Okay, previously we covered many of the most common things you'd want to know about a board of directors at an organization, including the basics like what a board actually does. Next up, I put out a prompt on my various social media channels to solicit what questions people had about boards, to attempt to answer requests more directly.

Speed round: Board stuff!

(I have quoted people's questions verbatim but am not linking directly to the askers just for the sake of discretion):

How active are different board members, on average, and are there any patterns that can help a company choose a successful board member?

As mentioned in the previous post, this can vary a lot — some folks may be there in name only to lend prestige, others might be super-involved. A great way to evaluate board members is to judge their engagement in the problem space that the organization is trying to help solve — are they there organically, of their own will, already? If so, that's a great place to start.

what to look out for when you’re asked to be on [a board], what are the red flags

I'd start by asking why they want you to join the board, and get that answer independently from different members of the board, as well as leadership. Comparing those notes will tell you a _lot_ about whether it's a good opportunity. If they talk about the mission and how you help them achieve it, that's great. If they talk about what's broken on the board and how you're the fix for that... well.

What is the *main* purpose of a board, given a company and its size, market, etc?

I think a lot of that is covered in the previous post, but broadly, in for-profits it's about enabling growth over time, and in non-profits it's about ensuring sustainability while working on a particular problem.

How often did you come away more (rather than less) impressed with the executive team than you expected?

In the organizations I've worked with? Every single time I came away more impressed with the executive team. Every time. Tons of thought, tons of heart, tons of dedication to the work. Of course there were individual exceptions where someone was a jerk or incompetent or whatever, but overall people care a lot about putting their best work (or, even better, their team's best work) in front of the board, and that is the overwhelming impression that I take away.

How much should you worry when you ask about the policy on [thing] and they laugh nervously?

That is a moderate-to-large-sized yike. Sometimes they're laughing because they've talked about it ad-nauseum and are aware it's an issue and are working on it. Sometimes they're laughing because they're aware it's an issue and they've all been dancing around it.

What signs do you look for to join, and what are red flags? When do you leave? Would you join a board for an org that is far from your core expertise?

Basically, I look out for alignment on mission, belief in the team, and an opportunity for me both to bring in my skills of what I'm good at and also a chance for me to learn a lot. I wouldn't join an org that's widely out of my expertise unless they specifically asked me because they were looking to broaden out.

when, if ever, is there real disagreement among board members, and how does that get hashed out

It's rare, but it absolutely does happen. As I said, sometimes it's just about everyone agreeing on goals but disagreeing on paths to getting there; that's not usually _too_ hard to settle unless egos get in the way or something like that. If it's a firm disagreement on vision/intent, eventually it almost always leads to the party that disagrees with the founder/chair/CEO getting quietly moved off the board.

as a board vp of a tiny nonprofit, I’m curious about how the experience differs from for-profit boards of various sizes.

Biggest thing is the shift in focus on resourcing and fundraising. It takes a lot more effort proportionally to support a small organization, whereas a larger org will tend to have that function professionalized, so then more of the conversation can be about strategy and the like.

How were you able to identify private company board seat opportunities? Did you work w/a headhunter that specialized in board placements? Besides monetary compensation, were there other types of compensation, perks offered for your time?

I identified opportunities based on my passion for the work the company was doing, or my belief in the founders. In many cases, I was doing board-level advising for their company for a long time, even years, before I was asked to be on the board. As I said, my experience is atypical because much of my opportunity arose from my visibility, but I've definitely worked with great board colleagues who came in through headhunting firms. By far the most common scenario is people networking their way into consideration. In terms of compensation, I've gotten equity in some of the for-profit boards I've been on (that's really only been material once, in the startup world it's mostly just working because you think it's worthwhile, and hoping it turns into something) but in terms of perks, I haven't done a lot of the "they fly you to Hawaii for a board meeting" kind of stuff. It does happen, especially in publicly-traded companies.

How much of the documents they send you do you actually review, vs how much is just listening to management and rubber stamping their suggestions?

I read all of it, every time, with rare exceptions. And I usually try to have good questions or notes on what I took away from the pre-read. Obviously, sometimes being busy or only getting the material shortly before the meeting can affect that, but having been on the other side of preparing those materials, I take it pretty seriously. (My "make better documents advice is based very directly on that experience.) That being said, I've definitely seen times when folks in a board meeeting very obviously didn't do their homework, and I find it pretty frustrating. Fortunately none of the boards I work with now have that problem.

