If humans are truly social animals with an innate need to interact with others, then why do we hate meetings so much? And if meetings are bad, then why do we find extended offsite sessions even more brutally intolerable? With offsite planning season soon upon us, such questions are worth asking and answering…and just maybe…offering some tips to ease the pain.

First things first, meetings are unbearable for thousands of reasons. But they all come back to one simple idea: opportunity cost. We’re all busy, with far more responsibilities than time to manage them. And we’re haunted by the excruciating realization that time spent in meetings could be far better invested in other pursuits. But what if that didn’t have to be the case?

Much has been written about ways to make meetings more effective, with innovative companies like GoogleAmazon, and Bridgewater each having its own unique approach to meeting management. This post attempts to contribute to that impressive body of work by offering one simple tactic that has consistently helped improve our own meetings and offsites over two decades and many businesses.

We call it a “pre-mortem,” and it’s based on the concept of a “post-mortem.” A post-mortem is an examination of a dead body to determine the cause of death. In the context of business, a post-mortem is a common project management practice in which a critical retrospective is performed to learn what went right and (primarily) wrong in a given initiative. In other words, what was the cause of death? We’ve taken that same concept and put it at the beginning of the process when hosting a meeting. A pre-mortem pre-emptively asks the uncomfortable question: what could possibly kill this meeting?

The way it works is simple: the meeting leader starts the meeting by asking each attendee what would make the session an abject failure for them. Then, each person let’s fly with their worst fears about how the meeting could turn into a slow-motion car crash. The meeting organizer captures the shared comments on a large, visible white-board or sticky-note. Next, the group takes the time (usually 10-ish minutes) to discuss the comments, often with clarifying questions and conversations about how these failures might occur…and what can be done to avoid them. Importantly, the group commits to work together to avoid the negative outcome. The meeting ultimately commences and proceeds in an otherwise typical manner, with the pre-mortem being the last item revisited (again, for about 5–10 minutes) prior to adjourning. We’ve found the results of this to be…well…really good. Is it magic? No, nothing is. Does it help to make meetings far less brain damage? Absolutely.

Before offering some thoughts on why this tends to work, let’s first explore a “dirty dozen” of the comments that commonly appear on these lists. In no particular order, responses include:

  1. We are going to re-litigate issues / decisions that we’ve already made previously
  2. We are NOT going to openly re-litigate issues, but they’ll be debated later behind closed doors
  3. We’ll have good discussion, but there will be zero follow-up or action taken afterward
  4. What gets shared here will not be held confidential, and there will be post-meeting gossip and organizational fall-out
  5. Some people (you know who you are) will hog-up all of the air-time and dominate the meeting
  6. We’ll focus on the same topics that we always obsess about, while ignoring other critical issues
  7. We’ll navel-gaze, without considering external (e.g. market, customer, competitor) perspectives
  8. We won’t follow and agenda; and we’ll be all over the map
  9. We’ll ONLY follow an agenda, and the meeting will be an obligatory check-list to be completed
  10. People will be distracted by email / Slack / phones / social media throughout
  11. People will be rude and confrontational…OR…people will be overly polite and avoid all conflict
  12. Meetings are useless…we should all just do whatever we want (this view we just can’t solve)

There are countless other issues that people have with meetings, but this is a pretty good representative sample.

Now…why is this approach so effective? One undeniable reason is that naming problematic behaviors or practices tends to put people on notice — don’t be this person! More than that, it gives us a spoken, commonly, acknowledged, up-to-the-minute benchmark against which to hold people accountable if they violate the boundaries. This also provides a language and a tool to gently call people out when they do fall afoul (it’s easy to simply point to the sticky-notes when someone flagrantly blows through item #7). More than any of these though, people in growth businesses tend to “hate to lose” far more than they “love to win.” Said another way, it’s not enough to enumerate what GOOD meeting practices are — people won’t change their behavior to meeting that threshold. But no one wants to be the person who obviously fails to live up to basic standards of meeting professionalism. So they tow the line…and the collective behavior change makes for massively improved meeting outcomes.

Give it a try some time; and please let me know how it goes, what you learn, or how we can further refine and improve this approach.

We’ve all been there — stuck between a rock and a hard place. In the small-scale SaaS world, there is a particular version of this universal issue. On the one hand, we need to rapidly broaden and deepen our product offering, in order to increase our product’s appeal and expand its addressable market. On the other hand, we need to generate immediate-term sales dollars, even if what the customers want / need / think-they-are-buying creates misalignment or friction against our existing solution and the product direction we’re seeking to fund with these very sales. It’s a vicious, unforgiving dynamic that can be a difficult cycle to break.

In spending time recently with a number of small-scale business operators, I’ve heard this issue come up frequently. Which reminded me of a couple simple exercises and tools that can raise awareness around this issue and help organizations avoid this tempting trap. Really, it comes down to the cost-benefit of signing on new customers in an unselective way. We tend to see and quantify the benefits of new customer acquisition very clearly: “this deal will bring in $X of recurring revenue and $Y of cash today!” What we don’t see even remotely as clearly is the organizational cost / burden of servicing that customer.

