The best strategy career advice I’ve found so far (curated from the minds of 50+ strategists)

Alongside my comms and social strategy consulting, I run a strategy collective. It’s currently made up of 300+ members, from 17 different nationalities, across all five continents. In-house and agency side. Mid-weights to heads of department. A fun bunch.

Every other week, we organise an Ask Members Anything session that’s exclusive for members, called The Shoal. Every person brings a question, and answers others’ questions. We all benefit as a result.

This is a running list of all the questions and answers offered so far, from a range of topics like ‘how do I improve my writing?’ to ‘how do I position myself?’ to ‘how do I move into a new niche?’. Once upon a lifetime, I wrote about 50 hard truths learned from 15 long years in strategy, but these days I prefer to curate the advice that others are giving out.

As we do more sessions, I will keep adding new questions and answers at the top. I hope there’s something in here that helps with a question you’ve been wrestling too.

Wanna come to the next one? Join our strategy collective.

“How do you balance essentialism* with having many irons in the fire?”

(*Essentialism is the disciplined pursuit of less, popularised by Greg McKeown's book of the same name. It proposes focusing on the few things that matter most and deliberately cutting out the rest, rather than spreading yourself thin across many.)

  • Go narrow-ish. Pick 2-3 connected things, not just one. This is how you hedge your bets and avoid either being known for nothing, or narrowing down so much it’s not a profitable path.

  • Lead with experience. Lead with what you’re most experienced in. Take other work if it pays. Over time, you get a good sense of what’s actually good for business.

  • Do one thing at a time. Hold back ideas that aren’t fully baked yet. Talking them through can give you a false sense of completion, without finishing the actual thing.

  • Time-box activities. For example, reserve networking for Mondays, writing for Fridays, certain times of the day for project delivery, and so on.

  • Be ok with dropping things. Accept being okay with letting things slide. Imperfection is its own skill to practice. Use the rubber vs glass ball metaphor: figure out what bounces if dropped, and what shatters.

  • Think of it as as portfolio. Apply a 70-30-10 (or similar) model across exploratory, reliable, and experimental work. Adjust the split as your season of life changes.

“How do I incorporate more writing alongside my strategy work?”

  • Reframe big asks into small ones. Recognise that impossibly high standards prevent shipping, so you’re better off reframing big asks into smaller ones. For example, writing an essay feels like a lot of work. Writing 5 bullet point thoughts on a topic is much more achievable. And probably good enough to publish too.

  • Recognise that indifference is the enemy. Shipping something imperfect risks indifference, not hostility. No one will hate you, they’ll just ignore you. This is liberating.

  • Make it feel fun. Let impulse control be weaker than perfectionism. Ship what feels fun, without expectations.

“How does one wrestle with a passion for advertising strategy, with the reality that this job doesn't pay like it used to?”

  • Mourn what no longer is. Expect the industry to be less lucrative than it once was. That golden era is over.

  • Normalise salary chat. The more you talk openly about salary, the more you motivate others to also talk about it. Money motivates more people than we like to admit.

  • Weigh the tradeoffs. Agencies feel exciting, but it’s hard to switch off and hard to negotiate higher pay. In-house is less pay (especially in the US) and less exciting work, but clearer boundaries and better work-life separation. Freelance offers more freedom in theory, but can be the hardest scenario, both psychologically and financially.

  • Know the role of this job. Not every job will be hugely lucrative, intellectually stimulating and creatively fresh at the same time. This is probably the norm for most of us.

  • Adjust based on life stage. Have a clear goal in mind, and identify which era of life you're in while working towards that. For example, if earlier in your career, prioritise learning, graft, connecting, accepting you will be a bit skint and time-poor. Later in your career, you can focus more on freedom, fulfilment, or money.

  • Negotiate with every job switch. Negotiate hard at every job switch, they can only say no until you sign. The biggest pay rises tend to happen by switching jobs.

“How do you manage burnout and avoid overly high standards?”

  • Accept ‘good enough’. Adopt ‘good enough’ as a deliberate, sustainable philosophy rather than white-knuckling through everything. Not everything needs to be perfect all the time, especially if that destroys you.

