How to Navigate Uncertainty with Smart Choices

Leading Through Uncertainty: A Client’s Playbook for Staying Valuable When a Company is for Sale One of my executive clients recently found himself in a high-stakes situation: his company had publicly announced it was for sale. The uncertainty was immediate. Would leadership change? Would the buyer see his role as essential? Would his job even exist post-acquisition? Instead of panicking or passively waiting for answers, we developed a strategy to ensure he remained indispensable—no matter what happened next. Here’s the five-step playbook we created: 1. Be the Steady Hand in Uncertainty M&A shake-ups trigger fear, and teams look to leadership for reassurance. My client made it his mission to be the voice of reason. He focused on business as usual, keeping his team engaged and morale steady. ✔ He avoided getting caught up in speculation or gossip. ✔ He reassured his team while staying honest about what was known and unknown. ✔ He remained visible—continuing to lead with confidence while others pulled back. 2. Double Down on Business-Critical Contributions Buyers evaluate companies beyond the balance sheet. They want strong leadership that can sustain growth. We identified his highest-value contributions and amplified them. ✔ He prioritized projects that directly impacted revenue and operational efficiency. ✔ He documented successes and positioned himself as a driver of results, not just a participant. ✔ He ensured key stakeholders saw his contributions—visibility was non-negotiable. 3. Strengthen Key Relationships Relationships often determine who stays and who goes in a sale. We worked on deepening his connections internally and externally. ✔ He strengthened ties with board members and decision-makers. ✔ He reinforced his relationships with top clients—proving his value beyond the org chart. ✔ He stayed engaged, ensuring he was seen as a connector in the company. 4. Embrace Change, Not Resist It Executives who thrive in an acquisition show adaptability. Instead of fearing change, we positioned him as someone who could help lead it. ✔ He signaled his openness to new strategies and structures. ✔ He proactively identified ways he could add value post-sale. ✔ He framed himself as part of the solution—not as someone clinging to the past. 5. Have a Smart Plan B (Without Checking Out of Plan A) While he remained fully committed to the business, we also prepped for all possible outcomes. ✔ He quietly refreshed his network, ensuring he had options. ✔ He sharpened his executive brand, digital assets and unique value proposition. ✔ He stayed engaged—but positioned himself to win, whether he stayed or moved on. If your company is on the market, don’t just wait to see what happens. Take control of your value. If you’re navigating a corporate sale and want to ensure you stay relevant (or land in a better position), let’s connect.

A few years ago, I found myself in a situation that didn’t fit any of the “playbooks” I had relied on for years. I was leading a high-stakes project that suddenly shifted direction due to external forces that no one on the team had anticipated. No amount of analysis, planning, or expertise seemed enough. What helped was gathering the team and agreeing on a few guiding principles — not the answers themselves, but THE WAY we would make decisions, adapt, and move forward together. Reading this Harvard Business Review piece by Nitin Nohria, Bill George and Kayty Stanley on complex vs. complicated problems reminded me of that experience. As the authors suggest, we need a different mindset when facing complexity. COMPLICATED problems can be solved with expertise. COMPLEX problems must be navigated with intuition, resilience, and creativity. The article recounts how Corie Barry, CEO of Best Buy, led through the early chaos of Covid-19 not by trying to "solve" the pandemic but by embracing its complexity. Instead of chasing clarity where none existed, she and her team set three guiding principles: prioritize safety, avoid layoffs when possible, and focus on long-term value — even if that meant letting go of short-term earnings goals. This approach worked because Barry understood that COMPLEX problems — unlike COMPLICATED ones — don’t have tidy solutions. They require: (1) Sensemaking, not just solving. (2) Principles, not rigid plans. (3) Iteration, not a one-time fix. The article lays out thoughtful strategies for leading through complexity: - Building on your organization’s core mission and values. - Understanding the problem’s full, evolving nature. - Continuously adapting to the shifting context. - Creating real-time feedback loops. - Broadly engaging stakeholders, even when it's messy. - Preparing leaders to thrive in ambiguity, not just certainty. In today's world, recognizing whether a challenge is complicated or complex is really important. Effective leadership matters a great deal, especially when solving for complex problems. #problemSolving #challenge #complexity #creativity #learning #ambiguity #uncertainty https://lnkd.in/e_Qm2tkZ

