I often ask clients, "Who's the best boss you've ever worked for, and why?"
The answers are always interesting and enlightening, but one surprise is that many people want to talk instead about a boss they would never want to work for again. A boss who was ridiculously demanding. Impatient, curt, closed, or even volatile. Exacting, sometimes exhausting, lacking in EQ.
Yet, as we continue talking about these "bad bosses," something else often surfaces: my clients conclude that they learned more from that difficult manager than from many of the "good bosses" before or after.
The reality is, the leaders who shape us most are not always the ones we admire or appreciate while we're working for them. Often, their lessons emerge years later, when we start leading others ourselves.
Major John Howell of the U.S. Army Reserve is a good example.
Early in his career, Howell served under a commander whose expectations were unrelenting. Meetings on simple communications turned into critiques of font sizes, formatting, and even Oxford commas. Howell found his manager's attention to detail excessive and frustrating. Like many talented young professionals, he wondered why so much energy was being wasted on seemingly trivial matters.
Years later, after assuming command himself, Howell found himself using many of the same templates, standards, and disciplines that had once irritated him. What had felt like needless perfectionism now looked like professionalism. The lessons had outlasted the frustration, and he came to an insight that has stayed with him ever since: the devil really is in the details. Leaders who fail to get the small things right eventually discover that the big things have a way of going sideways.
Major Howell recently shared this story with me, and it struck me as a useful and portable lesson for anyone working under a demanding leader. Not every difficult boss is a good boss, but neither is every uncomfortable experience a bad one. The challenge is figuring out what to learn from a leader without feeling obligated to copy how they led.
Demanding leaders don't always communicate well. They may overcorrect, obsess over details, or deliver feedback in ways that discourage more than inspire.
But buried inside imperfect delivery is often an important standard. Howell eventually realized that his commander wasn't really teaching punctuation; he was teaching precision, discipline, and pride in one's work. Those lessons happened to arrive as commas and formatting, and they didn't land as smoothly as Howell would have liked, but in hindsight, the takeaway was powerful.
Nearly every executive I've ever coached can tell a similar story about a tough manager. A CFO I work with learned extraordinary financial discipline from a CEO who questioned every number. A senior consulting partner became an exceptional communicator because a demanding chairman routinely dismantled his presentations. Neither enjoyed the experience, but both became substantially better leaders because of it.
And I've noticed an interesting pattern over the years: accomplished executives rarely imitate their prior bosses. Instead, they take pieces from each boss they've worked for, keeping what worked and dropping what didn't. The CFO who learned extraordinary discipline didn't become impossible to work for—in fact, today she's legendary in her organization for developing talent. The consulting partner who learned precision was never demeaning.
Of course, not every hard-driving manager deserves admiration.
One of Howell's most valuable insights was recognizing that demanding leadership is not the same as toxic leadership. This distinction became clear one weekend when his commander called with a non-urgent work request, and Howell respectfully explained that he couldn't respond immediately because of family commitments.
Instead of barking back, his commander accepted the boundary and deferred the task to the following week. Looking back, Howell told me he had expected a very different reaction. Until then, he had interpreted his commander's relentless standards to mean that nothing less than complete availability would ever be acceptable. Instead, he discovered that his commander could demand excellence while still respecting judgment, boundaries, and the things that mattered outside of work.
There is a big difference between leaders who make us uncomfortable because they demand excellence and leaders who diminish the people who work for them. Demanding leaders may frustrate us, stretch us, and occasionally make us wonder whether their standards are reasonable. Destructive leaders leave damage behind. Learning to tell the difference matters.
A demanding leader will expect excellence, accountability, and responsiveness. Healthy leaders also recognize reasonable boundaries and respect people as human beings. Destructive leaders do not. They may use high standards as an excuse for behavior that ultimately makes people—and organizations—less effective.
Many young professionals assume they must either tolerate everything or quit. But as you grow and evolve, try to appreciate where the discomfort is helping you grow versus where you need to establish boundaries … and when the right answer is to walk away.
Major Howell's story has an unexpected ending, because his most potent insight came long after the working relationship had ended.
For years, Howell's resentment toward his former commander lingered. The two men had occasionally stayed in touch, with his old boss checking in now and then to see how he was getting on. And in time, their relationship evolved: the tension that had once defined their working relationship faded, and a genuine friendship developed in its place.
Then one day, his former commander called with news—a stage 4 cancer diagnosis—and he simply wanted someone he trusted to listen.
Looking back, Howell says one of his greatest regrets is that he held on to his resentment long after he had learned the useful lessons. Forgiveness did not require rewriting history or pretending the experience had been enjoyable. But at some point, his frustration had outlived its purpose.
The best leaders eventually learn to separate the experience from the lesson. When I asked Major Howell what he hoped younger professionals would take away from his story, he offered three simple principles:
Be willing to learn, even when the lesson doesn't come wrapped in a pretty package.
Know the difference between demanding and destructive leadership.
Don't allow negative feelings to live beyond the lesson.
Not every difficult boss is worth staying with. Sometimes the right answer is to leave. Sometimes it is to establish healthier boundaries. But sometimes the greatest opportunity is to ask a different question: "What can I learn from this person despite the things I would never want to emulate?"
Years after the meetings, the corrections, the frustration, and even the resentment have faded, Howell leads differently because of that commander. Perhaps that is a more useful test of a great boss: not whether you always enjoyed working for them, but whether they prepared you for responsibilities you had not yet imagined.
This article was originally published on Forbes.com