  • Lean into your strengths. Lean into what you’re actually good at rather than forcing struggle. Over time this becomes more natural, as you learn your natural rhythms and accept that others are better at some jobs than you are, but you’re also better at other jobs.

  • Reframe micromanagement. Constrained autonomy (e.g. a micromanager) can be seen as freed-up space for other pursuits. There’s only so much you can control.

  • Find the biggest source of value. Friction does not equal progress; look for disproportionate value instead of just feeling like you’re doing work for the sake of it.

“What are some ways to make virtual creative briefings engaging that don't feel cheesy or gratuitous?”

  • Get to the point. Avoid front-loading briefings with 15-20 slides of research before stating the ask. Lead with a three-sentence summary, then open the floor for discussion. Let creatives play back their understanding of it, so you can validate or redirect early on.

  • Play with formats. Experiment with interactive formats (e.g. HTML tools built with AI) or skip the deck entirely and just have a conversation

  • Go visual. Use rich visual language and metaphor to give creatives mental jumping-off points; match visual specificity to the individual creative to avoid overly literal interpretations.

  • Personalise it. Get to know your creatives and tailor your briefing to their preferences and skillset. Lean on your creative director to get a good sense of the latter.

  • Treat briefing like flirting. Give just enough to spark curiosity rather than exhaustively informing.

“How do you convert warm leads from speaking engagements or networking?”

  • Manage expectations. Assume a 6–12 month sales cycle, and set expectations accordingly.

  • Lead with curiosity. Use curiosity-driven outreach, e.g. "I'm really curious how solving tricky problems plays out in your role. Can I get you coffee to chat?"

  • Make it about them. Offer to buy coffee and learn about their world, and make the follow-up conversation about what they’re going through, not about you (yet).

  • Build mental availability. Focus on becoming a known entity in your niche so people recognise your name when you reach out, as this tends to increase your response rates. You can do this through industry involvement, e.g. joining professional groups, speaking at events, judging awards, lecturing, writing publicly.

  • Sustain the relationship. Avoid immediately asking for business, focus on building the relationship and being mentally available over a sustained period of time. Stay in touch consistently, monthly or bi-monthly, with light touches, e.g. "Saw this, thought of you".

  • Learn to spot problems. Watch for signals that someone has a problem you can solve, then offer to discuss it, but don't force the chat. If it happens naturally, great. If not, then focus on maintaining the relationship.

  • Make the trial easy. Offer free 20-minute audits or intro sessions as a low-stakes way to show your thinking. Or use discounted or half-price intro sessions to give prospects skin in the game without full commitment.

  • Anchor your prices. Always anchor to full price first, then offer the discount as a one-time deal. Avoid offering ‘cheap’ rates, go either full price or free to avoid anchoring yourself to a low price point.

  • Stay flexible early on. Address immediate client needs even if they're not your ideal long-term project.

“How can we package our offering to clients while being respectful of what they need or can implement?”

  • Develop tiered offers. Tier offerings by complexity, time, and level of engagement, not just deliverables.

  • Break deliverables. Turn a single, broad discipline (e.g. brand strategy) into separate products (e.g., brand guide and messaging guide as two distinct offerings).

  • Phase it out. Phase proposals into manageable chunks, so clients can digest and implement gradually. Use an MVP (minimum viable product) approach: sell a small first phase, then propose additional stages as you go.

  • Know your clients’ personality type. Profile clients by their character and bandwidth, and adjust scope based on how cautious or ambitious they are.

  • Workshop the problem. Sell the problem definition phase first as a standalone workshop, which naturally leads to selling the solution phases. Make sure you do charge for scoping or discovery workshops, rather than giving them away for free.

  • Discount carefully. When offering discounted intro sessions, clearly frame them as "intro" or "first session" to imply there's more to come.

  • Manage perceptions. Establish a transactional relationship early (even if discounted) to maintain power dynamics, and avoid being seen as a free resource.

“How do you position brand storytelling work in business contexts?”

