A CEO asked me about the most common mistakes made by my clients, most of whom are also CEOs. I had to consider how my clients would answer that question, and I think the overarching theme would be: They waited too long. They waited too long to establish sufficient structure in the culture's routines. [1]
Overview
Most of my clients are leading their company through a period of rapid growth and dynamic change, and a common theme in our work together is what I think of as "the judicious imposition of structure." As an organization scales and its operations grow more complex, it requires an increasing degree of structure to coordinate activities and achieve goals across ever-larger numbers of employees and customers, locations and time zones, products and services.
The structure that meets the needs of the founders will be insufficient for the first employees, the structure that meets the needs of a small team will be insufficient for a larger one, and so on. When an organization outgrows its structure, inefficiencies are created. It's unclear who's responsible for what, or how certain tasks are accomplished or decisions get made, resulting in overlap, confusion and conflict.
But the converse is equally true: The structure that meets the needs of a large organization will be excessive for a smaller one. What allows a mature organization to operate at scale will feel like stifling bureaucracy to an early-stage company still subject to radical change. When too much structure is imposed too soon, gaps emerge. Innovation is sacrificed in the name of expediency, and opportunities are lost.
It's essential for a leader to anticipate the organization's evolving needs and impose new types and degrees of structure as necessary, and the right timing is crucial. It's problematic to be too early or too late, but in my experience leaders typically delay imposing structure until it's obvious that they've fallen behind and need to catch up. In part this is because founders are like pirates, as Reid Hoffman has noted, who "lack formal processes, and are willing to question and even break rules." [2] These characteristics have enabled them to nimbly outflank established incumbents, but they can also contribute to a preference for informality even when it no longer serves them.
As a result, much of my work with clients in this realm involves examining inefficiencies, considering where and how more structure might yield greater clarity, and running experiments to test these hypotheses. These efforts are pursued on multiple levels: organizational (involving formal roles and assignments), interpersonal (involving group norms and working relationships), and individual (involving the leader's environment and working life). The three topics below are by no means a comprehensive list, but they provide opportunities to explore "the judicious imposition of structure" at each level, and all of them show up repeatedly in my practice: The Executive Team, Meeting Hygiene & One-on-Ones, and The Leader's Calendar.
Part 1: The Executive Team
When a company is founded, calling a group of people the "executive team" (or some similar designation) is superfluous and even counter-productive. Early-stage employees are attracted by the prospect of working directly for a founder, and founders want to be as close as possible to the work those early-stage employees are doing. An intermediate layer of management between the CEO and other employees at this stage serves no purpose except to reward status-seekers.
Further, it can be risky for an early-stage employee to be "over-titled," claiming a C-level or VP position by virtue of the fact that they report to the CEO when they lack the experience and capabilities usually associated with such titles. It's possible that at a later stage the CEO will need to award one of these titles to land a senior candidate who does have the requisite experience and capabilities. If an early-stage employee has a more ambiguous title, it's possible to level them while still retaining them, but when a title is taken away it's rare to retain the person from whom it was taken. [3]
Even after the first layers of management have become necessary, it's often still the case that key employees have information that leaders require in order to make decisions, and the systems necessary to provide that information in the employees' absence haven't yet been created or are technically infeasible. For all of these reasons it's common for early-stage CEOs to defer establishing a clearly-defined executive team with a fixed membership--and yet in my experience a number of factors eventually make it necessary.
The effort required to provide truly thoughtful one-on-one management to employees leads most CEOs to decrease their number of direct reports over time. In part this is because as an organization grows and the people reporting to the CEO become more senior, the CEO provides less direction and more coaching and other forms of support, which can be more time-intensive, not less. Senior leaders are hard to replace, so the CEO needs to remain abreast of (and actively influence) their commitment to the role, which requires a close understanding of each individual's sources of motivation and fulfillment. The formalization of an executive team helps the CEO focus their managerial attention on a smaller number of people and have a greater impact in the process.
But this form of structure benefits the members of the team not only through their relationships with the CEO, but also through the establishment of a coherent group identity and their relationships with each other. The informal assembly of senior employees that predates a formal executive team lacks an identity--it probably doesn't even have a name--and its membership is fluid and heterogeneous. This renders it more flexible, but it also inhibits the development of psychological safety. Note that a safe environment doesn't mean people are "nice" or indirect--it means that people feel free to speak their minds and that vigorous disagreements can take place without undue distress. [4]
The formal structure of a clearly-defined executive team can enhance psychological safety in several ways. Even when the team includes a range of titles (e.g. C-levels, SVPs/EVPs, VPs), membership confers a shared status, and repeated interactions among members render team discussions more predictable, factors that make interpersonal conflict less likely and easier to manage when it occurs. [5] And the "mere exposure effect" causes people to feel a greater sense of affinity for each other with regular contact. [6] Note that none of this implies that formal executive teams are more harmonious than informal leadership groups--they may well be more fractious, because the members feel safer and thus more comfortable openly disagreeing with each others. [7]
To obtain the benefits of this structure, the CEO usually has to level one more more direct reports or exclude employees who were previously members of the informal leadership body. This has predictable effects on those individuals--as I've noted before, there's an "intense desire on the part of everyone just outside that circle to be included." [8] As a result, the establishment of a smaller executive team is often accompanied by another form of structure: a larger management body with a defined membership that ensures that those who have been excluded still feel included in some way.
