5 Ways CEO's and Directors Can Foster Courageous Decision- Making
5 min read

5 Ways CEOs and Directors Can Foster Courageous Decision-Making
The Courage to Decide Before You Have All the Information
Part of the New Leadership Accountability Series:
3 capabilities every leader needs to succeed in a complex world.
In our previous article, The Courage to Decide Before You Have All the Information, we explored why leaders can no longer wait for certainty before making decisions. We looked at the shift from relying on complete information to relying on sound judgement, asking better questions, challenging assumptions, considering different perspectives, and having the courage to make thoughtful decisions while remaining open to learning and adapting.
The challenge now is more practical:
If you want your leaders to make decisions, what can you do to create the conditions for them to do so?
At RainTree Business Coaching, we often hear CEOs asking:
"Why am I still being pulled into every important decision?"
"Why do my leaders keep bringing problems to me instead of recommendations?"
"Why do they seem so afraid of getting it wrong?"
Sometimes, the issue is not that leaders lack courage.
Sometimes, the organisation has unintentionally taught them to be cautious.
If every decision is questioned, every mistake is punished, or every difficult call is eventually overridden, leaders quickly learn that escalation is safer than ownership.
So, what can CEOs and Directors do differently?
1. Make decision rights clear.
Be explicit about which decisions leaders own, which require consultation, and which genuinely need escalation.
If people are unclear about where their authority begins and ends, hesitation is inevitable.
Ask:
"Which decisions should my leaders be making without me?"
Then make that expectation clear.
2. When a decision comes to you, ask your leaders questions instead of providing ‘the answer’.
It is easy for a CEO to become the default answerer.
A leader brings a problem. The CEO has the experience, sees the solution and provides the answer.
The problem is that this can unintentionally reinforce dependency.
Before giving the answer, use The Four Collaborative Questions (a coaching tool that RainTree Coaches use in many of their coaching journeys):
- What?
- How?
- Who?
- What if?
These allow you to ask open-ended, non-judgemental questions that support your leaders stepping into their power and making decisions with your guidance. Here are some examples you could ask:
"What do you recommend?"
Then explore their thinking.
How would you suggest we proceed?
Then unpack their suggestions.
Who could provide additional necessary insight to make this decision?
Then consider their recommendations.
“What if” is how you provide your input to their thinking, suggestions and recommendations without making the decision for them.
You may still need to make the final call, but you are developing judgement rather than creating reliance.
3. Review the thinking, not only the outcome.
A good decision can still produce a poor outcome.
A poor decision can sometimes produce a good outcome.
If leaders are judged only by whether things worked out, they will naturally become more risk averse.
Instead, use The Four Collaborative Questions Tool to support them to deepen their thinking. You could ask:
"What information did you have at the time?"
"What assumptions were you making?"
"Who did you consult?"
"What alternatives did you consider?"
"How could you have changed direction?"
If none of these types of questions give you the answer you are looking for, ask:
“What if…”
This shifts the conversation from "Was the decision right?" to "Was the thinking sound?"
4. Create room for well-reasoned mistakes.
No leader will make every decision perfectly.
If every mistake is treated as a failure, people quickly learn that the safest decision is no decision.
That does not mean removing accountability.
It means distinguishing between careless decisions and courageous, well-considered decisions that did not produce the expected outcome.
Ask:
"What did we learn?"
"How could we act differently next time?"
“Who could we have consulted with that would have improved the outcome?”
"What information did we need that would have changed the outcome?"
Learning from a decision is part of making the next one better.
5. Recognise and reward appropriate decisiveness.
If you want leaders to take ownership, make it visible when they do.
Recognise leaders who make thoughtful calls with imperfect information, involve the right people, communicate clearly and take responsibility for the outcome.
Even when circumstances later require the decision to change.
The message becomes clear:
We value courageous decisions grounded in good judgement, not perfect prediction.
And finally, look in the mirror.
Before asking, "Why aren't my leaders taking more ownership?", ask:
"Have I created an environment where they feel safe to do so?"
“Have I made it clear what they can decide?”
“Have I taken the time to guide them to make decisions when they have asked me to decide or do I step in too quickly?”
“Do I sometimes override decisions without explaining why?”
“When my leader makes a well-considered decision that turns out to be wrong, do I reward good judgement, or only good outcomes?”
Leadership accountability is not only about what we expect from our leaders.
It is also about the conditions we create for them to lead.
Courage does not grow in an environment of control.
It grows when leaders feel safe enough to be courageous and make decisions because they have clarity, accountability, trust and room to exercise judgement.
This is how CEOs and Directors can begin to shift decision-making from "I need you to tell me what to do" to "Here is what I recommend, and here is why."
That is the kind of leadership that builds stronger organisations.
Next in the series: We'll explore the second capability, Trust, and why creating an environment where people feel safe to speak up, challenge assumptions and share concerns is critical to better leadership and better decisions.
If you’d like to explore how coaching and mentoring can support your leaders, please connect with us.
Let’s start the conversation.
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