The people-situation at the outset of my first CEO gig was rocky. We needed to grow and up-skill the team but were in no position to attract top talent. The company was midway through a sizable pivot, cash was dwindling, and our immature SaaS platform needed serious investment. Economic realities had dented our company valuation, making stock options an ineffective recruiting tool; and our dreary, subterranean office-space certainly didn’t help. So, we staffed-up the way so many other start-ups have done in similar situations: we hired eager, inexpensive recent college grads and gave them tons of responsibility. They loved it and responded with energy and enthusiasm. But they also desperately needed training, guidance, and consistent coaching. So, out of necessity, we got good at that.

Specifically, we grew adept in an area that is critical to any growing SaaS business: delegating meaningful work to entry-level employees and providing them with enough scaffolding to aid their near-term success while also supporting their long-term growth. This post addresses one small aspect of this broader challenge that so many growing SaaS businesses face: how to assign projects to less-experienced professionals in a way that works well for individual contributors, for their managers, and for the overall company.

First things first, it really helps for the company to identify one named person to be responsible for assigning work to any given entry-level employee. This may sound obvious, but is certainly not a given in many fluid, early-stage businesses. Among the benefits of this simple step is that it helps the employee avoid the complex, sometimes fraught responsibility of balancing simultaneous commitments to multiple senior people. It also ensures that assignments are given and received via one consistent voice, which avoids a lot of miscommunications.

Beyond the above, though, we’ve found the most important “must-do” is to support every assignment in writing. Even better, do so using a standardized format. A standardized format offers a structured, easy-to-understand written summary that codifies that project for the junior team member. Templates can take any number of forms; and below is an explanation of the template we’ve been using for this purpose at Lock 8 Partners:

Having introduced this tool, I feel obligated to acknowledge that any tool is only as good as a person’s ability to use it. And, while that topic is likely another blog post altogether, we have observed a few simple rules of thumb that help to successfully leverage this tool, including:

In closing, I need to acknowledge that there are no silver bullets to any human challenge; and this template is no panacea. Helping less experienced employees mature into seasoned professionals requires thoughtful on-boarding, purposeful training, consistent coaching, caring mentorship, and so much more. But because these initiatives often require more time and resources than are available in many small-scale businesses, we’re hopeful that this project template can offer a useful tool to help in building and growing your team.

We all want to prove our worth. We aspire to demonstrate competence, deliver value, and be recognized for our contributions to group goals. And this feeling is particularly acute for leaders during their early days in new roles with new organizations. From the moment they are introduced, new senior leaders are scrutinized by their management teams, by clients, by board members, and by many other stakeholders. Under these microscopes and carrying the weight of such expectations, executives are understandably eager to establish credibility and secure early wins.

In this environment, it’s also unsurprising that questions arise around the appropriate pace of leaders’ ramp-up time. Michael D. Watkins does an amazing job of tackling this complex issue in his book “The First 90 Days.” One of the useful concepts presented in that book is a leader’s “break-even point,” which is illustrated below:

Leader’s Break-even Point

Source: “The First 90 Days: Proven Strategies for Getting Up to Speed Smarter and Faster,” Michael D. Watkins, Harvard Business Review Press

Watkins points out that, although the timing to reach the break-even point can vary based on numerous factors, the goal is the same for virtually all leaders: “to get there as quickly and effectively as possible.

But rushing things exposes risks and traps that can lead to what Watkins calls “vicious cycles of transitions.” These cycles are characterized by an interconnected set of (a) inadequate learning by an executive, (b) ineffective relationship building, (c) lack of supportive alliances, (d) bad decisions, (e) lost credibility, and (f) organizational resistance. In sum, these cycles can kill any new leader’s plans for success. “The First 90 Days” combats these vicious cycles with a broad range of practical strategies for managing transitions with purpose and precision; and I recommend this book to anyone contemplating any new leadership challenge.

This post targets one aspect of this broad topic. It introduces a specific discipline that we’ve found to be consistently helpful in small-scale businesses in not only avoiding these vicious cycles, but also in accelerating leaders’ journey to the break-even point and beyond. It’s an astonishingly straightforward concept with impressive outcomes; but it can be challenging to execute in a leader’s busy days in a new role: The discipline is LISTENING TO PEOPLE. It is unquestionably simple; but the devil is in the details. Below is a quick explanation of the process, along with some tips and observations about why it works.

