This page is a work in progress, part of a multi-year effort to capture and share learnings, frameworks, tools, and processes to run organizations. See Running Organizations for more.

When to Hire Managers

Managers are the frontline and middle managers needed to serve an organization that has outgrown a "hub and spoke" CEO/Leadership Team model.

This page is not about when to hire a CFO or whether you should have a marketer in the C-Suite (CMO) or an operator/COO. Those questions are highly context-dependent. Assuming you have a Leadership Team that forms a solid foundation, what I’m talking about here is the managers you need to staff within departments.

Hire Functional Leaders First

Functional leaders should be hired first, whenever possible. Functional leaders are the Directors and VPs who are experts in their functions. These leaders have the expertise to effectively hire, train and mentor people, including middle managers. Due to their expertise, they'll handle the job responsibilities more effectively than a CEO or COO.

Are People Getting Individual Attention?

Are frontline team members slipping through the cracks or feeling isolated? How are your employee retention rate and Glassdoor Reviews? When people in a growing organization get lost in the reporting structure, what breaks out is dysfunction. People feel isolated, they perceive unfairness or struggle to cope with the chaos, and they find others in the organization who feel the same way, ultimately creating toxicity.

Before you get here, promote internally or hire from the outside to staff managers who can mentor, train, coach, and connect frontline team members.

Before You Reach 50 Heads

A team of 15 can be managed by an energetic CEO. People can mostly self-manage, or the CEO can dictate a lot of the day-to-day activity. Most organizations at this size will have other Leadership help - whether it's a COO/President, or a functional Director or two. As functions are built out, Directors begin to feel stretched and struggle to take on new initiatives without the help of additional Managers. This is the time to start to build out middle management.

One key issue at < 50 employees is that it's not possible (or a good idea) to staff an entire management team. Instead of frontline staff "wearing many hats" as it goes in early-stage companies, when you get to a few dozen employees it's often Managers who are managing a ton of people and running around putting fires out.

After 50 employees, and certainly before 100, organizations can afford to build out a complete management team. This is the stage where the first sensible org chart is complete.

What Do Managers Do?

Managers Serve

Managers are there to support the work and the people doing it. Managers don't "control" the work. Managers serve the business as the "internal suppliers" of the organization.

"Managers supply definition, meaning, direction, focus, plans, priorities, communication, equipment, material, methods of work, smooth flow, continuity, moral support, and a good working environment to the organization's employees." - Peter Scholtes (Source: The Leader's Handbook)

Managers bring clarity and guidance where it's lacking. They keep employees engaged and motivated and growing as people.

"Gallup research shows that 70% of the variance in employee engagement scores is attributable to managers and how effectively they guide their teams. Given the relationship between worker engagement and crucial business outcomes - such as productivity, profitability and customer perceptions of service quality - managers and their teams hold the keys to organizational health." (Source: The Matrix: Teams Are Gaining Greater Power in Companies)

Managers Bring Energy, Discipline, Focus

Management succeeds when it brings energy, operational discipline, and accountability to organizations. While mission, vision, and strategy need to be made accessible to everyone in the organization, how those components translate into action is the job of management.

The action itself, though, is the arena of the people who report to Managers, and that's why Management should be focused on creating enthusiasm and focus on the front lines.

"Management's essential role is to elicit the energy, discipline and focus that it takes to overcome short-term temptations and win by getting more done (and done better) than others do." - David Maister (Source: Strategy And The Fat Smoker)

Enthusiasm and focus come down to leadership. Management is not about monitoring or “supervising” people, or controlling people, but inspiring people to want to achieve.

"A real leader can somehow get us to do certain things that deep down we think are good and want to be able to do but usually can't get ourselves to do on our own... You almost always like how a real leader makes you feel, the way you find yourself working harder and pushing yourself and thinking in ways you couldn't ever get to on your own." - David Foster Wallace

Managers Create Change

Managers Implement Change

In a constantly changing world, our organizations need to be constantly changing. How they change is ultimately decided by Leadership Teams, but the specifics of change are always an interplay between Management and staff.

The specifics can't or shouldn't be dictated by the top team, as the leaders at the top cannot stay on top of the details of every function. Functional managers have the strongest sense of what needs to be done, and how to get it done through their Direct Reports.

