Why What and How In Action

Here are two real-life scenarios that show how to surface Why are we trying to do this; What do we do to achieve this; How do we do this with repeatable success?

How often do you hear “we’re too busy to plan” or “we’ve done this before, no need to improve” or “why didn’t they do what I asked them?”

These are common issues. See if you can deduce the root cause of the similar problems in both of these scenarios…

Scenario 1 — Startup Software-as-a-Service Firm

I’ve known many SaaS entrepreneurs with an MVP that believe they have a coherent thesis for building the right product. Their product works okay and now they have to add new functions and support services that some customers say that they want and need.

With that in mind, they begin developing and testing new functionality. Underlying that, they also believe that they must just get sh*t done: “We simply don’t have the luxury to discuss, debate, resolve, and commit to a business strategy expressed in software.”

Most would be wrong.

Agile software development without coherent reasons of the products WHY results in development teams that lack clear, common vision of the product, and individual, expectations.

With strategic objectives and measurable outcomes “that are written down and shared freely, everyone feels more comfortable, and more work gets done”. Without them, team members cannot pull in the same direction.

Writing down the vision and goals (often not done at all) and clearly articulated objectives, key results, and benefits is crucial.

“Only 51 percent of companies, even attempts to develop align goals and among these, only 6 percent regularly revisit them.” — Deloitte Insights

This undoubtedly applies to product development team activities. Just as import are feature backlog and roadmap that is driven by the outcomes of the users (customers) of the tool. Agile User Stories, Features, and Epics should form a strategy map of users’ personal objectives and success metrics.

Strategic objectives (WHAT) that deliver key results (HOW) and benefits (WHY) align customers, products and teams vertically and horizontally.

Scenario 2 — Medium-sized Professional Services Firm

I’ve had a number of successful pro services firm clients that grew organically for several years. This means that they have added clients over the years and adapted how they did things to each client situation without putting too much thought into underlying systems and repeatable processes.

Leadership decided that the firm was well positioned and could grow profitably at a much higher rate.

Leadership also believed that adding more front end new business developers with some content marketing air cover would unlock growth.

They believed that they could simply bolt-on fancy new technology and continue growing their business as usual.

However if they pursued this course of action they would be wrong, and find themselves poorer and stuck with a lot of profit eating overhead.

What was missing? Three things. A growth thesis, a framework for operationalizing that thesis as a system, and consistent implementation processes with accountability.

In other words, planning to succeed rather then hoping not to fail. First steps should have been understanding Why? and then defining What? before doing How?.

So instead of sales being the most visible part of an organization (revenue is king) while having the least transparent process, they could have a sales enablement technology stack automates and surfaces sale success.

So what is the problem?

Did you pick up on the hints?

  1. Lack of asking “Why?” as a first step
  2. Lack of writing it all down during meetings and in notes
  3. Lack of defining and sharing objectives and key results

A good example of writing down What? and Why? before designing How? is a recent article by Alex Osterwalder; “Entrepreneurs, Don’t Build Too Soon

In it he says:

“..the goal is not to start building a limited version of your product or service. The goal is to achieve maximum learning for the least amount of effort.”

Asking the questions, maximizing learning, defining outcomes, solving problems, and finding solutions are a technique. This is a technique that leverages methods that I have honed over time.

Strategy-Driven Everything

I promote Strategy Driven… everything. To me strategy is synonymous with Why which is discovered via strategy maps and business model canvases.

I use those strategic objectives to anchor What is done via value chains, value streams and teams-tools-flows definitions.

Business capability mapping is used to link strategy to the tactics of How things are, or should be, done. Capabilities are defined as simple as possible with enabling templates that make up the people-process-technology components.

I utilize a set of tools I’ve created to capture these important pieces of information. I call it Digital Product Masters.

The Digital Product Model Master (DPMM) framework templates include all of these. The ultimate result is a digital model of an entire business enterprise. Or it is a model of a sliver of organizational activities that can be built on in the future.