This approach centers around harnessing the power and value that comes from 1-on-1 interactions between people. It relies on a leader authentically engaging in individual conversations with every member of a team. As I wrote about here, it also demands that the leader clearly demonstrates his / her willingness to hear even inconvenient truths, and to create a safe environment for people to share their candid views. Note: while this practice would likely be infeasible beyond a certain scale, we’ve used it effectively in teams as large as 100. At the highest level, the process entails three key steps:

  1. Ask, Listen, Learn (and Record): First, schedule 1-on-1 sessions with each person in the company. Forty-five minutes is a reasonable length, but these sessions are often quite engaging and can last longer. It’s advisable to schedule these as tightly as possible following a leader’s start-date, but not so densely that they become rushed, impersonal, or a burden to be endured. We’ve learned that it’s a good idea to schedule the meetings in a random sequence, in order to allay any potential fears among the team of prioritizing any one person over another. The conversations themselves will center around a small set of questions asked by the new leader (more on those in a moment) and on the team members’ responses to these questions. These absolutely can and should be organic, authentic conversations; but it’s important to cover each of the questions. Along with listening actively and intently, the new leader’s responsibility is to record the feedback as exhaustively as possible.

    Why it works: Generally speaking, this is just the right thing to do. This practice also clearly conveys with actions (not just words) that a leader doesn’t think she knows it all (hint: no one does). Such an effort helps leaders to avoid the pitfall that Watkins calls “coming in with the ‘the’ answer.” It’s also an incredibly effective way of shortening one’s learning curve. It would be extremely difficult to collect in any other way such a diverse set of complex, highly nuanced, deeply informed perspectives about the business. And we’ve found that team members are amazingly thoughtful, introspective, forthright, and generous in their responses when engaged in this manner.
  2. Distill, Analyze, and Share: Once conversations are completed, the session notes should be anonymized, and put into spreadsheets, but otherwise left unedited. This allows for responses to be bucketed into categories, and for the leader to step back and holistically view the complete responses, distill the feedback, and identify trends or patterns within it. We like to share this artifact with the leadership team, in order that they can see the unedited, but categorized and anonymized, feedback. Note: this can be a real moment of learning for the leadership team members, as many will never have received this kind of feedback previously.

    Why it works: The feedback from the 1-on-1’s arrives in serial, concentrated conversations and can be quite overwhelming. Sorting it into categories and response-types allows for sense-making and for the macro-takeaways to emerge. It is also an effective guard against selection bias, which leaders can fall prey to if their introduction to the business is dominated by a few senior managers. This step also allows for a translation of qualitative information into quantitative metrics (e.g. 35% of people consider X item to be a priority, 42% of people believe the business is performing in Y manner, 72% of people are concerned about topic Z). All of this this will be helpful later as a leader looks to establish her case for implementing change in the organization.
  3. Present, Discuss, and Diagnose: The next step is for the new leader to present the findings back to the business. This tends to take the form of a brief presentation with slides as visual aids. It should avoid focusing on any individual quotes or single points of feedback, instead capturing the main trends and takeaways from the data. We like to start by having the new executive share with the leadership team. We’ll later share with the entire team, but its primary purpose at this moment is simply to inform and foster substantive discussion among the company’s senior managers. Those discussions, in turn, will help inform a hypothetical diagnosis of the business. That diagnosis is not yet definitive or final. Rather, it is a starting point — a hypothesis — around which in-depth quantitative research, detailed planning sessions, and draft strategic plans can be based.

    Why It Works: This step tends to elevate the discussion. The feedback itself can unleash an emotional response even among the company’s senior leaders; and this step allows the new leader to position the feedback as a catalyst for valuable learning rather than any kind of indictment of past practices. It also allows the new leader to exhibit a surprisingly informed understanding of the business after only a few short weeks on the job. This, in turn, is a great way for the leader to establish credibility and demonstrate competence. Lastly, the diagnosis helps to translate an eclectic array of inputs into a clear, concise, actionable form. But it does so on a tentative basis and without final judgement or conviction, which still invites input, augmentations, and even dissent from an ever-widening circle of team members.

An important remaining item still to cover is: what are the actual interview questions? Although these certainly deserve flexibility and can vary by business, we’ve had success with a few intentionally open-ended and precisely worded questions. These have been revised over time, and each is included for specific reasons. Those questions and related commentary are below:

