Ep. 16 | The Art of Negotiation

Finance leaders spend their careers managing risk, scrutinising decisions and protecting the financial health of their organisations. But being too risk-averse can come at a cost.

From knowing when to hold your position to recognising when it is time to walk away, many of the skills required around the poker table have direct parallels with the decisions finance leaders make every day.

In Episode 16 of Finance Chief Uncut, host Ella Wilkinson meets Jo Living, Founder of Aces High, to explore what poker can teach finance professionals about negotiation, risk, assertiveness, emotional control and decision-making under pressure.

After a decade in investment banking followed by 10 years across startups, innovation and entrepreneurship, Jo founded Aces High to use poker as an immersive way of helping professionals understand how they behave in high-stakes situations.

Rather than focusing on gambling, Aces High strips that element away and uses the strategic principles of poker to explore how people communicate, negotiate, assess risk and respond when the pressure rises.

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In this episode Ella and Jo explore:

• Why finance leaders need to reframe their relationship with risk
• What poker can teach professionals about negotiation and decision-making
• Why knowing when to fold matters in business
• How assertiveness differs from aggression
• Why listening can give finance leaders an advantage in negotiations
• How finance can move from gatekeeper to commercial partner
• Why empathy, intuition and reading the room still matter
• How to maintain composure when conversations become tense

Reframe risk as opportunity

Finance professionals are often among the most risk-aware people in an organisation. While that discipline is essential, Jo argues that eliminating risk entirely can also mean eliminating opportunity.

Poker teaches players to think in terms of expected returns rather than certainty. The question is not whether one particular hand will definitely win, but whether making the same decision repeatedly would leave you better off over time.

The same principle can apply in business.

A new investment, commercial deal or career opportunity might not have a guaranteed outcome, but finance leaders can assess whether the potential return justifies the risk.

That means avoiding both extremes: going all in on every opportunity or folding every time the outcome is uncertain.

Know when to fold

Knowing when to walk away can be as important as knowing when to pursue an opportunity.

Jo explains that loss aversion can make this difficult. Once people have invested money, time, energy or reputation into something, emotion can encourage them to keep going even when the evidence suggests they should stop.

Poker provides a different perspective: protecting your chips and minimising losses matter just as much as maximising gains.

For finance leaders, this means separating ego and emotion from the decision and returning to the strategy established at the outset.

If the evidence has changed, leaders need the discipline to reassess their position rather than doubling down simply because they are already invested.

Understand your default response

Aces High uses poker to reveal how people naturally respond to risk, conflict and decision-making.

Some people instinctively become more aggressive under pressure. Others become cautious and withdraw. Neither response is automatically right or wrong.

The important skill, Jo says, is understanding your default behaviour and learning when to adjust it.

She describes this as becoming a “strategic chameleon”: someone who can recognise what a situation requires and dial different behaviours up or down accordingly.

For an assertive leader, that could mean stepping back and listening. For someone naturally cautious, it could mean speaking up, placing a bigger bet on their ideas or making their value clear.

Use the power of the pause

One of the simplest lessons finance leaders can take from poker is the value of slowing down.

When a negotiation becomes tense, people can move into a fight, flight or freeze response. At that point, the instinct to react quickly can override the considered judgement needed for good decision-making.

Jo recommends deliberately creating space before responding.

That could mean counting to 10, taking a long exhale or simply pausing before answering. In more difficult situations, it could mean stepping away and returning to the conversation later.

Owning the pace gives leaders time to regulate their response, assess the information available and make a decision rather than simply reacting.

Stop negotiating from your own position

One of the biggest mistakes finance leaders can make in a high-stakes negotiation, according to Jo, is focusing entirely on what they want.

Poker requires players to think beyond their own cards and consider what their opponent might be holding. Negotiation requires the same shift.

Finance leaders should understand their own boundaries and objectives, but they also need to consider what the other person needs from the conversation.

That requires empathy, listening and an ability to identify the different variables available for negotiation.

If price is one point of contention, for example, timing, scope, delivery or another element of the agreement could create room for both parties to reach a better outcome.

Sometimes speaking first can help anchor a numbers-based negotiation. In other situations, Jo argues that there can be greater value in speaking last, listening first and understanding the parameters before revealing your position.

Become a commercial partner

Finance can easily become viewed as the function that says no: controlling budgets, questioning spending and challenging proposals from elsewhere in the organisation.

Jo believes poker offers another way to think about the finance leader's role.

Different functions may appear to be competing, but they are often trying to achieve the same overall objective while working with different information and priorities.

Marketing wants investment. Sales wants to deliver for the client. Technology needs the resources to build. Finance needs to manage budgets and protect the business.

Rather than approaching these conversations as win-or-lose negotiations, finance leaders can treat them as an exchange of information.

Like a poker player reassessing a strong hand when new cards appear, leaders need to remain willing to change their position when new information comes to light.

Listening, questioning and continually reassessing the situation can help finance move beyond gatekeeping and become a stronger commercial partner to the rest of the organisation.

Read the room

Data, statistics and financial fundamentals remain essential, but Jo argues that high-stakes decision-making also requires human judgement.

Poker is not simply about the cards. Players observe patterns, behaviour, timing and changes in how other people respond.

The same skills can help in the boardroom.

Understanding how colleagues prefer to communicate, recognising changes in behaviour and considering the motivations behind someone else's position can provide valuable context.

Jo cautions against treating body language as a way to identify whether somebody is lying. Instead, behavioural changes can indicate stress, giving leaders another piece of information to consider alongside the facts.

For finance professionals operating in an increasingly AI-enabled environment, she believes judgement, intuition, empathy and discernment will become increasingly valuable alongside data-driven analysis.

Stay composed when the stakes rise

Jo's practical advice for difficult conversations starts with remembering that there is always an exit.

“You can always fold,” she explains. Not every conversation needs to be resolved immediately and not every position needs to be defended indefinitely.

When tension rises, finance leaders can pause, take one long breath out and reconnect with what is happening in the room before responding.

Preparation matters too.

Understanding your boundaries, knowing what you want from the conversation and considering what the other person needs can reduce the likelihood of being caught off guard.

There is no way to remove pressure from every high-stakes decision. The objective is to become more aware of how you respond to it.

By recognising those tendencies, finance leaders can move beyond automatic fight, flight or freeze responses and choose the behaviour the situation actually requires.

Explore more from Finance Chief Uncut

Catch up on Episode 15, featuring Adam Barbera, Co-Founder and CEO at Dost AI, discussing AI-native finance, digital coworkers, the foundations of finance transformation and how finance leaders can move towards increasingly autonomous operations.