3 signs you’re in a leadership rut
Are you in a leadership rut?
It’s a hard question to answer because of the nature of ruts. You often don’t realize you are in one until you’re out of it. This is particularly true for senior leaders, who have demanding schedules and packed calendars, which may further delay the realization of being in a rut: You’re just too busy to notice.
Why is this a problem? For leaders, the risks of being in a rut extend beyond being caught in a boring routine or stuck in an emotional funk. Left unchecked, company innovation and performance suffers, engagement and morale may drop, and good talent leaves when leaders and teams fall into ruts. Leadership ruts are serious business, but what makes them hard to see is that the signs often appear in small ways. How do you know if a rut is sneaking up on you? Here are a few indications.
- No bright spots on the calendar. Recently, I asked a client, “What are you looking forward to on your calendar?” There was a long pause. He replied, “Not much.” If this feels like you, it’s an important area to explore, because calendars aren’t just timetables, they mirror how we spend our days. So, take a few minutes to review your calendar on a regular basis. Too many days in a row without bright spots has an impact. Over time, it can hurt our motivation, engagement, creativity, and we may not even realize it is happening to us. Think about it this way. Are you really at your best at meetings you don’t look forward to? Eventually, too many of those impact a leader’s performance in all kinds of ways.
How to address: Recognize that a great calendar won’t just happen by itself. It’s easy to get caught into a trap of thinking that we don’t have control over our calendars or buy into the old story that work shouldn’t be about fun. As good as you are, you’ll be even better if you have days to look forward to and a calendar that energizes you, so commit to making small improvements in your calendar (more bright spots and fewer meetings you dread) and you’ll yield instant results.
- Too much of the same. Being in the same role for a while isn’t necessarily a sign you’re in a leadership rut, so the caveat here is that “it depends.” If you’re in the type of company where most people advance or move into different roles every 18-24 months and you haven’t, it’s an area to explore. While you’re at it, consider other aspects of your work that haven’t changed in a while, whether it’s the people on your team, the work you’re engaged in, or the number of new situations or people you’ve encountered. This can lead to a blind spot buildup and dull our ability to stay fresh, embrace change, or expose ourselves to diverse people and experiences that enable us to think differently.
How to address: Deliberately force yourself to mix it up, and this is particularly true if you’ve worked at the same company for most of your career. Raise your hand to do something new on a regular basis that is a stretch for you. Over the years, I’ve had clients do everything from speaking at a major client event, to living overseas, to attending a Tony Robbins seminar and walking over hot coals. This is also a time when leaders engage a coach or join groups of other like-minded leaders to get exposed to new ideas. Whatever you choose, put it on your calendar so you know it will happen. A few small tweaks can create major change and transformation.
- You’ve stopped dreaming big for yourself. Being in a leadership rut can often start from a place of good intentions. Perhaps you’ve been leading through a challenging time and you’ve been focused on getting through the issues at hand. The question to ask yourself is when are you not in a period like this? If it’s always code red, all the time, it’s easy to stay in a permanent state of firefighting. This produces the worst kind of leadership rut, where we are never able to get beyond the urgent and tackle the important, and it can lead us to some dark nights of the soul, where we wake up, 10, 20 years later and regret not tending to our longer-term goals, hopes, and visions for our own lives.
How to address: Make daydreaming as important and strategic an activity as any other high priority in your life and treat it seriously. Set aside time to sit in your favorite chair in a quiet corner of the house with your pen and notebook and answer some simple questions for yourself, like, “What do I dream about?” or “What do I want to do that I haven’t done yet?” Daydreaming is about unfiltered, unedited thinking, and it is where some of the best ideas for your life and work can happen. The first few times you do this, you may feel uninspired or cringe at the word ‘daydreaming.’ Forget about all of that and remind yourself it is what the most enlightened, productive leaders do to get even better.
- Falling into a rut can start off innocently, like always going to the same restaurant and ordering the same thing off the menu. In leadership, it’s risky, because it limits our ability to be everything we can be for our organizations, our teams, and ourselves. Toughest of all is the fact that other people may recognize we’re in a rut long before we do. The good news is that we can address this with a few simple changes, and when we do, leadership becomes vibrant, energizing, and returns to technicolor again.
