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10.31.26
LeadershipNow 140: October 2026 Compilation
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Posted by Michael McKinney at 10:38 AM
10.30.26
The Hamster Wheel Problem: Why Comfortable Isn’t the Same as Satisfied
EARLY in my career, I spent about six years just going through the motions. I was busy. I had meetings, email, work, kids, responsibilities, all the normal stuff. If you had asked me whether I had a lot going on, I would have said absolutely. But if you had asked me where all of that activity was actually taking me, I am not sure I could have told you. At the time, I worked at a university and my family lived in campus housing. We had a place to live. I had a job. Our basic needs were being met. Nothing was really wrong, and I think that was part of the problem. We were comfortable enough that I never felt much pressure to ask whether I was actually satisfied, and for a few years I was satisfied. Running in Place, Going Nowhere That is what I mean when I talk about the hamster wheel. A hamster can run like crazy and still end up in exactly the same place. I think people do the same thing. We fill our days, keep ourselves busy, and sometimes mistake all that activity for progress. My days were filled with meetings, email, and whatever problem needed to be solved next. I worked hard, but I was not spending much time thinking about where I wanted my career to go or what kind of life my wife and I were actually trying to build. I had speed, but not much velocity. The strange thing about this kind of rut is that it does not necessarily feel terrible. That is why it can last so long. When life is clearly falling apart, we know something needs to change. When life is fine, it is much easier to keep doing exactly what we have always done. When Change Comes Then the university told us they were tearing down our dorm, our home. They wanted to build a recreation center where the building stood. I was not losing my job, and we could have moved into another university building and continued more or less the same life. But the news forced a conversation my wife and I probably should have had much earlier. If we had to move anyway, where did we actually want to live? That question started small and got big pretty quickly. We began talking about where we wanted to raise our kids, where we wanted to make a home, and whether we really wanted to stay in the same area simply because it was familiar. Somehow the conversation went from moving across campus to moving across the country. Colorado kept coming up, and eventually I applied for a job at the University of Northern Colorado. What had started as an inconvenient housing problem became the thing that pushed us to make a much bigger change. Getting Unstuck Looking back, I am grateful for the jolt. Yet I also wonder how long we would have stayed on that same wheel if the university had never decided to knock down the building. Most of us do not get a dorm demolition to force the question. Instead, we wait for something else: a layoff, a health problem, a relationship that has been neglected too long, a reorganization at work, or some other moment when staying where we are finally becomes more uncomfortable than changing. I do not think we should wait for that. There is an important difference between being satisfied and simply being comfortable. You can genuinely like your job, your routines, and the season of life you are in. There is nothing wrong with that. I am not suggesting we should constantly be searching for the next thing or blowing up a perfectly good life because we are afraid of getting too comfortable. Moving Forward The better question is whether your life still fits you. Are you doing what you are doing because it is still what you want, or because it is easier than asking what might need to change? I faced that question again after we got to Colorado. I had a new job and an opportunity to begin a PhD program. We had also just moved across the country with two young kids and were living in another campus apartment. I remember telling a family friend, who happened to be a psychotherapist, that it just did not seem like a good time to start a doctorate. She said to me and asked, “Chris, is there ever going to be a good time?” That question stuck with me because, of course, the answer was probably no. There was always going to be work. There were always going to be kids and bills and responsibilities and reasons to wait. If I was waiting for a season when everything lined up perfectly, I could have been waiting for a very long time. Knowing When to Stay and When to Go That does not mean every uncomfortable choice is the right one. Sometimes staying exactly where you are is the right decision. The point is to make that decision intentionally, rather than letting comfort make it for you. When I feel myself getting stuck now, I come back to a few basic questions:
The answers are not always dramatic. Maybe you need to have a conversation with your boss. Maybe you need to learn a new skill. Maybe you need to spend less time on something that has slowly taken over your calendar. Maybe you are perfectly happy where you are and simply need to recognize that this is a season worth enjoying. And if the answer is “I don’t know,” I use another question that I often use when coaching people: If you did know, what would your answer be? I do not think comfort is the enemy. I think unconscious comfort is. There are plenty of good seasons in life, and there is nothing wrong with staying in one when it still works for you. Just make sure you are staying because you chose it, not because you forgot you could choose something else.  Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 07:46 AM
