Category Archives: Boards

On the Socially Acceptable Use of AI in Business

There’s a question I’ve been mulling for a while now, and I think it’s time to write it down: when is it okay to use generative AI in a given business context, and when does it cross a line? I’ll focus on two specific areas I know well — board work and strategic analysis — but I think the principles generalize.

Let me start with what I think is the easy part. Using AI to draft a meeting agenda? Fine. Using it to generate a board deck? Also fine, though you’ll probably go to manual edits after the first or second draft. Using it to produce a document summary? Fine [1]. These are tasks where AI is essentially doing the grunt work of organizing information you already possess, and where the human judgment — yours — is the thing that actually matters.

Using AI to produce final documents? That’s dicier today — ask anyone in legal — but I think there’s a simple rule that applies to all of these examples.

That rule? Use AI to do whatever you want, but you own the output. Not the AI. You. If it’s wrong, that’s on you. If it misses something important, that’s on you. The moment you present something to a meeting, a customer, or a board, you are vouching for it. Saying “well, AI generated that part” is not a defense. It’s an abdication of duty.

The “Ad Hominem” Problem

Here’s something that bothers me about the discourse around AI-generated content: people hear, or even suspect [2], that AI wrote something and it’s immediately dismissed — not because of anything wrong with the content, but because of how it was produced. That’s a logical fallacy. Specifically, it’s a variant of ad hominem: attacking the source rather than the argument [3].

I frequently need to remind people of this. Judge what was said, not who — or what — said it [4] [5]. If the analysis is sound, the framing is useful, and the questions raised are the right ones, then the mechanism of production is largely beside the point. The quality of the thinking is what matters and what should be challenged.

That said — and this is important — the inverse is also true. Producing AI-generated content and presenting it as your own thinking is not okay. The problem isn’t that AI helped. The problem is the pretense that you did the thinking when you didn’t. Ownership means you’ve read it, challenged it, corrected it where it was wrong, and can defend it. If you can’t do that, you haven’t done your job.

AI as Calculator

I’ve always thought the right analogy for AI is the calculator. A wildly more powerful calculator, obviously, but a calculator nonetheless.

When calculators became ubiquitous, people lamented the loss of slide rule proficiency. And yes, something was lost. But the point of mathematics was never arithmetic. It was reasoning. If the calculator handled the arithmetic error-free, you could spend more time on the part that actually matters. The same logic applies here: there’s a lot more to argument and strategy than copywriting or slide formatting. If AI can handle the scaffolding, you should be able to spend more time on the substance.

The complication — and it’s a real one — is that AI can start to approximate thinking in ways a calculator never could. A calculator doesn’t write your memo. It doesn’t suggest your strategy. It doesn’t synthesize twenty pages of board material into five crisp questions. AI does all of that. And that creates a temptation toward laziness that calculators simply didn’t. The laziness is the problem, not the temptation toward it.

There’s also research starting to emerge suggesting that relying too heavily on AI can actually impair your own reasoning. You offload the synthesis, and you stop synthesizing. You offload the framing, and you stop framing. The cognitive muscle atrophies.

I was not surprised when I read reports that people with long streaks in Duolingo couldn’t speak well in practice. In my view, as a half-decent French speaker: if it doesn’t feel like work, you’re probably not learning [6]. Corrolary: if it doesn’t feel like work, you’re definitely not working.

How I Use AI in Board Work

Here’s what I often do with AI today. I sit on several boards, and I’ll sometimes load a board deck into a generative AI tool before the meeting. I ask for a summary. Then I’ll ask how it thinks the company is doing. I’ll then ask for the top 5 questions to ask in the meeting. Then, I’ll go read the deck with an eye toward what’s been extracted [7].

And then I’ll go back and challenge the AI. I think issue three is more important than issue one. I think it missed issue seven totally. I think issue two isn’t an issue; the company’s fixed it already. Often, I’ll bring competition into the picture because (in my humble opinion) most boards don’t spend enough time thinking about competition [8].

And here’s the question I’ve been wrestling with: should I be transparent about using AI to help generate those issues (or questions) when I bring it to a board meeting?

My instinct is yes. If I want to send the CEO a list of top five issues facing the company before the meeting, I have two choices:

  • I can pretend I wrote it myself, unassisted. Complete with typos and hyphens instead of em-dashes.
  • I can say, “here’s what I generated with Claude after iterating on your board deck” and copy/paste the final transcript.