  1. What business are we in? As I wrote about here, this question can be deceptively difficult to answer. It also often gently forces valuable discussions about things like your company’s business model, core competence, value proposition, required investments, talent needs…and misalignment or gaps across all of the above. It’s common for there to be a range of responses to this, with those gaps offering a great opportunity to work toward future alignment.
  2. How is the business doing? Again, this question often elicits diverse responses. Those responses sometimes reveal wide-ranging opinions among the team. They can also uncover inconsistencies between general perceptions people hold versus the story told by financials or other metrics. Without fail, this question sheds light on how information has been shared in the past: has it been a transparent culture, one that shields people from bad news, one that focuses exclusively on one view of the business while ignoring others? All of this is useful learning for a new leader.
  3. What is the real strength of the business? Again, so much to be learned from this question. Sometimes responses are overwhelmingly consistent (e.g. “Our strength is customer support.”). In other cases, responses are all over the map. In one case, members of virtually every functional area believed with conviction that their department was the lone strength of the business (needless to say, unity was NOT the strength of that business). In still other situations, a bit of probing can reveal that responses prove to be based more on accepted myths than on factual reality. This and more can be deduced from this simple question.
  4. If you were me, what one thing would you focus on? We’ve learned that this is a much better way for a new leader to ask about an organization’s “weaknesses.” No one wants to “rat out” a perceived problem area to the new boss; but people are generally eager to direct a new executive where best to focus his attention. This becomes about problem-solving and resource allocation rather than finger-pointing and blame.
  5. What do you hope never changes about the business? A new leader can be unnerving for any organization. This question offers a safe space for people to voice their concerns about a new leader’s priorities, without pre-judgement or negativity. It also provides an awesome guide-map for a new leader regarding landmines to avoid. Knowing what is critically important to people, allows leaders to easily navigate around the unnecessary pitfalls and build intentional bridges over the ones that simply need to be crossed.
  6. What would make this job / opportunity a home run for you? This question is obviously a stark departure from the others. But it is a critically important one in this process. It ties the well-being of each member of the team to the broader health of the business in a highly personal way. This is just good leadership. Understanding and paying attention to people’s love language at work or their ambitions for the future is incredibly powerful. And it is so darn easy to do — just ask people; and they will share.

Getting up to speed quickly and intelligently is a critical, recurring skill for all new leaders. It is our hope at Lock 8 that this framework will assist leaders on this high-stakes, high-reward, highly-complex journey to the break-even point and beyond.

Being a first-time CEO poses many new challenges, and one of the trickiest can be interfacing with a board of directors. Perceptive executives quickly realize that boards hold hiring-and-firing responsibility over them; and boards clearly have significant influence over the fate of any business. With that in mind, it’s no surprise that prudent CEOs focus on carefully fostering board relationships. Unfortunately, this very inclination toward care-taking can sometimes backfire and lead to costly mismanagement of the board. Beginning with my first CEO gig in 2007, I’ve made my share of mistakes on this front, a few of which are outlined below…along with a lesson learned that should guide all of a CEO’s board interactions:

Admittedly, getting these items just right is a learned skill that requires a lot of error-filled practice. But one realization has proven to be consistently helpful in keeping on track: The CEO’s primary job is to engage the board. Specifically, the CEO needs to enable board members to share their significant experience, learnings, and pattern-recognition to the benefit of the business. The CEO should give board members timely, accurate, relevant information…and then shut-up and listen. That’s it. If the CEO fosters robust, honest, unrestrained, challenging discussion among board members, everyone in the business benefits. So, forget about the pretty slides; and focus on getting the board to engage with unrelenting candor. It’ll be the best use of everyone’s time and worth every minute of investment.

In 2014 I found myself leading a SaaS business with a problem: how to hire executives to manage our company’s significant growth. It was a good problem to have, for sure; but it was still a problem. So, we scoped roles, identified job qualifications, established interview processes, activated our networks, and engaged recruiters. But mostly, we hoped. We hoped like crazy to avoid making a bad exec hire, which we knew would leave a trail of pain for months to come.

I was reminded of this personal experience last week while discussing the topic of exec hiring among a small group of entrepreneurs/operators. People consistently shared experiences of having anxiously faced, often unsuccessfully, this quite common business challenge. One entrepreneur helpfully shared the “GWC” framework that he had discovered while implementing the EOS Model outlined in the book Traction. The GWC framework is explained here, but the gist is that you should only hire people who:

In considering this framework, I realized that many businesses tend to over-index on the C (Capacity) in the hiring process. No surprise there; it’s understandable for us to optimize around finding someone who has the skills, experience and capabilities to get the job done. In fairness, many organizations fully appreciate the importance of culture and fit; so, the G (Get it) also gets strong consideration. But the W (Want it) often gets lost in the shuffle. Perhaps we are prone to assume or overestimate the degree to which someone wants to work at our companies. For whatever reason, the W receives less thoughtful examination compared to diligence around the G and the C. Reflecting on dozens (hundreds?) of hires over the last 20 years, I’m struck by how backward this is.

When I think about the truly great hires we’ve made, virtually every one of them had a very high W-factor. These are the folks who would run through walls, and whose desire was infectious. Conversely, I suspect that we can all recount failed hires where the C (and even the G) were very persuasive…but the W just wasn’t quite there. I’ll go one step further and say that a hire with a strong W can bridge gaps in their C and G (“where there is a will, there is a way”); but the converse simply isn’t true. Precisely why someone “wants it” is irrelevant, and the W can come from a wide range of circumstances; but it absolutely needs to exist.

To paraphrase the Rolling Stones: You can’t always get what you want; but hiring “want it” will definitely help get what you need.