DPMM is a right-sized Enterprise Architecture and Business Architecture set of methods. A EA/BA project can be large, but it does not have to be.

A Digital Product Master (DPM) is a living model of the DNA of a business, or of a function within the business. An important outcome

Failure to understand and communicate What and Why results in teams that are not on the same page. Failed product development and marketing technology projects are the outcome.

Fixing that is my mission.

Normally it is; How, What, then maybe Why

Small slivers of the different aspects of client projects are examples of how I use a Digital Product Master (DPM) scaffold to rapidly drive solutions to problems.

The the examples of client scenarios seem to be very different at first glance but I find that there is more in common in project discussions than not.

What is common (and commonly found) is that in order to evolve or scale, business activities need to be organized and communicated within a group.

  • The use of tools needs to be clarified and agreed upon in order to promote common vocabularies and methods of How they do things phase.
  • The data collected and generated during What they do phase needs to be stored and shared via prescribed high level actions by the team members.
  • The need to reinforce Why they are doing things by defining simple strategic objectives and desired outcomes.

To address the goals of both clients scenarios, there is a need to ‘write-stuff-down’ and to apply lightweight Digital Product Master elements starting with tools, teams, and flows.

Tools Teams Flows — ©2017–2018 Asterius Media LLC

By reversing the questions we can quickly get to information needed to develop How. There are several ways to discover and surface the What and in a light-weight manner.

  • Maturity Model Questionnaire
  • Business Model Canvas
  • Value Stream Activities

Here are brief descriptions of how these methods are applied to the example scenarios.

For a Startup SaaS company

Two common software development challenges of moving from a proof of concept to an initial commercial phase are development team effectiveness and siloed product management

Most development teams think they use Agile, Kanban, and Lean. Perhaps they do to some degree, but gauging them against a Software Development Maturity Model can benchmark them against world-class best practices. This does not mean they want or need to become world-class. It does meant that we can identify desirable next-practices to strive for.

I often use a relevant capability maturity model for a quick assessment of a client’s process and practices. In the case of SaaS companies I use an assessment that is a combination of numerous publically available models including Agile Maturity Model (AMM) , The Product Management Maturity Model , The Continuous Delivery Maturity Model , and A Software Maintenance Maturity Model: S3M . I have also added several dimensions around individual and team competencies.

A common next-practice opportunity observed, including this scenario, software product processes were ad hoc and not tied to strategy.

My Digital Product Master (DPM) reference framework for software development is a quick-start guide for improving practices and make the team more effective and efficient. It covers this and other common issues.

A SaaS DPM provides insights and traceability of common daily activities up to stakeholder values and benefits. The Why and the What are often not thought of and not shared transparently to all. So before diving into tool selection, it is imperative to have a high level understanding of What. DPM templates do that.

Strategy Driven Development

The same concept can be applied to software product agile epics and features with a high level understanding of the personal strategic outcomes customer are trying to achieve by using the product.

As said in “Intersection: How Enterprise Design Bridges the Gap between Business, Technology, and People” by Milan Guenther:

“Instead of just differentiating on product features, performance, or abstract notions of quality, they aim at expressing the value an enterprise provides to the people it is related to, in a way that makes it unique just for them.”

The strategy driven development methodology can be applied to the workflow of the products users and to the workflow of product development team. Value chains and value streams are an excellent way to capture both.

Part of next practice development is to document at the highest level what is being done. Sometimes this is called business process analysis or, at a higher level of abstraction, value chain and value stream analysis. It is often seen and laborious and not practical — it does not have to be.

GISTICS Incorporated / Asterius Media LLC

For this client we defined the essential elements of a best practice software product development value stream called Requirement to Deploy.

GISTICS Incorporated / Asterius Media LLC

In particular we chose to concentrate on Software Development Workflow and enabling capability of Product Software Development..

Workflow activities can be defined as a combination of process maps, action plan checklists and logic models.