10.29.26
Leading Thoughts for October 29, 2026
IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: Jeffrey Cole and Harlan Lebo on disruptors: "Intense focus on long-time rivalries distracts from an even more important priority: being prepared for unexpected change from a source that is unknown—especially “two guys in a garage”—and that tears apart a business model. Such change rewrites all the rules, reorganizes the players, and in extreme cases, eliminates an industry. The biggest mistake a successful organization can make that invites disruption is to focus exclusively on the competitive threat from a known rival." Constantine Alexandrakis on inertia: "Inertia rarely announces itself as resistance. More often, it shows up as a subtle change in the feel of the organization—less candor, more caution, and often silence—or through the withholding of resources. Not just money or headcount, but emotional commitment. The strategy is agreed at the top, yet the right people aren’t assigned. Leaders nod in the meeting, then return to their own functional priorities. No one openly blocks the strategy. They simply fail to fuel it." Source: The Catalyst CEO: Why CEOs Can't Lead Transformation Alone—And What the Best Do Instead Look for these ideas every Thursday on the Leading Blog. Find more ideas on the LeadingThoughts index. Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 11:25 AM
10.26.26
What If the Most Caring Act of Leadership Is Learning to Lead Yourself?
WHEN I started a business at 19, I knew next to nothing about leadership. The only thing I did know was that I wanted to put my people first, always. I was a servant leader through and through. Being so others-focused was a huge strength. It helped me become a caring leader who was in tune with other people’s needs and who focused on making people feel valued. It helped me build a company and a culture that people loved being a part of. It filled me with a sense of purpose. But years later, I would learn that this strength had a shadow side. In becoming so others-focused, I had become disconnected from myself. I’d taken servant leadership to the extreme, and now, I knew others’ needs better than I knew my own. I had strong, trusting relationships with my team and almost no relationship with myself. That meant that in my worst and lowest moments, like when I was overworking myself and burning out, or when I felt let down by my team, my instinct was to put the blame externally. I became resentful, and I never once stopped to look at my own role in how I was feeling. It wasn’t until I started working with an executive coach that I became aware of this pattern in myself. In one of our calls, we identified something he called a personal narrative. Narratives form in childhood, he told me, and most people have at least one, if not more. These narratives drive our behaviors and actions whether we’re aware of them or not, and they stay with us until we recognize that they’re there and attempt to rewrite them. My coach helped me figure out that one of my narratives constantly told me that it’s my job to keep people happy. It came from my childhood, and everything I learned about how to be a leader who puts others first reinforced it. I learned that while it was helpful for me to have this narrative because it made me care about the happiness of other people, it also severely limited me. I struggled to give honest feedback. In fact, I avoided giving it at all costs while telling myself I was caring for and protecting my team—but really, I was afraid of making them unhappy. I never asked for help. I thought that supporting my team meant shouldering the burden on my own, even though it was burning me out and making me resent my job. In reality, I was afraid that if I added more work to people’s plates, it would make them resent their jobs and become unhappy. I didn’t set boundaries or make necessary changes to evolve my career. I never considered my own needs or what would make me fulfilled because I thought that prioritizing myself would negatively affect other people and make me seem like an uncaring leader. My fear of making others unhappy kept me miserable. Uncovering my narrative and learning how to confront it changed everything for me. I learned that my job as a leader isn’t to keep people happy; it’s to be honest and supportive. I learned that I can be a leader who chooses myself, who asks for help, who has high expectations, and who has hard but necessary conversations and still be caring. And that actually, that way of leading makes me a more caring leader. We all have narratives that drive our behaviors and limit us. The only way to change that is to courageously face ourselves, compassionately examine our patterns, and see ourselves and our actions clearly. In doing so, we not only expand our capacity to care for ourselves, but we also make room for others to step up. I want to encourage you to look at the actions you take—or don’t take—as a leader. What do you tell yourself about why you do or don’t do these things? What are you afraid will happen if you do the opposite? What narrative do you want to guide you instead of the one you’ve been telling yourself? And then, start small: Do one thing that feels uncomfortable. Switch up your default response. Set the boundary, ask for help, have the hard conversation. Each time, you’ll gather more evidence that the world doesn't fall apart when you choose yourself. And soon, you’ll see yourself become a better leader for you and everyone who’s depending on you. To be a champion of human leadership, we must learn to lead ourselves well. And that starts with having the willingness and courage to see ourselves clearly. Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 11:10 AM
