2 steps to crush the 'nice leader' dilemma and evoke respect

Mark Travers
Written by Mark Travers
on July 25, 2023 2 minute read

Leadership is a balancing act, teetering between being a pushover and a tyrant – this is especially true for Xolopreneurs.

Whether leading a remote team or rallying support for a project, many of us have had to tap into leadership skills. So, why do some seem to naturally command authority, while others wrestle to be taken seriously?

The answer could reside in our personality traits. This isn't to say that only specific personalities are cut out for leadership, but rather our personalities significantly shape our leadership styles. One such style that may encounter challenges in maintaining effective control is the 'nice leader.'

While 'nice leaders' are reliable and never shy away from responsibility, they may grapple with the harsher aspects of leadership: exercising power over a group, having difficult conversations when needed, and handling the inevitable backlash.

Today we’ll cover two strategies for Xolopreneurs striving to fortify their empathetic leadership style without morphing into an iron-fisted dictator:

#1. Leadership doesn't equate to doing everything yourself

Holding yourself accountable to deadlines is daunting, particularly for those who are innately averse to pressuring others for results. 

As a Xolopreneur, you may encounter situations where a freelancer may be lagging behind schedule, unable to deliver their work on time. The challenge here is finding the balance between being understanding of unforeseen circumstances that might affect their work and ensuring that the project stays on track.

A 'nice leader' may feel inclined to lighten the load of an overworked team member by shouldering some of their tasks. However, a leader's true power lies in their capacity to delegate tasks.

According to Harvard Business Review, you can maximize your time, resources, and energy as a leader by being more selective. When your involvement is requested, consider one of three responses:

  • Yes. This is warranted when your leadership skills are crucial – such as for executive decisions or providing feedback.
  • Yes, if. This response is apt for tasks requiring the direct involvement of another individual. You should specify that you'll only function in an advisory capacity.
  • No. This is appropriate when you believe your involvement will be more impactful elsewhere.


As leaders, we often grapple with being “more essential and less involved”.

Jesse Sostrin offers a simple interpretation: "Your involvement is a mix of opportunities, mandates and choices regarding the work you do. How peripheral or crucial you are to the success of that work depends on how decisively and intelligently you engage those around you."

#2. Dodge empty 'therapy speak'

As a leader, delivering less-than-pleasant news is part of the package. Whether it's communicating pay cuts or the cancellation of a much-anticipated virtual meetup due to budget constraints, the leader must bear the brunt.

A 'nice leader' might feel compelled to sugarcoat their words to mitigate disappointment and dodge disapproval. Phrases like, “we’re all in this together,” and “we understand that this may be challenging,” are common.

However, a survey by The Harris Poll of approximately 2000 American employees revealed that 'therapy speak' – empathetic-sounding language without appropriate follow-through – leaves employees feeling more resentful towards leadership and less enthused about their roles.

Most people value straightforward, authentic communication over therapy-speak. So, when the time comes to deliver bad news, avoid overcomplicating it or attempting to console your team preemptively. Delivering challenging news honestly and tactfully is a skill that will serve you well, even beyond professional realms.


Good leadership isn't about pleasing everyone but doing what's best for the team, even if they don't always agree. It's about shaping team dynamics and inspiring action. For Xolopreneurs, this means navigating the complexities of remote and digital leadership, connecting with diverse individuals in varying locations, and inspiring a shared vision amidst the constant ebb and flow of digital life.

New call-to-action

About Mark

Mark Travers, Ph.D., is an American Psychologist with degrees from Cornell University and the University of Colorado Boulder. Xolo helps him run his online therapy practice, www.awake-therapy.me, from whatever part of the world he is currently living in.