One of the benefits of the SaaS delivery model is that it enables an iterative approach to product development. Because of the relative ease with which software updates can be delivered, SaaS solutions evolve fluidly and organically, with small improvements, enhancements, and fixes introduced often in a seemingly steady stream. But this does not mean that major upgrades are a relic of the past or that big-ticket development initiatives are obsolete. Rather, even with the most thoughtful product planning, time has a way of cruelly revealing ill-advised feature choices, scale-limiting technology decisions, and ever-changing market needs. In this way, each incremental release of new code propels SaaS businesses along a predictable path toward a crucial and somewhat unavoidable question:

Whether to continue building onto an existing solution (with all its pros and cons), or to re-think the whole approach, with the benefit of invaluable knowledge learned over time?

Such initiatives come in many flavors and go by different names, such as: re-platform, major upgrade, re-write / re-build, next-generation development, future proofing, and addressing tech-debt, to name just a few. Nearly all successful software companies contemplate such an effort at some point in their life cycle; and it is a fraught decision with existential ramifications. While the benefits of these types of initiatives can be positively transformative, they also represent significant potential costs and risks (e.g. large investment of time and resources, opportunity costs for projects not pursued, freezing new client sales, brand-damaging disruption and alienation of existing clients, and loss of critically important subscription revenue). Having participated in a number of these major initiatives as an operator over the years, I’ve come to appreciate that these are extremely complex and there are no silver bullets. Likewise, every one of them is unique; and yet, these situations share numerous characteristics and dynamics, with applicable lessons to be learned from each. With that in mind, below are five quick observations and takeaways relating to this common, yet extremely high-stakes, situation.

Note: For simplicity’s sake, I’ve used the term SaaS throughout this article, although these principles apply to any number of modern software delivery models. This raises the important strategic decision of how to utilize cloud services while modernizing the architecture of a SaaS solution. I don’t intend to address that topic here, but will plan to tackle it in a future post.

