Annual Check-in for Leaders Part 1 — How Are Things Going?

When it comes to your team/company/organization, how are things going?

When was the last time you paused to survey how things were going? We’ve crafted a three-part leadership-level survey to help reflect on your team, the company, yourself, and what you’d like to see more of. Give yourself a block of time to journal or work through these questions. Then, take some time to read back through your responses. Where do you notice where you might need support?

In Part 1, we’re sharing some impactful questions to help you reflect on the question: “How are things going?”

Leadership Team Level Communication & Decision Making:

• Do the leaders debate or examine contentious issues well? Where do you see this happening well? Where can it be better?
• Can everyone on the leadership team have conflict with each other? When conflict arises, how does the team work with it? Where could this be better?
• Do you make good decisions together that have buy-in or shared acceptance? When and where has this happened easily? Where and when has it been a challenge? What is currently working well?
• Are decisions made in a timely manner? What is working well here? What would you like to see more of? What is in the way of this happening well?
• Where do you not have full trust in your team?
• Where do you trust when healthy skepticism might be more appropriate?
• How well does your exec team communicate and make timely decisions without you being there?
• Does your team know when to make decisions without your presence or engagement? If not, what would you like to see more of? If this was happening well, what would you be seeing?
• Do you and your team have well-established and successful patterns of communicating leadership decisions to other levels within your organization and/or beyond? What might be missing? What would you like to see more of? What do you notice when this is working really well?

Strategic Alignment:

• Are the Co-Founders and leadership team aligned? What does alignment mean for you?
• Is the board in alignment as well? How do you build alignment or at least support with your board?
• Is the strategy translated into a roadmap and used effectively across the company? What tells you this is working well?
• How well do your employees understand how their goals and deliverables roll up into the company goals?
• How will a typical employee answer when asked what the company’s strategic vision is?

Execution and Accountability:

• Will your current leadership team level up to meet upcoming demands?
• Do you and your team have clear expectations, access to development support, and feedback related to leveling up? If not, where do you see this falling short? What are the risks of not addressing this? If this works well, what do you see as the outcome of this working well on the team?
• Are people working on the right things? Where do you see this working well? Where might adjustments be made?
• Are people working in the ‘right’ (healthiest, most productive) ways? What tells you this is so? What do you notice in individuals and the team as an outcome of this?
• Where is there a high degree of accountability across the organization? Where could there be more?
• What are the consistent ways you address accountability gaps or failures? What would you like to do more of? What might you want to do differently?
• Are you surprised by accountability misses, or is there a lack of transparency (honest assessment of progress along the way)?
• Where are commitments being kept within the organization? Where are commitments being missed?

Culture:

• Where in the organization are people inspired and working well together?
• Do people throughout the organization understand and embrace the foundational attributes and characteristics of your culture? How do you know?
• Is the culture getting watered down as you grow? What are you noticing here?
• Is there significant turnover? Is turnover greater than you believe it should be? Is it greater only in some areas of the organization? What might be contributing to this?
• Is what’s made your culture successful scaling to the next phase of growth?
• Managing senior leadership for the first time: what issues are present here? What are the areas for support, improvement, and growth in your leadership of the senior leaders and in the senior leaders themselves?
• Co-founder issues: How is this affecting the team?
• How are co-founder issues affecting the ways you work successfully together? Are the co-founders or co-leaders prepared to work on the problematic dimensions (not let them fester further)? What do you notice about the co-founder dynamic? How does this affect the team at large?

On a scale of 1–10 (10 = Fantastic, 1 = “Not Sure” or problematic) rate the following focus areas of the company:

• Business Strategy
• Organizational Design
• Company values
• Communications within the organization
• Goal setting
• Board management
• HR Issues management
• Scaling operations
• Hiring plans, processes, and success
• Business/organization development and sales
• Match to Market
• Financial Management
• External communications, PR, Brand Presence

From where you sit, what are specific issues that need to be addressed in each area?

In Part 2 of our annual check-in for leaders, we’re shifting the question from “How are things going for the company?” to, “How are things going for you as a leader?” Access Part 2 here.