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This column is brought to you by arrangement with The New York Times Syndicate. You can e-mail the authors at winning@nytimes.com, include your name, occupation, city and country.

What criteria should be used to determine if you have been with the same company too long?
– Jason Morrow, Salt Lake City

Your question reminds us of a friend of ours, an investment manager at a highly regarded company in the Midwest, who drove to work one morning, parked his car in the usual spot and then found he simply could not bring himself to get out. "I guess I stayed on the farm one day too long," he joked later. When we asked him what went wrong, he answered, "It wasn't one thing. It was everything." No wonder he drove home and called in his resignation.

Obviously, most people don't decide they've over-stayed at their companies in such a dramatic fashion. Usually, angst about work creeps in, and then builds until it consumes you. And that can happen early or late in a career. Gone are the days when, after graduation, you took the best available job and stayed for as many years as you possibly could stand, frustration be damned. These days, it is not unusual to hear of perfectly legitimate careers built on multiple job stints.

So, to your question, how can you tell when it's time to move on? We wouldn't set out specific criteria as much as offer four questions to help sort out an answer. The first is so simple it almost goes without saying, but the fact that a lot of people don't confront it, including our friend who ended up stuck in his car – a Harvard MBA, by the way – suggests we go ahead and put it out there.

Look, do you want to go to work every morning? This is not a matter to be over-thought. Does the prospect of going in each day excite you or fill you with dread? Does the work feel interesting and meaningful or are you just going through motions to pull a paycheck? Are you still learning and growing? We know of a woman who worked in consulting for seven years. She loved her firm and had originally planned a career with it, but suddenly started noticing that she wished every weekend was five days long. "I felt like we were putting together massive books in order to make recommendations to people who knew more than we did," she said. "Every day at the office, I felt a little bit more of a hypocrite." She now happily works on the ‘front lines’, to use her phrase, in the marketing department of a retail company.

Second, do you enjoy spending time with your coworkers or do they generally bug the living daylights out of you? We're not saying you should only stay at your company if you want to barbecue with your team every weekend, but if you don't sincerely enjoy and respect the people you spend ten hours a day with, you can be sure you will eventually decide to leave your organisation. Why not make the break sooner rather than later, and start cultivating relationships at a company where you might actually plant roots?

Third, does your company help you fulfil your personal mission? Essentially, this question asks whether your company jibes with your life's goals and values. Does it require you, for instance, to travel more than you would like, given your chosen work-life balance? Does it offer enough upward mobility, given your level of ambition? There is no right or wrong answer to questions such as these, only a sense of whether you are investing your time at the right or wrong company for you.

Fourth, and finally, can you picture yourself at your company in a year? We use that timeframe because that's how long it usually takes to find a new, better job once you decide to move on. So peer, as best you can, into the future, and predict where you will be in the organisation, what work you will be doing, whom you will be managing and who will be managing you. If that scenario strikes you with anything short of excitement, then your runway is too short. Or put another way, you're just about to stay too long.

To be clear, we're not suggesting people quit at the first inkling of discontent. No matter where you work, at some point you will have to endure difficult times, and even a deadly dull assignment, to survive a crisis or move up. But it makes little sense to stay and stay at a company because of inertia. Unlock your door and get out.

I sit on a board with two members who, for the past year, have said and done very little. Regardless, both were just re-elected unanimously with the support of the nominating committee. What's your take?
– Name Withheld, New York

So, two seat-warmers on your board were just re-elected unanimously, you say? Doesn't that mean you voted for them too? If so, don't worry. You're definitely not the only board member in history to endure an ineffective or otherwise dysfunctional fellow director.

Not to slam boards. As a whole, they add real value. But boards frequently tolerate troublesome performance from one or two of their members; it's simply too time-consuming or impolitic to eradicate. And that, unfortunately, is why too many boards – in both the public and private sectors – don't make the full contribution they could, and should.

To be clear, we are not talking here about board behaviour that is criminal. With a few famous exceptions, boards will remove anyone who does not adhere to the law. No, we're referring to the types of boardroom behaviours that are perfectly legal but perfectly destructive as well. There are at least five by our count.

Let's start with the type of bad board member your letter describes: 'The Do-Nothing'. Some of these individuals are too busy with their own companies, other directorships or their lives in general to care about your particular board. Some don't have enough skin in the game to work up authentic interest. And still others lie low for job security.

At US$25,000 to US$100,000 a pop in the corporate world, being a director can be very good money. In the private sector, prestige is often the reward. And so Do-Nothings rarely challenge or probe at meetings. Nor do they venture out into the field to take the pulse of the company, checking to make sure that what they are hearing in the boardroom about values and strategy matches what employees are feeling.

Do-Nothings are awful but not nearly as dangerous as type two in our taxonomy, 'The White Flag'. These people live in fear of being personally tainted by any kind of controversy, such as a class action lawsuit or activist protest. They lack courage – a key characteristic of any good board member. With every public or private challenge, they pollute the boardroom by hyperventilating for a settlement, even if it means selling out on principle just to get out of the crosshairs.

