Why Saying “I Don’t Know” Makes You a Stronger Leader
Jose Cruz on trust, feedback that actually lands, and why onboarding decides engagement
The leader who admits what they don’t know gives the whole team permission to do the same, and that’s where the real answers start showing up.
Jose Cruz is a talent development executive with more than 25 years shaping talent, culture, and organizations, from luxury retail floors at Saks Fifth Avenue to global teams today. In this episode of Herding Squirrels, he makes the case that the three hardest words for a leader to say are also the ones that build the most trust. We get into why “would you like my thoughts?” lands better than “can I give you feedback,” why so much training never changes behavior, and how the first 90 days decide whether a new hire stays engaged. If you’re leading a team through AI, remote work, or any change you can’t fully explain yet, this conversation gives you a practical way to say so out loud.
Meet Jose
Jose R. Cruz Jr. is a talent development executive, lifelong learner, and people enthusiast who believes great leadership starts with helping people grow. With more than 25 years of experience shaping talent, culture, and organizations, he brings strategic thinking, heart, and a little personality to everything he does. His philosophy is connect, inspire, elevate. He’s certified in 360 and Hogan assessments, and yes, his family is a LEGO family.
Find Jose online: LinkedIn
Episode Highlights
[00:00:44] The best teaching makes people feel like they already had the answer
[00:02:58] Stop patching weaknesses and build on what you’re great at
[00:07:55] Why a great facilitator isn’t automatically a strategic partner
[00:11:21] The kind COO who couldn’t hold people accountable
[00:12:46] Ask “would you like my thoughts?” instead of offering feedback
[00:16:02] Leadership versus management, and why job descriptions miss the point
[00:24:17] In order to go fast, you have to go slow
[00:27:48] At the heart of every change is fear
Key Insights
Trust unlocks “I don’t know”: People only admit what they don’t know when they trust the person in front of them. Build that relationship first, and the learning follows. (00:01:20)
Drop the word feedback: “Feedback” puts people on guard before you’ve said anything. Asking permission to share what you’ve observed opens the door instead of bracing them for impact. (00:12:46)
Don’t skip the impact: Most people deliver the situation and the behavior, then stop. The impact is the part that actually changes what someone does next. (00:12:00)
Not every problem needs training: If you jump straight to “I’ve got a training for that,” the behavior won’t change and the training fades. Find the root cause first. (00:08:18)
Nice is not the same as accountable: Kindness without accountability gets mistaken for naivety, even by people you’ve worked with for years. Holding the line is part of caring. (00:11:21)
Slow down to speed up: Every time you say “I’ll just do it myself,” the knowledge stays with you and your frustration grows. Teach it right once. (00:24:55)
Onboarding decides engagement: Schedule the first ten meetings for your new hire, hand them the org chart, and stop making them hunt for the benefits number. The first 90 days set the tone. (00:25:56)
Change runs on fear: People fear losing the skills they’ve relied on for years. Name it, say you don’t have every answer, and figure it out together. (00:27:48)
Key Quotes
“People always remember how you made them feel. They might not remember the thing that you did.”
Jose
“Just because you’re a facilitator or a trainer doesn’t mean you’re a strategic partner.”
Jose
“I don’t say, would you like my feedback? Because once you hear the feedback, the hairs on the back of your neck stand up.”
Jose
“When leaders pretend to know everything and their team just knows they don’t, now you’re losing credibility.”
Jose
Resources Mentioned
CliftonStrengths (StrengthsFinder 2.0), Gallup: https://www.gallup.com/cliftonstrengths
Hogan Assessments: https://www.hoganassessments.com
360-degree feedback assessments
Situation-Behavior-Impact (SBI) feedback model, Center for Creative Leadership: https://www.ccl.org
Situational Leadership II, The Ken Blanchard Companies: https://www.kenblanchard.com
The change curve and the “valley of despair”
Jay Redmond, Jose’s longtime mentor in learning and development
Jose on LinkedIn: Jose R. Cruz Jr.
About Herding Squirrels
Herding Squirrels is a podcast about modern teams and change. Each episode uncovers what’s working in leading teams through the lenses of people who’ve been there and lived it. Subscribe wherever you listen, and leave a review if this conversation was useful.
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