  • Reframe your language. Consider using "narrative" instead of "storytelling", it sounds more mature and business-focused. Avoid the word "brand" with financial or senior business audiences, because they often see it as fluffy.

  • Make it about customers. Reframe brand strategy as "bringing the voice of the customer into the boardroom" or "understanding what customers think and how to talk to them".

  • Talk about demand. Talk about "generating demand", "building customers", "consistency," and "favourability" instead of abstract brand concepts.

  • Sell the consequence. Frame your work not in terms of creative or emotional benefits for customers, but in terms of consequences to the organisation, e.g. integration, clarity, autonomous decision-making, avoiding costly mistakes. Strategy is about "creating consequence in the business" by encouraging action and decisions, not just more slide decks.

  • Commiserate (a bit). Use commiseration as an icebreaker, for example discuss common industry problems in abstract terms to gauge client interest (e.g. talk about how brand, comms and social teams rarely speak the same language, and how this gets in the way of shipping good work). But don’t over-do it because, unless you already have existing rapport with clients, you may come across as too negative to work with.

  • Make it feel casual. When discussing problems, do it conversationally ("Isn't it frustrating when...") rather than directly accusing the client of having that problem.

“What's your best advice for transitioning from creative director to strategist?”

  • Know you’re already sort of there. Recognise that many senior creatives have already learned strategy out of necessity due to poor briefs. Look for opportunities within your current organisation to demonstrate strategic thinking.

  • Focus on good problem definition. Get better at problem definition, as this is central to all strategy work.

  • Go hybrid first. Seek out hybrid roles first, to establish a reputation as a "strategic creative". Use your creative training to your advantage: be selective in what you show, focus on impact, don't feel the need to show all your work or show how smart you are (which us strategists looooooooooove doing)

  • Use your conviction. Creatives often have strong taste and perspective, which is invaluable at more senior strategy levels.

  • Manage your cognitive loads. Be mindful of cognitive load because strategy requires different mental space than creative ideation and execution, or at least give your brain some time to navigate between one and the other.

  • Keep an eye on the prize. Remember that strategy should serve creative (in agency contexts), but don't let that diminish the value of strategic thinking, especially when you work with agencies who don’t just do advertising, or more in-house roles.

  • Formalise it as you go. Build informal strategy experience through your current work, then formalise it through training, reading, and community involvement. It all adds up.

“How should I talk about brand frameworks with small businesses?”

  • Go anti-corporate. Ditch complex corporate frameworks entirely. Small businesses are already human, so the goal is to codify what already exists, not impose new structure.

  • Build a one-pager. Build a simple one-page brand document anchored in founder personality, customer language, and a handful of distinctive attributes. Beats long decks any day.

  • Simplify competitor audits. Mine competitor reviews (last 100 per competitor) to map current category associations and buying occasions. Sometimes this is plenty to get them started.

  • Prioritise your actions. Use a now-next-future audit: identify where the brand is, then prioritise 10 actions across timeframes.

“How do I position myself as an independent strategist?”

  • Trial and error. Expect 1–2 years of iteration. It's a process of elimination by knowing what feels right and what the market responds, not a moment of clarity that comes out of a sudden.

  • Start with what you don’t want. Work backwards from what you don't want to do. The niche emerges through exclusion as much as aspiration.

  • Know what leads vs supports. Anchor everything in a single pithy positioning, then layer complementary skills underneath it.

  • Follow the money. Focus on sectors where clients have budget, not passion projects. You’re now in charge of your own biz dev.

“How do I improve my networking skills?”

  • Frame it as research. Use genuine research conversations as your primary outreach ("I'm learning, can I ask 5 questions?").

  • Find adjacent consultants. Build referral networks with adjacent consultants (brand, web, ops) rather than chasing direct buyers. Makes it easier to get intros without the hard sell.

  • Avoid marketing events. Attend industry events where actual decision-makers are, not marketing events full of consultants.

  • Protect your time. Cap calls per day, week, and month, so networking doesn't crowd out delivery.

  • Be generous. Be generous on LinkedIn without expectation. Comment on good work, compliment freely, don't keep score. Freelancer karma is some magic shit that eventually works.

