Category: Trusted Strategic Advisor’s Fieldbook

The Five Imperatives of the Trusted Strategic Advisor

Becoming a Trusted Strategic Advisor imposes five crucial imperatives:

  1. Jettison staff-based assumptions.
  2. See the whole board.
  3. Tolerate constructive ambiguity but strive for certainty.
  4. Maximize your prerogatives.
  5. Develop real expertise beyond your staff function.

Jettison Staff-Based Assumptions

One of the most profound underlying concepts of success as a Trusted Strategic Advisor is the imperative to set aside all your staff-based assumptions and orient your life, your thinking, and your recommendations to the perspectives, viewpoints, and issues of those you advise.

See The Whole Board

If you have been tutored by or have taken classes from a skilled chess player, you know that one of the most important lessons is to keep the entire board in mind. You have to look at the whole board constantly as you plan and make your moves, assessing, analyzing, and forecasting the other moves that could result.

Tolerate Constructive Ambiguity, but Strive For Certainty

Consultants and advisors are fundamentally option and alternative finders rather than solution finders. This is because leaders recognize that having a solution is oftentimes the least of their worries. What really matters is finding a process to get to something that works-almost anything that works. This is another area where the trusted advisor plays a crucial role.

Maximize Your Prerogatives

Being influential means having power. Getting things to happen today, when you want to or need to, is about creating immediate, visible impact through actions or decisions by the boss.  You can also choose to be influential over longer time frames-whichever strategy best fits the objective you seek to achieve.

Develop Real Expertise Beyond Your Staff Function

If you want to gain access beyond routine staff consultations by operating executives, you must possess, perhaps above all else, some real, recognizable business expertise. This expertise generally needs to move beyond your area of staff knowledge. The reasoning is that most senior operators feel fairly confident of their knowledge base in your area and assume that your competence in that area comes with the territory. If you stay within the box of your staff expertise, you will be called only when the boss thinks that your staff expertise is required, usually, it’s to validate something he or she already wants to do in your area.

Pick a topic or field of interest you like at work or in your industry. Develop real expertise, it’s how you earn entry to the top levels of your organization.

*©2006-2025, James E. Lukaszewski, “Why Should the Boss Listen to You, The Seven Disciplines of the Trusted Strategic Advisor, page xxxv-xlii,” Josey Bass. Contact the copyright holder at jel@e911.com for information and reproduction permissions. Editing or excerpting forbidden.

The Lukaszewski Trusted Strategic Advisor Fieldbook

Chapter One

  1. Strategists, Advisors and Leaders are Constantly Searching for Unique Skills
  2. The 11 Action Principles of The Trusted Strategic Advisor
  3. Eight Tests That Prove You are a TSA
  4. Do You Really Have the Stomach to be a TSA?

Welcome

Welcome to the first chapter of the first edition of the Trusted Strategic Advisor Fieldbook. I’ve been meaning to develop this document for many years. This Fieldbook is meant to be just that, things that work in the field. I will publish soon the table of contents for this Fieldbook and ask you to critique it and make additional topic suggestions. Here we go.

 The Constant Search for Unique Skills

The higher one rises in management and leadership the more difficult it is to locate and be helped by people committed to your interests, needs and goals. Lots of competing agendas at the top.

Senior people and leaders are constantly in search of:

  • Individuals with common sense.
  • Individuals with a sense of humor.
  • Individuals with their ears to the ground.
  • Individuals who can tell which way the wind will blow.
  • People who can spot the stinkers, fakers, and charlatans.
  • People who are iconoclasts, rule breakers, and productive mistake makers.
  • Pragmatists to help manage the inherent over-optimism of leadership.
  • True strategists, inconsistent thinkers who ask the toughest questions.
  • People who can find and tell the truth, first, fast, always.

Where do you fit among these categories? Few people have all of these attributes but most all these traits can be learned. Plus, an even bigger question for you: Are you willing to change yourself for the benefit of others, from their perspective?

One of the most intriguing aspects of being a Trusted Strategic Advisor is developing the habit and the skill of looking at the world through your boss’s eyes. Then, helping the boss see their world more clearly. The lessons are:

  1. Whatever your area of special expertise, chances are the boss needs more from you, beyond your knowledge base.
  2. The boss may ignore your advice, meaning seeking different advice or advisors, or just the notion that other kinds of advice are needed.
  3. Will you expand your vision and thinking beyond what you came with?
  4. Are you willing to find the help needed, even if that reduces your presence in the C suite?  If you do this your time in the C suite will expand.

Among the greatest skills of a Trusted Strategic Advisor is the ability to anticipate the direction of leadership thinking and be ready to walk down whatever road is chosen very quickly or block the new direction with a better direction.

The TSA’s Working Principles

  1. Always say things that matter.
  2. Say less but make your messages more important.
  3. Talk to time; Three-minute bursts, 450 words
  4. Write less but make your words powerful, compelling, and memorable.
  5. Write to time; one page, one side; beginning to end, 450 words, 3 minutes.
  6. Suggest less. New ideas are less valuable than getting yesterday’s lingering problems solved.
  7. Be worth hearing because you are memorable, sensible, and say what needs to be said, when it needs to be said.
  8. Being memorable means suggesting crucial, incremental, achievable options from which leaders will choose . . .or reject.
  9. Provide three options every time: do nothing, do something, do something more. Use the three-minute drill. 
  10. Remember, they choose the option, unless they choose to do something else. Be the first to support their initiative, or to constructively challenge.
  11. It’s their bus. You are a valued guest until you’re not.

Eight Tests You’ll Have to Pass that Demonstrate
You Have Become a Trusted Strategic Advisor:

  1. People remember what you say and quote you when you’re not in the room.
  2. People quote you in your presence.
  3. People tell your stories and share the lessons, giving you the credit.
  4. People tell your stories and share your lessons as though those stories and lessons belonged to them.
  5. Others seek your opinions and ideas, then share their agendas and beliefs with you in the hope of influencing you to influence the behaviors and decisions of others more senior than either of you.
  6. The boss asks others to run their stuff by you before running it by them.
  7. You are among the first called and the last consulted for important decisions.
  8. Meetings are held up waiting for you to arrive to make important contributions or interpretations of current events.

Before You Seek to Become a Trusted
Strategic Advisor, Ask Yourself:

a. Do I have the stomach for the intense, conflict-ridden and often confrontational environment in which decisions are made at the senior levels of organizations?

b. Can I dispassionately assess the strengths, weaknesses, opportunities, options and threats to the organization from a variety of useful constructive perspectives (more than just the media)?

c. What is the real expertise, beyond my area of staff knowledge, that I bring to those who run my organization?

d. Will I commit to mastering the seven disciplines of the trusted strategic advisor and harness their power for my success and the success of those I advise?

e. How do I credibly and convincingly answer the question, “Why should the boss listen to me?”

Copyright © 2025, James E. Lukaszewski. All rights reserved. For permission to reproduce or quote, contact jel@e911.com.