Navigating Leadership in Turbulent Times- A few days ago, I had an interesting conversation with a friend about how Non Profits are facing this period of  unknowns and instability. For organizational leaders, the role we play in guiding our teams and ensuring the stability and resilience of our organizations has never been more critical. Here are a few things I learned about leading through uncertainty- 1. Focus with Intent We are constantly being hit with a barrage of incoherent tweets, rash decisions, and contradictory messaging that can feel overwhelming. Reacting to everything will leave us scattered, unfocused, and ineffective. Leaders must prioritize their organizational goals and focus on what they are best equipped to address. 🔑 Choose your battles wisely and resist the urge to 'play whack-a-mole' with every issue. Not every fight is yours to take on, and sometimes, the wisest move is not to fight at all. Focused leadership drives meaningful impact. 2. Embrace Collaboration - In this season of uncertainty, collaboration is not optional—it’s essential. Community and partnerships have always propelled movements forward. 🤝 Build a collaborative work culture, encouraging your team to cultivate strong relationships both internally and externally.  Collaboration builds trust, and allows people to build upon their strengths and leads to better decisions and outcomes.   3. Flexibility & Adaptability -"Be stubborn about your goals but flexible about how you achieve them." Strategy is not a fixed plan but an evolving path to reach a predetermined destination. Recognize when adjustments are needed and model adaptability for your team. 📣 Communicate openly with staff about changes and align around shared objectives, even if absolute agreement isn’t always possible. Pathways can emerge when teams are nimble and solutions-oriented. 4. Support Your Staff- Amid external crises, organizational trust often becomes strained. Now is the time to double down on creating a supportive environment for your team.  Focus on the short-term goals and the long-term mission when conflict arises. Look for areas of agreement to rally around. 💡 Consider what your organization can offer during this period, whether that’s flexible policies, open communication channels, or empathetic leadership. Teams perform best when they feel valued and supported. 5. Safeguard Your Organization - If your mission runs counter to the incoming administration’s policies, preparation is key. 📋 Run a risk assessment and review your policies/processes to ensure compliance and readiness. Develop clear protocols and maintain a strong relationship with your legal counsel.  A proactive approach will protect your organization from unnecessary risks. I can say from experience that leadership in turbulent times isn’t easy, but it’s also an incredible opportunity to model resilience, inspire focus, and foster collaboration.

A topic that has come up recently in some of my manager development programs is how to lead during times of change and uncertainty (which, let's face it, feels like the norm these days). The core question is this: How do you show up and lead others during periods of uncertainty and change when you yourself may feel uncertain about the changes happening? When one person asks this question, many others nod in agreement, highlighting the universality of what many leaders are experiencing today. In the hopes of sparking further conversations between your leaders and their peers on this topic, I wanted to share a few key ideas we discussed as potential actions for leaders to try: 📌Put on your oxygen mask first - As the saying goes, take care of yourself first. Before you respond to others, make sure you are in a good place personally amidst the change and uncertainty. It can be challenging to support others when you’re not taking care of yourself. Take time to reflect, seek support, or journal—whatever helps you process the situation. But before you lead, start with yourself. 📌 Map out what’s within your control - It’s easy to feel overwhelmed by uncertainty, but in reality, some things are within your control, and others are not. Define what’s in your control and focus your energy there. It’s not easy, but it helps reduce the stress of feeling powerless. 📌 Meet people where they are - Everyone has their own relationship with change and their own ways of coping with fear, uncertainty, and change. Your goal is to understand where each person is individually and meet them there, helping them move in the right direction. This requires listening and personalizing your approach to each individual. 📌Turn outward (and encourage others to do the same) -  During challenging times, it’s natural to want to turn inward and isolate yourself. While it’s completely reasonable to take care of yourself, remember the saying, “don’t suffer in silence.” If there’s uncertainty or change happening, you’re likely not the only one feeling it. Turn outward to your peers and colleagues. As a leader, model this behavior, and encourage your team to connect with their peers as well, if they feel comfortable. Many of society’s challenges have been solved through collaboration, and this situation will be no different. If you have other ideas or practices that are helping your leaders navigate change and uncertainty, I’d love to hear what you’re doing or trying! #leadership #leadershipdevelopment