Is it really just all about fundraising? Or are their positions that do other stuff?

This can vary a lot. Sometimes in scrappy non-profit world, it's definitely a "let's put on a show and save the orphanage!" vibe, but even then there are board members who aren't focused on getting dollars in the door. For larger scale corporate efforts, there's a revenue conversation every time, but fundraising or seeking out capital is a structured process that will usually (ideally!) happen on a predictable schedule, instead of being a constant scramble.

what are the red flags when recruiting and interviewing potential board members? (Or more broadly, what are good/bad ways to identify and recruit new members?)

Huge red flag is when executive leadership seeks out their buddies to be board members right after they didn't get their way on a major decision, _doubly_ so if that major decision was about executive compensation. If you're in the position to evaluate board members yourself, judging their curiousity for the work your team is doing, and their fluency in your particular concerns, is really key. Resume honestly isn't highly-correlated to how good someone is at being a board member, in my experience. And often it's very hard to see from someone's LinkedIn (or whatever) whether they're genuinely engaged in unsexy concerns like governance and auditing.

Is there any such thing as being on a Board and NOT being expected to personally donate $1k+?

Assuming this is in the non-profit world, it's basically a "Nobody rides for free" kind of situation. The more-friendly name is a "give/get", where board members are either expected to personally give or get others to donate to a certain threshhold. Again, there can be some exceptions to this, but honestly it seems like a fair expectation to make of folks; if you don't have the funds yourself, then do the work to help raise them.

Why is there such a persistent silo-ing of stuff happening at the board level of non profits from the staff who are affected by their decisions and how can it be fixed

This question kind of haunted me. I could write another 5000 words on it, but it comes down to the structural stuff mentioned above — who shares what information with whom at what time. I honestly think it's _rarely_ because people are trying to hide board decisions from workers, though obviously there are some bad actors in executive roles who do see their workers as subordinates who don't deserve transparency. Far more often it's the combination of people being busy (especially in non-profits, where so many are overworked) and people playing the telephone game with passing information along. The net result is still awful, so I wish a lot more organizations would just have an open session with the board after board meetings where workers can talk directly to them, or let workers nominate an observer representative to the board to share information out. There's very little, especially in a non-profit, that needs to be kept fully private.

I've read arguments that the culture of boards of dir's have changed over decades to facilitate members who always support very high and even excessive (relative to performance and/or profits regardless of inputs) executive compensation. Do boards seem like yes crews regarding ex comp?" Yeah, the boards of big publicly-traded companies have become absurd rubber-stampers on exec compensation. Part of it is the inputs the compensation committees will use to determine comp, which involve things like "we took a survey of exec compensation from everyone in our industry cohort.

Shockingly, looking at a whole bunch of companies that also have overpaid CEOs will result in you overpaying your CEO. Another factor is the meme-ification of company valuations, where recreational investors increasingly look at everything other than business fundamentals when assessing a company, which results in there being disproportionate impact from executive choices or changes. Executive candidates can leverage this to get more comp either by carrot ("the stock price will go up if you hire me, so I should get a cut of that") or by stick ("it'd be a shame if you didn't hire me at my desired salary and something bad happened to your share price").

What have you seen be most successful for effective onboarding of new directors onto a board? What are common, easily-avoided pitfalls for boards of expanding organisations?

One thing I've seen that works _great_ is letting new board members go through employee onboarding! It's a super nice way for them to build relationships with a team and experience the culture of the organization, yet it's extremely rare for either board members or companies to do it. Some of the easy gotchas are not properly briefing new board members on the "basics" of an organization and its work, assuming too much fluency coming in, and also not having a structured onboarding process for new board members that spans multiple board meeetings. Also, have more good ways for board members to meet the team beyond senior execs!

Do board members know when things are going south and do they say anything?

Depends how and when. Financially? Usually, and they damn well should. In terms of product or process? Maybe, but it can be hard to distinguish from the normal background noise of people complaining. For people and workers? Rarely, as this is the thing that most often gets masked by the organization, either intentionally or unintentionally.

As a singular member, you're literally powerless without gaining the loyalty of other members, yes or no? Also, what are the opaque means by which institutional leadership makes it impossible for boards to control behavior?

