Your BIG BET is going great. Until suddenly…it’s not.

John Rossman

Pressure Test Your BIG BET Strategies

Bad news isn’t wine. It doesn’t improve with age — Colin Powell

I hope all your innovations, strategies, technology platform programs, digital transformations, AI initiatives, operating model transitions, product launches and marketing initiatives are going GREAT. I really do.

These are your BIG BET initiatives.

But… experience and data says the vast majority, 70% to 84%, of all major initiatives, regardless of company size, fail.

How do you really know what the situation is for your BIG BET? Are you “hoping” they are going well? Do you really know? Can you afford to be wrong?

You might need to pressure test the situation and discover the facts that are below the water line of your BIG BET.

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Let’s look forward to envision your biggest nightmare relative to your BIG BET. Imagine the BIG BET initiative doesn’t go well (like the vast majority). Off schedule, off budget, rejected by users and saddled with team moral issues and infighting. The BIG BET is not delivering the financial or operational benefits which formed the business case. It’s a FAILURE. What’s worse…you’re the “owner” of this FAILURE. Yikes!

You’re asked by the board or CEO — “what did YOU do to avoid this disaster?” You could respond with, “I was told everything was fine. The status reports were green. We thought it was going well enough. We held executive updates and frequent status meetings. I did everything I was supposed to do!” And that is true.

BUT… is that an acceptable answer? It’s the recipe that leads to 84% BIG BET failure rates. Its the recipe for not getting to be the leader on the next BIG BET, or worse…

This was the situation with a recent client. Everything on the status reports and board updates indicated progress was “on track.” Mostly “green” checkmarks, a few “yellow” indicators. There was some discussion of challenges and slippages, but “we’ve got this.” Confidence was in the air.

Everything was fine…

Until suddenly…

They weren’t.

Big Bets Fail — But I’m Sure Yours Will Be Different

Every point of research and experience points to likely failure — if failure is defined as materially over budget, significantly behind schedule, and most important, poor adoption by not delighting customers and business users, creating a lack of ROI for the investment.

Seventy percent of transformations fail. Contributing factors include insufficiently high aspirations, a lack of engagement within the organization, and insufficient investment in building capabilities across the organization to sustain the change. — McKinsey Consulting

Forbes assessed the risk of failure in digital transformation to be 84%. According to McKinsey, BCG, KPMG and Bain & Company, the risk of failure falls somewhere between 70% and 95%.1

Don’t Trust — Trust But Verify

The best business leaders have a keen sense for risk and disconnects, take early action on that sense, and use a wide range of tools and techniques to pressure test BIG BET initiatives.

The successful change agent systematically and continually probes in a myriad of manners. This is “pressure testing” — pushing, testing and confirming to make sure nothing starts leaking under pressure.

Through this pressure testing, leaders set a tone of “management by walking around,” not relying on just reports and proxies. Where facts on the ground don’t match the reports, they trust the ground facts and use this truth to strengthen the reporting system.

Here’s your checklist for pressure testing a BIG BET initiative.

Trust, but verify [Russian proverb] The phrase became internationally known in English after Suzanne Massie, an American scholar, taught it to Ronald Reagan, then President of the United States, the latter of whom used it on several occasions in the context of nuclear disarmament discussions with the Soviet Union.2

How to Pressure Test a BIG BET Initiative

Here’s a starter list of topics, questions, and areas to probe:

  • Mission:  Is there a firm, simple and testable definition of the defined outcomes? McKinsey Consulting states that “insufficiently high aspirations” is a major contributing factor.3 Creating a repeatable, clear and high-aspiration is the driver to clear decision making, scope control, launch & iterate, and maintaining business involvement (not letting the big-bet become primarily a technology project).
    This single factor, an orientation to “outcomes”, is the root cause and direct fix to many situations. This orientation permeates through much of this pressure-test checklist.
  • Project approach/methodology:  Does the approach match the situation? Does the approach help minimize risks? Is an agile, prototype, “test & learn” mindset used to an appropriate extent?
  • Risk-Forward Hypothesis Testing: Are key outcome risks — adoption, impact, feasibility, technical, business case, etc. — identified, ranked and cleverly tested as early in the project as feasible?
  • Plan: Is there a realistic, written, current schedule and milestones? Does this plan reflect the aforementioned “mission”, prototype, risk-forward hypothesis testing?
  • Team: Are people & skill requirements estimated? Is the team comprised primarily of dedicated members? Do we have the right expectations with our team? What are the “key person” risks in the organization?
  • Project hygiene & governance: Do we run a clean project – weekly written problem & risk featured status reports (& discussions)? Adhere to best practices for methodology? Steering committee interaction?
  • Scope Control: Is “project & scope change management” such as features, schedule, estimates, resources, etc., deliberated and documented and appropriate for the mission and risk mitigation?
  • Decision-making rights: Are decision-making rights clear and followed? Do we allow the “easy things” to become the “hard things” in the BIG BET? Is consensus the ruling law or is brave leadership put in a position to actually lead? It was the company president’s brave leadership at a recent client which allowed for an honest assessment and decisive action to nimbly change the trajectory of a technology and operating model transformation.
  • User & Business Involvement: Are user and business involvement and decision-making appropriate for the mission?
  • Budget & Controls: Is the budget realistic, documented, and current? Is there appropriate finance team/expertise and internal audit participation?
  • Key Partner Strategy: What was the logic and process for key partner selection? How are partner relationships? Is there a “one-team” mentality or a “vendor” mindset?
  • Contracts: Are all key contracts current and administered? Are partner relations attended to and valued as essential partners? The best business leaders have a keen sense for risk and disconnects, take early action on that sense, and use a wide range of tools and techniques to pressure test BIG BET initiatives.
  • Forward-looking operations, organization, and scaling: Are clear operational requirements, SLA, and support plans defined? Are future roadmaps understood? Is there a scaling forecast and plan? Is there a realistic budget?
  • Business Case & ROI: Is there a qualitative and quantitative business case with clear assumptions, drivers, and connections to how we manage the project?
  • Current Status & History: Is there a clear, honest, “issue first” understanding of the current situation? What does the history of this project (and other projects) tell us about the forecast and needs of the situation?
  • Dependencies & Assumptions: What are the dependencies and assumptions (explicit and implicit) of the initiative? Can we decrease/eliminate/hedge the dependencies?
  • Skip interviews, informal discussions, and unscripted moments: Create more opportunities to talk to the “boots on the ground.” You’ll add an entirely new set of sensors, triangulation across silos, and pick up on moral and people risks.

