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Project Confidence: Your Strategic Initiative’s ‘Moment of Truth’

The Moment of Truth

There is a ‘moment of truth’ for any strategic initiative.  It normally happens after people have had an opportunity to envision project success and contribute their ideas or suggestions. This truth filled moment takes the form of a simple question1:

How would you rate the level of confidence (today) in this initiative? 

The answer is provided by ticking on a 10-point scale– where 1 is ‘not confident at all’ and 10 is ‘extremely confident’.  

It is called the ‘moment of truth’ because it is a grounding moment – a reality check – when ‘up in the air’ ideas and plans are brought down to earth.

It is easy to get carried away with enthusiasm in discussing an important initiative and what it can or should achieve.  But ask this simple question and reality is brought into focus

Those who may have been enthusiastically talking up the project just a few minutes ago often end up putting confidence at 5 or 6 out of 10. In so doing, their realism can be even more powerful than their enthusiasm in illuminating what needs to happen next.

Sentiment or 6th Sense?

Executives close to a project often have a 6th sense when it comes to the success of a strategic initiative. It may be an uneasy feeling or a nagging doubt rather than a systematic analysis of project risks, yet it absolutely needs to be listened to. 

If the confidence question is asked of the right people – that includes stakeholders (customers, sponsors, etc.) then that provides rich qualitative data regarding the state of an initiative as seen by those who matter. 

Now an executive may say: ‘Here is the Gantt Chart and it shows we are well on track for success. Isn’t that what really matters?’  Well, maybe but it is the project’s stakeholders who have the last say.  Perhaps they are unaware of the great progress that is being made, or perhaps delivering against the project plan won’t be enough to satisfy them.  Either way, the confidence question can really help in managing the stakeholder engagement process.

The primary goal is not to maximize confidence or to dispel any doubts. It is to generate a new awareness and dialogue on the success of the strategic initiative.  Ultimately this has the potential to result in a stronger project as well as a more resolute and cohesive project team/community.

How Much Confidence Do You Really Need?

What level of confidence does an initiative or project need to ensure its success?  Our data points to 75% plus as a high level of confidence with respect to an ambitious strategic initiative. Some might say: Shouldn’t it be 80 or 90%?  However, keep in mind: 

  • It is not just the leader’s confidence that we are talking about2.  The test is: does the broader project community (executive sponsors, stakeholders,  suppliers, etc.) put confidence at 75% plus.
  • We are talking about an ambitious Strategic initiative. A higher level of certainty may not be possible if you are pushing the boundaries.  In respect of business unusual doubt can be a good thing as leaders are advised to ‘trade certainty for curiosity’.

What our data clearly shows is that this 75% plus level is not the norm for most strategic initiatives. However, the number is only the starting point for a much more interesting conversation.

Interestingly, our data suggests that agile teams tend to be more confident about their Strategic initiatives. A factor here is that they feel more in control – able to adjust and adapt to challenges as they arise. Something similar applies to dedicated project teams that enjoy higher levels of autonomy. Confidence then may have as much to do with what is happening on a project team as it does with the realities of a project itself.

Too Much or Too Little Confidence?

You need confidence but you want to avoid over-confidence. People have to believe that their initiatives can succeed, if they are to be motivated and effective in their work.  However, over-confidence can leave people vulnerable and unprepared in the face of unexpected challenges or set-backs. 

The gap between strategy and execution is often the gap between confidence and ambition. However, for an organization to be continually pushing forward, ambition must sometimes outstrip confidence.  The danger is that if confidence falls too far behind ambition, sustained progress is called into question. 

It is easy to maintain high levels of confidence regarding every day (or business as usual) initiatives with modest goals and predictable outcomes. However, when it comes to strategic initiatives aimed at shaping the future of the organization (or even its industry) the level of risk and uncertainty inevitably goes up. Take for example, the implementation of new processes or systems that have not been tried within the organization before and don’t just depend on new technology but also changes in behaviour as well as a range of factors in the external environment.

A high level of confidence could suggest that an initiative is not ambitious or innovative enough. In moving beyond ‘business as usual’, certainty must give way to curiosity and innovation. In complex and fast changing environments people must be able to act in the face of uncertainty

If an initiative is too ambitious then confidence may be low. But if confidence is high, then maybe the project is not ambitious enough. While strategy is fueled by ambition, the sobering reality is that: Most transformation projects fail. Most change initiatives struggle, and most strategies under-perform. This is what happens when the ambition of the strategy gets out of step with confidence in its execution

Need to Boost Confidence?

At what point does confidence fall below a workable level?  For example, is there a level below which hopelessness creeps in and a wholesale re-think of the initiative becomes necessary?  Well, a 5 out of 10 on the confidence scale might be interpreted as giving the project a 50% chance of success – the equivalent of a coin toss!  Anything below that (e.g. a 3 or 4) might be interpreted as suggesting that failure is more likely than success.   