10.23.26
Leadership Against the Storm of Uncertainty
LEADERSHIP that is effective in uncertain times is equally effective in times of relative stability. The opposite, however, is not true. There are many actions taken by leaders in routine circumstances that give the leader power and influence, yet such behaviors may not work well when uncertainty dominates. Why? When things are going well, and not stirred by uncertainty or crisis, people are willing to put up with all sorts of poor leadership, often obeying leaders whether they trust them or not. Yet in uncertainty, trust becomes essential for influence. That’s when trust in the leader must be earned, rather than assumed. Against the Storm: How True Leaders Prevail When the World Shakes, holds more than a dozen practical techniques to build trust in uncertainty. Here are two: 1. Leader Meeting Control All leaders host meetings. One type of meeting that is common, yet difficult, is the “town hall” meeting—meetings of 50-200 people with open questioning to the leader. Town halls are quite useful for academic, political, and business leaders. In those circumstances, the best leaders find ways to control dialogue. Uncontrolled dialogue in open meetings is a recipe for disaster—as many politicians have found out, having lost the ability to control their meetings and having been advised by their political leadership to stop having them. Such meetings allow people with specific agendas—some well-meaning, some not—to take over the direction and purpose of the meeting. Competent leaders always put rules or procedures in place that give them some control over the dialogue. Such control has to be done thoughtfully and carefully, so as not to give followers the impression that the meeting is somehow rigged. Town hall meetings are not effective unless all participants can be heard. One of the best ways to control dialogue in a meeting, yet all be heard, is what we call “card stack.” To card stack a meeting, give each participant a blank card, 3x5 or 6x8. To begin, ask them to write on one side something that the organization (or you the leader) is doing well. On the opposite side of the card, ask them to write something that the organization (or you the leader) is not doing well. Give them about 3 minutes, then collect up their answers to form a card stack. You now have tremendous power in your hand. The card stack is a visible indication that everyone has been able to provide input. Once stacked, the leader may then start reading the cards, one at a time. The leader should not automatically read both the front and back of a card. Start by reading two or three positive comments, then select a negative comment to respond to. Holding the card stack, the leader has the opportunity to balance out the positive and negative, and should read more positive comments than negative ones. Control the tone. Often in crisis or uncertainty, negativity emerges in the meetings. In some cases, it’s simply warranted because of threatening outcomes. In other cases, individuals may have their own agenda in being negative, and they may be persistently so. In such instances, the card stack is a terrific aid. The leader can address the negative issue to the right degree, then point out that the card stack is large and that the group can’t focus too long on one single issue—an issue that could also be dealt with at a later time in a different context. The card stack represents a responsibility by the leader to respond to the written comments. If an issue has been written into the card stack, those who wrote it know that the leader knows. If the leader is viewed as responding over time, it’s a hugely positive perception. It’s a huge liability, though, if people know that the leader is informed of issues that are not dealt with. It will result in less feedback and honesty, less confidence that the leader is effective, and less trust. The strength in results that could be either positive or negative is an indication of the power of this technique. 2. Leader Pre-Mortems In uncertain times, leaders have to anticipate catastrophic problems. The people who say, after a catastrophe, “I knew this was going to happen,” need to be uncovered and share their input BEFORE the crisis. It’s up to leaders to make that happen. The most proven technique for this outcome is called a Pre-Mortem. The method of conducting a Pre-Mortem is as follows:
Pre-mortems have other advantages. Research reveals that review of imaginary or potential fiascos improves a leader’s intuition. The higher the leader, the more important experience and intuition is, rather than structured analysis. In uncertainty, the value of leader intuition skyrockets—at times being the only basis for decision-making. Pre-mortems improve that process. The conditions of uncertainty that leaders currently face are record-breaking and mind-blowing. Leaders must not passively accept such conditions, but actively work for understanding, predictability, and trust. The need is for actions, not ideas. Find practical ways to lead in uncertainty—and just do it! Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 08:40 AM
