How to Develop Strategic Thinking in Managers

By Steven Haines

Develop strategic thinking in managers by helping them ask better questions, recognize patterns, move between detail and context, learn from experience, and consider consequences across time. Then give them opportunities to practice those habits on decisions that matter to the business.

“Be more strategic” is not a sufficient development objective.

A manager needs to understand what that expectation means in the context of the job. Does the organization want stronger recommendations, a broader view of customers and competitors, better anticipation of change, or more thoughtful investment choices?

Start by making the expectation observable.

Make strategic thinking part of management work

Strategic thinking should not be reserved for an annual planning meeting.

A manager can use it when evaluating a customer request, reconsidering a process, allocating resources, or interpreting a change in business performance.

The work involves connecting information to choices and consequences.

In Strategic Thinking in Action, I describe a progression from collecting information and making observations, through analysis and consideration of options, to decisions, action, and evaluation of results. Feedback connects the results to the next round of thinking.

That progression provides a useful development principle: do not teach strategic thinking only as a set of ideas. Help managers practice the movement from information to insight to action.

1. Practice asking better questions

The first habit is to examine the situation before accepting its initial framing.

Suppose a team reports that it needs more people because demand has increased. Additional staffing may be appropriate, but several questions deserve attention:

• Which demand has increased?
• Is the increase temporary or sustained?
• Where is work accumulating?
• What assumptions underpin the staffing request?
• What alternatives should we examine?

The purpose is not to delay a decision indefinitely. It is to make sure the team is addressing the right problem.

A practical exercise is to ask managers to prepare three probing questions before an important meeting. Afterward, they review which questions changed their understanding.

2. Look for patterns and connections

An isolated event does not necessarily indicate a strategic issue. Repeated observations may deserve closer examination.

Imagine that customer complaints, sales objections, and service costs are all rising around the same offering.

A manager might treat each as a separate departmental concern. Another approach is to investigate whether they share a cause.

Have customer needs changed? Is the offering becoming harder to support? Are sales commitments inconsistent with delivery capabilities?

Managers can practice by reviewing a small set of observations each week and asking:

What appears connected, and what evidence would help us test that connection?

The discipline is to distinguish a plausible interpretation from a conclusion supported by information.

3. Zoom in and zoom out

Managers need to examine details without losing the broader business context.

Zooming in might involve understanding a process failure, a cost assumption, or a customer’s workflow. Zooming out means examining how that issue connects to other functions, customer groups, strategic priorities, and market conditions.

Consider an illustrative decision to accelerate delivery for a particular customer.

The immediate question is whether the order can be expedited. The broader questions include which other commitments would be affected, what additional cost would be incurred, and whether the exception should influence future service policies.

Neither perspective is sufficient on its own.

A useful practice is to ask managers to explain a recommendation twice: first at the operational level, then in terms of its broader business implications.

4. Treat experience as material for learning

Managers make decisions under imperfect conditions. Development should include examining what happened afterward.

Following a significant decision, ask:

• What did we expect?
• What happened?
• Which assumptions held?
• What did we overlook?
• What should we carry into the next decision?

Keep the conversation focused on learning and judgment. A favorable result does not prove that every part of the reasoning was sound. An unfavorable result does not establish that the decision was careless.

The important task is to examine the information available at the time and what the experience now teaches.

5. Consider more than one time horizon

An immediate benefit can create a longer-term constraint. An investment with little near-term return may create options the business will need later.

Ask managers to consider the short-, medium-, and long-term implications of a recommendation.

For example, reducing a development budget might meet a near-term expense target. The analysis should also examine which capabilities would be delayed, whether that delay is acceptable, and what alternatives exist.

The point is not to favor the long term in every decision. It is to make the consequences across time visible.

These five habits form a central part of the development approach in Strategic Thinking in Action.

Build a manageable practice sequence

Rather than introduce every habit at once, organize practice over several weeks:

• Better questions: prepare questions before meetings and review what they revealed.
• Pattern recognition: examine recurring observations and test possible connections.
• Zooming: analyze a decision at both the detailed and broader business levels.
• Learning: review a completed decision and identify lessons.
• Time horizons: examine how a choice affects the business now and later.

This sequence draws on the practice approach in Strategic Thinking in Action. It is a way to organize development, not a promise that strategic thinking can be mastered in five weeks.

Managers should bring work examples to discussions and receive feedback on their reasoning.

Make the organization’s role explicit

Executives who ask managers to think strategically should provide strategic context.

That includes explaining priorities, discussing tradeoffs, and making room for questions. Managers also need to understand which decisions they can make and which require broader involvement.

For organizations planning leadership development for 2027, the useful question is not simply, “Which strategic thinking course should we buy?”

It is, “How will we help managers practice strategic thinking in the decisions they already face?”

Discuss strategic thinking development

The Business Acumen Institute provides strategic thinking training and capability assessments. Contact us to discuss the decisions your managers face and how a development program could support more thoughtful analysis, choices, and action.

Adapted from Strategic Thinking in Action by Steven Haines.