“How do I do a brand audit on a budget?”

  • Combine AI and social listening. Use AI queries to surface how a brand is perceived externally. This already gives you baseline to work with. Then cross-reference with Reddit and Facebook mentions, for a more unfiltered customer voice.

“Where is the growth in strategy jobs in 2026?”

  • Comms strategy has more frequent demand than brand strategy. Brand tends to be a once-every-few-years investment, whereas comms is ongoing, which matters a lot if you're billing by project.

  • The UK market feels particularly difficult. The more interesting opportunity is going direct to clients rather than through agencies, and looking beyond the UK.

  • No one cares about brand strategy on its own. People care about things linked to more direct outcomes and ROI. The framing and the link to commercial impact matters more than the discipline label.

  • Follow the money into growing niches. Even if that means pivoting away from sectors you love. B2B and food tech were flagged as more resilient right now compared to hospitality and food-and-drink, where thin margins are squeezing clients hard.

  • Beware of echo chambers when reading the market. It's easy to mistake what you're interested in, and therefore what you're being served, for what's actually growing. The algorithmically reinforced bubble can make trends look bigger than they are. Always good to compare notes with folks who don’t do what you do!

“How do you sell strategy to non-marketers, e.g. founders?”

  • Lead with the output, not the process. Founders respond to deliverables, e.g. a piece of language that rallies an internal team, a comms plan, a case study with what changed. Three words as an organising idea sounds absurd until you explain what it unlocks.

  • Don't pitch, interview. Asking someone if you can interview them for 30 minutes for research you're doing has a surprisingly high acceptance rate. People love talking about themselves and their problems. You're gathering intelligence, but you're also starting a relationship without the awkwardness of selling.

  • Offer something at the end. A good tactic after an interview is to offer the interviewee a free hour of your time to think through one of their problems. It rarely gets taken up immediately, but it seeds something, and you’ve already demonstrated your thinking during the chat.

  • Keep outreach short and punchy. Long messages trying to add value upfront don't perform as well as direct, low-stakes asks. "You seem interesting, can we chat?" works well enough. Brevity can signal confidence.

  • Position yourself as the expert from the start. Rather than waiting to understand a client's problems before offering a perspective, come in with a strong, named point of view, e.g. here are the three things startups get wrong about X. That posture opens doors in a way that "I'd love to learn more about your situation" does not. You may not always get it right, but now you’re having a tangible conversation about something they care about.

“How do you productise strategy work?”

  • Clients don't pay for thinking, they pay for artefacts. Strategists who can name a deliverable, scope it, and put a price on it are in stronger commercial positions than those who sell themselves as smart people available over a period of X amount of hours or days.

  • Build a menu of deliverables with prices attached. Going through your work and pricing each output, e.g. audience snapshot, comms framework, messaging matrix, gives you a ready-made proposal toolkit and makes scoping much faster. Also, see above: tangibility.

  • Productise what's labour-intensive, not what's core. Research, competitive reports, ongoing monitoring, these are good candidates for productised offerings. The actual strategic recommendation, the "this is what you should do", should stay fluid and expert-led. Productising that dilutes its value, so avoid doing it.

  • Aim for a “fast no”. Being opinionated early is a feature, not a bug. Clients who don't like your point of view aren't your clients, and finding that out in week one is far better than finding it out in month six. A “yes” is good, a “fast no” is good, a “slow no” is what’s terrible.

  • Add a socialisation phase. After delivering brand or comms strategy work, a short extension of scope focused on helping the internal team socialise the output is undervalued and undersold. The brand team in the room for a presentation can't always capture the reasoning for everyone else. Help them do that.

  • Don't over-productise. Too many products creates the same problem as too many flavours of jam, i.e. decision paralysis. Keep the menu focused. Starting with three core products is not a bad way to build your confidence.

“How do you find time to read stuff?”

  • Make peace with not having all the nuance. The trap of reading is trying to absorb everything on the page and therefore feeling you’re never fully done. Instead, it’s ok to get the gist of things and the feeling that a piece of writing either introduced a new thought on your head, or it didn’t. AI summaries, in that sense, can help us have a much more varied and interesting media diet over time, not to mention a more sustainable one too. Probably.