"People at the bottom of the hierarchy just don't have the perspective to reinvent, nor do they have the power to carry out any reinvention scheme. If reinvention doesn't happen at the top and it doesn't happen at the bottom, there is only one possibility remaining: It's got to happen in the middle." - Tom DeMarco (Source: Slack)

Change initiatives are a large part of the "implementation" work that managers take on. If you want to improve culture, improve the system, or change key processes, you need management to move the mass of individuals to change, often one by one.

Management In Change Efforts

If you want to create change at scale, and you don't have a management team that can work with individuals one by one, it won't happen.

If you do have a fully-staffed management team, but they're not committed to the vision, it won't happen. Having a management group that is fully staffed and committed to change is how you create organizational and cultural change.

What Good Managers Do

Know Their People

Managers have to know their people to be able to do a good job. A good test of any manager is if they can describe their direct reports in detail - their strengths and weaknesses, learning edges, their personality, and what they've accomplished.

Knowing people requires working with them, communicating with them, and spending time with them. For managers, it might also mean talking to others to triangulate information and generate more well-rounded perspectives.

Some highly-perceptive and emotionally intelligent managers just "get people." For others, it simply takes time and relationship-building. For that reason, frequently switching out managers and changing manager relationships (i.e. reorganizing) is highly disruptive.

Make Clear Objectives & KPIs

Good Managers are clear with their Direct Reports about the vision of the organization and the mission of the Function. They create and communicate clear team and function Objectives and the KPIs that predict performance. If managers are not clear on these fundamental areas, their direct reports are unlikely to know how to be productive in their roles.

Managers should be heavily involved in the creation of Rocks/OKRs and their follow-through (accountability to completion). They should also define and help their teams define appropriate KPIs to understand whether performance is on track or not.

Delegate The Right Kinds of Work

Managers don't "do the work" and don't bail people out of doing the work by doing it for them. Good managers push their direct reports to grow. They know how to design "stretch assignments" that facilitate the growth of their people.

Good managers have a sense of what kind of tasks and projects are appropriate for their direct reports, and what kind of work they should do themselves. They allow their direct reports to fail in small ways and provide a safety net for mission-critical tasks they've delegated.

"The right level of delegation is a balancing act. It depends on a team's maturity level and the impact of its decisions. Distributed control in an organization is achieved when delegation of authority is pushed as far as possible into the system. However, circumstances may require that you start by telling or selling, gradually increasing the delegation level of team members and widening their territories." - Jurgen Appelo (Source: Managing For Happiness)

For more on Delegation, see Deciding & Delegating.

Ensure That People Are Trained

Managers train inexperienced talent and help onboard new talent into the organization. They train on processes, procedures, and the basics of succeeding in a given job function. They don't necessarily do all of an employee's training, but they are accountable for ensuring that their people are trained.

Managers also train on newly-created processes and procedures, which include socializing change. They make sure everyone is capable of performing the new way when processes are changed.

Training done by managers is often more effective than training done from the outside for two reasons. One reason is that Managers can impart implicit knowledge, color, and cultural understanding by providing commentary as they train. The second reason is that the act of Managers spending time on training shows the talent that the organization backs the training and is committed to them being effective in their role.

Coaching & Mentoring

Managers who focus on Mentoring and Coaching their Direct Reports to improve their performance are, in my experience, some of the best Managers most people have ever had at work.

Leverage Their Experience to Mentor

Mentorship is giving Direct Reports answers to their questions and solutions to their problems. Managers mentor talent by providing "in my experience" advice and help.

"Each time a manager imparts his knowledge, skills or values to a group his leverage is high." - Andy Grove (Source: High Output Management)

While training gives people the explicit knowledge and understanding to be able to solve simple and straightforward problems, we all run into complex and chaotic problems that are dependent on context. In those situations, Managers who have "been there" can guide their direct reports toward the best solutions.

Coach By Asking Questions

Coaching is a process of using questions to teach people to think for themselves and solve their own problems. Coaching builds responsibility and autonomy in the organization. Coaching builds respectful and meaningful relationships between people and should be a default tool for managers.

