I had no idea how badly blind execution of orders could hurt me, my team, and my company until this happened.
Early in my career as a software manager, I inherited a team from another leader. The entire situation was politically and emotionally charged; perhaps that should have been my first indication that this new role would not be easy.
During my first week on the new job, my boss at the time pulled me into his office.
“Jerry, we have an execution problem on the team. These three people are insubordinate, and you need to get rid of them.”
What was I to do? Here was my new boss, who I respected and wanted to impress, telling me clearly to terminate employees I hardly knew. To say the least, I wasn’t thrilled at the idea of managing folks out so soon. Despite being very respected members of the development team, the boss didn’t like them and had seemingly valid reasons for feeling that way. He was clear that this was a “strong” recommendation.
I didn’t push back; how could I, right? I wanted to be a team player!
I proceeded to fire the problem folks.
Unsurprisingly, the development team was shocked and appalled by the decision, which they saw as my own. In one fell swoop, I had eviscerated whatever trust the team had in me, or ever would. From this point onward, they questioned every move I made and were at times outwardly hostile toward me. The best developers quit. Ultimately, I felt terribly enough that I moved on to start fresh.
Acting blindly on request not only undermined my own performance but also tanked the performance of an overall solid team. It would be a while before I rebuilt my confidence.
In the wake of my mistake, however, I learned five invaluable lessons in leadership:
Lesson 1: Get curious
I never asked why these so-called “problem” team members were considered problematic. Were their performance issues real or was my boss’s perspective influenced by unconscious biases or outdated expectations?
Instead, I should have stopped to think about the complete picture. The top priority, especially in assessing critical decisions, is to dig deep and seek to understand. Now, I always ask questions before acting on another person’s assessment, especially in personnel issues.
I interview peers, stakeholders, and customers.
I review performance data.
I observe team interactions.
For me, curiosity often leads to underlying truths that might be substantially different than surface beliefs. These truths often illuminate more nuanced solutions that produce better value for all those involved. If nothing else, careful investigation reassures colleagues that my decisions are based on facts and reason and not someone else’s word.
Lesson 2: Think, then act
When I first took over that team, I jumped straight into execution without pausing to consider risks and ramifications. I didn’t take time to map out a strategic response, or even form my own opinion on whether firing long-standing employees was the best move.
Instead, I should have trusted that I was hired for my judgment, not just to be an execution machine. Now, before following any directive, I’ll gather information, map out a plan, discuss potential impacts with stakeholders, develop a communication plan. By considering the “what ifs” and challenging assumptions, I’m much more capable of taking decisive, well-executed action rather than slap-dash moves that undercut trust and performance.
Lesson 3: Push back, if warranted
I remember feeling deep down that something about the directive to fire these team members was off. I was so eager to please and fit into my new leadership role, however, that I ignored my own instincts. Worse, I avoided conflict to the detriment of the organization.
Instead, I should have used my own morals and the organizations mission and values as barometers. Now, if I sense a proposal is misaligned with any of these, I speak up. I’m not confrontational for its own sake, but I refuse to rubber-stamp decisions just to avoid conflict. Instead, I err toward presenting logical, evidence-based counterpoints. True leadership demands the ability to protect the long-term health of the team and the business, even if it means challenging someone with greater authority.
Push back comes in many healthy forms:
- asking for more data or seeking a second opinion,
- framing questions and comments in terms of business outcomes,
- requesting validation around potential risks, or
- presenting evidence that contradicts opinions and requesting feedback.
In all cases, aligning interests and goals with the other party creates a foundation for discussion, negotiation, and conflict resolution. Push back and debate, though, require the courage to stand your ground when it means protecting the integrity and success of your team.
Lesson 4: When you screw up, apologize
At the time, I never apologized or acknowledged my mistake to the team. I mistakenly believed that showing this weakness would be worse than expressing vulnerability.
Instead, I should have given them the respect of saying, “I messed up and I’m sorry.” Now, I know that when trust is broken, humility and honesty are the first steps toward repairing it. Even if it’s too late to fully mend the damage, a sincere apology shows that I value people as individuals and that I recognize my role in creating their pain. Acknowledging mistakes doesn’t make me look weak — if anything, I become more credible and human as a leader, and it opens a pathway to potential rebuilding.
Mistakes are inevitable in leadership, but how leaders handle them sets the tone for the team and the organization. Owning an error, without excuses, shows integrity, humility, and respect. Even if trust can’t be fully restored, an honest apology can soften resentment and demonstrate that the relationship is what matters. An apology, I’ve learned, can’t be vague and general; it must be specific about where I went wrong and what I learned. This gesture of accountability encourages others to be open, honest, and responsible in their own roles, ultimately strengthening the team’s culture.
Lesson 5: Clean up your own mess
I didn’t question why this particular situation was even mine to solve. I inherently believed that my boss wanted me to succeed and that he wouldn’t set me up to fail, whether consciously or unconsciously.
Instead, I should have understood that my boss wasn’t thinking about my success, but rather his own. Now, I understand that there are myriad reasons why we all like to avoid uncomfortable situations. For example, I can imagine that perhaps he felt backed into a corner where the only move was to terminate these employees or that perhaps he was scared he would be seen as unpopular making this call himself. If true, I certainly empathize with those feelings!
I also understand that as a leader, it’s my responsibility to prevent scenarios like this from unfolding. If I bring someone onboard, they deserve a fair chance to succeed. If I truly believe tough personnel actions are necessary, I should take them myself before someone else steps into my old role. I also know that if I inherit someone’s mess, I need to handle it ethically and transparently. I’m the one accountable for the health of my team, and if I fail, I need to roll up my sleeves, own the responsibility, and rebuild. That’s how real leadership works: by not pushing the dirty work onto others, but by standing squarely in the arena and doing the right thing.
In conclusion …
These lessons came at a high cost: my credibility, the stability of a good team, and my reputation as a leader. The immediate aftermath of the situation was a dark time for me personally, filled with much introspection and growth.
Mistakes, as they say, don’t make the career, it’s how you recover that matters. Remembering these hard-won lessons fundamentally shaped me into the much more thoughtful, empathetic, and accountable leader I am today.