“How do you promote yourself?”

  • Being known for something specific is more valuable than being broadly impressive. A precise area of expertise, e.g. a subculture, a sector, a type of problem, becomes a "category entry point" in people's minds. When they need that thing, they might think of you.

  • Content plus outreach beats either alone. Publishing on LinkedIn doesn't always lead directly to work, but it creates warm context and recognisability. When you reach out to someone cold, there's a chance they've already seen your thinking. The two work together.

  • Optimise your content for what excites you, not for what will perform. The best content often comes from genuine enthusiasm, and being a nerd about something, rather than trying to produce what seems absolutely correct or crowd pleasing. People can tell the difference.

  • Relational skills are increasingly valuable precisely because they're hard to automate. Active listening, creating psychological safety in client conversations, working with what's in someone's head rather than what they explicitly say, these are skills worth investing in alongside technical craft. Part of building a reputation is also being known as someone who’s easy to work with.

“How do you move from a freelancer who fills gaps to a brand that attracts clients who want what you offer?”

  • Get precise on what you do and who for. Define your expertise area and the categories you serve, plus the specific inflection moments when clients need you (e.g., when they're ready to scale but need both speed and rigor) 

  • Map who's hiring you. It's not always the CMO. Could be heads of science, fundraising, impact, behaviour change, strategy, or founders of smaller businesses. Once you know what you do and who for, it becomes easier to determine who actually pays the bill to bring someone like you in.

  • Use Venn diagrams. Overlap which sectors do that work, which are growing, and where the biggest problems/threats exist (like vaccine hesitancy as a global health threat). This helps you narrow down your ICP instead of just assuming your thing is for everyone. Which technically, sure, but also that’s not a very effective go-to-market strategy friends.

  • Out-niche your niche. Go deeper into specialisation, consider specific verticals or even specific deliverables within your field. There’s always one row you can go deeper to become known as the best person for that particular thing.

  • Build a collective. Partner with other specialists who focus on complementary areas. You’ll always be stronger together than trying to do everything, plus this allows you to have a precise positioning for yourself while still being able to tap into complementary experts for other types of projects.

  • Focus on precision over breadth. Being memorable for one specific thing (e.g., "thorny healthcare problems requiring behavioural thinking") makes you more referable than being able to do everything. Your positioning isn’t meant to capture everything you do, just the most memorable thing you do. Everything else can be an in-market conversation after.

“How do you move into a new niche (like B2B/tech) without burning bridges with existing niche (like food)?”

  • Comment strategically on LinkedIn. Find 10-15 target people in the new sector and comment thoughtfully on their posts. Comments have better reach than posts and help you find your people, plus you won’t alienate current followers.

  • Find the overlap. Look for sectors that bridge both worlds, like food tech, catering B2B, or companies like Soylent that span consumer and B2B. There’s always an interesting niche waiting for you when you cross two unexpected things.

  • Interview people in the space. Use conversations as content, either by featuring specific people or synthesising learnings from multiple conversations into posts. This is how you get around the “I have nothing to write about” slump, just write about stuff you’re already discussing with experts.

  • Focus on what you care about. Talk about what genuinely interests you (e.g., making complex things simple, adding personality to boring industries) rather than just the subject matter. People in that world will recognise shared values.

  • Appear on niche podcasts. Example of Dale Harrison doing statistics/science-backed marketing on LinkedIn but getting B2B pharma work from podcast appearances. It might make sense to find folks who have a bit of a platform in your desired space but not too much of a platform yet, which means they’re more eager to meet new guests (like you!).

“How do you find freelance projects outside of your current location (UK)?”

  • Post about going freelance. One simple Friday afternoon LinkedIn post about going freelance led to both a freelance project and eventual full-time job offer from New York agency. This may not always work for everyone of course, but don’t ask don’t get! (Just don’t ask too desperately.)

