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I would love to see how others deal with this issue as well.
Never heard of a project or program where management wanted to dismiss or be dismissive of planning.
While it is unlikely that a senior manager will clearly declare that planning is wrong, there are instances when they are ready to "let you play with it, as long as it does not get in the way of the real work". This is probably less frequent in mature organizations, but I have found this situation more than once.
I would like to say that I found a winning general strategy but, truth is, I had to manage these (fortunately not very frequent) situations on a case-by-case basis. In some cases I remember doing some bare-bones scope/time/cost/risk planning with a core team while doing "real work" noise to keep that diifficult stakeholder happy.
In my personal experience management has often dismissed planning. I think that's because the management I worked with didn't want to deal with many long-standing issues proper planning would require them to face, so they hoped to achieve their goals through a 'quick and dirty' method.
You might explain to your management that improper planning will cost them more time and resources, and decrease their odds of success. Try showing them practical examples of how this is the case. Detailing the results of failing to identify an important project requirement is a good way to do this.
I too have had this issue years ago. Truthfully, this all played out quite dramatically. There were many things going on that I was not aware of and later I realized that they resisted planning and documenting because they had things to hide. Four people ended up being arrested. Three of them were charged with 50 counts each of things like bid rigging, utterance, etc. They were setting up fake companies to bid on contracts. When one of these companies won the contract, it would hire subcontractors or they would do the work themselves. It was a mess. They did end up doing some jail time and are on probation for 10 years.
But back to your question, the way I dealt with it at the time was to insist upon doing some form of documentation before I would start the actual work. Even if I spent a day to write up what I thought they wanted and review it with the customer. I took heat for this, but I refused to just wing it. Would I have liked to have more time planning, of course, but I was being pressured and had to compromise.
After upper management changed there was still some resistance to planning because that was the way the project managers had been operating for so long. I helped to establish and use the processes for planning and eventually the others followed suit. The new management was no longer against planning, but they were also pretty "hands-off". Therefore we had to work on or own processes and procedures.
Now we have new management again (don't worry this time it was a result of retirement not law enforcement) and they fully embrace following PMP guidelines. We are setting up a PMO and training all of the other managers.
It was a long road to go from where we were to where we are, but we are finally there.
Selling the value of planning is different than asking for big, heavy planning up front. The former is crucial, the latter is usually a waste of effort.
What people must understand is: there is a plan always in place. Always. Degree of formality is what differs mainly tied to the step inside the organizational life cycle the organization is.
I faced that recently and after 10 months of trying left the project in good terms.
I could not get them to buy in what I want to do initially .. All my long term planning was dismissed.
I learned a lot from this experience, that you need to sell them the value of planning and do it in small portions, do not complicate it.. Let them see some results in short terms even if you beleive that it should not be this way. Listen to them what they want and mirror it into your plan. Most of them they look to short term results to show off.
Sometimes there is a lot of pressure to get started due to financial or legal reasons but that doesn't mean you cannot plan as you execute. I've been in a few projects where the team know the basics of how to begin so I've had to let them start work while we plan in parallel.
I have never been in this scenario. In fact, in some of my engagements, I have often faced the opposite problem!
Stakeholders demand a precise plan for every activity 6-8 months in the future with a lot of unknown variables yet to be resolved (instead of progressive elaboration). My risk register documents alone topped 5mb in size for some of these projects.
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