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.

previous post on this blog outlined the struggle that many SaaS businesses face in driving a company’s product vision, strategy, design, and execution. That prior post offered some general concepts and terms aimed at demystifying this weighty responsibility, which includes codifying a well-informed product idea into a clear and compelling vision, and then translating that vision into a manageable action plan for a team. For the sake of brevity here, we’ll call those collective efforts “product management.” This post tackles the same topic, but instead examines how organizations evolve and mature in terms of developing product management capabilities as a core SaaS discipline.

Why focus on this topic? First, because product management is really hard; and many companies struggle with it. Second, because virtually every product management organization is trying to improve. And third, because we as humans inevitably want to run before we can walk. Similarly, many organizations naively desire to jump directly from their current-state (whatever that may be) into being a sophisticated, best-in-class product management machine. But it doesn’t work that way; there are no shortcuts. Rather, to be able to run a marathon, we need to commit to lacing up our metaphorical jogging shoes and following an increasingly rigorous training plan, in order to properly prep for race-day.

To be clear, this post does not pretend to be a step-by-step product management training plan. Rather, it intends simply to offer a competency model that captures what we’ve observed across many years and multiple SaaS businesses. Specifically, it lays out a competency framework for thinking about key milestones along an organization’s evolutionary journey in product management. Again, why? Because, although it is helpful to know what “great” looks like, it is also valuable to have a clear vision for what is one step beyond today’s current state. And, because every great journey starts with a single step, let’s get going.

First, we’ll need to agree on a simple premise: the better an organization is at product management, the greater and more positive that function’s impact is on the current and future performance and outcomes of a business. Now, if we were to plot that concept on X and Y axes, it might look something like this:

Maturity / Impact Framework

Setting aside for one moment the wide-ranging skills and capabilities that fall within the general heading of product management, let’s also agree that product management competency can range from very low (poor) to very high (expert), offering two ends of a spectrum. Using the “Maturity / Impact” construct above, it’s fair to state that the very lowest performing product management function has a correspondingly low (or even negative) impact on the related business. One might even say that the impact on the business is one of creating “chaos” (or at least failing to avoid it). Conversely, the most highly evolved product management organizations have a massively positive effect on their companies / products / customers. We’ve observed this to have a “transformational” impact on those same sets of stakeholders. In between these two poles, there are increasingly impactful gradations. We tend to think about it in the following five phases of maturity / evolution, as follows:

Maturity / Impact Phases

Please note: the above is NOT scientific or drawn to any scale. If it were to be drawn to scale, however, I believe the positive impact of Transformational product management capabilities (the last bar of the graph) would be orders of magnitude higher than the Chaotic or even Forming PM capabilities bars. They are simply incomparable in value.

Separately, there is another dimension to all of this; let’s turn our attention to the buckets of activities that comprise the product management function. Although there are countless ways to think about these responsibilities, we like to think about them in four general categories, as follows:

  1. Planning — Research, validation, and prioritization of product-related ideas and initiatives
  2. Execution — Generating the deliverables to allow near-term product development to proceed
  3. Engagement — Collection and analysis of continuous feedback both internally and externally
  4. Culture — Establishment and reinforcement of systems / procedures / norms for the team’s work

Within and across these four categories, there are a virtually limitless set of activities or tasks for which product management is responsible. The graphic below lays out a representative set of activities; and we think these are some of the more important ones. Because Culture supports and enables the other three categories, we draw it as follows:

PM Categories / Activities

Hopefully none of these bulleted items are terribly surprising to anyone who has spent time in a SaaS business. Unfortunately, there is a gap between knowing and doing, so a number of these items are frequently neglected or only nominally completed. In fact, when color-coded for what is comprehensively addressed (WHITE) versus NOT well-covered (GOLD) in a typical small-scale company, the list might look more like this:

Said another way, small-scale SaaS companies’ product management competency can be quite high in some areas, but quite low in others. And while this is arguably interesting in its own right, these activities become much more useful when overlaid with the phases of maturity outlined above. Specifically, performance levels across these categories dictate where an organization falls on the Maturity / Impact graph introduced at the outset. The graphic below identifies how Planning, Execution, Engagement, and Culture look at various phases of Maturity / Impact. This graphic brings it together, as follows:

Hopefully this model is helpful in its own right. But what we have found most valuable are the insights it has helped catalyze within SaaS businesses. I’ll share one of ours here:

Sample Learning: The framework allows managers to more easily and granularly understand how their teams are spending their time. Specifically, it was only when we bucketed activities, surveyed teams, and color-coded activities that we began to pinpoint unhealthy imbalances in allocation of time and resources. What we learned was that growing SaaS businesses we work in tend to be very focused on (and good at) cranking out the most pressing work (Execution). In fact, we’ve seen teams that focus 90% of their time on delivery of the current roadmap. Conversely, these companies tend to vastly under-invest in thoughtful, rigorous Planning, which can account for less than 10% of a product team’s time. Likewise, few resources tend to be directed toward getting consistent, multi-sourced feedback about that work (Engagement). If time and talent are a company’s most valuable resources, we should undoubtedly make sure that we’re using them wisely, through better Planning and Engagement. What this framework also taught us, unfortunately, is that you are only as good as your worst weakness. In other words, even if you are highly evolved in Execution or even Culture, you simply can’t make major strides forward on the Maturity / Impact framework if your Planning and Engagement are holding you back or dragging you down.

