How to Make Difficult Business Decisions

As a fighter pilot and military leader, I often had to make time-critical decisions. I never had perfect information or a 100% solution, but I still needed to be decisive and take action. It wasn’t always easy, but the more experience (and practice) I had, the easier it became to make decisions quickly. How did I get to the point where I felt confident in making quick decisions? 1️⃣ Prepare – do the research, know your stuff. It’s easier to make a quick decision when you have done the work to be knowledgeable about a situation. Going in cold is much more difficult. 2️⃣ Plan for contingencies – think through contingencies in advance. If you think through the “what ifs” in advance, then you will feel better prepared to make a decision. 3️⃣ Seek input – you don’t have to have all the answers. When time permits, seek out input from experts, and also from your team members who are closest to the action and will be most impacted by your decision. 4️⃣ Evaluate the pros and cons – Think through the consequences of your decision. How will it impact your team? What are the outcomes related to your decision? 5️⃣ Make the decision – Make a timely decision and communicate it to your team. Explain your thought process and reasoning to help gain buy-in and understanding. 6️⃣ Hold yourself accountable for the decision. If it’s wrong, admit it, and go back to adjust. We can all face challenges that can make us feel stressed or worried about making a timely decision. But when it comes down to it, leaders need to be prepared to make tough decisions in challenging circumstances when time is limited. #DecisionMaking #LeadershipDevelopment #LeadWithCourage

Have you ever seen one department blamed for a system or strategy issue because their result is where it's showing up? In B2B tech, I see this constantly: → "We have a marketing problem" (but it's really a product differentiation issue) → "Sales isn't closing" (but we're spread across too many segments) → "Pipeline is down" (but the market assumptions in our plan are wrong) Marketing and sales are the tip of the spear to the market. Problems originating in other parts of the business sometimes get blamed on them when the source may be a COMPANY STRATEGY problem, rather than a departmental failure. Before you fire that CMO or CRO - consider if it really IS a pipeline issue... or if there's a systems or strategy issue. Some tips from today's article: 1) Name the systems issue - As you explore part of the business that’s struggling, look for the interconnected parts that might be contributing rather than treating issues in silos 2) Listen more deeply to customer feedback - Customers don't know your org chart. While listening can be a cacophony of opinions, painful truths are often publicly shared and reveal systemic issues that span multiple departments. Pay attention to complaints that seem to touch multiple areas of your business—these are often symptoms of deeper systems problems that require cross-functional solutions rather than departmental fixes. 3) Create space for constructive truth-telling - As a leadership team, you need to foster the trust and structure that allows systemic issues to be named and addressed, even when they implicate other functions or expose uncomfortable realities. 4) Be specific about the HOW, not just the numbers - Many companies use their financial plan and KPIs as their strategy. Their annual plans and quarterly goals describe the numbers more than HOW to get there and what trade-offs are necessary. Make sure your annual and quarterly plans include how you expect the market and competitors to evolve, how you define and allocate investments to different audiences, regions, and verticals, and how you plan to differentiate in the short and long term. 5) Make hard decisions, don’t kick the can down the road - Systems problems rarely resolve on their own. And because they are diffuse, generally not time-bound, and have no right answer, it’s hard to make quick progress on them. But choosing to act, even imperfectly, is better than pretending the issue doesn’t exist. 6) Keep asking: What are we missing? Periodically step back and ask what might be hiding in plain sight - is there an overlooked “connective tissue” that could unlock progress? As an executive team, it’s easy to get deep in execution and run out of time for strategy. But if there’s illness in a part — it’s really important to consider the health of the system.

Ever been in a meeting that feels like a hamster wheel of indecision? The same points circling endlessly, everyone is tired but no conclusion in sight? Decision paralysis costs organizations dearly—not just in wasted meeting time, but in missed opportunities and team burnout. After studying teams for years, I've noticed that most decision stalls happen for predictable reasons: • Unclear decision-making process (Who actually decides? By when?) • Hidden disagreements that never surface • Fear of making the wrong choice • Insufficient information • No one feeling authorized to move forward    The solution isn't mysterious, but it requires intention. Here's what you can do: First, name the moment. Simply stating, "I notice we're having trouble making a decision here" can shift the energy. This small act of leadership acknowledges the struggle and creates space to address it. Second, clarify the decision type using these levels: • Who has final authority? (One person decides after input) • Is this a group decision requiring consensus? • Does it require unanimous agreement? • Is it actually a collection of smaller decisions we're bundling together?    Third, establish decision criteria before evaluating options. Ask: "What makes a good solution in this case?" This prevents the common trap of judging ideas against unstated or contradictory standards. Fourth, set a timeline. Complex decisions deserve adequate consideration, but every decision needs a deadline. One team I worked with was stuck for weeks on a resource allocation issue. We discovered half the team thought their leader wanted full consensus while she assumed they understood she'd make the final call after hearing everyone's input. This simple misunderstanding had cost them weeks of productivity. After implementing these steps, they established a clear practice: Every decision discussion began with explicitly stating what kind of decision it was, who would make it, and by when. Within a month, their decision-making improved dramatically. More importantly, team members reported feeling both more heard and less burdened by decision fatigue. Remember: The goal isn't making perfect decisions but making timely, informed ones that everyone understands how to implement. What's your go-to approach when team decisions get stuck? Share your decision-making wisdom. P.S. If you’re a leader, I recommend checking out my free challenge: The Resilient Leader: 28 Days to Thrive in Uncertainty  https://lnkd.in/gxBnKQ8n