Some projects may suffer from a crisis of confidence.  Whether justified or not, this could manifest itself in:

  • A timid and overly cautious approach to execution
  • People feeling overwhelmed or out of their depth
  • A lack of motivation or a sense of helplessness
  • A reluctance to take risks and to innovate
  • An inability to act in the face of uncertainty or paralyzing self-doubt
  • People standing on the side-lines, slow to commit to an initiative or take ownership
  • Stakeholder disengagement or disillusionment as they mistake lack of confidence for lack of commitment
  • Protective behaviours – where people play politics, pass the buck or look for cover.

Can you identify any of the above in respect of your own strategic initiative? 

Where confidence is shaky putting a number on it really helps.  For example, where confidence is at 5 the conversation naturally leads to what it would take to get to 6, 7 or even 8. That may involve taking concrete steps such as:

  • Applying greater project rigor including:
    • Risk Management
    • Stakeholder Communication
    • Work plan & Timeline
    • More and better project reviews
    • Revisit assumptions & dependencies
  • Validating the goals set:
    • Use the results chain (look at results under 5 headings)
    • Stress test the results
    • Break results down into smaller steps
    • Adjust the timeline
  • Gathering external validation / proof point
  • Focusing attention on execution – apply project rigor
  • Bolstering resources
  • Supporting & building the team responsible for delivery
  • Improving viability & control (incl. the sharing of information).

It may also involve more symbolic efforts, such as:

  • Getting senior management to demonstrate its interest in the project
  • Communicating what is happening on the project via a project webpage or email newsletter
  • Branding the initiative

There are almost 20 items listed in the bullet points above.  Here is a good place to pause for a moment and to reflect on which of these might be of value to your strategic initiative at this time.

The feeling of making progress is a powerful motivator for a team.  When a team feels like it is not moving forward or cannot succeed it is denied this self-propelling force.  Therefore, managing the narrative that develops around a project is important.  Is it a narrative of confidence and ambition? Or is it a narrative of setbacks, politics, lack of resources and strife?  Confidence around a strategic initiative may be as much about mindset as it is about project milestones or anything else.

Worried About Over-Confidence?

Boosting the level of confidence is not always the aim.  Indeed, there may be times when confidence is too high.  For example: Buoyed by past success an organization may feel that it has the ‘Midas Touch’ (where everything turns to gold). Such over-confidence could:

  • Result in over optimism regarding what can be achieved and by when
  • Lead to recklessness and excessive risk taking
  • Make a project blind to risks and obstacles
  • Prevent people from learning from mistakes or set-backs or even listening to feedback or suggestions
  • Leave a project’s leaders vulnerable to groupthink and resistant to external information.

Do you notice any of the above within your organization or team?  If yes, your strategic initiative could be vulnerable to over-confidence and groupthink (as examined next).

Why Your Spectacles are Probably Rose-Tinted

There are a number of reasons why you may be prone to over-confidence with respect to your strategic initiatives and critical projects.

Why you may be seeing your 
strategic initiative through Rose-tinted Glasses

These 4 factors add to the importance of your project’s ‘moments of truth’:

The Perils of Groupthink – Group think often manifests itself as overconfidence.  That is where people stop thinking for themselves and conform to the opinions and behaviours of the group and its most dominant / powerful members.  This can result in an artificial consensus and a project team ‘living in its own bubble’ – immune to external information that challenges its own beliefs. Ironically, experts can be particularly prone to this form of bias. The good news however is that the conversation about confidence can illuminate and tackle the risk of groupthink (as we examine under the heading ‘Talking About Confidence’ below).

Planning Fallacy – Psychologists tell us that there is an innate tendency to over-estimate how much can be achieved and how quickly.  This is called the ‘planning fallacy’, and it happens when we are closely involved in any strategic initiative3. Pause for a moment to consisder: Is there a history of forecast accuracy in respect of projects and initiatives? Has a sensitivity analysis been done on projections?

A Bias towards Optimism Scientists tell us that up to 80% of the population have an in-built optimism bias4. The prevalence of optimism suggests that it must serve some evolutionary purpose, however in the world of business we are warned that ‘hope is not a strategy’5. Excessive optimism may indeed be dangerous. Pause to consider: Does your organization Is there a tendency towards ‘glass half-full’ thinking, where hyping-up projects is encouraged and ‘negative talk’ discouraged?

Over-simplification – Our innate tendency to over-simplify complex problems leaves us vulnerable to over-confidence. Take for example implementing a CRM system. From an IT point of view that may be a technically demanding and even complicated project. However, if the objective of the initiative is to deliver a world-class customer experience that is complex – its success will require many parts of the organization working together (e.g. sales, service, marketing, compliance, finance, etc.) and will likely require not just changes in process, but in organizational behaviour and culture too. We will explore the issue of complexity in more detail next.

