Playing 20 Questions: The Perfect Script To Size Up Your New Team

Read Time: 2 minutes.

I wrote a post last year about the optimal way to use your first 100 days leading a new team.

Given the stakes are so high when you take on a new team, we get a lot of emails asking for more details on Phase 1: Understand. They want to know what the right questions are to ensure they’re building a complete picture.

In my first draft, I came up with a list of more than 100 questions. That might be exhaustive, but it’s not that useful.

You don’t have that kind of time.

I settled on the 20 highest-signal questions for 4 critical aspects of your team.

Get these questions right and you’ll have all you need to lead.

1. TASKS (Understanding Work)

I want to see the work through their eyes. I want to determine what’s critical keep and what needs to be improved or removed.

• "How do you measure success in your role?"

• “Take me through your view of what excellence looks like for our team?”

• "Walk me through what you believe are the team's 3 most critical deliverables right now?"

• "Where do you typically get blocked or slowed down in your work processes?"

• "Which parts of our processes feel unnecessary or overly complex?"

2. ENGAGEMENT (Understanding People)

I want to start building a vivid mosaic of what each person is like. And look for opportunities to alter the environment to help them win more often.

• "What aspects of your work energize you the most?"

• "How do you prefer to communicate and receive feedback?"

• "What skills or capabilities would you like to develop in the next year?"

• "When did you feel most proud of your work here?"

• "What makes up a 'great day at work' for you?"

3. ALIGNMENT (Understanding Direction)

Individual motivation and team momentum both sit on a foundation of alignment. I want to uncover any cracks that could lead to a collapse in either.

• "How does your work connect to the broader company mission?"

• "What do you see as our team's biggest opportunity in the next 6-12 months?"

• "Where do you see the most friction between different teams or departments?"

• "What decisions or information would help you work more effectively?"

• "What's one thing our team is doing that we should stop doing?"

4. MOMENTUM (Understanding Progress)

It’s one thing to be aligned on a direction and another to be making progress towards it. I want a constantly compounding team and here I’m hunting anything slowing progress.

• “What's the biggest improvement you've seen in the team over the past year?"

• "Where do you feel we're falling behind our competitors?"

• "What recurring problems keep coming back despite our attempts to fix them?"

• "Which of our recent changes had the most positive impact?"

• "What's one change would immediately improve our team's performance?"

Podcast Alert

This week’s podcast: Entrepreneurial Excellence

Some new topics we covered:

• Why I believe personal sovereignty is the best form of wealth.

• How high-performing teams create company culture

• Work/Life balance vs peak performance

Find it on Spotify, Apple, or your favorite platform.

What You Missed

Did you miss this week’s Monday MGMT Minute? 

📌 Learn my favorite trick for getting people to welcome my feedback.

What you missed from Dave on LinkedIn:

•  11 Career-Limiting Lies (+ tips to embrace the hard truth)

• 🚩 7 Subtle Signs Your Best People Are About To Quit

• 10 Bad Management Habits I Had To Unlearn To Lead Effectively

What you missed from Dave on X/Twitter:

• The Simple Formula For Leadership Success

• Don’t Reward Top Performers With More Work

• The Virtuous Cycle of High-Performing Teams

What you missed from Marsden on LinkedIn:

•  😱 RIP To Shyness And Self Doubt Stealing Your Success

• The New Manager Survival Guide (step up w/o burning out)

• 8 Cognitive Biases That Trick Us Into Bad Decisions

Our goal is to build a community of 1 million thoughtful, curious leaders.

Your ♻️ reposts on any or all of the above are always appreciated.  

Thank you for reading. Appreciate you!

Dave & Mar