A Guide for Leadership Development through Scale

A practical guide for developing leaders as they progress from managing 1–300 people.


Jenilee Deal

3 years ago | 5 min read

Leading yourself

Before you can lead others, you have to lead yourself. This means you know how to work in an organization. You have mastery of the foundational skills of working in a professional setting, including being responsible, reliable, hardworking, organized, communicative, and collaborative.

You also tune into the norms of your company culture and adapt your working style appropriately.

Leading a team

To successfully lead a team, you need to know how to lead and manage a group of Individual Contributors (ICs). Typically, your team size is three to ten people, you manage 1–2 “people issues” at a time, and you may do both IC and Manager work.

Management Skills

  • Operations: Effective leaders are careful to get their “meeting operations” in excellent order. This means they master the type, frequency and content of their most important meetings. At “leading a team” stage, the most important meetings include: 1:1s, team meetings, and offsites.
  • Practices: Leaders must know how to execute on key practices such as performance reviews, compensation setting, goal management, leaves of absence, role transfers, promotions, hiring, terminations, and career development. The approach to each practice will vary from company to company.
  • Performance: The leader should have a vision and strategy for team performance. Regardless of approach, the leader must understand each individual’s strengths and weaknesses, coach for high performance, and manage under-performance.
  • Structure: Optimize the structure of each role. Instead of taking this for granted, leaders can be proactive and strategic in how they structure the work for each individual and role.
  • Risk: It is important to have rudimentary knowledge of legal, financial, and reputational risks. An understanding employment law, especially discrimination and harassment, can be very helpful. The general idea is to develop strong judgement about when to escalate issues to upper management, legal, etc.

Leadership Skills

  • Vision & Strategy: Ensure clarity of team’s vision and strategy. Skills include either: (1) creating a team mission, charter, and goals, or (2) ensuring that leadership at higher levels are doing so.
  • Alignment: Ensure each individual understands how to align their work with highest impact on the vision. Skills include embedding this topic into 1:1s and finding other ways to ensure understanding and commitment to the team’s goals, strategy, and vision.
  • Communication: While levels of transparency are company-specific, leaders need to be able to share information about key decisions and changes. Skills include cascading communications from senior leadership to the team, as well as developing an instinct for team-specific communications (e.g., communications for terminating someone on the team).
  • Trust: Foster trust and cohesion among the team. Skills include team building, mastering conflict, modeling effective communication, and having crucial conversations.
  • Accountability: Hold each individual accountable to performance standards and expectations. Skills include effective communication about expectations, as well as consistent application of reward and punishment that align with those expectations.
  • Motivation: Inspire the team to do the highest impact work. Understand the motivation and personal styles of every individual. Skills include empathy, active listening, and influence.
  • Collaboration: Ensure working relationships are healthy and collaboration is strong. Skills include embedding this topic into 1:1s, conflict resolution, and a method for pulse checking key relationships.

Leading a large team

To successfully lead a large team, you need to know how to lead and manage a group of ICs and Manager(s). Typically, your team size is 10–50 people, you manage 3–10 “people issues” and “org issues” at a time, and you do Manager work exclusively.

Management Skills

Operational complexity increases. In addition to the skills in “Leading a team,”

  • Operations: The types of meetings expand to include management meetings, management offsites, and skip level 1:1s . Team meetings may become more involved “All Hands” meetings.
  • Practices: The biggest shift here is, (1) leading managers to execute on practices, and (2) creating a process to ensure calibration of decision-making across the management team (e.g., compensation calibration). Whether it’s 2 managers or 10, consistency is paramount.
  • Performance: Also a big shift here in terms of, (1) leading managers to manage performance, and (2) creating a shared set of expectations and performance for the team; this could already be in place as part of goals, strategy, and vision, but may also need additional process such as a simple quarterly retrospective.
  • Structure: Similar concept but now optimizing the structure of the teams and management span, not just the roles. A leader has to consider several aspects of the structure of their team.

Leadership Skills

In addition to the skills in “Leading a team,”

  • Vision & Strategy: Complexity of this task may increase due to number of sub-teams, in which case there may be several team visions and strategies that need to align with one another.
  • Alignment: Ensure teams within the large team are aligned. Skills include embedding this topic into management-level meetings.
  • Communication: Complexity of this task increases due to the levels of management as well as number of key decisions and changes. Leaders should find a way of getting feedback on the effectiveness of their communication.
  • Trust: Similar concept but new practices are required to foster trust and cohesion. Skills include more time dedicated to offsites, all hands, and team building.
  • Accountability: Driving accountability through managers is the new skill. A great leader will empower each manager rather than use top-down pressure and authority.
  • Motivation: With a larger team, it becomes essential to influence through broad communications like presentations, emails, and memos. Some leaders are better in person than in writing, or vice versa — a leader should find their style and hone the skill.
  • Collaboration: Similar concept, although types and number of relationships increase. Leaders should constantly scan for relationship health between peers, internal stakeholders, ICs to managers, ICs to executive leadership, managers to executive leadership, etc.

Leading an organization

To successfully lead an organization, you need to know how to lead and manage several teams as one whole unit. Typically, your team size is 50–300 people, you manage 10+ “people issues” at a time as well as “organizational issues,” and you do Manager work exclusively.

Management Skills

In addition to the skills in “Leading a large team,”

  • Operations: A large part of a leader’s job is ensuring that the right people are meeting at the right time and talking about the right things. Without an excellent operational strategy in this area, a leader will very likely underperform in their entire role. Additional meetings to consider are forums for important topics, as well as a meeting cadence with multiple management groups (e.g., direct reports versus all managers).
  • Practices: Typically leaders with hundreds of people in their organization are leading more involved processes such as budgeting, headcount, and succession planning. The complexity of calibration processes increases; it is an art to calibrate across multiple teams, levels and practices in a way that is efficient and effective.
  • Structure: Complexity of organization structure increases greatly. Often there are tradeoffs between change, org durability, and people. Organizational development and change management are important underlying skills.

Leadership Skills

The leadership skills from 50 people to 300 people are fairly similar. In my opinion, the big difference is that any gaps in leadership skills are more visible in more damaging to the team.


I believe that diverse teams and inclusive cultures are critical to overall success of a team and organization. I did not include skills here because they are company-specific.

Similarly, I did not include additional company-specific skills such as managing a distributed workforce.

Originally published on medium.


Created by

Jenilee Deal







Related Articles