are at an ad agency you can’t do strategy, only planning. But that’s semantics.]

    Well, I agree with Heather on don’t stay if you aren’t learning – although I would add in “or being paid A TON or HAVING A LOT OF FUN”. All three are valuable, depends on what stage you are at.

    Also – my book Paid Attention was built around a course I created to teach junior strategists in a structured way at agencies I worked at. I think it’s incumbent on senior planners and especially heads of planning and strategy to do this – it’s a core part of our job.

    So yes ask supervisor out, to the pub, drink and ask them to set you one piece of reading every week. Then ask to discuss it over a pint. At lunch. BOOM.

    If they won’t, they probably suck.

    So, yes, learn, speak, think, write.


    Books and blogs and rock and roll.

    here are some book reccos:




    And read Adliterate


    Presenting is A KEY PART OF THE JOB – A CORE SKILL. Way too many agency folk don’t present well enough. Speak, in public, at any opportunities.

    Think/ Create:

    Write a blog, make decks, and get them out there.

    Oh yeah COMMUNITY is key. for learning, for support, for jobs, for craft. Twitter! GET ON TWITTER. Or whatever platform you like. There are account planning facebook groups.

    Finally – learn to manage your agency, ask it for what you want. If you can’t get weekly sessions with CSO, what conferences are they sending you to? What do they give you, above a salary?

    Ask people there about tenure, about training, about moral. Then go out and ask other planners and strategists at events. Meet as many as you can. That’s part of why I set up beersphere.

    Oh and here is some generic advice from my book:

    And finally, you can always set up your own – but you need about 10years plus experience first. Here’s Merry on that


    HOpe that helps, Rock ON FX

  5. Hey Heather & mystery writer-friend!

    I wouldn’t have said much better than this post Heather, plenty of excellent ideas and resources in there. I’ll still add a few thoughts, because why not.

    There’s certainly something about expectations about what a mentor is and does in an agency, you may well be coming from a very different working environment. Agencies are pretty far any kind of academic or educational environment, in my experience learning in an agency meant being thrown in the deep end and that’s about it. They’re high pressure, fast environments most of time. If that’s not the kind of shit sandwich you enjoy eating, well I guess in doubt take a few more bites of it. At the same time I absolutely agree with Heather, a conversation with your manager / supervisor is in order to talk out those expectations. We work in the creative communications industries after all.

    When I started out in strategy, my managers didn’t have much time for me, so I sought them out. I asked to be on as many projects as I possibly could, requested to join and listen in during meetings. If I wasn’t sure of something I’d go ask for advice, I’d steal moments of their time bit by bit. As suggested by a few others, I’d get the rest of the support from fellow strategists out of the office: drink meet-ups, Twitter, blogs and comments like here, Trainings like with the APG, etc. There are many doors open, we’re lucky to have a big community of strategists around the world happy to support each other.

    I asked for other more experienced strategists’ time for coffees, emails, advice on a regular basis, I still do and I return the favour for others.

    It’s funny in the excerpt Heather copied from your email, you say you don’t want to play around – but that is how we learn though. On a pragmatic note, you weren’t just hired to learn, you were hired for a job. And of course many agencies could do better with their staff training & development. In the meantime you’ve got all the people like us available 🙂

    More specifically, here are a few links of stuff I recommend checking in case you haven’t seen them yet:
    – Neil Gaiman’s commencement speech for Uni of the Arts 2012: https://vimeo.com/42372767
    – I recommend listening to a few podcasts like Radiolab, Tim Ferriss, How to be Amazing
    – Check out Bob Hoffman’s talk at Advertising Week Europe (and read his blog) https://youtu.be/EyTn_DgfcFE
    – I’m sure you’ve heard of Mark Earl’s books (Herd, I’ll have what she’s having)
    – Ask more questions. In doubt, ask another question.
    – Scream & vent your frustrations on a roof top or something 😉
    – You best work will probably come from ideas and inspiration out of the industry, keep exploring & cultivating whatever it is you’re interested in outside of work (another reason for the podcast recommendations)
    – If you haven’t come across this post check it out https://www.linkedin.com/pulse/thanks-advertising-tom-demetriou-1
    – I could go on, for now I’ll finish with Monty Python’s Galaxy Song from The Meaning of Life. It does the trick for me to pick me up when it’s all a bit too much: https://www.youtube.com/watch?v=buqtdpuZxvk

    Have fun, play around!

