Pronouns have been a hot topic for some time (as evident hereherehere, and here). The use of pronouns is an important issue with serious social implications. However, those are not the focus of this post. Rather, this piece more narrowly tackles pronouns in connection to a separate but related topic: the language of leadership. It may seem like a leap, but please bear with me here:

In his amazing work, Language and the Pursuit of Leadership ExcellenceChalmers Brothers makes the case that leaders get paid to have effective conversations. In this TedTalk, he goes on to explain: “Leaders create and continually sustain and cultivate this non-physical, but very real and very powerful thing called corporate culture. Not with tools and fertilizer, of course, but with the conversations they have, the conversations they require, and the conversations they prohibit.” Totally agree…as touched on here in a prior post on this blog. An important part of such conversations revolves around how leaders address or reference themselves and others; and a critical linguistic device for doing so is this thing called a pronoun. Although pronouns tend to be short / small words, they can have an outsized impact on relationships; and this post offers some observations around how pronouns can either support or undermine leaders’ efforts to build culture and deliver results.

Let’s first cover third-person pronouns (he / she / it / they, and related derivatives), since these are the ones that have received by far the most popular attention in recent years. That notwithstanding, third person pronouns are actually NOT the main focus of this post, save for one very important point: effective leaders will take pains to refer to people how they want to be referred. Period. Although this seems like a basic gesture of human respect, it gets botched and not just via presumptive use of traditional pronouns. When multiple teammates share a common name, leaders sometimes innocently call one or many of them by different versions of that name. For this very reason, my father “Rob” was known (annoyingly for him) throughout his entire career as “Bob.” As is the case with an unwelcome pronoun, being called by a name that you don’t like inevitably leads to at least some loss of identity — and lower performance. For this same reason, nicknames in the workplace can be problematic. At one firm early in my career, the name Todd somehow evolved into the nickname “Toddler,” which is how virtually everyone referred to me. I hated it; and it was a contributing factor to my feeling disconnected and disenfranchised at that business. Countless examples abound, and thoughtful leaders work hard to conscientiously refer to people either directly or via third-person pronouns based entirely on their stated preference.

Less obvious to the language of leaders, but arguably even more important, are first-person pronouns (I / we, and derivatives of those). The old saying goes: “There is no ‘I’ in team.” I suppose that is partly true, but with some nuances. Certainly, leaders should avoid taking personal credit for the accomplishments of their organizations. Founders / leaders can create “nails on a chalk-board” moments when they assert things like: “I did $4M in ARR last year,” or “I’m going to deliver ground-breaking new product capabilities in this next sprint.” There is no surer way than appropriating a group’s collective efforts for ego-centric leaders to turn-off their hard-working, under-acknowledged colleagues. Actually, very few stakeholders react well to this habit; we all seem to innately understand the African proverb, “If you want to go fast, go alone; if you want to go far, go together.”

Conversely, the use of the first-person plural pronoun “we” is almost universally appropriate in leadership moments and settings. The term “we” inclusively shares credit and collectively establishes accountability. When in doubt, leaders should consistently default to the term “we” for virtually all stakeholders. This extends beyond a leader’s core team to include customers, prospects, investors, and even competitors. “We” opens a ton of doors, possibilities, and goodwill.

Now…having said all that, strong leaders understand that there actually should be at least one “I” in team — when things go wrong for the organization. When this happens, leaders use the first person singular, as follows:

For effective leaders, there really is an “I” in team…it gets spotlighted when modeling good behavior around embracing vulnerability, adopting a growth mindset, and establishing an environment of accountability…and in encouraging others to do the same.

Finally, the trickiest pronoun of all — second-person (you / you guys / y’all / yinz (when in Pittsburgh), and similar derivatives). When addressing a group, leaders should generally avoid using the word “you,” pretty much…ever. It creates separation from the speaker in a way that is rarely helpful. This is particularly true in a leader’s first 90 days, where using the collective “you” can quickly alienate one’s new team. This may seem innocent enough (“You did this differently in the past than how we’ll approach it going forward.”). But what audiences tend to hear is their leader creating factions within the organization, judging the old-guard, and not yet taking full ownership for the organization as it exists today. This simple slip can sink a new leader before they even get under sail. Even for longer-tenured leaders, I’d contest that the potential costs of using “you” almost always outweigh the benefits. For example:

None of these statements fosters a shared sense of purpose, instead creating an adversarial dynamic. Admittedly, all of the above examples have negative context. Surely “you” can be used in a positive context, such as when praising someone for achieving great results. Right?! I mean…sure, but I’d actually advise against it. Telling someone, “You did a great job,” may sound good on the surface, but it often can be somewhat exclusionary. Specifically, singling out a person (or group of people) runs the risk of undervaluing the countless interdependencies and unseen contributors that are required to achieve any shared goal. This occurred just this week at one of our portfolio companies, in the wake of a successful bookings quarter. One well-meaning exec said to the head of Sales, “Thank you to your team for hitting our bookings number!” Understandably, the head of Marketing, feeling slighted, fumed on the other side of the room. Thankfully, the Sales exec had the good instincts to gracefully point out that it was a team effort across all functions. To emphasize this point, he offered: “Really it’s thanks to all of us; yay for us as a whole…we were only able to beat plan by working together.” Boom! That was an elegant and effective substitution of “we” for “you.”

In closing, like most things, guidelines for the use of pronouns should be followed with a balance of discipline and pragmatism. A bit of attentiveness can go a long way toward avoiding the most egregious or recurring infractions. On the other hand, maniacal adherence to these points can tie leaders in verbal knots, ironically reducing the authenticity and effectiveness of their communications. Leaders should be themselves…and maintain big ambitions for their conversations…but also keep a close eye on those little words, because they / we / you really matter.

The so-called Great Resignation was the topic of a previous post on this blog, and the following piece is a spin-off from that. That prior post focused on employee retention, as have so many recent articles. But we’ve experienced a separate challenge at Lock 8 that also bears discussion — how to get job candidates to actually leave their old company in order to join ours. To be clear, this isn’t a question of how to craft compelling job offers in an historically candidate-friendly market — that’s also rich topic that has been well-covered. Rather, this is about getting candidates who’ve formally accepted offers to actually follow-through on those commitments and show-up for Day 1 in their new company. Seems simple enough, but this challenge is proving to be non-trivial.

Admittedly, there is always risk associated with attractive candidates reconsidering their acceptances of offers, but we’ve seen an explosion of this practice lately. This appears to be yet another employer-focused disruption amid the broader upheaval of the Great Resignation — so much so that we’ve begun internally calling this practice the “Great Renege-ation.” This trend prompted us to consider tactics aimed at ensuring a higher “start-date” yield among accepted offers. Below are a few of the observations, lessons-learned, and things-we’ll-do-differently-next-time:

  1. Ask Hard Questions: It’s common practice to evaluate someone’s “want-to factor” by explicitly asking why they want to land the job we’re trying to fill. Nowadays, we clearly need to go further and also ask (repeatedly) why they are looking in the first place, what is motivating them to consider leaving their current gig, and what it will take to get them to jump? We also need to fight our own long-held biases in assessing responses to such questions. Historically, attractive candidates often already had good jobs and weren’t looking for new ones. But in the upside-down world we now inhabit, that’s problematic. Unless someone is discernably motivated to leave their current situation, the risk is high that they won’t ultimately end up doing so. Why? Because desperate current employers (especially big company ones from which small-scale SaaS businesses often recruit talent) are desperate to keep high-performing team-members. Accordingly, the incumbents have temporary license to throw money at the problem and counter-offer employees with big pay-bumps aimed at convincing them to stay.
  2. Expect a Counter: Given the point above, it’s critical to prepare candidates to expect a counter-offer from their current employer. We’ve found this to be particularly true with more junior professionals, who are surprised and disarmed when their current employer makes a concerted effort to retain them. Our experience is that an ounce of prevention is worth a pound of cure against company counter-offers. Specifically, when employees are forewarned in advance to expect a counter-offer, they are forearmed with how to graciously sidestep them. Alas, if unexpecting employees give oxygen to counter-offer discussions, we as “newco” often find ourselves in a bidding war that we can rarely win.
  3. Recall the Past: As part of preparing candidates to expect a counter-offer from their existing employers, it’s key to remind them what led them to job-seek in the first place. Revisiting responses to the “hard questions” above is certainly fair game. It’s also worth asking candidates where their employer was hiding all of those salary-escalations and title-bumps prior to their having given notice. While these can certainly be delicate conversations, they are often effective when handled deftly. At the very least, they should give job-stayers pause to consider how their career will progress at their current company (particularly a year or so down the line when the labor market inevitably cools a bit).
  4. Sell the Future: It’s also important to ABC (Always Be Closing) by reminding the candidate of the exciting opportunity ahead. The autonomy, breadth of responsibility, opportunity to elevate their role in a smaller organization are often appealing aspects of the move they had been planning. Likewise, key differentiators of the new opportunity include contributing centrally to building a business from an early stage and participating in an options plan that rewards value-creation. For the right candidates, there are few things more enticing than that…but they may need reminders to help them make the leap.
  5. Speed to Close: In an effort to avoid counter-offers entirely, try to not mess around much with the number of days between interviews. It can be worth sacrificing a bit on getting unanimous team buy-in in exchange for moving quickly (we learned this the hard way after losing good candidates by waiting too long to produce an offer. If you see someone you like offer) ASAP…even to the point of closing before candidates leave the interview. It shows they are not in second place and you mean business — like all of us, candidates want to be wanted! At the very least, it is more important than ever to stay connected to the candidate between offer acceptance and start date and eliminate any lulls in communication.
  6. Pre-Boarding Starts Now: Our portfolio companies are having success initiating small scale and lightweight “onboarding” steps even prior to the candidate starting. This starts with the hiring manager keeping an on-going dialogue to monitor the candidate’s tone, level of excitement and reconfirm the resignation process is on track. Quickly this transitions to inviting them to meet their colleagues (e.g.; company or team meeting or virtual happy hour), sharing pre-reading materials and/or casual discussions about ongoings in the business they will have the opportunity to be part of, or even lead.

Bonus Tactic: While most of this piece focuses on closing candidates, it’s worth finishing with a downstream point about the new employee lifecycle. An element of surprise can be really helpful 6 months into someone’s tenure, such as providing an unexpected pay bump or options grant. Getting some re-enforcement that they are doing a good job and surprising them is a nice way to build stickier relationships with newer team members.

It’s a talent arms-race out there…anything we can do to get a leg-up amid the Great Resignation / Great Renege-ation is worth considering in this high-stakes game.

It was 2001; and my boss was impressive — some would say intimidating. A whiz-kid founder and CEO of a fast-growing start-up that had raised capital at lofty valuations, he was precociously business-savvy and had a seemingly unshakable self-confidence. All of which made it that much more remarkable when he put his hands up and uttered those unforgettable words: “You convinced me.”

The truth is that we had very different leadership styles; and I often found myself filing the minority report when it came to debates among our company’s leadership team. But on this day, (and many times thereafter), I was grateful to be offered the opportunity to successfully make my case. I remember being surprised that day about the outcome itself, and about the impact it had on me — I’ll never forget that feeling of having a real voice in the business. Fast forward twenty years: I participate in many similar business debates, but now I often find myself in the senior role. I’ve learned that those same three words have enormous power, not only to make someone’s day…but to profoundly influence how businesses tackle challenges. I try to keep them top of mind and use them whenever possible. Below are some thoughts on why this practice works so well and some safety precautions when wielding this powerful tool.

At a primal level, it’s obvious why this can be such a potent approach — it is a succinct and unambiguous way for leaders to share decision-making authority with less senior folks. Beyond that, though, some subtle nuances make it consistently effective in small-scale growth companies:

Like any powerful instrument, though, using this approach comes with related dangers. Below are a few cautionary thoughts for the safe operation of this tool.

Looking back, I realize how much I learned from that boss back in the early 00’s; and no lesson was more valuable than this one. Having a legitimate forum to change our CEO’s thinking offered a feeling of empowerment that I still haven’t forgotten. And, I was a member of the senior leadership team…which further highlights just how impactful it can be when leaders create this type of environment all throughout their organizations. A big step in this direction can be taken with three simple words: “You convinced me.”