This need not be a cynical exercise in organizational theater, although it can certainly become one. While the formal executive team is typically more efficient than the informal group that preceded it, that efficiency can come at a cost, such as blind spots or groupthink. [9] A larger management body provides a venue for information-sharing that affords the executive team more visibility into activities outside their immediate purview as long as the group's norms promote active participation and dissent--which depends on yet another type of structure, an organization's meeting hygiene.
Part 2: Meeting Hygiene & One-on-Ones
In the very first stages of a new venture's formation, the idea of a "meeting" is comical. Given the small number of people involved, the ease with which information is shared, and the vast number of existential threats there's no need for a gathering in which people discuss work rather than do work. Everyone's too busy doing things to stop working and meet. This period ends sooner than many founders realize (or would prefer), and meetings eventually become necessary forums for information-sharing, decision-making, and other purposes.
In the absence of a shared agreement regarding how to meet most effectively, organizations simply conduct meetings in accordance with the norms that have emerged as features of the culture. [10]. But as an organization grows it becomes increasingly important to have clearly articulated and commonly understood answers to such questions as:
- What's the agenda and who sets it (and how long in advance should it be distributed?)
- Who's attending (and who's not)?
- How timely are we (and what's considered late)?
- How prepared should we be? How do we communicate with each other most effectively?
- And when will we meet again?
But note that these forms of structure at the group level can be easy to identify and very difficult to implement. As I've written before,
You've probably worked as a group to identify some "ground rules" to improve the quality of your meetings...but despite these efforts, your meetings haven't really improved. One reason why is the difference between "rules"--which are what we intend to do, or what we're supposed to do, and "norms," which are what we actually do... Rules on their own are often fairly weak, while norms are much more powerful--and often exert significant influence in the absence of any formal rules, for better and for worse. [11]
A particularly important type of meeting is the one-on-one between a CEO and a direct report. Early in an organization's development it may seem unnecessary to hold regularly scheduled one-on-ones, and in some settings this attitude persists well into maturity. Intel CEO Andy Grove noted that managers from other companies usually declared the practice unnecessary, telling him, "Oh no, I don't need scheduled meetings with my supervisor [or subordinate]; I see him [sic] several times a day..." However, Grove continued, "there is an enormous difference between a casual encounter by a supervisor and subordinate, or even a meeting to resolve a specific problem, and a one-on-one." [12]
But even though the practice of managerial one-on-ones is now widely endorsed, it's not uncommon for leaders to defer formalizing them for the same reason cited by Grove's contemporaries--they talk to their employees regularly. And yet in the absence of this structure, a host of inefficiencies emerge: Immediate tactical concerns predominate in sporadic, informal interactions while more complex, more personal, or longer-term issues come up rarely, until a crisis makes such a discussion unavoidable. Time and effort are wasted as both parties determine when and how to meet, a problem compounded when the absence of a more meaningful agenda leads one or both parties to reschedule or prioritize other tasks.
Good meeting hygiene at the one-on-one level addresses these issues, while also answering the questions above--and it's generally easier to get two people to revamp their norms provided the leader acts consistently. It's also more feasible to suggest a set of best practices to provide structure for one-on-ones than for group meetings. The diverse nature of groups and their varying requirements leads me to be skeptical of blanket prescriptions, but for one-on-ones I look to Grove's High Output Management. Written in 1983, it remains unsurpassed as a guide to effective one-on-ones, although I've updated the gendered language of that era to make Grove's otherwise outstanding advice more inclusive:
How often should you have one-on-ones? Or put another way, how do you decide how often somebody needs such a meeting. The answer is in the job- or task-relevant maturity of each of your subordinates. In other words, how much experience does a given subordinate have with the specific task at hand? This is not the same as the experience they have in general or how old they are...
How long should a one-on-one meeting last? There really is no answer to this, but the subordinate should feel that there is enough time to broach and get into thorny issues... I feel that a one-on-one should last an hour at a minimum. Anything less, in my experience, tends to make the subordinate confine themselves to simple things that can be handled quickly...
What should be covered in a one-on-one?... The most important criterion governing matters to be talked about is that they be issues that preoccupy and nag the subordinate...
