One of the most important roles of the trusted strategic advisor is to ask constructive questions that help broaden understanding and move processes and decision making to the next level.
Too often, staff tend to use questions as a means of demeaning, maligning, or harming the advice of other advisors. Here are some examples:
“Why am I/we just hearing about this now?”
“Where is the justification for this request?”
“Where did this come from? How many have done it successfully before?”
“Why wasn’t this circulated earlier for more thorough consideration?”
“Shouldn’t this have gone through IT, finance, or strategic planning first?”
“Who authorized this much off the reservation effort?”
I often refer to this as “Death by Question.” If this is your approach, you need to end it immediately. Insults and needlessly combative negative opposition through questioning are always remembered. What goes around will come back around. Negativity creates needless victims and active adversaries. These injured individuals live forever and always resurface at the worst possible times.
Even though you learn that the senior executive environment is fairly combative and confrontational, your goal has to be to preserve loyalty, develop constructive next steps, and convert criticisms into constructive questions.
Ask Managerially Relevant Questions First
Managerially relevant questions are designed to foster discussion and the productive exploration of ideas. They bring more critically essential understanding to the boss. Here’s a list of those kinds of questions, which are almost always relevant:
- How does the current situation affect strategy?
- Which management mistakes could change the strategy?
- What steps can we take to gain employee commitment to the changing circumstances that are causing some of the problems we must now face?
- What strategies are available to us to keep shareholder interest aligned with our goals?
- Can management make the tough decisions and act quickly enough to turn a problem situation into an opportunity or at least into a mitigative circumstance?
- What resources can management allocate now to deal with the issues at hand or to resolve matters in ways that align with our strategy?
- What have peer companies done in similar circumstances? Do we care?
- How will the present circumstances affect our ability to research and develop new products, services, and ideas?
- Is this a situation that requires adaptation or dramatic shifts and changes?
- What nonfinancial factors are of greatest concern? What about the direct financial factors?
- Will customer satisfaction be adversely affected?
- What are the compliance and ethical implications of the current situation, and what remedial steps will be necessary?
- Have any rules, regulations, or laws been bent, broken, or compromised?
- Are there other experts we need to recruit?
Be a Constructive Skeptic
If many of these questions seem confrontational, it’s because they are. This is part of your role as a constructive skeptic, as a productive, constructive questioner. It is a part of the rough-and-tumble world of a top strategic advisor. Get comfortable asking questions that have a constructively confrontational (rather than negative) tone. Every idea can be subject to a clash of thinking and alternative comparisons.
As Always, Have an Answer in Mind for Every Question You Question
In terms of operations, asking questions is an excellent method for triggering incremental improvement. However, the job of the trusted strategic advisor is to simultaneously develop answers and answer strategies.
*©2006-2026, James E. Lukaszewski, “Why Should the Boss Listen to You, The Seven Disciplines of the Trusted Strategic Advisor, pages 92-94,” Josey Bass. Contact the copyright holder at jel@e911.com for information and reproduction permissions. Editing or excerpting forbidden.
