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Leadership Workshops on Critical and Strategic Thinking

October 24, 2026•4 min read•
Newsletter
Leadership Workshops on Critical and Strategic Thinking

3 new leadership workshops for leaders who decide too fast

Critical thinking, seeing the system, and leading through uncertainty. Three practical sessions where leaders work on their own real situations.

Most of the Leadership Toolkit is about what leaders do. You run the one-to-one, give the feedback, chair the meeting and set the direction.

These three new workshops are about the thinking that comes before those actions. Most of it happens fast and never gets tested.

Weak ideas get agreed because they sound confident. Good people get written off on a hunch. Problems come back however many times they're fixed, and plans get built around the one future everyone expects.

In all three workshops, leaders work on their own live material. Before the session, each leader brings a conclusion they hold right now, a problem that keeps coming back, or an area of their work where the next few years are unclear.

This week's three new leadership workshops

  • Critical Thinking for Leaders for testing a conclusion or a proposal before you act on it
  • Seeing the System and Making Change for problems that keep coming back
  • Leading Through Uncertainty for leading when nobody can say what's coming next

Each is a ready-to-run, two-hour session for 6 to 12 leaders, with a full facilitator guide, a one-page Quick Reference and a printable resource. It runs in person, with adaptations for virtual delivery, different group sizes and one-to-one coaching.

Critical Thinking for Leaders

Critical Thinking For Leaders

Think of someone at work you've formed a firm view of. Then think about what you saw them do.

The facilitator demonstrates with an example like this. Sam has arrived after nine on the last three Mondays. The leader takes it to mean Sam doesn't value the meeting, concludes Sam is disengaged, and gives the new project to someone else. All the leader saw was three late arrivals. Everything else, the leader added.

Critical Thinking for Leaders works on three moves. Leaders walk one of their own conclusions back down the Ladder of Inference to what they saw. They test a real proposal with Socratic questioning, stating it in its strongest form before they ask a single question. Then they turn a recommendation into a list of what would have to be true for it to work, and circle the one condition most likely to sink it. The last round is practice at questioning someone more senior without damaging the relationship.

You come out with a tested conclusion, a tested proposal, and three habits to use in your next meeting, all on the Critical Thinking Canvas.

Seeing the System and Making Change

Seeing The System And Making Change

Most leaders are trained to fix what's in front of them. The monthly report is late, someone chases it, and next month it's late again.

In the session's example, the data arrives on day three, the report is due on day five, nobody owns the handover, and everyone treats reporting as admin that gets done last. Chasing the report changes none of that.

Seeing the System and Making Change takes leaders below the surface of a real problem of their own. With the iceberg model they work down from the event to the pattern, the structures and the beliefs that keep it in place. They draw a simple loop map with themselves on it, and many find their own last fix feeding the problem. A simplified version of Donella Meadows' leverage points helps them judge which changes would make a real difference and which are within reach. Then they design a small, safe-to-fail experiment and test it against two colleagues, one playing the system and one playing the people it affects.

You come out with a map of the system around your problem and an experiment to start in the next two weeks, worked through in the Seeing the System Workbook.

Leading Through Uncertainty

Leading Through Uncertainty

Your team wants to know what next year looks like, and you don't know. Most leaders respond in one of three ways. They act as if they know more than they do, they wait for things to become clear, or they plan for the one future they expect.

Leading Through Uncertainty starts with Three Horizons, from Bill Sharpe and the International Futures Forum, to separate what's fading in a leader's area from what's emerging. With Critical Uncertainties, a Liberating Structure, each leader builds four possible futures and finds a no-regret move that makes sense in all four, plus early signs to watch for. Wicked Questions, another Liberating Structure, helps them hold two opposing needs at once, such as giving the team a clear plan and keeping options open.

The session ends with practice at saying "I don't know" well, using five parts: what we know, what we don't know yet, when we'll know more, what we're doing in the meantime, and what isn't changing. A colleague plays an anxious or sceptical team member, and an observer flags any slip into false reassurance.

You come out with several possible futures for your own area, one move to make now, and the words for your next conversation about the unknown, all in the Futures Template.

Where to start

About to sign off a proposal? Start with Critical Thinking for Leaders.

With a group of leaders, run Seeing the System and Making Change before Leading Through Uncertainty, so leaders have mapped the system they're looking ahead for.

What it costs

WorkshopBank Pro is $192 a year (at the time of publishing this article).

That's the full library I've built over 15 years, trusted by more than 200,000 facilitators and leaders.

You get all 364 workshops the day you join, these three included, plus unlimited modifications with our AI.

That's 53 cents a workshop. Set that against what it costs you to design one from scratch, or to buy a single session anywhere else.

Why join today

The price goes up as the library grows, and it never comes down. A week ago there were 361 workshops. Today there are 364, with more joining the Leadership Toolkit over the coming weeks.

Join now and you keep today's price, with every workshop we add after included.

→ Join WorkshopBank Pro

More next week,

P.S. If your team keeps fixing the same problem, start with Seeing the System and Making Change. Most leaders find their own last fix somewhere on the map.

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