Now, I know what management can think: “Well, we could have asked Claude, too” [9]. And I’m okay with that. My response would be: “Well, then, why didn’t you?” I just want the best topics list.

To me, the question isn’t where the list came from. The question is whether it’s the right list. That’s the only question that matters. Boards have very limited time together. We should think hard and use all available tools to ensure that we’re spending that time on the right issues.

The point isn’t the slides or the questions list or the agenda or the summary. The point is the conversation. To maximize value, we need to be having the right conversation. No talking about things easy to talk about. Not going through the motions. Not death marches through templates, much as I love both templates and death marches.

This takes me back to calculators. I can check the math on your board slides using pencil and paper. Or I can use a calculator. Or I can upload your table and ask Claude to check the math. We can take a test with our calculators secretly on our laps or with them in plain sight on our desks.

I vote for the second option. Use all available tools. Don’t use them clandestinely. Use them out in the open. But don’t abdicate to them. Own the output. This isn’t Claude’s list of our top five challenges. It’s my list, built using Claude [10]. Better yet, it’s my list, period. (But I’m not going to hide that I used Claude to help build it much as I wouldn’t hide that I used a computer and a keyboard.)

That’s where I am. I’m curious where you are. Is there a line you’ve drawn in your own work? Do you think transparency about AI assistance is a norm we should be enforcing, or are we creating a two-tiered standard we’d never apply to other tools? Let me know in the comments.

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Notes

[1] Just as long as you also read it or are prepared to say, “I didn’t read it, I only read a summary.” FWIW, I find it useful to generate a summary, read it, and then read the document. And sometimes, then go back to the summary. The summary ends up serving as a reading guide.

[2] Thanks to tells like the dreaded em-dash.

[3] I had to air quote ad hominem because — thanks to my high school Latin teacher, Mr. Maddaloni — I know that ad hominem means literally “toward the man.” There is thus not only gendered language (heck, it was nearly 3,000 years ago) but considerable irony in speaking of ad hominem attacks on a machine. Ad machina, anyone?

[4] By the way, this is the exact opposite of most social media behavior.

[5] This isn’t just good intellectual hygiene — it’s a reliable way to reduce or eliminate bias. When you evaluate an argument on its merits rather than its source, you sidestep a whole class of distortions: the tendency to over-credit ideas from high-status people, to dismiss ideas from unexpected sources, or to reject a perfectly sound analysis because you don’t like the messenger. It’s a discipline worth practicing whether the source is a junior analyst, a competitor, or a language model. The argument either holds up or it doesn’t. That’s the only test that matters.

[6] This is a critique on gamification, but also is highly related to the topic of customer value metrics, about which I’ve written with my Balderton EIR colleague Dan Teodosiu.

[7] By the way, the wordier the board deck, the more this process helps.

[8] This itself could be a long discussion but remember three things: my first job in marketing was competitive analyst; I believe strategy is either “the plan to win” (Burgelman) or “the way to overcome our biggest challenge” (Rumelt), and ergo it cannot be done without looking at the market. North Stars are great, but they don’t tell you about the army you’re going to face when you hit latitude 55 degrees 45 minutes.

[9] And this is probably the kindest thought. Others might include:

  • Perfect — now the monkeys have flamethrowers
  • Fantastic — it’s like giving toddlers espresso and a whiteboard
  • Great — now the VCs can skip even faster to the wrong conclusion
  • Terrific — now it’s gut feel with citations
  • Right — so now we’re pattern matching with turbo-autocomplete

(And those are manual em-dashes.)

[10] I assume that we are not all going to have the same AI conversation or all use the same tools. The way I push Claude is going to be different from the way another person does.

The Ten Most-Read Kellblog Posts in 2025

I did this analysis last year and it became a popular post, so I figured I’d do the same retrospective today. Following are the ten most-read Kellblog posts in 2025, regardless of the year in which they were written — and it includes some golden oldies.