Having said all of the above, the looming question remains — what can product management organizations do to improve? In other words, how can we jump to the right on this Maturity / Impact graph? And, more tangibly, what tools or exercises can we implement to help get us there? Having now introduced this framework, it’s my plan to go into some of these tactics and tools in future post here on Made Not Found.

Thank you: I’d like to acknowledge and thank my good friend and former colleague Paul Miller for his contributions to this post. Paul has a clear, disciplined, creative product mind; and his thoughts shaped much of the above. It’s been fun noodling these ideas over the years with Paul; and he has been an invaluable collaborator in our shared and never-ending effort to get better at product management.

A core marketing objective for many B-2-B SaaS companies is to raise their profile by presenting at industry conferences. In theory, it seems like a surefire way to get your message to the right sets of ears. What could be better than presenting a session to a room full of prospective customers on a topic that is in your wheelhouse and gives you a chance to shine a light on your company’s value proposition? Unless…

The truth is that this can go wrong in so many ways. In fact, we’ve all probably been on the receiving end of some brutal presentations. But why the disconnect? What is it about industry conference “vendor” presentations that makes so many of them boring, ineffective, uninspired, or the perfect opportunity for attendees to check email? Having been to a lot of conferences over the past two decades, I’ve concluded that there are countless ways to mess this up…but that mistakes tend to fall into only a small handful of buckets. The following post lays out (in no particular order) seven “deadly sins” committed by us presenters — and how to avoid falling prey to their temptation!

1. Not Knowing (or Caring) Enough About the Audience

Anyone who’s ever received any training in presentation skills has probably heard this advice — know your audience. Although we all nod our heads in agreement, we generally don’t follow this wise guidance. Rather, presenters often proceed with materials largely unchanged from prior talks, other than maybe a few altered jokes. In a busy world filled with competing priorities, that’s the easiest approach…and it usually bombs. Here’s why:

Knowing your audience means caring enough to learn what they want from you.

This requires taking the time to step inside the shoes of audience members, NO MATTER THE TOPIC. For example, let’s say your topic is [X], and you want to emphasize the importance of [X] as a strategy to boost company performance. Now, imagine how a talk on this subject would be perceived differently if you are speaking to a room full of system administrators versus a room full of CEOs (or developers or marketers). Each is totally different. While CEO’s (hopefully) will appreciate what you have to say about [X] and performance, the audience of system administrators will likely have a very different experience. If you don’t thoughtfully alter your approach, at least one of those two audiences will likely have a sub-optimal reaction. They won’t find your clever jokes about [X] to be all that funny; and they might spend the session thinking about the many ways they understand or view [X] differently than how you describe. They may politely pay attention for most of your talk; but they are equally likely to leave scathing reviews on the speaker evaluation forms for the session.

You could have the audience members sitting on the edge of their seats — if you understand why they are sitting there in the first place.

Now imagine that rather than just repackaging the same tired routine, you stopped to think how you might approach the same topic differently from the perspective of the audience. You might have created a presentation on “how to be an effective executive leader in connection to [X],” or rather a session on “how to encourage effective use of [X] from those who may not even yet have heard of [X].” You could have provided a brilliant step-by-step guide for a target audience on how to use [X] to advance your career and build your network. You could have had them sitting on the edge of their seats.

As an example, there was an amazing Evangelist at one of my previous companies who would take the same general topic and completely transform the thrust of her presentations for senior executives (outcomes and impact), executive administrators (process improvements / time savings / efficiency gains), technologists (innovation and macro-trends), and CFO’s (risk, compliance, security).

Understanding your audience means you’ve made the effort to really understand what motivated that particular group of people to come to that session. That effort enables you to predict what will make the session as valuable as possible for that group, on that day, in that venue — and to adapt your presentation and your speaking style to deliver it to them.

2. Trying to disguise a blatant sales pitch with a clever title

First, I totally get it: public speaking at conferences can be expensive, time-consuming, and uncomfortable (public speaking is scarier than death to many); so you want to get something out of it. At some level, it is a means to an end — selling your SaaS product to the audience. And you may even believe so strongly in your solution, that the audience — once they learn about how awesome your product is — will forgive a few minor commercial plugs within what was supposed to be an educational speech. And because it’s just so good, you find yourself giving a quick sales pitch, product demo, or feature-focused walk-through of what your company offers. Sadly, believing something doesn’t make it so. Rather, nobody — zero people — will have more respect for your presentation, your company or your products if you do the old “bait and switch” routine.