As an A-10 pilot, launching on a mission often meant facing the unknown—uncertainty about what we’d encounter, how plans might change, and what challenges awaited. In those moments, it wasn’t just about staying focused; it was about leading with clarity and purpose to ensure the mission succeeded. As leaders, our mindset and actions set the tone for how teams navigate uncertainty. It’s not just about guiding them through the turbulence; it’s about inspiring confidence, maintaining focus, and ensuring the team stays motivated and engaged. Here’s what I’ve learned about leading effectively during times of change: 1️⃣ Model Calm & Confidence: When the path ahead is unclear, your team looks to you for cues. Staying composed—even when you don’t have all the answers—reduces anxiety and builds trust. 💡 Tip: Use clear, concise, correct communication to show control, even if you’re still processing the situation internally. 2️⃣ Balance Transparency with Optimism: Be honest about challenges while emphasizing opportunities. Acknowledge difficulties but focus on solutions and remind your team of their strengths. 💡 Tip: Frame obstacles as opportunities for growth and innovation. 3️⃣ Empower Decision-Making: Change often demands swift decisions. Trust your team’s expertise and avoid micromanaging. Empowering others not only reduces bottlenecks but boosts morale. 💡 Tip: Provide clear decision-making guidelines to ensure everyone knows their boundaries and responsibilities. 4️⃣ Prioritize Communication & Connection: In uncertain times, silence creates more doubt. Frequent updates, even if incomplete, help keep the team informed and aligned. 💡 Tip: Schedule informal check-ins to address concerns. Walk around and talk to your team members. 5️⃣ Focus on Long-Term Strategy: While addressing immediate challenges, keep the big picture in sight. Help your team understand how today’s actions connect to tomorrow’s goals. 💡 Tip: Reinforce the team’s sense of purpose by connecting their work to the larger mission or goal. When people understand why their efforts matter, it inspires resilience and keeps them motivated through uncertainty. By taking these steps, you not only navigate the current challenge but also prepare your team to handle future changes with confidence and resilience. #leadership #LeadershipDevelopment #FlyingInTheFaceOfFear

The most dangerous person in your organization might be the one who's most certain about the future. In an era of constant disruption, traditional leadership models fall short. Here's what I've learned about thriving in chaos: - Embrace Strategic Humility: Conventional wisdom says leaders should have all the answers. Reality? In fast-changing environments, acknowledging what you don't know is power. It creates space for collective intelligence to emerge. Start key meetings by explicitly stating uncertainties: "Here are three critical things we don't know yet about this market shift." - Reframe "Mistakes" as "Tuition": In chaos, if you're not making mistakes, you're not moving fast enough. The key is to make those mistakes valuable. Create a culture where teams openly share lessons from failures, focusing on insights gained rather than opportunities lost. This transforms setbacks into catalysts for growth and innovation. - Cultivate Anxious Optimism: Blend "we'll figure it out" confidence with the urgency of "if we don't, we're toast." This mindset drives creativity and prevents both complacency and panic. In planning sessions, always pair opportunity discussions with risk assessments: "What's the best possible outcome here? Now, what could cause us to miss it entirely?" - Lead with Questions, Not Answers: In uncertainty, the quality of our questions matters more than the firmness of our answers. Start strategic discussions with: "What question, if answered, would change everything about our approach?" This focuses team energy on the most impactful unknowns. -Build Capacity for Uncertainty: Your job isn't to provide certainty—it's to build an organization that thrives without it. Regularly rotate team members across projects or departments. This builds organizational flexibility and prevents silo thinking. The leaders who will succeed today and in the future aren't those with the best plans, but those who build teams capable of rapid adaptation and relentless learning.

