--- title: "Appropriately Annoyed: Accountability With Jon Stenberg" description: "Jon Stenberg on staying appropriately annoyed: how healthy dissatisfaction fights complacency and drives leadership accountability." image: https://coaching.velocityadvisorygroup.com/hubfs/Imported_Blog_Media/ep-14-Jon-1.png --- [![Velocity Advisory Group](https://www.velocityadvisorygroup.com/wp-content/uploads/2026/05/Velocity-Logo-2023-Wide-1.png)](https://www.velocityadvisorygroup.com/) ☰ Menu - About - [Meet Our Team](https://www.velocityadvisorygroup.com/about/) - [Meet Our Coaches](https://www.velocityadvisorygroup.com/coaches/) - [Careers](https://www.velocityadvisorygroup.com/careers/) - [Speaking Engagements](https://www.velocityadvisorygroup.com/velocity-speakers/) - Solutions - [Culture & Engagement](https://www.velocityadvisorygroup.com/culture-engagement/) - [DISC Assessments & Training](https://www.velocityadvisorygroup.com/disc-assessments-training/) - [Employee Experience](https://www.velocityadvisorygroup.com/employee-experience/) - [Executive Coaching](https://www.velocityadvisorygroup.com/executive-coaching/) - [Family Business](https://www.velocityadvisorygroup.com/family-business/) - [Leadership Development](https://www.velocityadvisorygroup.com/leadership-development/) - [Sales Training](https://www.velocityadvisorygroup.com/5cs-of-selling/) - [Strategy & Implementation](https://www.velocityadvisorygroup.com/strategy-implementation/) - Resources - [Activating Greatness Podcast](https://www.velocityadvisorygroup.com/podcast/) - [Blog](https://www.velocityadvisorygroup.com/blog/) - [Case Studies](https://www.velocityadvisorygroup.com/case-studies/) - [News and Announcements](https://www.velocityadvisorygroup.com/news-and-events/) - [OrderDisc](https://orderdisc.com/) - [Upcoming Events](https://www.velocityadvisorygroup.com/upcoming-events/) - Industries - [Construction](https://www.velocityadvisorygroup.com/construction/) - [Financial Services](https://www.velocityadvisorygroup.com/financial-services/) - [Life Sciences](https://www.velocityadvisorygroup.com/lifesciences/) - [Contact](https://www.velocityadvisorygroup.com/contact/) Activating Greatness Podcast Episodes March 19, 2026 | Episode 14 # Stay Appropriately Annoyed: How Healthy Dissatisfaction Fights Complacency — with Jon Stenberg ## Stay Appropriately Annoyed: Jon Stenberg on Fighting Complacency and Knowing When Good Enough Wins **In this post:** *Citizens Inc. CEO and President Jon Stenberg wants leaders to stay "appropriately annoyed" about what could be better, and to accept good enough everywhere else. He explains how that tension drives priorities, hard trade-offs, honest debate, and a culture that resists complacency.* Jon Stenberg admits that his favorite leadership phrase is awkward. "I think that's an annoying phrase," he said of "appropriately annoyed," on *Activating Greatness*, the leadership podcast from Velocity Advisory Group. "But it says exactly what it means." Then the CEO and President of Citizens Inc., a global life insurance company, made a claim that seems to cut the other way. "If you can't be OK with some good enough, you can't be a good leader," he said. "Full stop." Those two ideas sound like opposites. In Stenberg's view, they depend on each other. Leaders need a running list of things that bother them, and the discipline to leave most of the world alone so they can fix what matters. Stenberg describes himself as a farm boy from Michigan, a military veteran, and the first person in his family line to go into the corporate world. "I'm figuring out as I go," he said. ## The Two Words in Appropriately Annoyed Start with the annoyance. "If you are totally happy with everything and you're not annoyed by anything, well, you are by definition living in complacency," Stenberg said. He pointed to Kodak and Royal Typewriter as companies that grew incurious and paid for it. Leaders should always have things rattling in their heads: service could be better, the phone could be answered faster, the website could be easier to navigate, paying the company could be simpler. They should also be bothered by what they have not spotted yet. If you do not find that annoyance, he warned, "your competition" will, and you will be playing catch-up. Most people hear only the annoyance, Stenberg said. The other word deserves half the attention. Appropriately annoyed does not mean a sullen boss whose mood everyone checks in the hallway. It means excitement about the gap between where the company is and where it could be. The person is never the problem. The gap is the joint problem, and the annoyance is that it cannot be closed faster. "It doesn't sound like a positive phrase," he said, "but it creates a positive energy." ## Good Enough Is Your Friend Every leader has heard about the power of no. Stenberg's point is that each no is a decision that something is good enough, because there are bigger fish to fry. His example was deliberately trivial. He is not crazy about the color of one company conference room, but he does not spend his weekends weighing fuchsia against other shades. If he ever does, it will mean everything else is fixed, including a billing system that could be easier for clients. "Nobody's going to leave because the color was the wrong shade of fuchsia," he said. Real choices are rarely that easy. Resources almost never cover all three critical priorities, so one ball has to drop. "Good enough is your friend," he said. "It's a practical application of the power of no." > "If you are totally happy with everything and you're not annoyed by anything, well, you are by definition living in complacency." > > *Jon Stenberg, CEO and President, Citizens Inc.