If the title of your presentation promises a learning opportunity — then teach to the subject matter. If you’re truly knowledgeable in a specific area, and your presentation provides compelling evidence that would lead any sane person to the obvious conclusion that a productized version of your knowledge may be the solution to their problems, then you’ve done a great job. If, however, you feel compelled to blatantly tell the audience all about your solution, while the title of your session promises something different, you will have lost them in the first 30 seconds of speaking.

3. Creating a Slide Deck That’s Better Read than Said

We have all sat through presentations where the speaker simply read aloud what was already plainly written on the accompanying slide deck. And we’ve all had the same thought — “this is a complete waste of my time.” But there is a more insidious version of the deadly sin of reading your slides aloud — presenting an exhaustive, text-laden slide deck. While I readily acknowledge that there are places in the world for dense “briefing decks,” industry conferences are NOT among them. Rather, entrepreneurs / operators requested to present at industry conferences have a forum to educate, entertain, and engage the audience. The presenter’s goal should NOT be to present everything he/she knows about a particular topic, but rather to leave them wanting more.

To that end, your slide deck should seek to provide quick, impactful visual cues that give you a chance to tell an interesting story. If you’re like me and you tend to forget specific data points at times, it’s completely acceptable to write these data points in the presenter’s notes section. But the slide that the audience sees should only provide enough information to engage the audience. The best presentations I’ve ever attended actually had shockingly few words on slides. Rather, they were filled with provocative images that cued the presenter to tell an interesting story. Some really talented presenters (like Simon Sinek) rarely uses slides at all, opting instead to use a blank piece of paper and a marker to draw a concept real-time. Such presentations are memorable, easily repeatable, and compelling — precisely because they don’t use text-laden slides as crutches to do presenters’ work for them. Tip: many presenters spend 90% of their prep time creating slides, and 10% practicing what they’ll say. Flip those ratios; and see how it goes.

4. Attempting to Tell the Audience Everything You Know about a Subject

I’m clearly not the first to suggest that presenting fewer pieces of information through a handful of compelling stories is a successful presentation strategy, but it bears repeating. We humans are terrible at memorizing multiple complex ideas in a single sitting. We are far more likely to remember how the speaker sounded and looked than recalling a laundry list of important points.

Knowing this reality, do yourself a favor and present less stuff. Pick the 1–3 salient points that you know will be a home run with your specific audience, and then come up with interesting stories you can tell that make your case for you. Then create a slide deck with images that prompt you to tell your stories. I’d argue the greatest feedback any presenter can receive from a session is something along the lines of, “This session was really good, I just wish it had been a little longer.” Tip: Beyond limiting the number of points you make, no one will EVER be unhappy if you finish your session a little early; so keep it light.

5. Filling Your Entire Speaking Session with YOU

When entrepreneurs / operators are given a speaking slot at industry conferences, invariably the audience is wary. Generally, they want to avoid being “sold to” or “boasted at.” Meanwhile, the presenter is also wary — they want to be perceived as knowledgeable and authoritative (none of us wants to look silly or stupid). So, presenters often attempt to establish their credibility by sharing their qualifications…and commit the deadly sin of making the presentation all about them. This inevitably backfires with the audience. The moment a presenter fills too much time with the many ways he / she is personally and professionally wonderful, you can almost hear a “whoosh” as audience members picks up phones to check Slack or Twitter.

Your job as a presenter is to give the audience the information they want (see point 1). So, don’t be tempted into thinking that the best way to win over the audience is to prove how smart, capable and successful you are. Having witnessed this approach many times, this rarely works. Rather, the presentations that receive the greatest buzz are those where the audience is engaged — where the presenter goes out of her / his way to make as much of the material about THEM as possible and only about her / himself when providing a more personal anecdote would illustrate a point in a humble, unassuming but totally identifiable way. For example, I’ve learned that poking fun of my own baldness offers a way to quickly inject some relevant personal experiences, while still keeping the tone appropriately self-effacing (warning: only try this if you are, indeed, bald).

Another strategy that can be successful — when done right — is to share the limelight by creating a panel of people who will discuss a topic. But beware — when done wrong, panel sessions can become the deadliest of sins (see below).

6. Facilitating a poorly planned, really dreadful panel discussion

It seems like such a foolproof way to win over your audience: simply pick a compelling topic, create a panel of 2–3 smart people (potentially customers and fans of your company), and then just ask them a series of questions. Right? Well…maybe. The panel CAN be a successful way to accomplish a few objectives easily:

But this approach can utterly fail if you as the moderator don’t bother to understand the nuances of how each panelist differs, what unique information or strengths each panelist brings to the discussion, and the best way to cue each panelist to deliver the most salient information. We’ve all seen panel sessions that were moderated poorly — where the moderator lazily asks every panelist the exact same questions, and each panelist (to avoid seeming either unprepared or impolite) just agrees with everyone else on the panel, and then tries to add a unique spin that really is just a paraphrase of what has already been said. Other panel moderators seem to think that having a panel absolves them of any prep work — like they can just show up and start asking random questions to a group of strangers and magic will somehow “happen.” Not so. Rather, the moderator has one very important responsibility:

The panel moderator’s job is to help panelists tell compelling stories that make the panelists look their best.

