Derisk Your Work

How to proactively identifying and mitigating risks

🔍 Identify Risks

  1. What's most likely to go wrong?

  2. What can I do to prevent this from happening?

⚙️ Address Risks

  • Embrace a Healthy Sense of Paranoia: Cultivate a mindset that anticipates potential issues. Regularly assess for risks and consider ways to improve outcomes. This proactive approach can become a subconscious habit, minimizing the effort required over time.

  • Risk Exists on a Spectrum: Not all risks are equally probable or severe. Prioritize risks by considering their likelihood and potential negative impact. Focus energy on the most significant risks.

  • Utilize First Principles: When unforeseen issues arise, go back to the fundamentals of the situation. Analyze the basic components to understand the root cause and identify potential solutions.

  • Set Explicit Expectations: Clearly communicate expectations when delegating tasks to team members. Specify the desired outcome, relevant details, and timelines. This helps reduce misunderstandings and miscommunication.

💡 Examples

aka: situational leadership

Delegate to a Team Member

  • Situation: Assigning customer case studies to a junior team member.

  • Risk: They might lack experience in strategic work and choose case studies without considering the target audience.

  • Action: Explain the strategic purpose of case studies (attracting ideal customers) and ask guiding questions to gauge their understanding and offer support. Check in with the team member after they complete a few entries to ensure alignment and identify any potential issues early on.

Build Something New

  • Situation: Planting astilbes with a vision of a wall full of flowers.

  • Risk: Astilbes might not thrive in the chosen location due to insufficient sunlight.

  • Action: Research the sunlight requirements of astilbes and choose a location that meets their needs.

Deliver Bad News

  • Situation: Informing a customer about a mistake.

  • Risk: The customer becomes upset and cancels their contract.

  • Action: Take responsibility for the mistake but frame the situation to minimize its impact. Be honest while avoiding language that exacerbates the situation.

Sharing a Controversial Idea

  • Situation: Presenting an unconventional idea that might face pushback.

  • Risk: The audience misunderstands the intention behind the idea.

  • Action: Clearly articulate the idea, use phrases like “to be clear” to prevent misinterpretations, and explicitly state what the idea does not imply.

Give Constructive Feedback

  • Situation: Providing critical feedback to a direct report.

  • Risk: The direct report feels demotivated or disregards the feedback, believing it to be unjustified.

  • Action: Approach the feedback from the direct report's perspective. Ensure that the feedback focuses on strategy rather than personal opinions and reassure them of your belief in their capabilities. Frame the feedback constructively and focus on actions they can take to improve.

Test an Offer

  • Situation: Launching a new product or service with uncertain customer response.

  • Risk: Investing resources in a product or service that might not resonate with the target audience.

  • Action: Instead of a large-scale launch, conduct a smaller test launch with a segment of the target audience. This allows for gathering feedback, making necessary adjustments, and minimizing potential losses.

Troubleshoot a Technical Issue

  • Situation: A technical issue arises.

  • Risk: Wasting time and effort on ineffective troubleshooting steps.

  • Action: Research common causes of the issue and try established solutions before seeking assistance. Document steps taken and findings to share with support teams.

Give Feedback to a Peer

  • Situation: Providing feedback to a colleague.

  • Risk: The feedback is perceived negatively and damages the working relationship.

  • Action: Deliver feedback constructively, focusing on specific behaviors and their impact. Frame the feedback positively and offer suggestions for improvement.

Present to Leadership

  • Situation: Presenting to the CEO and leadership team.

  • Risk: The presentation lacks clarity and fails to convey the intended message effectively.

  • Action: Prepare thoroughly, use clear and concise language, and anticipate potential questions. Focus on conveying the key takeaways and ensure a smooth flow of information.

Resolve a Bug Quickly

  • Situation: Reporting a bug that needs prompt resolution.

  • Risk: The bug report lacks clarity and fails to convey the issue's severity, delaying resolution.

  • Action: Provide a detailed description of the bug, including steps to reproduce it and its potential impact. Use clear and concise language and prioritize the bug's importance.

Give Project Updates

  • Situation: Providing a project update to the manager.

  • Risk: The update is unclear, meandering, or overloaded with unnecessary details, leaving the manager unsure of how to support the project.

  • Action: Structure the update with the main point at the top, followed by supporting context. Be explicit about any support needed from the manager and highlight potential risks to demonstrate strategic thinking.

Pitching and Cold Outreach

  • Situation: Pitching an idea or conducting cold outreach.

  • Risk: The pitch or outreach fails to capture attention and generate interest.

  • Action: Tailor the message to the specific audience, highlighting the value proposition and addressing their needs. Craft a compelling narrative and use strong calls to action.

Raise Prices

  • Situation: Increasing the price of a product or service.

  • Risk: Customers react negatively to the price increase, leading to churn.

  • Action: Communicate the price increase transparently, explaining the reasons behind it. Highlight the value customers receive and emphasize any improvements or added benefits.


In Short

To consistently derisk your work, cultivate a mindset that proactively identifies and addresses potential problems by considering what's most likely to go wrong and taking preventative measures to mitigate those risks.

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