Becoming an Effective Strategy-Led CEO Advisor

The Route to the Pinnacle

Source: Shutterstock, 2026

I have been a CEO advisor for much of my career and for the first third of it, Jonathan Goodman was the protégé with whom I worked most at Monitor. He has gone on to be a world-class CEO advisor himself, later at Monitor Deloitte and now as Founding Principal of JWG Advisors. So, I thought I would invite him to co-write this Playing to Win/Practitioner Insights piece called Becoming an Effective Strategy-Led CEO Advisor: The Route to the Pinnacle. And as always, you can find all the previous PTW/PI here.

The Stages of the Journey

When we reflect on our time advising CEOs, we realize that we both made multistage journeys from narrow and ego-centered to integrative and CEO-centered to become effective strategy-led CEO advisors. We use the term effective in honor of the greatest management thinker, Peter Drucker and his seminal book The Effective Executive. We strive for effectiveness in advising CEOs who similarly strive to be effective in the spirit of Drucker.

We see three sequential stages along the journey to becoming an effective strategy-led CEO advisor.

1) Strategist

Virtually everybody, including both of us, starts on this journey as strategists. Strategists, again including us, see their jobs as cracking the case for the client — whether CEO or other executive — by applying a set of strategy tools and frameworks, combined with analytical heft, to solve the strategy questions at hand.

We did that, often together from the late 1980s to the mid-1990s and mostly independently thereafter. We remember well working for the President of the Chemicals Division of Canadian conglomerate, Domtar, on two businesses, Sifto Salt, one of North America’s biggest salt companies, and Arborite, the leading Canadian high-pressure laminate company (Americans — think Formica or Wilsonart). We cracked both cases, helping the President solve the mystery of why Sifto’s profitability in the Great Lakes region was consistently higher than in the Mississippi Valley region, and coming up with an entirely different customer segmentation approach for Arborite (which is documented in a Harvard Business School case written by then-HBS professor and later Roger’s colleague at Rotman School, Anita McGahan).

Building your skills as a strategist is a good investment. Great strategists are valuable, well-rewarded and do interesting, fulfilling work.

However, the shortcoming is that strategists are often inclined to solve the problem that their strategy skills cause them to see as the critical one. That has its limitations — and both of us have experienced them. We both remember working diligently to help another client make a big decision. We tackled the question in a novel and creative way to understand it well and came up with what the future revealed to be unquestionably the correct answer.

However, the CEO made the opposite decision to our recommendation — and it was disastrous. The reason he did so was because we solved our problem, framed through our strategy lens — not the CEO’s problem, framed through his strategy lens. Consequently, our recommendation wasn’t compelling — even relevant — to him. We failed him as strategy advisorseven though we think we performed brilliantly as strategists.

2) CEO Strategy Advisor

In our view, CEOs must own strategy. They can’t be effective outsourcing to others the hard thinking on which strategy problems to solve and how to solve them. They can use internal or external strategy advisors to help them. But the CEO must be in charge.

This necessitates that strategy advisors to CEOs solve the CEO’s strategy problems — whether the advisor thinks they are the most important, or not. A strategy advisor must earn the trust of CEOs by solving their most important strategic problems. If they earn-in, strategy advisors will experience CEOs asking them — as trusted advisors — what they think are the most important strategy questions to tackle. CEOs won’t do so if the would-be strategy advisors operate narrowly as strategists.

Internalizing this insight spurred the development of the Strategic Choice Structuring Process (SCSP), which is designed to start from the client’s problem definition and focus on the logic of the client, the reservations of the client, and the client’s standard of proof. The strategic advisor to the CEO provides guidance through the process, providing perspectives and suggestions, but the eventual decision must be the CEO’s. The best CEO Strategy advisors recognize that their job is not to tell the CEO what to do, but instead to enable the CEO to make confident and wise decisions.

3) Strategy-Led CEO Advisor

But for some, like the two us, becoming a compelling strategy advisor to a CEO is not the ultimate destination. The ultimate destination, or pinnacle, is to become an effective CEO advisor, building upon, but not limited to, our strategy expertise, hence the term strategy-led CEO advisor.

Strategy is inherently integrative because strategy choices are connected to every other choice (regardless of whether they are termed strategic or not) and provide guidance and guard rails for other choices. Strategy serves as the connective tissue across layers of management and between functions and as the filter to distinguish opportunities from distractions. The easiest thing to do for a strategy advisor to CEOs is to remain narrow in the domain in which the strategy advisor can develop knowledge superiority: strategy.

But there are always integral links between strategy and other knowledge domains — whether technology, operations, human resources, public relations, peak performance, etc. And there are valuable professional advisors to CEOs with deep expertise in these domains — e.g., deal lawyers, investment bankers, executive recruiters, and crisis experts.

One approach is to declare the integration with those other domains/experts to be the CEO’s job, which limits an advisor’s utility. More helpful is to assist the CEO in those integrations. That would mean, for example, working to ensure that the HR folks and/or compensation consultants create a framework that reinforces the strategy, not inadvertently works against it. In M&A, it may mean working alongside investment bankers to help make sure the CEO does the right deal, not just any deal.

