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Decision-making

Dilemmas to Decisions

Acting Wisely When You Need to Think Fast

Andrew explores three common leadership dilemmas through lived experience and research, giving you practical strategies to make difficult decisions wisely, promptly and with less stress.

Why this talk

The Three Dilemmas

Dilemma 1: Never give up? Or wake up and smell the coffee?

Dilemma 2: Bold decisions? Or play it safe?

Dilemma 3: Tackle the core issue? Or tackle the peripheral issues?

When 85% of 14,000 organisational leaders say they're fatigued by the sheer number of decisions they now face and 1/3 of those surveyed said they rely on their gut for decision making, it's clear that learning how to make better decisions when the pressure is on, remains a crucial skill for leaders and managers in 2026.

Drawing on a wealth of lived experience and research, we'll explore three common, confusing dilemmas faced by organisational leaders, revealing insights and strategies through each dilemma, to help you make difficult decisions wisely, promptly and with less stress.

What this session covers

The agenda, point by point

Everything your audience will move through — so you can judge the fit before you book.

  1. 1

    Why your gut is both powerful and flawed as a decision making tool and when to best use it.

  2. 2

    Why unconscious biases undermine good decision-making and the most dangerous biases to look out for, from Sunk Cost Fallacy, Optimism Bias, Confirmation Bias to Tabloid Thinking.

  3. 3

    How to create an Investment Timeline, to prevent you from getting stuck when you don't know whether to persevere or quit.

  4. 4

    How to navigate your most difficult decisions with minimal stress, and why heuristics enable prompt decision making, whilst protecting you from the flaws in your gut.

  5. 5

    How to create your own heuristical decision making strategy, which can act as your guide when faced with big decisions.

  6. 6

    Why we ignore important issues when we're under pressure and how to spot problems early, using techniques such as Elephant Spotting and the Pre-Mortem in order to prevent nasty (yet avoidable) shocks.

What your people leave with

Concrete outcomes, not vague good feelings

Understand when to trust your gut — and when not to
Recognise the most dangerous unconscious biases affecting your decisions (Sunk Cost Fallacy, Optimism Bias, Confirmation Bias, Tabloid Thinking)
Build an Investment Timeline to know when to persevere or quit
Navigate difficult decisions with minimal stress using heuristics
Create your own heuristical decision-making strategy
Spot problems early with Elephant Spotting and the Pre-Mortem
Who it's for

Organisational leaders, managers and teams who face high volumes of complex decisions under pressure

Andrew delivering a session to a full room
How you can book it
Keynote
45–60 minutes
Interactive workshop
Half or full day
In-person or virtual
Delivery to suit your event
Tailored to your event
Duration flexible
Studio headshot of Andrew Pain
Andrew Pain speaking on the TEDx stage
Meet your speaker

Mental Health & Resilience Keynote Speaker

Andrew speaks from lived experience — warm, honest and human, with the experience to back it up.

  • TEDx speaker
  • Host of the Men on Show podcast (60 episodes)
  • Author of the forthcoming book Honestly, Man
  • Member, International Coaching Federation
“Excellent presentation on the subtle art of successful delegation. Really helpful tools and tips, conveyed in an easy to understand and down to earth way, with plenty of great real life examples.”

John McCrossan

Senior Analyst, Scottish Government

Bring this to your organisation

Ready to talk it through?

Tell us about your event and audience — we'll come back with availability and how Dilemmas to Decisions could land for your people.

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