1. Strategic Clarity: To quote Simon Sinek, “start with why.” Be very clear on precisely why you are undertaking such a monumental endeavor in the first place. What specific results / benefits do you expect to achieve and how will those benefit your customers and prospects? If you can’t concretely answer these questions and communicate them honestly and with conviction to customers (no spin!), then the whole initiative may warrant re-thinking. Likewise, be very explicit about your strategy, and don’t compromise on it. At a high-level, what is the approach and the thinking behind how you seek to achieve the goals identified above? Tactical and execution questions will arise, but don’t blur them with strategic questions. Moreover, don’t confuse strategic risks (those that are inherent in your strategy and cannot be meaningfully controlled or managed) with actual risks that can and should be mitigated. Once the strategy has been set, focus maniacally on controlling those execution risks that can be actively managed.
2. Beard-scratchers Welcome!: Projects such as these bring big, messy, strategic decisions that impact all parts of the business. Accordingly, it is important to make plenty of “white-space” in people’s schedules to allow for extended and unbridled debate at all stages of these projects. Moreover, these debates need to include a wide range of constituents with different perspectives. In some ways, this is counter to the “get-done” culture at most small-scale SaaS businesses, where the inclination is more “to do, than to think.” In these companies, we try to protect people’s schedules, in order that they can crank out the important work on their plate. Likewise, we tend to strive for efficiency in our meetings, with tight agendas and a minimization of any wasted time (“let’s get back to actually doing stuff!”). It is critically important to fight this urge and to get in a room and debate. These are almost never “30 minute” decisions; they need to be given the room to breathe and the benefit of many people breathing life into them.
3. Landing the Rover on Mars: It is paramount that the whole organization understands the long-term product vision as early as possible. The far-reaching vision impacts not only near-term product decisions, but also virtually every supporting operating decision across the entire organization. This will ensure that decisions that are made today at all levels of the organization actually support ultimately arriving at our envisioned destination for the future. And, make no mistake, every seemingly small decision will have a material downstream impact. We’ve used the following metaphor to help drive home the implications of this point: “If you want to land a Rover on Mars…be precise in your trajectory. Because, the distance between here and there is so large that if you are one degree off target…you will wind up on Pluto.”
4. All-In vs. Modularity: This point refers to the concept of a platform, environment, eco-system, or suite of solutions — terms that SaaS businesses tend to use to describe their product sets. Most SaaS providers contend that customers will derive disproportionately large benefit from holistically adopting all parts of a “platform” in concert, versus cherry-picking one-off products or functional modules. In this way, 1+1+1 should equal 30…not 3. At the other end of this spectrum sits “modularity,” which connotes (among other things) freedom of choice. Specifically, customers can elect to mix best-of-breed products or point solutions to address their business needs. Each of these approaches has strengths and weaknesses; and I’m not here to argue one over the other as being universally superior — as always, context matters. However, it is absolutely worth examining the goal of a given initiative through this lens. Where on this spectrum does your company expect to position its offerings at the successful conclusion of this initiative; and how will you convey value to prospects and customers? Whatever that point is…identify it, embrace it, and own it. So many product and go-to-market decisions will be driven by this decision; and the only truly bad decision is no decision at all.
5. On-Ramps and Highways vs. Parallel Surface Roads: Because the dangers of negatively impacting current customers with any kind of disruption are so scary, we tend to be risk-averse in these efforts. It can be helpful to compartmentalize these risks with the help of the following metaphor: The current / legacy solution represents surface streets for clients. Those windy, narrow streets get them where they want to go, but the routes are often slow, fuel-inefficient, and require local knowledge. Our revolutionary new solution represents a super-highway — high-speeds, easy navigation, and clear line of site to desired destination. Clients understand the benefits of the highway, and they want to travel on it; but making the cut-over from surface streets can be intimidating and treacherous, so they are reluctant to make the switch. Their concerns can lead us into playing it safe, by minimizing change and simply recreating / replicating existing functionality in the new platform. Don’t succumb to this temptation — doing so is analogous to paving parallel surface streets — ultimately no better and no faster than the existing ones. Second, on-ramps describe how clients gain access to the new solution. SaaS businesses need to provide clients with multiple different “on-ramps” so that clients can choose WHEN, HOW, and HOW FAST they choose to move over and adopt the new solution. Paying close attention and investing heavily in providing many different on-ramps (not just one-time or one-size-fits-all) are the best ways to ensure that all clients ultimately elect to get on the highway.

While these concepts are applicable in many ways, they are just that — concepts. They need to be applied in pragmatic ways that make sense for each unique reality that SaaS businesses face. As stated above, there are no easy answers to solving to these supremely complex issues; but hopefully the tenets above will help folks navigate these major initiatives as they arise.

With those fateful words, the meeting ends on seemingly solid ground. Unfortunately, too often a team’s commitment begins to erode almost immediately after adjourning. In these scenarios, a corrosive force is hard at work, devastating teams and laying waste to even the most solid plans. It’s called re-trading, and it takes place when someone(s) revisits a settled decision with the intent to change plans after the fact. This post attempts to shine a light on the toxic team behavior and offer some thoughts for combating it. But first let’s take a step back and offer some context:

“Disagree and commit” is a management principle which states that individuals are allowed to disagree while a decision is being made, but that once a decision has been made, everybody must commit to it. According to Wikipedia, this principle has been attributed to such icons as Andy Grove, Scott McNealy, and Jeff Bezos. Whatever its true origin, it “pinpoints when it is useful to have conflict and disagreement (early states of decision-making, but not after the decision is made). It is also helpful in avoiding the consensus trap, in which a lack of consensus leads to inaction.” In general, this principle is useful in organizations that value different perspectives but have finite resources to pursue seemingly unlimited ideas (i.e. in most growing SaaS businesses). It works well, so long as people commit in good faith to a plan and then maintain that commitment even in the face of inevitable adversity. It fails miserably when people’s commitment wavers and they seek to revisit the original decision via a re-trade. The re-trade can present itself in any number of different forms, including:

• The person who never liked, nor cynically ever had any intention of committing to the plan
• The person who didn’t pay close enough attention to the detail, and now does not feel beholden
• The person who does his / her own thing and doesn’t even realize they are deviating from plan
• The person who believes that ever-changing circumstances justify repeatedly re-visiting the plan