Making the Journey

The ultimate goal is to develop deep, two-way trust, which makes the relationship work better for both you and the CEO. It must be reciprocal. If it isn’t, the relationship is likely to become diminished, because the advisor will feel under-appreciated and/or the CEO will feel exploited. However, with mutual trust, CEOs and their strategy-led advisors can accomplish great things together over long periods — and avoid more of the pitfalls on the road to success.

Achieving that ultimate goal requires that the strategy-led CEO advisor embody three characteristics.

1) Curiosity

Strategy-led CEO advisors need to demonstrate deep curiosity about, and empathy for, the CEO, who is the ultimate integrator in the company. They need to be intensely interested in what the CEO is up against. Where are they in their journey as CEO? What pressures might they be feeling from the company, its situation, and key stakeholders? As a result, the advisor needs to listen first — enthusiastically and actively. The purpose of questions should be to deepen understanding, not argue logical positions. They must withhold judgement; otherwise, CEOs will self-censure and the advisor won’t get the full picture of what is on the CEO’s mind. And without that, the would-be advisor is merely a strategist.

2) Patience

Strategy-led CEO advisors need to show patience, which isn’t easy because most people who become good strategists tend not to be, precisely because they are used to coming quickly to strategic conclusions. In fact, throughout its history, the strategy consulting industry has made the ‘case interview’ its rite of passage. The candidate is given a strategy puzzle to solve in real-time. If the candidate can’t do it quickly and convincingly, there is no job offer forthcoming. So, strategists are programmed from inception to be impatient.

To become effective, a strategy-led CEO advisor needs to patiently earn in — that is, earn the trust of the CEO. Without patience, a strategist cannot progress to become a CEO advisor (let alone strategy-led CEO advisor).

3) Honesty

Along with showing curiosity and patience, strategy-led CEO advisors need to express honesty. When they have understood the CEO well enough and earned the CEO’s trust, they must confront the CEO’s views when necessary — to pierce the cocoon of sycophancy that surrounds CEOs. CEOs often tell us it is one of our most important contributions. They worry, probably rightly, that their own people won’t confront them when they are framing problems incorrectly, missing something, or on the verge of making a bad decision, even if the CEO would have wished they had. They tell us that they count on us to demonstrate courage, to be relentlessly honest with them — even if it feels awkward and risky.

Practitioner Insights

This piece is written from the perspective of two external strategy-led CEO advisors. But the same insights apply to any internal strategist who wants to grow to become an internal strategy advisor to the CEO or strategy-led CEO advisor.

Reaching the pinnacle is not for everybody — certainly not for the faint of heart. Being a strategist is a fun and rewarding career and for many, being a CEO strategy advisor even more so. That said, reaching the pinnacle as an effective strategy-led CEO Advisor takes sustained and determined personal investment.

To make the journey, it is important to serve and learn from the most sophisticated and demanding CEOs, which is hard — because they are demanding. But figuring out how to serve them is the best way to get on the right learning trajectory. Both of us have benefited from sparring with accomplished, confident CEOs who are formidable strategists and motivating leaders in their own right.

To be compelling you need to develop, and share cogently, your perspectives. It takes investment and commitment to hone your ideas over time, to capture the learning from the situations of which you have had the privilege to be a part, and to communicate effectively. From our earliest work together, we forced ourselves to write our perspectives to clients in memos, not to rely on power point slides or their historical equivalents.

To be effective, you need to develop tools for solving the problems that CEO clients regularly face. We did. There wasn’t a great process for CEO-led strategy, so we created it with the SCSP. There wasn’t a great tool for linking top level strategy choices to lower-level choices — hence Cascading Choices/Choice Chartering. You need to either adopt tools that enable you or create ones when tools are not available.

Ultimately, becoming and being an effective CEO advisor, requires knowing yourself. Doing so is necessary to develop and manifest, with integrity, the curiosity, patience, and honesty required. There are many ways to better know and understand yourself. We both experienced a fantastic organizational theorist, Chris Argyris, in our early years at Monitor, who helped us recognize that a core-building block for effectiveness is the capacity for self-reflection — to see one’s impact in interpersonal situations and commit first to improving ourselves — not to ‘fixing’ others.

Further, there are two books that have been influential for us on our journeys. One is for people regardless of their chosen career: On Becoming a Person by Carl Rogers, a pioneering psychotherapist. The other is targeted at business professionals: The Reflective Practitioner by Don Schön (a longtime thinking partner of Argyris).

Some of this advice may sound like it is only for wizened old people — which we both may be now (despite being young at heart). But by our early 40s, we were both strategy-led CEO advisors — and think our CEO clients would confirm that we were effective. In our 30s, we were still working along the path from strategists to CEO strategy advisors to strategy-led CEO advisors.

We have written this piece in the hope that with guidance that we didn’t have, you might make the journey faster, and maybe with fewer mistakes along the way!