Logic models not only provide a listing of activity actions but also align them to process output measurables (What) and lagging indicators or objective key outcomes (Why).

This slice of what and why for software development activities informs us of the key actions taken by teams and what tool features are needed for this organizational capability.

These are parts of a more complex set that of the What phase defined by a proper DPM for software development capability.

Process Flow Model Master Framework which Aligns business process map role, actions and flow decisions with resources, activities, effectiveness indicators

In the case of this client project it was important to define information services features for the tools chosen to enable the capabilities. Key activities for a developer include writing software code, previewing code, versioning code and integration code building and testing. By creating a list of these actions, appropriate features of candidate tool(s) can be mapped.

Making Improvements

These along with actions of other team members we were able to quickly identify gaps in tools they were using. To fill this gap three tools were chosen:

  1. Aha Product Management Strategy definition of goals and measurable outcomes that deliver stakeholder value mapped to product features
  2. Visual Studio Team Services Agile User Stories, Epics, and Features with 2-way integration with Aha
  3. Slack Notifications and team collaboration via messaging and chatbots with intergations to Aha and VSTS

The products are loosely coupled to form an extensible and flexible cloud based solution.

The result of this effort is a product management and development team that are using tools in support of specific workflows. Workflows that provide measurable strategic outputs and outcomes.

It results in a product backlog and roadmap that prioritizes work based on specific strategy initiatives. Each user story can be tied to benefits that drive defined stakeholder value. Backlog User Stories can then be compared with each other objectively.

Before choosing from the plethora of tools to use (How), or what feature user story to develop next (What) it is really beneficial to understand precisely Why.

Simple strategy driven approaches to software development and product management reduce complexity and reduces future technical debt.

For a Professional Services firm

It is imperative for B2B firms needing to ramp up their sales activity driving revenue growth to define and codify their process for scalability

My background in marketing communication and technology gives me a deep appreciation for strategy driven… well, everything.

When asked to drive the design of CRM Sales Pipeline Lead Scoring automation, my first question is obviously…

Why Score Leads and Opportunities?

“We are too busy finding and talking to client prospects, I don’t need to use that tool” is a common sales professional’s refrain. Sales and Marketing is too often thought of as not needing structure and process. But the best salespeople have a process which if shared could help others improve.

Unfortunately lessons learned are mostly not shared or taught to others

In “Business Architecture Made Easy — A Journey from Complexity to Simplicity“ Bernard Morris says “lack of shared perspective is a root cause of a business’ inability to address a growing list of challenges”.

To improve common understanding it is useful to survey what is being done and recommend next-practices based on lessons learned by others.

To help determine what practices should be adopted I created a Lifecycle Marketing and Sales Enablement Assessment.

The purpose is to assess current practices against best practices maturity models tailored to my client to identify next best practices to adopt.

The model was derived from a number of sources including; Digital Marketing Capability Maturity , Sales Enablement Maturity Model , and Marketing Technology Maturity Model .

The assessment is a survey with questions like:

  • Do all sales groups have and follow a consistent sales process?
  • Are there clear gates or decision points in the progression of the sales process?
  • Are sales forecast weighted based on opportunity sales stage?
  • Are opportunity forecast close dates driven by timing of critical path events?
  • Are sellers measured by adherence to the sales process?

And that is just in the General category or maturity dimension. There a number of other dimensions including CRM, Sales Process, Sales Collaboration, Messaging, Content, and Digital Marketing.

Ideally the survey is completed by all sales stakeholders. Determining alignment within a group is the first major benefit. The results are diagrammed with heat maps, spider diagrams and bar charts that illustrate gaps of sales capabilities:

What can I do next?

A common sales process next-practice is to define (and write down) sales pipeline stages and sales funnel status diagrams. This helps all stakeholders to start using a common vocabulary and framework for ideas and discussions.

