The Challenge of Leading Leaders

The Challenge of Leading Leaders


In 2010, Sarah Crosby joined Multidata as a design engineer.  Armed with a PHD in engineering and an MBA, she excelled in her first position as an individual contributor to the product development team, gaining visibility internally and receiving several excellence awards from industry specialists.

Her talent didn’t go unnoticed – by 2015 she was promoted to manager of the product development team – with a split responsibility for managing the team and being the lead engineer on several mission critical projects.  Things went well – particularly well in project leadership.  And she relished setting objectives and holding her team members accountable for getting results.

In 2020 Multidata acquired Senseo and merged the product development teams – and Sarah stepped into her first senior leadership role – as a leader of leaders.  The merged team was excited about her vision and committed to achieving it.  Anything Sarah needed was provided.  The team had the resources and objectives to succeed.  

Yet by early 2021 Sarah was in trouble.  Her project leadership was still widely recognised as effective; but her direct reports complained of “micro-managing, directly engaging their people, and ignoring team and individual development needs.”  

What went wrong?


Sarah’s story is remarkably common – talented individuals stepping into increasingly senior roles facing new challenges with old behaviors – behaviors that were highly effective in previous roles but less so (or even dysfunctional) in the current role.

Why does this happen?

Leading leaders is very different from managing individual contributors and certainly from being an individual contributor oneself.  Sarah fell foul of some very common challenges of being a leader of leaders:

Challenge 1: Understanding the New Role Expectation

As a leader rises through the organisation, the span of potential impact increases dramatically, but in inverse proportion to the level of direct control.  Expectation shifts from delivering results oneself, to delivering through others to – in the case of leaders of leaders – creating the capacity in leaders to deliver through others.  This creating capacity involves a range of critical skills: thinking skills (developing the right strategy, structure and enablers) and affective skills (coaching, motivating, creating insight and the will to change).

Being successful at this level requires understanding that the role is one further step removed from doing things to creating and leveraging organisational and individual capacity.  It also means living with greater ambiguity – with the uncertainty of the instrumentality between one’s efforts and concrete results.  If a leader doesn’t understand this – or more importantly doesn’t like doing it – our advice is stay where you are!

Challenge 2: Letting Go of the Old Role Expectation

For sure, the old phrase “what got you here won’t get you to where you need to go” is especially true when being promoted to leader of leaders.  So many leaders are working to the expectation of their previous role.  If the study of the psychology of transition has anything to offer leaders, it is this: it is vital to let go of old beliefs and behaviors before one can move on to adopting new ones.  So many leaders attempt to hang on to the old expectation while also adopting the new one – and end up regressing into old ways.

Challenge 3: Adding Value

Very much related to the first two challenges is a self-expectation.  Leaders of leaders need to focus on the few “right” activities that have the greatest impact on their followers’ success.  And here, “less is more.”  The essential question the leader must ask is “what is the minimum I can do to move my followers and the organisation ahead.”  Leaders of leaders must become minimalists – searching for the one or two activities that make the greatest difference rather than trying to shoot every arrow in their quiver at the target. Minimalist not perfectionist.

Challenge 4: Shifting Scope

How a leader spends their time also changes.  A first line manager may spend 70% focused downwards on direct reports, 20% focused on working with peers, and 10% supporting their boss.  At the leader of leader level, the distribution shifts significantly – 50/30/20.  One of the most neglected role functions of this level of leader is the part they play as a member of their boss’ team – beyond the part they play in delivering results thorugh their team.  The leader has a key responsibility to participate with peers to solve collective problems owned by the boss.  In so many organisations, team meetings are seen as the opportunity to report one’s own results in the presence of other team members.  The missed opportunity is for the team to work collectively on common organisational issues that affect the majority of their functions.

Challenge 5: Shifting Style (competing to collaborating)

At the lowest levels of leadership, a leader may find herself competing for resources with other leaders – for a greater slice of a fixed size pie.  At some point this changes.  Leaders of leaders need to work collaboratively to make the pie bigger – and this requires a different skill set.  Leaders need to shift from “making the case” for their area to get more resources into working collaboratively with peers to understand the opportunities and craft a win-win strategy that goes beyond meeting everyone’s needs. 


If your organisation aspires to get the best from its senior and business unit leaders, our advice is to invest in:

  1. Clarifying the role expectation – what is expected at this level and how that differs from the previous level
  2. Equipping with the strategic thinking and capacity creating skills – those “behind the scene” competencies that create organisational clarity and grow follower problem-solving ability
  3. Let leaders lead – expect and value experimentation, recognise that mistakes will be made, focus on what is being learned.  And wait expectantly for leadership breakthrough

If getting the best is important to your organisation, reach out to our team of highly experienced experts who can build a custom program to let your leaders lead!

Scott Kerr – Senior Facilitator, Clear Connection UK Ltd

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