This came in by email:

I would suggest that the most effective person to lead a change effort is a former skeptic, who is now a true believer.  They can relate to (and have some credibility with) those folks who are still skeptical, but can share why they are now a true believer.

Thanks for a great blog.  Terrific content.  One of the best on the web.  Love Kathy's website, too. (www.startcooking.com)  

David, I'd steer away from the extremes and seek a balance of the two. I don't want a yes man/woman who parrots the corporate slogan, but I also don't want someone that's going to torpedo the process. A person with a proven track record who is confident enough to call things as he/she sees them would be a good fit.

I've been responsible for over 50 MRP/ERP and several hundreds of IT Service and Asset Management implementations. 

I've seen both approaches - the skeptic and the "true believer."  If I have a choice, I'd go with the true believer every time.  Best would be if the true believer has a "risk manager", skeptic, chicken little on the team. 

Skeptics tend to self-edit the projects, filtering out even all but the most easily achievable things.  While they achieve a lowest common denominator, they do not achieve what is possible.  Skeptics can suck the life out of any project, out of your day.  Little progress can be made whan the only response is, "we can't do that here, because we've never done it before."

True believers need to be moderated so that the message can can be made more clear to the "masses."  True believers tend to get too far "in front" of the rest.  But, true believers, once taught the principles of personal persuasion, bring a degree of enthusiasm to the effort that can be infectious. 

The awful truth is that more than 50% of projects fail to substantially meet their objectives.  Progress should be measured as a comparative differeence, not as an absolute against some objectives established before you knew better and when your optimism bias was in full force.  Failure of system implementations is rarely caused by technical reasons - almost always by internal politics.  Successful teams make a long-term commitment to success.

In the movie The Wedding Date, the proposition is that women have the relationship they want.  I don't know whether that is true.  But, I do know that, when it comes to system implementations and their effectiveness, management teams get the result they want and will commit to.

Go with the True Believer - at least they'll get you further than you'll get with the Skeptic.

I'd choose a believer. Every time. When the leader doesn't believe in success why others should? If the leader isn't all enthusiastic about the project how he expects to bring the team to higher level of engagement, performance and enthusiasm?

Skepticism is like an anchor - you need one on the ship, but you don't place it on the bridge.

A recurring theme and problem I've encountered over the last few years is a chronic lack of time to devote to non-immediate initiatives. Yes, there are probably things I can fix to sort out this problem, but this time I'm playing doctor not patient!

If this is your scenario too, then the real danger of appointing a skeptic is that he or she is unlikely to wake up in the morning energised and invigorated to push this initiative ahead. I accept there can be strong arguments in favour of a skeptic in terms of the quality and practicality of results achieved, but only if something is actually produced!

That aside, I'm a big fan of Edward de Bono's 6 hats of thinking. One of these hats that the group is supposed to wear is the Black Hat. The Black Hat stands for logical, analytical, judegemental thought in a "negative" manner:
Why won't this work?
What are the problems with this approach?
What could go wrong?
What are the risks?

This is very much along the lines of a Devil's Advocate, except the focus here is on ensuring that the entire group accepts that this is a useful step, rather than becoming frustrated with the natural or allocated Devil's Advocate who pours cold water on new ideas.

As long as someone in the group is good at Black Hat Thinking, or as the theory encourages, the group themselves are actively encouraged to don the Black Hat regularly to vet their own ideas, the convictions of the chair shouldn't matter unless the person puts a personal agenda ahead of the clear conclusions of the group.

For more info, check Edward de Bono's original book (ISBN 0316178314) or google for some references.

I would avoid both. And, in fact, I've found that rather than a "skeptic," firms tend to appoint (or allow) the "pseudo-supporter." This person has a personal agenda to fulfill and will get on board with any change initiative as long as he/she believes it will suit their interest or enable them to "get ahead." When they realize the initiative will not deliver (as they had hoped) they become a "blocker;" either through passive or aggressive means.

Instead, I look for someone in the second row (neither front nor back) to work with. She/he is a respected member of the team and is known for their contribution to the entire organization. Having him/her on board forces me to clarify the points of the change initiative in a manner that can be (rather than "should be") embraced.

True believers and Skeptics are two extremes of the spectrum. I would chosse a person who stands to gain the most from the change. Once the person is convinced of the benefits of the change, the chances of their actively shepherding the changes  would be much higher.

In my experience, during a change process one goes through phases in which one is either a true believer or a skeptic but these are not static positions in implemeting change.

I would go with the person who had the most skill at managing change and who had the most credibility for driving the particular effort.  If they weren't a believer, my first job would be convincing them of the importance of the change.  If I couldn't convince the person I wanted to lead the change, I'd have to question how anyone could convince a whole organization to go with the change.

David is touching on a very important point regarding the orientation of the project manager.  There is another variable to consider here as well as the "enthusiastic" or "skeptic" orientation.  Both of these project managers must have enough knowledge of change management and a process for addressing it so that his/her orientation (whether favorably or unfavorably disposed) does not weigh too heavily in the process.  The ability to objectively gather data regarding the reasonableness of the solution and the degree of difficulty of completion is a key competency of the project manager...no matter what his/her orientation.