"Good coaches tell you where the fish are, great coaches teach you how to find them." - Kobe Bryant (Source: The Mamba Mentality)

While mentorship gives answers and approaches when a direct report is lacking direction, coaching is about building a direct report's ability to help themself. Good managers know that they can't change people and they can't force people to grow.

"The feedback they provide to themselves is going to be the real driver of any lasting change. And that's why a coach is primarily a questioner and not a source of feedback (as an adviser or a mentor might be.)" - Ed Batista (Source: Gestalt Coaching)

Sir John Whitmore's GROW Model is the simplest tool for coaching because it follows an easy formula and can be done by nearly anyone, not just managers. It’s as simple as “What do you want?” (Goal), “Where are you now?” (Reality), “What could you do?” (Options), and “What will you do?” (Will).

Feedback

Feedback serves as a mirror that helps people become more self-aware. The purpose of feedback is to help the person receiving the feedback improve. If feedback doesn't help people grow, it's a waste of time. Part of judging whether feedback might help a person grow is whether they're willing to hear it, and that has a lot to do with whether the manager-direct report relationship is strong enough. This is where "knowing their people" is extremely important.

Managers must be able and willing to deliver both positive feedback and critical feedback.

Giving Positive Feedback

Positive Feedback is praise, recognition and appreciation. Positive feedback builds motivation and good vibes. Managers shouldn't need a special reason to give positive feedback as long as they're paying attention to the Direct Reports' work.

The best kind of positive feedback resonates with us and teaches us something about the way we are viewed at work or shows us that we’re capable of more.

Giving Critical Feedback

Critical Feedback helps people grow more than positive feedback because it tells them how to improve. Unlike positive feedback, which can be sourced from all over your organization, only certain cultures enable meaningful critical feedback from people other than managers. If managers don't give critical feedback to direct reports, the organization doesn't get improved performance.

One issue with withholding critical feedback when it needs to be delivered is that over time, managers start to resent their direct reports.

“For every piece of subpar work you accept, for every missed deadline you let slip, you begin to feel resentment and then anger. You no longer just think the work is bad: you think the person is bad. This makes it harder to have an even-keeled conversation. You start to avoid talking to the person at all.” - Kim Scott (Source: Radical Candor)

Easy Feedback Formulas

Situation, Behavior, Impact is the most simple feedback model I've come across. It can be used for positive and critical feedback.

Another model for feedback is Start, Stop, Continue. You can use this in team settings and meetings of all kinds. It ensures that you can give specific positive AND critical feedback without delivering the infamous "shit sandwich."

Feedback is personal. There's no way around that. It's not "just business." Our work is a representation of who we are. Good managers take both positive and critical feedback seriously.

One-On-Ones (1:1s)

1:1s build the relationship between the Manager and Direct Report and help the Direct Report get unblocked. They are NOT the Manager's meeting, and the agenda is not the Manager's. The 1:1 is a shared meeting, with a shared agenda.

Never Cancel a 1:1

1:1s must be held weekly. Two weeks is too long - too much happens in two weeks. Keep them on the calendar. Don't try to "find a time" every week - it won't happen. Thirty minutes is plenty. If you need more time to work on something, create a separate meeting.

It's OK to miss a 1:1 every once in a while, but only at the direct report’s discretion. Keeping 1:1s is the best tool the Manager has for building and growing the relationship. When a manager cancels a 1:1, they send the message that direct report isn’t worth their time.

1:1 Practices

Managers hold hierarchical power over their direct reports, so 1:1 is not the appropriate arena for the manager to exercise power. If the Manager steamrolls a 1:1, the 1:1 becomes a "manager meeting" instead of a relationship-building meeting.

Managers should take notes in 1:1s. Managers can't assume they'll remember one month from now what all seven of their direct reports said this week. Notetaking shows the Direct Report that what they say and think, matters.

Some 1:1s will be highly impactful and some will feel unproductive for both parties - that's OK. Keeping the discipline is important. A strong relationship will create more productive 1:1s over time.

"A hallmark of a trusting relationship is that people feel they can share their mistakes, challenges, and fears with you. If they're struggling through an assignment, they tell you right away so you can work through it together. If they're having issues collaborating with somebody, you hear it first from them and not through the grapevine." - Julie Zhuo (Source: The Making of a Manager)

1:1 Agenda

The simplest 1:1 agenda is to divide the meeting into 15 minutes of the Direct Report's agenda items and 15 minutes of the Manager's items.