Not always, but often. You basically have to build coalitions of agreement to get boards to be effective at anything. Ledares can mask things from the board often just by controlling emphasis of information sharing during things like board presentations. So if there's a serious issue, they might mention it, but downplay the seriousness or say that it's under control, and then the board will rarely suspect that the problem is deeper than it appears, because it's not as obvious as "they were hiding this big problem from us".

Can a board limit excessive kowtowing to shareholder demands? Can they, in effect, protect the health of the company against too much profit extraction?

A good board will think in the long term, and I've definitely had conversations with board members who explicitly talk about resisting the "solely maximize shareholder value" trap. But that culture is fragile and hard to protect, and all it takes is one person saying "why are you talking about all that hippie shit?" and it can evaporate. It's very hard to figure out how to get boards to add directors who have character and courage to speak up on that stuff.

from what context did you join boards, how did those board positions come about?

There's a pretty wide range of answers for me on that over the years. It's ranged from the fact that I started the company or organization in question, so I pretty much _had_ to be on the board, all the way to being recruited by people who I barely knew, but who knew that I cared about the work the organization was doing. In most cases, there has been a long period where I help out informally or as possible, sometimes for years at a time before anybody ever approaches me about helping on the board.

What does a board observer do? As an Angel investor, can I negotiate one?

Board observer roles can vary a lot, but they're very common, especially for either less-significant investors, or for other key constituencies like employees or even strategic partners. The key thing about an observer is that they don't have any voting power, but additionally they will often be excluded from executive sessions and more sensitive conversations having to do with things like compensation or personnel or strategic (mergers, acquisitions, etc.) work. It's a great way to learn if you can get access to that kind of opportunity.

range of relationships with the CEO/founder (esp as founder owns more and more of company).

This can really vary. In relatively rare cases when things are going poorly, the board can be actively at war with the CEO or founder. This sucks, and often gets very petty and personal, and nobodhy comes out of it for the better. Conversely, when a hard situation arises (for example if a company is in danger of going under, or an organization has an existential crisis), a good board pulling together to all help solve the problem is one of the most rewarding and inspiring things I've seen in a professional context. As founders get more and more power — not just ownership, but also new forms of control like super-voting shares and taking over chair duties in addition to CEO — there are a larger percentage of boards that couldn't hold leaders accountable, even if they wanted to. This is the kind of thing where effective regulation could likely help shift things for the better.

how monetary incentives shape board involvement

This varies a lot as well. I've seen people nobly walk away from massive amounts of money in order to do right by employees or "forgotten" founders, or to keep an organization on a stable footing. It's far more common to see people, especially investors, be nakedly in favor of maximizing short-term returns, and sometimes they'll even unapologetically do so knowing that they're hurting the organization. This is _far_ less common with board members who are truly independently nominated, and for whom being on boards isn't the primary way they make their living.

how callous about workers can they get.

I've heard stories from founders who heard, firsthand, their board members say, "fuck it, fire them all" and seen how devastated they were about the level of heartlessness they were facing. It's much more common for there to be more nuance, and a range of responses, though very often the level of empathy they have for a worker is directly correlated to how much a board member identifies with the person who's being affected. Marginalized people are at higher risk when their board doesn't see them as real people who share the same priorities and concerns.

what % think AI will solve every problem (I've already heard some wild stories about this))

Hard for me to speculate, as the boards I'm on aren't prone to trend-chasing (they tend to be circumspect about technologies, and see them as things to be evaluated in a reasonable way), but in general a _lot_ of boards are prone to looking at tech through the lens of whatever trends are getting a lot of media attention. Very few people get to the place of having enough power to be on a board while also having the technical fluency to truly evaluate new technologies at the level that an engineer or expert might.

How is this work balance with real full time jobs? And how does the real job feel about it?

It takes a significant time investment. Most of the time that I've been on boards, I've been the cofounder or executive of the organization where I'm working, so people were already aware that I'd be balancing these responsibilties. And very often, the people who work closely with em see how much perspective and insight I can bring to my work thanks to having served on these boards, so they see it as a worthwhile thing for me to spend a few hours on during work time every quarter. I do also do a lot of my board duties on nights and weekends, so it's much more of a case of balancing my personal commitments than my professional ones. Still, it's inarguably a big time commitment, and it requires support from a day job to allow you to consistently take that time away.

