Starting with a Plan is Wrecking Your Product. Here’s How Winning Starts with Strategy.

The strategic PM

This woman and her team have put in the hard work and are ready to plan. Image via Midjourney.

Breaking free of planning’s iron grip.

“What’s the plan????”

I’ve been consulting in Product Discovery, Design, Delivery, and Management for over 20 years, and planning seems to be the only mode that gives people a sense of control.

Literally everything relies on “The Plan.”

Large Legacy Enterprise organizations in highly-regulated verticals like financial services and healthcare are required by law to have plans, and are audited for compliance.

Which is ironic, because as we’ll see, traditional approaches that start with big, heavy, up-front planning more often than not result in failure.

The downsides of inflexible planning

I’ve successfully led multi-million dollar efforts with 20+ person teams building large, complex applications in heavily regulated spaces, and have seen it all.

I’m also twice-certified in strategy and goal-setting, and always found strategy came naturally to me.

Despite the intense push in every situation toward planning, I always felt a natural affinity with the importance of going upstream and starting from strategic choice-making.

It never made sense to me how some colleagues insisted on starting with laying out the most intricate and elaborate plans.

They frequently ignored the human element of the people they were collaborating with to do the work, refusing to listen or respond as conditions changed.

Worse, they would rarely, if ever put any thought at all into the clients on the receiving end of the work.

The Traditional Approach to Failure

large study revealed traditional delivery approaches that start with big, heavy, up-front planning lead to failure in the majority of cases.

The same research uncovered that iterative, strategy-based approaches had proven to provide far greater opportunities for better outcomes.

What is it that starting with planning causes us to miss?

Why does it matter?

What are the differences?

Planning

Planning is an

  • Internally-focused,
  • Analytical approach

Focused on making the most of things within our control:

  • Our People
  • Time
  • Resources

With the goal of optimizing for efficiency.

To produce some end result we think should achieve our internal goals.

Strategy

Strategy, on the other hand, is a

  • Client-centric,
  • Creative
  • Problem-solving framework

Focused on making choices to influence something out of our control:

Customer behavior

With the goal of optimizing for effectiveness.

In ways that mean success both for our clients, as well as for our business.

The value of strategy

Every year, business schools churn out tens of thousands of MBAs trained in internal and analytical-based thinking.

It’s not surprising, then, that planning becomes the dominant mindset across most companies.

But that doesn’t mean all companies ignore strategy.

In fact, a core competency in designing differentiating strategies forms the foundation of many of the world’s most-loved, successful, and lasting products and service businesses.

What sets these strategy-focused businesses apart?

An emphasis on great client experiences.

The 3 Things before you Plan

But starting with a plan unleashes a chain of events that makes it almost impossible to keep user needs front and center throughout the Product Discovery and Delivery process.

But if Strategy is the key to effective action, in what ways can we shift to better support moving from our strategy to reality, if not planning?

There are three key elements that need to be in place before we’re ready to plan:

#1: Uncover the Client Problem

#2: Collaboratively Design Choices

#3: Map People and Potential

Steve J. & Steve W. — images courtesy of Andy McNally.

#1: Uncover the Client Problem

Strategy starts with Clients

Yes, sales are down, and customers are abandoning our software product.

But the mistake here is to make those inward problems the only problems we focus on, and only target hard sales and user base growth numbers.

“Figure out how to make these numbers, or else!”

The point of this step is to understand that sales and user growth are output metrics, lagging indicators that result from client behavior changes.

If we try to “plan” our way to better internal numbers at this stage, our success is most likely to be temporary at best.

Worse, short-term, internally-focused “hacks” may give us small bumps to our numbers, but could end up costing us our most loyal customers.

Strategy means influencing things out of our control

Our best option is to go upstream, listen, and start with strategy.

Strategy is specifically designed to influence something inherently out of our control: User Behavior.

Once we’re able to understand client unmet needs, we stand a chance of making a far better set of choices to create happier clients.

Happy clients who, in turn, will be more likely to find our products compelling, come and stay longer and with whom we can develop better longer-term relationships.

Reverse-Engineering our current strategy

But before we can see where to go, we’ll need to put what we’ve been doing in context.

At this stage, our cross-functional core strategy design team takes a step back and collaboratively reverse-engineers our current strategy, using the 5 boxes of the “Strategy Choice Cascade”:

The key here is to map our current choices across the areas of:

  1. Winning Aspiration
  2. Where to Play
  3. How to Win
  4. Must-Have Capabilities
  5. Enabling Management Systems

Our goal is to understand how effectively our current approach is addressing client needs, and begin to frame a problem statement.

(Note: No planning yet.)

Speaking to humans clarifies the problem

Next, we speak with our customers.

Having regular client touch points is critical for us to understand their feelings, concerns, and unmet needs in ways we’ll never get by reviewing data.

After a few of these conversations, these conversations, together with our reverse-engineered strategy will give us enough information to frame an upstream problem from a client-centric point of view.

