Leadership: Not a People Pleasing Position

Introduction

Leadership is often about making difficult choices. It’s not always about being agreeable or accommodating every request. True leadership lies in understanding the bigger picture and making decisions that may not please everyone but serve the greater good. Over the past few days, two particular experiences have reinforced this for me – the realisation that, as a leader, you can’t be a people pleaser. More importantly, there are times when you must say no for the benefit of the entire team or organisation.

Incident 1: Balancing Client Expectations with Organisational Integrity

Recently, my team and I were engaged by a client with a strong sense of purpose, one whose mission aligned closely with our own values. As a result, we onboarded ourselves at a haircut on our standard fees to accommodate the client’s request, believing in the value we could deliver through our structuring and advisory services. We saw their potential and connected with their long-term goals, which is why we agreed to a fixed scope and fee structure for the assignment.

During the engagement, a new requirement emerged—the client was advised by us to incorporate an LLP, a task we knew would be highly complicated. It involved providing intricate structuring advice and drafting a specialised LLP agreement, something that would demand substantial time and effort. The client requested us to do it at a specific additional fee. While my team recognised the opportunity for additional fees, I, as the leader, had to consider the larger picture.

The challenge here was not just the potential increase in work but also staying true to the ethos of our organisation. We had already agreed to a fee reduction, and taking on this new task would risk overextending the team. More importantly, it could lead to a spiral where the engagement would become time-intensive, ultimately eroding the team's enthusiasm and turning what was initially a positive experience into a burden.

Saying no in this situation wasn’t about missing out on potential fees—it was about maintaining the quality and integrity of the work we had promised. It was also about protecting the team from burnout and keeping our broader goals in mind. At that moment, it became clear that leadership is not about pleasing everyone or stretching beyond capacity, but rather about understanding the boundaries that keep both the client and the organisation in a healthy, sustainable relationship.

Incident 2: The People-Pleaser Dilemma

The second incident involved a team member who made a request that, which to him, seemed reasonable. We had open communication about the request, and while the team member believed it was within the rules of the organization, I knew that similar requests had been denied in the past. Allowing this request would likely create a domino effect, with other team members citing this decision as precedent for their own requests.

The complexity here was that the team member truly believed their request was valid, based on informal conversations and assumptions. However, there was no formal basis for this belief, and granting it would compromise fairness across the organization. It became a question of my word versus theirs, but I knew that my decision had to be consistent with past actions and the overall direction of the firm.

As a leader, I had to weigh the impact of this decision not just on the individual but on the entire organisation. It wasn’t about denying someone’s request simply for the sake of it, but about ensuring that any decision made was fair, consistent, and in line with our organisational policies. There are times when leaders must consider the “we” – what is best for the collective – over the “me” or “you”. This is especially true when there’s a risk of setting a precedent that could negatively affect the team in the future.

One thing I realised through this process was the need for formal documentation of certain rules that were previously more informal. This oversight led to confusion, and moving forward, we ensured that all rules were clearly documented and accessible to avoid similar situations. It’s a reminder that even though something may seem obvious, clarity and consistency in communication and guidelines are key to avoiding misunderstandings.

Reflections on Leadership:

These experiences reminded me that leadership isn’t about making decisions that please everyone. It’s about doing what’s right for the organisation as a whole, even if it means having difficult conversations or saying no when needed.

Leaders must balance empathy with practicality, taking into account both the individual and the collective impact of their decisions. Open communication is essential, but it’s equally important to have the courage to stand firm when a decision is in the best interest of the organisation. This might not always be popular, but leadership isn’t about popularity—it’s about responsibility.

Leadership is about more than just making people happy. It’s about steering the organisation in the right direction, even when that means making tough calls. Sometimes, saying no is necessary for the greater good. Leaders must be willing to make decisions that may not favour any one individual but serve the collective interests of the team and the organisation. At the end of the day, leadership is about guiding the whole team forward, even if it means not being liked all the time.