How to empower employees to make decisions without you

“You can’t trust without setting the expectations and giving them the guardrail to move within.”

At around 40 employees, Trainual hit a problem a lot of growing companies will recognize. Decisions were getting made in meetings that weren’t wrong, exactly. They just didn’t fit the company the leadership team was trying to build. Chris’s instinct was to get more involved. Sasha talked him out of it: the goal wasn’t more of Chris in every decision, it was a team that could think the way he would.

What came out of that took three or four months. Chris, Sasha, and Chelsea from the Trainual team traded voice notes and stories, and each idea became a principle with a real example attached. This episode walks through all 18, with the stories behind them: why Trainual passed on a PPP loan it qualified for, the childhood screensaver behind “do it now,” the pink elephant plushies in the conference rooms, and why a helicopter is the right image for most decisions.

It’s a shorter one, recorded with a leadership meeting 35 minutes away. It opens with the Berlin Marathon: a deliberately slow 5:13 finish, run together and talking the whole way. Chris takes a lesson from it about how going all out in one area of your life can cause something else to break.

Key Takeaways:

• Principles give people autonomy without costing you alignment. Trainual had core values from day one. Decision principles came later, once the team was too big for everyone to absorb how leadership thinks just by being in the room. The point isn’t control. It’s trust with guardrails, so people don’t have to Slack someone for approval before they move.
• Write down the story, not just the rule. Every principle comes with an example of when it applied. For front page news, the example is from 2020. Trainual qualified for a PPP loan but had money in the bank, and Chris didn’t want to take funds meant for businesses struggling to make payroll, or see that decision on the front page. The lesson is to follow the spirit of the law, not just the letter. Stories like that are what make a principle usable in a gray-area moment.
• Match the speed of a decision to how reversible it is. Helicopter decisions can land right back where they took off. A product test that touches 20 customers can be switched off in seconds, so ship it. Airplane decisions need a runway and a long loop to come back down. A change every website visitor sees is hard to walk back, so bring in stakeholders first. Do it now and failure is encouraged give the team permission to move fast. The VC mindset is the counterweight: know your lane, and don’t chase everything.
• Make hard conversations normal. The pink elephant principle, taken from early advisor Scott Fritz’s ground rules for annual planning sessions, means addressing tough issues in real time instead of letting them linger. Challenge how it’s done, but respect who has done it: ask why a process exists before calling it broken. Default to trust pairs with curiosity gets answers. Not every decision can be shared as a company grows, but anyone can ask. Sasha credits that pairing with building psychological safety on the team.
• Decide like you’ll be around for a long time. Ignore sunk costs, even if that means killing a project that’s 90% done, because every day is a new decision. Make investments, not expenses, by knowing what return would justify a spend before you make it. And be long-term greedy: pass on what’s opportunistic now for what’s right for the business over time.

The 18 Decision Principles:

1. Front page news. If a decision unexpectedly made the front page, would you be proud of it? Operate knowing you could publicly defend every decision you make.
2. How you do one thing is how you do everything. Leave everything better than you found it.
3. Make investments, not expenses. Know what you want to get out of every expense for a positive ROI.
4. Do it now. Process information quickly and take action.
5. Default to trust. You don’t have to earn trust on the Trainual team. It’s given, and it’s reinforced through transparency.
6. Curiosity gets answers. If you want to know something, ask.
7. Have fun with it. You spend more time at work than anywhere else, so it should be fun.
8. Failure is encouraged. Moving fast means not everything will work, and it takes a lot of at-bats to find what does.
9. Challenge how it’s done, but respect who has done it. Don’t shy away from conflict, but be kind and respectful with feedback.
10. Ignore sunk costs. Every day is a new decision, regardless of what’s already been spent.
11. VC mindset. Know your lane, and focus where your portfolio of bets has the best chance of success.
12. Helicopter vs. airplane decisions. Act quickly on decisions that are easy to reverse, and slow down on ones that are hard to reverse or wide in impact.
13. Pink elephant. Address tough issues in real time, and don’t let awkward situations or uncomfortable feedback linger.
14. Own your own experience. If something isn’t working, come with a solution instead of a complaint.
15. No loose ends. Close the loop so nothing slips through the cracks.
16. Authenticity: walk the talk. No stock photos, and don’t filter who you are at work.
17. People first. Put your oxygen mask on before helping others, because work is only one part of your life.
18. Long-term greedy. Skip short-term wins in favor of the right long-term decision.

Chapter Markers:

[0:00] Cold open: a five-year anniversary party hat

[1:00] Back from Munich: Oktoberfest with the kids

[3:09] The Berlin Marathon at a conversational pace

[5:48] From race principles to decision principles

[6:39] What broke at 40 employees

[9:25] Autonomy needs guardrails

[10:55] Front page news

[11:57] Passing on the PPP loan

[12:53] How you do one thing is how you do everything

[13:47] Make investments, not expenses

[15:20] Do it now

[17:09] Default to trust and curiosity gets answers

[18:14] Have fun with it

[19:08] Failure is encouraged

[19:58] Challenge how it’s done, but respect who has done it

[20:58] Ignore sunk costs

[22:05] VC mindset

[22:57] Helicopter vs. airplane decisions

[25:04] Pink elephant

[26:10] Own your own experience

[26:48] No loose ends

[27:55] Authenticity: walk the talk

[28:41] The AI-edited ad that backfired

[29:26] People first

[30:20] Long-term greedy

[31:55] Straight into the leadership meeting

Have a topic you’d like covered? Connect with the hosts on LinkedIn — Chris, Jonathan, and Sasha — or email chris@trainual.com.

Want more resources from this episode? We’ve got an episode recap, replay, and every template, process, and resource we covered right here: Organize Chaos

Trainual

Organize Chaos is where founders and leaders learn how to build businesses that scale. Hosted by Chris Ronzio, Jonathan Ronzio, and Sasha Robinson, each episode explores the systems, leadership, operations, performance, and AI strategies behind high-performing organizations. Through candid conversations, practical frameworks, and real-world experience, they help you replace chaos with clarity — so your business can grow with confidence.

This is one of a few podcasts from Trainual, a software platform that helps businesses build playbooks to train and grow their team. You can check out the rest of our shows here: Podcasts