“I keep six honest serving men they taught me all I knew, their names were what and where and when and how and why and who“      Rudyard Kipling

On many occasions in this series of articles, I refer to “Untested Assumptions”, as one of  a manager’s worst enemies.  Acting on untested assumptions can have serious consequences necessitating much undoing and significant embarrassment.  To avoid the problem, I recommended the artful use of QUESTIONS designed to put one’s assumptions to the test.

The ability to ask questions and the gut feel for where, when and for what purpose, however, is not as simple as it might seem.  Anyone reading the masterful use of the questioning art employed by Socrates in Plato’s “Apology”, is easily impressed for life by there power to uncover facts and the truth.  But few of us can aspire to reach the level of mastery the “Apology” depicts.

Like any skill, the harder we work at it, the more we practice it, the better we are likely to get. What follows are a few of my thoughts that will hopefully ignite your desire to evaluate your own questioning skills and design a plan to further develop them.

First, begin with the mind-set that as good a questioner as you may currently be, you can still get better.  I have known far too many people way to interested in letting others know what they think, than to take the time to elicit the different perspective and knowledge of others.  Do not be one of them.

Second, it is important to think carefully about what precisely you need to know in any given situation.  Not all questions are equally likely to serve your knowledge-gaining purposes, so be discriminating and try to avoid wasteful data excursions.

Third, in many situations, time permitting, you will benefit from questioning a variety of sources.  The best questioners are keen judges of who they need to question based on the issue at hand. You can generally take for granted that always talking to the same folks regardless of the issue, is not the best questioning strategy.

Fourth, the best questions are DIRECT, OPEN, and PROBING.  And the best questioners favor a SIMPLE VOCABULARY that leaves little doubt about what they are asking. Good questions reveal nothing about the questioner’s opinions, views, or potential bias and allow the answerer to respond in whatever way they deem best.

Fifth, good questions probe for FACTS not opinions. One needs to develop a keen ear for answers that appear to have little factual basis to support their assertions. There are far too many occasions where splendidly articulated points of view are exchanged with only the thinnest substantive support to back them up.  So learn to dig for the facts.

Sixth, always be aware that your use of direct, probing questions may strike those being questioned as threatening, intimidating, or presumptuous.  Your ability to read the verbal and non-verbal feedback your questions generate and willingness to refine your approach, will enhance your prospects of realizing your knowledge goal.

Finally, It is critical to know when to persist with your questions and when to stop.  The time constraints for action may dictate that stopping point.  But the pursuit of more information can also be used to put off unpleasant decisions or to procrastinate in hopes of avoiding a decision at all.  The best questioners generally have the knack for knowing when enough is enough.

UPDATED May 2026

Categories: Exercising Responsibility, Managing & Leading, Self-Management

Tags: advice for managers, advice for managers from managers, asking questions, best managers, decision making, effective management and leadership, effective managers and leaders, executive leadership, exercising authority, line management, management advice, Managing & Leading, Self-Management