  1. What it really means to be a manager, director, VP (2015). Now at ten years old, this post is a perennial favorite. I wrote it because I got tired of answering the question and something about my answer clearly struck a note with a lot of people. (Hint: the answer’s not in your job leveling system.)
  2. How to navigate the pipeline crisis (2025). In this post I wrote about what I saw as a general pipeline crisis in the industry, shared some interesting posts on it, and then tried to put myself back in the CMO chair and answer: what would I do about it?
  3. The one key to dealing with senior executives: answer the question! (2012). If the manager vs. director post (above) gets the most traffic, this post gets the most in-person mentions. Think: “Dave, I forwarded your ATFQ post about a dozen times this year.” This issue bothered me 13 years ago when I wrote the post and evidently non-answered questions are still bothering people today. If someone, particularly a customer or an executive, asks you a question: answer it.
  4. Kellblog predictions for 2025 (2025). I scored these an 8 out of 10. Go here to read my predictions for 2026, the 12th annual post in this series. These posts are more industry commentary and analysis than simply a list of things I think are going to happen. And they require Herculean effort. This year’s post was 7,644 words with 166 links and took 65 hours to write.
  5. Your ICP starts as an aspiration and ends as a regression (2025). I love the pithy title of this one. This post discusses the evolution of your ideal customer profile (ICP) which starts out as a wink in the founder’s eye and should, over time, end up the result of a regression analysis. That is, you start out by deciding who you want to focus on and then, over time and as a function of your definition of “success,” the data should tell you.
  6. De-mystifying the growth-adjusted enterprise value to revenue multiple: introducing the ERG ratio (2024). I first heard of the PEG ratio in Peter Lynch’s classic, One Up on Wall Street. This post takes the same idea — growth adjusting — and applies it to price/sales as opposed to price/earnings. Much as I love the metric, I was frankly surprised to see this one up here.
  7. The SaaS Rule of 40 (2017). Another classic, from eight years back. See this year’s predictions to understand why I believe the Rule of 40 might well become the Rule of 60 in 2026.
  8. A CEO’s high-level guide to GTM troubleshooting (2025). An integration and repackaging of a lot of my advice specifically written for the CEO and to help them troubleshoot their go-to-market (GTM) issues. I was happy to see this one up here.
  9. The pipeline progression chart: why I like it better than tracking rolling-four-quarter pipeline (2022). Give the CRO rolling-four-quarter sales targets and I’ll be in favor of tracking rolling-four-quarter pipeline. Meantime, we need to track it by quarter and this chart shows you how. Don’t even get me started on people who want to track annual pipeline.
  10. Six tips on presenting to the board of directors (2025). A post I wrote to help executive staff make a good impression on the board by losing any prior board PTSD, making a deck from scratch (not recycling slides), cutting to the chase, taking certain things offline, and of course ATFQ.

Technically, my Best of Kellogg post also made the list, so if you’ve not checked that out lately, perhaps you should. I’ve recently revised it as I do about once a year.

I was happy to see that five of the ten top posts were from 2025, which I think hits the right balance of healthy re-use of the classics along with some endorsement of my new material. Thanks for reading.

The Startup Board’s Hippocratic Oath

The Hippocratic Oath is a well known oath of ethics taken by physicians. It requires them to swear, among other things, to do no harm in dealing with patients. While chatting with a VC the other day, it occurred to me that we should have a similar concept for startup boards.

Unfortunately, I think “do no harm” actually sets too high a bar.

To help startups succeed, boards need to challenge leadership teams, ask hard questions, and get them to consider new ideas and approaches. While I think boards should refrain from giving directive feedback, there is always the chance that a hard question leads the company down a path that ultimately proves unproductive. For example, if a board member asks if a company to consider a PLG motion for a new product, that could lead to the company launching a new sales motion that ultimately fails.

This example, by the way, shows both why boards should not give directive feedback (i.e., “do a PLG motion”) and why founders should not listen to them when they do. Think: yes, we’ll consider that, but only try it if we think it’s a good idea. Throwing a bone to board members by agreeing to try ideas you don’t believe in is a losing strategy. If they fail, you are more likely to get scorn for poor execution than credit for the openness in having tried. When results are the only thing that matter, only place your bets on things you think will deliver results. (And yes, the possibility that you threw good execution at a bad idea seems conveniently never to be in consideration.)

If “do no harm” sets too high a bar, then what oath might we use? After talking to my friend, I think I found a great alternative: do no demotivation. “I don’t want executive teams leaving board meetings feeling demotivated,” he said. And he was absolutely correct.

How do we want people to feel at the end of a board meeting?

  • We want the board to feel like they attended a well-run meeting, had a chance to help the company, and understand the plan to address current challenges going forward
  • We want the management team to feel like the board is knowledgeable, helpful, and supportive
  • And we want the management team to feel energized to go execute the plan

That’s it. If you get those three things, you had a successful board meeting. And demotivation is nowhere on that list. Demotivation doesn’t help anyone.