Our data suggests that these 4 risks of overconfidence are at their most when there is high levels of pressure or urgency surrounding an initiative.  That is no surprise, as it follows a pattern highlighted by psychologists and behavioural economists.  Deliberate steps are required to minimize the risk of bias and error.  That includes slowing down, employing more project management rigor and engaging more diverse viewpoints in the process.

Confidence V’s Complexity

If there are high levels of confidence ask: Could we be oversimplifying things?  Before you answer pause to reflect on the factors that make a strategic initiative complex and therefore more difficult to manage.

Most strategic initiatives have a high level of complexity. They have many moving parts and defy the quick fix or silver bullet.  They are difficult to manage or predict and cannot be solved by traditional linear approaches. The problem is that when initiatives are simplified that is exactly what happens – problems are handed over to one or a few experts who break them down into the component parts and work on them in isolation and applying technical solutions when more is needed.

Complex projects require engaging multiple actors and multiple perspectives, working on the whole rather than the parts and adaptive (requiring a change of thinking or behaviour) as well as technical solutions. They demand greater creativity and innovation, as well as curiosity and experimentation. The approach must be an agile or iterative one, where there is fast learning and continuous feedback.

Our data suggests that the risk of oversimplification is greatest where an initiative represents a solo-run by one department or function.  Engaging with complexity requires breaking down silos and effective cross-functional collaboration.

Talking About Confidence

When it comes to confidence the number matters less than the conversation. It is an opportunity for a ‘strategic conversation’ – the type of conversation that while important doesn’t happen in the normal everyday interactions of a team. If these conversations were happening a lot fewer strategic initiatives would struggle.  It is not easy however. 

Can your people discuss the performance and potential of a strategic initiative openly and honestly?  Will the conversation confront the reality of challenges and obstacles, without leaving people paralyzed and despondent?  Well, watch what happens when the confidence question is asked. For example:

  • Will most people put their confidence at a high level (e.g. 7, 8 or 9) raising the prospect of groupthink?
  • Will somebody who sees hidden risks be prepared to diverge from the group and put confidence low (e.g. 4)? 
  • Will those who have high confidence be prepared to listen to those who have doubts?  Will hidden risks be identified?  Will the team be able to balance tension and cohesion?  

Behind so many surprise set-back is a silent whisper of warning. It is when people who put confidence at 3 or 4 chose (often feeling that they had no choice) to stay quiet.  A key factor is psychological safety (the ability of people to say what they are thinking without fear of marginalization or retribution).  This safety is essential to enable the required level of respectful challenge that enables peak performance.

Nothing demonstrates the confidence of the leader more than their willingness to listen to people talk about their hopes and concerns. Yes, leaders may fear that the conversation around confidence will spiral into negativity, but that is perhaps an outdated view.  Today, we know that talking about fears and obstacles can rally a team as powerfully as talking about hopes and aspirations.  Moreover, it builds resilience and determination.

Talking about confidence doesn’t change the reality of a project.  For example, if the conversation is avoided that does not mean that any of the obstacles or impediments will disappear – indeed the opposite is true. However, it is better that people can express their concerns in the open where they can be dealt with rather, than in whispered hallway conversations.

Talking about confidence levels is positive not negative, regardless of what it reveals. Moreover, it is a key element of effective risk management. For example will the conversation:

  • Identify potential obstacles or barriers that are not listed in the table of risks?
  • Suggest that the probability attached to a particular risk or the approach to its mitigation needs to be updated?

  1. Note the wording of the question is deliberately vague. For example, it does not say ‘what is your level of confidence?’, but asks ‘what is the level of confidence?’. It does not specify confidence in any particular aspect of the initiative (e.g. confidence in how it is being managed or confidence in its success). It asks about confidence today – accepting that it is likely to change over time. The team member or stakeholder can answer the question any way they want based on the level of openness that is possible (e.g. they may choose to answer regarding stakeholder confidence, rather than their own). The question is a kin to a ‘fishing exercise’ thereby leading to a more insightful conversation []
  2. Our data suggests that leaders tend to be more optimistic about project outcomes – typically being up to 20% ahead of their teams.   So it is the level of confidence within among the project team and the broader project community (executive sponsors, stakeholders,  suppliers, etc. []
  3. Daniel Kahneman, ‘Thinking Fast and Slow’, Farrar, Straus and Giroux, 2013 []
  4. Tali Sharot, The Optimism Bias: A Tour of the Irrationally Positive Brain (Pantheon 2011) or watch a short video of the author Tali Sharot on TED []
  5. As Rick Page warned in his book ‘Hope is not a Strategy’, McGraw-Hill Education, 2003 []

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