Whatever the precise form, re-trading reflects an unhealthy team dynamic. Interestingly, re-trading rarely takes place within the context of an open setting (i.e. a leadership team meeting), but rather often in 1-on-1 conversations behind closed doors. This is a useless waste of time. It sows the seeds of mistrust (what are they whispering about in there?). It creates factions and unproductive conflict. Even worse, these discussions often spill over beyond the attendees of the original meeting. In this way, leadership team members can dangerously undermine their peers, which completely freaks out the broader team (no one’s happy when the “adults” bring “the kids” into their fight). Needless to say, if these whisper-campaigns gain traction, they can completely derail the original agreed-upon plans. Left unchecked, these side conversations can also have a debilitating long-term effect on future decisions. Specifically, if people believe that they can re-visit decisions after the fact without negative consequences, then they may be incented to simply lay-low during initial debates and surreptitiously seek to get their way later-on. In short, once re-trading becomes normalized, no future decision will ever be safe from the threat of a re-trade.

On the contrary, in his classic book “The Five Dysfunctions of a Team,” Patrick Lencioni offers a succinct description of how truly cohesive teams behave:

1. They trust one another.
2. They engage in unfiltered conflict around ideas.
3. They commit to decisions and plans of action.
4. They hold one another accountable for delivering against those plans.
5. They focus on the achievement of collective results.

Lencioni’s model also offers insights regarding ways to combat the re-trade. As I often say, there is no cure-all for human behavior. But if re-trading blooms in darkness, then sunshine is the best disinfectant. Specifically, pre-emptively calling out the dangers of re-trading goes a long way toward helping teams arm themselves against it. Unlike Voldemort in the Harry Potter series (“He-Who-Shall-Not-Be-Named”), openly acknowledging the potential for re-trading raises people’s awareness of and vigilance against it. Naming and shaming this behavior can give team members language to identify and resist peers’ efforts to engage in after-action 1-on-1 gripe sessions (a central means to waging a re-trading initiative). It also allows leaders to establish criteria for when it is appropriate to re-open past decisions. Specifically, facts and circumstances do change over time. And, if the realities on the ground justify it, then decisions absolutely should be reconsidered by the team. By establishing this as the one reason to re-open prior decisions, leaders can set a high bar for when / how / why plans can openly be re-litigated. Finally, because an ounce of prevention truly is worth a pound of cure, Lencioni’s model offers good guidance on how to address the root cause of re-trading. Maniacal focus on building trust and embracing unfiltered conflict early-on in decision-making processes will always be the best way to avoid downstream re-trading and all its devastating effects.

“So, we’re all in agreement, right? Great, let’s do it.”

As SaaS businesses scale-up, one of the most important responsibilities of an executive is to participate in and support sales efforts to prospective new clients. New client sales are critical to the health of any early SaaS business, and senior executives can play a major role in helping sales teams attract customers. For many leaders, this is an entirely natural act which they execute with ease; for others it can be an uncomfortable stretch. In either case, their involvement needs to balance two competing goals: (1) help win business today that results in successful, profitable, long-standing customers, and (2) build the team’s ability to win more and more of these types of deals in the future. This second goal sometimes gets lost in the shuffle; and it significantly complicates how thoughtful executives engage.

Nearly two decades in SaaS leadership roles have taught me many lessons around an executive’s role in sales meetings (and contributed significantly to my hair-loss early in that period). As I think about those lessons, a majority tend to fall into three general buckets: two “Do’s” and one “Don’t,” as follows:

1. Do…Make the Sales Rep CEO: When a sales professional is working an account, he / she alone is ultimately responsible for the success of that sales cycle. Period. Even in team-selling environments, the rep is on the hook. If she closes a deal, she’ll get the commission and the quota credit. If not, she’ll need to answer hard questions. Regardless of what the company org chart says, she is the team leader in charge of that sales cycle. That person needs to be empowered to get the job done. So, when requested by a sales rep to provide executive representation in a sales setting, I almost always respond that I am happy to, as long as she is willing to assume the role of CEO for that engagement. Said another way, she needs to run the show. I go on to explain that I need her to tell me exactly what is expected of me and specifically how I can support her in successfully closing that particular deal.
   
