Strategic Thinking for Managers: Managing Up, Stakeholders and AI

Strategic thinking: one range up

Strategic thinking is a skill you can learn. A table by Chris Williams helps make sense of it. It crosses two axes: spatial range, from the individual through the team, the division and the company to the world outside the company, and time range, from now through weeks and months to decades. On the table you can place an employee, a team lead, a C-level executive and a CEO. Most people think within their own range. To advance, you need to lift your head and think at least one range above: how what I do affects others and advances the organization’s goals.

When this becomes a habit, visibility in the organization improves. Not because you made noise, but because your impact is clear to those around you. Strategic thinking closed a series I wrote about advancing in an organization. Three more things that help you advance:

• Take on management tasks before the promotion. The work does not speak for itself. Managers have to believe you will also succeed at the tasks of the next role. Start with an open conversation with your manager about wanting to try. Then identify which important tasks are left aside because the manager cannot get to them. That is where the opportunity lies.
• Communicate your successes, in your own way. Promotion decisions are usually made two or three levels above you, by people who do not know your contribution in detail. Keep a living successes document, update in real time and not at the end of the year, and use a fixed format for the 1:1: what was completed, challenges for next week including proposed solutions, and a plan with priorities.
• Think in terms of skills, not experience. Ask yourself: in which situations do I act well even when there is no clear answer, which tasks am I trusted to close all the way, and what is the last thing I learned without anyone asking.

And don’t wait for the organization to train you. We moved from a world where whoever holds the knowledge and the answers is appointed to manage, to a world where the manager is the one who knows how to ask the right questions. Volunteer for the next complex project. Such projects let you learn by doing, and come with access to other managers and forgiveness for mistakes.

Entering a senior role: mapping before action

When entering a new management role, almost everyone has advice, and usually it is not relevant: be assertive, don’t share emotions, always know all the answers. That same week three completely different coachees conveyed the same difficulty to me. The common denominator: none of them stopped at the entrance to the role to map the role and the organization and build a work plan on that basis.

• What is the gap between expectation and reality?
• What do the employees and managers say?
• In which areas do I know I struggle?
• Which three big tasks will I choose for the coming quarter, and approve with management?

The real challenge arrives in the second management role. A director or someone more senior leads dozens or hundreds of people and is squeezed from every direction: expected to think at the macro level and to master the details, almost without support. Most companies invest in training first-time managers, and very little in senior managers, who advanced to get there on the run.

Managing up: even with a difficult manager

No relationship in an organization is more critical than the one between an employee and their manager. There are red flags worth knowing: a manager who is focused on himself and decides on personal considerations, a manager who does not support you and keeps you from resources, micromanagement, and an inability to listen or accept feedback. But it takes two to tango. You may be the employee who is hard to trust, which is why your manager is controlling. Check yourself: do you go behind your manager’s back? Compete with them instead of collaborating?

A manager I coach started venting before he even sat down. After a kickoff, his manager said he trusted him completely and did not want to micromanage, and for a week now he has been dodging the meeting at which he is supposed to be updated on a problem. Even if your manager is toxic, you still need to manage effective communication with them. It will not make you friends, but it will make the relationship productive.

The tool: responses prepared in advance

• The goal is not to win but to influence, and to deliver a clear, neutral message.
• Identify patterns: when and how they approach you, a WhatsApp under pressure, a sudden call, bypassing.
• Adapt your wording to their style: what they hate hearing, and what makes them feel in control.
• Before every interaction define the goal of the conversation, and which three main topics you will raise. No more.
• Ask yourself before a hard meeting: what is my main goal, how is the other side likely to respond and what are my responses to each scenario, and in which state, composed, inclusive or calm, do I want to be in the meeting.

And there is a limit. When the manager repeatedly changes the targets and the promotion criteria after they have already been met, it may be gaslighting, a type of psychological abuse that undermines your sense of reality. There the steps are a feedback conversation about the act itself, clear boundaries in communication, and, if that does not work, turning to HR or to the manager’s manager.

How to communicate with senior managers

A manager at a large organization told me she had been preparing for a week for fifteen minutes with the CEO. You can learn this in five minutes, but first you need to understand the state of mind of senior managers. They are very busy, responsible for many domains, and their most precious resource is time. The result is low attention and strong filtering mechanisms. They ask themselves three questions: why should this matter to me, why now, and why is the person talking to me the right one. The responsibility for delivering the message is yours, not that of whoever receives it.

Two structures that work

• What, So What, Now What. What is the topic, why it matters to the audience, and what it requires of them. As Frank Luntz wrote, it is not what you say, it is what people hear.
• Information, context, remaining actions. A structure for a sharp answer to a senior person who asks a hard question. Know in advance what each senior person needs to hear.

And a senior manager has to be multilingual, not in languages but inside the organization. I was in a shouting meeting among sales, product and development, where everyone was sure the others did not understand. Every specialty has its own working methods, starting assumptions, jargon and goals. Clarify the terms, and check how the task connects to the organizational vision from the point of view of the department facing you.