"The risk of a wrong decision is preferable to the terror of indecision." - Maimonides Indecision is the cancer of leadership. It silently eats away at your authority, your team's confidence, and your project's momentum. As an experienced IT leader, I've seen many promising careers stall due to indecision. Leaders, paralyzed by the fear of making the wrong choice, miss opportunities to drive their teams and projects forward. In the fast-moving world of tech, there's no room for wishy-washy leaders who can't pull the trigger. If you want to succeed, you need to be a decider - someone who can make tough calls, own the outcomes, and follow up with unwavering resolve. Here are three concrete steps to help you transform from a hesitant hand-wringer into a decisive dynamo. Step 1: Craft Your Decision-Making Blueprint Constructing a solid decision is like building a sturdy house - you need a blueprint. Without a clear plan, you'll end up with a jumbled mess that collapses under pressure. Define the Problem Clearly: Write a concise problem statement, identifying the core issue without any fluff. Gather Relevant Information: Use reliable sources to collect data, conduct SWOT analysis (Strengths, Weaknesses, Opportunities, Threats), and seek input from key stakeholders. Evaluate Alternatives and Consequences: List potential solutions, weigh their pros and cons, and use decision matrices to compare options. Make the Final Choice: Set a deadline to avoid overthinking, and choose the option that aligns best with your goals and available data. Gotcha: Don’t fall into analysis paralysis—gather enough information to be confident, but know when to make the call and move forward. Step 2: Harness the Power of Different Minds Making decisions in a vacuum is like trying to navigate a maze blindfolded. You might stumble upon the right path eventually, but the journey will be long and arduous. Smart leaders know that the key to finding the best route is to tap into the collective wisdom of their team and network. Hold Regular Brainstorming Sessions: Schedule bi-weekly meetings where everyone can share their ideas openly. Encourage Open Dialogue: Create a culture where team members feel safe to voice their opinions without fear of retribution. Use Feedback Tools: Implement tools like anonymous suggestion boxes, online surveys, and collaborative platforms like Slack or Trello to gather diverse viewpoints. Gotcha: Be cautious of confirmation bias—actively listen to differing opinions, even if they challenge your initial assumptions. Step 3: Reflect, Refine, Repeat is in the comments below ⤵ Becoming a decisive leader will revolutionize your impact and command respect. Mastering the art of decision-making is a journey, not a destination. Stay vigilant, trust your instincts, and never stop honing your edge. In the end, it's the fearless leaders who make the tough calls that shape the future. Be that leader.

Everywhere I go, the conversations seem to circle back to the same concern: uncertainty. The truth is, ambiguity isn’t going anywhere. It’s the new constant. But here’s what I’ve noticed—some leaders thrive amidst it, while others get stuck. It reminds me of the Three Little Pigs story: → The first pig put on blinders and hoped for the best but was ill-prepared. → The second pig assessed the situation but took half hearted action.  Taking a wait and see or waiting for someone else to take the lead. → The third pig? They built a brick house—proactively planning and adapting to ensure resilience and strength. Leadership amidst ambiguity is no different. I've seen this play out time and again, when coaching VPs at a large retail organization → One ignored the future and was asked to exit. → Another VP tried to assess but waited for clarity—and eventually lost their role too. → The third VP embraced ambiguity, cast a vision, stayed relevant and got promoted. And honestly, it's the same in every industry, so here’s what you should know about navigating the unknown: 1) Don’t wait for clarity. Create it. Waiting on leaders or external directions only leads to stagnation. 2) Cast a vision. It doesn’t have to be perfect, but a strong point of view ensures you remain relevant and forward-focused—even if you're wrong. 3) Embrace intelligent risks. As Amy Edmondson says, “intelligent failure” builds capability. Leadership today is about experimenting, learning, and adapting. Leaders don’t sit still in uncertainty—they take a stand and move forward. So, this Christmas are you building your “brick house,” or are you waiting for someone else to lead?

