Why a Strategic Session?

Why business owners get stuck in operations and how a strategic session breaks the cycle

Almost every business owner eventually notices a strange pattern: the company seems to be running, processes are in place, but the moment they step back even slightly, everything starts to slow down and fall apart. You’re constantly “putting out fires,” making most decisions yourself, and watching the team freeze while waiting for the next instruction. And, of course, all responsibility inevitably ends up on your shoulders. Sound familiar? ?

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The most interesting part is that this usually has nothing to do with low employee competence or a lack of leadership on your part. It’s a direct consequence of not having a clear point in business processes where authority and responsibility are formally transferred to the next management level. A professionally organized strategic session plays exactly this role — a fundamental switch in how the business is run.

What a strategic session is

Let’s clarify the concept right away. A strategic session has nothing in common with a typical meeting, a formal gathering “for the record,” or a team-building event.

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It is a clearly structured group work involving the owner, key managers, and, when necessary, external experts. The purpose of such a session is to:

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• define real, achievable goals;

• fix concrete steps to reach them;

• assign responsibilities and accountability across the team.

So what’s the difference from the usual boring meetings? ?

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The key difference is that there are no abstract promises or vague phrases like “we’ll see,” “let’s think about it,” or “we’ll try.” Those rarely lead to real results.

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☝️ During a strategic session, each manager publicly states what result they are responsible for, which resources they will use, and by which metrics their performance will be evaluated. At this point, management stops being manual. For the business owner, a strategic session makes it possible to influence the company through a system — not through constant involvement in small operational details.

Why a business actually needs a strategic session

In daily routine, responsibility has a way of quietly sliding back to the owner. Someone didn’t push a task through, didn’t make a decision on time — and you step in again just to keep things moving. And once again, you’re responsible for everything. Yes, we’ve all been there ?

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A strategic session helps stop this cycle and establish new rules of the game. Within the joint work, the owner openly states that they are no longer carrying everything alone and expect a different level of responsibility from managers. It may be hard to believe, but even this alone can change team behavior: responsibility stops being blurred — not instantly and not without mistakes, but it does.

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In addition, a strategic session with the team helps everyone start thinking as a single whole. Very often, marketing, sales, and production operate as if they were in different dimensions, consuming resources without visible growth in overall profit. During the session, full synchronization happens. Everyone sees the common development vector and understands how their actions affect the company’s final result.

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Another important effect is uncovering hidden obstacles in business processes. In day-to-day work, chronic problems are often ignored: interdepartmental conflicts, weak management decisions, inefficient processes. A strategic session brings these issues from the background to the surface and shifts the focus from empty complaints to real solutions.

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It also helps legitimize difficult decisions, such as entering new markets or restructuring. When decisions are imposed top-down, people resist. But when ideas are born through discussion, the team perceives them as their own work — not as a whim of the owner.

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We shouldn’t forget the psychological aspect either. For managers, participation in such a process sends a strong signal: “I am trusted, I am relied upon, I matter for the future of the business.”

Palantir technologies Inc.: From –$374M to +$1.02B in 3 years

The problems described above are extremely common among small and medium-sized businesses. A good example is the American company Palantir Technologies Inc., which develops software for big data, analytics, and artificial intelligence. Over recent years, the company’s revenues have grown by more than 200%.

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However, in 2022 the situation was dire. Palantir was drowning in operational costs. The company reported a net loss of around $374 million, and its stock kept hitting new lows. The business was generating revenue, everyone was busy, every department was working — but expenses far exceeded profits.

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By 2025, Palantir’s net income reached $1.02 billion. What became the turning point? In the 2022 financial report, CEO Alex Karp pointed out that one of the ways out of the crisis was strengthening strategic planning and adopting a more systematic approach to management.

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The financial results over three years are impressive, aren’t they?

Something important to note

A strategic session is not about inventing a strategy from scratch — that’s a myth.