One effective exercise to combat our blindness on this issue is to fill out what we lovingly call the “Cascade of Pain.” In the Cascade of Pain, we have a diverse set of team members conjure up an existing customer that is particularly challenging to satisfy. Most every company has at least one customer in their early days where this is true: “No matter what we do, we just can’t seem to deliver to this customer what we’ve promised; they just aren’t a fit for where we are today.” In this exercise, we then we go through — department by department — and identify the range of pain that our organization has experienced as a result of our having sold this ill-fitting client (or multiple clients). Below is a sanitized version of the type of output that typically comes from this exercise:

Sample: Cascade of Pain

Captured it in this way, it becomes clear that the pain from signing bad-fit customers is a burden on everyone across the entire organization. Sometimes simply codifying the pain is enough for organizations to recognize and reign-in ill-advised sales. But let’s face it, the pull of prospective revenue is powerful and the pressure to drive sales is unrelenting. In these cases, it also helps to be highly prescriptive on the front-end about deals to chase versus those to be avoided at all costs. The relatively simple exercise of establishing “Right Fit” criteria for your product can be very effective. Basically, this exercise comes at the same problem from the exact opposite perspective by asking: “What do our best customers look like / what do they have in common?” This goes far beyond the most obvious questions such as market segment (e.g. wholesalers vs. resellers vs. retailers) or size of customers (e.g. SMB vs. mid-market vs. enterprise) and gets more to the heart of how these customers interface with our company and our solution. Below are some of the questions that commonly come up:

Each category or product will have its own unique questions, but these tend to be broadly applicable. Capturing them is a critically important step, but it is really just the beginning. Incorporating them into the company DNA is an organization-wide and ongoing endeavor. It includes identifying which “Right Fit Criteria” have some latitude versus which ones are non-negotiables. It also has a major training component — certainly among sales people for use in the selling process, but also across all departments. Some systematization also helps — for instance, including some version of these questions as fields in your SFA platform. Finally, it is always a good idea to establish some processes around them. For instance, in those cases where we are knowingly going to go after a customer that falls outside our strike-zone, at least let’s make sure that we do it with sign-off from all of the necessary / effected parties, full knowledge of where the gaps are, and a plan from the get-go as to how we are going to mitigate the risks.

Because the truth is that it is our job in small-scale companies to test the boundaries of what is possible and to stretch the limits of our products and our organizations. But, that doesn’t mean we should do so blindly, or without having first clearly identified precisely where those boundaries are, and where we are comfortable pushing them.

I frequently hear people use the term “playbook” when discussing methodologies for building businesses in a rational, replicable, and scalable way. It’s hard to argue with the concept of establishing consistent best practices and optimizing critical success factors; and some investors have leveraged and honed this strategy to deliver absolutely phenomenal returns over many years. I certainly wouldn’t question these results or the benefits of such a scientific approach. Where I get leery is when people describe this kind of a sophisticated blueprint as “having a playbook” or intimating that business-building can somehow be distilled into a straight formula. And I’m definitely not a fan of the notion that a “playbook” alone is the key to assured business success. I acknowledge that the term “playbook” may just be loose shorthand, so perhaps I should chill-out and not take it so literally. But the metaphor of a standalone “playbook” carries a number of counterproductive implications that I consider are worth flagging. These include:

  1. “Playbook” can imply an artifact that represents a fixed level of completeness or totality that is simply non-existent in the business world.
  2. “Playbook” seems to elevate “the plays” as being of utmost criticality, while understating the importance of (metaphorically) reading the game, knowing which plays to call when, or having the confidence to change or modify plays mid-game, based on situational realities or market dynamics.
  3. “Playbook” arguably ignores the hard truth that someone needs to execute those plays. The skills, mindset, and experience of that person(s) greatly impacts the outcome of any given “play.” And the X-factor of how a team functions as a unit may be the greatest success-determiner of all.
  4. “Plays” themselves feel like correlates to “tactics.” And while tactics are critically important, they cannot stand on their own. Per Sun Tzu in The Art of War (with apologies for the mixed metaphor): “Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.” More to come in a later post on establishing a strategic platform, from which tactics can be leveraged with purpose.

Lew Moorman of Scaleworks said it better still with this 2018 quote: “There’s no playbook on how to build a business. But there is a set of disciplines that can be taught in terms of experimentation. Looking at the data, there are just some patterns.” I really respect what Scaleworks does; and I couldn’t agree more with this sentiment. These “disciplines” feel adaptable, applicable, actionable, and agile…bringing a critically valuable dynamism to the straight X’s and O’s of a static playbook.

In my mind, just a few of those teachable disciplines include:

While it certainly has a major part to play, a playbook alone cannot be expected to instill these types of disciplines in an organization. Rather, a playbook is but one part of a larger ecosystem that fosters these kinds of disciplines. It goes hand in hand with with engagement models, values that shape organizational behavior and decision-making, strategies to align initiatives, and frameworks / artifacts / systems / processes to facilitate execution. I hope to further examine and unpack all of the above in many future posts.

Are we speaking the same language? Let’s talk.

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