What is the role of the supervisor in a one-on-one? They should facilitate the subordinate's expression of what's going on and what's bothering them. The supervisor is there to learn and to coach... How is this done? By applying Grove's Principle of Dialectic Management, "Ask one more question!" When the supervisor thinks the subordinate has said all they want to say about a subject, [the supervisor] should ask another question...
A key point about a one-on-one: It should be regarded as the subordinate's meeting, with its agenda and tone set by them... So the [subordinate] should be asked to prepare an outline, which is very important because it forces them to think through in advance all of the issues and points they plan to raise. [13, emphasis mine]
Just as with the formalization of the executive team, more structured one-on-ones enhance psychological safety through predictability, repeated interaction, and a boost to the status of the subordinate, which create more room for vulnerability and emotional intimacy. These topics were of keen interest to Grove, the tough-minded engineer known for his rigorous management style:
The supervisor should also encourage the discussion of heart-to-heart issues during one-on-ones, because this is the perfect forum for getting at subtle and deep work-related problems affecting their subordinate. Does some frustration or obstacle gnaw at them? Do they have doubts about where they are going? [14]
And a leader's ability to implement any of these ideas at the group level or in one-on-ones rests on a commitment to employ their calendar as a tool to set and maintain priorities and focus their attention accordingly.
Part 3: The Leader's Calendar
As noted above, founders and other early-stage leaders often have an aversion to formal processes and rules--this inclination may have led them to launch or join a new venture in the first place. In my experience this translates into prioritizing responsiveness and flexibility over predictability and routine, as well as an opportunistic approach to calendar management. And up to a certain point this serves not only the leader's personal preferences, but also the overall needs of the organization. Envisioned products and services, prospective markets and customers, and the business model that animates the entire enterprise are all highly speculative and subject to change. The early-stage leader has to respond rapidly to new information, which often involves sudden changes in priorities, and in this context a dynamic calendar is a survival tool.
But the organization's needs change with continued growth and increasing complexity, and the leader's utilization of their time--and, more importantly, their attention--must evolve accordingly. As I've written before,
In the first few months (and sometimes years) after launching the company...every task and issue seems important, there aren't many other people to delegate to, and it seems perilous to ignore things. Existential threats abound, and [the leader feels] responsible for addressing almost every possible claim on their attention if the business is to survive... [Later] it becomes easier to identify the tasks and issues that truly merit their attention, there are teammates in place to handle work that can be delegated, and it's now perilous not to ignore things. [15]
And note that ignore doesn't mean deprioritize or defer, another concept I've discussed previously:
After we prioritize, we act as though everything merits our time and attention, and we’ll get to the less-important items "later." But later never really arrives. The list remains without end. Our time and attention are finite resources, and once we reach a certain level of responsibility in our professional lives, we can never fulfill all the demands we face no matter how long and hard we work...
The key is recognizing that prioritization is necessary but insufficient. The critical next step is triage. Medical staff in a crisis must decide who requires immediate assistance, who can wait, who doesn’t need help at all, and who’s past saving. Triage for the rest of us entails not just focusing on the items that are most important and deferring those that are less important until "later," but actively ignoring the vast number of items whose importance falls below a certain threshold. [16]
Note my emphasis here on the leader's attention, which eventually becomes the scarce resource--far scarcer than capital--and which I distinguish from time. A leader can spend a great deal of time on something to minimal effect when when they're distracted, but when their attention is focused it can take very little time to have an impact. [17] And because the leader's focused attention is so valuable, other people are eager to claim it. They want access to the leader because they know the leader's attention has the potential to help them achieve their goals. They want the leader in the meeting because that makes it a more consequential event. They want the leader's feedback on their ideas and performance in order to validate both. And they're rarely concerned with the cost to the leader. Very few people will stop to ask whether their personal priorities truly merit the leader's attention, in part because we habitually fail to "empathize up." [18]
In addition to the increasing complexity of the business, many leaders experience a parallel increase in demands for their attention in their personal lives. A romantic relationship becomes more serious, or a serious relationship leads to marriage. Children are born, become toddlers, enter school, and go off to college. Parents age and require more care and support. And leaders themselves grow older and realize they need to attend more closely to their own health and well-being.
For all these reasons, I find that leaders ultimately benefit when they begin to (judiciously) impose structure on their calendar. What does this entail in practice?
- Distinguish between importance and urgency. They're not the same. Tasks and issues are often urgent because they're important to someone else, but the leader who treats their attention as a resource is careful not to allow other people's priorities to set their agenda. [19]
- Dedicate time for "important-but-not-urgent" activities. This includes one-on-ones with direct reports, regularly occurring blocks of "open space" [20] for strategic thinking [21], and self-care practices such as sleep, exercise [22], and mindfulness [23].
