So, the question that I am trying to answer here is: "Would I be comfortable investing my own money with this team?". There are a number of attributes that I look for when reviewing, but the most important by some distance, is the first one of the list below.
Honesty and Integrity
You have to be able to trust this team and in particular, its leader, if the investment is likely to stand any chance of success. For clarity, this is not about liking (or not liking) an individual ... it is about irrespective of differences of opinion, do you trust this individual and team to do the right thing. This can be hard to assess based on limited interaction. Sometimes all you have to work off is a couple of telephone calls, where you cannot see the body language. This is particularly the case if the business is early stage or the sum of money involved is small. Naturally, I prefer to spend time face to face in order to really understand the leader and the team. However, it is usually pretty clear if something is amiss, even if you are not sure what it is at that point.
Drive & Determination
Particularly in startups and high growth technology businesses, the technology team (which is often just one person) has a lot to contend with. Building a product and supporting it, thinking about the future at the same time as mitigating technical debt, can be a tough gig. So I look for personal resilience, grit and a desire to win as I know that these qualities are key to success. This area can be a challenge, particularly around the personal resilience, as there can be an aspect of personal burn-out involved, so it can be important to (sympathetically) ask about this subject.
Creativity & Planning
I appreciate that these two areas do not commonly get put together, but in this situation I think that they are two sides of the same coin. Of course, I expect there to be a technology plan and yes, I will be assessing how realistic it is. However, I am equally interested in the team reaction to what happens when the "wheels fall off". How creative is the team and how quickly can they come up with an updated plan? In particular, I would want to know if they have already thought about the aspects of greatest risk to the current plan and what they would do if they were to materialise. Of less importance, but still of interest, is gauging just how creative the team can be whlst under intense pressure.
I look for a number of aspects in the leader or leadership team, such as confidence, capability to work under pressure and a good IQ/EQ mix. Personally, I like leaders who care about the well being of their staff, as I believe that makes the staff more likely to follow that leader. I also like to understand their experience, their track record and particularly, gain an insight into what shaped them as individuals. Finally, depending on the situation, I look for a capability to sell and customer empathy.
You may wonder why I did not make leadership my number one attribute as, after all, it is all about the team. That is true and in startups/early stage high growth businesses, all of the above are most likely apply to an individual. However, as the business and their technology teams get larger, the risk from rogue employees/contractors/partners dramatically increases. I have seen organisations laid low by the actions of an individual who was not the leader.
So, going back to my initial question ... would I invest my own money with this team? A lot of the above helps me collect my thoughts whilst I also listen to my gut. Having met so many people over the years, after a while you just get to know if something is right or wrong. Just to re-iterate, this is not about liking (or not liking) someone ... those thoughts have no place in this process. It is about the ability to deliver a successful outcome for the investment.
I hope that the above may prove useful. Please feel free to add your own thoughts in the comments section below.