Thanks for inviting me. While you’re enjoying the Photoshop version of me awkwardly crashing your staff meeting, I hope you’ll carefully ponder your answers to the questions.

For all of these, I’d want to go around the table and hear from you and your leadership team.

What are you working on right now that has you the most excited and why? I didn’t ask for the thing that you’re spending the most time on – that might be some ugly operations problem that’s plagued you for months. I want to know the idea or initiative that sucks up all the spare thought time – when you’re at the gym, driving, or brushing your teeth. Most likely, it’s the thing that you believe represents opportunity, growth, or renewed vitality for the organization.  

What person in the company most accurately embodies the company’s values, vision, and mission and why? In a perfect world, this would be almost impossible to answer. Ideally, you and your leadership team are so adept at modeling and communicating the culture, every team member is effectively living it out. But, if that’s not the case, what are the gaps in the culture transmission initiatives.

If you could clone one person in the company (it doesn’t have to be someone in your workgroup) who would it be and why? This is an exercise in identifying needs. If you overwhelmingly choose someone for their technical skills or subject matter expertise, this might be a risk assessment. If the operational strength or knowledge base of the company resides in one person or two people, your long-term organizational health could be at risk if something happens to them. If you choose someone because of their attitude or approach to work, use those attributes to reshape your screening process for new employees.

Does every employee in the company know the management team’s strategic priorities right now? They might be crystal clear to you but they might not be to your team. You might be laser focused on lowering defect rates on the factory floor but someone outside that workgroup might be blissfully ignorant of the problem you’re trying to solve. By virtue of their typical job priorities – let’s say it’s quicker delivery times – they might be working against you as they try to get product out the door even if it’s not perfect.

If you asked your team members how they determine if the company is winning, what would they say? Everyone wants to be a part of a team that’s succeeding. It’s pretty easy to identify the metric if you’re playing a sport – wins vs losses, points scored vs points allowed. It’s much more difficult if you’re working in a business – especially a small business. Publicly traded companies post “scores” every quarter, but small businesses might, understandably, never release financial results. That makes it even more important that team members understand what metrics constitute winning.

Why do customers buy your product? Of all the things that organizations must understand, how they create value for clients has to be close to the top of the list. If you can’t define it simply and clearly, how will your maintain it? How will you duplicate it for successor products? How will you extend it for business growth?

If you could snap your fingers and make one problem in your organization go away, what problem is it? Did your mind immediately go to the big threat, the looming disaster, the thing that keeps you up at night – the new competitor that’s quickly pick up momentum, the shift in the industry landscape that could signal the end for your organization. Or, did you think about the nagging problem, the one that’s like a dripping faucet – the employee that needs to go but getting rid of them is going to cause such upheaval you’re putting it off, the vendor that used to be great but now they’re not and replacing them is going to be a monstrous task. Then I’d ask why. Why that problem and not a different one. What eminent threat does that particular problem pose? That’s probably the challenge that deserves the attention.

Good questions will change the conversations inside your organization. Good, actionable answers will change the organization.