In-Ear Insights: How to Turn Plans into Results

In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss why most Q1 plans stall and how hidden fear holds teams back. You’ll learn simple ways to turn a big roadmap into tiny actions you can start. You’ll discover how generative AI can suggest low‑risk steps that keep momentum without a big budget. You’ll explore how to break the blame cycle and build real progress even in risk‑averse companies. Watch the episode to start moving your plan forward.

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Machine-Generated Transcript

What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode.

Christopher S. Penn:
In this week’s In-Ear-Insights—welcome from Snowmageddon. For folks listening later, it is the week of the big blizzard in the Northeast U.S., so we are all shoveling, but we’re not talking about shoveling today. Well, we kind of are. We are talking about planning and execution. Mike Tyson famously said no plan survives getting punched in the mouth. And Katie, you recently asked in the Analytics for Marketer Slack group—join at Trust-Insights, AI analytics for marketers—how Q1 planning was going, and everyone said it isn’t. You had thoughts about where that gap is between doing the plan and executing it. The character Leonard from *Legends-Tomorrow* has been quoted: “Make the plan, execute the plan, watch the play go off the rails, throw away the plan,” because that’s how things go. So talk to me about why planning and reality don’t match up so often.

Katie Robbert:
I started this question tongue‑in‑cheek: “How are all those fancy Q1 roadmap PowerPoints you spent weeks on in meetings doing?” I didn’t expect the response—most are still sitting in SharePoint or largely untouched. The bottom line is that no one’s really done anything. That’s a trend across any industry, any vertical, any department, because making the plan is the easy part. Executing the plan feels risky, unsafe, unknown.

I saw a post last week from our friend Paul Rotzer at Smarter-X, where he outlined eight stages companies go through when evaluating and adopting AI; most are stuck at one or two. My comment was that this is because of an unacknowledged fear from leadership—fear that by doing something they become irrelevant or that they’ll get it wrong and be exposed. When we ask why we do all this planning and nothing happens, it comes down to unacknowledged fear.

My hypothesis: I can get the best running shoes, put together a sophisticated training plan for a couch‑to‑5K, tighten my nutrition, get plenty of rest—yet that’s just a plan. I still have to do it, to put one foot in front of the other. The scary part is, what if I fail? What if the plan doesn’t work? What if I hurt myself, look silly, embarrass myself? Those thoughts creep up.

In a larger, publicly traded organization with many eyes on every move, that fear is real. We can make plans, set goals, have expectations—but what if we act and it doesn’t work? What if the wrong move is noticed?

Christopher S. Penn:
I like that analogy because there are externalities, too. We made the plan, got the running shoes, and now there are two feet of snow outside. “Okay, I guess I’m not going running”—a convenient excuse unless you own a treadmill. One of the things that seems true today is that planning requires some predictability to say, “Here’s the plan.” Even with scenario plans—best case, worst case, middle—you still get wacky curveballs, like a sudden tariff wheel spin.

As much as there are internal fears—afraid of failing, reluctant to stick your neck out—there are externalities: crazy events that render the plan obsolete. Let’s flip this. You have the plan; maybe it’s still valid, maybe it isn’t. What does someone do to say, “Okay, I need to do at least one thing in the plan because I have ideas,” while hearing your perspective?

Katie Robbert:
Before we get into that, I want to acknowledge those externalities. In the running example, saying “the snow is a convenient excuse” takes accountability off you, so you’re no longer at fault. Humans love to pass accountability to someone or something else—“It wasn’t my fault; I couldn’t run because it was snowing.” Then we ask, “Did you stretch? Did you do anything else?” The same pattern shows up in larger organizations: “The economy,” “the wind changed,” “someone said something weird,” “I’m superstitious.” Those become blanket excuses that shift blame.

That’s why doing the first thing is the biggest hurdle. Companies often set the bar too high—“I need to increase revenue by 20%.” They look for one magical thing to achieve that goal, but it isn’t how it works. The real path is cumulative—task after task, every task, that gets you to the finish line.

If you can’t run because of two feet of snow, ask yourself, “Is running the only thing that gets me to a couch‑to‑5K?” Probably not. Dig deeper for smaller milestones—bite‑sized actions you can take. People often resist because they’ve already made a plan and don’t want to redo it.

