What are the three most important questions you should ask your team about your performance as their team leader

I will describe my experience, may be it's helpful, may be not. I had a similar choice and I elected to join the larger organization - in this case a reputable investment bank.

Their graduate program was second to none (IMHO), and I learn a lot at the early stages of my career working in large (and small) teams, and had opportunities to experience lots of different areas of the organization. Pretty soon, got bored of being just a small cog in a giant system, and wanted out.

Now I work for a smaller organization with only a few software developers, but I'm at that point in my career where I am in the driving seat rather than being guided. And for a smaller organization that is perfect, no need for training, no need for additional time to get to grips with technologies, I am here because of my experience.

The point I'm making is that, at such an early stage in your career, you need the time and guidance to develop - which you may not have at the smaller institution. Once you have sufficient experience, the world is your oyster...

At the same time I understand your dilemma, better the devil you know... ;) However take the plunge, try something new... you may enjoy it...

The greater the risks, the more you need "air cover". This is what a manager is really supposed to provide. While the team does the work, the manager is supposed to ensure that there is nothing that will keep the team from achieving team goals. Whether it's tweaking the schedule, running interference between the team and the sales staff, or simply making sure the team are paid on time and that the coffee machine remains in working order. A really great manager allows the team to function almost as if the manager isn't there.

The reality of course is that most managers utterly fail at this. They either micromanage, or they are rendered obsolete so that the upper echelons of the company can control things more directly, and the truly great managers are a rare bird indeed. As far as a software team is concerned, there are some pros and cons both ways when it comes to having a hierarchical or flat team structure. If the team is very small, and the work done requires very little overlap (and by that I mean everyone has an independent project), then it's been my experience that a flat (aka unmanaged) team structure can work very well if all of the team members are disciplined. It's also been my experience however that where there is a great deal of overlap in the work that the team members do, where there are two or more relatively strong personalities, or where there is a relatively stressful working environment with a busy workload, then having a team leader or a manager with clearly defined responsibilities is generally essential.

There are a lot of factors involved, however it really boils down to the personalities involved, their individual motivations and career objectives, and the example and guidance provided by upper management that will determine how necessary a manager or team leader position is. Generally, if there is any chaos, and when the team is asking for it, then the team clearly needs leadership. If things generally tick along ok without management input, then perhaps the team can manage within a non-hierarchical structure for a time... at least until the workload and schedule becomes too difficult to manage.