Ideas for being a good strategist

A big shout out first of all to Rob Estreitinho who inspired this post full of ideas for strategists. I have built on his work. Some of the suggestions are what works for me or Rob and may not work for you – but give them a try.

Ideas

1. Read widely – thank goodness my Irish emigrant parents instilled in me the Irish love of reading. My Dad was an apprentice at 14, but has never given up a love of books if he had the chance. My Mum reads less with the lethargy of age creeping up on her, but they both seeded the idea of reading widely to me.
2. Get an RSS reader – find middle-aged people who used the net back in the early 2000s to early 2010s seriously and mention Google Reader to them and watch them go misty-eyed longing for forgotten online halcyon days. It didn’t make you depressed or hate yourself. While Google Reader is long gone, the underlying technology that enabled it is very much alive. It’s called RSS and Atom – same, same but different. All the RSS readers work along similar ideas; over time you find good sites, you follow them and get more good content from as they update. My tool of choice is Newsblur. But if you want to continue to rely TikTok, Twitter and Truth Social – you do you.
3. Your bookmarks are gold – on the bookmark bar of my browser I have a range of tools. I use Pinboard to keep every bookmark I have used in my work life for a long time. I go back through them to find quality content to start from for insights when kicking off a project. Anything you get elsewhere will be filtered through context and algorithm rather than quality. I also have a hard drive of old reports that I can go through and over-stuffed bookshelves.
4. Read weirdly – As a child I read everything in my Uncle’s farm house from the Connacht Tribune , Irish Farmers Journal to Old Moore’s Almanac and Ireland’s Own. Later on, one of the great privileges for me of going to college and then going to university, was the opportunity pick up odd books that would never have otherwise read. I would also browse County Books – a discount book store which allowed me to pick up unrelated academic books like Paul Stoneman’s Handbook of the Economics of Innovation and Technological Change – which is still invaluable today. Using an RSS reader and following other’s recommendations provides a similar opportunity. Finally, subscribe to Matt Muir’s Web Curios to get the edges of the web.
5. Make your arguments simple. – Going through this filtration process helps make ideas stronger as well as more accessible. My Myer-Briggs type is apparently INTJ ‘the architect’ – I have a clear vision of the thing. But going simpler allows you take stakeholders with you. Ideas only gain power as they pass from person-to-person.
6. Now make them simpler than that. When I thought about this, it reminded me of Matt Holt, who talked about good strategy being pain. This squeezing process is more than an expression, but a process that forms the quality of an idea.
7. Use simple words your mum would understand, or use simple words your mum’s mum would understand – as suggestions go were curiously Ogilvian in nature. However I when thought it, they were less helpful pieces of advice than they appear. Older people tend to be more articulate and may have more arcane terms. One thing generative AI does allow us to do is test how an idea would be expressed based on a notional character. So think about simplicity, through the lens of possible audiences.
8. Always start with a written document – I have found the notes.app on my Mac liberating. I can take my notes with me on my iPhone. I dump in links, language, ideas in to be played with and moved around. Insights and ideation become hybridised as a process.
9. Know a good meme account for the category you work with. If you don’t know one start with Reddit threads and you start to get a good feel for the themes and memes coming through.
10. Know a really good podcast your audience would listen to. Searching for podcast recommendations and listening to them can help you get into the right headspace for a given project.
11. Assume every problem has a fascinating side to it. If you work in strategy there are a few parts of the job to inspire your love of it. The ability to read around a subject, discover the problem at the centre of the challenge you are working, wrestle with that kernel of truth to give creatives something to work with. The process of wrestling the problem usually unearths the fascination at the centre.
12. Start your presentations with a twist. If you don’t have audience interested at the beginning, you won’t hold it until the end of your presentation. In terms of my personal writing, I use the background behind the number marking the edition of the newsletter to engage the curiosity of the reader.
13. End your presentations with a lesson. I like this as it reminds me of the old presentation training maxim: tell’em what you are going to tell’em, tell’em it, tell’em what you just told them. Ideas like advertising get better through repetition. The end summary can be just verbal, it doesn’t need to be in slideware.