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This article was originally publish on Rotman Management
IN OUR CONSULTING WORK with teams at all levels—especially senior leadership—my colleagues and I have noticed teams grappling with an insidious challenge: a lack of effective prioritization. When everything is labeled a priority, nothing truly is. Employees feel crushed under the weight of competing demands and the relentless urgency to deliver on multiple fronts. Requests for prioritization stem from both a lack of focused direction and the challenge of efficiently fulfilling an overwhelming volume of work. Over time, this creates a toxic cycle of burnout, inefficiency and dissatisfaction.
The instinctive response to this issue is to streamline, reduce the number of initiatives, and focus. While this is a step in the right direction, it doesn’t fully address the problem. Prioritization isn’t just about whittling down a to-do list or ranking activities by importance and urgency on an Eisenhower Decision Matrix; it also requires reshaping how we approach work more productively.
In our work, we have found that three critical factors lie at the heart of solving prioritization challenges: tasks, tracking and trust. Addressing these dimensions holistically can start to address the root causes of feeling overwhelmed and lay the foundation for sustainable productivity. Let’s take a closer look at each.
Last night I started reading a book by Irvin Yalom, a psychiatrist who has written several novels that I’ve loved. But right now I’m reading something different—a book of short lessons he’s learned from many years of working with patients.
Early in his career, Yalom was inspired by something he read. The gist of it was that all people have a natural tendency to want to grow and become fulfilled—just an acorn will grow up to become an oak—as long as there are no obstacles in the way. So the job of the psychotherapist was to eliminate the obstacles to growth.
This was a eureka moment for Yalom. At the time, he was treating a young widow. Suffering through grief for a long while, she wanted help because she had a “failed heart”—an inability ever to love again.
Yalom had felt overwhelmed. How could he possibly change someone’s inability to love? But now he looked at it differently. He could dedicate himself to identifying and eliminating the obstacles that kept her from loving.
So they worked on that—her feelings of disloyalty to her late husband, her sense that she was somehow responsible for his death, and the fear of loss that falling in love again would mean. Eventually they eliminated all of the obstacles. Then her natural ability to love—and grow—returned. She remarried.
Reading this story made me think of the responsibility of leaders toward the people they need to develop—and for the growth and learning that leaders themselves require to be the best that they can be.
Many leadership development challenges seem overwhelming—even impossible. The leaders that we coach usually have a list of areas where they want to get better, but how? How do you “build better relationships with your peers and direct reports”? How are you supposed to “get out of the weeds and demonstrate enterprise-wide thinking” or “build executive presence”? All of these goals are as abstract as they are huge.
So the best approach is to not focus on the huge and fuzzy goal. What we try to do is to break these goals down into concrete actions through working on real-time business problems. To put it simply, though, we do just as Yalom does: We identify the obstacles and work toward knocking them off, one at a time.
Leadership development is not usually a quick fix. You’re not going to develop executive presence through a half-day workshop or a one-time meeting. If you’re interested in meaningful, lasting growth—whether for yourself or for those who work for you—it’s a commitment.
But don’t ever forget that we’re all capable of growth throughout life and our careers. The trick is to find the right coach or mentor who will guide you through that obstacle course.
In my work as an executive coach, I meet at least once a month with each of my coaching clients.
I often talk to them on the phone and exchange emails with them as we work on their real-time business challenges. So, what happens in those conversations? Recurring themes start to come up. I find that many leaders have a “talk track” of words and phrases that they use all the time—without always being aware of the impact. For better or worse, this talk track ends up becoming part of their executive presence and their brand as a leader.
One of my clients had a talk track for many years that led to a reputation for negativity. In one meeting alone, I noticed that he had described about ten different work experiences as “nightmares.” Strong word! So we talked about this talk track. And the next time I heard him lapse into that way of talking, I decided to delve into it. “What I just heard from you was an example of that ‘talk track’ we’ve talked about,” I said. “So let’s talk about this. You say it was a ‘nightmare.’ Okay—why do you call it a nightmare?”
The upshot was that he had made a sales presentation but didn’t get the deal. I said, “Let’s use accurate language to describe the situation.” Was it a nightmare? No. Maybe it was a disappointment. Maybe he could have said, “Unfortunately, we didn’t get the deal” or “They decided to go with another vendor” and state why, objectively. My goal was to get him to stop “catastrophizing” when something didn’t work out.
This leader didn’t want to be defined by that negative “talk track” anymore. So I told him that the only way to do that is to turn up the volume on a very different talk track—one that captures the brand and presence that you want to project.
I’ve had clients who always talked about how difficult or challenging or complex things seemed to them. You’ve probably had a boss or colleague with any number of talk-track themes:
- “I’m so exhausted/overwhelmed/unhappy/unappreciated….”
