Technology used to be expensive to build, and relatively inexpensive labor was often the better return. AI has changed that calculation for certain kinds of work. Tasks that once required entire teams can now be automated relatively cheaply. I don’t think CEOs should pretend otherwise. I do think they need to be honest about what actually changed.
Read MoreFounders 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.
Read MoreThe 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.
Read MoreIf you're building a company, knowing your role isn't optional. The visionary needs someone who will build what they see without getting in the way of the seeing. The integrator needs someone who will point at the moon and mean it and keep pointing at the same moon long enough for the bridge to get built. The mistake I see most often: trying to be both or hiring someone who mirrors you when you need someone who complements you.
Read MoreRight people, right seats doesn't mean everyone eventually moves into a leadership role. It means finding the seat where each person does their best work and building a structure that makes those seats worth staying in. Create a path for people who want to grow as individual contributors. Create a separate path for people who want to lead. Reward both. Respect both. Pay both.
Read MoreDon't prevent scraped knees; prevent bus crashes. A scraped knee hurts. You might carry the scar for years. That's the point. The pain is proportional to the lesson. A bus crash can lead to catastrophic loss. The project. The company. The relationship. Something that can't be recovered. The leader's job isn't to eliminate mistakes. It's to know the difference between those two things.
Read MoreThe leader's job isn't to have the answer. It's to create conditions where the best answer can emerge. That means encouraging disagreement without punishment. Creating opportunities for information to move across functions. Making it safe for people to challenge assumptions, including your own. The highest-performing teams in these simulations don't succeed because they have the smartest leader. They succeed because nobody in the room is waiting for one person to have all the answers.
Read MoreThe leaders who are consistently good at managing up and across understand something most people miss: influence gets built long before it’s needed. Not through charisma. Not through politics. Through small, deliberate actions repeated consistently over time. Investments. Relationships are like a bank account. You have to make deposits before you can make withdrawals. Most people get this backwards.
Read MoreMost founders built their business from nothing. They were the product, the salesperson, the decision-maker, the culture. The company exists because they willed it into being. Somewhere along the way, being needed became part of who they are. That's not ego in the pejorative sense. It's human. We find meaning in being useful, in being the person others turn to.
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 MoreEvery 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 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 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 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 More94% of senior executives think it’s important to focus on the growth and development of their HR executives so they’re ready to face the future. Of course, if you don’t have an HR executive on your team, you can’t focus on developing them. That’s the time to begin thinking about hiring a Chief People Officer.
Read MoreAn interim executive temporarily takes a management position in an organization to help the existing leadership solve problems and set the future, permanent leader up for success. Knowing whether an interim executive is right for your organization depends on your current needs and your assumptions about the future.
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’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.
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.
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Technology used to be expensive to build, and relatively inexpensive labor was often the better return. AI has changed that calculation for certain kinds of work. Tasks that once required entire teams can now be automated relatively cheaply. I don’t think CEOs should pretend otherwise. I do think they need to be honest about what actually changed.