It’s easy for leaders to get caught up in the day-to-day of running small-scale businesses. Particularly during challenging times, it can take all our energy just to “keep the wheels on the bus.” Unfortunately, a casualty of operating in this mode is that we tend to focus far less on the long-term composition of the team — who’s actually on the bus, whether they are in the right seats, and who should be getting on / off at upcoming stops. This is hardly surprising — such planning demands both discipline and foresight. It’s also difficult to get right: organizational design is quite complex, and according to research from McKinsey & Company, less than 25% of organizational redesigns succeed. With that in mind, this post can’t begin to scratch the surface on this rich topic. Rather, it simply introduces a quick-and-dirty exercise to help leaders elevate and think proactively about their organizational “bus” both now and in the future. What follows is a description of the exercise (the “What”), some tips around its execution (the “How”), and some observations about its effectiveness (the “Why”).

The What: The exercise is quite simple and builds upon something that virtually every organization already has available in some format — a current org chart. Using that as a starting point, the leader creates a series of hypothetical future org charts for the business. Specifically, (s)he creates four new / additional org charts, each representing successive six-month intervals into the future. This results in a total of five prospective org charts, essentially five snap-shots that look forward two years, six-month at a time. The five org charts are as follows:

The How: This really is a simple exercise, so there is no need to overthink it. But a few pro-tips can’t hurt; and the following will help make the exercise even easier and more impactful:

The Why: The primary benefit of this exercise is hopefully clear: it is a low-effort way for a leader to plan out with intention and purpose how an organization will grow over time. It works well because it doesn’t require any special skills, resources, or training; and it is something leaders can easily do on their own a couple times of year with a moderate amount of discipline in a short period of time. A few of the side-benefits, and why this exercise works in achieving them, are outlined below:

In closing, this exercise is largely about interdependency between the business outcomes and the people-related aspects of organizations. Leaders generally have a keen sense from a mission and financial perspective of where they want their businesses to be at various points in the future. What we tend to be less good at is identifying and aligning the roles and skillsets necessary to achieve those objectives. Yet, they are completely interdependent — the envisioned goals, and the difficult-to-define team / structure required reach them. This exercise aims to help navigate the organizational side of things. Hopefully, it can help leaders develop a far-seeing view of who should be “on the bus”…and provide everyone a much smoother ride toward the desired destination.

There’s some debate about who first said, “Never waste the opportunity offered by a good crisis.” (N. MachiavelliW. ChurchillR. Emmanuel). Whatever its origin, its meaning is clear: turbulent times lower collective resistance to change and provide a rare opportunity to challenge conventional wisdom. Unsurprisingly, this quote seems to have resurfaced frequently during these recent chaotic weeks; and its sentiment deserves some focused attention as it relates to small-scale software companies.

First things first: it’s hard to think of any crises that are actually “good.” The current COVID-19 pandemic is heartbreakingly awful in countless ways; and this post will not debate that. Neither will it focus on the specifics of the current crisis. Rather, this post is intended to support leaders looking to optimize this moment to bring both stability and positive change to their organizations…and to avoid mistakes that can make a bad situation worse. It does so by building on John Kotter’s 8 Step Process for Leading Change to help ensure that change initiatives are beneficial, successful and long-lasting.

What follows is the officially published “hook” and high-level summary for each of Kotter’s 8 steps for leading change, along with some brief situation-specific commentary from me. Please note: Any text in BOLD ITALICS is the exclusive work of John Kotter and the Kotter organization.

