In this first article of this two-part series, we addressed some common challenges that middle managers face. Here, we’ll consider the leadership skills that can help address these challenges and set middle managers up for success.

We hear a lot about the need for “leadership presence.” But what does this mean, really? Leadership presence means role-modeling the organization’s core values and the behaviors you want to see in others — even when you think no one is looking. This includes ensuring that your actions consistently match your words, and that you can authentically represent organizational leadership (in messaging and overall presence).

Why is leadership presence needed at the middle management level?

As the middle manager’s span of influence expands, so does the leadership shadow they cast. With that in mind, the behaviors they exhibit are witnessed and modeled by a greater span of employees. Furthermore, attention comes even from others outside of their leadership scope (e.g., stakeholders on other teams, front-line team members in adjacent teams, more senior leaders). Paradoxically, the amount of time they have with each person under their span of influence tends to be reduced, meaning that each interaction creates a stronger and more lasting impression — whether it’s good, bad or neutral. Every connection and communication point counts more and requires more intention.

With that in mind, the sub-skills needed to help middle managers cross this threshold include:

  • Role modeling curiosity, humility, and ownership up, down and across the organization.
  • Delivering clear, consistent and purposeful communication.
  • Interacting with intention, authenticity and psychological safety.
  • Flexible thinking.

People Leadership: From Reacting to Needs to Empowering Growth

What does that mean? Moving away from reactionary leadership and toward intentional growth requires assessing present and future team members’ needs (and business needs) when decision-making rather than reacting to specific requests. When done well, the middle manager shares context and goals to enable strong execution while seeding future growth, without direct involvement. Beyond just modeling this behavior and being the single point of accountability, the middle manager needs to equip their leaders to also empower their teams to make effective decisions.

Why is this needed? In their previous lives as front-line managers, middle managers were used to addressing escalations, filling skills gaps and reacting to problems. With a broadened scope, that will no longer be the most effective way to get work done (or the best use of their time). Not only will it cause those they lead to become stagnant in their growth, but also it can lead to micromanagement or even a lack of accountability. Not to mention that the middle manager becomes a bottleneck to getting work done instead of a remover of obstacles. To avoid this, leaders can’t just delegate and hope for the best. Otherwise, they’ll wind up jumping back into “course correct mode.” Rather, they need to assess the situational needs, the strengths and gaps of their team, and intentionally take the most effective and relevant leadership approach to coach, direct and/or empower decision-making at the right level.

With that in mind, the sub-skills needed to help middle managers cross this threshold include:

  • Situational awareness and leadership.
  • Coaching through empowerment rather than direction.
  • Decision-based rather than task-based delegation.
  • Creating a culture of accountability.

Leading Teams: From Leading Down to Leading Out

Leading out requires shifting your mindset away from viewing your team members as “direct reports” and toward viewing them as peers or collaborators. This expands the concept of team from one to many. The middle manager is a leader and/or member of a multitude of teams that intersect directly and indirectly. Within some teams, the middle manager becomes the spokesperson for their function out to the organization. For others, they become the spokesperson of their peer and leadership group to stakeholders or to the team they directly manage.

Effective middle managers are able to assess when their role is to be informed, when it’s to be consulted, and when it’s to execute or drive decisions. They’re also able to establish norms and collaborative, inclusive environments that create a “win-win-win” for their teams, their functions and the business as a whole.

Why is that needed? As the middle manager’s scope and accountability expands, their responsibility shifts from depth to breadth. This requires awareness, context and accountability that’s aimed more toward the enterprise level. As the middle manager’s time is spent more consistently with peers and higher-level leaders, it’s essential for them to develop the relationships and strong ways of working that provide an understanding of other team’s needs and challenges to drive the best partnerships for themselves and their teams.  

With that in mind, what are the sub-skills needed to help middle managers cross this threshold?

  • Stakeholder awareness, analysis and
  • Motivating through influence.
  • Inclusive leadership and cross-functional collaboration.
  • Developing and implementing team infrastructure and norms.