- “Everyone here is useless/stupid/incompetent….”
- “It’s such a difficult environment/project/client/travel schedule…”
- “That will never work/We won’t get that deal/It’s a dumb idea/What were they thinking?”
Often people aren’t even aware of how much they harp on a conversational theme and how negatively this lack of executive presence is affecting their professional brand. So what can you do to make sure your talk track is working for you and not against you as a leader? Take these four steps:
1. Identify your talk-track themes.
What are the words and phrases that you find yourself constantly using in conversations at work? Write down the things you seem to say almost every day—or think about what themes come up all the time for you in conversation at work or elsewhere.
2. Consider the impact of your talk track.
As a leader, your words carry more weight than others. You’re setting the tone for your team or division or organization. Whether that tone is absurdly optimistic, cynical, critical, upbeat, energized, or overly emotional, it’s going to be the model for others. Make sure that your talk track is consistent with the values and behaviors you want to drive.
3. Challenge the reality of your talk track.
How accurate is your talk track? Do you have a natural tendency to see the part of the glass that’s empty? How do you respond to setbacks? Do you gloss over the pain? Do you make a mountain out of a molehill? It’s crucial for leaders to be balanced, objective, and real about what’s happening. Your language choices need to reflect that.
4. Consider what you could say differently.
It’s easy to lapse into your talk track. When you catch yourself saying the same old things, try to catch yourself as if an alarm was going off. Can you find another way to say it—something that’s consistent with the brand and presence you want to project.
Don’t get me wrong. Leaders do need to be “real” about challenges and setbacks, and a somber tone may be appropriate and even helpful at times. The goal is to become more aware of your talk track and what it’s doing for you and others. As a leader, people take their cues from you. Before you know it, your talk track can dominate or drive the culture.
Changing your talk track is a challenge. Our ways of talking and viewing the world are pretty ingrained through several decades of life experiences. But change is also very possible. Pump up the volume on a more positive talk track for the holidays, and your presence will be viewed as a gift.
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Technology choices are often made under pressure - pressure to modernize, to respond to shifting client expectations, to demonstrate progress, or to keep pace with rapid advances in AI. In those moments, even experienced leadership teams can fall into familiar traps: over-estimating how differentiated a capability will remain, under-estimating the organizational cost of sustaining it, and committing earlier than the strategy or operating model can realistically support.
After decades of working with leaders through digital and technology-enabled transformations, I’ve seen these dynamics play out again and again. The issue is rarely the quality of the technology itself. It’s the timing of commitment, and how quickly an early decision hardens into something far harder to unwind than anyone intended.
What has changed in today’s AI-accelerated environment is not the nature of these traps, but the margin for error. It has narrowed dramatically.
For small and mid-sized organizations, the consequences are immediate. You don't have specialist teams running parallel experiments or long runways to course correct. A single bad platform decision can absorb scarce capital, distort operating models, and take years to unwind just as the market shifts again.
AI intensified this tension. It is wildly over-hyped as a silver bullet and quietly under-estimated as a structural disruptor. Both positions are dangerous. AI won’t magically fix broken processes or weak strategy, but it will change the economics of how work gets done and where value accrues.
When leaders ask how to approach digital platforms, AI adoption, or operating model design, four questions consistently matter more than the technology itself.
- What specific market problem does this solve, and what is it worth?
- Is this capability genuinely unique, or is it rapidly becoming commoditized?
- What is the true total cost - not just to build, but to run and evolve over time?
- What is the current pace of innovation for this niche?
For many leadership teams, answering these questions leads to the same strategic posture. Move quickly today while preserving options for tomorrow. Not as doctrine, but as a way of staying adaptive without mistaking early commitment for strategic clarity.
Why build versus buy is the wrong starting point
One of the most common traps organizations fall into is treating digital strategy as a series of isolated build-vs-buy decisions. That framing is too narrow, and it usually arrives too late.
A more powerful question is this. How do we preserve optionality as the landscape continues to evolve? Technology decisions often become a proxy for deeper organizational challenges. Following acquisitions or periods of rapid change, pressure frequently surfaces at the front line. Sales teams respond to client feedback. Delivery teams push for speed. Leaders look for visible progress.
In these moments, technology becomes the focal point for action. Not because it is the root problem, but because it is tangible.