  1. CREATE A SENSE OF URGENCY: Help others see the need for change through a bold, aspirational opportunity statement that communicates the importance of acting immediately. This is all about building and lighting a burning platform for change. This can be hard for leaders to execute without some external force that brings stark clarity to the need for change. But in March / April 2020, global events have created an undeniable and omnipresent sense of urgency which exemplifies the “opportunity” aspect of a crisis. Leaders everywhere are sharing this message with their teams: the world has changed; our business must also change — and fast.
  2. BUILD A GUIDING COALITION: A volunteer army needs a coalition of effective people — born of its own ranks — to guide it, coordinate it, and communicate its activities. This is true for any change management initiative. Enlisting supporters requires a compelling platform for change; but that alone does not guarantee its success in establishing an effective coalition. Leaders need to first identify the most influential people all throughout the organization. This demands an intimate knowledge of the company’s social and psychographic map, which is far more nuanced and complex than simply tapping the top of the official org chart. In SaaS businesses, the guiding coalition may just as likely draw from strong product managers or influential client success representatives as it does from people with VP titles. Equally important, leaders must strike just the right note in order to convince these influential and respected team members to rally behind an initiative (note: even a hint of coercion inevitably backfires!).
  3. FORM A STRATEGIC VISION AND INITIATIVES: Clarify how the future will be different from the past and how you can make that future a reality through initiatives linked directly to the vision. This is the scoping / vision element of the initiative. Critics point out that cynical leaders throughout history have used moments of upheaval to consolidate their power base. Less nefariously but equally misguided, leaders may simply set their sights on the wrong targets for change. Instead, leaders need to carefully think through their change agenda and set a compelling related vision. In times of stability, this can mean launching new products, entering new markets, or setting an aggressive growth agenda. In times of upheaval, however, objectives are often less exciting and sometimes quite painful. They can include cost-cutting, moth-balling non-core projects, or revising commonly accepted company norms. Though the platform may be irrefutably burning, leaders must also remember that the resulting flames can emit unbearable heat for nearby company stakeholders. In all cases, the leader’s vision must be sound, sustainable and undeniably help the organization over the long-term.
  4. ENLIST A VOLUNTEER ARMY: Large-scale change can only occur when massive numbers of people rally around a common opportunity. This step is a major proving ground for change initiatives. If the first three steps have been effective, then a change agenda stands a fighting chance of catching-on, being broadly embraced by the whole company (no matter the size), and collectively implemented. If not, it will stall and likely fail. But there is some good news. Through close monitoring, attentive leaders can identify loss of momentum and take steps to address. We’ve found tools like Poll Everywhere to be a great way to consistently monitor the team’s support for change initiatives; and such feedback can play a critical role in informing a temporary retreat back to steps 1–3 in order to build a stronger foundation for the stages yet to come.
  5. ENABLE ACTION BY REMOVING BARRIERS: Removing barriers such as inefficient processes and hierarchies provides the freedom necessary to work across silos and generate real impact. Senior leaders are uniquely positioned to “make the hard calls” that dissolve resistance to change within organizations. This is particularly true for crisis-related change initiatives. There are natural tensions that exist in software companies across functional departments (e.g. Sales and Client Success or Product Management and Development). Leaders must consider the greater good of the organization, even if it means introducing near-term austerity, ruffling feathers, or introducing other potentially unpopular paths forward.
  6. GENERATE SHORT-TERM WINS: Wins are the molecules of results. They must be recognized, collected and communicated — early and often — to track progress and energize volunteers to persist. This step seems so obvious, but it is deceptively hard to get right. It requires a subtle balance between substance and communication. Results without communication leave the team unmotivated to persevere in their efforts. But over-celebration of results can be perceived as patronizing or insufficiently respectful of the team’s efforts. Moreover, especially when it comes to expense management, touting success too early can undermine the team’s perception of the rationale or necessity for the very changes being celebrated. Be careful not to extinguish the burning platform for change!
  7. SUSTAIN ACCELERATION: Press harder after the first successes. Your increasing credibility can improve systems, structures and policies. Be relentless with initiating change after change until the vision is a reality. Again, this is a balancing act. Change is hard; and it can tax people both physically (e.g. taking on more / harder work with fewer resources) and emotionally (e.g. how long until the reinforcements come?). In week 7 (or is it 8?) of COVID-19 stay-at-home orders, virtually everyone is feeling this. A leader keeping her / his foot on the gas is one thing. But it is quite another when leaders keep layering in more and more unexpected changes in service to the larger vision. In the latter case, team members can feel duped and show the effects of “death by 1,000 cuts.”
  8. INSTITUTE CHANGE: Articulate the connections between the new behaviors and organizational success, making sure they continue until they become strong enough to replace old habits. Changing behaviors takes hard work…and time! Studies show that it takes more than 2 months on average before a new behavior becomes automatic. In other words, leading change demands consistency and commitment from leaders and from the entire organization.

Amid the current crisis, Kotter’s steps for leading change appear as timeless and universally applicable as ever. And they seem particularly valuable for small-scale software businesses, given the existential threats start-ups face and the lightening-quick rate of change in their operating environment. In the midst of the current pandemic / economic crossfire, these steps offer some structure and security for those leaders looking to implement positive change and “make the most” of a decidedly challenging crisis.

