When Leadership Gets Lonely: Staying Grounded in Unpopular Decisions (Leadership LIVE w/ Chris Pienkowski)

Leaders aren’t hired to keep everyone happy—they’re trusted to do what’s right for the mission, the team, and the long game. In this Leadership LIVE edition of Speak Up. Show Up. Lead., JJ Hardy and guest Chris Pienkowski dig into the real work of leading through pushback: communicating decisions people won’t like, earning trust without people-pleasing, and avoiding the costly trap of not deciding.

What This Episode Covers

• Lonely, not wrong: Why leadership can feel isolating—and how that’s often a sign you’re standing for something.

• Greater good > universal approval: Serving the mission even when parts of the team disagree.

• Explain what you can (and own what you can’t): Building trust when confidentiality limits details.

• Consensus vs. clarity: Gathering ground truth without turning tough calls into a popularity vote.

• Delivery matters: Firm + respectful beats “my way or the highway.”

• Rhythm builds resilience: Regular communication so decisions aren’t surprises.

• The cost of indecision: How avoiding hard conversations drains trust, culture, and performance.

• Your support system: Mentors, peers, and sounding boards to keep you from catastrophizing in your own head.

Field Notes & Pull Quotes

“Your job as a leader is not to make everyone happy. It’s to do what’s right for the organization and the people as a whole.”

“When you’ve built trust, people may not like a decision—but they’ll roll with it because they believe you’re acting in good faith.”

“Input isn’t voting. Gather perspective, then decide.”

“Indecision has a price—paid in credibility, culture, and momentum.”

Practical Playbook

1) Before the Storm: Build the Base

• Define your non-negotiables. Know your values before the pressure hits.

• Cadence beats chaos. Daily stand-ups or quick huddles make change feel expected, not abrupt.

• Relational deposits. Check on people as people. Credibility rises; resistance drops.

2) When the Call Is Unpopular

• Assess: Does this align with our mission, values, and constraints?

• Explain: Share the why you can, acknowledge what you can’t.

• Deliver with respect: Clear, calm, and face-to-face whenever possible.

• No outsourcing the hard parts: Don’t hide behind emails or your boss. Own it.

3) After the Decision

• Hold steady. Don’t whipsaw to please the loudest critics.

• Invite questions, not relitigation. Clarify intent and next steps.

• Debrief privately. With a mentor/peer: What did we learn? What will we do differently?

Rookie Leader Traps to Avoid

• Consensus addiction: Turning every hard choice into a group vote.

• Inbox leadership: Delivering tough news via email to dodge discomfort.

• Delay drift: Waiting “for the perfect time” while culture erodes.

• Tough-guy theater: “My way or the highway” as your only setting. (There are rare times for it—make them rare.)

A Simple Decision Filter

1. Is it aligned with mission and values?

2. Is it informed by ground truth (not just opinions)?

3. Is it communicated clearly and directly?

4. Is it consistent with how we’ve led before?

5. If no one ever knew I made it, would I still be proud of the choice?

If you can answer “yes” to 4–5 of these, make the call.

The Cost of Not Deciding

• Trust: People stop taking you seriously.

• Culture: Standards blur; the team copies your hesitation.

• Performance: Good people carry the slack and burn out.

• You: Anxiety compounds as you replay the conversation you’re avoiding.

Rip the band-aid. The pain is temporary; the cost of waiting isn’t.

Final Thoughts (Chris & JJ)

• Chris: “You’ll never get 100% buy-in on hard calls. Make the decision and have the conversation.”

• JJ: “Nervous means you care. Build your support system, know the cost of not deciding, and do it anyway.”

Next Leadership LIVE

Topic: Leading Through Conflict Without Selling Out
When: Nov 8 @ 0700 (yep, JJ’s birthday—show up!)

Keep Going

• 🎧 Subscribe on Spotify: Speak Up. Show Up. Lead.

• ▶️ Watch on YouTube: Victory Leadership Coaching

• 📘 Read JJ’s book: Speak Up. Show Up. Lead. on Amazon — a ground-up story of grit, growth, and leadership.

• 📅 Work with JJ: Build your plan, your skills, and your culture. Book a virtual coffee