The Pessimism Problem

This post originally appeared on the Gartner Blog Network. This version may have minor updates and edits.

Last week, I discussed how an organization’s POV on technology (Strategic or Supportive) is a big indicator of both satisfaction and success (with technology).  This week we’ll look at things from a slightly different view, pessimism.

Late last year (pre-COVID obviously) we were fielding a survey focused on customer experience and subscription renewal decisions.  The initial results were surprising to us and we felt that we may have conditioned those taking the survey to respond a certain way in one part. So we decided to try to shock them out of it with a statement we thought most people would disagree with.

That statement was “We regret nearly every purchase we make after the subscription agreement is finalized.” Respondents were given a 7 point scale with 1 being strongly disagree and 7 being strongly agree.

Our attempt to shock the respondents ended up shocking, well actually, surprising us–at least initially.  54% of the respondents indicated some level of agreement with the statement.

When we dove deeper into the analysis though, the data held up.  We discovered that the group we call pessimists were:

• Much more likely to downgrade or cancel subscription agreements
• Less likely (and this was statistically significant) to add additional seats or functionality
• and, no surprise here, much more likely to renew agreements when they are not satisfied (because they may never be satisfied)

There were (statistically significant) more pessimists with CEO, CFO, and CIO titles –executives may not be happy–and less within Corporate IT roles. We also saw more pessimists working in large organizations and less in mid-size (very large organizations were pretty balanced).

And finally, pessimists are more likely to view technology less strategically than others (connecting to last week).

As we dove into this, we began to hypothesize on the root causes of pessimism.  We believe there is room for blame on both sides of the table:

Buying Organizations

• Ineffective buying processes
• Organizational politics
• Unrealistic expectations, often driven by failing to commit the resources necessary for success

Selling Organizations

• Overpromising
• Obscuring the work required to be successful
• Push for deals on vendor vs. buyer timelines

You can all probably think of more.  But fundamentally, this is a problem we need to acknowledge.  There is a long, well document history of technology failures.  Many are conditioned to expect a bad experience. And when your mindset is pessimistic, it can be hard to crawl out of the morass of misery.

And, when times are tight, pessimism probably makes things even tighter.

I believe (well, hope might be a better word) that we can fight pessimism. But to do so requires work on both sides–since both sides share the blame.

Buying Organizations

• Apply decision making best practices to buying efforts
• Provide leadership training on the high cost of minimizing team efforts with drop-in decision making
• Seek information from your vendors and references about what it takes to succeed

Selling Organizations

• Stop overpromising
• Conduct pre-mortems and scenario planning exercises with customers to reveal keys to success (and things to avoid)
• Connect the need for the deal to the timeline to achieve value

Ultimately, it comes down to confidence.  Confidence is a mindset. You can rebuild confidence, but it takes effort.  More on confidence to come later.

Rampant pessimism is a critical issue for the technology industry.  I think we all know it exists–almost like a dirty little secret.  It’s time to acknowledge it and address it–collectively.