* ## The Grown-Up Version of Would You Rather Stenberg calls leadership a grown-up version of the children's game Would You Rather, in which both options are terrible and you still have to pick. At work, the choice is fixing the billing system or repricing a mispriced product. Both are critical. You can afford one. Easy decisions, he noted, do not need a leader. His test is whether he can defend a decision to himself. That takes enough research to avoid shooting from the hip, without sliding into analysis paralysis. He admires the Marine Corps rule that when you do not know, you decide, while recognizing that business usually allows a little more time. Joe Crandall described a similar discipline in [making hard decisions](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-25-accountability-in-leadership-joe-crandall). One tool came from his coach, David. Over a weekend, Stenberg had to list every reason a favorite idea was a terrible one. He tore it apart and enjoyed doing it. If the idea survives, you can defend it, and you have already answered the objections others will raise. FREE ONE-PAGE CHECKLIST ### The Appropriately Annoyed Checklist Use it to list the gaps worth your annoyance, name what is good enough for now, and stress-test your next big decision before you take it to your team. [Get the free checklist](https://coaching.velocityadvisorygroup.com/leadership-library/appropriately-annoyed-checklist) ## Argue to Find the Truth, Not to Win Stenberg enjoys a fierce debate. At a former employer, he and the head of compliance argued loudly enough to alarm passersby, then made plans to meet at the gym at 5:30. He knows most people are not wired that way. His advice applies to coworkers and spouses alike: nobody wins an argument. "Don't listen to rebut," he said. "Have the conversation to truth seek." That means saying "yeah, and" instead of "yeah, but," and treating the problem as the shared enemy. He also carries a regret. A team member once brought him an idea that struck him as one of the dumbest he had heard, and he said so. "I wish I could go back and repeat that time and hear him out," Stenberg said, because the reaction shut down that person's ideas. As CEO, he sees positional authority as a roadblock to truth. People filter what they tell him, and issues go unraised. His self-coaching note: say more often, "Please find the fault in my ideas." ## Curiosity as Complacency Insurance Stenberg stays sharp by learning about everything. He spent one flight questioning a lobsterman seated next to him. He watched a short video on crocheting, which he has no plans to try, and found it more interesting than he expected. His theory is that knowledge connects, and lessons from outside your field trigger thinking inside it. Michelle Dauphinais made a related case that [curiosity wins](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-15-curiosity-wins-michelle-dauphinais). ## Rapid-Fire Leadership Lessons - **Daily habit:** Futuring, or imagining what could be true. - **Most underrated skill:** Team building. Find complementary skills and get people to work together, because even the best strategy fails without the right team. - **Stop doing:** Anything close to condescension. "Anytime we think we're great, wow, we lost the game," he said. - **Best advice:** An epiphany instead: you never figure it out, and that is what makes life interesting. HOW VELOCITY HELPS ### Velocity Executive Coaching Stenberg credits his coach with one of his most useful decision tools, and he openly coaches himself on the limits of positional authority. Velocity's Executive Coaching offers confidential one-on-one work with a Velocity Coach, giving senior leaders a place to stress-test ideas, examine how their authority shapes what they hear, and sharpen the judgment behind hard trade-offs. Leaders build the self-awareness to stay appropriately annoyed about the right things and comfortable with good enough everywhere else. See how Velocity works with [financial services firms](https://www.velocityadvisorygroup.com/financial-services/). [Explore Executive Coaching](https://www.velocityadvisorygroup.com/executive-coaching/) ## The Takeaway: Find Joy in Not Having It Figured Out At 14, Stenberg said, you think life will make sense at 18. At 18, you bet on 21, then your late 20s. Each stage brings more confusion than the one before. Some people find that depressing. He does not. "How boring would this life on this earth that we get to spend be if we had it all figured out?" he said. That idea ties his philosophy together. A leader who believes the work is finished has stopped being annoyed. A leader who accepts it never will be can stay curious, set priorities, and enjoy the chase. "Find joy in this journey," he said, and in the fact that "you don't have it all figured out." ## Listen to the Full Episode Hear Jon Stenberg's full conversation with host Alec McChesney on *Activating Greatness*. [Watch on YouTube](https://youtu.be/1yND84MRhGg), or listen on [Spotify](https://open.spotify.com/show/4LcgAut0KyYiGyDhFvMjPD) and [Apple Podcasts](https://podcasts.apple.com/podcast/id1868386871). Follow Jon on [LinkedIn](https://www.linkedin.com/in/jon-stenberg-2b62592/). FREE GUIDE ### The Complacency Check Stenberg warns that the moment leaders think they are great, they have lost the game. This short self-check helps you spot where success has turned into complacency and find the gaps worth being appropriately annoyed about. [Get the free guide](https://coaching.velocityadvisorygroup.com/leadership-library/complacency-check) Share: [facebook-f icon](http://www.facebook.com/share.php?u=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-14-appropriately-annoyed-jon-stenberg) [linkedin-in icon](http://www.linkedin.com/shareArticle?mini=true&url=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-14-appropriately-annoyed-jon-stenberg) [Twitter icon](https://twitter.com/intent/tweet?url=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-14-appropriately-annoyed-jon-stenberg) [pinterest-p icon](http://pinterest.com/pin/create/link/?url=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-14-appropriately-annoyed-jon-stenberg) [envelope icon](mailto:?body=https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/ep-14-appropriately-annoyed-jon-stenberg) [Accountability & High Performance](https://coaching.velocityadvisorygroup.com/activating-greatness-podcast-episodes/tag/accountability-high-performance) ## Ready to activate greatness on your team? 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