Chris Mann

This question has me thinking about creating an opportunity to increase everyone's skills. Look for areas where the collective team needs to get smart. Break up topics, assign them to different people. Have teams of two or more collaborate on research on a given area of AI, write up their learnings in a google doc and again, review in depth with the team. Here everyone gets smarter and gains more appreciation for each individual's contribution creating a stronger team bond.

Ask each team member to collaborate on a unified Google doc that will become your AI goals manifesto. Have each member author key sections to the doc. One day before the meeting to review the doc, require all authors to send out their sections for pre-reads. Require all meeting participants to pre-read the docs and comment to show they are pre-reading. During the meeting have each author explain their written content in detail and leave plenty of time for discussion. During the meeting capture unresolved issues and detail the additional information needed to resolve any differences in perspectives. If needed have follow-up exercises to capture the data, share it and review it in a similar way. This should set your teams alignment.

Over all, I might suggest optimizing for culture fit. This is not a small or large company thing. This is the culture of the group of people you will be working with. Do you like these people? Do they value your ideas? Are they open to input and will they adjust to that input? Does the team demonstrate good healthy communication patterns amongst themselves or are they having alignment issues before you join? Do you see yourself being happy working with these people? This is not a large or small company question.

A lot of this comes down to how you manage your time and the perspective of your managers. In most situations your work-life balance is largely in your hands. Learn how to ask for the right resources to get things done. Learn how to show management what success looks like and to communicate when you are overloaded. If they are not supportive either you are not presenting a good case for your product plan or you are in the wrong place. On the other side, start-up life can get very all-consuming particularly when the company takes fire. It can be so damn fun and rewarding there is nothing you would rather be doing. I've found this a couple of times and I can tell you it is one of the best experiences in life. Its not easy to find!

Part of being an entrepreneur is learning to de-risk your situation. When I was choosing to go to my first start up I had two young children and was very afraid of losing my job due to the company going out of business. At that time a mentor gave me a perspective that showed me the upside I was not seeing and that was that I already had a fantastic resume and this start-up was going to pay me to become an expert in a new hot emerging field. If they go under I am even more valuable in the market. I took the job and we had a very nice exit about 4 years later. On the other side I've been in numerous start-up situations that have run out of cash. If you play the start-up game you will experience the odds of the star-up game!

I am a fan of the start-up life. Everything you do every day matters to the people around you. The feeling of comradery and shared purpose is an incredible experience when you are in the right culture. Yes, in a large company, you might roll out a product to 1000's of users, however, you'll be lucky to meet these users in any meaningful way. It will be numbers on a spreadsheet. If that is your jam then go to a big company.