It doesn’t have to be perfect — just upstream enough, and client-centric enough to get started.

Something along the lines of:

“Clients appear to be favoring our competitors’ combination of hardware and software solutions over our software-only approach.”

(Nope, still no planning yet.)

Moving from Challenge to Opportunity

Working from our client-centric problem, we use the power of Design Thinking to take that problem and open up alternate possibilities by framing a “How Might We?” question:

How might we iterate our client base and our product so that we can find a better fit with and more effectively serve the needs of the right client with the best solution for their needs?”

Again, the goal isn’t to be too perfect here at this stage.

We’re just looking to frame a “good enough” “How Might We?” question to unleash two powerful forces:

  • Empathy by working backwards from real client problems
  • Creativity to design a different future

#2: Collaboratively Design Strategic Choices

In order to start addressing our opportunity, we’ll need to work together to design and choose better sets of strategic choices.

Design new sets of strategic possibilities

With our “How Might We?” question front and center, the cross-functional strategy team can now start stepping through the Strategy Choice Cascade to design 2–3 different sets of strategic choices.

The goal at this point is not to limit our thinking, but focus on designing diverging sets of choices that can address the opportunity framed by our “How Might We?” question from different perspectives.

Identify Barriers

As we identify sets of strategic choices, we’ll need to ask the most important question in strategy to identify potential barriers to each set:

“What Would Have to be True?”

What would have to be true about:

  • Customers
  • Company
  • Competition

For these sets of choices to be viable?

At this stage, we’re making the most of our cross-functional strategy core team’s experience and expertise to identify any insurmountable obstacles that could render an entire set of strategic choices invalid.

Prototyping to Test

The best way to find out is to rapidly prototype to make our ideas “tangible” so we can test the assumptions underlying each set of choices, using prototyping to:

  • Build to Think: Use prototypes to clarify our thinking. When we say combination hardware-software solution, what can we rapidly mock up to see what that might look like?
  • Build to Learn: Are our assumptions potentially valuable and viable? Until we can put prototypes in front of our customers to see how they might respond, we’ll have no way of knowing.

We can also use our existing strategy we reverse-engineered back in in step #1 and look at it on a level playing field, alongside our other sets of choices.

Once we get a sense which sets of choices have a greater chance of success, it’s now time to start taking our promising strategy from idea to action.

#3: Map Our People and Potential

At this point, many teams plan and plow ahead and start building.

What we’re missing is understanding the role our broader organization takes in making or breaking our strategy.

If we don’t make real efforts to build internal support at this stage, we can end up with indifference, or worse, resistance.

To this end, we’ll need to map the full landscape of people across our organization (“Stakeholders”) who’ll be instrumental in making our strategy to be successful, including:

  • Sponsors
  • Senior Leadership
  • Technical or Subject Matter Experts (“SMEs”)

At this stage, our goal will be to take our prototypes we’ve iterated during our strategy design internally and with clients, and use them so we can now:

  • Build to Communicate — Share our evolving prototypes with stakeholders so they can understand our strategic choices and what we’re trying to accomplish.

Finally! Let’s Plan!

Now that we know what problem we’re trying to solve, for whom, a set of choices that can address that problem, and brought the organization along, it’s time to plan our:

  • Capabilities — Our key activities, the things we do
  • Systems — The infrastructure that supports and continuously improves our capabilities

By laying the right foundation of client-centricity, creativity, and strategy to design and test a set of choices, we now stand a far greater chance of successful delivery.

The key to planning at the right time

While we’ve delayed planning longer than we’re used to, it should be clear that planning is absolutely essential to successfully bring our strategy to life.

By starting from client-centricity and creativity, we’ve avoided the fundamental mistakes most business people make in starting by thinking internally, and analytically.

This internal focus jumps from financial and user-base growth “Strategic Objectives” right into a random list of features they assume will deliver against those goals.

When we start by intricately planning heavyweight “Initiatives,” the leap is simply too great, both for our company to build the right things in the right way, directly connected to real customer needs.

The Ivory Tower

It’s the classic example of the “ivory tower” syndrome, where disconnected leadership thinks they know better what their users should have.

This isn’t to fault the product delivery teams — they design and build as best they can.

But without a core of client-centricity and strategy, it would be almost impossible to deliver something that will solve client unmet needs in ways that produce business value.

As I’ve seen throughout my career, without client-centricity and strategy, so many talented, hard-working people continue to put effort into building products beautifully that probably should never have been built at all.

Takeaways & TL;dr:

As with many things, success comes from keeping two potentially opposing viewpoints in mind at the same time, and using the right one at the right time.

It’s not that planning is bad, or that we never want to plan — It’s that we want to start from the right foundation.

Strategy allows us to work backwards from the right problems worth solving, and address them by innovating in the service of great client experiences.

When we:

#1: Uncover the Client Problem

#2: Collaboratively Design Strategic Choices

#3: Map Our People and Potential

We lay the foundation for creating a meaningful plan that solves problems truly worth solving.


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