There’s no algorithm to apply, no flow chart to follow, no equation to run to get a perfect hit rate on the decision to develop or replace. The best executives care deeply about their people, and that’s why they often wait too long. But they also improve their judgment over time.

Which brings us to a crucial question: How do you know when you’ve crossed the demarcation line, when it’s time to make the shift from “develop” to “replace” for a key seat? I’ve come to believe the best approach is to ask considered questions and let those questions guide you to an answer. I’ve distilled years of reflection down to seven questions that I offer here to stimulate your thinking when you face the “develop or replace” conundrum. To be clear, these aren’t a prescription; you might come up with only one concern and decide to replace, or you might come up with six concerns and decide to develop.

• Are you beginning to lose other people by keeping this person in the seat?

The best people want to work with the best people, and if they sense chronic tolerance for mediocre performance in key seats, they might begin to vote with their feet. Worse, if you tolerate high-performing people who behave contrary to your stated core values, the true believers will begin to lose heart and become cynical, and some will leave. There’s no better way to destroy a great culture than to retain people in key seats who fail to perform or run roughshod over the company’s core values. roughshod over the company’s core values.

• Do you have a values problem, a will problem, or a skills problem?

If someone in a key seat behaves consistently or flagrantly contrary to the core values of the enterprise, the best leaders replace them. If someone passionately embraces the core values of the enterprise and also has the indomitable will to do whatever it takes to master his or her seat, you can be more patient before reaching a decision to replace them in that seat. The hardest call comes with the question of will. Does the person lack (or has the person lost) the will to develop to meet the demands of the seat? If not, can you ignite their will?...

• What’s the person’s relationship to the window and the mirror?

The right people in key seats display window-and-mirror maturity. When things go well, the right people point out the window, giving credit to factors other than themselves; they shine a light on other people who contributed to the success and take little credit themselves. And when things go awry, they don’t blame circumstances or other people for setbacks and failures; they point in the mirror and say, “I am responsible.” People who look in the mirror—who always ask, “What could I have done better? What did I miss?”—will grow. People who always point out the window to explain away problems or affix blame elsewhere will be stunted in their growth.

• Does the person see work as a job or a responsibility?

The right people in key seats understand that they don’t have “jobs”; they have responsibilities. They grasp the difference between their task list and their true responsibilities. A great doctor doesn’t merely have the “job” of performing procedures but embraces responsibility for the health of the patient… Every person in a key seat has a broader responsibility than a task list, and the right people never hide behind “I got the tasks done” as an excuse for failing to deliver on the broader responsibility.

• Has your confidence in the person gone up or down in the past year?

Just as a company’s stock price rises or falls as investors gain or lose confidence in the company’s growth and performance, confidence in a person also rises or falls based on his or her growth and performance. The critical variable is the trajectory of that confidence over time. When someone says, “Got it!” do you increasingly set your worries aside or do you increasingly feel the need to follow up?”

• Do you have a bus problem or a seat problem?

Sometimes you might have a right person on the bus but in the wrong seat. You might have put the person in a seat misaligned with his or her capabilities or temperament. Or perhaps—and this happens frequently in high-growth companies—the demands of a seat might have grown to outstrip the capabilities of the person in that seat.

• How would you feel if the person quit?

If secretly relieved, then you might have already concluded that he or she is a wrong person on the bus. If genuinely distraught, then you might well believe that he or she is still a right person on the bus.

So the dating phase of any potential acquisition is crucial. You have to check the sink for dirty dishes. You have to spot the toenail on the dining table. Look at the reporting structure and the way they hire and fire employees. Dig into what perks everyone gets. Talk about management philosophy. Make concrete plans for exactly what’s going to happen postsale.

Are you going to integrate or keep your cultures separate? What will you do about overlap? Where will this team go? Who will work on this product?

But always know that you won’t be able to predict the future. Things will change—maybe in your favor, maybe not. And so, eventually, you just have to do it. Sign on the dotted line. Trust that it’ll work out.

My advice is to always be cautiously optimistic. Trust, but verify.

Assume people have the best intentions, then make sure they’re following through on them. And take the risk. Leap. Buy the company. Sell the company. Or do neither. Just follow your gut and don’t be scared (or, rather, be scared but make the decision anyway).

The decision to disrupt businesses that are fundamentally working but whose future is in question—intentionally taking on short-term losses in the hope of generating long-term growth—requires no small amount of courage. Routines and priorities get disrupted, jobs change, responsibility is reallocated. People can easily become unsettled as their traditional way of doing business begins to erode and a new model emerges. It’s a lot to manage, from a personnel perspective, and the need to be present for your people—which is a vital leadership quality under any circumstances—is heightened even more. It’s easy for leaders to send a signal that their schedules are too full, their time too valuable, to be dealing with individual problems and concerns. But being present for your people—and making sure they know that you’re available to them—is so important for the morale and effectiveness of a company.

Culture isn’t just one aspect of the game - it is the game,” Gerstner says. “In the end, an organization is nothing more than the collective capacity of its people to create value. Vision, strategy, marketing, financial management - any management system, in fact - can set you on the right path and can carry you for a while. But no enterprise - whether in business, government, education, health care, or any area of human endeavor - will succeed over the long haul if those elements aren’t parts of its DNA.”

Chris Lofgren, chief executive of Schneider National, the large transportation and logistics company believes that “culture is a foundation upon which you build your long-term strategy. If you build a strategy that isn’t consistent with the culture, it isn’t going to work.

But what do we do to our organizations when we define ourselves by the existence of the Other? When we presume that the competitor in the lane next to ours is wrong, bad, or a threat, we are allowing our deepest fears about our own inadequacy to stand in as our ‘vision statement’ and ‘strategic plan.’ An unintended, whispered consequence is that our colleagues—our friends down the hall with whom we built this thing, this product, this service, this company—may fear that they, too, are ‘them.