If you do this right, the panel discussion can shine a bright and favorable light on you and your company — because you are obviously the kind of SaaS leader who actually cares to get to know people. You care so much, you understood that the CEO from the hospital who was on your panel had very different challenges than the General Counsel of the family-owned company — and you skillfully selected (with ample pre-session prep calls with the panel) just the right questions to pose that allowed each panelist to shine as they told a really interesting story. You made it look like the group was up on the stage enjoying a riveting conversation — one that the audience just happened upon and is now sitting on the edge of their seats dying to know what’s going to happen next.

Which brings us to the final deadly industry conference presentation sin.

7. Calling yourself a panel moderator, and then behaving more like a “puppet-master.”

As described above, a good panel discussion requires a moderator who understands each panelist’s context, way of thinking, and knack for speaking — and who has carefully curated a set of questions designed to help each panelist showcase their best selves. Woe to the moderator who falsely believes that what the audience really wants is to hear her/him answer every question alongside (or instead of) the panelists. A cousin-sin to this is when the moderator feels he / she needs to synthesize and summarize all of panelists responses. There are many versions of this, and they all can appear scripted, unauthentic, and self-serving.

In short, if you’re going to invite panelists to join you on stage, recognize that they have an opportunity to help your message shine — but only by being their authentic selves. It’s completely acceptable for you to cultivate a discussion on-stage — even a contentious one — as long as it’s all done in a respectful way, where each person has the opportunity to share diverging viewpoints without attacking each other (attack the ideas, not the people).

The truth is that these sins are easy to spot, and very hard to avoid committing ourselves. I hope this post is helpful in avoiding them in any future presentations.

I have admired the work of Walker White for years and have valued the opportunity to compare notes and share lessons-learned with him during that time. At this point, I am excited to explore ways to expand and deepen that collaboration. With his recent transition following a long and successful run at BDNA and its acquirer Flexera, Walker will play a more active advisory role to Lock 8 Partners. This week Walker shared on LinkedIn some of his thoughts and observations from 25 years in leadership roles in the tech space. His post really resonated with me, and I wanted to share it here on the Made Not Found blog.

28 Words on Leadership, by Walker White

After 25+ years, it is time for me to shake it up and pursue career 2.0. I’ve been fortunate to be entrusted with leadership roles over that time, and in an effort to continue learning, I kept a running list of quotes and anecdotes that struck me. As it is good to pause and reflect during any transition, I recently found myself reviewing that list. Sometimes with a chuckle and other times with a sigh, I was reminded of when I heard them, what they meant to me, and how I put it into action (or didn’t, hence the sighs). I thought I would share four of my favorites:

“Culture eats strategy for breakfast.”

“You get what you tolerate.”

“Everything is in walking distance if you have the time.”

“Control leads to compliance; autonomy leads to engagement.”

When you hear a quote or anecdote that resonates with you, take the time to jot it down. In my experience, so much of leadership is common sense, but the pace of the day-to-day often caused me to over think the best solution. Simple quotes — like those above — always served to ground me back to what really mattered and more often than not illuminated that which I had overlooked.

Still learning and laughing,

Walker White

Walker White recently left his role as Senior Vice President of Products at Flexera to pursue Career 2.0. Prior to acquisition by Flexera, Walker White was the president of BDNA Corporation. He is passionate about helping organizations excel by building the right team and culture, setting and communicating a compelling vision, and driving momentum through courageous decisions.

We all want strong culture in our organizations, communities, and families. We all know that it works. We just don’t know how it works.

The Culture Code by Daniel Coyle

This short video takes a quick look at this great book and adds a few thoughts for those looking to put some of its ideas into action.

Hopefully, this added perspective will make an already awesome book that much more actionable and valuable to leaders of growing organizations.

Cats and dogs. Oil and water. Hatfields and McCoys. Some things just don’t play well together. In fact, they seem almost purpose-built for conflict. I was reminded (again) this past week that the SaaS version of such predictable tension is the running feud between Sales and Client Success departments. There is undeniable and inherent tension between the two groups, and it’s easy to see why: the remit of Sales is to maximize bookings / hit targets in the immediate-term, whereas Client Success is responsible for turning every customer into raving fans long into the future. But this doesn’t need to lead to incessant battling. In fact, I’ve found that a few simple exercises can go a long way toward disarming the inter-departmental combat.

