Originally published on LinkedIn on 14 May 2026.
Sarah had waited years for this moment.
Six months as a newly promoted partner. A team of six. A caseload she knew inside out. She had been the person colleagues came to when they needed something done properly. She was considered reliable, technically excellent, and well liked. The promotion felt like recognition of everything she had built.
Six months in but something wasn’t quite right.
The team seemed fine on the surface. Nobody was complaining. Deadlines were mostly being met but Sarah found herself staying later than anyone else, quietly picking up work that should have been done by others. She had also been putting off a conversation with Jamie, a mid-level fee earner whose billing figures were consistently below where they needed to be. She told herself she was being supportive. Jamie was going through a difficult period therefore she would address it next month.
The promotion that changes everything
The skills that make an excellent fee earner are not the same skills that make an effective leader. This is one of the most consistent patterns in professional services and one of the least discussed.
As a fee earner, being liked is an asset. Relationships are currency. The instinct to keep people comfortable, to smooth over tension, to absorb a problem rather than create conflict. These behaviours serve the work well with clients, colleagues and with the daily rhythm of a busy practice.
The moment someone is promoted into a leadership role, the same behaviours begin to work against them. Not dramatically or immediately, but steadily, until the cost of them becomes impossible to ignore.
When kindness becomes the problem
People pleasing as a leadership blind spot rarely announces itself as such. It feels like empathy or patience. It feels like giving someone the benefit of the doubt.
Research by organisational psychologist Tasha Eurich found that only 10 to 15% of leaders have an accurate picture of how their behaviour is experienced by the people around them.
In my experience, for newly promoted leaders that gap is widest precisely when it matters most. In the first six months when the team is forming its understanding of what their leader values, what they will tolerate and what they will avoid.
Sarah wasn’t avoiding the conversation with Jamie because she didn’t care about performance. She was avoiding it because she cared too much about the relationship and hadn’t yet understood that protecting the relationship at the expense of the conversation was itself a form of harm.
This is not an argument against kindness or patience in leadership. A newly promoted leader who listens carefully, builds trust gradually, and avoids unnecessary confrontation may be doing exactly the right thing, particularly in a team that has experienced difficult leadership before. The problem arises when these behaviours become the default, applied regardless of context and without the leader being aware of the pattern they have fallen into.
What the team is learning
Teams are remarkably accurate readers of their leaders. They notice what gets addressed and what gets avoided. They notice whose underperformance is tolerated and whose isn’t. When a difficult conversation doesn’t happen, they draw conclusions from its absence.
In my experience working with newly promoted leaders, when they consistently avoid difficulty, the team does not experience this as kindness. They experience it as a signal that standards are negotiable and that the leader can be managed.
Over time, the highest performers in the team, the ones with the most options, quietly recalibrate their effort. Why work to a standard that isn’t being held consistently? Unclear expectations and inconsistent performance management are among the leading drivers of disengagement in mid-level fee earners. People pleasing leadership, without intending to, creates exactly those conditions.
The moment it becomes visible
For Sarah, that moment of visibility came sooner than she expected.
An external facilitator ran an anonymous session on team dynamics at a firm away day. The feedback was careful and professional but the pattern was clear. The team felt that standards weren’t being held consistently. They felt uncertain about what was expected. One response, which stayed with Sarah long after the day ended, said simply, “we like Sarah a lot. We are just not sure she is leading us.”
By the time a blind spot becomes visible, it has usually been shaping behaviour for longer than anyone realised. The cost is not always obvious because it accumulates in the small decisions the team stops bringing to the leader, in the effort that quietly reduces, in the talent that starts looking elsewhere.
The shift that changes it
The adjustment required is smaller than most newly promoted leaders expect but it requires something specific. Not a change of personality or the abandonment of the relationships that matter. Instead, the leader simply needs to understand that the most supportive thing they can do for their team is to hold the standard clearly, address difficulty early, and trust that the relationship is strong enough to survive an honest conversation.
It is worth acknowledging that some of this is structural rather than personal. A newly promoted team leader who has never been shown what good leadership looks like at their level is not entirely responsible for the gap. Firms that invest in technical development without investing equally in leadership transition are creating the conditions in which people pleasing becomes the path of least resistance.
People pleasing leadership, at its core, is a confidence problem dressed up as kindness. The leader who avoids the difficult conversation is not protecting the team. They are protecting themselves from discomfort, from conflict, from the risk of being liked a little less.
The team already knows the conversation needs to happen. They are waiting to find out whether their leader knows it too.
The Leadership Blind Spot Brief is published weekly for leaders who want to stay ahead of performance and retention risks that rarely appear in a report. You can subscribe directly on LinkedIn and if it’s useful, pass it on to one person in your network who leads a team.