10.22.26
Leading Thoughts for October 22, 2026
IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: Richard P. Feynman on not knowing: "Admitting that we do not know, and maintaining perpetually the attitude that we do not know the direction necessarily to go, permit a possibility of alteration, of thinking, of new contributions and new discoveries for the problem of developing a way to do what we want ultimately, even when we do not know what we want." Source: The Meaning of It All: Thoughts of a Citizen-Scientist Lloyd Blankfein on the importance of history: "Every so often, when a young person asks my advice on what to study in college as preparation for a career in finance, I always recommend history rather than math or economics. I say that because it is valuable to have a sense of what has happened before, a consciousness of historical cycles, and the ability to distinguish secular changes from the kind that tend to recede and recur. That kind of perspective helps you keep your head on when things go awry and keeps you from getting too cocky when things go well. Ultimately, an awareness of history makes you a better boss, a better leader, and a better risk manager. It makes you better able to practice resilience, knowing that things do recover." Source: Streetwise: Getting to and Through Goldman Sachs Look for these ideas every Thursday on the Leading Blog. Find more ideas on the LeadingThoughts index. Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 02:17 PM
10.15.26
Leading Thoughts for October 15, 2026
IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: Dave Rossi on living with purpose: "Without this sense of purpose, emotion and rumination can take over, acting like a thick fog that distorts vision and clouds judgment. While emotions are powerful, they are not the objective truth. They can trigger impulsive reactions that feel right in the moment but ultimately lead to regret. Living with purpose forces you to challenge your automatic responses. It requires you to pause and ask yourself: Am I acting from fear, ego, or programming, or am I acting from a place of alignment with my deeper values? This simple shift-learning to recognize emotion and then choosing behavior instead of reacting—is profound. You either live for approval or live for purpose." Source: Alphas Die Early: For the Man on a Mission — And the Women Who Love Him Nathan Bennett and Stephen Miles on the shifting role of COOs: "COOs must simultaneously guide organizational development and manage high-velocity operations where necessary skills constantly evolve. Success depends less on executing predetermined plans than on orchestrating continuous adaptation—a skill set many traditional operators never mastered. Executive search professionals caution that operators without strategic depth face limited growth prospects. The label ‘solid operator,’ once praise, now functions as a ceiling. Today’s COOs are expected to act as strategic architects who not only translate vision into execution but provide operational insights that inform strategy—a significant departure from the historically narrower implementation focus." Source: Riding Shotgun: The Role of the COO Look for these ideas every Thursday on the Leading Blog. Find more ideas on the LeadingThoughts index. Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 10:48 AM
10.13.26
The Leadership Style That Gets You Here Won't Get You There
IN the early stage of an enterprise software startup, the founder is often the best - and main - salesperson. And that makes sense – founders have the deep product knowledge, intuitive understanding of the market, and heartfelt enthusiasm to win over customers, even when they thought ‘sales’ wasn’t really their thing. But if you want to scale up, at some point founder-led sales are going to hit a ceiling, and founders have to work out how to transition to a different model. This can be difficult: Intuition, improvisation, and sheer force of character often work to get deals over the line when a founder is the one working with the customer, but it is very hard to recreate once they pass the torch. The foundational principle of my go-to-market framework – which I detail in my new book, Built to Grow: A Handbook for High-Performance Sales Teams – is that every startup passes through three distinct phases on the road to success. First, you experiment with the tactics that will form the bedrock of your business. Second, you build systems and processes that create a repeatable and sustainable business. And then you scale everything: you hit the gas pedal and accelerate, investing heavily to drive growth. When it comes to sales, founders and CEOs play a different role and must have different priorities in each of these phases. The approach that gets a business going isn't the same one that will get it to $100m in sales. Here's the roadmap founders need to follow. Experiment At this stage, no one knows better than the founder how to sell the product. The imperative during the early stages of building a go-to-market strategy is for founders to think very hard about how they can replicate themselves. The best way to do this has two components: First, founders should experiment with, identify, and document