1. People Are People

I’ve observed that a fair bit of this conflict stems from a simple value-perception problem. Specifically, bookings are valued very highly in young SaaS businesses, with new sales (and often Sales people) celebrated as a life-line during a company’s fragile, early days (I wrote a bit about this here). Somewhat irrationally, those same organizations tend to be less overt and unrestrained in celebrating renewals, which lead to multiple years of recurring revenue. The predictable result is inequity in terms of how team members in Sales and Client Success perceive they are valued in the business. This, in turn, can breed resentment and conflict. A simple solution to this pervasive problem? Have the groups talk about it. But, to avoid reverting into counter-productive naming and shaming, be sure to do it in a thoughtful and structured way. I particularly like the following simple exercise:

With each person using a sheet of paper, ask people from Sales and CS, respectively, to privately rate and record on a scale of 1–5 their responses to the following two questions:

Then have them exchange papers and discuss. No matter the written responses, substantive and productive discussions generally ensue. Why?

2. We Mock What We Don’t Understand

Let me say that I just don’t buy the argument that Sales and CS people are just intrinsically different and incompatible. Rather, my experience is that they both want the same things — to win in the market, for their customers to be successful, and to thrive as a company and as individual professionals. The two groups just define and prioritize those objectives differently, (which is hardly surprising, given their respective areas of responsibility).

Beyond that though, the groups generally just don’t understand each other well. Again, this is unsurprising: SaaS businesses are fast-paced, resource-constrained environments. So, it’s far too rare that people receive adequate training on their own job function, let alone on the responsibilities of others. As a result, people have only a vague understanding of others’ work and almost no appreciation for the things that can make that work difficult or frustrating. And while people are hyper-aware of what they themselves produce, they are far less cognizant of their cross-department colleagues’ work product. The exception to this, of course, is when their peers’ actions make their own job more challenging…in which case the cross-department ceasefire is cancelled and hostilities resume. The painfully obvious (but difficult to execute) solution: educating people about the inter-dependent nature of their departments. For this, I like an exercise that centers around what each job function (a) produces and (b) consumes from the other.

Instructions: Ask members of Sales and Client Success to work together to identify 3–5 things for each of two categories:

I specifically like to create a grid where groups can brainstorm in isolation about what one department produces for the other. And then you do the same thing for what that department consumes from the other. Then switch departments. Because people from different departments are working as one group in this exercise, it tends to highlight just how different their perceptions / responses / pain points are at the outset…and how much and how quickly they learn to bridge the gap. I’ve focused this on Sales and CS here, but I like to do this one across all departments. The end result of this is a Give-Get Grid, which I wrote a bit about here, and which I’ll go into in more depth in a future post.

3. Our Strengths are Our Weaknesses

I’m a fan of the Gallup StrengthsFinder assessment for many reasons. Among them is the fact that it gives us language to call someone out for counter-productive behavior, but to do it in an inoffensive way. Specifically, StrengthsFinder is a diagnostic that allows people to identify what their core strengths are in terms of how they think, work, and view the world. Like many diagnostics, the explanatory write-ups for each of the framework’s 34 Strengths tend to resonate clearly with people when they receive their personal test results. And one of the most valuable parts of the assessment, for our purposes here, is how it convincingly and pragmatically points out this truism: our greatest strengths — left unchecked — frequently also present themselves as our great weaknesses. For example, “people exceptionally talented in the Activator theme can make things happen by turning thoughts into action. They want to do things now, rather than simply talk about them.” This is awesomely valuable when the situation demands speed. But this inclination can be counter-productive in situations that require great care, planning, or coordination. Likewise, Activators can be incredibly aggravating to those for whom Focus — “following through and making the corrections necessary to stay on track by prioritizing, then acting” — is their top strength. In such a case, it is undeniably better for the Focus person to politely / humorously ask the colleague to “tamp down their Activator tendency” than it is to tell them that the whole team wants to strangle their impetuous, hyper-active, cowboy throat. You know how these conversations can go…

Give People a Pass:

In closing, I want to broaden the scope beyond Sales and CS to cover all departments; there is a degree of tension among all of them, and they can all stand to examine how they intersect. I also want to acknowledge that these minor tactics / frameworks may be powerless in the face of true interdepartmental dysfunction or deep personal animosity among team members(!). But if that is the case, then more serious measures are likely needed to change the team…or change the team. That said, I’ve observed that most issues arise in an environment where different departments truly do share goals and respect for one another — they just need help getting aligned.

In such cases, we all need to step back and just give people a break. That’s right, give them a pass, and lay down your inter-departmental arms. Recognize colleagues’ perspective and take the high road, already! The Hatfield-McCoy thing does no one any good, and more importantly, isn’t worth the distraction from the ever-pressing needs of clients and the business at large. Frankly, it’s a pure waste to dwell or be mired in it. Use it; work it to affect mutual advantage and company success. There is usually a way. Find the leverage. It’s there to be found.

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

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