How do you know you are "doing enough" to justify being on the board?

Founders or execs (or board chairs) will absolutely let you know if you're not carrying your weight on the board, unless the entire board is woefully mismanaged. I tend to try to set explicit expectations of my participation, and also to set scope (like "I'll weigh in on tech questions") so they can properly anticipate what I'll do in my board duties, and then judge appropriately.

How do folks on their first board act different then after there are people used to being on boards?

This is a tough one; by far most of the people I've served on boards with have been on other boards before, with the possible exception of founders. There's a level of experience that comes from having seen common problems before, and it's indispensable when the inevitable problems arise. Newbies are more likely to panic.

What is your typical time commitment for serving on a board?

I covered this in the previous post, but basically it's a weekly-or-so cadence of keeping on top of news or updates, a monthly cadence of talking to team members (probably only an hour or so of time there) and then a commitment of at least a solid block of several hours quarterly for participation in board meetings. In all, it's probably a full working week per year.

What are the entry points to this? What are the things you wish you’d known when starting out?

I think a great entry point is trying to be of service to the sorts of people who run (or start) organizations. They will remember who was consistently valuable and level-headed, and then just be explicit about being interested in board-level roles. I wish I'd known how much of it is reading lots of spreadsheets or financial records, and how much of it is just building relationships that are durable enough to hold when things get stressful.

How to identify the difference between a good board and a bad board.

In short, the culture and the results. Are they transparent, communicative, and consistent? Or closed and flaky and lurching about? Does the organization have a clear strategy and goals, and does leadership talk about the board in terms of a common mission that everyone is working towards? Or is there a murky plan, with a resentful or passive-aggressive leadership team talking about the board like it's a problem to be managed?

Maybe it's niche, but I'm interested in how you think about board development and growth, your experiences as a board member "tuning" the board to better serve the organization (fwiw my interest comes from the tiny non-profit side of the board equation).

Governance over time is hard! One of the most common areas of failure is in not rotating out board members or bringing in new people as the organization evolves. It's hard to tell someone who's been valuable over time that they're not longer the ideal person to serve on the board. But it's almost always worth the effort to do so.

how do boards effectively influence the running of the business without treading on the toes of the executives?

The only thing that really works over time is having a trusting relationship to be able to have direct, sometimes difficult, conversations. Trying to influence things "behind the scenes" only drives drama and increases the likelihood of failure or stupid mistakes.

To what extent has the false, inhumane doctrine that profit-seeking corporations must always prioritize shareholder stock value gains over any consideration, ethical or otherwise, captured the brains of the governing elite?

Like... 80 percent? Maybe 85%.

How much agency do you have in setting the tone of the company/org? When do you know it’s time to leave?

A board probably _shouldn't_ have that much direct impact on tone; that's properly the job of the leaders who are there every day. But they should be aware and engaged enough to help leadership make corrections as needed, or to encourage them to do so if the leaders are neglecting to make necessary improvements. It's time to leave when someone else could be adding more value to the mission — there are always lots of smart people who aren't yet in the room.

What does a good board look like from outside? What motivates the board member actions? Is sole purpose to hire and hold CEO accountable, or is there more? What does the power structure look like within the board, within the organization, and within society?

From the outside, it can vary, but definitely look to make sure that it's not just a bunch of cronies who all went to the same university, or who hop from board to board together, rubber-stamping each other's ideas. There will always be people with an obvious financial conflict on the board, try to keep that percentage low. Generally people are motivated by the mission of the organization, and many times an affinity for the founder and/or leadership team. Sometimes people are just looking for resume padding or to have a certain credential. Power structures can vary a lot, depending on how active the chair is (and whether the chair is someone other than the founder or chief executive), the number and effectiveness of board committees, the level of engagement of individual board members, and how healthy the organization is overall. Within those constraints, it's sort of just like any other team — everybody has their own set of strengths, and alliances tend to form around common goals or interests.

seemingly small decisions taken at board level can have far reaching consequences with time. Can you give examples of where this may have surprised you, for the good or the bad?