Sure, a board must settle a dispute on occasion, but never before seeing the organisation through a thoughtful discovery of the facts. Such a process creates a culture of trust between management and the board, and it is only in such an environment that risks can and will be taken.

'The Cabalist' is the third type of bad board member. This is the director who sits quietly in meetings – in fact, a Cabalist often goes along with the prevailing side – but then takes up a cause behind the scenes, building constituencies to achieve another agenda, namely his or her own.

In many cases, good board members shut down such practitioners of palace intrigue. But sometimes, a board's Cabal is its own executive committee. The result is a controlling, secretive board-within-a-board that turns other directors into second-class citizens.

Good directors focus on big picture issues like succession and strategy. By contrast, consider our fourth offender: 'The Meddler'. Instead of meeting with high-potential talent and discussing industry dynamics, meddlers get all mucked up in operational details. They seem oblivious to the fact that board members are there for their wisdom, sound counsel and judgment, not the day-to-day running of the business.

And then, finally, there is 'The Pontificator'. This is the self-important bloviator who cannot get enough of his own voice, especially when it is opining on 'matters of state', such as world events, social trends, the company's history, or his particular area of expertise. Like Meddlers, Pontificators distract the boards from the real business before them, and enervate their colleagues in the process.

As a board member, it is easier, of course, to let a couple of Do-Nothings stand around until retirement and to tolerate a few White Flags cowering while the rest of the group handles each crisis. It is easier to try to isolate or work around Cabalists and ignore Meddlers and Pontificators.

But imagine how much better it would be if nominating committees, usually just focused on vetting potential members, faced into the hard cases right in front of them. After all, no one can keep a board on its best behaviour but itself.

I find that, in running my business, I am making many decisions alone. I know that can't be good. How can a leader keep from becoming isolated?
– Arthur Lakiisa, Kampala, Uganda

It's something of a coincidence that your question arrived just as two CEOs, Chuck Prince of Citigroup Inc. and Stan O'Neal of Merrill Lynch & Co., were cast out of their jobs and publicly crucified for the 'sin' of surprising the market with bad results.

Now, we don't know if either CEO had become isolated from the people in his respective organisation who knew trouble was looming. But the magnitude of the 'expectation gap' suggests both CEOs were blindsided, at least to some degree, by their company's poor performance. Like you, perhaps, they were lonely at the top. And perhaps, like you, they knew it wasn't good. They just didn't catch the problem soon enough. That can be a fatal mistake.

In fact, when you're a leader, the last thing you should let happen is getting pushed into an ivory corner, where you end up plucking decisions out of the air or pecking at a keyboard. And yet, obvious as that may be, there's something about becoming a boss that incontrovertibly lends itself to isolation. It's as if every natural force is working to 'protect' you from reality. Good news travels up fast, but bad news festers, down in the trenches with the people hoping they can make it go away before anyone notices.

At the same time, there is the propensity for leaders to surround themselves with 'yes types', who make themselves all the more welcome with the assurance, "Don't worry, everything is under control." In most companies, of course, that's rarely the case. This is why you have to get aggressive about fighting creeping insularity.

How? There are some universal techniques. For instance, any leader can leave the office – and should. Every day ‘embedded’ is a day you're not out learning about your own people and processes, not to mention market realities. Visit stores, trading floors, regional offices or factories. And visit customers, not just when they call to complain, but several times a year.

Just as important as getting yourself outside is whom you surround yourself with inside. Sure, most leaders have a standing group of advisors comprised of direct reports. But such committees can easily fall into a grind, where dialogue devolves into them telling you what they assume you want to hear.

You can beat that dynamic by reaching into the organisation to create a revolving kitchen cabinet, filled with the smart, edgy, self-confident individuals who have in-the-fingertips expertise.

Try to avoid the usual suspects; seek out people tucked in areas or functions out of your direct line of sight, and make especially sure you're gathering people who are sworn change agents and inveterate cranks. Change agents are usually the first to sense a shift in the market. And cranks, well, yes, they can be annoying, always nattering about how the ship has cracks. But the best of the lot are usually onto something. Ignore them at your peril. Finally, leaders can prevent insularity by doing something that will surely feel, at first, terribly counter-intuitive. They must act like the dumbest person in the room.

Sure, as a boss, people will turn to you for all the answers, and you'll want to respond in kind. But instead, show people that your job is to have all the questions. Greet every decision, proposal or piece of data with "What if?" and "Why not?" and "How come?" Then wallow in the answers, dropping every artifice of formality during the ensuing conversation and debate.

It won't happen overnight, but in time, this approach will breed a culture of vigorous engagement, drawing the best ideas out of the group, and yes, even surfacing the buried crisis that is just about to blow.

Which brings us back to Chuck Prince and Stan O'Neal. Again, we're not saying either CEO suffered from isolation. We just don't know. But the market's surprise at their poor results begs a question that every leader must ask: Am I alone up here? The answer can never be yes.