The GTM Problem Boards Don't Know They Have

Over the past few weeks, I’ve been on the phone with CEOs, just trying to get a handle on what’s actually giving them trouble, especially when it comes to go-to-market and working with their boards.

A couple of things keep coming up.

The first one keeps coming back in different words. One CEO summed it up cleanly. “Everybody’s interpretation of the value proposition is slightly different, because they’re not familiar with the domain. People struggle with that. That has been a bit the biggest go-to-market challenge from my point of view.”

The challenge is real. Board members come from a range of backgrounds, and none of them are deeply involved in the company’s day-to-day operations. So when the CEO walks them through the value prop and the GTM narrative, each one lands on a slightly different version. One hears the product story. One hears the buyer’s story. One hears something else again. Getting every board member to share the same understanding of what the company actually does and why it wins is one of the hardest parts of the CEO’s job when none of them are domain experts. It gets harder every quarter because the narrative itself is moving with the market, and the gap between what the CEO sees and what the board can hold in their heads keeps widening.

The second one is the playbook problem. Another CEO described it almost word-for-word. “The guidance I had from the CRO and from the board was, OK, we’ve now got to implement the machine. Create the top of funnel, stuff happens, you do deals.” Then he said, “It was quite a naive expectation that you could just follow a playbook and stuff starts to happen, especially right now with AI.”

The real challenge is pretty consistent: most board members have spent years working with models that used to work, and now the ground has shifted under them. Getting that across is harder than it sounds.

It’s not that the board is the bad guy here. They’re just working from what they know. But when there’s a mismatch, it’s the CEO who pays for it.

So if you’re an investor, chair, or portfolio manager on a board, this is really for you.

How most boards and CEOs are handling it today

Most boards push the old playbook (to varying degrees). Pipeline coverage. Top of funnel. Conversion rates. Did we hire the reps? Are we on plan?

In most cases, the CEO doesn’t have a choice. The board is pushing the “build the machine” narrative hard, and that’s the plan the CEO ends up executing against, even when they can see it isn’t fitting the market. Pushing back costs political capital they don’t have to spend, so they go along with it. They hire the reps, build the top of the funnel, and run the playbook the board signed off on, while privately knowing it isn’t the motion the company actually needs.

What it needs is a different kind of motion. Less execution against a fixed plan, more continuous adjustment to a buyer whose understanding of the category is still forming. The narrative has to be rewritten on a rolling basis, not signed off once a year. The team has to organize around the buyer’s situation rather than the funnel stage. Feedback from real conversations has to get back into the GTM motion in weeks, not quarters. And the people running it need to make judgment calls about what to test and kill, not follow a procedure. That’s what a GTM motion built for an AI market actually looks like, and it doesn’t fit neatly into the playbook the board is asking the CEO to execute.

Board members generally attend a bunch of boards and don’t have deep industry knowledge. This makes it a real challenge to understand nuances. This is one of the reasons they default to simplified framing. The more frequent updates are a great idea, but boards will need that translated to (i) Risk, (ii) Opportunity, and (iii) how it affects the assumptions in the business plan and strategy.

One CEO characterized the board’s involvement as administrative overhead, stating, “You provide what’s required and receive no value in return.”

Why doesn’t it work

The board’s advice is often based on assumptions the market has already moved past.

In an AI world, buyers are still figuring out what they’re even buying (i.e., we’re not buying a product, we’re buying the ability to get work done, not use tools but have actions done for you, in a collaborative way) and what problem they’re trying to solve. That changes so fast. For example, one company selling AI-powered customer support saw its buyers shift in a single quarter from wanting a self-service chatbot to seeking full conversational automation, and finally to demanding integrations with human agents and CRM, which nobody had even raised before. The buyers themselves often didn’t know what they would value next, and the sales team had to keep rewriting not just the pitch but also what the product actually solved. The company’s positioning has to move with it. The value prop isn’t something you set and forget. It’s a running conversation between a buyer whose problem keeps shifting and a company doing its best to keep up.