  • It's a numbers game. Spend time talking to people in target markets to increase surface area. Most time on LinkedIn should be DMing people, not just posting, because organic reach is consistently getting crapper. DMs are not a guarantee of response but 10% of them might yield a response, and then 10% of those conversations might yield an actual gig. Now you just gotta do the maths…

  • Ask for introductions. People like being seen as good connectors. Always ask "Who else should I be speaking to?" 

  • Be strategic about markets. Choose based on both budget availability and cultural fit (e.g., US for bigger budgets and faster pace vs UK's oversaturated and low growth market).

  • Target independent agencies. Indies are more open to freelance help, faster at onboarding, and easier to work with than big networks that are contracting and mostly trying to stay afloat with the people they already have.

  • Consider "big fish, small pond". If bilingual or from elsewhere, less mature markets may value London experience highly (though rates may need adjustment).

  • Pivot to adjacent skills. Explore ethnographic research projects or other aspects of the work you enjoy beyond core brand strategy, so that people have more specific entry points and specific use cases they can link you to.

“How do you manage building something while working full time?”

  • Use waitlists. Some people discreetly announce upcoming availability and let interested parties join a waitlist for first dibs (though effectiveness varies).

  • Tap friends and family network. Former bosses and colleagues who know your work may have projects ready. Though many won't materialise, some will. Worth a shot.

  • Expect some overtime. You may need to absorb consulting time while still employed, leading to 3 very tiresome months during notice period until you’re on your way.

  • Reality check. On the other hand this may create weird tension, because the freelance client knows you're juggling, your availability will be unpredictable around pitches at main job, and it's really funky when you can’t attend a meeting because you, checks notes, oh yeah still have a full time job.

  • Build cash reserves. Have enough runway for slow months, especially month 1-2, because even if you get lucky with the first gig then you need to have enough reserves to keep going. As they say (who’s “they”?), cash breeds confidence.

  • Use LinkedIn for relationship building. Even while employed, use it to build relationships, play matchmaker, and stay open to possibilities without knowing exactly what will work. TL;DR: Build future demand before you need it.

“What do strategy directors look for in their team’s AI skills?”

  • Assume everyone knows the basics. Standard platform familiarity is expected, focus on differentiation instead.

  • Show thought partnership. Demonstrate how you use different LLMs for different purposes and why.

  • Build practical tools. Can you build an agent? A brief builder? Tools that democratise work and make things easier for everyone? How can you show your work, working?

  • Show when NOT to use it. Demonstrate you know AI should never be the final output. Use it as sparring partner but find your own voice. Show when you’ve chosen not to use it at all.

  • Share experiments. Show unique applications you've discovered, not just obvious use cases like analysing 4,000 PDFs of award cases. Find the biggest bottlenecks of the job and proactively build tools that can help alleviate that.

“Is ageism still a thing in strategy?”

  • Yes, universally: Especially in agencies, which are meant to be the more progressive of the lot and yet here we are.

  • K-shaped ageism. That said, there’s a nuance here that affects both more junior and more senior people. Healthcare agencies now say "we only hire senior people", creating bias against younger strategists, but then question if senior people will "roll their sleeves up". Basically you can’t win, unless you find ways to carve your own autonomy out there. 

“How do you adapt your freelance work schedule to match your natural brain rhythms?”

  • Run a one-week schedule experiment: Stop forcing yourself into a rigid 9-to-5 structure if your brain does not fully wake up until 11am. Pick a realistic start time for one week, commit to a morning routine, and track your actual output rather than the hours spent staring blankly at a screen.

  • Use "fixed anchors" to compress your day. Schedule non-work commitments, such as a 2pm run, a gym session, or childcare drop-offs, directly into your calendar. These hard stops naturally eliminate aimless procrastination by giving you defined, focused working windows.

  • Establish core client hours. Set clear availability boundaries with your accounts, for example, Monday to Thursday, 10am to 3pm. This anchors your client-facing day while protecting your early mornings or late evenings for guilt-free deep work or essential rest.

  • Unlearn the agency "timesheet mindset". When you work for yourself, productivity equals deliverables, not hours logged sitting in an office chair. Shift your psychology away from "Did I work eight hours today?" to "Did I move the project forward?".