Organizational politics and the stakeholder map

I don’t like the term organizational politics, because of the negative feeling it carries. It makes us attribute negative traits to colleagues and turn them into demons who make illogical decisions. The odds of eliminating organizational politics entirely are low. It is not playing the game, and it is not something to run from. It is understanding the people we work with and working with them more effectively. Conflicts are a natural byproduct of any organization with teams that have different goals and compete for resources.

The tool: the stakeholder map

A simple strategic tool that almost nobody uses, and the first task I give almost every manager I coach:

• Map your management goals and the milestones for reaching them.
• Prepare a full list of stakeholders: people, teams, departments, customers and suppliers. Who will be affected by the project? Who can influence its success or failure? Who holds power in decision-making?
• Analyze each one’s power, influence and interest.

And from there to Nemawashi, an informal Japanese process for building agreement before making decisions. A manager who had just entered a senior role told me about a crisis with a veteran employee that reached the CEO, who summoned both of them to a conversation in two days. I asked what would happen in the conversation. He answered: “I don’t know, I’ll find out in the conversation.” With an informal channel to the CEO, he could have gotten a picture in advance and even delivered his messages before the meeting.

AI and the vertical multi-layer manager

AI agents are erasing the classic management layers. A 2026 article by Van Quaquebeke, Gazdag and Lee calls an employee who manages a fleet of semi-autonomous agents a vertical multi-layer manager: a person who through the day switches hats between strategist, coordinator and supervisor. An entire hierarchy collapsed into one person, with a price of cognitive load, loss of meaning and damage to the sense of contribution. Two tools: Reflection Spaces, such as team meetings without screens, and reconnecting to the vision of impact, so that pride shifts from creating the output to designing the system.

And AI is not replacing employees. It is forcing organizations to speed up. On the way to change you must preserve the sense of value and belonging of those who remain, because groups do not move fast on shaky ground: full transparency about reality, legitimacy for uncertainty, and shared managerial vulnerability. Vulnerability meaning putting complexities, doubts and mistakes on the table, not crying or excessive emotional exposure.

The data. According to Challenger, Gray & Christmas, in 2024 a record 2,221 CEOs in the US announced departures, the highest since the figure began to be tracked in 2002. I see this as a turning point in the role: leadership is no longer measured only by knowledge, but by the ability to hold chaos and lead through it. A Harvard Business Review article I wrote about recommends developing three things: being a learner, meaning asking the right questions and building a culture of constant learning; investing in people in advance and building trust that holds in hard moments; and keeping proportion, knowing when to wait, when to act and when to double down.

Entrepreneurship: pivot, MVP and a support system

Two young founders I coach concluded that their demo does not work and they need to change direction. Their courage surprised me. After hours, budgets and emotional resources, it is much easier to convince ourselves the problem is external. A pivot is not failure. It is progress based on real learning from the market.

• The MVP starts from the problem and not from the product: who the customer is, what their biggest pain is, and why what exists today is not enough.
• The MVP tests the underlying assumptions, not the product: is the problem really painful, and will they be willing to pay for the solution.
• The minimal solution does not have to work. A landing page that measures interest or a manual prototype can be enough.

And even someone working alone needs a support system. It took me time to understand this as a solopreneur. Not to ease loneliness, but so that someone will challenge my decisions. The cobbler’s children go barefoot, since this is exactly the service I give CEOs. Even Steve Jobs took walks with Bill Campbell.

How this connects to the Identity-Aligned Leadership Cycle

In the Identity-Aligned Leadership Cycle I work with, this stage rests mainly on the alignment step: connecting clarity to organizational realities and needs. As you rise in rank, the challenge is to connect who you are with what the organization, the leadership and the market need.

Frequently asked questions

What is strategic thinking, and how do you develop it?

Strategic thinking is the ability to look at reality through a systemic, forward-looking perspective, identify patterns and trends and make decisions based on them. It is a learned skill. The first step: think at least one range above your role, in space and in time, and ask how what you do affects others and the organization’s goals.

How do you present a topic to a CEO in a short time?

Answer in advance the three questions they ask themselves: why should this matter to me, why now, and why you. Build a short, focused message in the structure of What, So What, Now What.

What do you do with a toxic manager?

First check your own part in the relationship. Then identify their patterns and prepare responses in advance, with the aim to influence and not to win. If it is gaslighting, set clear boundaries, and if that does not work, turn to HR or to the manager’s manager.

How does AI change the manager’s role?

It compresses management layers, so one person functions as strategist, coordinator and supervisor of a fleet of agents. The price is cognitive load and loss of meaning. So the manager needs to build reflection spaces, reconnect themselves and the team to the vision of impact, and keep a sense of value and belonging during the change.

Sources for the data

The tools and cases on this page are based on my LinkedIn posts, linked throughout the text. These are the sources for the data:

• Challenger, Gray & Christmas. New Records Set: CEO Exits Surge Post-Election in December 2024