Should we pick a "boss" in a startup with friends?

I recently began working with two longtime friends on a startup, and we are hitting a wall when attempting to progress on anything.

We all possess fairly similar skills, so we can each handle any possible aspect of our startup. Everybody seems to want to handle the same "fun" aspects while neglecting the tedious bits. We are wasting weeks just trying to figure out who handles what..

So, we've been tossing around the idea of one of us becoming the "boss" and having delegation rights to make our group run more efficiently.

My question is : when you have a team of equally skilled people what factors can you use to determine who should lead the rest? (All of us have fairly equal managerial experience, even..)

Ultimately, every organisation needs a boss. Anyone can do the easy stuff, but there also needs to be someone empowered to make the hard, unpopular decisions and then take responsibility for seeing them through.

If you find it impossible to agree on one of you for this role, perhaps look outside for someone to be CEO, or at least someone who can moderate and facilitate, so that important decisions can be made.

This feels like one of those questions which it is impossible to answer without knowing the individuals involved - my first reaction is yes you should have a leader but, in this situation, I don't think it will work.

The reason I say that is you have already acknowledged that you cannot agree under the current arrangement - what exactly would change if suddenly one of you was "in charge"? If you truly believe that it would change anything then there is no reason why the current situation cannot work just as well and with no risk of any jealousy or other emotional factors leaking in.

To me, it sounds more like everyone needs to step up and realise that a startup is not all fun and that some of the less enjoyable tasks still need done and can often be as important, if not more important, than any other tasks.

Why don't you agree all the less enjoyable tasks which need to be done and then distribute them evenly between each other so no one person is doing all the laborious and boring jobs but they are being done which the key part of this and all without needing to get involved in the politics of one of you becoming leader?

Yes you should appoint a leader/boss and that person should be the one who wants to help develop the rest of you. At the end of the day, it will be the manager's role to get work done through other people.

Some factors which might help influence your decision include:

• Is there somebody who is less interested in staying technical as their career develops?
• Is there somebody who is more of a self-starter, and doesn't need to be told what to do?
• Is there somebody more respected amongst the group members? i.e. might have a little more relationship power to influence?
• Is there somebody who is genuinely interested in developing the team's capabilities?

With a bit of luck one of you will meet a few (or all) of these factors and they are likely to have more success at leading than the others.

Remember the decision does not have to be set in stone forever. Picking somebody is better than picking nobody, and, after 6 months or 12 months you can review the situation and perhaps the 'true' leader will emerge.

It doesn't matter how you decide, just decide that someone has each specific role, one of which is boss.

Choose by drawing lots if necessary.

You can set up in your bylaws rules about how the board chooses the boss, etc, so the role can change if the person first chosen doesn't work out well in that role. Provide OBJECTIVE evaluation criteria....

Your situation sounds similar to ours: we all do a bit of everything. We've been thinking of dividing up the work into clear areas (e.g., marketing, product), but in the meantime we organise ourselves with bug tracking software.

In the bug tracker we list everything outstanding: bugs, new features, marketing effort (time we spend on Twitter, PR...), whatever. The point is we put everything in there.

And then we all agree on what tasks go to whom. This way it's easy to see if anyone is getting to do more of the fun, quick and easy stuff than the rest.