  6. Thanks Heather for sharing wisdom gained.
    I highly recommend that anonymous strategy friend volunteer for new business. It is a pressure cooker assignment but will expand strategy friend’s network and force advocating for ideas (writing and presenting). I consider it skin in the game and even if the agency does not win account, strategy friend wins experience and kinship.

  7. Sorry for the late reply, but driving across the U.S. post career jump put me in a bit of a non-responsive head space.

    First of all, the above is smart and if any of it resonates with you – move forward on it. If it doesn’t, then don’t. But sincerely – all this thinking is fabulous, and I wish I had this kind of primer before I started my career. I’ll add a few bits. And the same rule – use what works, ignore what doesn’t.

    1. I am a big supporter of the strength focus in an initial build of your career, per Kate’s comment. When we are learning something new, we don’t know what we are missing on, because we have so many layers of lack of experience. Using our “superpowers” gives us instant recognition of our expertise, patterns and comfort zones. So to Heather’s point of getting “laser-focused” – YES. Pick that thing that you rock at and figure out how to apply it to your strategy role. Let it be the context on which all else will build.

    Also, do that with the content you absorb and produce. Absorb all the “strategy content” above, yes. Per Heather, learn new, yes. But also, take your specialty and dive deep and apply to your strategic thinking. In the beginning part of my career, I could observe the layers, behaviors and performance of baseball and comics really well. They were my passions. I had been paying attention to them for years. It was easy to take my observations and learning from those worlds and apply it to my strategic thinking for other worlds. Read Daniel Pink’s chapter on Symphonic Thinking in his book Whole New Mind for more on that.

    2. I completely agree with what Willem said about “play around.” Playing is how animals learn. We spend our childhood playing and being surrounded by story. Then we grow up and think it is time for working and logical argument development – because play and story are “childish.” They aren’t. They are fundamentally human. That is why they work for development when we are at the stage in life where all we are doing is development. Return to them every time you want to grow and learn.

    3. Sink or Swim. Trial by Fire. So used to these terms when we start in advertising. While there is some frustration to them – there is also possibility. Let me tell a story (see above.) I grew up in Louisiana. My father loves to fish and hunt. I do not. I asked him how he got into the activities. He told me, “Well I wasn’t into them originally. But when we moved to Louisiana as an adult, I noticed all the licence plates and such that labeled Louisiana as ‘The Sportsman’s Paradise.’ I learned that fishing and hunting in Louisiana were really great. I figured I might as well get interested in those things. If you decide to like what is world class in an area, you won’t be disappointed.” Wow. Did that ever jog me from my “fixed mindset” of how interests happen. Embrace the Sink or Swim.

    As someone who directed a Creative Strategy department at an art school in SF, I got many visual idea focused students. Often they had this story, “I came to be a graphic designer, but then I learned that the idea didn’t start there, so I went into advertising to become an Art Director, but I learned that the idea didn’t start there, so now I am starting Creative Strategy.” Exactly. Those of us who gravitate towards this career do so because there is no direction. There is no start. We are the beginning. We stare into the abyss of complexity and get things started. That is the hard part. Many people like culture, people, technology, and creativity. Many people are persuasive, optimistic, curious and passionate. Those are not the unique traits to the strategist. What sets us apart in my opinion is our willingness to make connections before anyone else has. Because it is really scary and difficult.

    Therefore, when uncertainty happens in our own career – we should embrace it. We should create our own strategy for ourselves. You want to be a strategist – be one. Jump in. And we should be playful with it. And do it using our superpowers.

    OK – there are my additional ramblings. Again, remember. Only take away what works and ignore the rest – that is for someone else – not you. 😉 (Thanks Heather for giving me a soapbox.)

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