AI + Strategy

Connections Helper for Brand Strategists

Build a connections point of view before the conversation starts.

Phillip Lee 12th Street Strategy Written May 2026

"Convince me that you have a seed there, and I am prepared to expect wonders."

— Henry David Thoreau
What's in this guide
1The connections conundrum 2How it works 3Step 1: Prime the model 4Step 2: Give it the brief 5Why this works 6An example
1
The context

The connections conundrum

Connections thinking is a strategic advantage for creative agencies. Consequently comms planners are in demand and in most creatively focused agencies are overstretched if they exist on the scope at all.

Like most problems there is an opportunity hiding in the connections conundrum. An opportunity for brand strategists to partner more closely with them.

The gap

In my experience, connections fluency is jagged in most strategy departments. Some brand strategists are adept at thinking about a concept through the lens of channel semiotics to help extend a concept's amplitude in media while others are not.

It's a gap that creates risk for creative agencies as we head into a more headless and agentic consumer world. As personalized AI and zero click discovery remake the traditional touchpoint map, the context of an idea becomes as important as the content itself. Matt Webb writes brilliantly on the subject here.

Strategists who aren't helping to develop a focused hypothesis around connections needs are creating opportunity costs for creative teams and real costs for clients, as research shows advertisers lose an average of 72 cents on every dollar spent in low-attention media environments.

One possible solution

This is a place where integrated AI tools can help. Not by replacing the connections planner but by helping a strategist show up to that conversation with seeds rather than a blank page. A challenge framing. A set of questions. A working hypothesis about where the opportunity lives. Enough to earn the conversation and give it somewhere to go.

Thoreau's standard is the right one here, gather some seeds and convince the room you have something worth growing.

2
The output

How AI can help

You describe the client and category, the problem or ambition, the concept or creative territory, the target audience, current channels, KPIs, and any relevant constraints.

It gives you three things:

1
A connections challenge type
Is this a reach problem, a relevance problem, a timing problem, a context problem, an integration problem, or a journey problem? Naming the challenge type focuses everything that follows. This is meant to be a provocation to get the team thinking, not a final answer.
2
Why this brief is that type
Not a generic definition. A specific read of what in this brief points to this type of challenge — a hypothesis the room can react to, push back on, or build from.
3
The key questions to answer
The inputs a real connections plan needs that you don't have yet. What you'd need to know before the plan can be properly built. These are the questions to bring into the room with a connections planner or media partner.
3
Step one

Prime the model

Start a new conversation in Claude, ChatGPT, Gemini, or whatever model you use. Paste the following as your first message. This sets up the framework the model needs to understand what connections planning is and what the challenge types mean before it can diagnose anything usefully. If you have a different definition use that one. If you have frameworks show them to the model to get it familiar with expectations. Context is everything.

Paste this into your model first
I'm going to give you a client brief and ask you to help me think about it as a connections challenge. Before I share the brief, I want to explain the concept of connections. WHAT CONNECTIONS PLANNING IS: Connections planning is the strategic layer between brand strategy and media execution. Brand strategy defines the what and why. The connections plan defines the how, where, and when the brand connects with people. Media planning finalizes the delivery. These are different but complementary jobs. Connections planning focuses and aligns marketing across paid, owned, and earned by taking business problems, budget constraints, brand positioning, creative concepts, and real media behaviors of the target audience into consideration to achieve brand and business objectives. It goes beyond paid media. It shapes message timing and impact. It helps to extend creative concepts into new formats. A connections planner understands the ad technology available to a brand but also understands the underlying culture and trends happening across media spaces and how to take advantage of them to maximize a creative concept's impact. For our purposes here, think of media planning as the downstream discipline that optimizes delivery and efficiency once the connections strategy is set. This prompt is focused on the upstream connections thinking, not the execution. THE CONNECTIONS CHALLENGE TYPES: Every connections problem is a specific type. These are the categories: - REACH: Not enough of the right people are seeing the brand. Scale or targeting problem. - RELEVANCE: The brand is visible but showing up in contexts that don't matter or don't fit the message. - TIMING: Right message, wrong moment. The brand is missing the window when the audience is receptive. - CONTEXT: The surrounding environment is undermining the message. Channel or placement creates dissonance. - INTEGRATION: Paid, owned, and earned are operating in silos. The idea isn't landing consistently. - JOURNEY: The brand is present at some stages of the decision process but absent at the moments that matter. WHAT I WANT FROM YOU: When I give you a brief, do three things: 1. Name the primary connections challenge type for this brief. If there are secondary tensions, name those too. 2. Explain specifically why this brief is that type of challenge. Use details from the brief, not generic definitions. 3. Generate 8-10 key questions a strategist would need to answer before building a real connections plan for this brief. Make them specific to the brand, audience, and problem. Push beyond obvious research. Do not build a connections plan. Do not recommend channels. The output is a diagnosis and a set of questions to take into a planning conversation.
4
Step two

Give it the brief

Once the model has the framework in context, describe your brief. Include as much as you have. The more context, the more specific the diagnosis.

Paste this as your second message
Here is my brief: CLIENT AND CATEGORY: [Who they are and what space they compete in] CONCEPT OR CREATIVE TERRITORY: [The creative concept at whatever fidelity you have it. If no current concept then describe the brand's positioning.] PROBLEM OR AMBITION: [What marketing needs to solve] AUDIENCE: [Who you're trying to connect with and what you know about how they engage with media] CURRENT CHANNELS: [What's in play today] KPIs: [How success is being measured — brand, business, or performance metrics] CONSTRAINTS: [Budget, timeline, competitive pressure, anything relevant] Diagnose the connections challenge and give me the questions I need to answer.
5
The logic

Why this works

This particular example is asking the model to do something it can genuinely do well: structural reasoning from a brief. It doesn't need real audience data or category intelligence to name a challenge type. It needs to understand what the different challenge types are and read a brief carefully enough to match the two. That's diagnostic reasoning, not synthesis.

You can expand on this and enrich the outputs if you input real audience data, KPIs, benchmarks, and channel-level sales data. That is a fundamentally different build but one that I can help you make if you're interested.
6
See it in action

An example

Here is an example of the prompts being used on a completely new ChatGPT instance in a logged out state. Imagine how much better this can be with all the context you have at your disposal.

From seeds to something more

What you see above is a two-message conversation designed to get a strategist from blank page to informed point of view in a few minutes.

If you want to grow from seeds into a real capability — one that lives in your team's workflow, learns from your past projects, connects to your research platforms, and helps every strategist think through connections problems with the same rigor — that is a different kind of build. If it's a conversation worth having, get in touch at phillipleestrategy.com/contact.

Two messages. A working diagnosis.

Built by Phillip Lee. Strategy leader with twenty years of experience building capabilities for agencies and brands including Apple, Google, Qualcomm, and Verizon.

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