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In most cases, the owner already has an understanding of goals and direction. The real question is different: is the team capable of implementing these ambitions? That’s why a strategic session is essentially about the team defending their plans in front of the owner:

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• which projects will be launched and for what purpose;

• what resources they require;

• who will carry personal responsibility for the result.

How a high-quality strategic session works

As an entrepreneur, I enjoy studying analytical materials. Recently, I came across an interesting McKinsey & Company study. Among nearly 800 surveyed executives, only 45% were satisfied with the outcomes of their strategic planning processes. At the same time, 79% stated that strategic planning is still necessary for sustainable business growth. Strategic sessions directly influence this process — but how do you make them truly effective?

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Stage 1. Preparation

Half of a strategic session’s success is determined before the meeting even starts. Preparation takes several weeks. At this stage, deep analytics are collected, and each manager prepares “homework” outlining problems and resource requests. Without this stage, any strategy risks remaining a nice conversation with no real consequences.

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Stage 2. The Session Itself

The main part usually lasts from one to three days. First, the team analyzes past results, honestly reviewing achievements and mistakes, while managers present their view of the situation. Then the focus shifts to future projects, goal decomposition, and discussion of concrete plans with financial benchmarks.

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? From experience, I can say that the key success factor here is having an external moderator. Why this matters — and why it’s risky to run such sessions on your own — is worth a separate discussion.

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Stage 3. Results and Fixation of Decisions

The outcome of a quality strategic session is not emotions like “wow, that was productive,” but fixed management decisions. The company leaves with a clear set of agreed projects, a transparent distribution of goals across departments, and personal accountability of managers for implementation. This creates the foundation for management without constant owner intervention and for effective delegation.

Why you shouldn’t run a strategic session on your own

First, it’s important to understand that during such sessions, the owner should be a listener and observer. Can you truly just listen — without intervening or suppressing the team with your authority? Everyone has to answer that honestly for themselves.

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In my view, when an owner tries to moderate the process while remaining a participant, they almost always fall back into their habitual leadership role. You’ll start making decisions yourself again, managing instead of listening to alternative views — and responsibility will once more land entirely on you.

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An external specialist can ask sharp, uncomfortable questions the team may be afraid to voice to the CEO. The moderator maintains structure and strict timing, preventing the session from turning into chaotic discussion.

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So, an external facilitator isn’t about “doing it because everyone does.” It’s about achieving maximum results from the time invested and finally building a truly systematic management model.

The session Is done, what’s next?

The biggest mistake that can nullify all results is the absence of follow-up tracking. If no one monitors execution and new projects quickly get swallowed by operational routine, any strategy will remain on paper.

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Next time, the team will perceive such initiatives as a waste of time. That’s why it’s critical after the session to:

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• appoint a person responsible for monitoring task execution;

• introduce regular check-ins on the implementation of every strategic item.

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Even this alone can significantly increase the effectiveness of a strategic session ?

Who does not need a strategic session

I always tell entrepreneurs I work with: “If you want the best result from our collaboration, be honest.” I follow the same principle myself.

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So, honestly speaking, a strategic session is not for everyone ?

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It will not magically solve your problems — first of all, it requires working with mindset.

How to know If you need a strategic session now

To understand whether a strategic session is needed, answer three questions:

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• Do you know exactly who is responsible when problems arise in any department?

• Can your business operate stably for at least a month without your involvement?

• Does every employee clearly understand the company’s mission and development vector?

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If the answer to even one of these is “no,” a strategic session is at least worth discussing.

Preliminary strategic session consultation

I support a rational approach, so I don’t offer this format to everyone. When an owner is clearly stuck in operations, an external professional can see it immediately.

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During our first conversation, we’ll analyze your current business context in detail and determine whether a strategic session makes sense right now. It’s possible that another tool will be more effective for your business — and I’ll say that honestly.

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? Book a preliminary consultation to make a balanced management decision and finally build a business that works for you — not the other way around. Leave your contact details in the form below.