Technology & Environment — Even Further Scrutiny is Required

  • Selection of technology and partners:  Are the tools and solutions appropriate for features, operations, ownership, and scaling?
  • Environments: Is there an appropriate dev/test/integration/production path and controls documented & managed?
  • Test Approach: Is there a thorough integration and user test plan? Are regression testing, test suites, test automation, etc., in place? Are specialized QA skills dedicated to the team & operate with the right independence from the core dev teams?
  • Data Conversion: Is there a realistic data conversion plan?
  • Security & Cyber Risks: Has a “secure-by-design” and appropriate expertise been involved?
  • Migration and Adoption Plan & Goals: Is there a written and logical migration plan and understanding of how “adoption” will happen? The adoption intervention and de-risking adoption is a key risk-forward hypothesis to be tested and often neglected. This tends to be a point of blindness to most transformations.The outcome is not “technology release”. The outcome is “successful and consistent user adoption and benefits realization”.
  • Monitoring and Metrics: Is there a monitoring and metrics plan? Emphasize user adoption, user engagement, key business case drivers PLUS all of the performance, availability and data quality metrics needed.
  • Solution Extensibility, Flexibility, and Business Logic: What type of flexibility and reuse are we architected and planning for? Are building for “point solutions” or an understanding for being able to quickly respond to future needs.

Ask for Proof Points

Most initiatives are governed through their status reports, risk reporting, and budget reviews. This is, by nature, rolled-up information and reporting. Add to your reporting by doing more demos, prototypes, beta testing, early scaling tests, and any other opportunity to see and demonstrate something operating versus just reporting on the progress. Verify using first-hand verification by finding ways to design and schedule more proof points.

Feature the Bad News

And finally, communication execution and style.

Is there a communication plan & messaging expertise? Is communication targeted and appropriate for different stakeholders and needs? An authentic story is always needed and is a key part of strategy and success. This story makes your customers, your users and the business case the hero and explains how your BIG BET gets them to the desired future state.

This is one reason why the “future press release”, when used strategically, helps frame an initiative as a story used through a BIG BET to both define the outcome and remind us of the hero and the outcomes.

Do the status communications get to the “heart of the matter” (versus opaque, complex, and optimistic) and in succinct language? Are the “asks” clear and succinct?

In 35 years of running and participating in hundreds of projects, my number one rule in status communications is “feature the bad news.” This mindset and guideline is counter to how the vast majority of project reports and communications are architected and led.

When we “feature the bad news”, the entire posture of the program and leadership culture changes.

A BIG BET initiative, any digital transformation, or operating model transition is just a collection of issues and risks. Operate from that assumption. When you feature the issues, feature the risks, feature the weaknesses every BIG BET has, we have the opportunity to deal with them. You create a leadership culture of straight talk, humility and execution risk mitigation. This is truth seeking.

Recognize that this should not come at the cost of having a positive or optimistic demeanor or culture. In fact, it’s the combination of positivity, humility and “featuring the issues” which creates positive spirits, team moral, risk mitigation and successful big-bet outcomes. It creates bold and empowered leadership and teams.

When issues and risks are ignored, unrealized, hidden and “optimism” becomes our default position — your BIG BET initiative, & your job, is at the most risk.

Your Homework

You are a strategist, innovator, and change-maker. Your world revolves around planning, running, and launching complex BIG BET initiatives — and having them successfully deliver the envisioned outcomes.

Think through — “is everything actually the way I’m being told it is?” Should I just “trust” what I’m being told? Do we operate with “feature the bad news” bold leadership? Take action and pressure-test your BIG BET.






More from John Rossman…

John Rossman | Leadership Keynote Speaker & Author