How does a GC make the decisions no one else wants to?

Every GC eventually meets a moment where the “right” answer isn’t obvious – or popular. Alexander Shevchenko, Chief Legal Officer at WebPay, shares the mindset and decision-making framework he uses to navigate these defining leadership moments.

Every manager, at some point, faces a defining moment: a decision that is tough, controversial, or deeply unpopular. These choices test not just your leadership but your values, courage, and ability to balance competing priorities.

Such decisions often involve navigating conflicts of interest or making moral judgments – whether it is reducing staff to ensure financial stability, addressing a colleague’s misconduct, or restructuring a business unit to align with strategic goals. These moments often carry high stakes, impacting team morale, company performance, and your own reputation as a leader.

The standard process for making decisions (consisting of defining the objective, checking authority, clarifying the deadline, simplifying things, gathering information, listening to opinions and determining options, conducting a risks versus benefits analysis and listing pros/cons, checking reversibility, choosing an option, and implementing it) may seem to be insufficient for tough decisions.

As a Chief Legal Officer, to overcome the complexity and discomfort of hard decisions, I usually invoke the following principles:

1. Be on the side of the senior management team, the company directors and owners.
2. Put the interests of the company and the team above my own interests and the interests of specific individuals.
3. Assess how a decision aligns with my core values and the company’s culture to ensure ethical and consistent leadership.
4. Evaluate how well a decision aligns with the company’s strategic goals and objectives (act in the best interests of the business).
5. Recognise and overcome mental biases such as fear of failure, concern about what others will think, the need to make the right decision, and the sunk cost fallacy.
6. Ensure that there are sound, logical, and clear reasons behind the decision that are understandable to a rational person.
7. Separate personalities and emotions from the problem, creating psychological distance from it.
8. Use emotional intelligence (recognising, understanding, and managing my own and other people’s emotions).
9. Place facts ahead of gut feelings and past experience.
10. Use scenario planning (anticipate multiple outcomes by mapping best-case, worst-case, and likely scenarios for each decision option).

What techniques do you rely on to navigate tough decisions?

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