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.
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
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
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
- 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
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
“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.
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
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.