   This tends to do a number of things. Best case, it empowers the sales professional to dispassionately direct the guest-executive to do precisely what’s needed to win the deal (versus deferring to the executive, who is actually the least knowledgeable person about the account). I love it when a rep gives me painstakingly precise instructions for what value I can bring to a sales process that will help us earn business. At worst, this approach can lead to blank stares. Sometimes a rep hasn’t completely thought through why they want an exec on a call; and this can smoke-out that lack of clarity. I’ve actually had reps tell me, “I’m not sure what I need from you, I just want you to do your CEO thing.” I explain that without context, my schtick just isn’t all that great…and I politely decline the request. In most cases, though, this simple tactic puts the accountability for a successful outcome exactly where it belongs — on the sales professional. Typically, this leads to the salesperson rising to the occasion, using her account knowledge to make the most informed call on meeting strategy, and taking full responsibility for driving a successful outcome. Any action by an executive that leads to this end-result is a must-do.
2. Do…Conduct After-Action Analysis: It goes without saying that relentless pre-meeting preparation is a primary ingredient for successful sales calls, so we’ll skip right over that. What is less common, I’ve found, is prioritizing a ruthlessly candid post-meeting assessment. Immediately after the meeting. Too frequently, people rush off to catch planes or jump onto their next set of scheduled calls. The result is that massive amounts of tacit learning from meetings evaporates forever. Instead, it is well worth the effort to schedule extra time and strictly adhere to the discipline of consistently sharing post-meeting impressions and assessments. These don’t need to be terribly formal, but I like breaking them into two distinct sections. The first is: what happened in the meeting / what went well / what went poorly / what did we learn / what next steps should we consider taking to earn business from this account? This is all about this particular sales cycle, and what we need to consider in pursuit of this specific client. The second is more of a process assessment: how was our preparation / how did our staffing align to the prospect’s participants / how well did our overall messaging work / how was our intra-team interaction / what will we want to replicate with other comparable prospects / what about our approach should we reconsider in the future? This is all about using the data from this meeting as a pure learning opportunity for future application. Separately, I like to start by putting myself directly in the cross-hairs for feedback from the sales rep (aka the CEO for this sales call). “What could I have done differently — please tell me?” To the degree that there are reasonable steps that I can take to better help our salespeople, I really, really want to know what they are. Beyond that, though, I also want the salesperson to know that it is a two-way street, and we should each embrace the opportunity to share our perceptions. I almost always have post-meeting feedback for sales professionals, and / but I first want them to have an opportunity to give me feedback, for the good of the team. This practice can be really unsettling for everyone at first. But I’ve found that it quickly becomes a natural act and a staple among high-performing sales teams that incorporate executives into the selling process. Another “do.”
3. Don’t: Become a Verb: They called it getting “Gibby’d;” and it wasn’t a compliment. I was relatively new in senior leadership roles, having been battle-field promoted within a company experiencing hyper-growth. My unshakable belief in pre-meeting preparation led to a practice where our team of presenters regularly conducted rigorous rehearsals in advance of important sales meetings. Often those practice sessions were the first time I may have heard a particular salesperson present; and sometimes those presentations were pretty flawed. That’s when I’d jump in to “save the day.” I’d start making suggestions about sales strategy, meeting flow, presentation assignments, slide layouts, talk-tracks, competitive positioning, and any number of variables relating to the impending meeting. Generally, these sessions were the night before or the morning of big meetings; and the last thing anyone needed was to have a bunch of late-breaking changes foisted upon them. Although some of these last-minute changes definitely proved to be helpful for a specific meeting / sales cycle, they simply weren’t worth the downstream fallout. Specifically, they undermined the whole effort to empower the sales professional (“no…really, you are the CEO of this sales call…”) and lowered confidence and morale among these critically important team members. In sports, the rule of thumb is never to try something in competition that you haven’t successfully done a number of times in practice. In this scenario, the lesson was not to make any changes that could unsettle a sales professional before a meeting. Conversely, the big learning was to do everything possible to ensure that your sales professionals are feeling their absolute, super-human, bullet-proof best when they walk into sales calls. They’re doing so will allow them to overcome many other imperfections on that particular meeting and build a strong foundation for future sales. To the degree that changes to strategy or tactics are warranted — and they often are — the responsibility of the executive is to ensure that those changes are raised and practiced well in advance of game-day. Lesson learned: Don’t become a verb; just keep your eye on the prize and do the job the salesperson (aka CEO-for-the-day) assigns you.

