Why you aren’t getting better.

3 reasons you aren't progressing.

There’s a whole cottage industry of “how to break into strategy” or “how to be a better strategist” content, and most of it is really helpful. But despite this being a golden age of people willing to teach you how to do strategy (seemingly only run by people who are trying to avoid working full-time in an agency ever again, which is a whole other email) I’ve noticed a lot of the same question popping up in conversations, on subreddits and on twitter: how do I get better at strategy?

I’m not interested in selling you a course, or a book, or anything other than there being more great and skilled strategists out there.

(My motives aren’t pure at all, btw. I just want to be able to hire great people more easily, so giving away advice is in my self interest. I’m not threatened by there being more great strategists out there, because 1) there’s more than enough work to go around, and 2) I’m confident that no advice I give in an email is as impactful as actually working with people day to day so they and I continue to improve.)

So: here are the three most likely reasons you’re not getting any better at strategy.

You’re only learning from the same people as everyone else.

I make a point of doing a lot of coffee meetings (virtually, now) with people who want to break into strategy. And one of the things I always say is that you can get a great grounding in how this all works by following and subscribing to content from Julian Cole’s Planning Dirty, Faris & Rosie Yakob’s Genius Steals / School of Stolen Genius, and Mark Pollard’s Sweathead. And you can. Follow them on social, subscribe to the free stuff (newsletters, podcasts, videos), go further if you see the value. You can build a sense of community, and understanding of key tactics, and some great frameworks and considerations and approaches you can borrow. You can also get exposed to great thinkers and new ideas from these sources.

They’re just the same ideas that everyone else is hearing (in this very specific niche).

There’s nothing wrong with that - I studied English literature in university and can tell you that just because everyone reads Shakespeare or Achebe doesn’t mean it’s not eminently worth reading. It just means that in an industry where divergent thinking is an advantage, your divergent thinking is pulling from the same sources as your contemporaries.

(This is the “best practices” problem. When a platform or channel tells you what the best practices are, it’s a list of 1) what everyone is going to be doing for the next year, 2) guidelines for how not to fail. These are incredibly valuable things to know, but generally reaching your next level is not something you do by following the best practices.)

Some starting points for other people to learn from? Adjacent industries (education, film / tv, and publishing all have interesting lessons to teach), the OGs (retired / legendary ad people love to write books about the good old days and the first principles hold up nicely), and academics (imagine a ‘grown up’ version of our world, but with infinitely more rigor, peer review and patience) have all panned out for me at different times. The point isn’t finding a magic bullet, so much as diversifying the hell out of your information diet. Knowing something weird is a bonus, knowing everything weird is a superpower.

Confusing your style for your craft.

The worst thing someone can do early in a strategy career is decide that they have a personal style, and that projects, clients, teams and agencies need to adapt to them, rather than the other way around.

I’ve seen people use the “style” defence to push back against internal standards, critical feedback, and even deadlines. I get the allure of it, and in any creative field personal style does play a role. But you can’t really focus on your style until you’ve made headway into mastering your craft.

Being very good at delivering a strategy, or an analysis, or a brief in a specific way is great, but it’s not as useful as being able to do each of those things in ten ways, each tailored to a specific situation, client, collaborator or constraint.

Where this really becomes harmful, is when someone with a style that fits well with an agency, becomes management. This is when you see an entire department delivering work in a way that fits the preferences of a leader, rather than the needs of a problem or a client. Training a team of people to act as though your personal style is the only good way to develop a strategy, is both egotistical and ineffective.

Having a style is important, if only so you can elevate the work beyond the process and make it feel more engaging and alive. But if you spend anywhere near as much time working on your style as you do your craft, you’re going to be delivering really limited work in really elegant slides.

Working to the wrong audience / objective.

Everything done at an agency has several audiences. Bad work happens when you pick the wrong one, and unfortunately, you will be constantly encouraged to pick the wrong one.

If you’re writing a brief primarily to get it approved, rather than primarily to get to great work, it’s not going to be a great brief. Similarly if you’re writing a POV to get to make an NFT recommendation because you think it will win awards, it’s probably not going to be a great POV.

There will be a constant temptation to do the work in a way that doesn’t make the work good or effective, but instead makes it convenient or easy. The path of least resistance generally doesn’t lead anywhere you’re interested in being, in my experience.

The key isn’t in being obstinate and insisting that only you know the one true path. It’s in ranking your objectives and audiences properly - yes you want great work, but you want great work the creative team wants to work on, and that the client is happy to pay for (usually in that order). This is harder than just aiming for a happy client, so many people just… don’t do it.

My work got better when I stopped worrying so much about what stakeholders wanted, and started worrying more about what they needed. It made my job harder (sorry) because it requires a lot more skill and effort to convince someone to pick the thing that you believe will help them the most, rather than giving them a thing that’s really easy for them to pick.

The same can be true, by the way, for working to the internal review. If you have even a half-decent boss, they’ll encourage you to disagree with them (assuming you have an argument rather than a preference). Don’t focus on giving people they thing you know they’ll accept, give them the thing that you know will move the needle.

YMMV

I can’t guarantee these are the three problems that you specifically are running into, but they are the most common ones that seem to come up when someone feels ‘stalled’ in their development.

I almost didn’t write this, because the only thing strategists and aspiring strategists talk about more than wanting to grow and improve, is the impostor syndrome they feel despite evidence of their growth and improvement. In my personal experience, the best solution to impostor syndrome is to do the damn thing, because being bad at something is intrinsic to being great at something. Your job as a strategist, possibly more than anything else, is to be able to be wrong a lot, and consider that part of the process of getting to something right.