  • It doesn’t improve the odds of executing the plan successfully
  • It definitionally doesn’t make anyone feel good
  • It does make the e-staff start to question the CEO and each other
  • It does make people wonder why they’re grinding so hard
  • It does make the team feel unappreciated and potentially vulnerable

So I’d propose Do No Demotivation as the Hippocratic Oath for startup boards.

I’ll finish this post by listing some common ways that boards demotivate executive teams (and feel free to put more examples of your own in the comments):

  • Expressing surprise over things they should have known.
  • Asking trap questions: “do you think our sales productivity is substandard or very substandard?”
  • Placing blame: “clearly, since our CAC payback is so long, we have an inefficient sales organization.” (Maybe we do. Or maybe we have a hard-to-sell product. Or weak gross margins. Or something else. The high CPP is a fact. The reason for it is not always a bad sales team.)
  • Cherry-picking: taking top decile benchmarks, or public comps, or even just top quartile numbers but across 4 different metrics. It’s like comparing your child to the best mathematician, athlete, musician, and writer in the school. (It’s quite rare when one person is all those things.) Or, my favorite: benchmarking without regard for situation. Yes, our CAC ratio is high, but 75% of our deals are dogfights against a price-slashing competitor. And yes, I know what “sell value” means, thanks.
  • Expressing anger in pretty much any form. While I’ve seen some howlers, fights in board meetings are not OK. They demotivate everyone. And they take focus off the top busness priorities.
  • Ratholing, failing to take things to an offline meeting or working group. OK, I do this one from time to time. (“But I promise it will be quick.”)
  • Making easy things hard. When in doubt, if a topic is not strategic, just do things the standard way at the good-enough level.
  • Expressing negative or hopeless sentiments: “at this course and speed, I’m not sure we’re creating any value.” As opposed to: “we need a new plan that creates value and that means we need to find a way to accelerate growth.”

So before you attend your next board meeting remind yourself to do no demotivation. It’s the new Hippocratic Oath of startup boards.

Three Ways To Get Fired as CEO

While I could write the equivalent of 50 Ways to Leave Your Lover when it comes to variations on how to get fired as CEO, the purpose of this post is simply to discuss three things CEOs can say to their boards that will perk their ears and get them to start asking questions that could lead to the CEO’s termination.

Here are those three things:

  • I’m getting tired of running the company.”
  • I’m running out of ideas for how to fix our core problems.”
  • I think we need to sell the company.” [1]

First, let’s note that it is much harder, sometimes actually impossible, for a founder/CEO to get fired than a hired (aka, “professional”) CEO. The former have a powerful combination of moral authority, share ownership, and/or contractual protections. The latter — even if they joined very early and built much of the company themselves — will never be seen as founders, but simply employees who, in the end, are replaceable much as anyone else.

While it’d be stretch to call hired CEOs “goldfish” — as one of my old CFOs used to refer to SDRs [2] — in the end, you’re either a founder or you’re not. So this post is largely for hired CEOs, but it should nevertheless be of interest to founders as well.

While it’s probably somewhat self-evident, what’s so scary about the three above statements?

  • They each say the CEO is effectively giving up on solving the company’s challenges
  • They are not easily fixable by the board — a stock grant, a pat on the back, or a bonus program isn’t likely to fix anything
  • To the extent you define the CEO’s job as “to get what matters right,” they each signal that the CEO is no longer interested in doing it

And scariest of all, each statement is a bell that is impossible to unring. Think: Oh, just kidding, I have tons of ideas. Or, oh, I was just messing around, I don’t think we should sell the company. It was just a modest proposal, in the Jonathan Swift sense. Sure.

It’s like saying to your spouse, “hey honey, I think we should start dating other people.” It’s very difficult to roll that back.

This means the CEOs should think very carefully before making statements like these. Because once they’re said, they may be stuck somewhere in the board’s mind forever:

  • We keep missing quarters because Mary’s tired and not pushing the company.
  • We’re only shooting for moderate growth because Bob’s out of ideas for how to grow more quickly.
  • James isn’t investing for growth because he wants to sell soon and is trying to juice up profit.

Why? Because the CEO told us so. If I were a bell, I’d go ding, dong, ding, dong, ding.

Now, it’s certainly possible to try and walk these statements back: “oh, I was just tired that day because I had some personal stuff going on and I was sick.” But they’ll always be there in the back of the board’s mind. Think: Maybe Joe said that because Joe meant it.

So the best thing to do is never say these things in the first place. Not unless you’re very sure how they’ll land and ideally have socialized them 1-1 in advance with key board members. Or, if you decide to say them anyway, at least understand the potential downstream effects. Otherwise, you may find that a simple, off-the-cuff comment may haunt you for some time.

