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I'm tasked with realizing a project that was created by a visionary stakeholder. This individual needs to play a role in making the project happen day-to-day. But as we work towards deadlines, this person feels comfortable envisioning different versions of the future, rather than looking at a task list and picking things off one-by-one to accomplish. Deadlines get missed, and we're going to slip into the red zone if the behavior doesn't change.

I tried organizing work into Agile-like sprints, because there's a software development aspect to the project. But the visionary found this to be too pressure-filled and stressful and abandoned that methodology unilaterally.

What project management methods would tend to keep a visionary person on task? Would short daily status meetings tend to help? "What did you work on? What will you work on? What's the priority?"

This article seems relevant. It discusses specific change resistance tactics and ways to handle them.

"Crossing the change river is hard. Some cowboys who are true entrepreneurs will not be able to cross, others will. Our job as leaders is to help them try, and find the best seat on the bus for them, even if sometimes it is another bus."

  • I don't think this is a project management question; this is a workforce management question. If I were to answer, I'd suggest metrics (quality management), but I suspect that the individual would object to metrics on the same grounds as Agile. Ultimately projects are about closure, and that is intrinsically stressful and pressure-filled. Perhaps the individual needs a new line of work? – Mark C. Wallace Aug 28 '15 at 18:09
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You may have a difficult conversation to have with the stakeholder. To be perfectly blunt, work with no pressure or stress is called a hobby. I don't recommend you lead with that. What might help is this:

Agile (and it sounds like Scrum would be particularly helpful) focuses on getting work complete through small increments. You start with a foundation idea and build on it. Each piece is complete and shippable. Because each part is completely done and ready to go, you have absolute freedom about what piece you want to do next. This lets you make significant changes in direction down to the very last moment before the deadline. That approach he dismissed is what will give him the freedom he wants.

Another thing from Scrum that will probably help you is a product owner. The product owner has final say on what does and doesn't get worked. Your stakeholder might be the source of the ideas, but having the product owner control the backlog of work will put someone in the middle to ask questions like "what does this actually get us?", "why is it needed?", and "can this afford to wait?"

How you implement agile is a much broader issue than we can'y really handle here, but if you get your stakeholder on board with it being the avenue for the freedom he's looking for while still meeting deadlines, that's probably a fantastic first step.

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Mark Wallace is correct that this is primarily a people issue not a technology or Scrum-technique issue. Fortunately there are some people-techniques that work to resolve certain sorts of people issues. Your issue here is resolvable.

Daniel's answer touches (brilliantly) on the phenomenon here: that different personalities can have wildly different work styles and those styles are enduring and in many cases unchangeable.

You will not find a Scrum technique that will make a person change any of the unchangeable aspects of individual work style.

Here are specific techniques for harnessing the strengths of your visionary stakeholder while still getting useful work out of them each day.

FIRST - Be realistic about what work they can and should do. Do not make any work assignment based on what you feel they OUGHT to be able to do, only assign tasks that they have shown they ARE able to do, or almost do (so they can stretch, grow and do).

NEXT - Assess how this visionary gets his juice. Does it primarily involve them talking? Do they seem to need an audience? Schedule a daily brief talk with them where you act as audience. Harvest their good ideas. Keep this brief by using a timer.

NEXT - Give the visionary the additional payoff of placing their continual stream of ideas into a visual Parking Lot. Sharing an idea that others ignore is a downer; sharing an idea and seeing it parked somewhere feels validating -- and frees the mind for the next thought.

NEXT - Many visionaries hate to eliminate or rank ideas. Make him do it anyway. "We can only work on one thing at a time. Our priority from the customer is X. Which new idea is actually more important than X or should come prior to it? Why? What will we then choose to NOT do, in order to do this new thing?"

ALSO - Hold this conversation near your visual tracking tool or Scrum board. Help the visionary see the current reality. Ask, "What can you personally accomplish today to move us forward?"

REMIND the visionary that doing the 2nd, 3rd, Nth awesome new idea they've spawned, is dependent on getting the 1st one done SUCCESSFULLY.

Look for clues, hints, and tells from the visionary's past and present, that show you how to get the best work from him. Does he need someone to pair-program with or talk things out with? Does he respond well to distant deadlines but collapse under the pressure of a shorter one? Do calendar reminders work? Gold stars?

REMEMBER that the visionary is an idea generator. Give him little problems to solve that are in his sweet spot, where the answer is not obvious. Think of him as an idea-hose, and point that hose at an area that requires a flow of ideas.

You can also set the visionary to work on diagnosing himself. Ask him to reflect on where and when he's been most productive. What was the work? What were the deadlines? What was the context and content? Aim his idea-hose at his own performance. (He's probably secretly just as irritated by his inability to sit down and crank out work as you are.) Keep the tone positive, relaxed, curious, accepting.

This topic is at the heart of an e-book I'm writing that's inspired by Drucker's "On Managing Oneself" -- excellent reading, available I believe at HBR.org and of course fine bookstores, libraries, and Amazon.

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