How to Sell Innovation Strategies to Executives: Prepare for Debate and Seek Decision

One CIO shared this feedback with me after reading my book, Digital Trailblazer. “Isaac, I wish you had written more about your experiences with the Board and the strategic leadership team (SLT),” she said.

Even seasoned CIOs, CTOs, and CDOs want advice on navigating their CXO/SLT and CXO/Board responsibilities because even with some experience, it never feels like you’ve mastered developing relationships that lead to faster and easier decisions. For aspiring digital transformation leaders, your first experiences with the SLT and Board can be nerve-racking.

Sell Innovation to C-Suite with Isaac Sacolic

I tell one of my fun stories interacting with the Board in Chapter 1 of Digital Trailblazer, where I have to answer a Director’s question, “What’s a cookie?” In Chapter 9, I share stories and insights on selling innovation to the C-Suite.  

Digital Trailblazer Community

And if you don’t know already, I recorded ten supplementary videos for Digital Trailblazers, and they’re available for free by signing up for the Digital Trailblazer Community. Below is the video for Chapter 9, where I share several key insights:

  • Your skiing in powder. Keep your weight on your heels and ski tips up because if you dig in too quickly, you’ll end up face-planting into the snow.
  • Recognize you’re a poker player with imperfect information, but you can’t wait for all the cards to fall before placing some bets. 
  • I take lots of walks. Acknowledge and manage the stress that comes from leadership roles.
  • Create collegial debates and conflicts but avoid a competitive culture.
  • Come out of executive meetings with clear decisions.

I hope you’ll watch the video where I detail these recommendations and continue reading below for one more key recommendation.

Prepare for the dialog, not just the presentation

Here’s the new insight for you.

I get many calls from CIOs to review their Board and SLT presentations. By the time I see them, the data, visuals, and language look fairly polished, and most of the technojargon is either gone or explained for an exec-level audience. Many have done a decent job of closing their presentation with a specific ask of the committee and outlining what decisions are needed.

“How many executives have you spoken to before creating this deck,” is usually my first question. The answer I usually get is that there wasn’t enough time to conduct these conversations. That’s wrong answer number one. Preparing for these presentations is a key CXO responsibility, and having regular discussions with executives is key to being prepared.

If the presentation is to the Board, most CXOs admit that they don’t have relationships with Directors to have pre-meeting calls and some CEOs require being involved in all Board-level discussions. The next best option is to do your homework, research the executives, and learn as much about their backgrounds, goals, and biases as possible.

The second question I ask is, how are you preparing for the dialog that should come before, during, and after your presentation? Will you create collegial conflict that leads to a decision, or will the presentation end with an unsatisfying and inconclusive dialog?

Trust me, I’ve led many exec-level discussions that only achieved a dialog, and it’s not always possible to have one sitdown that leads to clear decision-making. But I do come prepared to facilitate the dialog.

StarCIO Digital Trailblazer Advisory

So that’s my advice: Prepare for the dialog at least 2-3x more than how you prepare for the presentation. What questions are you likely to be asked? What darts will detractors throw your way, and how will you dodge a bullet? Are you prepared to address the elephant in the room?   

None of this is easy. I’m here to help.

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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,, 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.