The old playbook assumes the buyer, the message, and the path to a decision are all stable. But they’re not. If the board is still anchored to that model, they’re giving advice to a business that no longer exists.

A specific example boards probably don’t know about: what’s happening to marketing right now.

Think about the last time you wanted to understand a software category. You didn’t download a whitepaper. You didn’t fill out a contact form. You asked an AI and had your answer in 30 seconds.

That’s the machine B2B marketing has been built on for a decade, quietly breaking.

The entire MQL model, gated content, lead nurture sequences, all of it assumed buyers needed you to give them information. They don’t anymore. AI has become the top of their funnel. Not your blog. Not your ads. Not your SDR sequence.

What replaces it is harder to measure. You create content good enough to get referenced by AI systems, and build enough trust that people eventually arrive at your site already convinced. You don’t capture them. You just have to be worth showing up for.

Here’s the question boards should be asking their CMO: Are you brave enough to accept that marketing is no longer about your attribution model, it’s about how your buyer actually buys? How do we respond to this new world?

Because right now, most marketing teams are still optimizing for numbers that are becoming less meaningful. The company wants to track and gate everything. The buyer has already moved on.

That tension only ends one way.

If it were up to me, here’s what I’d try instead.

First, get the board and CEO looking at the same thing the buyer is. Not just the same deck, but the same understanding of how the buyer’s problem is changing, and what AI has done to their decision-making. Ask the CEO to walk the board through what’s shifted in the last quarter, and what the company changed because of it. Like one CEO told me, the real challenge is just getting across that things are different now, and you have to approach it differently. If everyone’s working from that picture, the rest of the conversation actually matters.

Shorten the feedback loop on what buyers are actually saying. Pipeline data is always behind. Buyer reactions aren’t. Make it normal for the CEO to bring in what’s landing, what isn’t, and what they’re having to rewrite. One way to do this: set up a regular, dedicated ‘buyer insights’ session, where the CEO shares the most recent buyer feedback, surprising learnings, and any shifts in how the message is resonating. This gives the board a built-in rhythm to hear what’s actually happening in the market and lets the CEO highlight changes or challenges before they become bigger issues.

And the reality is board members generally attend a bunch of boards and don’t have deep industry knowledge. This makes it a real challenge to understand nuances. This is one of the reasons they default to simplified framing. Boards will need frequent comms that translate to (i) Risk, (ii) Opportunity, (iii) how it affects the assumptions in the business plan and strategy.

Action, action, action

Set aside time in every board meeting for the CEO to walk through how the buyer’s problems have changed, how AI is affecting decisions, and how the value prop has shifted. It’s the best way for the board to see what’s actually happening in the market.

Between meetings, ask the CEO to share at least one recent insight about their buyer that actually changed the company’s messaging. Ideally, have these updates delivered through a consistent channel. Whichever is already part of the board’s routine and easiest for everyone to reference later. Setting that expectation keeps the flow of information reliable and makes it easy for board members to keep pace. If a couple of months go by without a real update, make that the main topic next time.

Track how the story is changing, not just the pipeline. The pipeline tells you what already happened. The value prop tells you if the company is still keeping up with the market. Both matter. Most boards only look at the first one.

Quarterly updates just aren’t fast enough for a market that moves this quickly. Monthly reviews of the buyer and the story, alongside the formal board meeting, are much closer to reality.

Let’s be realistic

None of this is easy. The way most boards operate was built for a slower market. Asking people to change habits that have worked for them for years is a big ask. The easiest way to start is to pick one board meeting in the next quarter and dedicate ten minutes to discussing a recent buyer insight or a shift in the value proposition. You don’t have to overhaul everything at once. Just building this new habit into the routine is often enough to kick off the bigger change.

But most CEOs have already figured this out. They’re running the company for the new market, and the board for the old one. They’re tired. Most won’t say it out loud, because it’s just not worth the trouble.

The boards that get this right won’t look all that different from the outside. They’ll just be the ones the CEO actually wants in the room, asking questions that help move things forward instead of making them explain themselves again.

That’s the part worth fixing.

BOARD MEMO: How to find out if your GTM is getting value (internally) from AI