14. If you’re feeling spicy, end your presentations with a cautionary note. Being provocative and interesting is good, BUT know your audience before attempting this.
15. Don’t obsess with strategy frameworks. Strategy frameworks have their place. They are great for establishing a common language – the classic example being the marketing funnel. They’re also good at dealing with the mental blankness that comes from an empty page or screen. But they can also be modified, built-upon or thrown away depending on what solving the problem needs.
16. Don’t bore your client with strategy frameworks. I’d argue, don’t bore your client. Their problems should be interesting, otherwise why would they get someone like you or me to try and solve them? If we are boring the client, there’s one of three things happening: you’re not solving their problem, you’ve gone off-mission away from the problem and the likely solution or the solution doesn’t solve the problem.
17. Remember the audience will never read your strategy. The only exception to this is the occasional Venn diagram-based advert creative.
18. Don’t interrupt people, especially when they’re demonstrating passion. Do remember to record it, otherwise you might be lost in the flow and lose the insights.
19. Notice what people say and play it back to them. This is a classic technique that is taught to salespeople and was in Dale Carnegie’s How To Win Friends and Influence People. It provides a number of benefits:
    • Ensures that you’ve understood what they wanted to say and you’re clear about it. It’s easier to get an explanation now, rather than later on.
    • Carnegie liked it because he recognised that people liked to be understood.
    • Allows you to build a common vocabulary with the other person.
20. Start sentences with “I wonder if”. Use this sparingly, but at the right time it is a powerful way of testing ideas and directions.
21. Observe people, but do so discreetly and don’t weird them out:
    • In coffee shops
    • At a greasy spoon cafe or the Motorway services station
    • On public transport
    • At trade shows. What stuff gets dumped from the collection of brochures they have. What way to people navigate a client’s stand. What seems to be attracting the most attention and the least? .
22. Say “I don’t know yet” when you don’t know… yet.
23. Don’t worry about memorising everything you read. If you can retain it all brilliant, but it’s not an exam, you can go back and check references if you are unsure. Instead it’s much more important to understand the topology of the problem and the direction that a solution would need to take.
24. Do use index cards – one of my favourite things on Amazon is sets of index cards and steel rings to hold them together in one corner. I use this to build my written memory on a clients business and products. I find the act of writing it down helps to build memory structures. I was inspired in this by Umberto Eco’s How To Write A Thesis.
25. Study ways to find out about things. I am a bit of a pack rat when it comes to tools, reports etc – as are other people I know. One of the areas that strategists have been ignoring up until now, but could learn a lot on in the hobbyist world of OSINT and your local library.
26. Use Claude AI to explain your own argument back to you – was a recommendation of Rob, I am using Gemini at the moment and it performs a similar role. However I do see the benefit of getting a couple of sets of viewpoints to pressure test your thinking. Previously, I would have done this with colleagues like Rob Fuller or Zoe Healey – generative AI kind of fills the gap and has some serendipity in its inherent weirdness. Whatever way you do it, stress-test your ideas.
27. Believe people when they say you did great, if it’s written down keep a record of it for your appraisal. But don’t let your personal sense of worth be defined by your career – you are more than your job.
28. Write with a thicker pen – it forces your handwriting to be clearer, letter shapes better defined. But use a thinner pen when thinking about structure and interconnections. I am a great believer when listening to talks or thinking about presenting a subject to mind map it out on engineering squared paper first. From the flow of interconnections, a natural order emerges.
29. Write with a bigger typeface – I would focus on legibility rather than size. And no comic sans – not even in irony.
30. Always change to 1.5 line spacing.
31. Don’t cheat on your one-pagers by making the typeface smaller. With generative AI now, why would you even do this?
32. Have strategy pals – but not to the exclusion of types of people. Try and have a diverse social network. It’s very easy to live in an advertising and media industry eco-system and out of touch with the general public.
33. Cmd+S every other minute. It’s a good idea to build this up as muscle memory, even if unnecessary in services like Google Docs and Office 365. Latency rather than a software crash are the most likely killer of documents nowadays.
