Positivity becomes toxic when it feels forced. When it ignores obvious problems. When it discounts what people are feeling or seeing. Most of the time it is not about morale. It is about discomfort. Leaders reach for positivity when they don't want to sit in the tension of a hard situation. If everything sounds upbeat, maybe the problem feels smaller. It doesn't.
Read MoreEmotionally, walking away from a past loss feels worse than risking a future one. Psychologists call this loss aversion. People feel losses more intensely than equivalent gains. A million-dollar loss feels catastrophic in a way a potential million-dollar gain never will. That is why leaders keep pouring resources into failing projects.
Read MoreWhen someone says or does something that bothers you, there's a fork in the road. One path is judgment. The other is curiosity. Judgment is faster. It feels decisive. Especially under pressure. Curiosity takes more time. It requires vulnerability. It risks hearing something you don't like. So most leaders default to judgment.
Read MoreFounder mode is neither good nor bad. Hustle is neither noble nor toxic. The real question is simpler and harder. Is the urgency coming from the needs of the business, or from the wiring of the founder? I see this constantly. Founders who built successful companies and cannot break through the next level of growth. Not because they stopped working hard, but because they never stopped working the same way.
Read MoreEntrepreneurs who build traction almost always skew urgent. That urgency is often what gets the company off the ground in the first place. At scale, that same instinct becomes disruptive. People struggle to understand priorities. Context switches constantly. Everything sounds like a crisis. Leaders start mistaking urgency for accountability and patience for disengagement. So founders hire someone to "balance" them. Often a COO, Chief of Staff, or operations leader who skews more patient. In theory, it's a purposeful pairing. In practice, it creates conflict.
Read MoreStrong cultures don't eliminate toxicity entirely. They detect it early and contain it fast. They have antibodies: clear values, frequent feedback, leaders who stay engaged even under pressure. The goal isn't perfection. It's resilience. Whether a single bad apple spoils the barrel is one of the clearest indicators of leadership quality
Read MoreMost leaders I work with dread annual planning. Not because planning is useless. Because everyone has an opinion on how you should do it. None of them run your business. And you’re stuck trying to satisfy everyone else’s version of “the right way” instead of figuring out what actually works for you. That’s the first problem.
Read MoreMany leaders do the same thing with every hard decision. If you’re waiting for the right time, you’ll never act. There is no perfect information. There is no risk-free moment. There is no version of this that doesn’t require courage. Make the decision. Or don’t. But stop pretending indecision is neutral.
Read MoreMost leaders don't call themselves perfectionists. They say they're being thorough. Setting the bar high. Still working to get it right. That's not always what's happening. Perfectionism rises as uncertainty rises. When leaders feel watched, judged, or exposed, perfection becomes the shield they grab.
Read MoreWhen you waffle, you're not avoiding a choice. You're making one. You're choosing to stay stuck. You're choosing to slow your team. You're choosing to let opportunities expire. Most of the time, the facts that informed your original decision haven't changed. Only your emotions have. Make the decision or don't. Stop pretending indecision is neutral.
Every high-performing team needs strengths from both sides of the spectrum. Long-term thinkers and short-term executors. Planners and improvisers. Structure followers and rule breakers. Without both, the team is weaker. Nowhere is that tension clearer than between team players and competitive players.
Read MoreResearch shows that when we see ourselves clearly, we’re more confident, more creative, and better decision-makers. We build stronger relationships, communicate more effectively, and lead more satisfied, higher-performing teams. Yet most leaders overestimate their self-awareness dramatically. Yet most leaders overestimate their self-awareness dramatically. In one study, 95% of people believed they were self-aware — but only 10 to 15% actually were.
Read MoreWhen uncertainty hits, employees want answers. If they don’t get them, they’ll make up their own. Usually jumping to the worst-case scenario in the process. That speculation erodes trust and compounds anxiety.
Read MoreOne-on-ones aren't optional. They're not nice-to-haves. They're the most important meetings on your calendar. The leaders who master one-on-ones don’t just have happier teams. They have better results.
Read MoreBeing detail-oriented is often what gets you promoted. It’s how you earn trust, build credibility, and prove you can deliver. But once you step into a true leadership seat, especially at the executive level, those same instincts can become your biggest liability.