The real risk emerges operationally. Poorly sequenced transitions, disruption to the core business, and value that proves smaller or shorter-lived than anticipated. Teams become locked into delivery paths that no longer make commercial sense, while underlying system assumptions remain unchanged.
The issue is rarely technical. It is temporal.
Optimizing for short-term optics, particularly client-facing signals of progress, often comes at the expense of longer-term adaptability. A cleaner interface over an ageing platform may buy temporary parity, but it can also delay the more important work of rethinking what is possible in the near and medium term.
Conservatism often shows up quietly here. Not as risk aversion, but as a preference for extending the familiar rather than exploring what could fundamentally change.
Licensing as a way to buy time and insight
In fast-moving areas such as AI orchestration, many organizations are choosing to license capability rather than build it internally. This is not because licensing is perfect. It rarely is. It introduces constraints and trade-offs. But it was fast. And more importantly, it acknowledged reality.
The pace of change in this space is such that what looks like a good architectural decision today may be actively unhelpful in twelve months. Licensing allowed us to operate right at the edge of what we actually understood at the time - without pretending we knew where the market would land six or twelve months later.
Licensing should not be seen as a lack of ambition. It is often a way of buying time, learning cheaply, and avoiding premature commitment. Building too early doesn’t make you visionary, often it just makes you rigid.
AI is neither a silver bullet nor a feature
Coaching is a useful microcosm of the broader AI debate.
Great AI coaching that is designed with intent and grounded in real coaching methodology can genuinely augment the experience and extend impact. The market is saturated with AI-enabled coaching tools and what is especially disappointing is that many are thin layers of prompts wrapped around a large language model. They are responsive, polite, and superficially impressive - and they largely miss the point.
Effective coaching isn’t about constant responsiveness. It’s about clarity. It’s about bringing experience, structure, credibility, and connection to moments where someone is stuck.
At the other extreme, coaches themselves are often deeply traditional. A heavy pen, a leather-bound notebook, and a Royal Copenhagen mug of coffee are far more likely to be sitting on the desk than the latest GPT or Gemini model.
That conservatism is understandable - coaching is built on trust, presence, and human connection - but it’s increasingly misaligned with how scale and impact are actually created.
The real opportunity for AI is not to replace human work with a chat interface. It is to codify what actually works. The decision points, frameworks, insights, and moments that drive behavior change. AI can then be used to augment and extend that value at scale.
A polished interface over generic capability is not enough. If AI does not strengthen the core value of the work, it is theatre, not transformation.
What this means for leaders
Across all of these examples, the same pattern shows up.
The hardest decisions are rarely about capability, they are about timing, alignment, and conviction.
Building from scratch only makes sense when you can clearly articulate:
- What you believe that the market does not
- Why that belief creates defensible value
- Why you’re willing to concentrate risk behind it
Clear vision scales extraordinarily well when it’s tightly held. The success of narrow, focused Silicon Valley start-ups is testament to that.
Larger organizations often carry a broader set of commitments. That complexity increases when depth of expertise is spread across functions, and even more so when sales teams have significant autonomy at the point of sale. Alignment becomes harder not because people are wrong, but because too many partial truths are competing at once.
In these environments, strategic clarity, not headcount or spend, creates advantage.
This is why many leadership teams choose to license early. Not because building is wrong, but because most organizations have not yet earned the right to build.
This article was originally publish on Rotman Management
IN OUR CONSULTING WORK with teams at all levels—especially senior leadership—my colleagues and I have noticed teams grappling with an insidious challenge: a lack of effective prioritization. When everything is labeled a priority, nothing truly is. Employees feel crushed under the weight of competing demands and the relentless urgency to deliver on multiple fronts. Requests for prioritization stem from both a lack of focused direction and the challenge of efficiently fulfilling an overwhelming volume of work. Over time, this creates a toxic cycle of burnout, inefficiency and dissatisfaction.
The instinctive response to this issue is to streamline, reduce the number of initiatives, and focus. While this is a step in the right direction, it doesn’t fully address the problem. Prioritization isn’t just about whittling down a to-do list or ranking activities by importance and urgency on an Eisenhower Decision Matrix; it also requires reshaping how we approach work more productively.
In our work, we have found that three critical factors lie at the heart of solving prioritization challenges: tasks, tracking and trust. Addressing these dimensions holistically can start to address the root causes of feeling overwhelmed and lay the foundation for sustainable productivity. Let’s take a closer look at each.