This is a hard one. It's obvious when big decisions (hiring a new CEO is tricky!) have impact, but smaller ones often play out over a much longer time scale, and are only obvious in retrospect after a big catalyzing event like an acquisition or IPO or merger or the like. At those times, it's easier to look back and reflect, and very often it's not a case of "oh, we shouldn't have done that", but rather "because we made that decision at that time, instead of 6 months later, that's why we've ended up in this situation".

how do boards differ in American vs European contexts?

I don't know enough to answer this authoritatively. I've very seriously engaged with the idea of serving on one or two boards for European organizations, but have never actually served, so I don't have first-hand knowledge that would make me comfortable answering this.

I was recently elected to a tiny nonprofit's board. Which of the things I will learn will transfer to other kinds of boards?

Almost all of the procedural and structural stuff will be analogous to other boards. The rest depends a lot on how similar the other organizations are in mission, structure and maturity.

How do boards typically take in feedback?

From founders or execs, there can be varying degrees of formality, from side conversations at a board meeting to much more structured processes that work like a 360 review for a manager. If boards are soliciting feedback from other parties, like workers in an organization, there will usually be some kind of organized system so proper chains of command are respected, or so that disclosures or concerns can be addressed appropriately. A lot of boards to seem to operate in a vaccum, though, honestly.

When are board members compensated and how/why? (I'm not expecting money from either of my nonprofits but it's basically a second full time job for some people)

For non-profits, this can vary a lot. It's rare for compensation to be very substantial except at very well-funded, very large non-profits. I've never been paid for any non-profit board I've served on, though a couple times I got a nice dinner. In for-profit land, it can vary a lot, but basically startups do it almost entirely with equity and mature organizations have an entire board compensation process that resembles the usual executive compensation packages and incentives.

I'd want to know what encouraged you to serve on boards and (for the times you left and did not just cycle off, if there were any) what made you decide to leave.

Every time I've done it, it's because I believe in the mission and the team. I've left usually when there's a natural new chapter for an org, like significant structural or leadership changes, though in recent years it's become more common for me to step back as I focus on changing in my life or career.

I’ve always wondered how people who are on multiple boards manage to stay even somewhat informed about what’s going on in that many entities all at once. Like, isn’t that exhausting? Or are most members only aware of what’s happening on a "got a briefly right before the meeting" level?

I can only speak for myself, but as I mentioned in my earlier post, part of what I _love_ about being on boards is staying abreast of everything that's going on. It's like constantly getting to learn about a really challenging problem or interesting area of study, often alongside really smart people that I like a lot.

What training or skills do you find board members need to be useful?

I basically kind of wish every board member had the same training that I wish every high schooler got: basic sales training, how to read a P&L or a 990, enough coding to write a simple web app, some core fluency in how public policy about regulations in their domain work. Very few people take the time to learn that whole menu of things to even a basic level of proficiency, but anyone who's done each of them and kept up with a reasonable level of capability in those areas over time has a huge leg up on those who aren't curious enough to do so.

My general perception of boards is that they get the "great and the good" (people with a name, "grandees", you know) to sit on them but generally just rubber-stamp decisions. Am I wrong?

It depends a lot. There are definitely dusty old organizations where that's true, but then those places don't tend to include someone like me, so I don't have as much visibility into their cultures.

aside from being a sinecure for rich people, what does a board of directors do for a company?

Have I got a blog post for you!

If I'm looking at joining a mature startup as a sr employee, what should I look for in a board that shows that they know what they're doing?

I'd see above, "How to identify the difference between a good board and a bad board."

If you're an employee at a company, and you think the board is making dumb decisions, what is the best way to give them that feedback (and supporting evidence)?

This is a reall hard question to answer well, because the answer varies a lot. If there's an ethical or structural concern, a board will ideally have a whistleblower policy and process in place that you can take advantage of; these are generally pretty well run and can be surprisingly effective. But if it's more a case of "I disagree with our strategy", then... well, that's really, really hard. The overwhelmign bias of the board is to work with leadership, so even if you just decided to YOLO into the boardroom with a manifesto or PowerPoint saying "here's all the ways you're fucking up!" they're still almost certainly going to tell you, "okay great, go show this to your boss". Short of organizing workers, it's very unlikely a single person is going to upend the org chart through a direct entreaty to the board.

I'm curious how you think about your influence over the organization. What influence you have and how you learn enough in a limited time to give effective leadership.

As I said above, a board probably _shouldn't_ have that much direct influence, except in cases where things are really off track or they're asked to engage. It's much more about supporting leadership or encouraging leadership to reflect on their shortcominsg.

