Planning at the Inception

Start your program off on the right foot, then run like hell

Drew Harteveld
6 min readFeb 5, 2024
Copyright Warner Brothers Pictures

Let’s take a few minutes to think about planning at the very inception of a new program. We’re not talking about after the kickoff or once all resources have been engaged. We’re talking about during those initial hours when a business reality has forced senior leaders to contend with the fact that a large effort may be necessary to plug a hole in the current situation, and they are trying to sketch the outlines of that effort.

Often this scenario looks like just a handful of those leaders in front of a whiteboard, likely after-hours, perhaps with a half-eaten pizza on the table. With any luck, there’s also a bottle of scotch that one of them learned to keep in a bottom drawer for situations just like this one. Diligence during this initial brainstorming session will plant seeds that may define the success or failure of the program months down the line.

DISCLAIMER: In both this space and my business as a whole I try not to be overly prescriptive. I have learned from experience that the best operational solutions are organic and built-for-purpose. Just because I’m not familiar with your ways of working doesn’t make them wrong. I show up to learn first and teach second.

I show up to learn first and teach second

However, in this critical phase of program inception, there really is a RIGHT WAY to move the conversation forward. For my own shorthand, I utilize the progression: WHAT >> HOW >> WHO >> WHEN .

The order here is just as important as the underlying concepts. I’ll describe each below, and then we can talk about interplay.

1. The WHAT

Without question, in 98% of cases the only right place to start is by defining the target state for the product or service being created. Beware the trap of contextual framework in defining this scope. Something you consider to be an obvious inclusion might be nonexistent in another person’s context. For this reason, be as specific as you can at this high level. If you want the Content Browse feature to be driven by a carefully maintained taxonomy, add that to the list. This isn’t a formal specification, but we definitely want to clearly include the critical attributes of each part of the envisioned scope.

2. The HOW

Now that the WHAT of the scope has been clearly defined, at a high level, we are in a position to sketch out the HOW. What talent, equipment, technology, knowledge, licenses, and partnerships will work together in order to realize that WHAT? What rules of engagement will be established to keep this effort on the rails and moving forward? If there are multiple approaches available, how will we choose and how should that adjudication activity be included in our planning process? The WHAT is theoretical. The HOW begins to crank that theory down into the practical realm.

3. The WHO

The next step is to determine what roles, resources, and specific expertise will be required to make that HOW a reality. Begin to sketch the interplay between different individuals or groups that will be required to bring this idea to life. Try your best not to jump ahead into the scheduling idiosyncrasies of different resources, equipment, or environmental factors. For the moment, keep staffing high-level and theoretical, “Three concurrent teams under a program governance structure, plus UX and Infra shared service engagement throughout…” That’s the level of detail we’re looking for at this juncture.

4. The WHEN

Only now that you have clearly defined the WHAT, HOW, and WHO, are you in a position to begin blocking out a high-level schedule. There are a bunch of constraints to consider during this part of the thought process:

  • Business Cycle
  • Availability of internal/external resources
  • Impacts of this effort on other initiatives underway in parallel
  • Outputs from initiatives necessary as inputs to this effort
  • Availability of specialized equipment
  • Environmental factors [EX/ we can’t pour the foundation during the monsoon…]
  • Aspirational target delivery date

It may take a few tries, but these will eventually snap-together into some kind of cohesive puzzle that shows your HOW rolling out across time.

Attribute Interplay

As soon as these four attributes have been defined, the negotiations begin:

“The deadline won’t allow us to address all the scope desired. We’ll need to cut our WHAT down to just these essential elements…”

“While we have this HOW and WHO engaged, there are a few items of technical debt that it makes sense for us to knock off as part of the WHAT…”

“Dr. Taylor has critical expertise in this area, but is not available until next year. Since we can’t wait that long we will have to utilize a less-expert WHO and add another 8 weeks to the WHEN to allow for some learning along the way…”

“We all agree that this WHAT is important, but in light of other high-priority initiatives there won’t be an open lane of WHEN for this program until Q2 of next year…”

This massaging of the previously-defined attributes represents the best path to success in this exercise. As with all intellectual collaboration, compassion, tact, and an open mind are critical to effective dialogue.

As with all intellectual collaboration, compassion, tact, and an open mind are critical to effective dialogue

Please don’t make the mistake of pouncing into negotiations before the basic WHAT, HOW, WHO, and WHEN attributes have been initially defined and documented. The human brain isn’t so hot at this ‘breadth first, then depth’ approach. We tend to get in a lather and dive right down the rabbit hole.

In order to make the most of this exercise, we need to coach each other to peel the onion one layer at a time. The concepts defined and shared during that initial round, before the negotiations begin, become the objects we all move around the map while the negotiation is underway.

What About Budget?

Even the richest of enterprises still operate within some kind of financial guardrails. There is no question that cost is a critical constraint to all program planning. However, in the scenario postulated here, a small group of senior leaders huddled after-hours to try to work through an intractable business problem, we really don’t want to get into the details of dollars and cents. At this juncture, we want to focus on what is theoretically possible with the assets available, not be limited by what is financially feasible. Nobody ever invented the future by starting with accounting (no offense, Tom Bliss).

Nobody ever invented the future by starting with accounting

We may be forced to run a secondary round of negotiation once we introduce cost into the picture. Better that than to be limited right out of the gate by budgetary realities. To quote the great Kenny Rogers, “There’ll be time enough for counting, when the dealing’s done.”

Start Off On The Right Foot, Then Run Like Hell

I’ve been in that postulated room, with the pizza and the scotch, many times throughout my career. It’s exciting and daunting, and in my experience the enterprise rarely finds itself there willingly. More often, business realities conspire to force our hand in sketching out a solution to a problem that can no longer be ignored or cost-effectively held at bay.

During those initial moments of inception, envisioning the future program attributes in the right order helps mitigate the risk of missing crucial details. Due to the operational mechanics and hierarchical structures of modern enterprises, oversights generated during this early planning might lie dormant for weeks or months. By the time we recognize these errors it may be too late to fix them without large impact to the program, its budget, or the enterprise as a whole.

We avoid these oversights by taking a breath, envisioning program inception in the right order, getting it all on the whiteboard so our syntax is in synch, and negotiating in good faith toward a feasible solution.

At the end of this inception process, we’re still only at the very start of the program. But handling this part with good diligence provides the firmest possible foundation upon which to build everything that comes after.

Originally published at https://www.linkedin.com.

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Drew Harteveld

BUSINESS PROCESS & OPERATIONAL LEADERSHIP; I organize people, process, and tools to create scalable delivery to the market.