1. Why now?
2. Is this a reversible or an irreversible decision?
3. If irreversible, what makes it so? Can I break it down into multiple smaller decisions, some of which may be reversible?
4. What factors won’t change in 10 years? How much of our plan is optimizing for durable traits versus betting on new trends and traits that will change?
5. How do we know we are succeeding in our goal?
6. What are

… [ Read more ]

Author: Kintan Brahmbhatt
Source: “35 Impactful Questions Managers Should Ask Themselves Regularly”
Original Publication: First Round Review
Subject: Decision Making Questions

Questions For Gauging Team Morale

1. Who haven’t I heard from?
2. How well do I know my team members? How well do they know each other?
3. Have I made a difference to each member of my team this week? (related: Have I checked in with each employee this week to see how they’re doing?)
4. Have I expressed gratitude to every single person on my team recently?
5. Is anyone a flight risk?

… [ Read more ]

Source: “35 Impactful Questions Managers Should Ask Themselves Regularly”
Original Publication: First Round Review
Subject: Management Questions

Before asking questions as a manager, it’s critical to know what motivates employees to stay with an organization and why. Gallup research shows 12 needs managers can meet to improve employee engagement, including:

• Prioritizing employee development
• Facilitating a sense of purpose
• Caring about employees
• Considering employee opinions
• Focusing on employee strengths

These five measures map closely with research recently published by HBR on [ Read more ]

Author: Susan Peppercorn
Source: “5 Questions Every Manager Needs to Ask Their Direct Reports”
Original Publication: Harvard Business Review (HBR)
Subject: Human Resources Questions

• What do her strongest allies say about her?
• What are her strongest strengths?
• What do her harshest critics say about her?
• What are her development opportunities? Her weaknesses, blind spots, and obstacles?
• When she is trying to influence you, how does she do it?
• How do you describe her leadership style?
• What environments bring out the worst in her?
• Do you think she’s more external facing or more internal facing? Do you

… [ Read more ]

Author: Alisa Cohn
Source: “The 30 Best Pieces of Advice for Entrepreneurs in 2021”
Original Publication: First Round Review
Subjects: Human Resources Questions, Management Questions

The following questions, based on BCG research into the characteristics of robust, resilient business models, can help you navigate this part of the process:

• Can the business model scale effectively? Can it be replicated across all your business units or the markets you serve, without diminishing returns?
• Will the business model differentiate your brand or product and make it more competitive in the marketplace?
• Will it reduce

… [ Read more ]

Authors: David Young, Marine Gerard
Source: “Four Steps to Sustainable Business Model Innovation”
Original Publication: Boston Consulting Group (BCG)
Subject: Strategy Questions

1. If you designed the agenda, what would be on it?
2. What is the executive not telling you that you feel you need to know?
3. How is the external world changing in ways that are not reflected in your board conversations?
4. What don’t you know about the company that you’re most concerned about?
5. What do you see always being discussed but never resolved?
6. What are you not discussing that you need

… [ Read more ]

Authors: Andrew White, Eric Wilkinson, Tazim Essani
Subject: Corporate Governance Questions

Far too many boards and CEOs see cybersecurity as a set of technical initiatives and edicts that are the domain of the CIO, chief security officer and other technical practitioners. In doing so, they overlook the perils of corporate complexity—and the power of simplicity—when it comes to cyber risk. We’d propose, in fact, that leaders who are serious about cybersecurity need to translate simplicity and … [ Read more ]

Authors: Richard Horne, Sean Joyce
Source: “Simplifying cybersecurity”
Original Publication: PwC
Subjects: IT Questions, Risk Management Questions

If you’re a chief exec or even an executive leader:

• Do you have a comprehensive understanding of the groups that most affect the organization’s ability to reach its goals?
• Do you know who your top customers and most critical employees are?

Now that you’ve identified them, ask yourself:

• Why do those customers and employees choose your company?
• Why do they stay?
• What is the likelihood of their future loyalty?

Authors: Chris Jones, Jake Herway
Source: “The Biggest Mistakes New CEOs Make and How Not to Make Them”
Original Publication: Gallup
Subjects: Corporate Governance Questions, Management Questions

Ask yourself these questions about your organization:

1. Do your values have relevance for your customers?
2. Do your customers experience your values in some way?
3. Do your values differentiate you within your industry?

Authors: Nate Dvorak, Ryan Pendell
Source: “Culture Wins by Making You Stand Out to Your Customers”
Original Publication: Gallup
Subject: Organization Questions

1. Who is in our target market, and where will these ideal candidates find us?
2. How is our culture reflected in our branding and job advertisements?
3. What attracted our best candidates to us, and what do they want out of a career?
4. How are we tracking where our best candidates come from and what they want?

Authors: Andrew Robertson, Ben Wigert
Source: “Why You Need to Compete for Employees Like You Do for Customers”
Original Publication: Gallup
Subject: Human Resources Questions