In closing, executives have a huge role to play in supporting sales efforts as businesses scale; and it can be difficult to balance the desire to help win deals today while building the team’s ability to win consistently in the future. Hopefully these few rules of thumb help leaders land on the stepping stones and avoid some of the stumbling blocks.

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:

• Summary: This is a 1–2 sentence summary that frames up the general work being requested and the broad expectations of what the project will entail.
• Objective: This explains at a granular level how the project and resulting work product will be used within the business.
• Business Goal: This ties the project back to relevant higher-level goals of the company in a way that clarifies for the employee how their work contributes to the greater good of the business.
• Deliverable: This explains in specific terms what the manager is requesting and expecting to be produced or delivered by the team member.
• Format: This gives guidance around what the deliverable might look like and general tools to leverage in completing the task. This can help avoid flagrant swing-and-miss situations where an employee just uses the wrong tool for a given job. I suspect I’m not the only manager who has been surprised by someone using Word, when Excel clearly would have been easier / faster / more accurate / less error-prone…or PowerPoint when something (anything!) else would have been better.
• Sources: This step ensures that the person leverages the breadth of resources available throughout the company. It helps avoid the “dead-in-the-water” problem which keeps someone from getting any traction at all. It also forces employees to think beyond “the Google machine” when contemplating credible, purpose-built resources at their discretion for completing research and other projects.
• Timeline: This is a critical criterion for ensuring that expectations are met and miscommunications are avoided. Established deadlines are also crucial to holding less experienced employees accountable and establishing a foundation of trust among manager and individual contributor. It also helps keep managers honest. Specifically, it protects against the “my manager’s last-minute assignment just blew up my sister’s graduation-weekend” problem (by forcing them to think through workload and the reasonableness of their assignments).
• Opportunities for Creativity: We all want to have a level of autonomy over our work; and much has been written about this dynamic within the modern work-force. The general rule of thumb is for leaders to be clear about “what” they are assigning, but to be far less prescriptive about the “how” one should / could go about executing that assignment. We like to go one step further and explicitly encourage creativity by identifying specifically where a project really could benefit from someone’s innovative thinking. This is NOT intended to limit someone’s creativity or to convey that this identified area is the ONLY place someone is “allowed” inject their own thinking. Rather, it is intended only to remind folks that creativity is good…and to give a nudge of encouragement in one or another particular aspect of a project.

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:

• Application matters: We all want to see our work be put to good use; and this is especially important for entry-level team members. Be sure to tell AND show them (both before and after they complete an assignment) precisely how their hard work will help other stakeholders.
• Feedback is a gift: No matter how busy you may be, remember to take the time to provide feedback (both validating and constructive criticism) on a consistent and timely basis to junior team members regarding their work, and use the template as the foundational document for that discussion — it really helps structure that conversation.
• Balance and honesty are key: It goes without saying that good managers strive to increase the complexity and excitement of the work they assign. That said, it can’t all be fun and interesting; and there will inevitably be dull, tedious tasks to be assigned. When these clunker assignments are unavoidable, don’t try to perfume the pig…just acknowledge this fact and underscore the company’s appreciation to the person tackling the work.

