Who Is Your Devil’s Advocate?
The person willing to challenge your thinking may be one of the most valuable people around your business — especially when the stakes are high.
Who is willing to challenge your thinking before reality does?
Most experienced business owners and advisers like to think they are objective. None of us is as objective as we imagine.
Experience helps. Expertise helps. Good intentions help. But capable people can still drift toward familiar assumptions, preferred strategies and interpretations that confirm what they already believe.
That is why intelligent challenge matters.
Who can question your reasoning before the customer, market, regulator, competitor or reality itself does it for you?
Confidence is valuable. Unchallenged certainty can be dangerous.
Clients, employees and stakeholders expect leaders to provide direction. That is entirely reasonable.
But confidence can slowly harden into overconfidence. The busier or more experienced we become, the easier it can be to move quickly from “I think this is right” to “I know this is right.”
That is where blind spots, weak assumptions and confirmation bias can creep in.
What does a good devil’s advocate actually do?
They are not there to argue for entertainment, create negativity or undermine authority. Their job is to pressure-test important thinking before the decision becomes difficult to reverse.
Ask the awkward question
What if the opposite is true? What information could we be missing? What would make this decision fail?
Challenge certainty
Separate what you know from what you assume, suspect, prefer or still need to verify.
Broaden the lens
Surface commercial, operational, financial, behavioural, reputational or customer consequences that may have been overlooked.
Strengthen the outcome
The best challenge often does not destroy the original strategy. It improves it.
Good judgement can still be distorted by very human pressures.
Familiarity
The longer we deal with a customer, employee, supplier or situation, the easier it can become to stop questioning what we think we already know.
Expertise lock-in
Deep expertise can make us more capable, but it can also make us overly attached to our own framework.
Commercial pressure
Deadlines, revenue pressure and the desire to maintain momentum can reduce the depth of review.
Confirmation bias
Once we prefer an answer, we may unconsciously give more weight to evidence supporting it.
Highly capable people rarely make poor decisions because they are foolish. More often, they are busy, familiar with the problem and too close to it.
Not every contrarian is a useful devil’s advocate.
The right person should be credible, commercially grounded and willing to disagree without turning disagreement into theatre.
- Independent thinking.
- Commercial realism.
- Professional maturity.
- Courage to disagree respectfully.
- An ability to identify the real risk rather than every imaginable risk.
- Enough context to understand the consequences of the decision.
It might be a senior colleague, external adviser, mentor, accountant, lawyer, experienced business peer or specialist.
Do not rely on somebody having the courage to challenge you by accident.
One of the stronger disciplines a business can develop is a deliberate review process for decisions that carry meaningful financial, strategic, legal, customer or reputational consequences.
Define the decision
Be clear about what is actually being decided, rather than debating several issues simultaneously.
State the assumptions
Write down what must be true for the decision to work.
Invite dissent
Ask somebody credible to make the strongest reasonable case against the preferred option.
Consider consequences
Examine the downside if the assumptions turn out to be wrong.
Look for missing voices
Ask whose customer, financial, operational or specialist perspective is absent.
Record the reasoning
Capture why the final decision was made and what risks were consciously accepted.
The higher the trust placed in you, the more valuable independent challenge becomes.
Financial advisers, accountants, lawyers, consultants and other professionals regularly make recommendations that carry consequences for other people.
A technically valid answer is not always the same as the best practical answer. Context, behaviour, implementation, risk and unintended consequences matter.
A credible second perspective can help ensure recommendations are not only technically sound, but also understandable, practical and defensible.
If this recommendation were reviewed twelve months from now by a sceptical outsider, what would they question first?
The owner can become the hardest person in the business to challenge.
Success can quietly create an echo chamber.
Employees may become cautious about disagreement. Suppliers want to retain the relationship. Customers see only part of the business. Even friends and professional advisers may avoid challenging an owner who appears absolutely committed to a particular direction.
That makes outside perspective especially valuable when decisions involve:
- Major capital expenditure.
- Expansion into a new market.
- Hiring senior people.
- Changing pricing or customer strategy.
- Borrowing or restructuring debt.
- Acquisitions or business sales.
- Succession or retirement decisions.
- Responding to a persistent performance problem.
Ask yourself these questions before the next major decision.
- Who can challenge my thinking honestly without politics getting in the way?
- When did someone last change my mind for the better?
- Do we pressure-test major decisions or simply discuss them?
- Which assumption am I most emotionally attached to?
- Where am I most likely to be overconfident?
- Do I reward agreement more than intellectual honesty?
- Whose perspective is missing from this decision?
- What would have to be true for my preferred option to be wrong?
The objective is not to become less decisive. It is to make better-informed decisions with fewer avoidable blind spots.
Better decisions, stronger businesses
Being challenged does not weaken your authority.
The right challenge can strengthen it.
The strongest leaders and advisers are not those who are never questioned. They are those confident enough to expose important thinking to intelligent scrutiny before the stakes become higher.
A good devil’s advocate can help you think more clearly, identify risks earlier and make decisions that stand up better over time.
So ask yourself again: who is your devil’s advocate?
Phil Manhire — Unicorn Consultants
Phil Manhire has more than four decades of business and advisory experience. Unicorn Consultants works with business owners on strategy, growth, systems, resilience, succession and practical business improvement.
Sometimes the most valuable conversation is the one that challenges your first conclusion.
A complimentary 30-minute Business Review gives you an opportunity to pressure-test an issue, decision or constraint with an experienced outside perspective.
♞ Arrange Your Complimentary Business ReviewDevil’s advocates and better business decisions
What is a devil’s advocate in business?
A devil’s advocate is a trusted person who deliberately challenges assumptions, reasoning and preferred options so that important decisions can be tested before they are implemented.
Why is constructive challenge important in business?
Constructive challenge can expose blind spots, confirmation bias, weak assumptions and unintended consequences before they become expensive problems.
Who can act as a devil’s advocate?
Depending on the decision, the role could be performed by a senior colleague, experienced adviser, accountant, lawyer, mentor, specialist or trusted business peer.
Does challenging a decision slow a business down?
It can add a small amount of time before an important decision, but thoughtful challenge can reduce the much greater cost of reversing a poor decision later.
How can business owners reduce confirmation bias?
Write down important assumptions, actively seek contrary evidence, invite independent perspectives and ask what would have to be true for the preferred option to be wrong.