Business Leadership: From Planning for Today to Preparing for Tomorrow

To go from planning for today to planning for the future requires leaders to move away from reactive problem-solving to proactive, strategic planning in service to team and organizational long-term success. When done well, middle managers seek out and gather context and data (from their network, research, observations and data analysis) to assess needs and impact paths. They learn to think like a social scientist: identifying root causes or opportunities, designing experiments, determining effective measures and creating evaluation gateposts. Throughout the process, they have an eye toward questioning assumptions, continuously learning and mitigating risk.

Why is that needed? Whether planning organizational structure, establishing goals, designing processes or launching new initiatives, there’s more risk, more grey area, and greater magnitudes of data and options for middle managers to sort through than they’re used to. While the other transformations require different applications of existing skills, this shift requires a whole new way of thinking. As a front-line manager, they were most often responsible for executing others’ decisions. When the decisions were theirs to make, they were often smaller in scope or more focused on the present situation or team. Since reactive execution is narrower in scope and strategic decision-making necessitates more expansive thinking, it’s a mindset that the middle manager isn’t automatically wired for. Because of that, middle managers need training and practice in determining what to assess, who to partner with, how to develop and execute the right experiments, and how to communicate in the language of higher-level stakeholders.

With that in mind, what are the sub-skills needed to help middle managers cross this threshold?

  • Developing a strong business case that identifies problem statements and root causes.
  • Research backed experimentation and iteration rooted in design thinking principles.
  • Data analysis, visualization and storytelling.
  • Leading with agility through uncertainty and a change of direction.


So … How Do We Develop These Skills?

Middle managers already have core leadership foundations – whether through official learning programs, personal experiences, or both. Their development relies on approaches that enable them to move from awareness into action, while creating the space to practice new skills and reinforce desired behaviors. In this way, a middle manager’s development should follow the flow of a cycle rather than a linear program, like so:

What might this look like in action?

Imagine that leading with design thinking principles is a new concept to your middle managers. This would be a natural spot for initial coursework to introduce the principles and process, and what this looks like in practice for a leader. After engaging with the coursework, a middle manager can be paired with a coach to process how those skills could be utilized within their existing cross-functional groups today to come up with an initial plan. From there, the middle manager would design an experiment to leverage design thinking techniques to develop a new meeting norm, with clear measures and timelines, to test the execution and effectiveness of what they’ve learned. They’d engage with their community before launching the experiment to get input and throughout the experiment as a feedback loop to make tweaks accordingly. They can then explore additional trainings and coursework to elevate their knowledge further based on their learning, challenges and successes with implementation.

At each level of the process, incentivization is key to recognize and reward not only the engagement with the material and completion of assignments, but also the overall learning and role modeling of behaviors. Mechanisms to celebrate the progress and effort, in addition to the outcomes, can help fuel motivation and also instill a practice that would be beneficial for the manager to institute within their own teams.

Furthermore, incentivization is at the core of this cycle, because we’re more likely to get the behaviors we want to see by recognizing and rewarding them in the first place. Organizations that build structured leader recognition, whether it be through surveys, performance incentives, and/or spotlight awards, are more likely to create a culture of leadership behaviors they’d like to see. Making these awards organizationally embedded and generated bottom up can also create cultural accountability, surface stories of these behaviors in action and seed leadership awareness at the front-line level.

Putting It All Together

Just as a middle manager’s development needs to be treated as a cycle rather than a linear approach, the design of the development approach needs to follow suit. Skills at the middle managerial level are rarely used in isolation, and it’s the integration of these skills that separates high performing middle managers from the rest. When managers can forge connection points between individual skills for holistic application, and then zone into the right tool or approach for the situation, they begin to act more strategically and more proactively. By designing programs that introduce skills as an integrated set that’s situationally applied rather than individual components, middle managers will learn how to think differently through the system of their development. In an intentional and subconscious way, you’ll re-wire their natural filters so that they begin to see and operate on a broader, more connected, and future oriented manner that helps them move from managing a team’s daily performance to driving a function and the business forward.