In the 1992 legal drama film “A Few Good Men,” Colonel Nathan Jessep (Jack Nicholson) barks an iconic and scathing reproach to Lieutenant Daniel Kaffee (Tom Cruise) and to the world at large, “You can’t handle the truth!”

While this made for an epic movie moment, Colonel Jessep got it wrong when it comes to team members in small-scale software businesses — they can, indeed, handle the truth. Actually, they require it. Highly intelligent and resourceful knowledge workers don’t need a ton from their leaders; but there is a short list of critically important must-haves, particularly in times of crisis. Specifically, they need to know these few things about company leaders:

  1. Do they have an informed understanding of the economic realities and ever-evolving macro-environment?
  2. Do they care deeply about the well-being of company stakeholders (e.g. team-members, customers, partners, etc.)?
  3. Do they tell me the truth? In other words, are they sharing with me the information I need to be able to perform and manage my professional and personal responsibilities?
  4. Do they embrace their own vulnerability, acknowledge that they don’t have all the answers, and actively seek input and feedback?
  5. Do they have a plan for how we move forward?

Like many people, I’ve spent a lot of time in recent weeks trying to get a handle on things by understanding what others are seeing and hearing. As a result, I’ve had the opportunity to speak with many company leaders about what they are experiencing and the nature of communications within their own teams. Particularly interesting to me is how they are choosing to address the harsh and uncertain reality of today’s business climate.

What I observed is that many leaders whom I deeply respect are being quite transparent regarding the challenges their companies face, and about the various options for navigating those challenges. A number of those same leaders expressed pleasant surprise at having received positive feedback following particularly hard-hitting messages to their teams. Intrigued, I researched further and was able to review and compare in varying levels of detail how a number of leaders have been communicating with their teams of late. What emerged from that informal study was a wide range of styles, but also a highly consistent set of practices employed by experienced and effective leaders. These include:

  1. Leaders took great pains to explain aspects of the macro-environment in ways that painted an accurate and easily understandable picture of the widespread economic pain…and then effectively tied it back to how it relates to their own companies at a micro-level.
  2. Leaders expressed clear and heartfelt gratitude for the team’s stalwart efforts amid the current crisis…and for the advantages and strengths the company possesses in the face of such challenges.
  3. Leaders focused explicitly on the company’s unique values as a cornerstone for decision-making…and as a source of strength that will see the company through hard times.
  4. Leaders articulated in detail the financial scenarios and related expense management that they will consider implementing as the situation plays out over time.
  5. Leaders outlined a set of tactics that they will deploy as part of plans to meet whatever challenges come their way.
  6. Leaders acknowledged their own uncertainty about what the coming weeks and months will bring…and they unequivocally opened the door for ongoing discussion. Importantly, they articulated and demonstrated a willingness to listen to their teams always…and particularly during this time.
  7. Leaders strongly encouraged team members to conscientiously prioritize taking care of themselves, their loved ones, and their colleagues.
  8. Leaders reiterated thanks to the team for their commitment to the company, to each other, to their clients, and to the values that bind them.

In sum, small-scale SaaS company teams want a few core behaviors from their leaders; and those don’t include babysitting or happy talk. Quite simply, they want the substantive and relevant truth. But neither do teams desire information overload. They don’t need every little shred of information that impacts the company either positively or negatively on a minute-by-minute basis. They should not be subjected to the turbulence and air-sickness which comes from experiencing first-hand every rise and fall in altitude as the company flies along. That’s a different Tom Cruise movie altogether.

Photo from Top Gun: Maverick — Official Trailer (2020) — Paramount Pictures

Strong communications skills are a must-have for any aspiring executive; and leaders in small-scale SaaS businesses need to be comfortable in a range of messaging situations. In these intimate, dynamic businesses, public speaking represents a major slice of a leader’s communications responsibilities. Executives’ speaking duties can take many forms, with a main one being at trade shows or conferences. At these events, the cardinal rule is knowing one’s audience, as discussed in detail here. But this same rule applies to all speaking situations and all audiences, of which leaders are faced with a broad span. Although this is a seemingly obvious point, it is frequently underestimated and poses a surprisingly tricky hurdle that blocks many leaders’ public speaking efforts. This post examines this issue and offers some simple ideas to help leaders navigate the complex and sometimes intimidating world of speaking to different groups.

