5 ways to manage an IT transformation like an entrepreneur

5 ways to manage an IT transformation like an entrepreneur

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With our IT transformation complete and legacy systems now gone at Matson, we’re shifting our focus to a new mantra: “go on offense.” This inspired us to leverage our transformation and widen the gap between us and our competitors.

One outcome of our transformation is that it has allowed me to also lead a three-year-old startup, Matson Logistics Supply Chain, which focuses on providing cloud-based logistics and supply chains services to mid-sized global enterprises.

Yes, I'm taking on more responsibilities. Sound familiar?

I’m sure it does, given the responsibilities being added to CIOs’ plates these days. In this new "CIO+" role, I’ve come to realize that the entrepreneurial skills needed to succeed in a startup are actually quite similar to those needed to succeed in the IT transformation effort we just completed. Here are a few:

  1. Your idea must be at least mostly right. You can’t go into a transformation effort or a startup with a half-baked concept of where you’re going. Whether it’s an IT makeover or new venture, it needs to be well thought out and stand up to scrutiny.  With each poorly thought through idea, you’ll be less likely to be given another chance.
  2. You need the knowledge to execute.  Merely having a good idea isn’t sufficient.  Whether you’re laying out an IT vision or entering a new market, can you write a good business plan? Can you explain it to the board?  Do you have a clear sense of the mechanics of how you’ll deliver if your idea is approved or funded? In either scenario, be ready to go if you’re given the green light. Be honest. Can you do it?
  3. You need to establish and leverage deep credibility. Traditional companies with established businesses are not pre-disposed to taking risks, so why should they do so with your idea?  It’s easy for an existing culture to become a victim of its own success. So whether you’re competing for scarce capital funds for a new line of business or convincing a board to approve a multi-year IT transformation, stakeholders must believe that you and your ideas are a smart risk. In many ways, they are funding YOU.
  4. You need to be in constant sales mode. In both an IT transformation and a startup, you will be highly engaged in convincing a lot of entrenched, doubting people that your non-traditional approach makes sense. Do you have your elevator pitch and sound bites? In either scenario you have to be very good at anticipating all questions.
  5. You must lead and execute without fear. You’re at an inflection point, and your career will be significantly changed in some way. Let’s face it, most startups don’t go on to become household names, and most IT transformation efforts sputter to a close, often taking the CIO with them. You worked hard to get this far, and you’re taking a risk because you believe it’s right. Be unafraid and unwavering in delivering on your vision, and be at peace with the ultimate outcome, with no regrets.

Remember: the next time you’re thinking about an IT transformation project, think like an entrepreneur and ask yourself:

  • Will this present as a good idea?
  • Is it well vetted?
  • Will it withstand scrutiny and devil’s advocacy?
  • If approved, am I clear on how I’ll deliver?
  • Will people who trust me follow me into battle?
  • Am I ready to bet my career on this idea?

Unless you do, you may end up with a half-finished overpass, littered with hardware and software that doesn’t fulfill its promised value. Not unlike a failed venture with some unrealistic hockey-stick growth that never materialized, you’ll be left standing in front of some disappointed investors trying to explain what went wrong.

Peter Weis has over 15 years of global CIO experience, and is currently VP and CIO of Matson Navigation, a $1.7B, publicly traded, global transportation and logistics company (NYSE: MATX). At Matson, Peter leads a global IT organization that is responsible for strategy, software development, infrastructure, high-availability operations and all levels of IT governance. Peter's leadership track record spans both start-ups and Fortune 500 companies. Most recently he led Matson’s successful multi-year IT transformation that refreshed Matson’s entire applications portfolio, re-built the IT Services organization, implemented a fully virtualized architecture and installed an enterprise-wide IT governance program. This strategy’s success has enabled business growth, lowered costs and eliminated significant technology risks. In 2014, Matson was ranked as the #1 ocean transportation provider in the world, both in overall service and in information technology.

Peter Weis has over 15 years of global CIO experience, and is currently VP and CIO of Matson Navigation, a $2B, publicly traded, global transportation and logistics company (NYSE: MATX). At Matson, Peter leads a global IT organization that is responsible for strategy, software development, infrastructure, high-availability operations and all levels of IT governance.

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