Great Employees Show Good Judgement (Behavior #4)

The ability to make good judgements is as much an art as it is a science.  Sure, it requires a systematic examination of facts and impacts, but it also requires excellent situational awareness, a modicum of emotional intelligence, and an ability to stay out of political hot water.  In short, if you don’t have the “knack” for quickly making good judgements, you probably never will.  But don’t despair.  By applying tried and true techniques and taking your time with your decisions, recommendations, and utterances, you can avoid the exhibition of bad judgement – a curse that otherwise would keep you forever mired among the masses of “average” employees.

What is meant by Good Judgement?

Good judgement is the making of smart, perceptive, and insightful decisions and observations.  It also involves an appreciation for context, timing, and situational awareness, in addition to basic factual correctness.  While only a portion of this is an exact science, pure precision isn’t required.  Get things directionally correct, and you’ll be doing better than the majority of subordinates.

Just the facts, ‘mam

Let’s start with the basics – getting the facts right.  It has been said that the language of business is “money.”  To that I would add “risk and uncertainty.”  Almost every business decision can be reduced to these two coordinates.  Want to recommend an investment?  Calculate the return on investment, and estimate the chances the project will jump the tracks.  Think your group needs to hire an additional person?  What’s the payback and how likely is it that you will fail to recruit the kind of person you need?  Think the company should change some element of their strategy?  You’ll need to build your case in terms of monetary opportunities and uncertainties.

More than anything else, exercising good judgement means that your recommendation or selected course of action can pass the smell test when it comes to this pair of factors.  Of course, the boss will expect this from all employees, stars or those inhabiting the middle of the pack.  If you don’t learn to deliver competence in this part of decision-making and recommendation-developing, you’ll quickly fall into the “needs help” subordinate category, code for “ditch this employee at your earliest opportunity.”

I recall a peer who was a master of spreadsheets, an expert at making sure any project he advocated had the proper, attractive ROI.  The problem was his analysis was often “steered” by the conclusion he wanted to reach.  A little tweek here, an adjustment there, and voila, the project magically made the corporate hurdle rates.  Once launched, however, his projects had a bad habit of widely missing the forecast.  The conclusion – while he knew how to perform the financial analysis, he completely blew the analysis of risks.  Over time, we all learned to distrust his judgement.

Beyond these basics, one must take other factors into account if one wants to become a great employee.


This factor includes things like company history, the past experiences of key decisions makers, and the current condition of the company.  For example, a bold plan to retool a company’s production process will likely not be well received if the last attempt at “bold retooling” was an abject failure.

Similarly, if your boss (or her boss, in bigger decisions) had a big, promising project recently go bad, it probably isn’t the right time to propose another one.

It sounds so simple, right.  But you might be surprised how often employees completely ignore context – either because they are blissfully unaware of it, or because they are so enthusiastic about their idea that they think context doesn’t matter.  Trust me, context always matters.


There is bad timing and good timing.  Bad timing occurs when the thing you want to recommend come at a time when the boss (or the company) isn’t in a position to say yes – no matter how “brilliant” it might be.  When the company is financially on its heels, better to avoid a proposal that requires a large, upfront cash outlay.  And don’t propose a major change in strategy a week after your boss had her strategy approved by the board of directors.

Good timing is basically the opposite.  Good timing is where a series of seemingly fortuitous events lead directly to the positive reception of your project or proposal.  One fellow manager I worked with successfully completed an acquisition that performed significantly above expectations.  It didn’t take him long to follow this up with several similar transactions.  He knew that at that moment, the door was open.  A few years later after another manager’s acquisition failed badly, it became almost impossible to get anything approved.

There is a time for everything.  Most children eventually realize there is a proper time to ask mom for a cookie, and other times when such a request is almost certain to be refused (like right before a meal).  Don’t be that employee asking for a corporate “cookie” when saying yes is impossible.

Situational Awareness

Usually, but not exclusively, situational awareness is about exercising one’s political senses.  Some employees are excellent politicians, while others eschew politics entirely, arguing that it “shouldn’t matter.”  Still others are sadly ignorant of the political environment, altogether.

A great employee factors corporate politics into their actions.  It is critical to understand whose ox you are goring and whose political success or failure your recommendation plays into.  Not only will you protect yourself from unforced political errors – such as the making of unnecessary enemies – but you’ll have a much better chance of getting your proposals put into action.  Bonus points for making decisions that actually enhance your boss’s image and informal power.

When not about politics, situational awareness can be as simple as demonstrating some emotional intelligence.  Read your intended audience and adjust your proposal (or withdraw it) when you pick up the wrong signals.  Alternatively, don’t be afraid to press your case when the opposite signs are present.

Why the Boss Needs you to Exercise Good Judgement

Bosses are almost always spread thin.  So thin, in fact that they simply cannot ride herd over every action their subordinates take.  An employee that demonstrates an ability to make good calls can be a tremendous asset to the boss, relieving her of the requirement for minute by minute observation and multiplying her group’s impact.  As a side benefit, such a person normally has a freer rein than her peers.

Employees that chronically make bad judgements suck up management time, and can be an embarrassment when they get things terribly wrong.

What a Great Employee should do.

Act cautiously.  Make sure the judgements passed, in the form of recommendations, proposals, decisions, or even comments, are well thought out and fit the standards of context, timeliness, and political reality.  Most importantly, demonstrate to your boss that you have the kind of judgement that he can rely upon, including offering up your insights and analysis for his review and critique.

Can You Take the Exercise of Good Judgement too far?

There may be a temptation for the prospective star to go hyper-conservative when attempting to exercise good judgement.  The old saying that one should, “keep your mouth shut and be thought a fool, rather than opening it and removing all doubt,” is bad advice, at least in this context.  While remaining silent rather than risking a mistake in your own decision making might keep you out of immediate trouble, it will also severely curtail your opportunity to make meaningful contributions.

There is a balance to be struck here, and while it is safer to err on the side of avoiding errors, one can’t simply clam up and meld into the herd – not and also distinguish oneself.  Someone who follows this path will never be seen by their boss as a great employee.


Great employees exercise great judgement in their recommendations, decisions, and even in their comments.  While getting the facts straightly translated into the language of management (money and uncertainty) is a start, the great employee also evaluates her contribution in terms of the organizational context, timeliness, and the political realities of the firm where she works.  Exercising great judgement is a force multiplier, freeing up the boss to spend time on tasks other than looking over a subordinate’s shoulder.  But the great employee can’t allow himself to slide into a pattern of avoiding judgments, fearing that an error will damage his reputation – this is a sure path to mediocrity.