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Addressing Common Leadership Issues – Pt5: Getting People to Think Critically and Strategically

Updated: Aug 23, 2022

This is the fifth in a series of blogs in which we will look at some of the common issues faced by modern leaders and how they can be addressed. Today, we will consider how to get people to think beyond the immediate and appreciate the bigger picture when making decisions.

It is a common occurrence: you are busy trying to manage multiple priorities with what seems like an ever-diminishing amount of time available when he/she walks into your office. You inwardly groan, knowing that you are about to be asked a question that he/she should really be able to deal with by this time. Sure enough, your intuition is right and out pops the question. You know that you need to spend some time helping this person work out how to deal with such matters without coming to you every time, but you are rushed and it is simply easier and quicker to give them the answer. So that is what you do, and the problem is resolved - at least until the next unwelcome intrusion! As the door closes you wonder what you can do to effect change.

If the above scenario is something you are familiar with, here are some development steps you can take to begin helping your team to build critical and strategic thinking competencies (as you go through, assess your own and others' current levels and use as benchmarks):*

Level 1: Execute

Here the individual just does what is asked. He/she may be new in role and needs time to acclimatise. Can the person complete assignments fully, on time and to the required standards within the governance boundaries set? If not, ensure your instructions were clear (ask them to explain their understanding of the requirements).

Does he/she show signs of verbal reasoning, effective decision-making and problem-solving? Ascertain these things by asking what they did, how, why, what they would do differently next time, etc.

Level 2: Synthesise

The person learns to sift information and identify what is really important (separates the 'wheat' from the 'chaff').

Does he/she separate the important from the unimportant insights, accurately assess the relative importance of key insights and communicate them clearly and concisely? This skill can be developed by acting as a secretary and taking the minutes for complex meetings, doing and presenting market research, etc. It is also helpful to work through case studies of complex scenarios.

Those able to synthesise quickly/on the spot are ready for the next level.

Level 3: Recommend

Having identified what is important, the person now learns how to make well-founded recommendations.

Does he/she consider alternatives, provide a clear recommendation to you when it is necessary to escalate (including options considered, assumptions, risks, knock-on effects, etc.) and back the recommendation with strong, logical reasoning?

One of the biggest barriers to developing this level of skill is the (often subconscious) tendency of the line manager to 'anchor' the person's thinking by showing a preference for a particular option before the recommendation is made.

Level 4: Generate

Here the individual moves beyond working with existing information and practices to creating innovative ideas which translate the organisation's vision into practical programmes and projects.

Does he/she convert the vision into objectives and plans, propose innovative solutions and ask and answer questions others may also have but cannot frame?

This mindset can be promoted by modelling these behaviours for them, encouraging open-ended thinking/brainstorming and evaluating their ideas with them.


I am sure you can already see the many benefits that would accrue from having people who have mastered these skills. They include:

  • Saves you time and stress, and makes your engagement with them more enjoyable and satisfying!

  • Boosts agility

  • Generates innovative ideas

  • Builds greater team cohesion and performance

  • Enhances their engagement with the attendant positive business outcomes which include lower staff turnover, greater resilience, fewer sick days, fewer accidents, higher profits, etc. (see the MacLeod report for more quantified benefits).

  • Etc.

Common Barriers

  • Not knowing how to develop the required skills (use this guide and get a coach/mentor to support)

  • Rushing through the levels without allowing sufficient time for embedding what is learnt.

  • Thinking that everybody can do this at level 4. Everyone is of equal worth but we are not all the same; we all have our strengths and weaknesses.

  • Being a boss but not a leader.

Being a micro-manager or having an attitude of 'I am always right and my way is always the best way' virtually guarantees failure. Incidentally, when you refuse to listen to those around you, you will soon find yourself surrounded by people with nothing to say!

  • Allied to the 'boss' point above, punishing mistakes. Good governance should prevent any mistakes from having consequences which are too severe. However, as with all skills, development takes time and practice and mistakes will be made. Unless they are caused by laziness or gross incompetence, use them as learning points.

  • Inability to coach. Just telling people to 'think more critically and strategically' is not likely to yield the results you are seeking. Coaching helps to surface more information, deepens thinking and gives the coachee greater ownership and responsibility for the solutions.

  • Lack of time - perhaps the most common barrier. The approach outlined above will take more time initially. However, it is a good investment, even if people improve by just one level.

Almost all business leaders are busy so spending precious time thinking about and coaching staff in this area may seem unappealing, but what is the option? The ever-increasing workloads for executives and managers show no sign of abating so there must come a point at which it is unsustainable to simply keep on doing the same things the same way.


The whole point of leadership is to engage with and build your team to help achieve your vision. Developing your people to think more critically and strategically is a powerful way of doing so that would greatly facilitate an organisation's ability to manage multiple, complex priorities. Note again the option of getting external coaching/mentoring/training support.

As noted above, this is the fifth blog in a series addressing leadership issues. If there is a topic you would like Aspire to cover in subsequent releases, or if you would like a no-obligation consultation to discuss the subject of this blog, please comment or email We will not spam you!

Aspire MCL - unleashing YOUR leadership potential

*If you want to read more deeply into these steps, here is the link to the excellent HBR article from which they are derived: (Matt Plummer)

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