What Great Managers Do

Great managers don't just influence their direct reports and empower their people to perform. Great managers think globally, working across teams and functions to drive results for the organization.

Google's Project Oxygen initially identified (2008) the eight behaviors of their best Managers. As they scaled, they updated that list to 10 behaviors, as employees made clear they wanted Managers to exhibit more "cross-organization collaboration" and "stronger decision making". Those behaviors are the subject of this section.

Circulate Across Teams

Part of understanding the broader organization is building and maintaining dialogue across functions, with other managers and individual contributors.

"Organizational learning can't happen in isolation. It always involves the joint participation of a set of middle managers. This requires that they actually talk to each other and listen to each other, rather than just taking turns talking to and listening to a common boss." - Tom DeMarco (Source: Slack)

Walk Around

"Managing by Walking Around" is about seeing and sensing what's happening in an organization. The more we can see with our own eyes, and the more we can avoid assumptions, the better decisions we can make.

Sam Walton's practice of walking around and taking notes on index cards can be applied in a remote work environment (i.e. through an "Issues List"), and at any level of management.

"He carried a pack of 3-by-5-inch index cards with him and wrote down every bit of feedback he received. Then, at 7:00 a.m. Saturday management meetings, Walton pulled out those cards and shared what he’d been told, who had told him, and the employee’s location at the particular store. The team evaluated the feedback and assigned tasks for action and follow-up." (Source: CEO Tools 2.0)

See The People & The System

Managers have a valuable perspective on how work actually gets done because they see it and hear about it firsthand, and from other managers around them. When they see how their direct reports and teams contribute to the larger organization, they can begin to effectively manage Business Processes.

Differentiate Person From Process

New managers often overreact to issues they hear from their direct reports. They often try to "fix the people,” rather than assess the system at work. Once a manager can understand patterns in performance and see how business processes serve or inhibit their people, they begin to differentiate whether a given issue is a personnel issue or a process issue.

Ray Dalio explains what Managers do when they reach this point:

"They create process-flow diagrams to show how the machine works and to evaluate its design. They build metrics to light up how well each of the individual parts of the machine (most importantly, the people) and the machine as a whole is working." (Source: Principles)

Understand Variation

New managers are brought a slew of problems and one-off issues. It's easy to see one issue twice and conclude that things just aren't working around here. Managers need to treat issues seriously but also understand whether the issue is one of simple variance and whether it's an issue worth solving at all.

Drawing up process-flow diagrams and seeing the "machine," is helpful, but it doesn't account for variance in performance. Variance cannot be stamped out, as the organization is NOT a machine, but a collection of people who will make mistakes.

The Manager who try to over-correct for variance become process enthusiasts who:

"Sees trends where there are no trends. ("Costs are out of control!")

"Misses trends where there are trends. ('We have had a few problems with deliveries but nothing unusual.') (Source: The Leader's Handbook)

Differentiate Process From System

In a given function, there are multiple systems at work. Processes are the things people do within a system. A system has multiple processes running within it. Improving results is not always about improving single processes. Sometimes, systems need overhauling.

In a Marketing team, the "Social Media" system might have a single process for "Publishing on TikTok," which includes multiple stakeholders, contributors, and procedures. Most managers can improve a process by streamlining it, adding failsafe steps, or improving communication at different steps. Great managers can see how the "Publishing on TikTok" process interacts with other processes and fits into the overall Social Media system.

They're able to see strategy incoherence, limiting beliefs or assumptions behind the system. They see that optimizing the "Publishing" process for local maxima, beyond a certain point, doesn't improve organizational performance.

The great manager who can see at this layer of abstraction is a candidate to lead a function.

How to Create Managers

Whether you decide to hire Managers mostly from the outside or develop them all internally, every organization with the intent to grow should have a plan for developing people into Managers. If you don't have a plan, your only succession plan is to recruit from the outside.

Training new managers on coaching and mentoring, feedback and 1:1s will help you avoid the common problems of micro-management and ensure that employees have the best employee-manager experience they've ever had.