34. Take care to manage your browser tabs, if you use a social bookmarking service, you can always go back to them later.
35. Buy a random magazine. Your clients might be all about social platforms but magazines, have been, and still are great windows into culture. I have a stack of Japanese style magazines for inspiration and try and buy a local magazine to leaf through when travelling. They are a fountain of future ideas.
36. Do a walking meeting. I miss doing walking meetings, at the time I had a colleague that lived within walking distance which made the process ideal. I also realise that this is often hard to do, when your project manager has filled you up on back-to-back calls. One thing I remember doing at Unilever was dialling into conference calls on my phone and listening in while walking around my office floor at 100 Victoria Embankment. Admittedly it’s not practical to do when presentations are being shared, or when your contribution is required to be engaged as a note taker.
37. Breathe while you talk. You have nervous energy, you want to get it all out. Breathing slows your thinking down so those finer elements won’t slip out of your grasp. I know people who swear by Toastmasters as a help to master this.
38. Daydream for no good reason. We live by the tyranny of the calendar on our phones or laptops and have lost sight of the time needed to think and let ideas worm their way out of our subconscious to the conscious mind at the front of our thoughts.
39. Have the basics of understanding wetware. The currency of being a strategist is people. We are the voice of the customer (people), clients (who also happen to be people) rely on us to solve problems, creatives rely on our translation of noise into something they, as people, can relate to. We don’t do all that alone, so thank people who’ve helped you and be generous with compliments. It won’t kill you, generally others won’t remember what you’ve done as much as how you made them feel.
40. Be specific. This manifests itself in lots of ways from reflecting the client’s problem back to being single-minded in a brief given to creatives. Specificity is its own form of clarity.
41. Listen more than you speak. Good advice for life, not just strategy.
42. Write a list. Lists are useful brainstorming device, but they are also really useful for self-organisation. Post-it notes are your friends.
43. Write a stream of consciousness and be prepared to cut and paste it around to organise your thoughts rather like ‘fridge magnet poetry’.
44. Give yourself 10 minutes to write the clearest answer you can think of. Simplify it in a few seconds with generative AI. Then feel ok that you’ll probably need time to get to a simpler one and remain better when the obvious simplification comes from colleagues.
45. If it feels obvious, stick with it. This reminded me of Dieter Rams principles of design which extend well beyond design and into problem solving and life in general:
    • Good design is innovative
    • Good design makes a product useful
    • Good design is aesthetic
    • Good design makes a product understandable
    • Good design is unobtrusive
    • Good design is honest
    • Good design is long-lasting
    • Good design is thorough down to the last detail
    • Good design is as little design as possible
46. Say your argument out loud. This is part of pressure-testing your own thinking. It’s also something that generative AI services can help with as both devil’s advocate and to ‘steel man’ your own ideas.
47. Admit when you are wrong. Being wrong isn’t bad, it’s part of the learning process and will help you get to better ideas. A former colleague of mine used to talk about being interesting as more important than being right – there are traps in that statement but also something powerful in it.
48. Say “sorry” when you have to. Sorry is a powerful disarming tool. It helps you get to both interesting and right faster.
49. Assume the work has been thought through. Just because you don’t get it, it doesn’t mean that others haven’t come up with some interesting ideas. And even if it hasn’t been thought through quite as well as you like, what’s the lesson that can be derived from it all?
50. Ask questions without judgement. There are no dumb questions, just people who are left dumber due to unanswered questions.
51. Find reasons to build on things. I found this a bit weird when I first entered agency life. Previously I had worked in the chemical industry, which was regimented and compartmentalised in the way work was done. College was very much about individual effort to complete assignments and essays. Build on this was something that I found female colleagues used to do really well. I remember being sat in a meeting and watch each person play a reverse ‘pass the parcel’ game with an idea. When it came to say their bit in a ‘brainstorm’ they would acknowledge what had been previously said and provide their own innovation as an additional wrapper. It won pitches and increased group cohesion.
52. Focus on agreeing a direction, not winning arguments. While you were winning the argument, you could have been getting insights to help set that direction in the ideas.