90% of startups don’t fail because of: Bad marketing, a weak team, or even a poor product. They fail because they lack a repeatable decision-making process. Here’s the framework I use to make better, faster decisions in business. I call it “The Iteration Loop.” It’s a structured way to identify what’s working, what’s broken, and what to do next, without getting stuck in endless guesswork. It gives you a systematic way to eliminate bottlenecks, optimize execution, and scale with clarity. Here are the 6 phases: 1. Bottleneck Identification 2. Clarifying the Goal 3. Solution Brainstorming 4. Focused Execution 5. Performance Review 6. Iterate & Improve 1️⃣ Bottleneck Identification Before you can fix anything, you need to identify the real problem. Most entrepreneurs spin their wheels solving the wrong issues because they never dig deep enough. To get clarity, ask: + What's the biggest constraint stopping growth right now? + What metric, if doubled, would create the biggest impact? + What’s preventing us from getting there? If you don’t identify the root problem, every solution you apply will be wasted effort. 2️⃣ Clarifying the Goal Once you know the problem, define the exact outcome you’re solving for. I use a simple Three-Part Goal Formula: 1. What are we trying to achieve? 2. By when? 3. What constraints do we have? Vague goals lead to vague actions. Precision forces progress. 3️⃣ Solution Brainstorming Now, generate every possible solution—without filtering. Most people limit themselves to their existing knowledge, which is why they get stuck. Instead, ask: “If there were no rules, what would I do?” This opens up better, faster, and often simpler solutions you wouldn’t have otherwise considered. 4️⃣ Focused Execution Don’t test everything at once—test one variable at a time. Most teams waste months by making too many changes at once, leading to messy, inconclusive results. Instead, break it down: 1. Test one key assumption. 2. Measure one KPI that proves or disproves it. 3. Execute for a set period, then review. 4. Speed matters. Complexity kills momentum. 5️⃣ Performance Review Your data isn’t just numbers—it’s feedback on your decision-making process. Your job is to analyze: + Did the solution work? + Why or why not? + What does this tell us about our business? Every test refines your ability to make better future decisions. 6️⃣ Iterate & Improve Most companies don’t fail from making the wrong move—they fail from making no moves at all. The only way to win long-term is to keep iterating. Instead of fearing failure, build a culture that rewards learning. Failure + Reflection = Progress. If you aren’t improving your decision-making process, your business will eventually hit a ceiling. That’s why I built The Iteration Loop—so every problem becomes an opportunity for better, faster execution. P.S. If you want the scaling roadmap I used to scale 3 businesses to $100M and beyond, you can get it for free from the link in my profile.

Have you ever wondered what's the toughest task for a founder? It's taking decisions. Because I know my decisions today would affect my entire team. The thing is as a founder you have to make so many crucial decisions on a daily basis that at a point it becomes overwhelming. It's known as decision fatigue and almost all founders suffer from it. This is because when the business is in a rapid growth phase old systems often stop working and there is something new every day. Here are 3 tips that helped me overcome this for OWLED: 1) Implementing a personal decision-making framework:  Create a simple matrix to evaluate choices quickly. Prioritize decisions based on impact and strategic alignment. 2) Batch your decisions and protect peak energy hours: Group similar decisions into focused time blocks. Tackle critical choices when your mental energy is at its highest. 3) Empower your team to make autonomous decisions. Provide clear guidelines to reduce your personal decision load. As a founder, you can't avoid decision-making. You can't solve this by making fewer decisions but by implying strategies that help you make rational decisions. What are the toughest decisions you have taken in 2024?

You don't get paid for time. You get paid for judgment. Most people think CEOs work harder than everyone else. Wrong. We get paid for making decisions when nobody knows what to do. This hit me hard while we were building Quest Nutrition. Everyone told us it was impossible: "You can't make protein bars without corn syrup." Every machine in the industry was built for that sticky liquid. Without it, the machines wouldn’t be able to mix the ingredients. We made a different judgment call: build new machines. That was the billion-dollar decision. Most founders focus on working harder instead of deciding better. They avoid difficult decisions instead of embracing them. They let industry limitations define their reality. When everyone says "that's impossible," ask one question: Does it violate the laws of physics? If no, it's just an engineering problem. We built our own manufacturing from scratch because everyone said healthy protein bars were impossible. But it wasn't impossible. It was only impossible because of how existing machines worked. Most founders get emotional when problems get hard. The best ones get systematic. The Framework for Better Judgment: 1. Find the "Impossible" Problem - What is everyone in your industry saying can't be done? 2. Strip Away Emotion - Is it actually impossible or just hard? 3. Build the System - Engineer your way around industry limitations. 4. Execute on the Decision - Turn uncertainty into predictable results. Your market value isn't based on how many hours you log. It's based on how much uncertainty you can eliminate when it matters most. The bigger the chaos you can turn into clarity, the bigger the check you can write yourself. Stop optimizing for effort. Start optimizing for judgment. Use better judgment on your next business move. Validate your idea and get clarity in 30 minutes: https://buff.ly/I6yjKOn

I was asked recently to outline how we make the hard decisions at Enveda. What do we do when there are no obvious answers? Here’s the truth. Hard decisions don’t get easier with more time or analysis. But we have found that they do get clearer. Here’s how we approach them at Enveda: 1. Start with principles. Define them up front. Embrace the tradeoffs. Talk about them openly. Admit there isn’t a perfect. 2. Separate decision quality from outcome. A good decision can lead to a bad outcome — and vice versa. 3. Watch for sunk costs. Just because it took time or money doesn’t mean it deserves more. 4. Move fast. Perfect is the enemy of progress. Our only regret has been that we didn’t move on it before. 5. Communicate clearly. Share the decision and the thinking behind it as transparently as possible. Have a comms plan to help your people leaders talk about it authentically. We don't wait for certainty.We optimize for clarity. That’s how we’ve made some of our boldest, and often best, decisions. #DecisionMaking #Leadership #Startups #FounderLife #Strategy #ClarityOverCertainty