Identify Your Leaders

Emotionally Intelligent People

Management can be a difficult change for superstar individual contributors. It's a job of emotional labor, it's less connected to visible, measurable impact, and it's often not as creative as individual contributor roles. New managers who lack emotional intelligence can struggle the most.

Emotionally intelligent people have Self Awareness, Social Awareness, and the ability to Self-Regulate. They can build and manage effective relationships with others. There's an argument to be made that this is the most important ability to staff in your organization:

"Social and emotional abilities were four times more important than IQ in determining professional success and prestige (Feist & Barron, 1996 cited in Cherniss, 2000). (Source: The Business Case for Emotional Intelligence)

Unfortunately, we can’t train self-awareness, and developing it takes time. Of all of the abilities that go into Management, we're least equipped to "develop" emotional intelligence in the business world.

To find your managers, you need to identify people who exhibit high emotional intelligence.

"75% of careers are derailed for reasons related to emotional competencies, including the inability to handle interpersonal problems; unsatisfactory team leadership during times of difficulty or conflict; or inability to adapt to change or elicit trust." (Source: Business ROI of EQ Training)

Who's Leading With Influence?

Instead of trying to shoehorn every expert IC into a management role, identify your people who already exhibit leadership abilities. Leadership is not always loud. Look for people who feel rewarded for helping others, even in small ways, like mentoring a new hire or including others in team events, or calling on quiet people in meetings.

"Who is building the bridges between previously disparate, perhaps even adversarial, groups? Who is creating channels of communication and connectedness? Who is doing the hard daily work of building trust? Who promotes everyday civilities and politeness? Who sees the isolated individuals and includes them? Who helps the organization see the value of diversity and the pathology of exclusivity and harassment? Who creates community at work?" - Peter Scholtes (Source: The Leader's Handbook)

Hire Self-Managers

Look for people who lead themselves, who don't wait for direction, and who get a lot done. If they can't manage themselves, they'll be unlikely to handle a less straightforward management role, and they'll be less likely capable of helping others.

"Have they been self-sufficient at previous jobs? Have they defined their own role before? Have they started their own site/company before? Or done their own thing in some other way? Find someone with initiative and a budding entrepreneurial spirit. And then nurture it." - Basecamp (Source: Hire Managers of One)

Other Key Traits

• Core Values match.
• Capable in their IC role. If they can't leverage their experience to help Direct Reports, they'll be automatically disadvantaged compared to peers in a Management role.
• Proven Feedback, Coaching & One-on-One Skills. These are the skills you can train before making an internal hire.

Train Management Skills Using These Tools

How to Hold Management Accountable

Be Clear About What They're Accountable To

Holding managers accountable is a key problem in many organizations. It’s easy to extend autonomy to managers and directors and then allow them to take it away from their direct reports. I believe that equation needs to be flipped. Control needs to be distributed to direct reports, while managers need complete clarity about what they should be doing and how they should be doing it.

Without clarity on what outcomes managers are accountable for, you can't hold them accountable. I want my managers to develop people, create and implement positive change in line with our vision and keep people engaged and performing. How you hold them to account is about measuring them against the criteria you choose.

Measure Performance

Measuring the performance of managers tends to be even more difficult than your average IC. New managers don't get to choose the system they work within or the people who report to them, and they don't do "the work" themselves. Over time, their inputs lead to good outputs, but in the short term, you need to know that they're putting in the right kinds of effort.

Like with any role, performance measurement should not be reduced to a single number. A composite of several areas, namely team performance and survey results tends to be the best way to assess the performance of a given manager. Here are a few categories to think through.

Team Performance

Survey Results

Direct Report Retention Rate

Upskilling/Leveling & Team Promotions

Values Measures

OKR/Rocks performance

Foundation

PurposeMissionVisionCore ValuesStrategy

Designing The Organization

Understanding CultureCultivating CultureOrganizational DesignOrganizational StructureOperating PrinciplesLeadership TeamsDesigning ManagementEffective Teams

Operating Effectively

Operating RhythmGoalsPlanningInternal CommunicationMeetingsMetricsBusiness ProcessResolving IssuesDeciding & Delegating