Lead-to-Sale Lifecycle — ©2018 Asterius Media LLC

The next step is to define Why and What (I will refrain from using the bad word — strategy), and write those down. Two powerful and simple ways to do this are Objective and Key Results (OKR) and Balanced Scorecard Strategy Mapping

These tools help enliven a strategy driven business capability with elements from the strategy pyramid.

Element of of strategy and execution working together — ©2016-2017 Asterius Media LLC

In this scenario the Why for sales is simple: Grow High-Value Customer Relationships

The What is a list of desired outcomes or objectives

  • Increase Website Activity
  • Increase Website Exposure
  • Improve Lead Generation
  • Increase Sales Opportunities
  • Increase Sales Volume
  • Increase Sales Cost Effectiveness

For each of these objectives, expected outputs or anticipated outcomes are defined. For example the Objective Improved Lead Generation could have a Key Results Pair:

I want you to notice that what I am proposing is to simply write stuff down that people already think and talk about.

The key habit to adopt is to write it down by filling in templates that capture:

Why: “Generate more leads that convert to opportunities”


What: “Improve Lead Generation”


How: “New Led Generation up 15% MoM” — Quantity ; “% Lead conversions increased 5% MoM” — Quality.

These definitions lead to defining a set of business capabilities. Business capabilities are simply “How” a business does things. Think of them as organizational level skills imbedded in people, process, and/or technology.

Capability describes the organization’s ability to achieve specific outcomes — ©2017-2018 Asterius Media LLC

With an understanding how the sales capability delivers end-to-end value to its customers, partners, and internal stakeholders, we can choose tools and processes for a trained salesforce. These are the necessary components for improving sales enablement via marketing process automation.

Sales enablement tools and services for content marketing and sales funnel pipeline automation have become more available in recent years.

Unfortunately few are used successfully and if they are used the outcomes are not often aligned with business objectives.

Without a definition of What the desired outcome, neither myself nor my client can understand if the process is successful. Without a process of actionable steps, the likelihood repeatable success across a salesforce is low.

In addition, without Why and What definitions, pipeline lead and opportunity scoring is more subjective than objective and rarely written down, shared, and compared with organizational strategy.

Once key results are defined, measurements are chosen and can be defined in a shared data dictionary:

A self check question used in the development of measures is:

Does this inform us of the progress toward or achievement of the objective?

Once Why, What, and How are defined and aligned with measurement, performance dashboards and strategy scorecards can keep everyone up to date on progress.

Produced with InsightVision

My clients near term goal was to define and implement a digital sales funnel pipeline to enhance their lead generation activities and generate new sales revenues.

Before defining sales pipeline and scoring attributes (HOW) it is important to write down the objectives (WHAT) of each stage of a lead gen process and enabling MarTech as well as (WHY) each attribute supports, informs, and aligns strategic outcomes.

Now we have definitions that provide direction and accountability for a MarTech Growth Cloud that enables linking together cloud services automation.

These clients saw dramatic improvement and demonstrate how simple definitions written down can clarify, make transparent, promote and align sales enablement with business strategy


Consistent implementation is way more than just project management. In high-performing organizations, it starts with Company-wide Objectives and Key Results and then subordinate team-specific objectives and key results that also serve as the context for individual objectives and key results.

In this manner, managers can review weekly key results and see with fairly accurate detail what kind of progress that the company is making and what areas are in trouble or lagging behind — and immediate focus for intervention.

DPM scaffolding provide the linkage between capabilities needed, functions performed and desired outcomes defined. DPM models can identify gaps between what is an what will be.

These two scenarios show how initiatives are created to improve capabilities with objectives and key results that become individuals OKRs. OKRs enable goal transparency and alignment, and formalize reflection on how “I” align with the company to deliver.


  • Too often things get done without basic blocking and tackling
  • Even slivers of business activities deserve to be thought through
  • Developing How things get done without understanding What should be done and Why is wasteful
  • Not fitting into greater strategy or goals impedes growth and builds technical debt
  • Thinking through and writing down objectives and key results is a necessary solution
  • Benefit: “things work better when they work together, on purpose