CIOs' Hardest Problem Isn't AI. It's Leading People.
Heller Search Associates, Wednesday, September 30th, 2026
Executive coach Jessica Kral finds tech leaders' biggest AI-era challenge is guiding people through uncertainty.
Former CIO and executive coach Jessica Kral interviewed seven technology C-suite leaders for the Heller Search blog and found that, while AI was the catalyst, their deepest challenge was leading teams and partners through rapid change and uncertainty.
Leaders describe an unprecedented pace and an expectation of fast outcomes rather than proofs of concept, which pushes even capable executives back into old habits.
Those who thrive stay honest about what they don't know, translate ambiguity into direction and keep people at the center.