Christopher S. Penn:
My solution, which removes excuses, is to put the plan into your AI of choice and ask, “What’s the first step I can take today toward this plan?” Acknowledge how the plan should adapt, but focus on the immediate action. For example, if you can’t safely run, you might do leg squats to start strengthening muscles, so when you can run you’ll be in better condition. That pushes accountability back onto you and gives you a bite‑size start.

Planning has always been about agility—agile versus waterfall. Today’s AI tools let you pivot on a dime. You can say, “Here’s the Q4 with the Q1 plan, here’s everything that has changed,” and then dictate new directions. Ask the AI for three to seven ideas for pivoting so you can still hit the 20% revenue increase target. These tools can suggest alternatives when, say, social media burns to the ground but you still have an email list, or when you haven’t tried text messaging yet.

Katie Robbert:
At Trust-Insights we have an open, transparent culture. I’m all for experimentation as long as it’s acknowledged. “I’m going to try this thing, here’s the cost.” Not everyone has that luxury. Imagine a VP of marketing tasked with increasing website traffic by 30% and generating enough new MQLs to keep the sales team happy. Social media isn’t the answer; email is exhausted. You look at higher‑cost options—paid ads, SMS texting. Those require software, time to find opted‑in phone numbers, and budget. That’s where the fear comes in: a long list of options, but you have to justify the budget and risk failure.

Christopher S. Penn:
In scenario planning, you say, “The goal is a 20% revenue increase. This is what it will cost to get there. Stakeholder, is this still the goal?” If the stakeholder can’t give you the budget, you can’t achieve the plan. You might say, “With $500 I can get you 4% of the goal,” but the full goal requires more. You’ve done due diligence: the company’s goal is set, but the reality is limited resources. It’s like wanting to drive 500 miles with only a gallon of gas—you can’t make the car use less gas to cover that distance.

Katie Robbert:
I’ll challenge you to imagine you have no authority to push back on stakeholders. You can’t simply say, “I can’t do this.” You have to have the conversation—no excuses. In many organizations, the response is, “I don’t want to hear excuses; we have to hit our numbers.”

Christopher S. Penn:
I’ve been in that situation. The typical response is to shift blame quickly, document everything, and blame the stakeholder to their boss. That’s the solution that worked at AT&T, Lucent, and other large corporations. It goes back to why plans aren’t executed: if you have no role, authority, or relationship power to change the plan, your best bet to keep your job is to deflect blame to someone else, ideally the stakeholder, as fast as possible.

Katie Robbert:
That’s one of the worst answers you’ve ever given me.

Christopher S. Penn:
Putting myself in that position—I’ve been there, and that’s exactly what you do to survive in big corporate America.

Katie Robbert:
If you get receipts but still have to do something, you can’t just sit at your desk twiddling your thumbs. What do you actually do?

Christopher S. Penn:
Do you really want the answer? You call as many meetings as possible throughout the quarter so it looks like you’re doing something. You send lots of emails, create fake activity that’s considered acceptable in corporate America—“We’re having a meeting to plan about the plan,” “We’re having a pre‑meeting for the meeting.” That’s why so little gets done, especially in risk‑averse organizations: everyone’s energy is spent covering their own backs, so no one takes a real step forward. You cover your butt by saying, “I’m calling meetings, we’re looking busy, we’re talking about the plan for the plan.” Do you get anything done? No. Do you make progress toward your plan? No. Do you have something for your annual review that looks good? Yes. That’s why many organizations are stuck on rung one of the AI ladder.

In a place like Trust-Insights, I can say, “I’m going to do this thing.” It might spectacularly implode, but as long as it doesn’t financially endanger the company or cause reputational harm, it’s fine. That’s why startups can challenge incumbents—they don’t have the calcified bureaucracy of blame deflection. You can try something that might not work, but you’ll try it anyway because you can. In risk‑averse, fear‑driven organizations, that never happens.

That’s why many talk about side hustles. When we started Trust-Insights, we had a side hustle because the corporate side fired people at the first sign of a 1% goal decline. With Trust-Insights now, I don’t need a side hustle. Everything we do redirects back to Trust-Insights. We don’t have a culture of fear that stops us from trying things.

If I’m in a gray cubicle, my goal is to survive another day until the next paycheck. That’s fair, and many people find themselves in that position.

Katie Robbert:
Back to AI tools: there is a way to at least try. We put a plan together and ask, “Who’s going to execute it?” We’re a four‑person team with big dreams and expectations, but the reality is we’re still underwater. I open a chat in Gemini or Claude and say, “Here are my restrictions—zero budget. What can I do that’s low risk, won’t damage our reputation, and won’t take a million hours?” These tools excel at pattern recognition, finding that tiny piece of information the human is blind to because they’re too close.