- Establish and maintain necessary boundaries. The leaders I've known are usually "happy workaholics," and they're not seeking "life/work balance." But using their calendar to set boundaries--and honoring those commitments--enables them to allocate the right amount of time across competing demands. [24]
- Get help--because a leader can't do this alone. Early-stage leaders are often reluctant to hire support staff, but an executive assistant [25] or Chief of Staff [26] can be a tremendous source of leverage by helping the leader direct their attention toward their most important priorities and away from distractions.
To be clear, there's no "time management hack" here that will magically resolve a busy leader's challenges. But the leader who can impose an increasing degree of structure on their calendar will find themselves better able to focus on their most important tasks and less anxious about ignoring everything else, which makes it immensely easier to step away from work when necessary. Successful leadership at scale obviously requires hard work, but it's less about the leader's individual output and more about their interpersonal influence--their ability to show up in every interaction as a persuasive and compelling presence. Leaders at scale are always under a spotlight, which can be exhausting. [27] A structured calendar allows the leader to replenish themselves on a regular basis, whether it's a brief break between video calls, an evening with family free from distractions, or a lengthy trip to clear their minds and dream big dreams. And those aren't indulgences, they're investments. [28]
Footnotes
[1] Don't Wait
[2] Uber Needs to Transition from "Pirate" to "Navy" (Reid Hoffman, LinkedIn, 2017)
- For further thoughts on Hoffman's metaphor, see Pirates in the Navy.
Part 1: The Executive Team
[4] For more on psychological safety, see the work of Harvard Business School professor Amy Edmondson:
- Make Your Employees Feel Psychologically Safe (Martha Lagace interviewing Amy Edmondson, Harvard Business School Working Knowledge, 2018)
-
How Fearless Organizations Succeed (strategy+business, 2018, excerpted from Edmondson's book below)
-
Building a psychologically safe workplace [11:26 video] (TEDxHGSE, 2014)
[5] How Leaders Create Safety and Danger
[6] Exposure effects in the classroom: The development of affinity among students (Richard Moreland and Scott Beach, Journal of Experimental Social Psychology, 1992)
[7] How Management Teams Can Have a Good Fight (Kathleen Eisenhardt, Jean Kahwajy and L.J. Bourgeois III, Harvard Business Review, 1997):
Without conflict, groups lose their effectiveness. Managers often become withdrawn and only superficially harmonious. Indeed, we found that the alternative to conflict is usually not agreement but apathy and disengagement. Teams unable to foster substantive conflict ultimately achieve, on average, lower performance. Among the companies that we observed, low-conflict teams tended to forget to consider key issues or were simply unaware of important aspects of their strategic situation. They missed opportunities to question falsely limiting assumptions or to generate significantly different alternatives. Not surprisingly, their actions were often easy for competitors to anticipate.
[8] Role Clarity and Role Confusion
[9] Much of the original work on groupthink by psychologist Irving Janis in the 1970s has been rejected for being insufficiently predictive, but the overall concept clearly remains valid even as we seek to better understand its mechanism. For more, see So Right It's Wrong: Groupthink and the Ubiquitous Nature of Polarized Group Decision-Making (Robert Baron, Advances in Experimental Social Psychology, 2005):
Janis’s probing and insightful analysis of historical decision making was correct about the symptoms of groupthink and their relationship to such outcomes as the suppression of dissent, polarization of attitude, and poor decision quality and yet wrong about the antecedent conditions he specified. I contend that not only are these conditions not necessary to provoke the symptoms of groupthink but that they often will not even amplify such symptoms given the high likelihood that such symptoms will develop in the complete absence of intense cohesion, crisis, group insulation, and so on. [page 228]
Part 2: Meeting Hygiene & One-on-Ones
[10] Joel Peterson on Organizational Culture:
I asked him about culture, and he said, "We don't have any culture in our business." Well, you have a culture. When you've decided you don't have a culture, you've got one. The question is: Do you want to influence it or not?
[11] Rules Aren't Norms (On Better Meeting Hygiene)
[12] High Output Management, page 73 (Andy Grove, 1983)
[13] Ibid, pages 73-76
[14] Ibid, page 77
Part 3: The Leader's Calendar
[15] Early-Stage Survival and Later-Stage Success
[16] The Most Productive People Know Who to Ignore
[17] The Art of Self-Coaching: Attention (Stanford GSB Class of 2016 Reunion)
[18] The Difficulty of Empathizing Up
[20] Open Space, Deep Work, and Self-Care
[21] How to Think (More on Open Space and Deep Work)
[22] Get Moving! (Exercise for Busy People)
[23] Don't Just Do Something, Sit There! (Mindfulness for Busy People)
[24] Happy Workaholics Need Boundaries, Not Balance
[25] Three Stages of Executive Assistance
[26] Hail to the Chief (of Staff)
[27] Watch That Next Step (CEO Problems)
[28] Investments, Not Indulgences
Photo via PxHere.
