Any advice for a new IT leader/CIO looking to ID blind spots about their organization?

Building solid relationships is the key for me and having a curious not controlled approach will reveal so much more. Blind spots aren’t just hidden they are, in my experience often protected by well-meaning teams who think they’re shielding you from noise. 

Asking questions that make people feel safe to share the messy stuff. “What’s the one thing we keep doing that makes no sense or nobody enjoys ?” is a great icebreaker.

Listen to the quiet corners. The loudest voices in the room are often not the most insightful. Find the people who do not speak up in meetings and ask them what’s good, bad and broken. You’ll be amazed what surfaces when you give space to the introverts and the sceptics.

Shadow your own organisation. Pretend you are a new recruit. Try onboarding, submitting a ticket, requesting access. If it’s painful for you, it’s probably painful for everyone.

Lastly embracing the awkward and difficult. The best insights come from uncomfortable truths. If someone says, “We’ve always done it this way,” that’s your cue to dig deeper. Smile, nod, and then ask the follow on questions.

My advice is be empathetic and you gain more. 

Active communciation - which means asking a lot of questions, and then listening to the answers. You don't need to try and solve the problems you hear at that moment, you just need to be aware of them.

Let them do most of the talking as well/ 

Absolutely — when I stepped into a new leadership role, my best move was listening before acting. I started by shadowing frontline teams, reviewing incident logs and ticket trends, and mapping technical debt against strategic initiatives. This helped me uncover blind spots and align IT priorities with real operational needs.

Great question, I'll look forward to reading any additional responses. My suggestion is to; 1). Focus on building relationships with your counterparts, fellow directors etc, and interview them or their leadership teams, 2). Create a survey that you can send out broadly to gather direct feedback and use this as a baseline to measure improvement, 3). Talk to the COO and CFO, what are they hearing from a leadership and financial perspective about IT? 4). Last, if you have a strategic plan you've inherited make sure it aligns with the organizations goals and needs. If you don't have one that's a perfect place to start having conversations as well. Good luck!