technicaljedi

What Good Outside Counsel Actually Looks Like

Thu, 04 Jun 2026 18:00:08 GMT

A CEO I worked with years ago had a binder full of advice. Slide decks from two different firms, a strategic review commissioned the year before, and a thick memo from a lawyer about a decision that had already been made. None of it told him anything he didn't already know. Most of it arrived after the moment it might have mattered. He kept the binder because getting rid of it felt like admitting he'd wasted the money.

I've thought about that binder a lot.

Most executives I know have a version of it. Advice that was technically thorough, professionally assembled, and essentially useless. The consultant had the credentials. The engagement was properly scoped. The report answered the question it was hired to answer. And yet, at the moment of actual decision, the person making it was still alone.

The structural problem nobody names

Here's why this happens so reliably: most advisory engagements are designed around what gets billed and delivered, not around what the client actually needs. When you scope an engagement around a report or a set of recommendations, you create a very specific incentive structure. The advisor's job becomes protecting the engagement, staying in scope, qualifying every conclusion to avoid liability, presenting a range of options rather than a point of view.

That's not dishonesty. It's just the logic of the arrangement. The problem is that logic produces advice optimized for defensibility, not usefulness.

Genuine counsel, the kind that changes how a decision gets made doesn't usually arrive on time for a scheduled deliverable. It arrives in a fifteen-minute conversation before a board meeting. It comes up in a call you weren't planning to have. It happens when someone who knows your situation well enough to skip the setup says, plainly, "I wouldn't do that, and here's why."

That kind of conversation is almost structurally impossible when the relationship is defined by scope and invoices.

What it actually requires

I've been on both sides of this. I've sat across the table from advisors who gave me everything I asked for and nothing I needed. I've also been the person someone called at 9 p.m. before a hard conversation the next morning. Both experiences taught me something about what makes the difference.

Context is everything and it can't be briefed. An advisor who has spent real time learning your business, your board, your competitive pressures, and your own blind spots doesn't need fifteen slides before they can be useful to you. They already know where the risk is. That context compounds over time. Six months in, they're dramatically more valuable than they were on day one.

Honesty is more rare than it sounds. Most people who are paid for their thinking are also, quietly, in the business of being liked. That's human. It's also why so much advice drifts toward what the person asking wants to hear, or stops just short of the uncomfortable thing. Good counsel requires someone willing to say the thing that might make you defensive, calmly, directly, without softening it into ambiguity.

Availability matters in a way people underestimate. The right advice given three days after the decision is made is not advice. It's a retrospective. If someone can only reach you on a standing call, you are not actually serving as their counsel. You're serving as a scheduled resource.

What compounds

The best advisory relationships I've seen look less like a service and more like a long conversation that never quite ends. The executive develops enough trust to raise the real version of the problem, not the presentable one. The advisor develops enough context to respond to that version usefully, without needing to be caught up.

That dynamic takes time to build and is easy to disrupt, by treating every conversation like a billable interaction, by scope creep anxiety, by the advisor hedging to protect themselves rather than helping the client see clearly.

When it works, it's one of the most leveraged relationships a leader can have. Someone outside your organization, without a political stake in the outcome, who knows enough to ask the question you haven't let yourself ask out loud yet.

That binder of advice my CEO had? None of it asked him the hard question. That's what he actually needed and what was never in scope.

The AI Investments That Don't Compound

Thu, 07 May 2026 18:00:03 GMT

Two years in, the pattern is becoming visible. Businesses that adopted AI tools in 2022 and 2023 are splitting into two groups, and the dividing line has almost nothing to do with the technology they chose.

One group has real leverage, decisions that are faster, better-informed, and consistently made at the right level of the organization. The other group has subscriptions. Sometimes expensive ones. And a quiet, lingering question about whether any of it was worth it.

I work with businesses on ERP integration and AI deployment in real commercial operations. The pattern I keep seeing isn't about platform choice or budget or technical readiness. It's about where the starting point was. When you start with a tool, the default path into AI adoption usually looks like a vendor demo, a compelling use case from a competitor, or pressure from the board to "do something with AI." The procurement happens. The tool gets deployed. Someone is assigned to champion it. And then, six months later, a small fraction of the team uses it regularly, the ROI calculation is murky, and nobody quite wants to say the quiet part out loud.

Starting with a tool is the default because tools are concrete. You can show them in a demo. You can get a quote. You can check a box. The problem is that tools are answers, and you haven't asked a question yet.

When you lead with a tool, the implicit question becomes: "How do we use this?" That question will always find an answer, because people are resourceful and no one wants to admit a purchase was wasted. So the tool gets pointed at whatever work is most visible. Usually automating tasks, reports, summaries, data entry. And sometimes that's fine.

But tasks that are visible are not the same as tasks that are valuable. And automating a process that's inefficient or unnecessary doesn't fix it. It just runs it faster. I've seen businesses automate workflows that existed only because their ERP was configured wrong six years ago. The automation didn't solve the problem. It cemented it.