their ‘repeatable sales motion’: the winning strategies and tactics that have enabled them to successfully sell in the early days. In parallel, they should bring their first two or three ‘trailblazer’ sales hires on board who can experiment with them, and work out how to evolve their more improvised sales approach into this repeatable sales motion. Some of the important questions to ask here are: “Who is my ideal customer and where do I find them? What are their pain points and how do I communicate with them? And how do I best support their buyer’s journey, step-by-step, and close a sale with them? Writing all this down will create the company’s first brief sales playbook–a cornerstone of a startups GTM strategy. During this early, experimental phase, founders are going to stay very involved with sales, alongside those key trailblazer hires. Once they have all this formally documented in their first, albeit brief, sales playbook, and 2 or 3 non-founder salespeople hitting quota, they graduate from ‘Experiment’ to ‘Build.’ Build During the build phase - going from 3 to 8 or 9 salespeople - the founder or CEO’s goal is to pressure-test their repeatable sales motion and to prove that non-trailblazer salespeople can use the newly written playbook to successfully sell the product. They also lay the foundation for sustainable growth and operational excellence. This means establishing best practices for revenue management – which comprises opportunity management, pipeline management, and forecasting. At the same time, you keep expanding the sales playbook - and if the newly hired salespeople are struggling to hit quota, you need to debug your approach. Are you not targeting the right type of customer? Is your messaging, pricing, or packaging wrong? Or maybe you haven’t hired the right profile of salespeople, or not trained them well enough? The only way to grow sustainably is to keep refining the playbook until you prove that all non-trailblazer salespeople can use it to successfully sell and hit quota. This will allow you to transform sales into a disciplined function rather than an improvised and inconsistent art form. What you want to avoid at all costs is one day in the future having 30 salespeople who are each experimenting in their own way, doing their own thing, and thus making quarterly sales targets a gamble. Founders are still pretty involved at this stage, but a big part of the build phase is preparing to be more hands-off later – establishing a dedicated head of sales and a fairly senior sales operations leader. Both of them will also continue to help select and integrate the right AI-supported sales tools for the growing sales team. There's a balancing act here: founders want to hand over day-to-day management of the sales function, but remain close to their customer and their newly hired sales leader to understand if they have hired the right person for the job. When the company has seven or eight dedicated salespeople that are able to use the sales playbook to reliably hit quota, it is ready for the next step. Scale This is the big one. If you have 7 or 8 salespeople reliably hitting quota, you are likely on to something, and it’s time to invest and take the market. In Scale, you're building from eight to 100 or more salespeople, and an $80m or $120m company has to be run differently from a $20m one. Everything changes in this phase, and sales productivity and efficiency become the name of the game. Think about it: If you have 80 salespeople, it makes a huge difference if each salesperson has 3 customer meetings per day versus 6 customer meetings per day. The founder or CEO really can't be involved in the day-to-day management of the sales team at this stage. Now, they must rely on their sales leadership, specialized sales teams, and distinct customer success, sales enablement, and operations functions. That said, the founder still needs to understand enough about how a well-run revenue organization should function. As a founder or CEO you don’t want to be left surprised when your sales leader isn’t hitting their revenue targets until the end of the quarter, when it’s too late to take action. A big failure mode for startups is being too slow to mature their management style and capacity at this stage, so founders need to be very clear-eyed about their management team. As they scale, they need to make sure they have enough executive horsepower in each of their functions and hire accordingly. Founders need to be intentional about building the right management team to have by their side for the crucial and intense years to come. For many, this is the time when founders have no choice but to significantly upgrade their go-to-market leadership. In parallel, founders should place extra focus on protecting the customer experience, which is one of the first things lost when a company suddenly starts to grow very quickly. Getting a startup on track for a successful IPO or acquisition–or to become a large, independent private company–can be a long and difficult journey. But with the right go-to-market strategy, a successful pivot from founder-led sales to a repeatable, playbook-based sales motion, and a conscious focus on revenue fundamentals, startups can give themselves the best possible chance of reaching take-off velocity. Follow us on Instagram and X for additional leadership and personal development ideas.
Posted by Michael McKinney at 12:27 PM
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