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:

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:

• Transparency vs. Overload: How much information should a CEO share with a board? In some organizations, boards are perceived as external entities “to be managed or handled.” That typically means censoring or tightly controlling the information boards receive, which can really hurt a business. As a first-time CEO, that’s not how I wanted to roll. Instead, I planned to share information freely and be perceived by the board as admirably transparent. So, I became an over-sharer. Specifically, I invested a lot of precious time and energy sending the board gobs of information, a relatively small portion of which was actually useful to them. That board didn’t view me as an open-book. Rather, I had become an incessant and overwhelming stream of data that required resources to be consumed and interpreted. Worse, I was signaling to the board my own inability to call-out the signal from the noise. In this instance, more was definitely not more — it was overload. BOARDS NEED THE RIGHT INFORMATION THAT ALLOWS THEM TO EFFICIENTLY FOCUS ON THE KEY DRIVERS OF THE BUSINESS.
• Pitching vs. Sand-bagging: Smart CEOs recognize that board members (particularly investor-directors) have a lot riding on the success of the company. So, some CEOs fall into the trap of feeling the need to paint a rose-colored picture of company progress. In my experience, board members hate this. They understand that things are never perfect; so, they are inherently suspicious and immediately distrustful of the executive who tries to pitch, promote, or “sell to” the board. My problem was the opposite. I was so intent on being sober and credible (“under-promise and over-deliver,” as the mantra goes), that I consistently under-sold our progress and overemphasized our challenges. This mistake can breed its own forms of mistrust and concern among board-members. Although no one wants to be perceived as a promoter, it’s not much better to be considered a “sandbagger.” BOARDS NEED HEALTHY AND BALANCED EXPOSURE TO THE EXCITING OPPORTUNITIES AND THE INEVITABLE CHALLENGES THAT EVERY BUSINESS FACES.
• Professionalism vs. Perfectionism: We all want to be considered competent and capable, particularly as new executives. So, we attempt to “stick the landing” when it comes to interactions with the board, particularly early-on in our tenures. But while professionalism is a required building block for dealing with boards, perfectionism is a stumbling block to be avoided. In my case, this perfectionist streak was particularly acute with written deliverables such as board packages. They were works of art — high production value slides and zero-defects, prepared weeks in advance of quarterly meetings. And they detracted from time I could have been spending building real value in the business — I was mired on the wrong end of the 80–20 rule when it came to preparing board materials. BOARDS NEED TO KNOW THAT THE CEO IS OVERWHELMINGLY FOCUSED ON DELIVERING TANGIBLE BUSINESS RESULTS; NOT PRETTY PRESENTATIONS.
• Pestering vs. Surprises: CEOs are generally a self-reliant lot, a trait for which we’ve generally been rewarded throughout our lives. The result is that we tend to think we should have all the answers; and we hesitate to ask for help — certainly from our board (“they might think I don’t know what I’m doing!”). In short, we avoid bothering board members with the countless and constant personnel challenges, product-problems, and client-issues that arise in most businesses virtually every week. Instead, we want to show up at quarterly board meetings and reveal a ton of great progress and momentum — like a great chef presenting a masterpiece meal to hungry diners — voila! I’ll admit that I have been prone to this pitfall as a CEO. It’s a particularly insidious one, because this approach works great when everything is going perfectly. Unfortunately, things are never perfect; and negative surprises are about the worst thing a CEO can bring to a board. In other words, the risk simply does not justify the reward. BOARDS NEED TO BE ENGAGED BY CEOs IN A WAY THAT IS CONSISTENT, EFFICIENT, AND JUDICIOUS…NEITHER ONCE EVERY 90 DAYS, NOR IN AN ON-DEMAND MANNER DURING PEAKS AND VALLEYS.

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:

• Get it (G): People either “get it” or they don’t when it comes to their role, the company culture, and the systems that are in place.
• Want it (W): When someone truly likes his or her job and wants to perform that role.
• Capacity to do it (C): Capacity isn’t just about having the knowledge to do the job, but also the time as well as the physical and emotional capacity to do the job well.

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 Google, Amazon, 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.

A 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:

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:

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:

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:

• a. It helps shift the limelight away from you, and onto others who might have more credibility because they are not employees of your company
• b. It helps build stronger relationships with key customers by giving them a chance to shine as part of a panel
• c. It creates a chorus of voices who — without prompting, and without it seeming like you even asked them to — sing your praises in front of a live, studio audience.

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.