When you start with a question, the businesses getting real compounding value from AI started somewhere different. Not with "what can this tool do" but with "where does a decision get made in this business, and would better information change that decision?"

Most organizations don't have a clear map of where decisions actually happen, not in org charts, but in practice. Who decides which leads get followed up with urgency? Who decides when to adjust pricing? Who decides whether a job is worth quoting? These are high-impact moments that often run on incomplete information, intuition, and whatever was in the last email thread.

When AI is applied to those moments not to replace the decision, but to improve the information available to the person making it, the value compounds. A better-qualified lead doesn't just improve one deal. It changes how the sales team allocates its time. Better job costing data doesn't just help one quote. It recalibrates the pricing model. The effect isn't linear.

I worked with two businesses in commercial operations, both of which implemented AI-assisted quoting in roughly the same period. One automated the quoting process itself. Faster turnaround, consistent formatting, reduced admin time. The other stepped back and asked what actually determined whether a quote was worth writing in the first place. They used AI to improve lead qualification, analyzing inquiry signals, job characteristics, and historical win rates before a quote ever got produced.

Eighteen months later, the first business had a faster quoting process. The second had improved their quote-to-close rate by restructuring where they focused attention. The first invested in speed. The second invested in judgment. Only one of those compounds.

The question worth asking before any AI investment isn't "what will this automate." It's: if the quality of this decision improved by thirty percent, what would change downstream in the business?

If you can answer that clearly, you probably have the right starting point. If you can't, the tool can wait.

Why Your Market Puts You in the Wrong Box

Thu, 09 Apr 2026 20:20:25 GMT

At some point in the last few years, you probably updated something. Maybe it was the website. Maybe a new deck, a rebrand, a tightened value proposition your agency was proud of. And still, when you show up in a sales conversation, you can feel it. The slight misread, the wrong comparison, the prospect who sees you as a vendor when you're trying to be a partner. Something isn't landing.

The instinct is to keep adjusting the messaging. Run another workshop. Try a different angle. But most positioning problems aren't communication problems. They're decision problems. And until you make the actual decision, the words won't fix it.

Here's what the market is doing whether you like it or not: it's filing you somewhere. Human cognition doesn't tolerate ambiguity well, and buyers in particular need a mental drawer to put you in. If you don't hand them a clear one, they'll use the nearest available option usually defined by your lowest-common-denominator competitor, the broadest version of your category, or the first association you triggered when you first showed up.

Once you're filed, you're filed. Getting re-categorized is an uphill project.

The businesses that own a sharp position didn't get there by writing better headlines. They got there by making a hard internal commitment about what they were and just as importantly, what they were willing to stop claiming to be.

Most businesses resist this. The reluctance is understandable. When you've built something, narrowing the frame feels like closing doors. If you say you focus on mid-market industrial distributors, does that mean you're turning away the manufacturing client who wants to call? If you anchor on transformation rather than implementation, does that mean you lose the projects that are, honestly, a little more transactional?

These feel like revenue questions. They're actually positioning questions. And the unwillingness to answer them is exactly what produces vague positioning — the kind that puts you in the cheapest, most generic version of your category, competing on capability claims that every other firm in your space is also making.

"Full-service." "Strategic partner." "End-to-end solutions." These phrases cost you nothing to write and earn you nothing in the market. They are the linguistic equivalent of standing in a crowd with your hand half-raised.

I see this pattern most often in industrial and commercial B2B businesses, heavy equipment, building products, specialty distribution, technical services. These are markets where relationships run long, where "we do everything" feels like a competitive advantage because flexibility has real value at the account level.

The problem is that flexibility at the account level and clarity at the market level are different things. The market doesn't buy from you because you're adaptable. It considers you because it knows what you're for. Once you're in a conversation, bring everything you have. But you have to earn the conversation first, and vague positioning makes that harder than it needs to be.

In those markets especially, the cost of being uncategorized is high. The referral doesn't happen because no one has a clear sentence for what you do. The RFP doesn't include you because the shortlist was built around a category and you didn't own one. The pricing negotiation starts at the wrong number because the buyer has mentally sorted you into a commodity tier before the first meeting.

Clarity is not a creative problem. It's a leadership decision.

Someone in your organization has to decide what the business actually is, commit to it visibly, and then hold the line when the drift starts. Because drift is the default. Sales wants to broaden the aperture. The team wants to preserve optionality. The board wants the TAM to look bigger. All of those pressures push toward vagueness.

What changes when a business genuinely commits to a position is specific and observable. Sales conversations get shorter because the prospect already knows why they're there. Pricing power improves because the comparison set shrinks. Referrals become more precise. The work itself tends to get better because you're repeatedly solving the same class of problem and getting sharper at it.

None of that requires better marketing. It requires a decision.

The uncomfortable version of this is worth saying plainly: if the market has you in the wrong box, you probably gave them no better option. That's not a knock — it's a starting point. The box you're in right now is the result of every claim you've made, every client you've taken, every time you softened the positioning to avoid closing a door.

You can choose a different box. But you have to be willing to name it, claim it, and mean it.