Practicing radical honesty in managing your team with Steve Evans, CPTO of Aeries Software
July 30, 2026
In this interactive discussion, Enrich member, Steve Evans – CPTO at Aeries Software, challenged leaders to rethink what it means to care for their teams. Rather than avoiding difficult conversations, Steve argued that practicing radical honesty is often the kindest and most effective leadership approach. Through candid examples from his own experience, he explored hiring, performance management, coaching, and the hidden beliefs that prevent leaders from making tough decisions.
Key Takeaways
Hiring great people is one of the highest-leverage responsibilities of a leader.
Steve observed that managers who consistently attract exceptional talent often outperform managers who excel at every other aspect of leadership. Investing time to hire the right people has a greater long-term impact than filling roles quickly.
Leaders almost never regret acting too early on performance issues—they regret waiting too long.
Steve challenged attendees to reflect on their own experiences, noting that nearly every difficult performance conversation he has seen ended with the realization that it should have happened sooner. Delaying action often prolongs problems for both the individual and the team.
Radical honesty is often the kindest approach.
Honest performance conversations may feel uncomfortable in the moment, but avoiding them often creates worse outcomes. Steve shared an example where direct feedback led an underperforming employee to voluntarily resign, allowing both the employee and the organization to move forward positively.
Many leadership decisions are blocked by hidden commitments rather than lack of information.
Leaders often tell themselves they are protecting the team or supporting an employee, when in reality they may be avoiding discomfort, conflict, guilt, or concern about how they will be perceived. Identifying these hidden commitments makes it easier to make better leadership decisions.
Psychological safety should not come at the expense of honest feedback.
Creating a supportive environment means helping people grow—not protecting them from difficult conversations. Employees cannot improve if leaders withhold the feedback they need to hear.
Coaching starts with clear, specific feedback—not assumptions.
Before concluding someone is underperforming, leaders should ensure expectations have been made explicit, feedback has been delivered clearly, and the employee understands what success looks like. Honest coaching gives people a genuine opportunity to improve.
Asking thoughtful questions is often more effective than giving directives.
Whether coaching direct reports or influencing upward, Steve encouraged leaders to lead with curiosity. Asking questions uncovers context, reduces defensiveness, and turns difficult conversations into collaborative problem-solving.
Written follow-up strengthens accountability and reduces misunderstandings.
Steve recommended sending AI-generated notes or summaries after one-on-ones to reinforce expectations, confirm mutual understanding, and create an ongoing record of coaching conversations. This helps both high performers and struggling employees stay aligned.
Strong organizations develop leaders—not dependencies.
Several attendees discussed that one of a leader's core responsibilities is building an organization that can increasingly operate without them. Developing ownership, accountability, and future leaders creates a healthier, more resilient team.
The best performers actively seek coaching—even after success.
Steve closed by sharing a clip of legendary football manager Pep Guardiola coaching a player immediately after winning a championship. His message: elite performers don't avoid feedback—they crave it because continuous improvement is part of their identity. Great leaders cultivate that same mindset on their teams.
