Why Digital Trailblazers Must Be Paranoid In These Four Important Areas

My friends and colleagues know I can be paranoid sometimes, but it’s part of my survival instincts. When you’re driving transformation and responsible for operations, as I was for most of my career, you develop anxieties over what can go wrong, how it will impact your objectives, and whether you’re missing opportunities to address a material risk.

Why Digital Trailblazers Must Be Paranoid In These Four Important Areas

What am I paranoid about? It’s a long list, but I’ve boiled it down to four important areas that impact Digital Trailblazers.

1. We’re transforming too slowly

I’m currently listening to Kara Swisher’s Burn Book, in which she describes how she forecasted the death of the newspaper classified ad business and other aspects of print media. I spent several years of my career at a SaaS company aiming to help newspapers avoid this fate, and the best I can say is that maybe we gave them a few more years to survive and transform. It wasn’t enough.

Today, my keynotes on digital transformation often include a slide showing the 20-year cliff drop in newspaper revenue.

That experience created my top paranoia – are we transforming fast enough? Should we add another initiative or take on more scope? What’s happening in the industry, competitors, startups, regulations, emerging technologies, or other factors that might create new disruptions?

What’s the answer to finding the right transformational velocity?

Continuously challenge yourself to quantify the threats and seek opportunities to accelerate in key areas. I believe most businesses must accelerate their digital transformation initiatives by driving digital practices while delivering business value. Stay focused on what you can control and influence, but don’t burn out the staff by pushing too hard.

2. Unhappy stakeholders becoming vocal detractors

Digital Trailblazer by Isaac Sacolick In Digital Trailblazer, I share the story of walking into a business meeting to demo a new customer-facing product my team was developing. I was paranoid that unhappy stakeholders would disrupt the presentation and attempt a coup over how the product was being developed.

My paranoia instincts were on target. Read Chapter 4 for the full story, which has a happy ending but not without collateral damage.

The issue here is that stakeholders may not tell you right away of their concerns, and they often articulate their preferred solutions rather than the underlying problems. Digital Trailblazers, especially product managers and architects, should cultivate this stakeholder paranoia because when quiet unhappiness turns into vocal undermining, the politics of turning the situation around can be daunting.  

3. Agile teams are stressing over delivery

These are actually two concerns that become a material risk and one that Digital Trailblazers should be paranoid about.

My first concern is that the team is stressed. There’s a thin yellow line separating feeling pressured to stress out and another red line that separates stressed and burned-out people. “You will always be transforming,” I wrote in Digital Trailblazer because new opportunities, technology disruptions, and market changes require organizations to re-evaluate digital strategies frequently. Burned-out teams and people will slow down, stumble on the treadmill, or scarily crash.

My second concern is when agile teams spend too much time on delivery – implying they are not spending enough time on planning or transformation change management. Even if you hit the target scope and timeline of the active release, the next one is delayed because the team likely overcommitted – and was probably pressured to do so – and didn’t invest sufficient time in planning their features and backlog. Worse can be if they aren’t paying attention to customer feedback and operating metrics from their previous releases.   

I’m paranoid over the stress and the lack of balanced priorities – so much so that I developed three courses on StarCIO Agile Planning to help Digital Trailblazers avoid these mistakes.

4. Teams are firefighting too many “high-priority” incidents

Is the latest incident truly a P1 major incident, or is it an impatient stakeholder demanding attention to their problem without considering the business priorities? And if it is a P1, are the right people collaborating to identify and resolve the issue? Are they communicating effectively and making smart, data-driven decisions on root causes and remediations?

All hands on deck all the time is not a healthy strategy.

Escalating low-impacting operational issues to executives that trigger fears and require additional unnecessary communications is a leadership issue.

Chasing white rabbit solutions because the loudest voice on the bridge call proclaimed the root cause without evidence is a major operational problem.

When happening frequently and at scale, the three issues are more than operational issues -they point to a major cultural problem. And it’s really hard to transform when everyone is in firefighting mode.

I’m paranoid over this problem as I’ve seen too many organizations fall victim to firefighting and blameful cultures.

Avoid letting paranoia become debilitating

It’s totally human to have some paranoias, and our ancestors’ survival instincts were tied to paranoia, sensing, and action.

How have I responded to my paranoias?

Driving Digital Practices

I built frameworks, including the StarCIO Center of Excellence Programs, to guide Digital Trailblazers on accelerating digital transformation. StarCIO’s thesis:

  1. More organizations need digital transformation leaders – i.e., Digital Trailblazers – and seek to run more initiatives faster and more efficiently.
  2. Digital Trailblazers must lead self-organizing teams but must also seek developing standards. We have 175+ activities to help organizations develop them in the key Driving Digital competencies.
  3. Edicts and demands can’t drive cultural change – it’s developed bottom-up through practices, empowerment, and leading with empathy. We advise and coach Digital Trailblazers so that they have the confidence to lead larger-scale digital transformation initiatives, and we guide them on these 50 Digital Trailblazer attributes.

There’s a path out of paranoia to confidence. I’m here to help.

Isaac Sacolick
Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.

Coffee with Digital Trailblazers hosted by Isaac Sacolick Digital Trailblazers!  Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld, CIO.com, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.