To start, I want to refute the widely held notion that public speaking is an innate trait that some of us are born with (or, cursedly, without). While people undoubtedly start with a range of natural abilities, public speaking is an intricate skill that inevitably requires practice and discipline. The more practice, the better one becomes — obviously. But what is less obvious is that the environment in which one practices has a massive influence over how that competence evolves. To make this point, let’s take an example from the world of professional tennis:

Rafael Nadal is one of the world’s all-time great tennis players, having won 35 masters titles in his remarkable career. He has won the French Open a record twelve(!) times, including the recent 2019 crown. Conversely, he has won Wimbledon “only” twice, and not since doing so in 2010 at the age of 24. Why the discrepancy; after all, tennis is tennis, right? As it turns out, Nadal grew up practicing thousands of hours (literally) on the clay courts of his native Mallorca, Spain, which is the same surface on which the French Open is played. He is imminently comfortable on that playing surface, and far less so on the grass courts of Wimbledon’s All England Tennis Club.

Public speaking is very similar: we improve where and how we practice. I don’t mean the physical space (the playing surface is irrelevant here), but rather the types of situations we experience on a regular basis. In my experience, the most important factor in a presenter’s evolution is the kind of audience to which he / she becomes accustomed. This point was driven home recently by an executive with whom I was working. He has vast experience in sales leadership roles and is supremely competent and confident in front of prospects and customers. Having recently moved into more of a general management role, however, he suddenly has far more responsibility for presenting to internal audiences comprised of company-wide team members. He expressed that he finds the experience to be a new and different challenge, to which he is still becoming acclimated. He further shared that he currently requires far more presentation prep and notes in order to feel ready to present to this group. Given his background, this makes total sense; and it raised for me the following related observations.

A large part of leading SaaS businesses revolves around balancing the needs of different stakeholders, as referenced here and more briefly here. I often think in terms of a company’s four key sets of stakeholders: (1) its addressable market, (2) existing clients, (3) company team members, and (4) shareholders or owners. In the context of public speaking, it is helpful to think about these stakeholder groups and simply bear in mind the uniqueness of each as an audience. If nothing else, doing so can raise a presenter’s awareness around which audience represents a personal comfort versus one that may fall further outside his / her comfort zone. This alone can lead to more thoughtful and effective prep.

For some presenters, it can be helpful to overlay the concept of “altitude” on this stakeholder framework. Specifically, we often use the term “altitude” to describe the appropriate level of detail for a discussion or presentation. As a general guideline, each stakeholder group tends to have a different preferred altitude, or level of detail, at which they want to be engaged. This might look something like this:

  1. Shareholders (highest altitude, least appetite for day-to-day details)
  2. Prospects (somewhere in the middle / top)
  3. Clients (somewhere in the middle / bottom)
  4. Team members (lowest altitude, most day-to-day details)

Taking this concept further, presenters can further identify the general / typical information needs of each different stakeholder group. This might look roughly as follows:

  1. Shareholders: Company financial performance in the recent past, the present, and the foreseeable future…and any items that could materially impact that performance.
  2. Prospects: Product and services information to inform a purchase decision that should prove over time to have been a wise, positive-ROI investment.
  3. Clients: Evidence to inform an ongoing renewal of commercial decision (i.e. will the “pain of change” (hopefully) far out-weight the “pain of same” in the vendor-client relationship).
  4. Team members: Do I have the necessary resources to successfully do my job today; does this continue to be the right company for me to achieve my career and professional goals?

Finally, it’s also worth noting that the each of these stakeholder groups is comprised of a rich and diverse set of sub-groups. For example, within a group of team members, the needs and perspectives of software developers will be different from those of salespeople or marketers. Likewise, in the shareholder category, existing owners who are current board members will have a very different viewpoint than prospective new investors. Further segmenting each stakeholder group can only help a public speaker to mindfully target content and delivery style to match the audience needs.

To finish at the beginning, public speaking is a critical tool in a business leaders’ toolbox. Knowing one’s audience is paramount across a wide spectrum of prospective speaking situations. And this framework can hopefully be helpful in making it easier for thoughtful leaders to prepare effectively and present expertly in any situation.

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.

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.

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.

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