“How can creative and strategy professionals overcome industry burnout in 2026?”

  • Decouple personal identity from client work. Separate the "money part" of your job from the "meaning part". If client briefs are feeling flat due to widespread AI disruption or tight budgets, look for creative satisfaction elsewhere, whether through personal writing, side projects, or local community involvement.

  • Recalibrate your expectations. Accept that you cannot always simultaneously have prestige clients, perfect briefs, top-tier income, and massive societal impact. Pinpoint what you need most right now, such as cash flow versus creative freedom, and optimise for that single variable.

  • Find your intrinsic "why". Focus on a core, transferable skill that genuinely motivates you, like pure problem-solving or connecting disparate dots, rather than the specific glamour of the end product. This makes unglamorous or varied freelance gigs feel far more coherent, or at least more enjoyable to execute.

  • Embrace a pragmatic, mercenary attitude. It is entirely healthy to treat some portfolio projects purely as a pay cheque. Do a stellar, professional job, collect your fee, and actively invest your emotional and creative energy into your life outside of the business.

“How do you build authority and confidence in senior client meetings?”

  • Default to brevity. True confidence is expressed through concise answers. Speak with composure, deliver your strategic point, and then stop talking. Over-explaining signals underlying anxiety; brevity signals absolute authority.

  • Deploy the "Instinct + Verify" framework. If a senior client hits you with a hyper-technical question outside your current depth, do not attempt to bluff. Say: "I don't have the exact data point on hand, but my instinct based on X is Y. Let me verify that and follow up with the precise details."

  • Flip the script with clarifying questions. Redirect intense questioning by asking, "What have you tried previously in this space?" or "Why is this specific methodology critical for this phase of the brand?". This shifts conversational control, demonstrates your rigour, and reveals if the client is genuinely exploring or just seeking validation for a pre-existing view.

  • Pre-game the meeting with AI insights. Before stepping into the boardroom, research your clients' public LinkedIn content or thought leadership and run it through an AI tool to decode their communication styles, potential biases, and strategic priorities. While it is not a silver bullet, it works wonders for building rapid empathy.

  • Assume best intent. Avoid entering rooms expecting negative bias based on your age or gender. Staying neutral and objective keeps your confidence intact and prevents you from slipping into unnecessary defensiveness. Bias may well exist, but you can prepare for it without actively expecting it to happen.

“How can strategists effectively retain and manage knowledge in the age of AI?”

  • Prioritise simplicity over complex engineering. Avoid hyper-optimised, multi-tagged database setups that take hours to maintain and eventually collapse. Use a simple, searchable repository, like a single Google Doc for core philosophical quotes or a few broad Google Drive folders for your PDFs.

  • Practise active recall to cement ideas. Passive filing does not equal genuine learning. To truly integrate a concept into your mental models, play it back in your own words. Write a summary, record a quick voice note, or explain the idea out loud to a colleague, or even your children, if they will tolerate you talking about market research.

  • Adopt a tiered ‘Information Diet’. Divide incoming industry content into three distinct buckets: information to merely be aware of, information to understand, and information to fully integrate. Only invest heavy memory and retention effort into the final, highest-value bucket.

  • Use AI as a retention sparring partner. Instead of just using artificial intelligence to store data, use tools like Claude or NotebookLM to interrogate your own understanding. Feed in a complex industry report you have just read and ask the AI to quiz you on it to instantly identify your knowledge gaps.

  • Normalise selective deletion. Accept that forgetting is a natural, healthy human filter. Regularly purge unread newsletters, outdated bookmarks, and digital clutter. If you have not looked at a note or brief in six months, delete it as a form of healthy digital hygiene.

Thanks for reading so far. I hope you found some of this advice helpful as you navigate the choppy waters of strategy, consulting and the independent life. If you want to come to our next Shoal, all you need to do is join our strategy collective.

Written by Rob Estreitinho, a comms and social strategy consultant and the founder of Salmon Labs. You might also enjoy getting my newsletter. 6,000 readers at a 60% open rate, read by agency and in-house strategy leaders from all five continents. Subscribe below.


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