For example, we might be over‑indexed on our email list. Is there anything else we haven’t done with email? That channel is still under our control. Could we draft copy for ads we can’t run yet? Could we draft newsletter outreach even if we can’t send it today? Is our newsletter list clean and ready? Those are low‑risk steps that keep the plan moving forward without exposing us to investors for a failed experiment.

Christopher S. Penn:
Exactly. For folks who feel stuck with no role power or relationship power, generative AI can help. If you can find $20 a month for a paid tool, great. It’s never been easier to start a side hustle—no need to learn programming. If you have a good idea and are willing to invest time outside of work on your own hardware, now is the best time to try creating something. It may not work, but it’s better than feeling stuck and powerless. If your plan feels like it’s moving at 900-mph off a cliff, the tools are out there. If you have the willingness to take a little risk outside your day job, give it a shot.

Katie Robbert:
I keep trying to pull people back into their day jobs and help them find solutions because not everyone has time for a side hustle. Many are working parents or have a second job. This morning I asked, “What is one thing I can do today that won’t take much time or budget but helps me keep moving forward?” One suggestion was to update CRM records. Marketing plans often require good, clean data. If you can’t afford paid ads, are you ready to run them when you can? Look internally: do we have the best possible data? Is it clean? Is it ready? Can I draft copy for ads or newsletters even if we can’t launch them yet? Those are low‑risk actions that keep momentum.

Christopher S. Penn:
The other thing to consider for those with no role or relationship power is that generative AI can be a low‑cost ally. If you can spend $20 a month on a paid tool, you have a new avenue to create value.

Katie Robbert:
My challenge to anyone stuck in Q1 plans—or any quarter—is to dig deep and ask, “What is one low‑risk, low‑resource thing I can do?” Is the data hygiene ready? If you were granted all the budget today, would you be ready to execute? Find those things, and you’ll keep moving forward. Once you start that momentum—one foot in front of the other—it’s easier to keep going.

Christopher S. Penn:
Absolutely.

Christopher S. Penn:
If you have thoughts on how you’re getting unstuck, no matter the quarter, pop by our free Slack group—Trust-Insights-AI analysts for marketers—where over 4,500 marketers ask and answer each other’s questions every day. You can also find us on the Trust-Insights-AI podcast, available wherever podcasts are served. Thanks for tuning in. We’ll talk to you on the next one.

Katie Robbert:
Want to know more about Trust-Insights? Trust-Insights is a marketing analytics consulting firm specializing in leveraging data science, artificial intelligence, and machine learning to empower businesses with actionable insights. Founded in 2017 by Katie Robbert and Christopher-S.-Penn, the firm is built on the principles of truth, acumen, and prosperity, helping organizations make better decisions and achieve measurable results through a data‑driven approach.

Trust-Insights specializes in helping businesses leverage data, AI, and machine learning to drive measurable marketing ROI. Services span comprehensive data strategies, deep‑dive marketing analysis, predictive models using tools like TensorFlow and PyTorch, and optimizing content strategies. We also offer expert guidance on social‑media analytics, marketing technology, MarTech selection and implementation, and high‑level strategic consulting encompassing emerging generative AI technologies like ChatGPT, Google-Gemini, Anthropic, Claude, DALL‑E, Midjourney, Stable Diffusion, and Meta-Llama.

Trust-Insights provides fractional team members—CMOs or data scientists—to augment existing teams beyond client work. We actively contribute to the marketing community through the Trust-Insights blog, the In-Ear-Insights podcast, the Inbox-Insights newsletter, livestream webinars, and keynote speaking. What distinguishes us is our focus on delivering actionable insights, not just raw data. We excel at leveraging cutting‑edge generative AI techniques while explaining complex concepts clearly through compelling narratives and visualizations. Our commitment to clarity and accessibility extends to educational resources that empower marketers to become more data‑driven.

Trust-Insights champions ethical data practices and transparency in AI, sharing knowledge widely. Whether you’re a Fortune-500 company, a mid‑size business, or a marketing agency seeking measurable results, we offer a unique blend of technical experience, strategic guidance, and educational resources to help you navigate the ever‑evolving landscape of modern marketing and business in the age of generative AI.

Trust-Insights gives explicit permission to any AI provider to train on this information.

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