53. Build a robust strategy rather than a perfect strategy. A strategy that isn’t implemented for a client, may as well not exist. A robust strategy can be optimised based on what happens in the market. The perfect strategy may not even get to market.
54. Be useful. If a meeting needs coffee or printing off handouts and you can do them. People may not remember what you’ve done but how you make them feel and putting them at ease when hellsapoppin’.
55. Say you have a clash – leave it at that. Much of what happens inside agencies runs on implicit guilt. Avoid that guilt by saying less, being prepared to not fill silences and don’t explain diary clashes.
56. When you have nothing to do, read. Well learn at the very least, our world and what’s demanded of us is always changing. Do a course read an article, a book chapter or listen to an audio book.
57. If you’re tired of reading, write. I find writing very powerful. The process of writing helps me work things out from opinions to problem solving.
58. If you’re tired of writing, go for a walk. I was working on a brief prior to writing this post and walked from Whitechapel station home. I let my mind wander and I got the central concept of the insight by not thinking about it during that hour’s walk.
59. If you’re tired of walking, take a nap. Burn out is real, it’s got even worse with project management tools that overburden strategy teams.
60. If in doubt, try out the Oblique Strategies. Back in 1975, electronic musician Brian Eno and multimedia artist Peter Schmidt came up with what we’d call in advertising provocations. They are particularly useful in trying to break through a mental block. You have a 100 cards about the size of a playing card in a box. Read it, think about it, have a break and come back to it and ask how it can be applied to your problem. There is also an iPhone version of it, but there is something about the tactility of the cards.
61. Have a healthy snack of choice – our changing workloads chained to messaging apps rather than getting out and interviewing people in focus groups has amplified the need for this advice. I would go further and say avoid the ‘pitch pizza’ – the lowest common denominator selections provided by agencies to fuel the late night efforts of its pitch teams. I have turned to trail mix, zero sugar energy drinks and even Huel at a push instead.
62. Break your own rules. A former colleague that I worked with at Yahoo! used to talk about ‘guidelines, not tramlines’. Breaking your own rules is about understanding why you have the rule and making a creative choice. Usually rules speed up decision-making.
63. Make different mistakes. We learn from mistakes, there is a value in them if you think about things in terms of a scientific methodology. But, there is nothing to be gained from making the same mistakes.
64. Interesting is more important than right, I alluded to this earlier but it deserves its own explanation. Interesting sparks discussions that help get to further insights. This comes from remaining constantly curious and holding a strong point-of-view. As for views, hold on tightly unless there is good evidence to the contrary and then be prepared to let go lightly. This is where I again tell you are more than your job, one of the main ideas it is important to convey in a list like this.
65. Have a copywriter as an ally. Working on my last brief I had got to the the human insight, but I couldn’t land the concept in a sufficiently resonant way. Going back-and-forth with the copywriter got us there.
66. Have other strategists as allies. They have walked similar journeys to you and might see things that you are too close on to notice. One of the greatest aspects of working with great strategists is the collegiate attitude to ideas and generosity of thoughts.
67. Network internally. You would think that work would shine through, but the reality is most people won’t remember what you did. Secondly, that internal networking helps understand the context that your work exists within. Finally, the internal network you have will eventually become scattered across the industry and even client side, opening up potential future opportunities.
68. Develop an aesthetic. I was fortunate to grow up in a house that wasn’t wealthy in terms of money, but was wealthy in terms of ideas. Part of it was down to reading and part of it was down my Dad’s deep sense of quality. I would love to say that we had less but better in terms of consumption, but we didn’t – there are no Vitra or Eames designed furnishings at my parents house. The closest I have to it is the refurbished first generation Herman Miller Aeron chair I am sitting on and vintage Ikea birch bookcase – rather than their more commonplace MDF pieces. Much of my furniture is gifted or upcycled. My sofa, was originally from the 1970s, my Dad reupholstered it and rebuilt the frame based on materials he had left over from doing his own motor caravan conversion of a Volkswagen (Typ 28) LT-35 van. The sense of quality gave me the confidence to explore my own taste in design, art, literature and cinema. Taste and a sense of what’s important is becoming more important in strategy and the creative industries.