All my experience on non-profit boards has involved a ton of fundraising, something that makes me deeply uncomfortable. How do you navigate that requirement, particularly for non-profit boards?

The shitty but mostly-true answer is, you should get good at selling. Most non-profits are woefully unprofessional around many aspects of fundraising, and the kindest thing you can to to help as a board member is to take on some of that burden. Most boards will have a give/get requirement for precisely this reason. I personally like being expected to prove my value on the board at that level, not just through my direct work. I do sympathize that it's a very uncomfortable role for a lot of people, though.

organisational patterns and anti-patterns of boards. I suppose there’s a bit of Anna Karenina principle, but I’ve for example seen in a few boards how destructive it can be when board members try to corner each other instead of focusing on the organisation’s goals, which leads to burnout and factionism.

As I've said a few times here, the biggest anti-pattern is when you have a back-patting old boys' club in the boardroom just rubber-stamping each other's work uncritically. The toxic team-picking thing can happen, too, but that's usually much more a symptom of an organization that's going through hard changes; a company or non-profit that's running really well doesn't usually induce board members to dissolve into petty grievances.

What are your fiduciary and legal obligations as a board member, and when/how does that change for different kinds of organizations?

Mostly covered in my prior post.

I'm on a nonprofit board, and I'd like to know how it differs from a for-profit one.

Honestly, the most common difference is that the majority of non-profit boards, especially if they're larger or more established, will have some people on the board who are either not very experienced or who wouldn't make the cut in a for-profit context, but are there because they're true believers or were valuable along the way. That's not to say there isn't merit sometimes in giving them a board seat out of loyalty, but for-profit boards are generally far less sentimental about that. Then there are different structural and reporting concerns, and some vagaries of employment or fundraising law make the functional processes in a board meeting different, but that's more like switching between a Mac and Windows, everything is roughly familiar even if none of the small details are exactly the same.

Curious how much boards are in the loop with cybersecurity issues and if that has changed at all in the last few years.

There's almost always a review of risks and the organization's risk posture, and cybersecurity will certainly almost always be on that list. Levels of fluency vary, but again, a lot of board members are absolute boomers when it comes ot their level of technical expertise.

What do you do with all the checks they throw at you?

This question made me realize that I've technically never gotten a paycheck to be on a board. I've gotten equity in organizations (and, uh... _paid_ a lot of money to be on nonprofit boards), but the timing or opportunities never actually lined up for the various paid board roles I've considered over the years. 🤷🏾

What percentage of board members are also c level execs at very similar companies?

A _lot_. They can't be execs at directly competitive companies, of course, but it's absolutely the most common category of board member after investors and founders.

What's your favorite committee to be on?

This depends a lot on the organization and its stage of maturity. Certainly exec committees can be great for getting to work closely with CEOs or founders, and I tend to have been on a lot of audit or finance committes, I think mostly because I'm pretty willing to do that and not everybody is as willing or able.

Do think executives are generally honest with their boards?

The vast majority really are, in my experience. They might put things through a more positive lens, but it's actually pretty rare to be outright dishonest because the board is one of the few entities that could actually just get them fired for lying.

If the boards you’ve been on are responsible for hiring/firing the top brass (ie CEO): has being involved in that process changed how you view those leadership positions?

Leadership transitions are _always_ hard, even in the friendliest and most seamless of situations. I already have a ton of feelings about that that because I've been a CEO multiple times (though never at the scale of those running the organizations whose boards I serve on) but I have a shocking amount of empathy for people in those roles because very often bringing someone great in involves taking someone great out, and in many cases it's only because the organization has reached a new level that requires new leadership as a _direct result_ of them having done a good job. Like, you did so well in your role that someone else gets to have it now. Especially with founders, whose very sense of self or identity is often tied to the organization and its mission, that can be a heartbreaking conversation, even if everyone is doing their best to be kind and professional. I've said many times that being a CEO kind of almost _requires_ people to become a sociopath, because they're so inured to the power they have over others, but that doesn't negate that it's very real and very human for them to have a similarly stressful experience when they're on the other side of the power equation.

Phew! I hope this helps clear up a lot of the most common questions, or answers some of the more esoteric curiosity that people have. Thanks to everyone who shared their questions about boards!