The working journal / Leadership & teams
Why difficult experiences haven’t made me cynical about leadership
The everyday choices that make leadership matter, especially when doing the right thing has a cost.
I can understand why people become cynical about leadership as their careers progress. The longer you work inside organizations, the more likely you are to see decisions influenced by politics, incentives, personalities, and self-preservation rather than whatever principles happen to be written on the company website. You eventually encounter situations where talented people are overlooked, where questionable behavior is tolerated because someone delivers results, or where protecting an organization becomes more important than confronting something uncomfortable.
I’ve seen enough of that in my own career to understand the cynicism, but strangely, it has probably made me believe in good leadership more rather than less.
The reason is that the contrast becomes clearer. I remember the leaders who gave people credit when they could easily have taken it themselves, who challenged decisions privately because they believed something wasn’t right, who protected their teams without pretending their teams were perfect, and who were willing to tell someone a difficult truth without trying to diminish them in the process. None of those behaviors required a leadership framework or a presentation about values. They were simply choices people made when there was often an easier choice available.
A decision with a visible cost
Consider an illustrative situation: an experienced developer estimates two weeks of work, while a customer has been promised delivery in one. There is no extra team waiting to help. The uncomfortable part is not discovering that the promises conflict. It is deciding who carries the cost of correcting them.
A leader could quietly expect overtime, describe the developer as uncommitted, or keep both sides believing their version of the plan. None resolves the disagreement. A more useful response puts the constraint in the open: what can be delivered safely in a week, what must move, and who will explain the change to the customer?
Protecting the team does not mean pretending the estimate cannot be questioned. Ask how it was formed and whether a smaller release would still help. The distinction is between examining the work and making a person absorb a promise they did not make.
Care and accountability belong together
The same distinction applies when someone really has made a mistake. Being fair is not the same as avoiding a difficult conversation. Describe the behavior, its effect, and the next expectation. Give the person room to explain what happened before deciding whether the problem is judgment, skill, workload, or an unclear instruction.
For example, a missed handover needs more than a reminder to communicate better. The team needs to know what information the next owner lacked, where it should have been recorded, and when responsibility was supposed to transfer. A specific repair makes the standard usable. A vague criticism leaves everyone guessing.
Fairness also has a consistency test. Would the response be the same if the mistake came from the strongest performer or the newest team member? Context matters, but exceptions should be explainable without relying on somebody's status.
Repair is part of the job
I’ve also learned that leadership isn’t a permanent characteristic someone acquires with a title. People can lead brilliantly in one situation and poorly in another. I’ve certainly made decisions I would handle differently today. That is part of why I’m reluctant to divide the professional world neatly into good leaders and bad leaders. Most of us are probably a collection of both, hopefully improving the balance with experience.
An apology matters more when it changes the next decision. If a leader overruled an estimate without checking the assumptions, the repair might include correcting the commitment and inviting technical review before the next promise. If credit was assigned unfairly, correct it with the people who heard the original account, not only in private.
Those actions are rarely dramatic. They can be uncomfortable because they make the leader's part in the problem visible. That is also why they are useful: the team can see a standard being applied upward as well as downward.
A standard small enough to use
A practical review after a difficult week can be brief. Who carried the cost of the decisions? Which commitment needs correction? Did anyone receive criticism without a clear next step? Was there a contribution that deserved recognition? These questions do not require a new leadership program; they require a willingness to act on the answers.
What I don’t want to lose is the belief that the way people are treated matters, particularly when things are difficult. Success can make almost anyone look like a good leader for a while. The moments that have taught me the most are the ones where there was something to lose by doing the right thing. Those are also the experiences that have most influenced the kind of leader I still want to become.
Good leadership is easier to believe in when it can be described as behavior rather than personality. A promise corrected, a difficult truth explained, and a fair expectation followed through are small enough to observe and important enough to repeat.
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