Read MoreMost leaders hate meetings because they still think their real work is somewhere else. It’s not. The meeting is the work. It’s where coaching happens. Where friction gets surfaced and conflicts resolved. Where your values show up. If you’re phoning it in or constantly rescheduling, that’s the signal you’re sending to everyone else. You don’t have to love meetings. But you do have to learn how to lead inside them
Read MoreYou can’t fire Cal. He’s indispensable.” That’s what the Board told me on my first day as CEO. Cal was their lead engineer. He had decades of experience, deep technical knowledge, and a reputation for terrorizing anyone who dared disagree with him.
Read MoreHere’s that world famous list that thousands have been awaiting. Some of our Trajectify coaches and clients put together recommendations for books that they've been reading. We encourage you to use some of your vacation time and your days away from the office to invest in growth through reading. Wherever your adventures take you, even if it's just in your backyard hammock), use this out-of-office time to learn, reflect, and challenge yourself.
Read MoreMuch of the tech talk recently is about AI, specifically ChatGPT (generating text) and Lensa AI (generating images). So, I gave ChatGPT a request to write an article on how a CEO's ethics impacts the culture of the organization. While it lacks my charm and occasional snark, nor does it include the storytelling I often do, can you tell that it was machine-generated?
Read MoreHow many times have you been in an interview process when someone asks the question: “Will they fit in here?” Is there an objective way to answer that? The question of fit is based on careful business choices. It’s based on emotion, and we all know hiring isn’t a decision we should make emotionally. And yet…so many business leaders do.
Read MoreStartups and Small Businesses sometimes find themselves at the edge of a chasm. With success in developing and growing their business, a stage is reached where they find that the "next step" is a big one! Trajectify partners with the entrepreneur to build momentum and trajectory to be able to cross the chasm.
We offer private and group (Mastermind) coaching and hold frequent events and seminars.
Trajectify is founded my Mike Krupit, veteran of eight startups. Mike has helped dozens of companies grow and mentored and advised hundreds more.
I don't think every CEO needs to become a LinkedIn personality. The question is simpler. Who needs to know you exist? Where are they? And what would help them understand how you think before they ever sit across from you? That answer will change as the company grows, as your buyers change, as platforms come and go. You adjust. That I don’t think you can do anymore is decide visibility isn’t part of your job at all. Your personal brand is important to your company’s brand.
Most founders and executives I work with are uncomfortable talking about how they look. It feels shallow. Not the point. I get it. They started their companies because of a vision, not an ego. By the time they're working with an advisor, they're wrestling with real problems: who belongs in which seats, how to build accountability, how to run a leadership meeting. Thinking about personal image can feel self-indulgent by comparison.
Founders tend to think about a major transition as a singular event. You prepare, announce, close, and now you're a different company. In my experience, the company starts changing well before any of that happens. I've been through this several times now, and the details were different every time. The weirdness was pretty consistent.
Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Ask a room of leaders why they set goals and most will say accountability. That answer creates the problem. Goals exist for alignment. The company needs to reach a number, so this group does this, that group does that, and together the math works. Everyone is pointed in the same direction. Focus comes second. A good goal tells you what to say no to.
The instinct to build a team that moved in the same direction, at the same pace, with the same set of perspectives is limiting. Consistency is created at the expense of range. The goal isn't alignment of strengths. It's coverage. The most dangerous teams I've seen weren't the ones with conflict. hey were the ones with none. Where every conversation ends in agreement. Where nothing gets surfaced. Where the people who see things differently may have learned to stop saying so.
The same restlessness that makes it hard to stay on plan is what made them start the company in the first place. The wandering mind, the refusal to be satisfied with what already exists, the ability to see something before it exists: that's not a disorder. That's the source.
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I’ve been facilitating CEO peer groups for fifteen years. The biggest factor in whether someone gets value from a group is vulnerability. Not performative vulnerability. The kind that costs you something to say out loud, the thing you'd rather not say because it makes you look uncertain, stuck, bored, scared, or wrong. The people who get the most from these groups aren't necessarily the ones with the biggest problems. They're the ones willing to let the room see the problem clearly enough to help.