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Notes

[1] The notable exception here is a PE-backed firm where the company has achieved its target financial profile and ergo hopefully its target valuation, and it really is time to sell. In VC-backed firms, where the general goal (and belief that underlies the VC’s investment thesis) is to “shoot the moon,” saying you want to sell can be seen as betraying the mission — especially if the company is performing well — and/or if the VCs still believe in the company’s bright future. Saying you want to sell before there is consensus that hope is dead can be seen as a premature admission of defeat.

[2] On the theory that they often perish, and if you find one floating in the bowl, you just get a new one.

Change Management and Selling Hope Along The Way

Let’s say you’re a CEO leading your startup’s migration from mid-market to enterprise. To do that, you’ve hopefully already done the following:

  • Analyzed existing success in enterprise accounts. (Most people don’t start purely from scratch, but instead have picked up a few “accidental” customers that they hope to replicate.)
  • Hired a team to pursue enterprise, ideally with dedicated AE, SCs, SDRs and even more ideally with a dedicated CSM and marketer. Concretely, that initial team might look like 1 sales manager, 4 AEs, 2 SCs, 3 SDRs, 1 CSM, and 1 field marketer. A focused team of dedicated resources is an infinitely better approach to opening a new market segment than making it everyone’s pastime.
  • Done market research to understand the competitors you’ll encounter and the buyers to whom you’ll be selling. You’ve then made an initial strategy for beating those competitors and built messaging that maps to those buyers and their business priorities.
  • Identified product gaps. Your product team has done a study to identify missing product features that customers in the new segment will demand. You’ve made a plan that combines workarounds and the product roadmap to sell successfully despite these gaps while you work to close them. (Beware that product gaps, often involving non-functional requirements, doom more new market migration initiatives than any other.)
  • Sold the initiative to both the board and the company as a valid and important priority. This will get you buy-in at both the board and team level, hopefully evoking real commitment to the new and difficult undertaking. As part of this, you may well have set initial end-state goals — e.g., getting 25% of new ARR from enterprise in six quarters, increasing your average sales price (ASP) by 50% relative to mid-market, and increasing product penetration per account from 1.5 to 3.0 products.

That’s awesome. You’re doing it by the book. So what did you forget to do? Particularly when getting to the initial end-state might take six quarters and another year or two beyond that to look at renewal and expansion rates?

What did you forget? To sell hope along the way.

I don’t mean selling hope in the metaphorical Charles Revson way. I mean selling hope in a literal way to the team and the board. Twelve to eighteen months is too long for people to wait for results. But if it takes 3 months to build the team, 3 months to ramp them, and sales cycles are 9-12 months, then your earliest possible results are 15-18 months from when you hit the “go” button with the board. Coincidentally, that approximates the MTBF for CMOs.

How do you sell hope along the way?

  • You lay out expectations, up front. You describe how you expect things to progress over time (e.g., enterprise team staffed up, first enterprise marketing event, hit enterprise pipeline of $3M, first closed new customer). And like any expectations, you set them carefully and remind people of them often.
  • You tell stories along the way. This is the part most people don’t forget. Hey, 125 people showed up at the enterprise event. Hey, we had a great meeting at BigCo. Hey, an analyst positioned us in an enterprise report. Hey, we hosted a great enterprise dinner in Philly. This is good, but the stories start to ring hollow pretty quickly in the absence of up-front expectations setting and downstream data.
  • You use leading indicators. Sure, we all know the end-state indicators that we want. A big chunk of total ARR. Faster growth. Bigger deals. Higher win rates. Increased GRR and NRR. Those are real indicators — and they’re important — but they’re lagging and, in cases, badly. You need to find some leading indicators to track and measure along the way. For example, in the enterprise segment: pipeline size, pipeline coverage, average size of oppties, high- and mid-funnel conversion rates, number of customers. Note that when moving up market, some metrics are going to get worse (e.g., stage progression velocity) so you may as well track and set expectations for those as well.

The main point here is to not make the rookie mistake of screaming: “Mid-market is dead! Long live enterprise!” Thus setting impossible expectations for enterprise all while undermining your mid-market efforts. Instead, you should carefully think through how the enterprise initiative is going to unfold, lay that out both qualitatively and quantitatively with leading indicators, and then report back to the company and board with progress reports, war stories, and metrics.

You’ve already convinced people that the enterprise initiative is a good idea. Now you need to make and execute a plan to keep them excited along the way.