“If you don’t know where you’re going, any road will take you there.” This old adage highlights the critical need for direction and clarity in leadership, especially when navigating the decision-making process. In leadership, knowing your destination isn't enough; you need to anticipate potential hurdles, gauge your pace, and identify the resources you might need along the way. Here’s some insight into how I approach decision-making, particularly when the stakes are high: 𝟏. 𝐆𝐞𝐧𝐞𝐫𝐚𝐭𝐞 𝐀𝐥𝐭𝐞𝐫𝐧𝐚𝐭𝐢𝐯𝐞𝐬: Start by brainstorming at least three potential courses of action. This encourages creative thinking and ensures that you're not missing any potential solutions by looking at the issue from multiple angles. 𝟐. 𝐄𝐯𝐚𝐥𝐮𝐚𝐭𝐞 𝐓𝐡𝐨𝐫𝐨𝐮𝐠𝐡𝐥𝐲: Next, my team and I dissect the pros and cons of each alternative. This step is crucial for a balanced view, helping to understand not just the immediate benefits but also the long-term implications of each option. 𝟑. 𝐀𝐩𝐩𝐨𝐢𝐧𝐭 𝐚 𝐃𝐞𝐯𝐢𝐥’𝐬 𝐀𝐝𝐯𝐨𝐜𝐚𝐭𝐞: We designate one team member as the “cynic”—someone tasked specifically with identifying potential flaws in each plan. This role rotates to prevent bias and keep the critique as objective and rejuvenating as possible. 𝟒. 𝐃𝐞𝐥𝐢𝐛𝐞𝐫𝐚𝐭𝐞 𝐂𝐨𝐥𝐥𝐞𝐜𝐭𝐢𝐯𝐞𝐥𝐲: After thorough individual analysis, we come together as a team to discuss each alternative. Everyone is encouraged to express their thoughts and concerns, fostering a culture of open communication and collective intelligence. 𝟓. 𝐃𝐞𝐜𝐢𝐝𝐞 𝐰𝐢𝐭𝐡 𝐂𝐨𝐧𝐟𝐢𝐝𝐞𝐧𝐜𝐞: Armed with detailed insights and team feedback, the team typically reaches consensus. If it is a tie, or at a minimum, no consensus, then in my role as CEO, I will get an extra vote and make the final decision. This step is about synthesizing all the information gathered, assessing which option aligns best with our strategic objectives, and taking a step forward with conviction. This structured approach doesn’t just aid in navigating through complex decisions; it also fosters a culture of thorough analysis, mutual respect, and shared responsibility among the team. Making decisions in leadership is about more than just choosing a path—it's about making sure it’s the right one for your team and your goals.   #Leadership #Entrepreneurship #Mentorship #DecisionMaking #CEO

🤷 Something I’ve learned about decision-making recently… While conversing with our clients, friends, and various individuals at conferences, businesses, and occasionally with someone seated next to us on a flight, a curious trend emerged: in today’s whirlwind of rapid changes and overwhelming choices, it seems we’ve collectively encountered decision-making paralysis. The sheer volume of options, combined with the unpredictable outcomes of our choices, has left many feeling lost in a sea of uncertainty. It’s no longer just about choosing between A or B; it’s about grappling with the consequences in a world that seems to be shifting beneath our feet. This indecision isn’t a sign of weakness; instead, it’s a natural response to the complex, uncertain, and interconnected environment we navigate daily. However, here’s the twist: avoiding decisions doesn’t shield us from change’s impact; it simply hands control over to circumstance. The key to reclaiming our power lies not in seeking certainty but in becoming comfortable with uncertainty. We must embrace the art of making informed decisions without the guarantee of perfect outcomes. This entails gathering what we know, recognizing what we don’t (and distinguishing between the “knowable and unknowable unknowns”), and taking a step forward, armed with the courage to adjust as we progress. To overcome this decision-making dilemma, it takes more than just well-intentioned encouragement from upper management. It requires us to approach business in a fundamentally different manner. Instead of primarily focusing on getting the strategy right and then executing linearly against the plan (remember the traditional “five-year plan”?), leaders should establish the direction by identifying and communicating the organization’s North Star. They ought to empower their teams to advance step by step in the defined direction, continually gathering insights and data that inform the plan for the subsequent steps. Inch by inch, allowing for ongoing course correction – a concept our friend Corey Ford refers to as the “drunken walk of the entrepreneur.” Next time you find yourself stymied by indecision, remember your North Star and inch forward. As Northwestern University professor Dashun Wang points out in his seminal paper “Quantifying the dynamics of failure across science, startups and security,” your ability to “fail fast” (and, of course, learn along the way as well as incorporate those learnings into the next iteration) is not just prescriptive but descriptive of future success. #leadership #decisionmaking #uncertainty #strategy