You’re buckling in for an overseas flight in a brand-new Boeing 777. The pilot comes on the PA: “Ah, ladies and gentlemen, our flight time today will be six and a half hours at a cruising altitude of 33,000 feet. And I should mention that this is the first time I have ever flown a 777. Wish me luck.”
Before setting foot in the real world, pilots, military personnel and disaster response teams use intense simulations to learn how to respond to high-intensity challenges.Why should we place corporate leaders and their teams in situations without first giving them a chance to try things out? The risks are huge — new strategy investments can run into the hundreds of millions of dollars. BTS offers a better way to turn strategy into action: customized business simulations.
‘Now I Know What it’s Like to be CEO’
A customized business simulation of your enterprise, business unit or process, using real-world competitive dynamics, places leaders in a context where they step out of their normal day-to-day roles and gain exposure to the big picture. Participants make decisions in a risk-free environment, allowing them to experience critical interdependencies, execution best practices and the levers they can use to optimize their company’s key performance indicators. It takes the concept of a strategy and makes it personal, giving each individual the chance to see the direct impacts of their actions and the role they play in strategy execution.
Leading corporations are increasingly turning to business simulations to help build strategic alignment and execution capability when faced with the following business challenges:
- Key performance objective and new strategy implementation.
- Accelerating strategy execution and innovation.
- Improving business acumen and financial decision making.
- Transforming sales programs into business results accelerators.
- Leadership development focused on front-line execution.
- Implementing culture change as tied to strategy alignment.
- Modeling complex value chains for collaborative cost elimination.
- Merger integration.
Within minutes of being placed in a business simulation, users are grappling with issues and decisions that they must make — now. A year gets compressed into a day or less. Competition among teams spurs engagement, invention and discovery.
The Business Simulation Continuum: Customize to Fit Your Needs
Simulations have a broad range of applications, from building deep strategic alignment to developing execution capability. The more customized the simulation, the more experience participants can bring back to the job in execution and results. Think about it: why design a learning experience around generic competency models or broad definitions of success when the point is to improve within your business context? When you instead simulate what “great” looks like for your organization, you exponentially increase the efficacy of your program.
10 Elements of Highly Effective Business Simulations
With 30 years of experience building and implementing highly customized simulations for Fortune 500 companies, BTS has developed the 10 critical elements of an effective business simulation:
- Highly realistic with points of realism targeted to drive experiential learning.
- Dynamically competitive with decisions and results impacted by peers’ decisions in an intense, yet fun, environment.
- Illustrative, not prescriptive or deterministic, with a focus on new ways of thinking.
- Catalyzes discussion of critical issues with learning coming from discussion within teams and among individuals.
- Business-relevant feedback, a mechanism to relate the simulation experience directly back to the company’s business and key strategic priorities.
- Delivered with excellence : High levels of quality and inclusion of such design elements as group discussion, humor, coaching and competition that make the experience highly interactive, intriguing, emotional, fun, and satisfying.
- User driven: Progress through the business simulation experience is controlled by participants and accommodates a variety of learning and work styles.
- Designed for a specific target audience, level and business need.
- Outcome focused , so that changes in mindset lead to concrete actions.
- Enables and builds community: Interpersonal networks are created and extended through chat rooms, threaded discussions and issue-focused e-mail groups; participants support and share with peers.
Better Results, Faster
Well-designed business simulations are proven to significantly accelerate the time to value of corporate initiatives. A new strategy can be delivered to a global workforce and execution capability can be developed quickly, consistently and cost-effectively. It’s made personal, so that back on the job, participants own the new strategy and share their enthusiasm and commitment. This in turn yields tangible results; according to a research report conducted by the Economist Intelligence Unit and sponsored by BTS, titled “Mindsets: Gaining Buy-In to Strategy,” the majority of firms struggle to achieve buy-in to strategy, but those that personalize strategy throughout their organization significantly outperform their peers in terms of profitability, revenue growth and market share.
Business Simulations: Even More Powerful in Combination
Comprehensive deployment of business simulation and experiential learning programs combines live and online experiences. The deepest alignment, mindset shift and capability building takes place over time through a series of well-designed activities. Maximize impact by linking engagement and skill building to organizational objectives and by involving leadership throughout the process.
Putting Business Simulations to Work
Simulations drive strategic alignment, sales force transformation, and business acumen, financial acumen and leadership development, among other areas. A successful experiential learning program cements strategic alignment and builds execution capability across the entire organization, turning strategy into action. Results can be measured in team effectiveness, company alignment, revenue growth and share price.
Learn more about business simulations
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